JP2012510440A - N−ビニルアミドから副生成物を除去する方法 - Google Patents
N−ビニルアミドから副生成物を除去する方法 Download PDFInfo
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- JP2012510440A JP2012510440A JP2011537923A JP2011537923A JP2012510440A JP 2012510440 A JP2012510440 A JP 2012510440A JP 2011537923 A JP2011537923 A JP 2011537923A JP 2011537923 A JP2011537923 A JP 2011537923A JP 2012510440 A JP2012510440 A JP 2012510440A
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- Prior art keywords
- crude
- vinylamide
- vinylpyrrolidone
- extraction
- column
- 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.)
- Granted
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- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 title claims abstract description 43
- 238000000034 method Methods 0.000 title claims abstract description 27
- 239000006227 byproduct Substances 0.000 title claims abstract description 20
- 238000000605 extraction Methods 0.000 claims abstract description 40
- 239000000203 mixture Substances 0.000 claims abstract description 37
- 239000000047 product Substances 0.000 claims abstract description 15
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 47
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- -1 vinyl lactam Chemical class 0.000 claims description 9
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 6
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- 238000010626 work up procedure Methods 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 claims description 3
- KNQXLXOGOKJNCS-UHFFFAOYSA-N 1-but-3-enylpyrrolidin-2-one Chemical compound C=CCCN1CCCC1=O KNQXLXOGOKJNCS-UHFFFAOYSA-N 0.000 claims description 2
- JHYYINIEKJKMDD-UHFFFAOYSA-N 1-ethenyl-3,3-dimethylpyrrolidin-2-one Chemical compound CC1(C)CCN(C=C)C1=O JHYYINIEKJKMDD-UHFFFAOYSA-N 0.000 claims description 2
- PBGPBHYPCGDFEZ-UHFFFAOYSA-N 1-ethenylpiperidin-2-one Chemical group C=CN1CCCCC1=O PBGPBHYPCGDFEZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 claims description 2
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 claims description 2
- DHERNFAJQNHYBM-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1.O=C1CCCN1 DHERNFAJQNHYBM-UHFFFAOYSA-N 0.000 claims description 2
- 125000002015 acyclic group Chemical group 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- DURRSEGFTCZKMK-UHFFFAOYSA-N 1-prop-2-enylpyrrolidin-2-one Chemical compound C=CCN1CCCC1=O DURRSEGFTCZKMK-UHFFFAOYSA-N 0.000 claims 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 6
- 239000003849 aromatic solvent Substances 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- WDQFELCEOPFLCZ-UHFFFAOYSA-N 1-(2-hydroxyethyl)pyrrolidin-2-one Chemical compound OCCN1CCCC1=O WDQFELCEOPFLCZ-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000010587 phase diagram Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/09—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
- C07D201/16—Separation or purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Extraction Or Liquid Replacement (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Description
抽出に際して、有機溶媒が抽出剤として使用される。
全般的に、粗N−ビニルアミドの抽出のためにも、標準圧力(1bar)下で20〜100℃の温度範囲が適している。抽出は、高められた圧力又は減圧でも実施されることができる。抽出剤は、例えば、粗N−ビニルピロリドン1質量部について、20〜0.5質量部の量で、殊に10〜1質量部の量で使用されることができる。
N−ビニルピロリドンを、アセチレンと2−ピロリドンとの反応によって製造した。得られた混合物から、高沸点物を蒸留によって分離した。塔頂生成物として、なお蛍光性不純物を含有するN−ビニルピロリドンが得られるこれを、粗N−ビニルピロリドンとして、後続の抽出試験にて使用した。
F=F 粗NVP/F 抽出NVP。
Claims (17)
- N−ビニルアミドに富んだ生成物混合物(粗N−ビニルアミド)から副生成物を分離する方法において、前記粗N−ビニルアミドの抽出を、抽出剤としての有機溶媒を用いて実施することを特徴とする方法。
- 前記式Iの非環状N−ビニルアミドが、N−ビニルホルムアミド(R1及びR2=H)又はN−ビニル−N−メチルアセトアミド(VIMA、R1及びR2=メチル)であることを特徴とする、請求項1又は2記載の方法。
- 前記環状N−ビニルアミドが、N−ビニルピペリドン、N−ビニルカプロラクタム又はN−ビニルピロリドン又はこれらの誘導体、例えばN−ビニルメチルピロリドン、N−ビニルジメチルピロリドン又はN−ビニルエチルピロリドンであることを特徴とする、請求項1又は2記載の方法。
- 前記N−ビニルアミドがN−ビニルピロリドンであることを特徴とする、請求項1から4までのいずれか1項記載の方法。
- 前記粗N−ビニルアミドが、少なくとも50質量%でN−ビニルアミドから成ることを特徴とする、請求項1から5までのいずれか1項記載の方法。
- 前記粗N−ビニルアミドを、出発物質とアセチレンとの反応及び場合により引き続く後処理によって得たことを特徴とする、請求項1から6までのいずれか1項記載の方法。
- 前記粗N−ビニルアミドが、2−ピロリドン(γ−ブチロラクタム)とアセチレンとの反応及び場合により引き続く後処理によって得られた粗N−ビニルピロリドンであることを特徴とする、請求項1から7までのいずれか1項記載の方法。
- 前記抽出前に、粗N−ビニルアミドから高沸点物を分離するために蒸留(粗蒸留)を実施することを特徴とする、請求項1から8までのいずれか1項記載の方法。
- 脂肪族溶媒又は脂環式溶媒を使用することを特徴とする、請求項1から9までのいずれか1項記載の方法。
- 抽出を水の添加下で行うことを特徴とする、請求項1から10までのいずれか1項記載の方法。
- 粗N−ビニルピロリドンを、メチルシクロヘキサンにより、水の添加下で抽出することを特徴とする、請求項1から11までのいずれか1項記載の方法。
- 前記抽出を、20〜100℃の温度範囲で実施することを特徴とする、請求項1から12までのいずれか1項記載の方法。
- 前記抽出を、連続的に1つ又は複数の塔中で実施することを特徴とする、請求項1から13までのいずれか1項記載の方法。
- 粗N−ビニルピロリドンを、メチルシクロヘキサンにより、水の添加下で連続的に塔中で抽出し、その際、水を、分配器を介して前記塔の上部に、メチルシクロヘキサンを、分配器を介して前記塔の下部に、かつ前記粗N−ビニルピロリドンを、前記塔の中間部に送り込むことを特徴とする、請求項1から14までのいずれか1項記載の方法。
- 前記塔の頂部で、メチルシクロヘキサンと、分離された副生成物とからの混合物を取り出し、かつ前記塔の底部で、精製された粗N−ビニルピロリドンと水とからの混合物を取り出すことを特徴とする、請求項15記載の方法。
- 前記抽出によって、蛍光性副生成物を、前記粗N−ビニルアミドから、N−ビニルピロリドン100質量部に対して0.05質量部より小さい含有率まで除去することを特徴とする、請求項1から16までのいずれか1項記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP08170175.7 | 2008-11-28 | ||
EP08170175 | 2008-11-28 | ||
PCT/EP2009/065038 WO2010060801A1 (de) | 2008-11-28 | 2009-11-12 | Verfahren zur entfernung von nebenprodukten aus n-vinylamiden |
Related Child Applications (1)
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JP2014265278A Division JP2015083600A (ja) | 2008-11-28 | 2014-12-26 | N−ビニルアミドから副生成物を除去する方法 |
Publications (2)
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JP2012510440A true JP2012510440A (ja) | 2012-05-10 |
JP5734199B2 JP5734199B2 (ja) | 2015-06-17 |
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JP2011537923A Active JP5734199B2 (ja) | 2008-11-28 | 2009-11-12 | N−ビニルアミドから副生成物を除去する方法 |
JP2014265278A Pending JP2015083600A (ja) | 2008-11-28 | 2014-12-26 | N−ビニルアミドから副生成物を除去する方法 |
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Country Status (7)
Country | Link |
---|---|
US (1) | US20110245510A1 (ja) |
EP (1) | EP2370397B1 (ja) |
JP (2) | JP5734199B2 (ja) |
KR (1) | KR20110096055A (ja) |
CN (1) | CN102227403B (ja) |
ES (1) | ES2400329T3 (ja) |
WO (1) | WO2010060801A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2011506381A (ja) * | 2007-12-11 | 2011-03-03 | ビーエーエスエフ ソシエタス・ヨーロピア | アミドのビニル化方法 |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
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JP5734199B2 (ja) * | 2008-11-28 | 2015-06-17 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | N−ビニルアミドから副生成物を除去する方法 |
DE102011080762A1 (de) | 2010-08-10 | 2012-02-16 | Basf Se | Verfahren zur Aufarbeitung von Pyrrolidon- und N-Vinylpyrrolidon-Rückständen im Dünnschichtverdampfer |
CN102503880B (zh) * | 2011-10-18 | 2013-10-02 | 华诺森(武汉)生物医药技术有限公司 | 一种提纯n-乙烯基化合物的方法 |
CN102532025B (zh) * | 2011-12-15 | 2014-02-12 | 北京天弘天达医药科技有限公司 | 循环利用原料的n-乙烯基已内酰胺的制备方法 |
CN111097191B (zh) * | 2018-10-25 | 2021-10-01 | 中国石油化工股份有限公司 | 萃取-精馏法回收有机溶剂的方法 |
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DE10255437B4 (de) | 2001-12-05 | 2017-02-09 | Basf Se | Kontinuierliches Verfahren zur Herstellung von Alkenylverbindungen |
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- 2009-11-12 WO PCT/EP2009/065038 patent/WO2010060801A1/de active Application Filing
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CN102227403A (zh) | 2011-10-26 |
WO2010060801A1 (de) | 2010-06-03 |
US20110245510A1 (en) | 2011-10-06 |
EP2370397B1 (de) | 2013-01-16 |
JP5734199B2 (ja) | 2015-06-17 |
KR20110096055A (ko) | 2011-08-26 |
ES2400329T3 (es) | 2013-04-09 |
EP2370397A1 (de) | 2011-10-05 |
CN102227403B (zh) | 2014-12-10 |
JP2015083600A (ja) | 2015-04-30 |
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