AU2009249138A1 - Ethylene tetrafluoroethylene (meth)acrylate copolymers - Google Patents
Ethylene tetrafluoroethylene (meth)acrylate copolymers Download PDFInfo
- Publication number
- AU2009249138A1 AU2009249138A1 AU2009249138A AU2009249138A AU2009249138A1 AU 2009249138 A1 AU2009249138 A1 AU 2009249138A1 AU 2009249138 A AU2009249138 A AU 2009249138A AU 2009249138 A AU2009249138 A AU 2009249138A AU 2009249138 A1 AU2009249138 A1 AU 2009249138A1
- Authority
- AU
- Australia
- Prior art keywords
- mixture
- repellency
- water
- meth
- acrylate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
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- 229920001577 copolymer Polymers 0.000 title claims abstract description 86
- 229920000840 ethylene tetrafluoroethylene copolymer Polymers 0.000 title description 16
- QHSJIZLJUFMIFP-UHFFFAOYSA-N ethene;1,1,2,2-tetrafluoroethene Chemical group C=C.FC(F)=C(F)F QHSJIZLJUFMIFP-UHFFFAOYSA-N 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 190
- 239000000178 monomer Substances 0.000 claims abstract description 87
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 52
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 41
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 11
- 125000006165 cyclic alkyl group Chemical group 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 153
- 239000004744 fabric Substances 0.000 claims description 137
- 238000000034 method Methods 0.000 claims description 78
- -1 methyl-substituted styrene Chemical class 0.000 claims description 76
- 239000000758 substrate Substances 0.000 claims description 58
- 239000003921 oil Substances 0.000 claims description 55
- 229920000728 polyester Polymers 0.000 claims description 50
- 239000004753 textile Substances 0.000 claims description 49
- 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 29
- 239000000123 paper Substances 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000002689 soil Substances 0.000 claims description 25
- 229920000742 Cotton Polymers 0.000 claims description 21
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 14
- 239000000835 fiber Substances 0.000 claims description 13
- 239000010985 leather Substances 0.000 claims description 12
- 239000004698 Polyethylene Substances 0.000 claims description 11
- 239000004743 Polypropylene Substances 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 11
- 229920000573 polyethylene Polymers 0.000 claims description 11
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 9
- 229920001155 polypropylene Polymers 0.000 claims description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- 239000004952 Polyamide Substances 0.000 claims description 8
- 229920002647 polyamide Polymers 0.000 claims description 8
- 229920000098 polyolefin Polymers 0.000 claims description 8
- 239000012948 isocyanate Substances 0.000 claims description 7
- 150000002513 isocyanates Chemical class 0.000 claims description 7
- 239000004094 surface-active agent Substances 0.000 claims description 7
- 239000004567 concrete Substances 0.000 claims description 6
- 239000011521 glass Substances 0.000 claims description 6
- 239000004606 Fillers/Extenders Substances 0.000 claims description 5
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 5
- 239000004575 stone Substances 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical class [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- 244000025254 Cannabis sativa Species 0.000 claims description 4
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 claims description 4
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 claims description 4
- 235000019738 Limestone Nutrition 0.000 claims description 4
- 229910002651 NO3 Inorganic materials 0.000 claims description 4
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 4
- 229920000297 Rayon Polymers 0.000 claims description 4
- 239000011449 brick Substances 0.000 claims description 4
- 235000009120 camo Nutrition 0.000 claims description 4
- 229920002301 cellulose acetate Polymers 0.000 claims description 4
- 235000005607 chanvre indien Nutrition 0.000 claims description 4
- 239000004927 clay Substances 0.000 claims description 4
- 239000011487 hemp Substances 0.000 claims description 4
- 229910052742 iron Inorganic materials 0.000 claims description 4
- 239000006028 limestone Substances 0.000 claims description 4
- 239000002964 rayon Substances 0.000 claims description 4
- 210000002268 wool Anatomy 0.000 claims description 4
- 229920002334 Spandex Polymers 0.000 claims description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 3
- 239000010438 granite Substances 0.000 claims description 3
- 239000011440 grout Substances 0.000 claims description 3
- 239000010440 gypsum Substances 0.000 claims description 3
- 229910052602 gypsum Inorganic materials 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000004579 marble Substances 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 239000004570 mortar (masonry) Substances 0.000 claims description 3
- 239000004759 spandex Substances 0.000 claims description 3
- 239000000080 wetting agent Substances 0.000 claims description 3
- 239000002023 wood Substances 0.000 claims description 3
