RU2008114500A - Блок-сополимеры каталитической полимеризации олефинов с контролируемым распределением последовательности блоков - Google Patents
Блок-сополимеры каталитической полимеризации олефинов с контролируемым распределением последовательности блоков Download PDFInfo
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- RU2008114500A RU2008114500A RU2008114500/04A RU2008114500A RU2008114500A RU 2008114500 A RU2008114500 A RU 2008114500A RU 2008114500/04 A RU2008114500/04 A RU 2008114500/04A RU 2008114500 A RU2008114500 A RU 2008114500A RU 2008114500 A RU2008114500 A RU 2008114500A
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- 238000006116 polymerization reaction Methods 0.000 title claims abstract 7
- 150000001336 alkenes Chemical class 0.000 title claims abstract 3
- 229920001400 block copolymer Polymers 0.000 title 1
- 230000003197 catalytic effect Effects 0.000 title 1
- 239000000178 monomer Substances 0.000 claims abstract 12
- 229920000642 polymer Polymers 0.000 claims abstract 11
- 238000000034 method Methods 0.000 claims abstract 10
- 239000000203 mixture Substances 0.000 claims abstract 6
- 229920001577 copolymer Polymers 0.000 claims abstract 5
- 239000003054 catalyst Substances 0.000 claims abstract 4
- 239000011541 reaction mixture Substances 0.000 claims abstract 4
- 230000015572 biosynthetic process Effects 0.000 claims abstract 3
- 239000012986 chain transfer agent Substances 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract 2
- 230000000704 physical effect Effects 0.000 claims abstract 2
- 239000002685 polymerization catalyst Substances 0.000 claims abstract 2
- 239000000126 substance Substances 0.000 claims abstract 2
- 125000004429 atom Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 150000004696 coordination complex Chemical class 0.000 claims 2
- 239000003446 ligand Substances 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- 229920002959 polymer blend Polymers 0.000 claims 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical class [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000000129 anionic group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004404 heteroalkyl group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 229920000592 inorganic polymer Polymers 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 150000007527 lewis bases Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000325 methylidene group Chemical class [H]C([H])=* 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 229920000620 organic polymer Polymers 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 230000000737 periodic effect Effects 0.000 claims 1
- 125000002743 phosphorus functional group Chemical group 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 230000000638 stimulation Effects 0.000 claims 1
- 238000012644 addition polymerization Methods 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 230000004936 stimulating effect Effects 0.000 abstract 1
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/06—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the coordination type
- C08F297/08—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the coordination type polymerising mono-olefins
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- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/01—Processes of polymerisation characterised by special features of the polymerisation apparatus used
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- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/16—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/02—Carriers therefor
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- 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/04—Monomers containing three or four carbon atoms
- C08F210/06—Propene
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- 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
- C08F2410/00—Features related to the catalyst preparation, the catalyst use or to the deactivation of the catalyst
- C08F2410/01—Additive used together with the catalyst, excluding compounds containing Al or B
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65908—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an ionising compound other than alumoxane, e.g. (C6F5)4B-X+
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- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/6592—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/6592—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
- C08F4/65922—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not
- C08F4/65927—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not two cyclopentadienyl rings being mutually bridged
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- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Graft Or Block Polymers (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
