JP2012505296A5 - - Google Patents
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- JP2012505296A5 JP2012505296A5 JP2011531192A JP2011531192A JP2012505296A5 JP 2012505296 A5 JP2012505296 A5 JP 2012505296A5 JP 2011531192 A JP2011531192 A JP 2011531192A JP 2011531192 A JP2011531192 A JP 2011531192A JP 2012505296 A5 JP2012505296 A5 JP 2012505296A5
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- composition
- cclfch
- hfo
- acetate
- 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.)
- Pending
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 43
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 26
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 24
- BOUGCJDAQLKBQH-UHFFFAOYSA-N 1-chloro-1,2,2,2-tetrafluoroethane Chemical compound FC(Cl)C(F)(F)F BOUGCJDAQLKBQH-UHFFFAOYSA-N 0.000 claims description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- -1 CF 3 CHFC1) Chemical compound 0.000 claims description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 17
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 13
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical compound FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 claims description 12
- BAMUEXIPKSRTBS-UHFFFAOYSA-N 1,1-dichloro-1,2,2,2-tetrafluoroethane Chemical compound FC(F)(F)C(F)(Cl)Cl BAMUEXIPKSRTBS-UHFFFAOYSA-N 0.000 claims description 11
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 11
- JXLLSNNXICBZIS-UHFFFAOYSA-N (2-chloro-2,3,3,3-tetrafluoropropyl) acetate Chemical compound CC(=O)OCC(F)(Cl)C(F)(F)F JXLLSNNXICBZIS-UHFFFAOYSA-N 0.000 claims description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 claims description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 7
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 7
- PHSCLTQLFMNVOY-UHFFFAOYSA-N (2-chloro-2,3,3,3-tetrafluoropropoxy)methyl acetate Chemical compound CC(=O)OCOCC(F)(Cl)C(F)(F)F PHSCLTQLFMNVOY-UHFFFAOYSA-N 0.000 claims description 6
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 claims description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical compound FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 claims description 5
- KEGQZXLRQSXPJU-UHFFFAOYSA-N 1,3-difluoro-1,3-bis(trifluoromethyl)cyclobutane Chemical compound FC(F)(F)C1(F)CC(F)(C(F)(F)F)C1 KEGQZXLRQSXPJU-UHFFFAOYSA-N 0.000 claims description 5
- ZGDAIZKZNKWBTM-UHFFFAOYSA-N 2-chloro-2,3,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)(Cl)C(F)(F)F ZGDAIZKZNKWBTM-UHFFFAOYSA-N 0.000 claims description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 5
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims description 4
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims description 2
- HTHNTJCVPNKCPZ-UHFFFAOYSA-N 2-chloro-1,1-difluoroethene Chemical compound FC(F)=CCl HTHNTJCVPNKCPZ-UHFFFAOYSA-N 0.000 claims description 2
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims description 2
- GIUIQFXYGQJOIZ-UHFFFAOYSA-M [Cl-].[Zn++].[O-]CC(F)(Cl)C(F)(F)F Chemical compound [Cl-].[Zn++].[O-]CC(F)(Cl)C(F)(F)F GIUIQFXYGQJOIZ-UHFFFAOYSA-M 0.000 claims description 2
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 claims description 2
- DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical compound NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 claims description 2
- AOMUALOCHQKUCD-UHFFFAOYSA-N dodecyl 4-chloro-3-[[3-(4-methoxyphenyl)-3-oxopropanoyl]amino]benzoate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=C(Cl)C(NC(=O)CC(=O)C=2C=CC(OC)=CC=2)=C1 AOMUALOCHQKUCD-UHFFFAOYSA-N 0.000 claims description 2
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 7
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 5
