JP2010532762A5 - - Google Patents
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- Publication number
- JP2010532762A5 JP2010532762A5 JP2010515272A JP2010515272A JP2010532762A5 JP 2010532762 A5 JP2010532762 A5 JP 2010532762A5 JP 2010515272 A JP2010515272 A JP 2010515272A JP 2010515272 A JP2010515272 A JP 2010515272A JP 2010532762 A5 JP2010532762 A5 JP 2010532762A5
- Authority
- JP
- Japan
- Prior art keywords
- chloropropane
- metal
- tetrafluoropropene
- catalyst
- tetrafluoro
- 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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- 238000000034 method Methods 0.000 claims description 31
- 239000003054 catalyst Substances 0.000 claims description 18
- 229910001507 metal halide Inorganic materials 0.000 claims description 17
- 150000005309 metal halides Chemical class 0.000 claims description 17
- AIYUHDOJVYHVIT-UHFFFAOYSA-M caesium chloride Chemical compound [Cl-].[Cs+] AIYUHDOJVYHVIT-UHFFFAOYSA-M 0.000 claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 150000001336 alkenes Chemical class 0.000 claims description 8
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 8
- 229910001092 metal group alloy Inorganic materials 0.000 claims description 7
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 claims description 6
- CDOOAUSHHFGWSA-OWOJBTEDSA-N (e)-1,3,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C\C(F)(F)F CDOOAUSHHFGWSA-OWOJBTEDSA-N 0.000 claims description 4
- DMUPYMORYHFFCT-UPHRSURJSA-N (z)-1,2,3,3,3-pentafluoroprop-1-ene Chemical compound F\C=C(/F)C(F)(F)F DMUPYMORYHFFCT-UPHRSURJSA-N 0.000 claims description 4
- QAERDLQYXMEHEB-UHFFFAOYSA-N 1,1,3,3,3-pentafluoroprop-1-ene Chemical compound FC(F)=CC(F)(F)F QAERDLQYXMEHEB-UHFFFAOYSA-N 0.000 claims description 4
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 claims description 4
- SMCNZLDHTZESTK-UHFFFAOYSA-N 2-chloro-1,1,1,2-tetrafluoropropane Chemical compound CC(F)(Cl)C(F)(F)F SMCNZLDHTZESTK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 4
- 150000002739 metals Chemical class 0.000 claims description 4
- SCDLWHGUKGDYQD-UHFFFAOYSA-N 2-chloro-1,1,1,2,3,3-hexafluoropropane Chemical compound FC(F)C(F)(Cl)C(F)(F)F SCDLWHGUKGDYQD-UHFFFAOYSA-N 0.000 claims description 2
- LDMYCECIGXPKDO-UHFFFAOYSA-N 2-chloro-1,1,1,2,3-pentafluoropropane Chemical compound FCC(F)(Cl)C(F)(F)F LDMYCECIGXPKDO-UHFFFAOYSA-N 0.000 claims description 2
- JYNCTFQDWJMJDI-UHFFFAOYSA-N 2-chloro-1,1,1,3,3-pentafluoropropane Chemical compound FC(F)C(Cl)C(F)(F)F JYNCTFQDWJMJDI-UHFFFAOYSA-N 0.000 claims description 2
- CNNJBYUJTYGLGG-UHFFFAOYSA-N 2-chloro-1,1,1,3-tetrafluoropropane Chemical compound FCC(Cl)C(F)(F)F CNNJBYUJTYGLGG-UHFFFAOYSA-N 0.000 claims description 2
- SOPMTTFVKDXVEM-UHFFFAOYSA-N 3-chloro-1,1,1,2,3-pentafluoropropane Chemical compound FC(Cl)C(F)C(F)(F)F SOPMTTFVKDXVEM-UHFFFAOYSA-N 0.000 claims description 2
- JSECXTYNFBONSF-UHFFFAOYSA-N 3-chloro-1,1,1,2-tetrafluoropropane Chemical compound ClCC(F)C(F)(F)F JSECXTYNFBONSF-UHFFFAOYSA-N 0.000 claims description 2
- ZGOMEYREADWKLC-UHFFFAOYSA-N 3-chloro-1,1,1,3-tetrafluoropropane Chemical compound FC(Cl)CC(F)(F)F ZGOMEYREADWKLC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000007033 dehydrochlorination reaction Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 18