1. Способ полимеризации одного или нескольких способных к полимеризации присоединением мономеров с получением сополимера, содержащего две области или два сегмента с отличающимся полимерным составом или свойствами, указанный способ включает: ! 1) введение в контакт способного к полимеризации присоединением мономера или смеси мономеров в условиях полимеризации присоединением в реакторе или в зоне реактора с композицией, содержащей, по меньшей мере, один катализатор полимеризации олефинов и сокатализатор, и характеризующееся образованием полимерных цепочек из указанного мономера или мономеров; ! 2) перемещение реакционной смеси во второй реактор или зону реактора и необязательно добавление одного или нескольких дополнительных реагентов, катализаторов, мономеров или других соединений до, одновременно с или после указанного перемещения; и ! 3) стимулирование протекания полимеризации в указанном втором реакторе или зоне реактора с образованием полимерных цепочек, которые отличаются от полимерных цепочек, образованных на стадии 1); ! причем указанный способ характеризуется добавлением агента переноса цепи к реакционной смеси до, во время или после стадии 1) так, что, по меньшей мере, некоторые из молекул полученного полимера со стадии 3) содержат два или несколько химически или физически различаемых блоков или сегментов. ! 2. Высокомолекулярный сополимер, содержащий два или несколько, по существу, гомогенных внутримолекулярных сегментов или блоков, имеющих отличающиеся химические или физические свойства, причем указанные внутримолекулярные сегменты характеризуются наличием наиболее вероятного молекулярно-
Claims (7)
1. Способ полимеризации одного или нескольких способных к полимеризации присоединением мономеров с получением сополимера, содержащего две области или два сегмента с отличающимся полимерным составом или свойствами, указанный способ включает:
1) введение в контакт способного к полимеризации присоединением мономера или смеси мономеров в условиях полимеризации присоединением в реакторе или в зоне реактора с композицией, содержащей, по меньшей мере, один катализатор полимеризации олефинов и сокатализатор, и характеризующееся образованием полимерных цепочек из указанного мономера или мономеров;
2) перемещение реакционной смеси во второй реактор или зону реактора и необязательно добавление одного или нескольких дополнительных реагентов, катализаторов, мономеров или других соединений до, одновременно с или после указанного перемещения; и
3) стимулирование протекания полимеризации в указанном втором реакторе или зоне реактора с образованием полимерных цепочек, которые отличаются от полимерных цепочек, образованных на стадии 1);
причем указанный способ характеризуется добавлением агента переноса цепи к реакционной смеси до, во время или после стадии 1) так, что, по меньшей мере, некоторые из молекул полученного полимера со стадии 3) содержат два или несколько химически или физически различаемых блоков или сегментов.
2. Высокомолекулярный сополимер, содержащий два или несколько, по существу, гомогенных внутримолекулярных сегментов или блоков, имеющих отличающиеся химические или физические свойства, причем указанные внутримолекулярные сегменты характеризуются наличием наиболее вероятного молекулярно-массового распределения.
3. Полимерная смесь, содержащая: (1) органический или неорганический полимер, и (2) сополимер по п.2 или получаемый по п.1.
4. Способ по п.1, где катализатор содержит комплекс металла, соответствующий формуле:
где R11 выбирают из алкила, циклоалкила, гетероалкила, циклогетероалкила и их инертно замещенных производных, содержащих от 1 до 30 атомов, не считая атомов водорода, или их двухвалентных производных;
Т1 представляет собой двухвалентную мостиковую группу, содержащую от 1 до 41 атома, отличных от атомов водорода, предпочтительно от 1 до 20 атомов, отличных от атомов водорода, и наиболее предпочтительно моно- или ди-С1-20-гидрокарбил-замещенную метиленовую или силановую группу; и
R12 представляет собой С5-20-гетероарильную группу, содержащую функциональность основания Льюиса;
М1 представляет собой металл 4 группы;
Х1 представляет собой анионную, нейтральную или дианионную лигандную группу;
x' представляет собой число от 0 до 5, указывающее на число таких групп Х1; и
связи, необязательные связи и предоставляющие электрон взаимодействия представлены линиями, пунктирными линиями и стрелками соответственно.
5. Способ по п.1, где катализатор содержит комплекс металла, соответствующий формуле:
где М2 представляет собой металл 4-10 групп Периодической таблицы элементов;
Т2 представляет собой азот-, кислород- или фосфорсодержащую группу;
Х2 представляет собой атом галогена, гидрокарбил или гидрокарбилоксигруппу;
t равно одному или двум;
х” представляет собой число, выбранное, чтобы обеспечить баланс зарядов; и
Т2 и N соединены с помощью мостикового лиганда.