- JVTSHOJDBRTPHD-UHFFFAOYSA-N 2,2,2-trifluoroacetaldehyde Chemical compound FC(F)(F)C=O JVTSHOJDBRTPHD-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- JQEQBVHLTKCNTI-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropyl acetate Chemical compound CC(=O)OCC(F)C(F)(F)F JQEQBVHLTKCNTI-UHFFFAOYSA-N 0.000 description 2
- MRQDALCRZBHBEM-UHFFFAOYSA-N 3-chloro-3,4,4,4-tetrafluorobutan-2-one Chemical compound CC(=O)C(F)(Cl)C(F)(F)F MRQDALCRZBHBEM-UHFFFAOYSA-N 0.000 description 2
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 2
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ILAUSMKPJVMSSC-UHFFFAOYSA-N (2-chloro-2,3,3,3-tetrafluoropropyl) formate Chemical compound FC(F)(F)C(F)(Cl)COC=O ILAUSMKPJVMSSC-UHFFFAOYSA-N 0.000 description 1
- TXOZSRCVHASUCW-UHFFFAOYSA-N 1,3,3,3-tetrafluoropropan-1-ol Chemical compound OC(F)CC(F)(F)F TXOZSRCVHASUCW-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- OZLDITVASCOILL-UHFFFAOYSA-N CC(=O)OCCC(C(F)(F)F)(F)Cl Chemical compound CC(=O)OCCC(C(F)(F)F)(F)Cl OZLDITVASCOILL-UHFFFAOYSA-N 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical class CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10433408P | 2008-10-10 | 2008-10-10 | |
| US61/104,334 | 2008-10-10 | ||
| PCT/US2009/060094 WO2010042781A2 (en) | 2008-10-10 | 2009-10-09 | Compositions comprising 2,3,3,3-tetrafluoropropene, 2-chloro-2,3,3,3-tetrafluoropropanol, 2-chloro-2,3,3,3-tetrafluoro-propyl acetate or zinc (2-chloro-2,3,3,3-tetrafluoropropoxy) chloride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012505296A JP2012505296A (ja) | 2012-03-01 |
| JP2012505296A5 true JP2012505296A5 (enExample) | 2012-11-22 |
Family
ID=41571037
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011531192A Pending JP2012505296A (ja) | 2008-10-10 | 2009-10-09 | ２，３，３，３−テトラフルオロプロペン、２−クロロ−２，３，３，３−テトラフルオロプロパノール、２−クロロ−２，３，３，３−テトラフルオロ酢酸プロピルまたは（２−クロロ−２，３，３，３−テトラフルオロプロポキシ）塩化亜鉛を含む組成物 |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US8147710B2 (enExample) |
| EP (1) | EP2331489A2 (enExample) |
| JP (1) | JP2012505296A (enExample) |
| KR (1) | KR20110084910A (enExample) |
| CN (1) | CN102177118A (enExample) |
| AU (1) | AU2009302263A1 (enExample) |
| BR (1) | BRPI0913806A2 (enExample) |
| CA (1) | CA2736216A1 (enExample) |
| MX (1) | MX2011003633A (enExample) |
| RU (1) | RU2011118429A (enExample) |
| TW (1) | TW201022425A (enExample) |
| WO (1) | WO2010042781A2 (enExample) |
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|---|---|---|---|---|
| DK2634231T3 (da) | 2008-05-07 | 2022-09-19 | Chemours Co Fc Llc | Sammensætninger |
| EP2271724B1 (en) | 2008-05-07 | 2013-04-24 | E. I. Du Pont de Nemours and Company | Compositions comprising 2,3,3,3- tetrafluoropropene |
| BRPI0913806A2 (pt) * | 2008-10-10 | 2015-10-20 | Du Pont | "composição" |
| WO2012021746A1 (en) | 2010-08-13 | 2012-02-16 | Carrier Corporation | Fluorinated hydrocarbon composition |
| IT1406472B1 (it) | 2010-12-22 | 2014-02-28 | Nuovo Pignone Spa | Prova per similitudine di prestazione di compressore |
| CN103562338B (zh) * | 2011-05-19 | 2016-09-07 | 旭硝子株式会社 | 工作介质及热循环系统 |
| US8845922B2 (en) * | 2011-12-20 | 2014-09-30 | Honeywell International Inc. | Compositions and use of vinylidene fluoride and blends thereof |
| CN102766022A (zh) * | 2012-08-09 | 2012-11-07 | 西安近代化学研究所 | 3，3，3-三氟丙醇的合成方法 |
| US9321867B2 (en) | 2012-12-21 | 2016-04-26 | Honeywell International Inc. | Synthesis of 2,3,3,3-tetrafluoropropene/vinylidene fluoride copolymers |
| FR3000096B1 (fr) * | 2012-12-26 | 2015-02-20 | Arkema France | Composition comprenant du 2,3,3,3-tetrafluoropropene |
| WO2014123120A1 (ja) | 2013-02-05 | 2014-08-14 | 旭硝子株式会社 | ヒートポンプ用作動媒体およびヒートポンプシステム |
| CN105392859B (zh) * | 2013-03-14 | 2018-05-04 | 霍尼韦尔国际公司 | 包含偏二氟乙烯的组合物和方法 |
| JP6038287B2 (ja) * | 2013-03-28 | 2016-12-07 | 三菱電機株式会社 | スクロール圧縮機及びそれを備えた冷凍サイクル装置 |