- 230000037303 wrinkles Effects 0.000 claims description 3
- 239000004971 Cross linker Substances 0.000 claims description 2
- 230000000845 anti-microbial effect Effects 0.000 claims description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 239000006187 pill Substances 0.000 claims description 2
- 150000003440 styrenes Chemical class 0.000 claims description 2
- 230000037072 sun protection Effects 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 239000003002 pH adjusting agent Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 125000005739 1,1,2,2-tetrafluoroethanediyl group Chemical group FC(F)([*:1])C(F)(F)[*:2] 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
- 239000000047 product Substances 0.000 description 69
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 68
- 238000010998 test method Methods 0.000 description 65
- 239000000243 solution Substances 0.000 description 56
- 229920000642 polymer Polymers 0.000 description 55
- 235000019198 oils Nutrition 0.000 description 52
- 239000007787 solid Substances 0.000 description 49
- 238000012360 testing method Methods 0.000 description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 239000007921 spray Substances 0.000 description 42
- 239000004677 Nylon Substances 0.000 description 41
- 239000000839 emulsion Substances 0.000 description 41
- 229920001778 nylon Polymers 0.000 description 41
- 239000011541 reaction mixture Substances 0.000 description 41
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 36
- 239000000523 sample Substances 0.000 description 31
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 239000004745 nonwoven fabric Substances 0.000 description 29
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 27
- 239000011737 fluorine Substances 0.000 description 27
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 239000007788 liquid Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000005977 Ethylene Substances 0.000 description 15
- 150000003573 thiols Chemical class 0.000 description 15
- 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 14
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 150000004694 iodide salts Chemical class 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 12
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 12
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 12
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 12
- 150000001298 alcohols Chemical class 0.000 description 11
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 10
- 239000008367 deionised water Substances 0.000 description 10
- 229910021641 deionized water Inorganic materials 0.000 description 10
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 10
- 239000003999 initiator Substances 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 239000012265 solid product Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000004772 Sontara Substances 0.000 description 9
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 9
- 229920000139 polyethylene terephthalate Polymers 0.000 description 9
- 239000005020 polyethylene terephthalate Substances 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- 238000009736 wetting Methods 0.000 description 9
- 229920002799 BoPET Polymers 0.000 description 8
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 8
- 239000005041 Mylar™ Substances 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- PPXVPFPTMXFUDE-UHFFFAOYSA-N 1,1,1,2,2-pentafluoro-4-iodobutane Chemical group FC(F)(F)C(F)(F)CCI PPXVPFPTMXFUDE-UHFFFAOYSA-N 0.000 description 7
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 7
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 7
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 7
- 230000035515 penetration Effects 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000005968 1-Decanol Substances 0.000 description 6
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 6
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 6
- 229920000058 polyacrylate Polymers 0.000 description 6
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
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- 239000010410 layer Substances 0.000 description 5
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 5
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- 238000006384 oligomerization reaction Methods 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 238000010926 purge Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 4
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 4
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 4
- 241000283690 Bos taurus Species 0.000 description 4
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- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
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- 229940126214 compound 3 Drugs 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
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- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
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- 238000007655 standard test method Methods 0.000 description 4
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- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 3