6. Способ по любому из пп.1, 4 или 5, отличающийся производством полимера по п. 2 или полимерной смеси по п.3.
7. Способ по любому из пп.1, 4 или 5, где химически или физически отличающиеся блоки или сегменты имеют различные показатели введения сомономеров.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71754505P | 2005-09-15 | 2005-09-15 | |
| US60/717,545 | 2005-09-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2008114500A true RU2008114500A (ru) | 2009-10-20 |
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| RU2008114500/04A RU2008114500A (ru) | 2005-09-15 | 2006-09-14 | Блок-сополимеры каталитической полимеризации олефинов с контролируемым распределением последовательности блоков |
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| Country | Link |
|---|---|
| US (1) | US8053529B2 (ru) |
| EP (1) | EP1926763B1 (ru) |
| JP (2) | JP6138408B2 (ru) |
| KR (2) | KR101519805B1 (ru) |
| CN (1) | CN101309943B (ru) |
| AR (1) | AR058450A1 (ru) |
| BR (1) | BRPI0617001B1 (ru) |
| CA (1) | CA2622711A1 (ru) |
| MX (1) | MX2008003618A (ru) |
| MY (1) | MY157940A (ru) |
| RU (1) | RU2008114500A (ru) |
| TW (1) | TWI426089B (ru) |
| WO (1) | WO2007035485A1 (ru) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| ZA200804595B (en) * | 2005-12-09 | 2009-08-26 | Dow Global Technologies Inc | Processes of controlling molecular weight distribution in ethylene/alpha-olefin compositions |
| US8153243B2 (en) | 2005-12-09 | 2012-04-10 | Dow Global Technologies Llc | Interpolymers suitable for multilayer films |
| JP5996162B2 (ja) * | 2007-07-13 | 2016-09-21 | ダウ グローバル テクノロジーズ エルエルシー | 制御されたブロック配列分布及び少なくとも一つの低結晶性ハードブロックを有する触媒オレフィンブロックコポリマー |
| EP2170604B1 (en) * | 2007-07-13 | 2019-05-15 | Dow Global Technologies LLC | Ethylene/alpha-olefin interpolymers having low crystallinity hard blocks |
| WO2009012153A1 (en) * | 2007-07-13 | 2009-01-22 | Dow Global Technologies Inc. | Viscosity index improver for lubricant compositions |
| TW200936619A (en) * | 2007-11-15 | 2009-09-01 | Univation Tech Llc | Polymerization catalysts, methods of making, methods of using, and polyolefin products made therefrom |
| US8835577B2 (en) | 2007-11-15 | 2014-09-16 | Univation Technologies, Llc | Catalyst systems having a tailored hydrogen response |
| KR101669683B1 (ko) * | 2008-01-30 | 2016-10-27 | 다우 글로벌 테크놀로지스 엘엘씨 | 프로필렌/α-올레핀 블록 혼성중합체 |
| WO2009097565A1 (en) * | 2008-01-30 | 2009-08-06 | Dow Global Technologies Inc. | ETHYLENE/α-OLEFIN BLOCK INTERPOLYMERS |
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| CN116640276B (zh) * | 2023-06-27 | 2024-01-26 | 天津大学 | 一种序列可控多嵌段共聚物刷的合成方法 |
| WO2025072678A1 (en) | 2023-09-29 | 2025-04-03 | Dow Global Technologies Llc | Process for preparing an olefin-acrylate block copolymer |
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| EP4596231A1 (en) | 2024-01-31 | 2025-08-06 | Dow Global Technologies LLC | Tie layers comprising crystalline block composite components and functionalized polyethylene and multilayer films incorporating same |
| WO2026015705A1 (en) | 2024-07-11 | 2026-01-15 | Dow Global Technologies Llc | Crosslinkable polymer compositions with propylene-based polymer and reversible crosslinker |
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| US4284738A (en) | 1980-08-11 | 1981-08-18 | El Paso Polyolefins Company | Ethylene-propylene block copolymerization process and product |
