CA2321363A1 - Catalyseur solide supporte utilisable pour la polymerisation de dienes conjugues, son procede de preparation et procede de polymerisation de dienes conjugues utilisant ce catalyseur - Google Patents
Catalyseur solide supporte utilisable pour la polymerisation de dienes conjugues, son procede de preparation et procede de polymerisation de dienes conjugues utilisant ce catalyseur Download PDFInfo
- Publication number
- CA2321363A1 CA2321363A1 CA002321363A CA2321363A CA2321363A1 CA 2321363 A1 CA2321363 A1 CA 2321363A1 CA 002321363 A CA002321363 A CA 002321363A CA 2321363 A CA2321363 A CA 2321363A CA 2321363 A1 CA2321363 A1 CA 2321363A1
- Authority
- CA
- Canada
- Prior art keywords
- catalyst
- aluminum
- formula
- polymerization
- solid support
- 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
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 86
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 44
- 238000002360 preparation method Methods 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims abstract description 30
- 239000011949 solid catalyst Substances 0.000 title claims abstract description 20
- 150000001993 dienes Chemical class 0.000 title claims abstract description 17
- 239000007787 solid Substances 0.000 claims abstract description 85
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 51
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 238000006243 chemical reaction Methods 0.000 claims abstract description 42
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 35
- -1 metal oxide compound Chemical class 0.000 claims abstract description 32
- 239000002904 solvent Substances 0.000 claims abstract description 29
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 24
- 229910052761 rare earth metal Inorganic materials 0.000 claims abstract description 22
- 150000002910 rare earth metals Chemical class 0.000 claims abstract description 17
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 15
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 15
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 15
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 15
- 229910052751 metal Inorganic materials 0.000 claims abstract description 13
- 239000002184 metal Substances 0.000 claims abstract description 13
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
- 239000000460 chlorine Substances 0.000 claims abstract description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 9
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 9
- 239000011737 fluorine Substances 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical group 0.000 claims abstract description 9
- 150000004945 aromatic hydrocarbons Chemical group 0.000 claims abstract description 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000002739 metals Chemical class 0.000 claims abstract description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 52
- 239000002841 Lewis acid Substances 0.000 claims description 24
- 150000007517 lewis acids Chemical class 0.000 claims description 24
- 239000012190 activator Substances 0.000 claims description 14
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 12
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 9
- 150000004820 halides Chemical class 0.000 claims description 8
- 229910052779 Neodymium Inorganic materials 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical group [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 claims description 6
- 150000004706 metal oxides Chemical class 0.000 claims description 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 229910052718 tin Inorganic materials 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- 239000010936 titanium Substances 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052787 antimony Inorganic materials 0.000 claims description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 claims description 3
- 229910052735 hafnium Inorganic materials 0.000 claims description 3
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 229910052726 zirconium Inorganic materials 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910001507 metal halide Inorganic materials 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 230000000737 periodic effect Effects 0.000 abstract description 3
- 230000003213 activating effect Effects 0.000 abstract description 2
- 238000006555 catalytic reaction Methods 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 92
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 72
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 229920000642 polymer Polymers 0.000 description 14
- 239000005062 Polybutadiene Substances 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 229920002857 polybutadiene Polymers 0.000 description 12
- 238000001556 precipitation Methods 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- ATINCSYRHURBSP-UHFFFAOYSA-K neodymium(iii) chloride Chemical compound Cl[Nd](Cl)Cl ATINCSYRHURBSP-UHFFFAOYSA-K 0.000 description 9
- 229910017544 NdCl3 Inorganic materials 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000002815 homogeneous catalyst Substances 0.000 description 5
- 229920001195 polyisoprene Polymers 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- LHBNLZDGIPPZLL-UHFFFAOYSA-K praseodymium(iii) chloride Chemical compound Cl[Pr](Cl)Cl LHBNLZDGIPPZLL-UHFFFAOYSA-K 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910019328 PrCl3 Inorganic materials 0.000 description 1
- 229910052777 Praseodymium Inorganic materials 0.000 description 1
- 229910003074 TiCl4 Inorganic materials 0.000 description 1
- GURLNXRFQUUOMW-UHFFFAOYSA-K [Al](Cl)(Cl)Cl.[AlH3] Chemical compound [Al](Cl)(Cl)Cl.[AlH3] GURLNXRFQUUOMW-UHFFFAOYSA-K 0.000 description 1
- VSKBCRUQHHGABO-UHFFFAOYSA-N [Al].[H][H].[H][H].[H][H] Chemical compound [Al].[H][H].[H][H].[H][H] VSKBCRUQHHGABO-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000005906 dihydroxylation reaction Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- PDPJQWYGJJBYLF-UHFFFAOYSA-J hafnium tetrachloride Chemical compound Cl[Hf](Cl)(Cl)Cl PDPJQWYGJJBYLF-UHFFFAOYSA-J 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000010952 in-situ formation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000010408 sweeping Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 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
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9912744A FR2799394A1 (fr) | 1999-10-11 | 1999-10-11 | Catalyseur solide supporte utilisable pour la polymerisation de dienes conjugues, son procede de preparation et procede de polymerisation de dienes conjugues utilisant ce catalyseur |
| FR99/12744 | 1999-10-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2321363A1 true CA2321363A1 (fr) | 2001-04-11 |
Family
ID=9550865
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002321363A Abandoned CA2321363A1 (fr) | 1999-10-11 | 2000-10-10 | Catalyseur solide supporte utilisable pour la polymerisation de dienes conjugues, son procede de preparation et procede de polymerisation de dienes conjugues utilisant ce catalyseur |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6949489B1 (https=) |
| EP (1) | EP1092733B1 (https=) |
| JP (1) | JP4982006B2 (https=) |
| AT (1) | ATE306503T1 (https=) |
| BR (1) | BR0004767B1 (https=) |
| CA (1) | CA2321363A1 (https=) |
| DE (1) | DE60023080T2 (https=) |
| ES (1) | ES2250062T3 (https=) |
| FR (1) | FR2799394A1 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2814737B1 (fr) * | 2000-10-03 | 2003-08-29 | Rhodia Terres Rares | Compose anhydre a base d'un halogenure de terre rare ou de gallium, son procede de preparation et son utilisation comme catalyseur |
| KR100550178B1 (ko) * | 2000-10-03 | 2006-02-10 | 로디아 일렉트로닉스 앤드 캐탈리시스 | 희토류 또는 갈륨 부가 조성물, 그의 제조 방법 및 그의 촉매로서의 용도 |
| CN100516103C (zh) | 2001-10-31 | 2009-07-22 | 米其林技术公司 | 轮胎胎面组合物用嵌段共聚物的制备方法,和这样的共聚物 |
| FR2886937B1 (fr) * | 2005-06-14 | 2007-08-10 | Michelin Soc Tech | Procede de preparation d'un elastomere dienique, tel qu'un polybutadiene |
| WO2009132514A1 (zh) | 2008-04-29 | 2009-11-05 | 中国科学院长春应用化学研究所 | 异戊二烯或丁二烯顺1，4-聚合双组分催化体系及聚合方法 |
| KR102063911B1 (ko) * | 2011-09-05 | 2020-01-08 | 피티티 글로벌 케미칼 피씨엘 | 보론 함유 실리카 지지체를 포함하는 고활성 올레핀 중합 촉매 및 그의 제조 방법 |
| EP2840095B1 (en) * | 2012-04-18 | 2020-06-17 | Bridgestone Corporation | Method for producing polymerization catalyst composition, polymerization catalyst composition, method for producing polymer composition, and polymer composition |
| CN105777963B (zh) * | 2014-12-23 | 2018-06-01 | 中国石油天然气股份有限公司 | 高门尼稀土顺丁橡胶的聚合方法 |
| CN105777955B (zh) * | 2014-12-23 | 2018-05-04 | 中国石油天然气股份有限公司 | 用于制备高门尼稀土顺丁橡胶的催化剂及其制备方法 |
| FR3037588B1 (fr) | 2015-06-19 | 2017-05-19 | Michelin & Cie | Copolymere elastomere thermoplastique a base d'elastomere dienique et de polypropylene, compositions le comprenant et procede de preparation |
| KR102156108B1 (ko) | 2015-12-23 | 2020-09-15 | 주식회사 엘지화학 | 공액디엔계 중합체의 제조방법 및 이로부터 제조된 공액디엔계 중합체 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9107378D0 (en) * | 1991-04-08 | 1991-05-22 | Ici Plc | Olefin polymerisation |
| IT1265049B1 (it) * | 1993-08-06 | 1996-10-28 | Eniricerche Spa | Complessi alogenati dei lantanidi e loro uso nella polimerizzazione di monomeri insaturi |
| DE4334045A1 (de) * | 1993-10-06 | 1995-04-13 | Bayer Ag | Katalysator, dessen Herstellung und Verwendung zur Gasphasenpolymerisation von konjugierten Dienen |
| IT1269805B (it) * | 1994-05-20 | 1997-04-15 | Enichem Spa | Catalizzatore per la (co)polimerizzazione dell'etilene e procedimento per il suo ottenimento |
| US5453471B1 (en) | 1994-08-02 | 1999-02-09 | Carbide Chemicals & Plastics T | Gas phase polymerization process |
-
1999
- 1999-10-11 FR FR9912744A patent/FR2799394A1/fr active Pending
-
2000
- 2000-10-06 DE DE60023080T patent/DE60023080T2/de not_active Expired - Lifetime
- 2000-10-06 EP EP00121835A patent/EP1092733B1/fr not_active Expired - Lifetime
- 2000-10-06 AT AT00121835T patent/ATE306503T1/de not_active IP Right Cessation
- 2000-10-06 ES ES00121835T patent/ES2250062T3/es not_active Expired - Lifetime
- 2000-10-10 CA CA002321363A patent/CA2321363A1/fr not_active Abandoned
- 2000-10-10 BR BRPI0004767-8A patent/BR0004767B1/pt not_active IP Right Cessation
- 2000-10-11 JP JP2000348831A patent/JP4982006B2/ja not_active Expired - Fee Related
- 2000-10-11 US US09/688,376 patent/US6949489B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR2799394A1 (fr) | 2001-04-13 |
| ES2250062T3 (es) | 2006-04-16 |
| ATE306503T1 (de) | 2005-10-15 |
| JP4982006B2 (ja) | 2012-07-25 |
| DE60023080T2 (de) | 2006-07-13 |
| BR0004767B1 (pt) | 2011-12-27 |
| EP1092733B1 (fr) | 2005-10-12 |
| BR0004767A (pt) | 2001-06-19 |
| EP1092733A1 (fr) | 2001-04-18 |
| JP2002030107A (ja) | 2002-01-31 |
| DE60023080D1 (de) | 2006-02-23 |
| US6949489B1 (en) | 2005-09-27 |
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