JP5688091B2 - シーラントおよび接着剤において使用するための尿素結合型アルコキシシラン - Google Patents
シーラントおよび接着剤において使用するための尿素結合型アルコキシシラン Download PDFInfo
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- JP5688091B2 JP5688091B2 JP2012535866A JP2012535866A JP5688091B2 JP 5688091 B2 JP5688091 B2 JP 5688091B2 JP 2012535866 A JP2012535866 A JP 2012535866A JP 2012535866 A JP2012535866 A JP 2012535866A JP 5688091 B2 JP5688091 B2 JP 5688091B2
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- Prior art keywords
- diisocyanate
- carbon atoms
- group
- urea
- reactive
- 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.)
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- AQIHUSFQDQCINN-UHFFFAOYSA-N methyl(trimethoxysilylmethoxy)carbamic acid Chemical compound CN(C(=O)O)OC[Si](OC)(OC)OC AQIHUSFQDQCINN-UHFFFAOYSA-N 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
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- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- XCOASYLMDUQBHW-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)butan-1-amine Chemical compound CCCCNCCC[Si](OC)(OC)OC XCOASYLMDUQBHW-UHFFFAOYSA-N 0.000 description 1
- KGNDVXPHQJMHLX-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)cyclohexanamine Chemical compound CO[Si](OC)(OC)CCCNC1CCCCC1 KGNDVXPHQJMHLX-UHFFFAOYSA-N 0.000 description 1
- WUFHQGLVNNOXMP-UHFFFAOYSA-N n-(triethoxysilylmethyl)cyclohexanamine Chemical compound CCO[Si](OCC)(OCC)CNC1CCCCC1 WUFHQGLVNNOXMP-UHFFFAOYSA-N 0.000 description 1
- VNBLTKHUCJLFSB-UHFFFAOYSA-N n-(trimethoxysilylmethyl)aniline Chemical compound CO[Si](OC)(OC)CNC1=CC=CC=C1 VNBLTKHUCJLFSB-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- REODOQPOCJZARG-UHFFFAOYSA-N n-[[diethoxy(methyl)silyl]methyl]cyclohexanamine Chemical compound CCO[Si](C)(OCC)CNC1CCCCC1 REODOQPOCJZARG-UHFFFAOYSA-N 0.000 description 1
- WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- BARWIPMJPCRCTP-CLFAGFIQSA-N oleyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC BARWIPMJPCRCTP-CLFAGFIQSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UDKSLGIUCGAZTK-UHFFFAOYSA-N phenyl pentadecane-1-sulfonate Chemical compound CCCCCCCCCCCCCCCS(=O)(=O)OC1=CC=CC=C1 UDKSLGIUCGAZTK-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
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- 239000011118 polyvinyl acetate Substances 0.000 description 1
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- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
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- 239000002994 raw material Substances 0.000 description 1
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- JPPLPDOXWBVPCW-UHFFFAOYSA-N s-(3-triethoxysilylpropyl) octanethioate Chemical compound CCCCCCCC(=O)SCCC[Si](OCC)(OCC)OCC JPPLPDOXWBVPCW-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003329 sebacic acid derivatives Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000004526 silane-modified polyether Substances 0.000 description 1
- 239000004432 silane-modified polyurethane Substances 0.000 description 1
- 239000013467 silicone adhesive and sealant Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
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- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical class [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- UWSYCPWEBZRZNJ-UHFFFAOYSA-N trimethoxy(2,4,4-trimethylpentyl)silane Chemical compound CO[Si](OC)(OC)CC(C)CC(C)(C)C UWSYCPWEBZRZNJ-UHFFFAOYSA-N 0.000 description 1
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- YJUIKPXYIJCUQP-UHFFFAOYSA-N trizinc;iron(3+);dodecacyanide Chemical compound [Fe+3].[Fe+3].[Zn+2].[Zn+2].[Zn+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] YJUIKPXYIJCUQP-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
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- 239000008096 xylene Substances 0.000 description 1
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- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4866—Polyethers having a low unsaturation value
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
- C09J171/02—Polyalkylene oxides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/08—Polyurethanes from polyethers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Polyurethanes Or Polyureas (AREA)
- Sealing Material Composition (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102009046269A DE102009046269A1 (de) | 2009-10-30 | 2009-10-30 | Harnstoffgebundende Alkoxysilane zum Einsatz in Dicht- und Klebstoffen |
| DE102009046269.4 | 2009-10-30 | ||
