DE60012891T2 - Funktionalisierte polyproypelene und verfahren zu ihren herstellung - Google Patents
Funktionalisierte polyproypelene und verfahren zu ihren herstellung Download PDFInfo
- Publication number
- DE60012891T2 DE60012891T2 DE60012891T DE60012891T DE60012891T2 DE 60012891 T2 DE60012891 T2 DE 60012891T2 DE 60012891 T DE60012891 T DE 60012891T DE 60012891 T DE60012891 T DE 60012891T DE 60012891 T2 DE60012891 T2 DE 60012891T2
- Authority
- DE
- Germany
- Prior art keywords
- polypropylene
- functionalized
- free radical
- radical initiator
- amount
- 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
- 238000000034 method Methods 0.000 title claims description 53
- 238000004519 manufacturing process Methods 0.000 title description 5
- -1 polypropylene Polymers 0.000 claims description 151
- 229920001155 polypropylene Polymers 0.000 claims description 141
- 239000004743 Polypropylene Substances 0.000 claims description 134
- 239000003999 initiator Substances 0.000 claims description 68
- 150000003254 radicals Chemical class 0.000 claims description 41
- 239000003795 chemical substances by application Substances 0.000 claims description 23
- 229920000642 polymer Polymers 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 21
- 239000011541 reaction mixture Substances 0.000 claims description 14
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 13
- 238000004383 yellowing Methods 0.000 claims description 13
- 238000002844 melting Methods 0.000 claims description 10
- 230000008018 melting Effects 0.000 claims description 10
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical group CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 8
- 150000002978 peroxides Chemical group 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005977 Ethylene Substances 0.000 claims description 6
- 238000011084 recovery Methods 0.000 claims description 4
- 125000004018 acid anhydride group Chemical group 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 3
- 239000007924 injection Substances 0.000 claims description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000003039 volatile agent Substances 0.000 claims description 3
- 239000002245 particle Substances 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 36
- 239000000047 product Substances 0.000 description 19
- 239000008188 pellet Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000004698 Polyethylene Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 6
- 229920000573 polyethylene Polymers 0.000 description 6
- 229920000098 polyolefin Polymers 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 238000010924 continuous production Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 238000007306 functionalization reaction Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 238000013022 venting Methods 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- 239000012969 di-tertiary-butyl peroxide Substances 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical group CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 238000013467 fragmentation Methods 0.000 description 2
- 238000006062 fragmentation reaction Methods 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229920005606 polypropylene copolymer Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- KNDQHSIWLOJIGP-UMRXKNAASA-N (3ar,4s,7r,7as)-rel-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione Chemical compound O=C1OC(=O)[C@@H]2[C@H]1[C@]1([H])C=C[C@@]2([H])C1 KNDQHSIWLOJIGP-UMRXKNAASA-N 0.000 description 1
- XSZYESUNPWGWFQ-UHFFFAOYSA-N 1-(2-hydroperoxypropan-2-yl)-4-methylcyclohexane Chemical compound CC1CCC(C(C)(C)OO)CC1 XSZYESUNPWGWFQ-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical group C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- PMAAOHONJPSASX-UHFFFAOYSA-N 2-butylperoxypropan-2-ylbenzene Chemical group CCCCOOC(C)(C)C1=CC=CC=C1 PMAAOHONJPSASX-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Chemical group 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 240000001987 Pyrus communis Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013466 adhesive and sealant Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- UPIWXMRIPODGLE-UHFFFAOYSA-N butyl benzenecarboperoxoate Chemical group CCCCOOC(=O)C1=CC=CC=C1 UPIWXMRIPODGLE-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000007499 fusion processing Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- LDHQCZJRKDOVOX-IHWYPQMZSA-N isocrotonic acid Chemical compound C\C=C/C(O)=O LDHQCZJRKDOVOX-IHWYPQMZSA-N 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 229930004008 p-menthane Natural products 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920005629 polypropylene homopolymer Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- KOPQZJAYZFAPBC-UHFFFAOYSA-N propanoyl propaneperoxoate Chemical group CCC(=O)OOC(=O)CC KOPQZJAYZFAPBC-UHFFFAOYSA-N 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 229920006301 statistical copolymer Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- CFJYNSNXFXLKNS-UHFFFAOYSA-N trans-p-menthane Natural products CC(C)C1CCC(C)CC1 CFJYNSNXFXLKNS-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 238000010626 work up procedure Methods 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
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
- C08F255/02—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms
-
- 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
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US261720 | 1999-03-03 | ||
| US09/261,720 US6218476B1 (en) | 1999-03-03 | 1999-03-03 | Functionalized polypropylenes and process for production |
| PCT/US2000/002735 WO2000052065A1 (en) | 1999-03-03 | 2000-02-04 | Functionalized polypropylenes and process for production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60012891D1 DE60012891D1 (de) | 2004-09-16 |
| DE60012891T2 true DE60012891T2 (de) | 2004-12-30 |
Family
ID=22994563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60012891T Expired - Lifetime DE60012891T2 (de) | 1999-03-03 | 2000-02-04 | Funktionalisierte polyproypelene und verfahren zu ihren herstellung |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US6218476B1 (https=) |
| EP (1) | EP1155052B1 (https=) |
| JP (1) | JP4741083B2 (https=) |
| CN (1) | CN1352655A (https=) |
| BR (1) | BR0008581A (https=) |
| DE (1) | DE60012891T2 (https=) |
| WO (1) | WO2000052065A1 (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002030118A (ja) * | 2000-07-14 | 2002-01-31 | Tokyo Ohka Kogyo Co Ltd | 新規コポリマー、ホトレジスト組成物、および高アスペクト比のレジストパターン形成方法 |
| US8058354B2 (en) * | 2001-02-09 | 2011-11-15 | Eastman Chemical Company | Modified carboxylated polyolefins and their use as adhesion promoters |
| WO2003072644A2 (en) * | 2002-02-22 | 2003-09-04 | Dow Global Technologies Inc. | Thermoplastic foam containing particulate additive |
| US6855771B2 (en) * | 2002-10-31 | 2005-02-15 | Grant Doney | Process for making block polymers or copolymers from isotactic polypropylene |
| US20060069187A1 (en) * | 2004-09-29 | 2006-03-30 | Klosiewicz Daniel W | Functionalized polyolefin emulsions |
| US20060069209A1 (en) * | 2004-09-29 | 2006-03-30 | Klosiewicz Daniel W | Heat stable functionalized polyolefin emulsions |
| US8058355B2 (en) * | 2004-10-06 | 2011-11-15 | Eastman Chemical Company | Modified chlorinated carboxylated polyolefins and their use as adhesion promoters |
| EP1861438B1 (en) * | 2005-03-17 | 2015-03-04 | Dow Global Technologies LLC | Catalyst composition comprising shuttling agent for regio-irregular multi-block copolymer formation |
| US20070004864A1 (en) * | 2005-06-24 | 2007-01-04 | University Of Florida Research Foundation | Method to enhance impact strength properties of melt processed polypropylene resins |
| US7750078B2 (en) * | 2005-12-07 | 2010-07-06 | Exxonmobil Chemical Patents Inc. | Systems and methods used for functionalization of polymeric material and polymeric materials prepared therefrom |
| US20070208110A1 (en) * | 2006-03-03 | 2007-09-06 | Sigworth William D | Coupling agents for natural fiber-filled polyolefins |
| US20090088530A1 (en) * | 2007-09-28 | 2009-04-02 | Bodiford Billy Ray | Novel polymer compound and uses thereof |
| JP6328348B2 (ja) * | 2015-02-04 | 2018-05-23 | ボレアリス エージー | 押出し機において修飾オレフィンポリマーを生成するためのプロセス |
| ES2843255T3 (es) * | 2016-10-12 | 2021-07-16 | Dow Global Technologies Llc | Método para producir polímeros funcionalizados basados en etileno |
| WO2018228929A1 (en) * | 2017-06-13 | 2018-12-20 | Basell Poliolefine Italia S.R.L. | Polyolefin composition with reduced odor and fogging |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4376855A (en) | 1981-06-22 | 1983-03-15 | Eastman Kodak Company | Emulsifiable ethylene containing polyolefin waxes having improved emulsifiability and process for their preparation |
| US4578428A (en) | 1983-12-16 | 1986-03-25 | Montedison S.P.A. | Modified olefine polymers and process for their manufacture |
| US4762890A (en) | 1986-09-05 | 1988-08-09 | The Dow Chemical Company | Method of grafting maleic anhydride to polymers |
| US4927888A (en) | 1986-09-05 | 1990-05-22 | The Dow Chemical Company | Maleic anhydride graft copolymers having low yellowness index and films containing the same |
| US4857600A (en) | 1988-05-23 | 1989-08-15 | Union Carbide Corporation | Process for grafting diacid anhydrides |
| CA1339160C (en) | 1988-08-09 | 1997-07-29 | Chad A. Strait | Maleic anhydride graft copolymers having low yellowness index and films containing the same |
| US5140074A (en) | 1990-01-26 | 1992-08-18 | Himont Incorporated | Method of producing olefin polymer graft copolymers |
| FI85587C (fi) * | 1990-06-15 | 1992-05-11 | Neste Oy | Foerfarande foer modifiering av olefinpolymerer till sammankopplingsmedel. |
| JP3244829B2 (ja) * | 1992-12-28 | 2002-01-07 | 日本石油化学株式会社 | ポリプロピレンの変性方法 |
| CA2162721A1 (en) | 1993-05-12 | 1994-11-24 | Daniel J. Cosgrove | Expansins, proteins that catalyze plant cell wall expansion and weakening of paper fiber connections |
| BE1007888A3 (fr) * | 1993-12-27 | 1995-11-14 | Solvay | Procede continu de greffage d'une polyolefine, les polyolefines greffees obtenues au moyen de ce procede. |
| TW325482B (en) | 1994-01-31 | 1998-01-21 | Himont Inc | A process for sequentially grafting olefin polymer materials and grafted polymer therefrom |
| JPH07316239A (ja) * | 1994-03-31 | 1995-12-05 | Kawasaki Steel Corp | 変性ポリオレフィンの製造方法およびガラス繊維強化ポリオレフィン |
| KR970705587A (ko) * | 1994-08-25 | 1997-10-09 | 그윈넬 해리 제이 | 고산가 고분자량 저색도 말레화 폴리프로필렌(maleated high acid number high molecular weight polypropylene of low color) |
| JPH093124A (ja) * | 1995-06-19 | 1997-01-07 | Ube Ind Ltd | 改質された非晶質ポリオレフィンおよびその連続製造 方法 |
-
1999
- 1999-03-03 US US09/261,720 patent/US6218476B1/en not_active Expired - Lifetime
-
2000
- 2000-02-04 WO PCT/US2000/002735 patent/WO2000052065A1/en not_active Ceased
- 2000-02-04 EP EP00905934A patent/EP1155052B1/en not_active Expired - Lifetime
- 2000-02-04 BR BR0008581-2A patent/BR0008581A/pt not_active Application Discontinuation
- 2000-02-04 CN CN00807588.3A patent/CN1352655A/zh active Pending
- 2000-02-04 DE DE60012891T patent/DE60012891T2/de not_active Expired - Lifetime
- 2000-02-04 JP JP2000602287A patent/JP4741083B2/ja not_active Expired - Fee Related
-
2001
- 2001-01-31 US US09/774,860 patent/US6426389B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1155052B1 (en) | 2004-08-11 |
| EP1155052A1 (en) | 2001-11-21 |
| JP4741083B2 (ja) | 2011-08-03 |
| US6218476B1 (en) | 2001-04-17 |
| CN1352655A (zh) | 2002-06-05 |
| WO2000052065A1 (en) | 2000-09-08 |
| BR0008581A (pt) | 2002-02-05 |
| US6426389B2 (en) | 2002-07-30 |
| DE60012891D1 (de) | 2004-09-16 |
| US20010012876A1 (en) | 2001-08-09 |
| JP2002538238A (ja) | 2002-11-12 |
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