KR20090122435A - Ｅｄｄｎ을 사용하여 ｔｅｔａ를 제조하는 신규 방법 - Google Patents
Ｅｄｄｎ을 사용하여 ｔｅｔａ를 제조하는 신규 방법 Download PDFInfo
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- KR20090122435A KR20090122435A KR1020097018164A KR20097018164A KR20090122435A KR 20090122435 A KR20090122435 A KR 20090122435A KR 1020097018164 A KR1020097018164 A KR 1020097018164A KR 20097018164 A KR20097018164 A KR 20097018164A KR 20090122435 A KR20090122435 A KR 20090122435A
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- hydrogenation
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- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- GEIAQOFPUVMAGM-UHFFFAOYSA-N ZrO Inorganic materials [Zr]=O GEIAQOFPUVMAGM-UHFFFAOYSA-N 0.000 description 1
- CWVZGJORVTZXFW-UHFFFAOYSA-N [benzyl(dimethyl)silyl]methyl carbamate Chemical compound NC(=O)OC[Si](C)(C)CC1=CC=CC=C1 CWVZGJORVTZXFW-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 238000005275 alloying Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229910002056 binary alloy Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XNWKZBZIZGNODF-UHFFFAOYSA-N ethane-1,2-diamine propanenitrile Chemical compound C(CC)#N.C(CN)N XNWKZBZIZGNODF-UHFFFAOYSA-N 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- BSGRLBPZSRZQOR-UHFFFAOYSA-N ethene-1,1-diamine Chemical group NC(N)=C BSGRLBPZSRZQOR-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000011066 ex-situ storage Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002461 imidazolidines Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/48—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/20—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07103295.7 | 2007-03-01 | ||
| EP07103295 | 2007-03-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20090122435A true KR20090122435A (ko) | 2009-11-30 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020097018164A Withdrawn KR20090122435A (ko) | 2007-03-01 | 2008-02-28 | Ｅｄｄｎ을 사용하여 ｔｅｔａ를 제조하는 신규 방법 |
Country Status (7)
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|---|---|
| US (1) | US8299249B2 (https=) |
| EP (2) | EP2537835B1 (https=) |
| JP (1) | JP5415287B2 (https=) |
| KR (1) | KR20090122435A (https=) |
| CN (1) | CN101622224B (https=) |
| RU (1) | RU2472772C2 (https=) |
| WO (1) | WO2008104582A2 (https=) |
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| CN101675026A (zh) * | 2007-03-01 | 2010-03-17 | 巴斯夫欧洲公司 | 制备亚乙基胺混合物的方法 |
| JP5377335B2 (ja) * | 2007-03-01 | 2013-12-25 | ビーエーエスエフ ソシエタス・ヨーロピア | テトラエチレンペンタアミンの製造方法 |
| WO2008104553A1 (de) * | 2007-03-01 | 2008-09-04 | Basf Se | Verfahren zur herstellung von triethylentetraamin |
| CN102227413B (zh) | 2008-10-06 | 2014-11-05 | 联合碳化化学品及塑料技术公司 | 制备环状n-氨基官能化三胺的方法 |
| WO2010042161A1 (en) | 2008-10-06 | 2010-04-15 | Union Carbide Chemicals & Plastics Technology Llc | Low metal (nickel and rhenium) catalyst compositions including acidic mixed metal oxide as support |
| JP2012504610A (ja) | 2008-10-06 | 2012-02-23 | ユニオン カーバイド ケミカルズ アンド プラスティックス テクノロジー エルエルシー | エチレンアミンの製造方法 |
| CN102239002B (zh) | 2008-10-06 | 2013-10-30 | 联合碳化化学品及塑料技术公司 | 低金属负载的氧化铝载体的催化剂组合物和氨基化方法 |
| BRPI0922984B1 (pt) | 2008-12-19 | 2017-10-24 | Basf Se | Process for preparing pure triethanolamine |
| JP5431582B2 (ja) | 2009-06-18 | 2014-03-05 | ビーエーエスエフ ソシエタス・ヨーロピア | メチル置換ｔｅｔａ化合物 |
| US8766010B2 (en) | 2009-12-02 | 2014-07-01 | Basf Se | Method for distilling mixtures comprising ethylenediamine, N-methylethylenediamine, and water, and mixtures of ethylenediamine and N-methylethylenediamine having a low content of N-methylethylenediamine obtainable thereby |
| EP2542609A1 (en) * | 2010-03-02 | 2013-01-09 | Basf Se | The use of linear triethylentetramine as curing agent for epoxy resins |
| EP2557074A1 (en) * | 2011-08-11 | 2013-02-13 | Astellas Pharma Inc. | Process for the preparation of N,N,N',N'-tetrakis(3-aminopropyl)-1,4-butanediamine |
| CN103764614A (zh) * | 2011-08-31 | 2014-04-30 | 巴斯夫欧洲公司 | Eddn或edmn氢化反应出料的后处理方法 |
| WO2013030287A1 (de) | 2011-08-31 | 2013-03-07 | Basf Se | Verfahren zur herstellung von eddn und/oder edmn durch umsetzung von fach und eda |
| US20130053536A1 (en) * | 2011-08-31 | 2013-02-28 | Basf Se | Process for preparing eddn and/or edmn and a process for preparing deta and/or teta |
| US8952156B2 (en) | 2011-08-31 | 2015-02-10 | Basf Se | Process for working up reaction outputs from the hydrogenation of EDDN or EDMN |
| WO2013030259A1 (de) * | 2011-08-31 | 2013-03-07 | Basf Se | Verfahren zur herstellung von teta |
| WO2013030144A1 (de) * | 2011-08-31 | 2013-03-07 | Basf Se | Verfahren zur herstellung von eddn, edmn, teta und deta |
| US9012638B2 (en) | 2011-08-31 | 2015-04-21 | Basf Se | Process for preparing EDDN and/or EDMN by conversion of FACH and EDA |
| WO2013030249A1 (de) * | 2011-08-31 | 2013-03-07 | Basf Se | Verfahren zur herstellung von aminen durch hydrierung von nitrilen |
| WO2013030023A1 (de) * | 2011-08-31 | 2013-03-07 | Basf Se | Verfahren zur herstellung von eddn und/oder edmn sowie ein verfahren zur herstellung von deta und/oder teta |
| WO2013030254A1 (de) * | 2011-08-31 | 2013-03-07 | Basf Se | Verfahren zur herstellung von teta und/oder deta |
| IN2014CN00791A (https=) * | 2011-08-31 | 2015-04-03 | Basf Se | |
| US9096497B2 (en) | 2011-08-31 | 2015-08-04 | Basf Se | Process for preparing EDDN and EDMN |
| EP2751066A1 (de) * | 2011-08-31 | 2014-07-09 | Basf Se | Verfahren zur herstellung von edfa und/oder edmfa und deta und/oder teta |
| WO2013030255A1 (de) * | 2011-08-31 | 2013-03-07 | Basf Se | Verfahren zur herstellung von eddn und/oder edmn sowie verfahren zur herstellung von deta und/oder teta |
| JP2014525941A (ja) * | 2011-08-31 | 2014-10-02 | ビーエーエスエフ ソシエタス・ヨーロピア | Ｅｄｆａおよび／またはｅｄｍｆａとｈｃｎとの反応によりｅｄｄｎおよび／またはｅｄｍｎを製造する方法 |
| US8946459B2 (en) | 2011-08-31 | 2015-02-03 | Basf Se | Process for preparing EDDN and/or EDMN by reacting EDFA and/or EDMFA with HCN |
| EP3077444B1 (en) | 2013-12-02 | 2018-04-25 | Dow Global Technologies LLC | Preparation of high molecular weight, branched, acyclic polyalkyleneamines and mixtures thereof |
| US9888584B2 (en) | 2014-12-31 | 2018-02-06 | Invensas Corporation | Contact structures with porous networks for solder connections, and methods of fabricating same |
| JP6671490B2 (ja) | 2016-02-12 | 2020-03-25 | ヌーリオン ケミカルズ インターナショナル ベスローテン フェノーツハップＮｏｕｒｙｏｎ Ｃｈｅｍｉｃａｌｓ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｂ．Ｖ． | 高級エチレンアミンおよびエチレンアミン誘導体を調製する方法 |
| US10844001B2 (en) | 2016-02-12 | 2020-11-24 | Nouryon Chemicals International B.V. | Process to prepare higher ethylene amines and ethylene amine derivatives |
| MX378938B (es) | 2016-02-12 | 2025-03-10 | Akzo Nobel Chemicals Int Bv | Proceso para preparar etilenaminas y derivados de etilenaminas superiores. |
| KR102585829B1 (ko) * | 2017-07-10 | 2023-10-05 | 누리온 케미칼즈 인터내셔널 비.브이. | 고급 에틸렌아민 또는 이의 우레아 유도체의 제조 방법 |
| BR112020000020B1 (pt) | 2017-07-10 | 2023-10-17 | Nouryon Chemicals International B.V | Processo para preparar etileno aminas, derivado de ureia de tetraetileno pentamina, derivado de ureia de pentaetileno-hexamina e uso do derivado de ureia |
| CN111278801B (zh) | 2017-10-27 | 2023-05-26 | 巴斯夫欧洲公司 | 从含eda的混合物中分离n-甲基乙二胺 |
| JP7268016B2 (ja) | 2017-10-27 | 2023-05-02 | ビーエーエスエフ ソシエタス・ヨーロピア | エチレンアミンの製造方法 |
| JP7277454B2 (ja) | 2017-10-27 | 2023-05-19 | ビーエーエスエフ ソシエタス・ヨーロピア | エチレンアミンの製造方法 |
| CN111263746B (zh) | 2017-10-27 | 2024-01-19 | 巴斯夫欧洲公司 | 制备亚乙基胺的方法 |
| CN109490453A (zh) * | 2018-11-06 | 2019-03-19 | 广东省安全生产技术中心有限公司 | 一种三乙烯四胺的分离鉴定方法 |
| CN113924286A (zh) * | 2019-06-13 | 2022-01-11 | 陶氏环球技术有限责任公司 | 制备乙二胺四乙酸 |
| EP4073026B1 (en) | 2019-12-13 | 2024-06-05 | Basf Se | Separation of n-methylethylenediamine from eda-containing mixtures |
| KR20230091141A (ko) * | 2020-12-16 | 2023-06-22 | 누리온 케미칼즈 인터내셔널 비.브이. | 니트릴 화합물의 제조 |
| WO2024002740A1 (en) | 2022-06-29 | 2024-01-04 | Basf Se | Method for manufacture of ethyleneamines |
| JP2025520810A (ja) | 2022-06-29 | 2025-07-03 | ビーエーエスエフ ソシエタス・ヨーロピア | エチレンアミンの製造方法 |
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| ES2449066T3 (es) * | 2004-07-19 | 2014-03-18 | Philera New Zealand Limited | Síntesis de trietilentetraminas |
| WO2008104553A1 (de) * | 2007-03-01 | 2008-09-04 | Basf Se | Verfahren zur herstellung von triethylentetraamin |
| CN101675026A (zh) * | 2007-03-01 | 2010-03-17 | 巴斯夫欧洲公司 | 制备亚乙基胺混合物的方法 |
-
2008
- 2008-02-28 US US12/529,072 patent/US8299249B2/en not_active Expired - Fee Related
- 2008-02-28 JP JP2009551210A patent/JP5415287B2/ja not_active Expired - Fee Related
- 2008-02-28 RU RU2009136185/04A patent/RU2472772C2/ru not_active IP Right Cessation
- 2008-02-28 WO PCT/EP2008/052413 patent/WO2008104582A2/de not_active Ceased
- 2008-02-28 EP EP12183433.7A patent/EP2537835B1/de not_active Not-in-force
- 2008-02-28 EP EP08717210.2A patent/EP2129651B1/de not_active Not-in-force
- 2008-02-28 KR KR1020097018164A patent/KR20090122435A/ko not_active Withdrawn
- 2008-02-28 CN CN200880006798.3A patent/CN101622224B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP2537835B1 (de) | 2014-04-30 |
| CN101622224A (zh) | 2010-01-06 |
| WO2008104582A2 (de) | 2008-09-04 |
| RU2472772C2 (ru) | 2013-01-20 |
| WO2008104582A3 (de) | 2009-02-12 |
| EP2129651A2 (de) | 2009-12-09 |
| JP2010520170A (ja) | 2010-06-10 |
| CN101622224B (zh) | 2015-10-07 |
| US20100121064A1 (en) | 2010-05-13 |
| EP2537835A1 (de) | 2012-12-26 |
| RU2009136185A (ru) | 2011-04-10 |
| JP5415287B2 (ja) | 2014-02-12 |
| EP2129651B1 (de) | 2013-04-10 |
| US8299249B2 (en) | 2012-10-30 |
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