| PCT/EP2010/066592 WO2011051491A1 (de) | 2009-10-30 | 2010-11-02 | Harnstoffgebundende alkoxysilane zum einsatz in dicht- und klebstoffen |
Publications (3)
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| JP2013509476A JP2013509476A (ja) | 2013-03-14 |
| JP2013509476A5 JP2013509476A5 (enExample) | 2013-12-19 |
| JP5688091B2 true JP5688091B2 (ja) | 2015-03-25 |
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| DE (1) | DE102009046269A1 (enExample) |
| ES (1) | ES2435633T3 (enExample) |
| PL (1) | PL2493957T3 (enExample) |
| WO (1) | WO2011051491A1 (enExample) |
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| DE102010001470A1 (de) * | 2010-02-02 | 2011-08-04 | Henkel AG & Co. KGaA, 40589 | Polyetherblockcopolymere und daraus erhältliche Zusammensetzungen |
| JP5584575B2 (ja) * | 2010-09-30 | 2014-09-03 | 株式会社カネカ | プライマー組成物 |
| TWI575049B (zh) * | 2011-12-22 | 2017-03-21 | 漢高股份有限公司 | 紫外線硬化型和濕氣硬化型黏膠組成物 |
| CN102604071B (zh) * | 2012-03-01 | 2013-12-04 | 西北工业大学 | 端羟基聚丁二烯-聚四氢呋喃三嵌段共聚物及其制备方法 |
| CN103045056A (zh) * | 2012-12-12 | 2013-04-17 | 优利康达（天津）科技有限公司 | 一种高耐候性的不饱和树脂涂层封闭剂及使用方法 |
| US9765247B2 (en) | 2013-09-11 | 2017-09-19 | Dow Global Technologies Llc | Silyl terminated prepolymers, method for making them and adhesive compositions made therefrom |
| CA2933163A1 (en) * | 2013-09-30 | 2015-04-02 | Virginia Commonwealth University | Ice release coatings |
| CN103694709B (zh) * | 2013-12-09 | 2016-04-13 | 华南理工大学 | 加成型液体硅橡胶用耐漏电起痕剂及其制备方法和应用 |
| US9920199B2 (en) | 2014-09-02 | 2018-03-20 | Dow Global Technologies Llc | Silyl terminated prepolymers, method for making them and adhesive compositions made therefrom |
| CN104559916B (zh) * | 2015-01-16 | 2016-09-21 | 北京天山新材料技术有限公司 | 一种食品安全的加成型硅橡胶密封剂及其制备方法 |
| CN105348507A (zh) * | 2015-12-04 | 2016-02-24 | 西北工业大学 | 窄分布的高1，4结构端羟基聚丁二烯-聚四氢呋喃三嵌段共聚物及制备方法 |
| ES2896477T3 (es) | 2016-10-14 | 2022-02-24 | Basf Se | Composición estabilizante |
| CN110062796B (zh) | 2016-10-14 | 2021-09-03 | 巴斯夫欧洲公司 | 可硬化的聚合物组合物 |
| JP2021522382A (ja) * | 2018-04-25 | 2021-08-30 | ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェンＨｅｎｋｅｌ ＡＧ ＆ Ｃｏ． ＫＧａＡ | ヒドロキシル官能化ポリエーテルポリシロキサンブロックコポリマーの調製用プロセス |
| EP3613785A1 (de) * | 2018-08-21 | 2020-02-26 | Covestro Deutschland AG | Trocknungsmittel für feuchtigkeitshärtende zusammensetzungen |
| CN111117489B (zh) * | 2018-10-31 | 2022-01-07 | 娄从江 | 一种快速成膜和高阻隔性硅烷改性类建筑密封胶的底涂剂 |
| US20220073821A1 (en) | 2019-01-16 | 2022-03-10 | Basf Se | Stabilizer composition for sealants and adhesives |
| EP3715396A1 (de) | 2019-03-26 | 2020-09-30 | PolyU GmbH | Zusammensetzung und verfahren zur herstellung silylierter polymere und deren verwendung |
| SE1950486A1 (en) * | 2019-04-17 | 2020-10-18 | Essve Produkter Ab | Adhesive sealant composition |
| FR3102481B1 (fr) * | 2019-10-24 | 2021-10-01 | Bostik Sa | Copolyurethane silyle ionique et composition de mastic le comprenant |
| CN111154445B (zh) * | 2020-01-17 | 2021-03-19 | 杭州之江新材料有限公司 | 一种双组份防水密封胶 |
| US20230183425A1 (en) * | 2021-12-10 | 2023-06-15 | Thanikaivelan Tindivanam Veeraraghavan | Two-component moisture curable thermal interface material for thermal management systems |
| CN114479741B (zh) * | 2022-02-23 | 2023-03-31 | 广州市白云化工实业有限公司 | 一种低温可快速深层固化的单组分有机硅改性密封胶及其制备方法 |
| CN114686082B (zh) * | 2022-05-09 | 2022-10-11 | 上海予通管道工程技术有限公司 | 一种用于管道修复的耐腐蚀聚脲涂料及其制备方法 |
| CN116144013B (zh) * | 2023-02-15 | 2025-02-11 | 西安近代化学研究所 | 一种端四烯基聚醚粘合剂及其合成方法 |
| CN119751894B (zh) * | 2024-12-17 | 2025-11-04 | 广州白云科技股份有限公司 | 硅烷改性聚醚-聚丁二烯、透明耐水解的硅烷改性聚醚密封胶及其制备方法 |
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-
2009
- 2009-10-30 DE DE102009046269A patent/DE102009046269A1/de not_active Ceased
-
2010
- 2010-11-02 WO PCT/EP2010/066592 patent/WO2011051491A1/de not_active Ceased
- 2010-11-02 PL PL10771480T patent/PL2493957T3/pl unknown
- 2010-11-02 JP JP2012535866A patent/JP5688091B2/ja not_active Expired - Fee Related
- 2010-11-02 ES ES10771480T patent/ES2435633T3/es active Active
- 2010-11-02 EP EP10771480.0A patent/EP2493957B1/de active Active
- 2010-11-02 CN CN201080048663.0A patent/CN102666648B/zh not_active Expired - Fee Related
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Also Published As
| Publication number | Publication date |
|---|---|
| ES2435633T3 (es) | 2013-12-20 |
| DE102009046269A1 (de) | 2011-05-05 |
| PL2493957T3 (pl) | 2014-02-28 |
| EP2493957A1 (de) | 2012-09-05 |
| CN102666648B (zh) | 2014-06-04 |
| US20120238695A1 (en) | 2012-09-20 |
| CN102666648A (zh) | 2012-09-12 |
| US8501903B2 (en) | 2013-08-06 |
| EP2493957B1 (de) | 2013-09-11 |
| JP2013509476A (ja) | 2013-03-14 |
| WO2011051491A1 (de) | 2011-05-05 |
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