EP2049243A1 - Anlage und verfahren zur kontinuierlichen industriellen herstellung von organosilanen - Google Patents
Anlage und verfahren zur kontinuierlichen industriellen herstellung von organosilanenInfo
- Publication number
- EP2049243A1 EP2049243A1 EP07787231A EP07787231A EP2049243A1 EP 2049243 A1 EP2049243 A1 EP 2049243A1 EP 07787231 A EP07787231 A EP 07787231A EP 07787231 A EP07787231 A EP 07787231A EP 2049243 A1 EP2049243 A1 EP 2049243A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- reactor
- reaction
- catalyst
- units
- product
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 69
- 150000001282 organosilanes Chemical class 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 76
- 239000003054 catalyst Substances 0.000 claims abstract description 43
- 239000000376 reactant Substances 0.000 claims abstract description 17
- 238000010626 work up procedure Methods 0.000 claims abstract description 15
- 238000006459 hydrosilylation reaction Methods 0.000 claims abstract description 14
- -1 HSi compound Chemical class 0.000 claims abstract description 13
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- 229940126062 Compound A Drugs 0.000 claims abstract description 7
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- 239000010935 stainless steel Substances 0.000 claims description 27
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- 239000000203 mixture Substances 0.000 claims description 22
- 239000002815 homogeneous catalyst Substances 0.000 claims description 20
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- 238000009776 industrial production Methods 0.000 claims description 6
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 claims description 5
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- 239000003546 flue gas Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- RSKGMYDENCAJEN-UHFFFAOYSA-N hexadecyl(trimethoxy)silane Chemical compound CCCCCCCCCCCCCCCC[Si](OC)(OC)OC RSKGMYDENCAJEN-UHFFFAOYSA-N 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910000510 noble metal Inorganic materials 0.000 description 3
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- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
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- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 3
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- OYGYKEULCAINCL-UHFFFAOYSA-N triethoxy(hexadecyl)silane Chemical compound CCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC OYGYKEULCAINCL-UHFFFAOYSA-N 0.000 description 1
- 238000007514 turning Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/0093—Microreactors, e.g. miniaturised or microfabricated reactors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
- C07F7/14—Preparation thereof from optionally substituted halogenated silanes and hydrocarbons hydrosilylation reactions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00781—Aspects relating to microreactors
- B01J2219/00783—Laminate assemblies, i.e. the reactor comprising a stack of plates
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00781—Aspects relating to microreactors
- B01J2219/00788—Three-dimensional assemblies, i.e. the reactor comprising a form other than a stack of plates
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00781—Aspects relating to microreactors
- B01J2219/00819—Materials of construction
- B01J2219/00822—Metal
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00781—Aspects relating to microreactors
- B01J2219/00819—Materials of construction
- B01J2219/00824—Ceramic
- B01J2219/00826—Quartz
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00781—Aspects relating to microreactors
- B01J2219/00819—Materials of construction
- B01J2219/00831—Glass
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00781—Aspects relating to microreactors
- B01J2219/00819—Materials of construction
- B01J2219/00835—Comprising catalytically active material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00781—Aspects relating to microreactors
- B01J2219/00819—Materials of construction
- B01J2219/00837—Materials of construction comprising coatings other than catalytically active coatings
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00781—Aspects relating to microreactors
- B01J2219/00851—Additional features
- B01J2219/00858—Aspects relating to the size of the reactor
- B01J2219/0086—Dimensions of the flow channels
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00781—Aspects relating to microreactors
- B01J2219/00851—Additional features
- B01J2219/00867—Microreactors placed in series, on the same or on different supports
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00781—Aspects relating to microreactors
- B01J2219/00851—Additional features
- B01J2219/00869—Microreactors placed in parallel, on the same or on different supports
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00781—Aspects relating to microreactors
- B01J2219/00851—Additional features
- B01J2219/00871—Modular assembly
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00781—Aspects relating to microreactors
- B01J2219/00873—Heat exchange
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00781—Aspects relating to microreactors
- B01J2219/00889—Mixing
Definitions
- the present invention relates to a novel plant for the continuous industrial production of organosilanes by reacting an ⁇ , ß-unsaturated aliphatic, optionally substituted compound with a HSi compound and a related method.
- the present invention enables the preservation of process reliability in a comparatively simple and economical manner.
- a drastic process intensification in particular a shortening of the process time under reaction conditions by more than 99%, based on the space-time yield, compared to the standard batch process can be achieved.
- FIGS 1 to 6 are flow diagrams of plants or system parts as preferred Embodiments of the present invention can be seen.
- a reactor unit is understood as meaning an element of the multielement reactor (5), each element representing an area or reaction space for the said reaction, cf. for example, (5.1) (reactor unit in the form of a pre-reactor) in Figure 4 and (5.5) [reactor unit of an integrated block reactor (5.3)] in Figure 5 and (5.10) [reactor unit of a Mikrorohrbündel Anlagen (2004)erreaktors (5.9)].
- Reactor units of a multielement reactor (5) in the context of the present invention are in particular stainless steel or quartz glass capillaries, stainless steel tubes or well-dimensioned stainless steel reactors, for example pre-reactors (5.1), tubes (5.10) in microtube bundle heat exchanger reactors [e.g. B.
- reactor units whose respective reaction volume (also referred to as the reactor volume, ie the product of Cross-sectional area and structure length) 0.01 ml to 100 l, including all numerically intervening numerical values.
- the reactor volume of a reactor unit of a system according to the invention is particularly preferably 0.05 ml to 10 l, very particularly preferably 1 ml to 5 l, very particularly preferably 3 ml to 2 l, in particular 5 ml to 500 ml.
- Present multielement reactors (5) can advantageously be combined with a reactant component stream (4) or (5.2), which is suitably divided into the respective sub-streams, cf. z. B. (5.4) in Figure 5 and (5.11) in Figure 6, are fed.
- the product streams can be combined, cf. z. B. (5.7) in Figure 5, (5.12) in Figure 6 and (7), and then work up advantageously in a workup unit (8).
- a processing unit (8) initially have a condensation stage or evaporation stage, which optionally followed by one or more distillation stages.
- integrated block reactors (5.3) are advantageously surrounded by a temperature control unit (6.5, 6.6) which enables the heating or cooling of the block reactor (5.3), ie a targeted temperature control.
- a plant according to the invention for the continuous industrial implementation of reactions based on a Eduktzusammen arrangement (3) for the components A and B, at least one said multi-element reactor (5) and on a product work-up (8), cf.
- FIG. 1
- the multielement reactor (5) is preferably brought to or maintained at the desired operating temperature by means of a temperature control medium D (6.1, 6.2) so that undesirable temperature peaks and temperature fluctuations known from batch systems are advantageously avoided or adequately achieved in the present system according to the invention can become low.
- Another particularly noteworthy advantage of a plant according to the invention for the continuous industrial implementation of a reaction of ⁇ , ß-unsaturated compounds A with a HSi compound B is that it now has a Possibility to produce even small special products with sales volumes between 5 kg and 50 000 t pa, preferably 10 kg to 10 000 t pa, in a simple and economical way continuously and flexibly.
- unnecessary downtime, the yield, the selectivity influencing temperature peaks and fluctuations and too long residence times and thus unwanted side reactions can be advantageously avoided.
- such an installation can also be used optimally for the production of existing silanes from an economical, ecological and customer-friendly point of view.
- one carries out the reaction of the educt components A and B in at least one multi-element reactor, which in turn is based on at least two reactor units.
- reactor units which have a structure length of 1 cm to 200 m, particularly preferably 10 cm to 120 m, very particularly preferably 15 cm to 80 m, in particular 18 cm to 30 m, including all possible numerical values Be included above areas.
- R ' is a C 1 to C 4 alkyl group, preferably methyl, m is 0 or 1 and X is a hydrolyzable group, preferably chloride, methoxy, ethoxy.
- an activator for example in the form of an organic or inorganic acid such as HCl, H 2 SO 4 , H 3 PO 4 , mono- or dicarboxylic acids, HCOOH, H 3 C-COOH , Propionic acid, oxalic acid, succinic acid, Citric acid, benzoic acid, phthalic acid - just to name a few.
- an organic or inorganic acid such as HCl, H 2 SO 4 , H 3 PO 4 , mono- or dicarboxylic acids, HCOOH, H 3 C-COOH , Propionic acid, oxalic acid, succinic acid, Citric acid, benzoic acid, phthalic acid - just to name a few.
- solvents or diluents such as alcohols, aliphatic and aromatic hydrocarbons, CHC, CFC, ethers, esters, ketones - to name a few - can be used as auxiliaries.
- Such adjuvants can be removed from the product, for example, in the product work-up.
- the plant used for the continuous production of hexadecyltrimethoxysilane consisted essentially of the educt reservoirs, HPLC pumps, control, measuring and metering units, a T-mixer, a pre-reactor made of stainless steel (diameter 5 mm, length 40 mm), a stainless steel capillary ( Diameter 1 mm, length 50 m), a heat bath with temperature control for the temperature control of the pre-reactor and the capillary, a pressure-maintaining valve, a wiped Thin-film evaporator and connecting lines in the system for reactant feed between the abovementioned plant components as well as product, recycling and flue-gas removal.
- the resulting top product essentially TCS, could be used as recycling.
- Almost 0.5 kg of hydrosilylation product was withdrawn from the bottom of the stripping column per hour.
- fluoroalkyltrichlorosilane obtained can be reacted with an alcohol be reacted to obtain so advantageous fluoroalkylalkoxysilane.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102006037404 | 2006-08-10 | ||
DE102007023757A DE102007023757A1 (de) | 2006-08-10 | 2007-05-22 | Anlage und Verfahen zur kontinuierlichen industriellen Herstellung von Organosilanen |
PCT/EP2007/056955 WO2008017555A1 (de) | 2006-08-10 | 2007-07-09 | Anlage und verfahren zur kontinuierlichen industriellen herstellung von organosilanen |
Publications (1)
Publication Number | Publication Date |
---|---|
EP2049243A1 true EP2049243A1 (de) | 2009-04-22 |
Family
ID=38698184
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP07787231A Withdrawn EP2049243A1 (de) | 2006-08-10 | 2007-07-09 | Anlage und verfahren zur kontinuierlichen industriellen herstellung von organosilanen |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP2049243A1 (de) |
CN (1) | CN101362775B (de) |
DE (1) | DE102007023757A1 (de) |
WO (1) | WO2008017555A1 (de) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102007007185A1 (de) | 2007-02-09 | 2008-08-14 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Glycidyloxyalkyltrialkoxysilanen |
EP2360205A1 (de) | 2010-02-19 | 2011-08-24 | BYK-Chemie GmbH | Verfahren zur kontinuierlichen Hydrosilylierung |
GB201412406D0 (en) | 2014-07-11 | 2014-08-27 | Geo Speciality Chemicals Uk Ltd | Process |
CN105218573A (zh) * | 2015-09-30 | 2016-01-06 | 衢州氟硅技术研究院 | 一种用负载型铂催化剂制备全氟烷基乙基硅烷的方法及制备该负载型铂催化剂的方法 |
CN105693753B (zh) * | 2016-03-22 | 2019-04-26 | 南京曙光精细化工有限公司 | 利用通道反应装置制备有机硅的方法 |
CN109836449B (zh) * | 2017-11-29 | 2021-07-16 | 蓝星(北京)技术中心有限公司 | 一种有机硅单体合成方法及其生产装置 |
CN108383868A (zh) * | 2018-03-19 | 2018-08-10 | 张良敏 | 一种高品质γ-甲基丙烯酰氧基丙基三甲氧基硅烷的制备方法 |
CN109824713B (zh) * | 2019-03-05 | 2021-07-09 | 湖北江瀚新材料股份有限公司 | 一种长链烷基三烷氧基硅烷的制备方法 |
CN113861233B (zh) * | 2021-10-27 | 2023-07-25 | 湖北兴瑞硅材料有限公司 | 一种甲基三甲氧基硅烷的制备工艺及装置 |
CN114394991A (zh) * | 2022-01-27 | 2022-04-26 | 浙江锦华新材料股份有限公司 | 一种催化合成乙烯基三氯硅烷的方法 |
CN114940687A (zh) * | 2022-05-30 | 2022-08-26 | 杭州瀛拓科技有限公司 | 一种多取代乙烯基硅(氧)烷的连续流合成方法 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
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US5580523A (en) * | 1994-04-01 | 1996-12-03 | Bard; Allen J. | Integrated chemical synthesizers |
DE19858856A1 (de) * | 1998-12-19 | 2000-06-21 | Merck Patent Gmbh | Verfahren zur Herstellung von Arylmetallverbindungen und deren Umsetzung mit Elektrophilen |
DE19920794A1 (de) * | 1999-05-06 | 2000-11-09 | Merck Patent Gmbh | Verfahren zur Herstellung von Perlpolymerisaten |
DE19959249A1 (de) * | 1999-12-08 | 2001-07-19 | Inst Mikrotechnik Mainz Gmbh | Modulares Mikroreaktionssystem |
US7485454B1 (en) * | 2000-03-10 | 2009-02-03 | Bioprocessors Corp. | Microreactor |
DE10014298A1 (de) * | 2000-03-23 | 2001-09-27 | Merck Patent Gmbh | Verfahren zur Reduktion aliphatischer, aromatischer oder heterocyclischer organischer Verbindungen mittels Hydriden und/oder deren Derivaten |
DE10333174A1 (de) * | 2003-07-22 | 2005-02-17 | Cpc Cellular Process Chemistry Systems Gmbh | Verfahren zur Durchführung einer In-Situ-Quench Reaktion |
GB0413400D0 (en) * | 2004-06-16 | 2004-07-21 | Accentus Plc | Catalytic plant and process |
EP1805190A1 (de) * | 2004-10-28 | 2007-07-11 | Wacker Chemie AG | Herstellung von organosilanen in gegenwart von iridium-katalysatoren und cokatalysatoren |
-
2007
- 2007-05-22 DE DE102007023757A patent/DE102007023757A1/de not_active Withdrawn
- 2007-07-09 WO PCT/EP2007/056955 patent/WO2008017555A1/de active Application Filing
- 2007-07-09 EP EP07787231A patent/EP2049243A1/de not_active Withdrawn
- 2007-08-09 CN CN200710170168.7A patent/CN101362775B/zh not_active Expired - Fee Related
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Also Published As
Publication number | Publication date |
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CN101362775B (zh) | 2014-10-29 |
WO2008017555A1 (de) | 2008-02-14 |
DE102007023757A1 (de) | 2008-02-14 |
CN101362775A (zh) | 2009-02-11 |
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