| EP2993212B1 (en) * | 2013-04-30 | 2019-08-28 | AGC Inc. | Working medium for heat cycle |
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| CN110373159B (zh) * | 2013-07-12 | 2021-08-10 | Ａｇｃ株式会社 | 热循环用工作介质、热循环系统用组合物以及热循环系统 |
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| EP3101081B1 (en) | 2014-01-31 | 2019-12-18 | AGC Inc. | Working fluid for heat cycle, composition for heat cycle system, and heat cycle system |
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| WO2015125880A1 (ja) * | 2014-02-20 | 2015-08-27 | 旭硝子株式会社 | 熱サイクルシステム用組成物および熱サイクルシステム |
| WO2015125876A1 (ja) * | 2014-02-20 | 2015-08-27 | 旭硝子株式会社 | 熱サイクルシステム用組成物および熱サイクルシステム |
| EP3109292B1 (en) * | 2014-02-20 | 2020-09-02 | AGC Inc. | Working fluid for heat cycle |
| EP3109302B1 (en) | 2014-02-20 | 2020-08-05 | AGC Inc. | Composition for heat cycle system, and heat cycle system |
| CN106029854B (zh) | 2014-02-20 | 2019-06-14 | Ａｇｃ株式会社 | 热循环系统用组合物以及热循环系统 |
| BR112016018711B1 (pt) * | 2014-02-20 | 2021-02-17 | AGC Inc. | composição para sistema de ciclo térmico e sistema de ciclo térmico |
| JP6540685B2 (ja) | 2014-02-28 | 2019-07-10 | Ａｇｃ株式会社 | 熱サイクル用作動媒体、熱サイクルシステム用組成物および熱サイクルシステム |
| JPWO2015133587A1 (ja) * | 2014-03-06 | 2017-04-06 | 旭硝子株式会社 | 熱サイクル用作動媒体および熱サイクルシステム |
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| JPWO2015136980A1 (ja) * | 2014-03-14 | 2017-04-06 | 三菱電機株式会社 | 冷凍サイクル装置 |
| JP6188918B2 (ja) * | 2014-03-14 | 2017-08-30 | 三菱電機株式会社 | 冷凍装置 |
| WO2015136704A1 (ja) * | 2014-03-14 | 2015-09-17 | 三菱電機株式会社 | 圧縮機及び冷凍サイクル装置 |
| CN106255736B (zh) * | 2014-03-17 | 2019-11-26 | Ａｇｃ株式会社 | 热循环用工作介质、热循环系统用组合物以及热循环系统 |
| CN106104173B (zh) * | 2014-03-17 | 2019-03-01 | 三菱电机株式会社 | 制冷循环装置 |
| WO2015140869A1 (ja) * | 2014-03-17 | 2015-09-24 | 三菱電機株式会社 | スクロール圧縮機 |
| EP3121538A1 (en) * | 2014-03-17 | 2017-01-25 | Mitsubishi Electric Corporation | Refrigeration cycle apparatus |
| JPWO2015140827A1 (ja) * | 2014-03-17 | 2017-04-06 | 三菱電機株式会社 | ヒートポンプ装置 |
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| WO2016059697A1 (ja) * | 2014-10-16 | 2016-04-21 | 三菱電機株式会社 | 冷凍サイクル装置 |
| CN106796057B (zh) * | 2014-10-16 | 2019-10-25 | 三菱电机株式会社 | 冷冻循环装置 |
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| MY182105A (en) | 2015-02-19 | 2021-01-18 | Daikin Ind Ltd | Composition containing mixture of fluorinated hydrocarbons, and method for producing same |
| WO2016181910A1 (ja) * | 2015-05-12 | 2016-11-17 | 旭硝子株式会社 | 熱サイクルシステム用組成物および熱サイクルシステム |
| CN117050728A (zh) | 2015-06-01 | 2023-11-14 | Ａｇｃ株式会社 | 热循环用工作介质、热循环系统用组合物以及热循环系统 |
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-
2009
- 2009-10-09 BR BRPI0913806A patent/BRPI0913806A2/pt not_active IP Right Cessation
- 2009-10-09 CN CN2009801401143A patent/CN102177118A/zh active Pending
- 2009-10-09 TW TW098134421A patent/TW201022425A/zh unknown
- 2009-10-09 CA CA2736216A patent/CA2736216A1/en not_active Abandoned
- 2009-10-09 KR KR1020117010557A patent/KR20110084910A/ko not_active Withdrawn
- 2009-10-09 US US12/576,388 patent/US8147710B2/en not_active Expired - Fee Related
- 2009-10-09 RU RU2011118429/04A patent/RU2011118429A/ru not_active Application Discontinuation
- 2009-10-09 JP JP2011531192A patent/JP2012505296A/ja active Pending
- 2009-10-09 WO PCT/US2009/060094 patent/WO2010042781A2/en not_active Ceased
- 2009-10-09 MX MX2011003633A patent/MX2011003633A/es active IP Right Grant
- 2009-10-09 AU AU2009302263A patent/AU2009302263A1/en not_active Abandoned
- 2009-10-09 EP EP09748568A patent/EP2331489A2/en not_active Withdrawn
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2012
- 2012-02-27 US US13/405,657 patent/US8518294B2/en not_active Expired - Fee Related
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