CN100558721C - 氟代环状碳酸酯的制备方法 - Google Patents
氟代环状碳酸酯的制备方法 Download PDFInfo
- Publication number
- CN100558721C CN100558721C CNB2007100415993A CN200710041599A CN100558721C CN 100558721 C CN100558721 C CN 100558721C CN B2007100415993 A CNB2007100415993 A CN B2007100415993A CN 200710041599 A CN200710041599 A CN 200710041599A CN 100558721 C CN100558721 C CN 100558721C
- Authority
- CN
- China
- Prior art keywords
- carbonate
- cyclic carbonate
- alkaline
- metal fluoride
- chloride
- 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.)
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- 150000005676 cyclic carbonates Chemical class 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 26
- 229910001618 alkaline earth metal fluoride Inorganic materials 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- -1 fluoro cyclic carbonate Chemical class 0.000 claims abstract description 13
- 239000002994 raw material Substances 0.000 claims abstract description 13
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 10
- 229910001512 metal fluoride Inorganic materials 0.000 claims abstract description 9
- 239000011541 reaction mixture Substances 0.000 claims abstract description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052728 basic metal Inorganic materials 0.000 claims description 8
- 150000003818 basic metals Chemical class 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 235000019270 ammonium chloride Nutrition 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 6
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 5
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 claims description 4
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 claims description 4
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 3
- HYVXSSVBGCVOKH-UHFFFAOYSA-M [NH4+].[Cl-].C(C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[Cl-] Chemical compound [NH4+].[Cl-].C(C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[Cl-] HYVXSSVBGCVOKH-UHFFFAOYSA-M 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 3
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 claims description 3
- VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 claims description 3
- QKBJDEGZZJWPJA-UHFFFAOYSA-N ethyl propyl carbonate Chemical compound [CH2]COC(=O)OCCC QKBJDEGZZJWPJA-UHFFFAOYSA-N 0.000 claims description 3
- KKQAVHGECIBFRQ-UHFFFAOYSA-N methyl propyl carbonate Chemical compound CCCOC(=O)OC KKQAVHGECIBFRQ-UHFFFAOYSA-N 0.000 claims description 3
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- AHIHJODVQGBOND-UHFFFAOYSA-N propan-2-yl hydrogen carbonate Chemical compound CC(C)OC(O)=O AHIHJODVQGBOND-UHFFFAOYSA-N 0.000 claims description 3
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 claims description 3
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 claims description 3
- 229910016036 BaF 2 Inorganic materials 0.000 claims description 2
- 229910004261 CaF 2 Inorganic materials 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000005586 carbonic acid group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 231100000004 severe toxicity Toxicity 0.000 abstract description 3
- 239000002360 explosive Substances 0.000 abstract 1
- 239000000706 filtrate Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 10
- 239000007789 gas Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000012634 fragment Substances 0.000 description 4
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- SBLRHMKNNHXPHG-UHFFFAOYSA-N 4-fluoro-1,3-dioxolan-2-one Chemical compound FC1COC(=O)O1 SBLRHMKNNHXPHG-UHFFFAOYSA-N 0.000 description 1
- RCXLKTHBRGGJEC-UHFFFAOYSA-N 4-fluoro-5-methylbenzene-1,3-dicarboxylic acid Chemical compound FC1=C(C=C(C(=O)O)C=C1C)C(=O)O RCXLKTHBRGGJEC-UHFFFAOYSA-N 0.000 description 1
- CYFHOUUMXLDUGR-UHFFFAOYSA-N ClC1=C(C=C(C(=O)O)C=C1C)C(=O)O Chemical compound ClC1=C(C=C(C(=O)O)C=C1C)C(=O)O CYFHOUUMXLDUGR-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- OYLGJCQECKOTOL-UHFFFAOYSA-L barium fluoride Chemical compound [F-].[F-].[Ba+2] OYLGJCQECKOTOL-UHFFFAOYSA-L 0.000 description 1
- 229910001632 barium fluoride Inorganic materials 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000010808 liquid waste Substances 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000005911 methyl carbonate group Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000007784 solid electrolyte Substances 0.000 description 1
