ZA200508625B - A process for the preparation of low branch content polybutadiene - Google Patents
A process for the preparation of low branch content polybutadiene Download PDFInfo
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- ZA200508625B ZA200508625B ZA200508625A ZA200508625A ZA200508625B ZA 200508625 B ZA200508625 B ZA 200508625B ZA 200508625 A ZA200508625 A ZA 200508625A ZA 200508625 A ZA200508625 A ZA 200508625A ZA 200508625 B ZA200508625 B ZA 200508625B
- Authority
- ZA
- South Africa
- Prior art keywords
- polymer
- process according
- polybutadiene
- stage
- value
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 79
- 229920002857 polybutadiene Polymers 0.000 title claims abstract description 70
- 239000005062 Polybutadiene Substances 0.000 title claims abstract description 58
- 230000008569 process Effects 0.000 title claims abstract description 50
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 229920000642 polymer Polymers 0.000 claims abstract description 196
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 64
- 239000007822 coupling agent Substances 0.000 claims abstract description 26
- 239000003921 oil Substances 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229920001577 copolymer Polymers 0.000 claims abstract description 10
- 150000002118 epoxides Chemical group 0.000 claims abstract description 7
- 239000000178 monomer Substances 0.000 claims abstract description 7
- 150000008064 anhydrides Chemical group 0.000 claims abstract description 4
- 238000011084 recovery Methods 0.000 claims abstract description 4
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- 239000000203 mixture Substances 0.000 claims description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- -1 neodymium carboxylates Chemical class 0.000 claims description 22
- 230000003197 catalytic effect Effects 0.000 claims description 21
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- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 claims description 6
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- HKOJTHDFGOISHL-UHFFFAOYSA-K 2,2-dimethylpropanoate neodymium(3+) Chemical compound [Nd+3].CC(C)(C)C([O-])=O.CC(C)(C)C([O-])=O.CC(C)(C)C([O-])=O HKOJTHDFGOISHL-UHFFFAOYSA-K 0.000 claims description 2
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
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- MGMXGCZJYUCMGY-UHFFFAOYSA-N tris(4-nonylphenyl) phosphite Chemical compound C1=CC(CCCCCCCCC)=CC=C1OP(OC=1C=CC(CCCCCCCCC)=CC=1)OC1=CC=C(CCCCCCCCC)C=C1 MGMXGCZJYUCMGY-UHFFFAOYSA-N 0.000 description 15
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- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 5
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
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- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical group O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 3
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- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
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- 239000002530 phenolic antioxidant Substances 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- OBRKWFIGZSMARO-UHFFFAOYSA-N propylalumane Chemical compound [AlH2]CCC OBRKWFIGZSMARO-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001448 refractive index detection Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229920006301 statistical copolymer Polymers 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CMJCEVKJYRZMIA-UHFFFAOYSA-M thallium(i) iodide Chemical compound [Tl]I CMJCEVKJYRZMIA-UHFFFAOYSA-M 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- VALAJCQQJWINGW-UHFFFAOYSA-N tri(propan-2-yl)alumane Chemical compound CC(C)[Al](C(C)C)C(C)C VALAJCQQJWINGW-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- ZIYNWDQDHKSRCE-UHFFFAOYSA-N tricyclohexylalumane Chemical compound C1CCCCC1[Al](C1CCCCC1)C1CCCCC1 ZIYNWDQDHKSRCE-UHFFFAOYSA-N 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- JOJQVUCWSDRWJE-UHFFFAOYSA-N tripentylalumane Chemical compound CCCCC[Al](CCCCC)CCCCC JOJQVUCWSDRWJE-UHFFFAOYSA-N 0.000 description 1
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000004876 x-ray fluorescence Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc oxide Inorganic materials [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 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
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F10/04—Monomers containing three or four carbon atoms
- C08F10/08—Butenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
- C08C19/42—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups
- C08C19/44—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups of polymers containing metal atoms exclusively at one or both ends of the skeleton
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/28—Reaction with compounds containing carbon-to-carbon unsaturated bonds
-
- 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
- C08F136/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F136/02—Homopolymers 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
- C08F136/04—Homopolymers 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
- C08F136/06—Butadiene
-
- 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
- C08F6/00—Post-polymerisation treatments
- C08F6/06—Treatment of polymer solutions
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT002022A ITMI20042022A1 (it) | 2004-10-25 | 2004-10-25 | Processo per la preparazione di polibutadiene a basso grado di ramificazione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200508625B true ZA200508625B (en) | 2006-07-26 |
Family
ID=34956431
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200508625A ZA200508625B (en) | 2004-10-25 | 2005-10-24 | A process for the preparation of low branch content polybutadiene |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7112632B2 (ja) |
| EP (1) | EP1650227B1 (ja) |
| JP (1) | JP5014613B2 (ja) |
| KR (1) | KR101234499B1 (ja) |
| CN (1) | CN1831021B (ja) |
| AT (1) | ATE479711T1 (ja) |
| BR (1) | BRPI0504519B1 (ja) |
| CA (1) | CA2524017C (ja) |
| DE (1) | DE602005023250D1 (ja) |
| ES (1) | ES2351794T3 (ja) |
| IT (1) | ITMI20042022A1 (ja) |
| MX (1) | MXPA05011490A (ja) |
| PL (1) | PL1650227T3 (ja) |
| PT (1) | PT1650227E (ja) |
| TW (1) | TWI369367B (ja) |
| ZA (1) | ZA200508625B (ja) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102007038441A1 (de) * | 2007-08-16 | 2009-02-19 | Lanxess Deutschland Gmbh | Gekoppelte und Heteroatome enthaltende modifizierte Polymere auf Basis von konjugierten Dienen |
| ITMI20080570A1 (it) | 2008-04-02 | 2009-10-03 | Polimeri Europa Spa | Procedimento per la preparazione di polibutadiene ramificato ad alto contenuto in unita' 1,4-cis |
| DE102008053888A1 (de) * | 2008-10-30 | 2010-05-06 | Lanxess Deutschland Gmbh | Neues Verfahren zur Herstellung von Polybutadien-haltigen Formteilen |
| RU2442796C1 (ru) * | 2010-12-03 | 2012-02-20 | Открытое акционерное общество "Воронежский синтетический каучук" | Способ получения модифицированного 1,4-цис-полибутадиена |
| ITMI20120808A1 (it) * | 2012-05-11 | 2013-11-12 | Versalis Spa | "procedimento per la preparazione di polibutadiene ramificato ad alto contenuto in unita' 1,4-cis" |
| RU2500689C9 (ru) * | 2012-05-22 | 2014-02-20 | Открытое акционерное общество "Нижнекамскнефтехим" | Способ получения цис-1,4-полидиенов |
| RU2494116C1 (ru) * | 2012-05-22 | 2013-09-27 | Открытое акционерное общество "Нижнекамскнефтехим" | Способ получения бутадиеновых каучуков |
| EP2676968A1 (de) * | 2012-06-18 | 2013-12-25 | LANXESS Deutschland GmbH | Hoch Mooney NdBR mit Mooneysprung |
| CN103626926B (zh) * | 2012-08-21 | 2016-03-30 | 中国石油化工股份有限公司 | 一种聚丁二烯接枝异戊橡胶及其制备方法和硫化胶及混炼胶 |
| KR20160060562A (ko) | 2014-11-20 | 2016-05-30 | 주식회사 엘지화학 | 공액 디엔계 중합체 |
| KR101796360B1 (ko) | 2014-11-20 | 2017-11-09 | 주식회사 엘지화학 | 공액 디엔계 중합체의 제조방법 |
| EP3053934A1 (en) * | 2015-02-06 | 2016-08-10 | LANXESS Deutschland GmbH | Heteroatom containing modified diene polymers |
| US10179479B2 (en) | 2015-05-19 | 2019-01-15 | Bridgestone Americas Tire Operations, Llc | Plant oil-containing rubber compositions, tread thereof and race tires containing the tread |
| CN112292410B (zh) * | 2018-12-21 | 2023-09-19 | 株式会社Lg化学 | 改性共轭二烯类聚合物及其制备方法 |
| WO2021154112A1 (ru) | 2020-01-29 | 2021-08-05 | Публичное Акционерное Общество "Сибур Холдинг" (Пао "Сибур Холдинг") | Способ получения модифицированных полидиенов |
| WO2023276742A1 (ja) * | 2021-06-30 | 2023-01-05 | 株式会社クラレ | 共役ジエン系グラフト重合体及びその製造方法、潤滑油添加剤、粘度指数向上剤、摩擦抑制剤、並びに油組成物 |
| JPWO2023276741A1 (ja) * | 2021-06-30 | 2023-01-05 | ||
| WO2023193943A1 (en) * | 2022-04-08 | 2023-10-12 | Arlanxeo Deutschland Gmbh | Branched modified diene rubbers |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1191612B (it) * | 1985-05-15 | 1988-03-23 | Enichem Elastomers | Procedimento migliorato per la polimerizzazione o copolimerizzazione del butadiene |
| US4742085A (en) * | 1987-04-14 | 1988-05-03 | The B. F. Goodrich Company | Crosslinked porous skinless particles of PVC resin and process for producing same |
| IT1230756B (it) * | 1989-02-17 | 1991-10-29 | Enichem Elastomers | Metodo per la preparazione di polibutadiene a lavorabilita' migliorata. |
| JP3230532B2 (ja) * | 1991-08-28 | 2001-11-19 | 旭化成株式会社 | 共役ジエン系重合体の製造法 |
| DE4409861A1 (de) * | 1994-03-22 | 1995-09-28 | Sp Reifenwerke Gmbh | Kautschukmischung, daraus hergestellte Reifenlauffläche und Reifen mit dieser Reifenlauffläche |
| DE4436059A1 (de) | 1994-10-10 | 1996-04-11 | Bayer Ag | Verfahren zur Herstellung von mittels Nd-Katalysatoren polymerisierten Dienkautschuken mit niedrigem cold-flow und geringem Eigengeruch |
| US6242522B1 (en) * | 1998-03-24 | 2001-06-05 | Bridgestone Corporation | Rubber composition for tire tread and pneumatic tire using same |
| US6255416B1 (en) * | 1998-05-13 | 2001-07-03 | Jsr Corporation | Method of producing conjugated diene polymers |
| US6090926A (en) | 1998-06-05 | 2000-07-18 | Rhodia Rare Earths Inc. | Powdery, solid rare earth carboxylates with improved solubility in aliphatic solvents which are highly active catalysts in Ziegler-Natta systems |
| JP4367589B2 (ja) * | 1999-11-12 | 2009-11-18 | Ｊｓｒ株式会社 | 共役ジエン系重合体の製造方法およびゴム組成物 |
| JP4332690B2 (ja) * | 1999-11-12 | 2009-09-16 | Ｊｓｒ株式会社 | ゴム組成物 |
| CN1342719A (zh) * | 2001-10-12 | 2002-04-03 | 中国科学院长春应用化学研究所 | 稀土催化体系及其催化丁二烯顺式聚合工艺 |
| ITMI20012409A1 (it) * | 2001-11-15 | 2003-05-15 | Enichem Spa | Procedimento per la preparazione di polibutadiene 1,4-cis lineare oppure ramificato |
| ITMI20022711A1 (it) * | 2002-12-20 | 2004-06-21 | Polimeri Europa Spa | Procedimento per la preparazione di polidieni ramificati in presenza di catalizzatori a base di terre rare. |
| JP4273887B2 (ja) * | 2003-09-10 | 2009-06-03 | 日本ゼオン株式会社 | 変性共役ジエン重合体の製造方法 |
| ITMI20040076A1 (it) * | 2004-01-22 | 2004-04-22 | Polimeri Europa Spa | Procedimento per la preparazione di polibutadiene a basso grado di ranificazione |
-
2004
- 2004-10-25 IT IT002022A patent/ITMI20042022A1/it unknown
-
2005
- 2005-10-12 AT AT05109469T patent/ATE479711T1/de not_active IP Right Cessation
- 2005-10-12 PT PT05109469T patent/PT1650227E/pt unknown
- 2005-10-12 ES ES05109469T patent/ES2351794T3/es active Active
- 2005-10-12 PL PL05109469T patent/PL1650227T3/pl unknown
- 2005-10-12 DE DE602005023250T patent/DE602005023250D1/de active Active
- 2005-10-12 EP EP05109469A patent/EP1650227B1/en not_active Not-in-force
- 2005-10-17 US US11/250,383 patent/US7112632B2/en active Active
- 2005-10-17 CA CA2524017A patent/CA2524017C/en not_active Expired - Fee Related
- 2005-10-19 TW TW094136512A patent/TWI369367B/zh not_active IP Right Cessation
- 2005-10-20 BR BRPI0504519A patent/BRPI0504519B1/pt not_active IP Right Cessation
- 2005-10-21 KR KR1020050099755A patent/KR101234499B1/ko active IP Right Grant
- 2005-10-24 ZA ZA200508625A patent/ZA200508625B/en unknown
- 2005-10-25 MX MXPA05011490A patent/MXPA05011490A/es active IP Right Grant
- 2005-10-25 JP JP2005309663A patent/JP5014613B2/ja not_active Expired - Fee Related
- 2005-10-25 CN CN2005101217670A patent/CN1831021B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR101234499B1 (ko) | 2013-02-18 |
| JP5014613B2 (ja) | 2012-08-29 |
| CA2524017C (en) | 2012-08-07 |
| BRPI0504519A (pt) | 2006-06-27 |
| TWI369367B (en) | 2012-08-01 |
| DE602005023250D1 (de) | 2010-10-14 |
| ITMI20042022A1 (it) | 2005-01-25 |
| PL1650227T3 (pl) | 2011-02-28 |
| PT1650227E (pt) | 2010-12-03 |
| ATE479711T1 (de) | 2010-09-15 |
| EP1650227B1 (en) | 2010-09-01 |
| MXPA05011490A (es) | 2006-04-27 |
| CA2524017A1 (en) | 2006-04-25 |
| CN1831021B (zh) | 2011-10-05 |
| JP2006124707A (ja) | 2006-05-18 |
| TW200628501A (en) | 2006-08-16 |
| CN1831021A (zh) | 2006-09-13 |
| EP1650227A2 (en) | 2006-04-26 |
| US20060089472A1 (en) | 2006-04-27 |
| BRPI0504519B1 (pt) | 2016-09-13 |
| KR20060049136A (ko) | 2006-05-18 |
| EP1650227A3 (en) | 2006-05-10 |
| ES2351794T3 (es) | 2011-02-10 |
| US7112632B2 (en) | 2006-09-26 |
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