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- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 3
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- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 3
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- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 3
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- LQZZUXJYWNFBMV-UHFFFAOYSA-N ethyl butylhexanol Natural products CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000004751 flashspun nonwoven Substances 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical group FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 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 1
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
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- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
- 229940117841 methacrylic acid copolymer Drugs 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- YBXBWBBVLXZQBJ-UHFFFAOYSA-N n-[2-(5-hydroxy-2-methyl-1h-indol-3-yl)ethyl]-2-methoxyacetamide Chemical compound C1=C(O)C=C2C(CCNC(=O)COC)=C(C)NC2=C1 YBXBWBBVLXZQBJ-UHFFFAOYSA-N 0.000 description 1
- 229940094933 n-dodecane Drugs 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229920006120 non-fluorinated polymer Polymers 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002215 polytrimethylene terephthalate Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
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- 238000003908 quality control method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
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- 230000002940 repellent Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000008149 soap solution Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- FVEFRICMTUKAML-UHFFFAOYSA-M sodium tetradecyl sulfate Chemical compound [Na+].CCCCC(CC)CCC(CC(C)C)OS([O-])(=O)=O FVEFRICMTUKAML-UHFFFAOYSA-M 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
- RBBWNXJFTBCLKT-UHFFFAOYSA-M sodium;ethanethioate Chemical compound [Na+].CC([S-])=O RBBWNXJFTBCLKT-UHFFFAOYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000003797 telogen phase Effects 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 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 1
- CEYYIKYYFSTQRU-UHFFFAOYSA-M trimethyl(tetradecyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)C CEYYIKYYFSTQRU-UHFFFAOYSA-M 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
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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
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F220/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
-
- 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
- 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
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/38—Esters containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
- C09D133/16—Homopolymers or copolymers of esters containing halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/24—Homopolymers or copolymers of amides or imides
- C09D133/26—Homopolymers or copolymers of acrylamide or methacrylamide
-
- 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
- Y10T428/23907—Pile or nap type surface or component
- Y10T428/2395—Nap type surface
-
- 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
- Y10T428/23907—Pile or nap type surface or component
- Y10T428/23986—With coating, impregnation, or bond
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/154,082 | 2008-05-20 | ||
| US12/154,082 US8318877B2 (en) | 2008-05-20 | 2008-05-20 | Ethylene tetrafluoroethylene (meth)acrylate copolymers |
| PCT/US2009/044580 WO2009143194A1 (en) | 2008-05-20 | 2009-05-20 | Ethylene tetrafluoroethylene (meth)acrylate copolymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2009249138A1 true AU2009249138A1 (en) | 2009-11-26 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2009249138A Abandoned AU2009249138A1 (en) | 2008-05-20 | 2009-05-20 | Ethylene tetrafluoroethylene (meth)acrylate copolymers |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8318877B2 (enExample) |
| EP (1) | EP2283051B1 (enExample) |
| JP (1) | JP2011523432A (enExample) |
| KR (1) | KR20110020270A (enExample) |
| CN (1) | CN102037033A (enExample) |
| AT (1) | ATE544790T1 (enExample) |
| AU (1) | AU2009249138A1 (enExample) |
| CA (1) | CA2721147A1 (enExample) |
| WO (1) | WO2009143194A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US8501888B2 (en) * | 2007-09-10 | 2013-08-06 | Unimatec Co., Ltd. | Fluorine-containing polymer and surface-modifying agent containing the same as active ingredient |
| GB0814955D0 (en) | 2008-08-18 | 2008-09-24 | 3M Innovative Properties Co | Azide-containing fluoropolymers and their preparation |
| JP5482762B2 (ja) * | 2011-10-18 | 2014-05-07 | ユニマテック株式会社 | 含フッ素共重合体およびこれを有効成分とする表面改質剤 |
| FR2986004B1 (fr) | 2012-01-25 | 2014-03-14 | Seppic Sa | Nouveau polymere epaississant reduisant le caractere collant des formules cosmetiques a base de glycerine |
| TWI496874B (zh) | 2012-06-26 | 2015-08-21 | Ind Tech Res Inst | 高分子安定化之光學等向性液晶配方及光學等向性液晶元件 |