- 150000004706 metal oxides Chemical class 0.000 description 18
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- LLJWABOOFANACB-UHFFFAOYSA-N 1-chloro-1,1,3,3,3-pentafluoropropane Chemical compound FC(F)(F)CC(F)(F)Cl LLJWABOOFANACB-UHFFFAOYSA-N 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95846807P | 2007-07-06 | 2007-07-06 | |
| US60/958,468 | 2007-07-06 | ||
| US12/167,159 US9040759B2 (en) | 2007-07-06 | 2008-07-02 | Preparation of fluorinated olefins via catalytic dehydrohalogenation of halogenated hydrocarbons |
| US12/167,159 | 2008-07-02 | ||
| PCT/US2008/069160 WO2009009421A1 (en) | 2007-07-06 | 2008-07-03 | Preparation of fluorinated olefins via catalytic dehydrohalogenation of halogenated hydrocarbons |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010532762A JP2010532762A (ja) | 2010-10-14 |
| JP2010532762A5 true JP2010532762A5 (enExample) | 2011-08-11 |
| JP5436417B2 JP5436417B2 (ja) | 2014-03-05 |
Family
ID=40228992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010515272A Active JP5436417B2 (ja) | 2007-07-06 | 2008-07-03 | ハロゲン化された炭化水素の触媒による脱ハロゲン化水素化によるフッ素化されたオレフィンの調製 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US9040759B2 (enExample) |
| EP (1) | EP2164824B1 (enExample) |
| JP (1) | JP5436417B2 (enExample) |
| KR (3) | KR101711140B1 (enExample) |
| CN (1) | CN101687737B (enExample) |
| ES (1) | ES2719478T3 (enExample) |
| MX (1) | MX2009013376A (enExample) |
| WO (1) | WO2009009421A1 (enExample) |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8530708B2 (en) * | 2003-07-25 | 2013-09-10 | Honeywell International Inc. | Processes for selective dehydrohalogenation of halogenated alkanes |
| US8664455B2 (en) | 2008-08-08 | 2014-03-04 | Honeywell International Inc. | Process to manufacture 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) |
| US8952208B2 (en) * | 2006-01-03 | 2015-02-10 | Honeywell International Inc. | Method for prolonging a catalyst's life during hydrofluorination |
| US8034251B2 (en) | 2007-01-03 | 2011-10-11 | Honeywell International Inc. | Azeotropic compositions of 2-chloro-3,3,3-trifluoropropene (HCFC-1233xf), 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb), and hydrogen fluoride (HF) |
| US9040759B2 (en) * | 2007-07-06 | 2015-05-26 | Honeywell International Inc. | Preparation of fluorinated olefins via catalytic dehydrohalogenation of halogenated hydrocarbons |
| US9416074B2 (en) | 2007-07-06 | 2016-08-16 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| US8119557B2 (en) * | 2007-12-10 | 2012-02-21 | Honeywell International Inc. | Method for making catalyst compositions of alkali metal halide-doped bivalent metal fluorides and process for making fluorinated olefins |
| US8846990B2 (en) | 2007-07-06 | 2014-09-30 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| EP2075066B1 (en) * | 2007-12-10 | 2016-08-17 | Honeywell International Inc. | Method for making catalyst compositions of alkali metal halide-doped bivalent metal fluorides and a process for making fluorinated olefins |
| US7803283B2 (en) * | 2008-03-31 | 2010-09-28 | Honeywell Internationl Inc. | Azeotrope-like compositions of 2-chloro-3,3,3-trifluoropropene (HCFC-1233xf) and 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) |
| US8845921B2 (en) | 2008-04-09 | 2014-09-30 | Honeywell International Inc. | Separation of close boiling compounds by addition of a third compound |
| US8877086B2 (en) * | 2008-05-07 | 2014-11-04 | E I Du Pont De Nemours And Company | Compositions comprising 2,3-dichloro-1,1,1-trifluoropropane, 2-chloro-1,1,1-trifluoropropene, 2-chloro-1,1,1,2-tetrafluoropropane or 2,3,3,3-tetrafluoropropene |
| US8053612B2 (en) * | 2008-05-30 | 2011-11-08 | Honeywell International Inc. | Process for dehydrochlorinating 1,1,1,2-tetrafluoro-2-chloropropane to 2,3,3,3-tetrafluoropropene in the presence of an alkali metal-doped magnesium oxyfluoride catalyst and methods for making the catalyst |
| US8975454B2 (en) * | 2008-07-31 | 2015-03-10 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| US8158549B2 (en) * | 2009-09-04 | 2012-04-17 | Honeywell International Inc. | Catalysts for fluoroolefins hydrogenation |
| US8618340B2 (en) * | 2009-11-03 | 2013-12-31 | Honeywell International Inc. | Integrated process for fluoro-olefin production |
| ES2531185T3 (es) * | 2010-04-02 | 2015-03-11 | Solvay | Procedimiento para la deshidrocloración de hidroclorofluoroalcanos |
| US8426656B2 (en) * | 2010-04-05 | 2013-04-23 | Honeywell International Inc. | Integrated process to co-produce trans-1-chloro-3,3,3-trifluoropropene and trans-1,3,3,3-tetrafluoropropene |
| US8927791B2 (en) | 2010-04-29 | 2015-01-06 | Honeywell International Inc. | Method for producing tetrafluoropropenes |
| US8263817B2 (en) * | 2010-07-06 | 2012-09-11 | E I Du Pont De Nemours And Company | Synthesis of 1234YF by selective dehydrochlorination of 244BB |
| CN101913989B (zh) * | 2010-09-07 | 2013-06-05 | 西安近代化学研究所 | 2,3,3,3-四氟丙烯的生产方法 |
| US8884083B2 (en) | 2011-02-21 | 2014-11-11 | E. I. Du Pont De Nemours And Company | Selective catalytical dehydrochlorination of hydrochlorofluorocarbons |
| US9012702B2 (en) * | 2011-02-21 | 2015-04-21 | E. I. Du Pont De Nemours And Company | Catalytic dehydrochlorination of hydrochlorofluorocarbons |
| US9724684B2 (en) * | 2011-02-21 | 2017-08-08 | The Chemours Company Fc, Llc | Selective catalytical dehydrochlorination of hydrochlorofluorocarbons |
| US8884082B2 (en) | 2011-02-21 | 2014-11-11 | E. I. Du Pont De Nemours And Company | Selective catalytical dehydrochlorination of hydrochlorofluorocarbons |
| CN102887812A (zh) * | 2011-07-20 | 2013-01-23 | 中化蓝天集团有限公司 | 1,1,3,3,3-五氟丙烯的合成方法 |
| US8796493B2 (en) * | 2011-09-30 | 2014-08-05 | Honeywell International Inc. | Methods to separate halogentated olefins from 2-chloro-1,1,1,2-tetrafluoropropane using a solid adsorbent |
| KR20140075790A (ko) * | 2011-10-14 | 2014-06-19 | 허니웰 인터내셔날 인코포레이티드 | 2,3,3,3-테트라플루오로프로펜의 제조 방법 |
| JP6223346B2 (ja) * | 2011-10-14 | 2017-11-01 | ハネウェル・インターナショナル・インコーポレーテッドＨｏｎｅｙｗｅｌｌ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｉｎｃ． | ２，３，３，３−テトラフルオロプロペンの製造方法 |
| US9000239B2 (en) | 2012-05-15 | 2015-04-07 | Honeywell International Inc. | Methods for producing 1-chloro-3,3,3-trifluoropropene from 2-chloro-3,3,3-trifluoropropene |
| US9180433B2 (en) | 2013-03-14 | 2015-11-10 | Honeywell International, Inc. | Catalysts for 2-chloro-1,1,1,2-tetrafluoropropane dehydrochlorination |