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| US6576306B2 (en) * | 1996-09-04 | 2003-06-10 | Exxonmobil Chemical Patents Inc. | Propylene polymers for films |
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| US6124400A (en) | 1998-09-10 | 2000-09-26 | Academy Of Applied Science | Semicrystalline polymer alloy and process for preparation |
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| JP4487226B2 (ja) * | 2000-04-26 | 2010-06-23 | チッソ株式会社 | プロピレン／オレフィン・ブロック共重合体 |
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| JP4745541B2 (ja) | 2001-06-18 | 2011-08-10 | 日本ポリプロ株式会社 | プロピレンブロック共重合体の製造方法 |
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| WO2004044013A1 (ja) * | 2002-11-14 | 2004-05-27 | Idemitsu Kosan Co., Ltd. | プロピレンーエチレンブロック共重合体の製造方法及びプロピレンーエチレンブロック共重合体 |
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| CN1934150A (zh) * | 2004-03-17 | 2007-03-21 | 陶氏环球技术公司 | 用于形成乙烯共聚物的包括穿梭剂的催化剂组合物 |
| US7858706B2 (en) * | 2004-03-17 | 2010-12-28 | Dow Global Technologies Inc. | Catalyst composition comprising shuttling agent for ethylene multi-block copolymer formation |
| SG151302A1 (en) * | 2004-03-17 | 2009-04-30 | Dow Global Technologies Inc | Catalyst composition comprising shuttling agent for higher olefin multi- block copolymer formation |
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2006
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- 2006-09-14 AR ARP060104034A patent/AR058450A1/es unknown
- 2006-09-14 MY MYPI20080719A patent/MY157940A/en unknown
- 2006-09-14 TW TW095134018A patent/TWI426089B/zh not_active IP Right Cessation
- 2006-09-14 JP JP2008531356A patent/JP6138408B2/ja active Active
- 2006-09-14 CA CA002622711A patent/CA2622711A1/en not_active Abandoned
- 2006-09-14 EP EP06814741.2A patent/EP1926763B1/en active Active
- 2006-09-14 BR BRPI0617001-3A patent/BRPI0617001B1/pt active IP Right Grant
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- 2006-09-14 US US12/066,879 patent/US8053529B2/en active Active
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- 2006-09-14 RU RU2008114500/04A patent/RU2008114500A/ru not_active Application Discontinuation
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2008
- 2008-04-14 KR KR1020087008832A patent/KR101472143B1/ko active Active
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| Publication number | Publication date |
|---|---|
| KR20080056206A (ko) | 2008-06-20 |
| AR058450A1 (es) | 2008-02-06 |
| KR101472143B1 (ko) | 2014-12-12 |
| EP1926763A1 (en) | 2008-06-04 |
| JP6138408B2 (ja) | 2017-05-31 |
| BRPI0617001B1 (pt) | 2018-02-14 |
| MY157940A (en) | 2016-08-15 |
| WO2007035485A1 (en) | 2007-03-29 |
| CN101309943B (zh) | 2012-09-26 |
| TW200714619A (en) | 2007-04-16 |
| EP1926763B1 (en) | 2014-10-29 |
| KR20140043507A (ko) | 2014-04-09 |
| US20080269412A1 (en) | 2008-10-30 |
| JP2015206047A (ja) | 2015-11-19 |
| WO2007035485A9 (en) | 2008-06-26 |
| JP2009509001A (ja) | 2009-03-05 |
| KR101519805B1 (ko) | 2015-05-12 |
| CA2622711A1 (en) | 2007-03-29 |
| CN101309943A (zh) | 2008-11-19 |
| MX2008003618A (es) | 2008-10-07 |
| TWI426089B (zh) | 2014-02-11 |
| US8053529B2 (en) | 2011-11-08 |
| BRPI0617001A2 (pt) | 2011-07-05 |
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