| CN104508074B (zh) * | 2012-08-01 | 2016-09-21 | 旭硝子株式会社 | 拒水拒油剂组合物以及物品 |
| US9534343B2 (en) * | 2012-10-18 | 2017-01-03 | The Chemours Company Fc, Llc | Partially fluorinated copolymer emulsions containing fatty acids and esters |
| JP6855049B2 (ja) * | 2016-02-26 | 2021-04-07 | 国立大学法人神戸大学 | 機能性ポリオレフィンの製造方法 |
| WO2019051415A1 (en) * | 2017-09-11 | 2019-03-14 | Honeywell International Inc. | PAINT COMPOSITIONS CONTAINING COPOLYMER FORMULATIONS FOR ENHANCING ADHESION ON METALLIC SUBSTRATES |
| CN111406077B (zh) * | 2017-09-27 | 2024-07-05 | 阿科玛股份有限公司 | 卤代烯烃和卤代共聚单体的共聚物 |
| US11059990B2 (en) * | 2018-10-15 | 2021-07-13 | Metashield Llc | Anti-fouling coatings |
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| US2411158A (en) | 1943-04-23 | 1946-11-19 | Du Pont | Saturated polyfluoro carbonyl compounds and their preparation |
| US2559628A (en) | 1944-04-22 | 1951-07-10 | Du Pont | Fluorine-containing alcohols and process for preparing the same |
| US2562547A (en) | 1944-12-11 | 1951-07-31 | Du Pont | Fluorinated compounds |
| US3105824A (en) | 1960-05-03 | 1963-10-01 | Du Pont | Aqueous fluorocarbon telomer dispersion and process of preparing same |
| US3016407A (en) | 1960-09-21 | 1962-01-09 | Du Pont | Telomers from ch=ch and icf2cf2i |
| US3253978A (en) | 1961-07-19 | 1966-05-31 | C H Dexter & Sons Inc | Method of forming an inorganic waterlaid sheet containing colloidal silica and cationic starch |
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| DE2034472C3 (de) | 1970-07-11 | 1973-10-25 | Kali-Chemie Ag, 3000 Hannover | Verfahren zur Herstellung von Perfluor alkyljodidtelomeren |
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| BE792762A (fr) | 1971-12-16 | 1973-03-30 | Kali Chemie Ag | Procede de production de telomeres d'iodures de perfluoroalkyle |
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| US7078445B2 (en) | 2001-02-01 | 2006-07-18 | E. I. Du Pont De Nemours And Company | Photosensitive acrylate composition and waveguide device |
| EP1364934A4 (en) * | 2001-02-07 | 2005-12-21 | Daikin Ind Ltd | PROCESS FOR PREPARING A FLUORO ALKYLIODIDE-TELOMER MIXTURE AND METHOD FOR PRODUCING FLUOR-CONTAINING (METH) ACRYLATE ESTERS |
| JP2002316956A (ja) | 2001-04-17 | 2002-10-31 | Daikin Ind Ltd | パーフルオロアルキルアイオダイドテロマーの製造方法 |
| US6831025B2 (en) | 2001-06-18 | 2004-12-14 | E. I. Du Pont De Nemours And Company | Multiple component spunbond web and laminates thereof |
| MXPA04011448A (es) | 2002-05-24 | 2005-03-23 | 3M Innovative Properties Co | Composicion fluoroquimica para el tratamiento de un substrato fibroso. |
| JP2004131493A (ja) | 2002-09-20 | 2004-04-30 | Dainippon Ink & Chem Inc | フッ素系界面活性剤 |
| JP2004256406A (ja) | 2003-02-25 | 2004-09-16 | Daikin Ind Ltd | 含フッ素アルキルエチルハロゲン化物及び含フッ素アルカンの製造方法 |
| JP2004269413A (ja) | 2003-03-07 | 2004-09-30 | Daikin Ind Ltd | フルオロアルキルアイオダイドテロマー混合物および含フッ素（メタ）アクリル酸エステル混合物の製造方法 |
| CN1832973A (zh) * | 2003-08-21 | 2006-09-13 | 旭硝子株式会社 | 含氟共聚物及其制造方法、以及含有该共聚物的抗蚀组合物 |
| US7294610B2 (en) | 2004-03-03 | 2007-11-13 | 3M Innovative Properties Company | Fluorinated sulfonamide surfactants for aqueous cleaning solutions |
| US7344758B2 (en) | 2004-09-07 | 2008-03-18 | E.I. Du Pont De Nemours And Company | Hydrocarbon extenders for surface effect compositions |
| US7345123B2 (en) * | 2004-12-28 | 2008-03-18 | 3M Innovative Properties Company | Fluoroacrylate-multifunctional acrylate copolymer compositions |
| GB0525978D0 (en) | 2005-12-21 | 2006-02-01 | 3M Innovative Properties Co | Fluorinated Surfactants For Making Fluoropolymers |
| KR20080085016A (ko) | 2006-01-10 | 2008-09-22 | 클라리언트 파이넌스 (비브이아이)리미티드 | 불소계 텔로머 화합물 및 이를 함유하는 중합체 |
| WO2008019111A2 (en) | 2006-08-03 | 2008-02-14 | Great Lakes Chemical Corporation | Telomer compositions and production processes |
| US20080202384A1 (en) | 2007-02-28 | 2008-08-28 | Sheng Peng | Fluoropolymer compositions and method of use |
| US20090148653A1 (en) * | 2007-12-07 | 2009-06-11 | E.I. Du Pont De Nemours And Company | Fluoropolymer emulsions |
-
2008
- 2008-05-20 US US12/154,082 patent/US8318877B2/en not_active Expired - Fee Related
-
2009
- 2009-05-20 EP EP20090751422 patent/EP2283051B1/en not_active Not-in-force
- 2009-05-20 CN CN2009801183030A patent/CN102037033A/zh active Pending
- 2009-05-20 JP JP2011510663A patent/JP2011523432A/ja active Pending
- 2009-05-20 AU AU2009249138A patent/AU2009249138A1/en not_active Abandoned
- 2009-05-20 WO PCT/US2009/044580 patent/WO2009143194A1/en not_active Ceased
- 2009-05-20 KR KR1020107028517A patent/KR20110020270A/ko not_active Withdrawn
- 2009-05-20 AT AT09751422T patent/ATE544790T1/de active
- 2009-05-20 CA CA 2721147 patent/CA2721147A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20090291222A1 (en) | 2009-11-26 |
| ATE544790T1 (de) | 2012-02-15 |
| CN102037033A (zh) | 2011-04-27 |
| EP2283051A1 (en) | 2011-02-16 |
| WO2009143194A1 (en) | 2009-11-26 |
| CA2721147A1 (en) | 2009-11-26 |
| JP2011523432A (ja) | 2011-08-11 |
| US8318877B2 (en) | 2012-11-27 |
| EP2283051B1 (en) | 2012-02-08 |
| KR20110020270A (ko) | 2011-03-02 |
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| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |