CA2372212C - Polymer processing additive containing a multimodalfluoropolymer and a melt processable thermoplastic polymer composition employing the same - Google Patents
Polymer processing additive containing a multimodalfluoropolymer and a melt processable thermoplastic polymer composition employing the same Download PDFInfo
- Publication number
- CA2372212C CA2372212C CA002372212A CA2372212A CA2372212C CA 2372212 C CA2372212 C CA 2372212C CA 002372212 A CA002372212 A CA 002372212A CA 2372212 A CA2372212 A CA 2372212A CA 2372212 C CA2372212 C CA 2372212C
- Authority
- CA
- Canada
- Prior art keywords
- processing additive
- composition according
- polymer
- additive composition
- melt
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 91
- 239000000155 melt Substances 0.000 title claims abstract description 31
- 229920001169 thermoplastic Polymers 0.000 title claims abstract description 16
- 238000010094 polymer processing Methods 0.000 title claims abstract description 11
- 239000000654 additive Substances 0.000 title claims description 60
- 230000000996 additive effect Effects 0.000 title claims description 58
- 229920000642 polymer Polymers 0.000 claims abstract description 103
- 229920002313 fluoropolymer Polymers 0.000 claims abstract description 80
- 239000004811 fluoropolymer Substances 0.000 claims abstract description 60
- 239000000178 monomer Substances 0.000 claims abstract description 43
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 18
- 238000012545 processing Methods 0.000 claims description 44
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 18
- 229920000098 polyolefin Polymers 0.000 claims description 13
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical group FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000004416 thermosoftening plastic Substances 0.000 claims description 7
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 238000010128 melt processing Methods 0.000 claims description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 2
- 239000006057 Non-nutritive feed additive Substances 0.000 abstract description 8
- 239000004711 α-olefin Substances 0.000 abstract description 2
- -1 polypropylene Polymers 0.000 description 45
- 238000001125 extrusion Methods 0.000 description 24
- 229920001577 copolymer Polymers 0.000 description 20
- 239000004215 Carbon black (E152) Substances 0.000 description 15
- 229930195733 hydrocarbon Natural products 0.000 description 15
- 150000002430 hydrocarbons Chemical class 0.000 description 15
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 12
- 230000007547 defect Effects 0.000 description 12
- 239000005977 Ethylene Substances 0.000 description 10
- 230000008569 process Effects 0.000 description 8
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 7
- 150000001336 alkenes Chemical class 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 6
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 6
- 239000004698 Polyethylene Substances 0.000 description 6
- 239000004614 Process Aid Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 125000005702 oxyalkylene group Chemical group 0.000 description 6
- 229920000573 polyethylene Polymers 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 5
- 229920001903 high density polyethylene Polymers 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 229920005862 polyol Polymers 0.000 description 5
- 150000003077 polyols Chemical class 0.000 description 5
- 229920001155 polypropylene Polymers 0.000 description 4
- 229920001897 terpolymer Polymers 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000004594 Masterbatch (MB) Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- 239000012986 chain transfer agent Substances 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 239000004700 high-density polyethylene Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 229920000092 linear low density polyethylene Polymers 0.000 description 3
- 239000004707 linear low-density polyethylene Substances 0.000 description 3
- 229920001684 low density polyethylene Polymers 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- HFNSTEOEZJBXIF-UHFFFAOYSA-N 2,2,4,5-tetrafluoro-1,3-dioxole Chemical class FC1=C(F)OC(F)(F)O1 HFNSTEOEZJBXIF-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229920010126 Linear Low Density Polyethylene (LLDPE) Polymers 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000009827 uniform distribution Methods 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- SXZSFWHOSHAKMN-UHFFFAOYSA-N 2,3,4,4',5-Pentachlorobiphenyl Chemical compound C1=CC(Cl)=CC=C1C1=CC(Cl)=C(Cl)C(Cl)=C1Cl SXZSFWHOSHAKMN-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- YTCHAEAIYHLXBK-UHFFFAOYSA-N 2-chloro-1,1,3,3,3-pentafluoroprop-1-ene Chemical compound FC(F)=C(Cl)C(F)(F)F YTCHAEAIYHLXBK-UHFFFAOYSA-N 0.000 description 1
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 1
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- REEBWSYYNPPSKV-UHFFFAOYSA-N 3-[(4-formylphenoxy)methyl]thiophene-2-carbonitrile Chemical compound C1=CC(C=O)=CC=C1OCC1=C(C#N)SC=C1 REEBWSYYNPPSKV-UHFFFAOYSA-N 0.000 description 1
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
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- 239000004642 Polyimide Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
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- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
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- 238000013461 design Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
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- 238000002474 experimental method Methods 0.000 description 1
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
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- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/04—Homopolymers or copolymers of ethene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/10—Homopolymers or copolymers of propene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/12—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/12—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
- C08L27/16—Homopolymers or copolymers or vinylidene fluoride
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/12—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
- C08L27/18—Homopolymers or copolymers or tetrafluoroethene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/311,107 | 1999-05-13 | ||
| US09/311,107 US6277919B1 (en) | 1999-05-13 | 1999-05-13 | Polymer processing additive containing a multimodal fluoropolymer and melt processable thermoplastic polymer composition employing the same |
| PCT/US1999/021280 WO2000069967A1 (en) | 1999-05-13 | 1999-09-16 | Polymer processing additive containing a multimodalfluoropolymer and a melt processable thermoplastic polymer composition employing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2372212A1 CA2372212A1 (en) | 2000-11-23 |
| CA2372212C true CA2372212C (en) | 2009-02-03 |
Family
ID=23205439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002372212A Expired - Lifetime CA2372212C (en) | 1999-05-13 | 1999-09-16 | Polymer processing additive containing a multimodalfluoropolymer and a melt processable thermoplastic polymer composition employing the same |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6277919B1 (OSRAM) |
| EP (2) | EP1591484B1 (OSRAM) |
| JP (1) | JP4593796B2 (OSRAM) |
| CN (1) | CN1352668A (OSRAM) |
| AT (1) | ATE515535T1 (OSRAM) |
| AU (1) | AU6146999A (OSRAM) |
| CA (1) | CA2372212C (OSRAM) |
| DE (1) | DE69928573T2 (OSRAM) |
| WO (1) | WO2000069967A1 (OSRAM) |
Families Citing this family (55)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6203873B1 (en) * | 1998-05-22 | 2001-03-20 | Dayco Products, Inc. | Blends of fluoroelastomer interpolymers with thermo fluoroplastic interpolymers and the use of such blends in hoses |
| US6960377B2 (en) * | 1998-05-01 | 2005-11-01 | Dayco Products, Llc | Fuel hose and its production |
| US20070218233A1 (en) * | 1998-05-22 | 2007-09-20 | Jeremy Duke | Fuel impermeable, fuel resistant hose having improved high temperature resistant characteristics |
| US6780481B1 (en) * | 1999-05-13 | 2004-08-24 | 3M Innovative Properties Company | Melt processable thermoplastic polymer composition |
| US6642310B2 (en) * | 2001-02-16 | 2003-11-04 | Dupont Dow Elastomers L.L.C. | Process aid for melt processable polymers |
| US6599982B2 (en) | 2001-11-08 | 2003-07-29 | Dupont Dow Elastomers L.L.C. | Process aid for melt processable polymers |
| US20030109646A1 (en) * | 2001-11-21 | 2003-06-12 | Daikin Institute Of Advanced Chemistry And Technology | Resin composition and method of producing shaped articles |
| ITMI20020598A1 (it) * | 2002-03-22 | 2003-09-22 | Ausimont Spa | Fluoroelastomeri vulcanizzabili |
| US6818695B2 (en) | 2002-05-20 | 2004-11-16 | 3M Innovative Properties Company | Extrudable thermoplastic compositions |
| US20040102572A1 (en) * | 2002-11-21 | 2004-05-27 | Katsuyoshi Kubo | Resin composition and process for producing molding |
| EP1592991B1 (en) * | 2003-02-10 | 2006-11-22 | Nanoptics Incorporated | Method and apparatus for manufacturing plastic optical transmission medium |
| BRPI0411119B1 (pt) * | 2003-06-09 | 2014-12-02 | 3M Innovative Properties Co | composição polimérica processável em fusão compreendendo polímero processável em fusão nãofluorado e fluoropolímero e método de produzir uma composição polimérica processável em fusão |
| US8236874B2 (en) * | 2003-06-11 | 2012-08-07 | 3M Innovative Properties Company | Compositions and method for improving the processing of polymer composites |
| US7402625B2 (en) * | 2003-06-11 | 2008-07-22 | 3M Innovative Properties Company | Compositions and method for improving the processing of polymer composites |
| US7238748B2 (en) * | 2003-08-20 | 2007-07-03 | Dupont Performance Elastomers L.L.C. | Process aid for metallocene catalyzed linear low density polyethylene polymers |
| US20050101722A1 (en) * | 2003-11-06 | 2005-05-12 | 3M Innovative Properties Company | Melt processable compositions |
| US7338995B2 (en) * | 2004-03-06 | 2008-03-04 | E.I. Du Pont De Nemours And Company | Titanium dioxide—containing polymers and films with reduced melt fracture |
| US20050245687A1 (en) * | 2004-04-30 | 2005-11-03 | Appel Marvin R | Multimodal polyethylene extrusion |
| US20050250908A1 (en) * | 2004-05-07 | 2005-11-10 | 3M Innovative Properties Company | Polymer melt additive composition and use thereof |
| ATE416465T1 (de) * | 2005-06-30 | 2008-12-15 | Borealis Tech Oy | Überzug-schicht für energie- oder kommunikationskabel |
| FR2896250B1 (fr) * | 2006-01-13 | 2012-08-17 | Arkema | Agent d'extrusion a base de pvdf |
| JP5231430B2 (ja) * | 2006-10-13 | 2013-07-10 | スリーエム イノベイティブ プロパティズ カンパニー | 窒素含有芳香性物質を含有する粉体塗装用フルオロポリマー組成物 |
| GB0801194D0 (en) * | 2008-01-23 | 2008-02-27 | 3M Innovative Properties Co | Processing aid compositions comprising fluoropolymers having long-chain branches |
| CN101945927B (zh) | 2008-02-15 | 2014-10-01 | 大金美国股份有限公司 | 四氟乙烯/六氟丙烯共聚物和其生产方法以及电线 |
| JP5623513B2 (ja) | 2009-05-29 | 2014-11-12 | ミリケン・アンド・カンパニーＭｉｌｌｉｋｅｎ ＆ Ｃｏｍｐａｎｙ | ポリマー組成物、ポリマー組成物から製造された物品及びポリマー組成物の成形方法 |
| AU2010287336B2 (en) * | 2009-08-27 | 2013-07-25 | Daikin Industries, Ltd. | Processing additive, molding composition, masterbatch of processing additive and molding article |
| US11274172B2 (en) | 2009-08-27 | 2022-03-15 | Daikin Industries, Ltd. | Processing additive, molding composition masterbatch of processing additive and molding article |
