CN103588706B - 包括光亚硝化步骤然后贝克曼重排作用步骤的制备内酰胺的方法 - Google Patents
包括光亚硝化步骤然后贝克曼重排作用步骤的制备内酰胺的方法 Download PDFInfo
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- CN103588706B CN103588706B CN201310505599.XA CN201310505599A CN103588706B CN 103588706 B CN103588706 B CN 103588706B CN 201310505599 A CN201310505599 A CN 201310505599A CN 103588706 B CN103588706 B CN 103588706B
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- photonitrosation
- microreactor
- beckmann rearrangement
- dechlorination
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- 238000006237 Beckmann rearrangement reaction Methods 0.000 title claims abstract description 36
- 150000003951 lactams Chemical class 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000006298 dechlorination reaction Methods 0.000 claims abstract description 33
- 239000011521 glass Substances 0.000 claims abstract description 18
- -1 oxime hydrochloride Chemical class 0.000 claims abstract description 17
- 150000001924 cycloalkanes Chemical class 0.000 claims abstract description 15
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 claims abstract description 11
- 235000019392 nitrosyl chloride Nutrition 0.000 claims abstract description 11
- 239000004157 Nitrosyl chloride Substances 0.000 claims abstract description 10
- DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical group C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 claims description 5
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- 229910052715 tantalum Inorganic materials 0.000 claims description 3
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
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- 238000006243 chemical reaction Methods 0.000 description 30
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 24
- 150000002923 oximes Chemical class 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000001117 sulphuric acid Substances 0.000 description 10
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- 230000008707 rearrangement Effects 0.000 description 9
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- 239000011734 sodium Substances 0.000 description 7
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- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
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- 239000000463 material Substances 0.000 description 5
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- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- SCRFXJBEIINMIC-UHFFFAOYSA-N n-cyclododecylidenehydroxylamine Chemical compound ON=C1CCCCCCCCCCC1 SCRFXJBEIINMIC-UHFFFAOYSA-N 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000295 emission spectrum Methods 0.000 description 3
- UXOLDCOJRAMLTQ-UTCJRWHESA-N ethyl (2z)-2-chloro-2-hydroxyiminoacetate Chemical compound CCOC(=O)C(\Cl)=N\O UXOLDCOJRAMLTQ-UTCJRWHESA-N 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000013529 heat transfer fluid Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
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- 239000000203 mixture Substances 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 208000035126 Facies Diseases 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
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- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000006552 photochemical reaction Methods 0.000 description 2
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- 239000000376 reactant Substances 0.000 description 2
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- 238000007086 side reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 235000011960 Brassica ruvo Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000007126 N-alkylation reaction Methods 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 1
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- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
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- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000002241 glass-ceramic Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005355 lead glass Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- XSIDCAOQNLRQEL-UHFFFAOYSA-N n-cyclododecylidenehydroxylamine;hydrochloride Chemical compound Cl.ON=C1CCCCCCCCCCC1 XSIDCAOQNLRQEL-UHFFFAOYSA-N 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
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- 238000011084 recovery Methods 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
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- 238000012546 transfer Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