- 239000002910 solid waste Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- XUVMLVYJXQOUJM-UHFFFAOYSA-M tetraethylazanium;fluoride;hydrofluoride Chemical compound [H+].[F-].[F-].CC[N+](CC)(CC)CC XUVMLVYJXQOUJM-UHFFFAOYSA-M 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings 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
- C07D317/42—Halogen atoms or nitro radicals
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/24—Nitrogen compounds
- B01J27/25—Nitrates
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0201—Oxygen-containing compounds
- B01J31/0204—Ethers
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
- H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
- H01M10/0566—Liquid materials
- H01M10/0569—Liquid materials characterised by the solvents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Electrochemistry (AREA)
- Manufacturing & Machinery (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Inorganic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
Description
Claims (9)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2007100415993A CN100558721C (zh) | 2007-06-01 | 2007-06-01 | 氟代环状碳酸酯的制备方法 |
JP2007236041A JP4789892B2 (ja) | 2007-06-01 | 2007-09-12 | フルオロ環状炭酸エステルの製造方法 |
KR1020070096779A KR100942901B1 (ko) | 2007-06-01 | 2007-09-21 | 불소 치환 환상 탄산 에스테르의 제조방법 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2007100415993A CN100558721C (zh) | 2007-06-01 | 2007-06-01 | 氟代环状碳酸酯的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101066965A CN101066965A (zh) | 2007-11-07 |
CN100558721C true CN100558721C (zh) | 2009-11-11 |
Family
ID=38879682
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB2007100415993A Active CN100558721C (zh) | 2007-06-01 | 2007-06-01 | 氟代环状碳酸酯的制备方法 |
Country Status (3)
Country | Link |
---|---|
JP (1) | JP4789892B2 (zh) |
KR (1) | KR100942901B1 (zh) |
CN (1) | CN100558721C (zh) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5135926B2 (ja) * | 2007-07-13 | 2013-02-06 | ダイキン工業株式会社 | 4−フルオロ−1,3−ジオキソラン−2−オンの製造方法 |
TW201105646A (en) * | 2009-05-28 | 2011-02-16 | Solvay Fluor Gmbh | Process for the preparation of 4-fluoro-4-R-5-R'-1,3-dioxolane-2-ones |
EP2454226B1 (en) | 2009-07-16 | 2017-03-22 | Solvay Fluor GmbH | Process for the preparation of fluoroalkyl (fluoro)alkyl carbonates |
CN101597275B (zh) * | 2009-07-16 | 2012-05-30 | 太仓华一化工科技有限公司 | 一种氟代碳酸亚乙酯的纯化方法 |
TW201121938A (en) * | 2009-09-28 | 2011-07-01 | Solvay Fluor Gmbh | Manufacture of difluoroethylene carbonate, trifluoroethylene carbonate and tetrafluoroethylene carbonate |
CN102766130A (zh) * | 2012-07-18 | 2012-11-07 | 太仓华一化工科技有限公司 | 一种二氟代碳酸乙烯酯的制备方法 |
CN102807549A (zh) * | 2012-08-13 | 2012-12-05 | 江苏华盛精化工股份有限公司 | 一种三氟甲基环状碳酸酯的制备方法 |
CN103113345B (zh) * | 2013-01-21 | 2014-11-05 | 张家港瀚康化工有限公司 | 氟代碳酸乙烯酯的制备方法 |
CN104072473B (zh) * | 2014-07-08 | 2016-04-06 | 昆明合起工贸有限公司 | 一种用氟硅酸合成氟代碳酸乙烯酯的生产工艺 |
CN106916136B (zh) * | 2017-03-01 | 2019-06-14 | 山东永浩新材料科技有限公司 | 一种氟代碳酸乙烯酯的合成方法 |
CN114736185B (zh) * | 2022-04-21 | 2024-01-02 | 上海东庚化工技术有限公司 | 一种超纯氟代碳酸乙烯酯节能生产工艺及*** |
WO2023201999A1 (zh) * | 2022-04-21 | 2023-10-26 | 上海东庚化工技术有限公司 | 一种电解液添加剂的生产方法及*** |
CN115626907B (zh) * | 2022-11-03 | 2024-04-16 | 多氟多新材料股份有限公司 | 一种4-三氟代甲基碳酸乙烯酯的制备方法 |
CN115611846B (zh) * | 2022-11-10 | 2024-07-09 | 广州理文科技有限公司 | 一种高纯度碳酸乙烯酯氟代衍生物的制备方法 |
CN115772150A (zh) * | 2022-11-10 | 2023-03-10 | 广州理文科技有限公司 | 一种碳酸乙烯酯氟代衍生物的制备方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH09286785A (ja) * | 1996-01-10 | 1997-11-04 | Sanyo Chem Ind Ltd | 含フッ素ジオキソラン、電解液用有機溶媒、リチウム二次電池および電気二重層コンデンサ |
US7435842B2 (en) | 2001-12-27 | 2008-10-14 | Asahi Kasei Chemicals Corporation | Process for producing carbonic ester |
JP4848684B2 (ja) * | 2005-06-28 | 2011-12-28 | セントラル硝子株式会社 | 高純度の4−フルオロ−1,3−ジオキソラン−2−オンの製造方法 |
JP4848683B2 (ja) * | 2005-06-28 | 2011-12-28 | セントラル硝子株式会社 | 高純度の4−フルオロ−1,3−ジオキソラン−2−オンの製造方法 |
JP5061635B2 (ja) * | 2007-02-15 | 2012-10-31 | ダイキン工業株式会社 | 4−フルオロ−1,3−ジオキソラン−2−オンの製造法 |
-
2007
- 2007-06-01 CN CNB2007100415993A patent/CN100558721C/zh active Active
- 2007-09-12 JP JP2007236041A patent/JP4789892B2/ja active Active
- 2007-09-21 KR KR1020070096779A patent/KR100942901B1/ko active IP Right Grant
Also Published As
Publication number | Publication date |
---|---|
JP4789892B2 (ja) | 2011-10-12 |
KR100942901B1 (ko) | 2010-02-16 |
JP2008297299A (ja) | 2008-12-11 |
CN101066965A (zh) | 2007-11-07 |
KR20080105955A (ko) | 2008-12-04 |
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