| CN104707608B (zh) * | 2013-12-12 | 2017-02-15 | 西安近代化学研究所 | 用于气相氟化制备2‑氯‑3,3,3‑三氟丙烯的催化剂的制备方法 |
| GB2528690B (en) * | 2014-07-28 | 2017-03-01 | Mexichem Amanco Holding Sa | Process for preparing a (hydro)(chloro)fluoroalkene |
| CN105327695A (zh) * | 2014-08-06 | 2016-02-17 | 浙江蓝天环保高科技股份有限公司 | 一种用于脱氟化氢的铬基催化剂、其制备方法及应用 |
| US9850188B2 (en) * | 2014-09-05 | 2017-12-26 | Honeywell International Inc. | Process for producing chlorotrifluoroethylene |
| US9938213B2 (en) * | 2015-08-19 | 2018-04-10 | Honeywell International Inc. | Methods for removing acidic impurities from halogenated propenes |
| JP6971226B2 (ja) * | 2015-10-15 | 2021-11-24 | ハネウェル・インターナショナル・インコーポレーテッドHoneywell International Inc. | 脱ハロゲン化水素化反応器及び方法 |
| CN105251516B (zh) * | 2015-11-06 | 2018-03-13 | 西安近代化学研究所 | 一种用于合成含氟卤代烃的催化剂及其制备方法 |
| CN105399599B (zh) * | 2015-12-28 | 2018-05-29 | 浙江工业大学 | 一种制备六氟丁二烯的方法 |
| FR3066926B1 (fr) * | 2017-06-06 | 2020-05-22 | Arkema France | Procede de modification de la distribution en fluor dans un compose hydrocarbure. |
| KR102689847B1 (ko) * | 2017-07-27 | 2024-07-31 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | (z)-1,1,1,4,4,4-헥사플루오로-2-부텐의 제조 방법 |
| JP6974221B2 (ja) | 2018-03-14 | 2021-12-01 | 株式会社クレハ | アルケンの製造方法 |
| KR102549545B1 (ko) * | 2018-03-22 | 2023-06-29 | 삼성전자주식회사 | 스토리지 장치 및 스토리지 장치의 동작 방법 |
| CN119118782A (zh) | 2018-06-06 | 2024-12-13 | 霍尼韦尔国际公司 | 用于HCFC-244bb的脱氯化氢以制备HFO-1234yf的方法 |
| CN110639493B (zh) * | 2019-09-24 | 2023-02-10 | 西安近代化学研究所 | 一种高选择性脱氯化氢催化剂的成型方法 |
| CN110841722B (zh) * | 2019-10-16 | 2022-09-06 | 鄂尔多斯市瀚博科技有限公司 | 一种用于氯乙烯合成的无汞催化剂钝化工艺 |
| CN114078605B (zh) * | 2021-11-02 | 2025-08-08 | 武汉理工大学 | 一种放射性金属卤化物废物的脱卤及玻璃固化方法 |
| CN119528682A (zh) * | 2024-11-04 | 2025-02-28 | 西安近代化学研究所 | 一种含氟双氯烯烃、制备方法及应用 |
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| US2774799A (en) * | 1954-04-01 | 1956-12-18 | Kellogg M W Co | Selective dehydrohalogenation of fluorohaloalkanes using a copper catalyst |
| DE1074568B (de) * | 1955-04-05 | 1960-02-04 | Ethyl Corporation, New York N Y (V St A) | Verfahren zur Herstellung von Vinylchlorid oder Vinylidenchlorid 5 4 5ö V St Amerika |
| DE1068695B (de) * | 1958-02-06 | 1959-11-12 | Farbwerke Hoechst Aktiengesellschaft vormals Meister Lucius 6. Brüning, Frankfurt/M | Verfahren zur Herstellung von Fluoräthylenen |
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| US3691240A (en) * | 1969-10-06 | 1972-09-12 | Detrex Chem Ind | Process for chlorination,dehydrochlorination and purification of organic compounds |
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| BR8907438A (pt) * | 1989-03-17 | 1991-05-21 | Dow Chemical Co | Processo e catalisador para a desidrohalogenacao de hidrocarbonetos halogenados ou halohidrinas de alquileno |
| US5180860A (en) * | 1990-06-28 | 1993-01-19 | E. I. Du Pont De Nemours And Company | Dehydrohalogenation process |
| US5276240A (en) * | 1991-10-18 | 1994-01-04 | Board Of Regents, The University Of Texas System | Catalytic hydrodehalogenation of polyhalogenated hydrocarbons |
| GB9311742D0 (en) * | 1992-06-10 | 1993-07-21 | Ici Plc | Production of hydrofluoroalkanes |
| CZ303077B6 (cs) * | 1998-12-18 | 2012-03-21 | Solvay (Societe Anonyme) | Zpusob separace smesi obsahující alespon jeden hydrofluoralkan a fluorovodík, zpusob prípravy hydrofluoralkanu a azeotropní kompozice |
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| US7880040B2 (en) * | 2004-04-29 | 2011-02-01 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
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| US7674939B2 (en) * | 2004-04-29 | 2010-03-09 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| ES2528181T7 (es) * | 2004-04-29 | 2020-03-30 | Honeywell Int Inc | Procedimientos para la síntesis de 1,3,3,3-tetrafluoropropeno y 2,3,3,3-tetrafluoropropeno |
| US8084653B2 (en) * | 2004-04-29 | 2011-12-27 | Honeywell International, Inc. | Method for producing fluorinated organic compounds |
| US7560602B2 (en) * | 2005-11-03 | 2009-07-14 | Honeywell International Inc. | Process for manufacture of fluorinated olefins |
| ES2400732T3 (es) * | 2005-11-03 | 2013-04-11 | Honeywell International Inc. | Método para la producción de compuestos orgánicos fluorados |
| JP5270361B2 (ja) * | 2005-11-03 | 2013-08-21 | ハネウェル・インターナショナル・インコーポレーテッド | フッ素化有機化合物の製造方法 |
| ES2639623T5 (es) | 2006-01-03 | 2024-10-04 | Honeywell Int Inc | Método para preparar compuestos orgánicos fluorados |
| US8071825B2 (en) * | 2006-01-03 | 2011-12-06 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| WO2008040969A2 (en) | 2006-10-03 | 2008-04-10 | Ineos Fluor Holdings Limited | Dehydrogenationhalogenation process for the production of c3-c6-(hydro)fluoroalkenes |
| US8119557B2 (en) * | 2007-12-10 | 2012-02-21 | Honeywell International Inc. | Method for making catalyst compositions of alkali metal halide-doped bivalent metal fluorides and process for making fluorinated olefins |
| US9040759B2 (en) * | 2007-07-06 | 2015-05-26 | Honeywell International Inc. | Preparation of fluorinated olefins via catalytic dehydrohalogenation of halogenated hydrocarbons |
| EP2075066B1 (en) * | 2007-12-10 | 2016-08-17 | Honeywell International Inc. | Method for making catalyst compositions of alkali metal halide-doped bivalent metal fluorides and a process for making fluorinated olefins |
| US8053612B2 (en) * | 2008-05-30 | 2011-11-08 | Honeywell International Inc. | Process for dehydrochlorinating 1,1,1,2-tetrafluoro-2-chloropropane to 2,3,3,3-tetrafluoropropene in the presence of an alkali metal-doped magnesium oxyfluoride catalyst and methods for making the catalyst |
-
2008
- 2008-07-02 US US12/167,159 patent/US9040759B2/en active Active
- 2008-07-03 KR KR1020157031523A patent/KR101711140B1/ko active Active
- 2008-07-03 CN CN200880023701XA patent/CN101687737B/zh active Active
- 2008-07-03 MX MX2009013376A patent/MX2009013376A/es active IP Right Grant
- 2008-07-03 ES ES08772398T patent/ES2719478T3/es active Active
- 2008-07-03 KR KR1020177005035A patent/KR101875204B1/ko active Active
- 2008-07-03 WO PCT/US2008/069160 patent/WO2009009421A1/en not_active Ceased
- 2008-07-03 EP EP08772398.7A patent/EP2164824B1/en active Active
- 2008-07-03 KR KR1020107002119A patent/KR20100040897A/ko not_active Ceased
- 2008-07-03 JP JP2010515272A patent/JP5436417B2/ja active Active
-
2015
- 2015-05-26 US US14/721,575 patent/US10807925B2/en active Active
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