- C07D201/02—Preparation of lactams
- C07D201/10—Preparation of lactams from cycloaliphatic compounds by simultaneous nitrosylation and rearrangement
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
- C07D201/02—Preparation of lactams
- C07D201/04—Preparation of lactams from or via oximes by Beckmann rearrangement
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/06—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by nitrosation of hydrocarbons or substituted hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D225/00—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom
- C07D225/02—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D227/00—Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00
- C07D227/02—Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00 with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D227/06—Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00 with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D227/08—Oxygen atoms
- C07D227/087—One doubly-bound oxygen atom in position 2, e.g. lactams
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
- C07C2601/20—Systems containing only non-condensed rings with a ring being at least seven-membered the ring being twelve-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR08.53419 | 2008-05-26 | ||
| FR0853419A FR2931478B1 (fr) | 2008-05-26 | 2008-05-26 | Prodece de preparation de lactames comprenant une etape de photonitrosation suivie d'une etape de transposition de beckmann |
| CN200980119112.6A CN102046604B (zh) | 2008-05-26 | 2009-05-14 | 包括光亚硝化步骤然后贝克曼重排作用步骤的制备内酰胺的方法 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200980119112.6A Division CN102046604B (zh) | 2008-05-26 | 2009-05-14 | 包括光亚硝化步骤然后贝克曼重排作用步骤的制备内酰胺的方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103588706A CN103588706A (zh) | 2014-02-19 |
| CN103588706B true CN103588706B (zh) | 2016-08-24 |
Family
ID=40134955
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310505599.XA Active CN103588706B (zh) | 2008-05-26 | 2009-05-14 | 包括光亚硝化步骤然后贝克曼重排作用步骤的制备内酰胺的方法 |
| CN200980119112.6A Active CN102046604B (zh) | 2008-05-26 | 2009-05-14 | 包括光亚硝化步骤然后贝克曼重排作用步骤的制备内酰胺的方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200980119112.6A Active CN102046604B (zh) | 2008-05-26 | 2009-05-14 | 包括光亚硝化步骤然后贝克曼重排作用步骤的制备内酰胺的方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US20110137027A1 (enExample) |
| EP (2) | EP2291357B1 (enExample) |
| JP (5) | JP6235769B2 (enExample) |
| CN (2) | CN103588706B (enExample) |
| FR (1) | FR2931478B1 (enExample) |
| PL (2) | PL3101011T3 (enExample) |
| WO (1) | WO2009153470A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2931478B1 (fr) * | 2008-05-26 | 2012-08-03 | Arkema France | Prodece de preparation de lactames comprenant une etape de photonitrosation suivie d'une etape de transposition de beckmann |
| JP5359064B2 (ja) * | 2008-06-30 | 2013-12-04 | 東レ株式会社 | シクロアルカノンオキシムの製造方法および光化学反応装置 |
| JP5359063B2 (ja) * | 2008-06-30 | 2013-12-04 | 東レ株式会社 | シクロアルカノンオキシムの製造方法 |
| JP5821623B2 (ja) * | 2010-12-28 | 2015-11-24 | 東レ株式会社 | シクロアルカノンオキシムの製造方法およびラクタムを製造する方法 |
| KR101276149B1 (ko) | 2012-06-26 | 2013-06-18 | 도레이 카부시키가이샤 | 시클로알카논 옥심의 제조 방법 |
| TWI564278B (zh) | 2012-06-27 | 2017-01-01 | 東麗股份有限公司 | 環烷酮肟之製造方法及內醯胺之製造方法 |
| ES2794123T3 (es) * | 2014-10-09 | 2020-11-17 | Toray Industries | Dispositivo de reacción fotoquímica, método de reacción fotoquímica que lo utiliza, y método de producción de lactamas para utilizar dicho método |
| CN107438594B (zh) | 2015-04-02 | 2020-11-06 | 安西娅芳香剂私人有限公司 | 一种用于合成环酰胺的有效的工艺 |
| WO2017133995A1 (de) | 2016-02-01 | 2017-08-10 | Basf Se | Verfahren zur herstellung von c4-c15-lactamen |
| CN108409646B (zh) * | 2018-01-19 | 2020-05-19 | 南京红太阳生物化学有限责任公司 | 一种烟酰胺的合成方法 |
| FR3107612B1 (fr) | 2020-02-20 | 2022-03-04 | Arkema France | Lampe pour réacteur photochimique à base de diodes électroluminescentes |
| CN115260073B (zh) * | 2022-08-31 | 2024-09-20 | 中国天辰工程有限公司 | 一种无硫酸铵副产重排工艺制备月桂精内酰胺的方法 |
| CN119258936B (zh) * | 2023-07-07 | 2025-11-11 | 中国石油化工股份有限公司 | 一种微反应设备脱除原油中有机氯的方法 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3553091A (en) * | 1966-08-17 | 1971-01-05 | Fumio Nishikawa | Method of photonitrosation of cycloalkanes |
| CN1252404A (zh) * | 1998-09-21 | 2000-05-10 | 埃勒夫阿托化学有限公司 | 制备ω－十二碳内酰胺的方法 |
| JP2001002636A (ja) * | 1999-06-15 | 2001-01-09 | Toray Ind Inc | ラクタムの製造方法 |
| JP2003529578A (ja) * | 2000-03-31 | 2003-10-07 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | 有機オキシムのベックマン転位のための方法 |
| WO2007105647A1 (ja) * | 2006-03-10 | 2007-09-20 | Nichia Corporation | 発光装置 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3652552A (en) * | 1966-12-16 | 1972-03-28 | Stamicarbon | Preparation of lactams from cycloalkanes |
| FR2417501A1 (fr) * | 1978-02-17 | 1979-09-14 | Ato Chimie | Procede de preparation de lactames par isomerisation d'oximes en milieu sulfurique |
| BE893651A (fr) * | 1982-06-25 | 1982-12-27 | Desaar Rene | Nez poreux pour le bullage d'acier |
| KR100530730B1 (ko) * | 1997-07-02 | 2005-11-23 | 아르끄마 | 유사 무수 매질내 클로로포름중 시클로도데칸의 광화학니트로소화 반응을 통한 시클로도데카논 옥심의 제조방법 |
| JP2000164931A (ja) | 1998-11-27 | 2000-06-16 | Sumitomo Electric Ind Ltd | 白色光源 |
| JP4397394B2 (ja) * | 2003-01-24 | 2010-01-13 | ディジタル・オプティクス・インターナショナル・コーポレイション | 高密度照明システム |
| WO2006013699A1 (ja) | 2004-08-04 | 2006-02-09 | Matsushita Electric Industrial Co., Ltd. | 無線通信装置、無線通信システム及び無線通信方法 |
| DE102005003966A1 (de) * | 2005-01-27 | 2006-08-10 | Ehrfeld Mikrotechnik Bts Gmbh | Vorrichtung zur kontinuierlichen Durchführung photochemischer Prozesse mit geringen optischen Schichtdicken, enger Verweilzeitverteilung und hohen Durchsätzen |
| FR2887250B1 (fr) * | 2005-06-21 | 2009-10-02 | Arkema Sa | Procede de synthese du lauryllactame (l12) par rearrangement catalytique en phase gazeuse de la cyclododecanone oxime |
| JP5110779B2 (ja) * | 2005-07-21 | 2012-12-26 | 日東電工株式会社 | 光反応生成物シート類の製造方法及び装置 |
| BRPI0712439B1 (pt) * | 2006-05-31 | 2019-11-05 | Cree, Inc. | dispositivo de iluminação e método de iluminação |
| JP5030222B2 (ja) | 2006-09-08 | 2012-09-19 | 国立大学法人東京工業大学 | 光触媒系マイクロ反応装置 |
| JP2009235365A (ja) | 2008-03-28 | 2009-10-15 | Toyota Motor Corp | ポリ乳酸複合成形体、ポリ乳酸複合成形体の製造方法及び自動車内装材用表面部材 |
| FR2931478B1 (fr) * | 2008-05-26 | 2012-08-03 | Arkema France | Prodece de preparation de lactames comprenant une etape de photonitrosation suivie d'une etape de transposition de beckmann |
| JP5359063B2 (ja) * | 2008-06-30 | 2013-12-04 | 東レ株式会社 | シクロアルカノンオキシムの製造方法 |
| JP5359064B2 (ja) * | 2008-06-30 | 2013-12-04 | 東レ株式会社 | シクロアルカノンオキシムの製造方法および光化学反応装置 |
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2008
- 2008-05-26 FR FR0853419A patent/FR2931478B1/fr active Active
-
2009
- 2009-05-14 WO PCT/FR2009/050886 patent/WO2009153470A1/fr not_active Ceased
- 2009-05-14 CN CN201310505599.XA patent/CN103588706B/zh active Active
- 2009-05-14 CN CN200980119112.6A patent/CN102046604B/zh active Active
- 2009-05-14 PL PL16176645T patent/PL3101011T3/pl unknown
- 2009-05-14 EP EP09766032.8A patent/EP2291357B1/fr not_active Not-in-force
- 2009-05-14 US US12/993,975 patent/US20110137027A1/en not_active Abandoned
- 2009-05-14 PL PL09766032.8T patent/PL2291357T3/pl unknown
- 2009-05-14 JP JP2011511056A patent/JP6235769B2/ja active Active
- 2009-05-14 EP EP16176645.6A patent/EP3101011B1/fr active Active
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2014
- 2014-04-14 US US14/252,610 patent/US9499481B2/en active Active
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2015
- 2015-06-10 JP JP2015117852A patent/JP6567332B2/ja active Active
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2017
- 2017-01-12 JP JP2017003575A patent/JP2017081987A/ja active Pending
- 2017-04-06 JP JP2017075888A patent/JP2017132797A/ja active Pending
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2018
- 2018-12-17 JP JP2018235757A patent/JP2019055999A/ja active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3553091A (en) * | 1966-08-17 | 1971-01-05 | Fumio Nishikawa | Method of photonitrosation of cycloalkanes |
| CN1252404A (zh) * | 1998-09-21 | 2000-05-10 | 埃勒夫阿托化学有限公司 | 制备ω－十二碳内酰胺的方法 |
| JP2001002636A (ja) * | 1999-06-15 | 2001-01-09 | Toray Ind Inc | ラクタムの製造方法 |
| JP2003529578A (ja) * | 2000-03-31 | 2003-10-07 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | 有機オキシムのベックマン転位のための方法 |
| WO2007105647A1 (ja) * | 2006-03-10 | 2007-09-20 | Nichia Corporation | 発光装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2019055999A (ja) | 2019-04-11 |
| WO2009153470A1 (fr) | 2009-12-23 |
| CN102046604B (zh) | 2015-02-25 |
| JP2011521004A (ja) | 2011-07-21 |
| FR2931478A1 (fr) | 2009-11-27 |
| EP2291357A1 (fr) | 2011-03-09 |
| CN103588706A (zh) | 2014-02-19 |
| JP2017132797A (ja) | 2017-08-03 |
| PL3101011T3 (pl) | 2018-09-28 |
| JP6235769B2 (ja) | 2017-11-22 |
| PL2291357T3 (pl) | 2016-12-30 |
| US20140246303A1 (en) | 2014-09-04 |
| EP3101011B1 (fr) | 2018-06-20 |
| CN102046604A (zh) | 2011-05-04 |
| US20110137027A1 (en) | 2011-06-09 |
| EP2291357B1 (fr) | 2016-07-13 |
| JP2017081987A (ja) | 2017-05-18 |
| JP2015157871A (ja) | 2015-09-03 |
| US9499481B2 (en) | 2016-11-22 |
| EP3101011A1 (fr) | 2016-12-07 |
| JP6567332B2 (ja) | 2019-08-28 |
| FR2931478B1 (fr) | 2012-08-03 |
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