| EP2791240B1 (en) | 2011-12-16 | 2018-01-24 | 3M Innovative Properties Company | Processing aid composition derived from a sulfinate-containing molecule |
| EP2925815B1 (en) | 2012-11-30 | 2020-08-05 | 3M Innovative Properties Company | Additive composition and compositions and articles containing the same |
| WO2014203727A1 (ja) | 2013-06-21 | 2014-12-24 | ダイキン工業株式会社 | 加工助剤、及び組成物 |
| WO2015042415A1 (en) | 2013-09-20 | 2015-03-26 | 3M Innovative Properties Company | Polymer processing additive, compositions, and methods |
| WO2015098867A1 (ja) | 2013-12-26 | 2015-07-02 | ダイキン工業株式会社 | ポリオレフィン用加工助剤、及び、ポリオレフィン組成物 |
| JP6308059B2 (ja) * | 2014-07-15 | 2018-04-11 | ダイキン工業株式会社 | 成形用組成物の製造方法、及び、成形品の製造方法 |
| EP3156428B1 (en) | 2014-08-21 | 2020-03-04 | Daikin Industries, Ltd. | Processing aid |
| EP3234004B1 (en) | 2014-12-19 | 2020-07-01 | 3M Innovative Properties Company | Poly(oxyalkylene) polymer processing additive, compositions, and methods |
| JP6528552B2 (ja) | 2015-06-16 | 2019-06-12 | ダイキン工業株式会社 | ポリオレフィン用加工助剤及びポリオレフィン組成物 |
| JP2018532019A (ja) * | 2015-10-13 | 2018-11-01 | スリーエム イノベイティブ プロパティズ カンパニー | フルオロポリマー加工用添加剤、組成物、及び方法 |
| WO2017083241A1 (en) | 2015-11-10 | 2017-05-18 | 3M Innovative Properties Company | Processing aid composition comprising a sulfonate-containing fluorinated polymer |
| EP3374429A1 (en) | 2015-11-13 | 2018-09-19 | 3M Innovative Properties Company | Compositions including a bimodal blend of amorphous fluoropolymers and their uses |
| JP2018536761A (ja) | 2015-12-31 | 2018-12-13 | ミリケン・アンド・カンパニーＭｉｌｌｉｋｅｎ ＆ Ｃｏｍｐａｎｙ | ポリオレフィン組成物 |
| CN108368298B (zh) | 2015-12-31 | 2020-06-30 | 美利肯公司 | 聚烯烃组合物 |
| KR102161366B1 (ko) | 2015-12-31 | 2020-09-29 | 밀리켄 앤드 캄파니 | 정화제 조성물 및 이를 포함하는 폴리올레핀 조성물 |
| WO2017116770A1 (en) | 2015-12-31 | 2017-07-06 | Milliken & Company | Method for molding a polymer composition |
| TW201815845A (zh) * | 2016-05-17 | 2018-05-01 | ３Ｍ新設資產公司 | 包括二氟亞乙烯與四氟乙烯的共聚物之組成物及其使用方法 |
| KR102477403B1 (ko) | 2016-05-31 | 2022-12-13 | 밀리켄 앤드 캄파니 | 중합체 조성물, 이러한 조성물로부터 제조된 물품, 및 이러한 조성물의 성형 방법 |
| SG11202102319WA (en) | 2018-11-15 | 2021-04-29 | Abu Dhabi Polymers Co Ltd Borouge | Polymer composition for blow molding applications |
| RU2018141773A (ru) | 2018-11-27 | 2020-05-27 | 3М Инновейтив Пропертиз Компани | Композиции полимерных процессинговых добавок и изделия, полученные с использованием указанных композиций |
| MX2022013177A (es) | 2020-04-29 | 2022-11-30 | Nova Chem Int Sa | Proceso de extrusion de polimero. |
| JP2024524718A (ja) | 2021-07-14 | 2024-07-05 | ノバ ケミカルズ（インターナショナル）ソシエテ アノニム | フルオロポリマーを含まないポリマー加工助剤 |
| EP4516859A3 (en) | 2021-08-12 | 2025-04-30 | Nova Chemicals (International) S.A. | Block copolymer polymer processing aids |
| US20250368810A1 (en) | 2022-06-10 | 2025-12-04 | Nova Chemicals (International) S.A. | Fluorine free polymer processing aids |
| WO2023241955A1 (en) | 2022-06-15 | 2023-12-21 | Nova Chemicals (International) S.A. | Block copolymer polymer processing aids |
| CA3266125A1 (en) | 2022-10-11 | 2024-04-18 | Nova Chemicals Corporation | METALLIC SALT AS A POLYMER PROCESSING AUXILIARY |
| WO2025003837A1 (en) | 2023-06-26 | 2025-01-02 | Nova Chemicals (International) S.A. | Polar polymers as processing aids in polyethylene |
| CN117467266B (zh) * | 2023-10-30 | 2024-05-10 | 吉化集团吉林市星云化工有限公司 | 一种高生产速率的聚烯烃含氟聚合物助剂及其制备方法 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3125547A (en) | 1961-02-09 | 1964-03-17 | Extrudable composition consisting of | |
| DE2639109A1 (de) | 1976-08-31 | 1978-03-09 | Hoechst Ag | Copolymerisate des tetrafluoraethylens und verfahren zu deren herstellung |
| US4558141A (en) | 1981-11-19 | 1985-12-10 | E. I. Du Pont De Nemours And Company | Perfluorodioxole and its polymers |
| US4855013A (en) | 1984-08-13 | 1989-08-08 | Agency Of Industrial Science And Technology | Method for controlling the thickness of a thin crystal film |
| US5015693A (en) | 1988-04-15 | 1991-05-14 | Minnesota Mining And Manufacturing Company | Extrudable thermoplastic hydrocarbon polymer composition |
| US4904735A (en) | 1988-07-08 | 1990-02-27 | E. I. Du Pont De Nemours And Company | Processing aid for polymers |
| WO1991005013A1 (en) | 1989-10-06 | 1991-04-18 | E.I. Du Pont De Nemours And Company | Fluoropolymer process aids containing functional groups |
| US5064594A (en) | 1989-10-06 | 1991-11-12 | E. I. Du Pont De Nemours And Company | Extrusion process for difficultly-melt-processible polymers |
| US5010130A (en) | 1990-05-15 | 1991-04-23 | E. I. Du Pont De Nemours And Company | High melt viscosity fluoropolymer process aid |
| ES2087339T3 (es) * | 1991-05-27 | 1996-07-16 | Hoechst Ag | Procedimiento para la preparacion de poliolefinas con amplia distribucion de masas moleculares. |
| US5284184A (en) | 1992-04-14 | 1994-02-08 | Itt Corporation | Corrugated multi-layer tubing having at least one fluoroplastic layer |
| US5397897A (en) | 1992-04-17 | 1995-03-14 | Terumo Kabushiki Kaisha | Infrared sensor and method for production thereof |
| WO1995014719A1 (en) | 1992-08-28 | 1995-06-01 | E.I. Du Pont De Nemours And Company | Low-melting tetrafluoroethylene copolymer and its uses |
| BE1006615A3 (fr) * | 1993-01-25 | 1994-11-03 | Solvay | Compositions polymeriques destinees a la fabrication de cables et de tuyauteries flexibles et articles a base de ces compositions. |
| JPH07169334A (ja) * | 1993-10-08 | 1995-07-04 | Furukawa Electric Co Ltd:The | 発泡フッ素樹脂絶縁電線およびその製造方法 |
| US5587429A (en) * | 1995-04-04 | 1996-12-24 | E. I. Dupont De Nemours And Company | Processing aid system for polyolefins |
| US5710217A (en) | 1995-09-15 | 1998-01-20 | Minnesota Mining And Manufacturing Company | Extrudable thermoplastic hydrocarbon compositions |
| US5718974A (en) * | 1996-06-24 | 1998-02-17 | Union Carbide Chemicals & Plastics Technology Corporation | Cable jacket |
| IT1296968B1 (it) | 1997-12-15 | 1999-08-03 | Ausimont Spa | Elastomeri termoplastici fluorurati |
| DE19805832A1 (de) * | 1998-02-13 | 1999-08-19 | Dyneon Gmbh | Mischungen aus thermoplastischen Fluorpolymeren |
| ATE412018T1 (de) * | 1998-08-06 | 2008-11-15 | Eidgenoess Tech Hochschule | Schmelzverarbeitbares polytetrafluorethylen |
| US6734252B1 (en) * | 1999-01-29 | 2004-05-11 | 3M Innovative Properties Company | Melt processable thermoplastic polymer composition employing a polymer processing additive containing a fluorothermoplastic copolymer |
-
1999
- 1999-05-13 US US09/311,107 patent/US6277919B1/en not_active Expired - Lifetime
- 1999-09-16 CN CN99816639.1A patent/CN1352668A/zh active Pending
- 1999-09-16 CA CA002372212A patent/CA2372212C/en not_active Expired - Lifetime
- 1999-09-16 AT AT05076373T patent/ATE515535T1/de not_active IP Right Cessation
- 1999-09-16 EP EP05076373A patent/EP1591484B1/en not_active Expired - Lifetime
- 1999-09-16 DE DE69928573T patent/DE69928573T2/de not_active Expired - Lifetime
- 1999-09-16 EP EP99948254A patent/EP1183308B1/en not_active Expired - Lifetime
- 1999-09-16 AU AU61469/99A patent/AU6146999A/en not_active Abandoned
- 1999-09-16 WO PCT/US1999/021280 patent/WO2000069967A1/en not_active Ceased
- 1999-09-16 JP JP2000618380A patent/JP4593796B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ATE515535T1 (de) | 2011-07-15 |
| WO2000069967A1 (en) | 2000-11-23 |
| DE69928573D1 (de) | 2005-12-29 |
| AU6146999A (en) | 2000-12-05 |
| JP4593796B2 (ja) | 2010-12-08 |
| US6277919B1 (en) | 2001-08-21 |
| CN1352668A (zh) | 2002-06-05 |
| CA2372212A1 (en) | 2000-11-23 |
| JP2002544358A (ja) | 2002-12-24 |
| EP1183308A1 (en) | 2002-03-06 |
| EP1591484A1 (en) | 2005-11-02 |
| DE69928573T2 (de) | 2006-08-10 |
| EP1183308B1 (en) | 2005-11-23 |
| EP1591484B1 (en) | 2011-07-06 |
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