CN1286245A - 稳定的(cf3) 2n-盐及其制备方法 - Google Patents
稳定的(cf3) 2n-盐及其制备方法 Download PDFInfo
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- CN1286245A CN1286245A CN00126092A CN00126092A CN1286245A CN 1286245 A CN1286245 A CN 1286245A CN 00126092 A CN00126092 A CN 00126092A CN 00126092 A CN00126092 A CN 00126092A CN 1286245 A CN1286245 A CN 1286245A
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- 238000000034 method Methods 0.000 title claims description 14
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 20
- 229910005965 SO 2 Inorganic materials 0.000 claims description 19
- -1 alkali metal salt Chemical class 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 229910052698 phosphorus Inorganic materials 0.000 claims description 11
- 229910052787 antimony Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 229910052785 arsenic Inorganic materials 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 150000001721 carbon Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000005077 polysulfide Substances 0.000 claims description 3
- 229920001021 polysulfide Polymers 0.000 claims description 3
- 150000008117 polysulfides Polymers 0.000 claims description 3
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 229910017008 AsF 6 Inorganic materials 0.000 claims description 2
- 229910020366 ClO 4 Inorganic materials 0.000 claims description 2
- 229910018286 SbF 6 Inorganic materials 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 229910052728 basic metal Inorganic materials 0.000 claims description 2
- 150000003818 basic metals Chemical class 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 2
- 239000003495 polar organic solvent Substances 0.000 claims 3
- 239000002243 precursor Substances 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 22
- 239000000460 chlorine Substances 0.000 description 21
- 229910052731 fluorine Inorganic materials 0.000 description 16
- 229910052801 chlorine Inorganic materials 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 229910052794 bromium Inorganic materials 0.000 description 12
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 11
- 229910052744 lithium Inorganic materials 0.000 description 11
- 239000002245 particle Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 238000004821 distillation Methods 0.000 description 6
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 125000005561 phenanthryl group Chemical group 0.000 description 5
- 125000003226 pyrazolyl group Chemical group 0.000 description 5
- 125000004076 pyridyl group Chemical group 0.000 description 5
- 238000004293 19F NMR spectroscopy Methods 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- FGDZQCVHDSGLHJ-UHFFFAOYSA-M rubidium chloride Chemical compound [Cl-].[Rb+] FGDZQCVHDSGLHJ-UHFFFAOYSA-M 0.000 description 4
- 238000001035 drying Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
- 229910015015 LiAsF 6 Inorganic materials 0.000 description 2
- 229910013063 LiBF 4 Inorganic materials 0.000 description 2
- 229910013684 LiClO 4 Inorganic materials 0.000 description 2
- 229910013872 LiPF Inorganic materials 0.000 description 2
- 101150058243 Lipf gene Proteins 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 230000000887 hydrating effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229960003742 phenol Drugs 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- JAAGVIUFBAHDMA-UHFFFAOYSA-M rubidium bromide Chemical compound [Br-].[Rb+] JAAGVIUFBAHDMA-UHFFFAOYSA-M 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-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
- 229910002441 CoNi Inorganic materials 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- UOHUDFHWFDUDID-UHFFFAOYSA-N [Cl].C[SiH](C)C Chemical compound [Cl].C[SiH](C)C UOHUDFHWFDUDID-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000004176 ammonification Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- PSHMSSXLYVAENJ-UHFFFAOYSA-N dilithium;[oxido(oxoboranyloxy)boranyl]oxy-oxoboranyloxyborinate Chemical compound [Li+].[Li+].O=BOB([O-])OB([O-])OB=O PSHMSSXLYVAENJ-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000007770 graphite material Substances 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910001411 inorganic cation Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229910021518 metal oxyhydroxide Inorganic materials 0.000 description 1
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 1
- 239000011255 nonaqueous electrolyte Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000005412 pyrazyl group Chemical group 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
Classifications
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- 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
- H01M10/0568—Liquid materials characterised by the solutes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/15—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/62—Quaternary ammonium compounds
- C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/65—Metal complexes of amines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
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- 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
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- 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
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Abstract
本发明涉及稳定的(CF3)2N-盐、其制备方法及其作为有机化合物的前体的应用。
Description
本发明涉及稳定的(CF3)2N-盐、其制备方法、及其作为有机化合物的前体的应用。
锂离子电池是最有希望用于移动场合的体系。其应用领域由优质电子器件(如,移动电话、摄录机)延伸至用于电动汽车的电池。
这些电池由阴极、阳极、隔板和非水电解质组成。所用阴极通常为Li(MnMez)O4、Li(CoMez)O2、Li(CoNixMez)O2、或其它的锂嵌入和***化合物。阳极可由金属锂、碳材料、石墨、石墨碳材料或其它的锂嵌入和***化合物或合金化合物组成。所用电解质为在非质子传递溶剂中包含锂盐,如LiPF6、LiBF4、LiClO4、LiAsF6、LiCF3SO3、LiN(CF3SO2)2或LiC(CF3SO2)3及其混合物的溶液。
在研究用于电池的新型盐的过程中,二(三氟甲基)胺类物质被证实是合适的。
文献中首次描述的来自二(三氟甲基)胺类的一种盐为二(三氟甲基)氨化铯。该盐可通过将全氟(2-氮杂丙烷)加入氟化铯与无水乙腈的悬浮液中而制成。Minkwitz(无机化学(Inorg.Chem.),28(1989),1627-1630)分离出Cs+ -N(CF3)2,但不是(C6H5)4As+(CF3)2N-,也不是(C2H5)4N+(CF3)2N-。
欧洲专利申请99101982描述了一种制备具有无机阳离子的(CF3)2N-阴离子的新方法。该盐仅在溶液中稳定,因此必须立即使用。
因此,本发明的目的是提供稳定的(CF3)2N-盐及其制备方法。
本发明的目的通过具有以下通式的化合物而实现:
[([R1(CR2R3)k]lAx)yKt]+ -N(CF3)2 (Ⅰ)其中:Kt为N、P、As、Sb、S或Se,
A为N、P、P(O)、O、S、S(O)、SO2、As、As(O)、Sb或Sb(O),
R1、R2和R3相同或不同且分别为H、卤素、取代和/或未取代烷基CnH2n+1、具有1-18个碳原子和一个或多个双键的取代和/或未取代链烯基、具有1-18个碳原子和一个或多个三键的取代和/或未取代炔基、取代和/或未取代环烷基CmH2m-1、单-或多取代和/或未取代苯基、取代和/或未取代杂芳基,
A可按各种位置包括在R1、R2和/或R3中,
Kt可包括在环或杂环中,
键接到Kt上的基团可以相同或不同,
其中:
n为1-18
m为3-7
k为0或1-6
l为1或2(如果x=1)和1(如果x=0)
x为0或1
y为1-4。
该化合物可用作将N(CF3)2基团引入有机物质中的试剂。例如,可以制备出用于二次电池和原电池的氟化溶剂。
惊人地发现,这些盐还具有其它的可能用途。这种新型盐作为用于制备液晶化合物的前体是有价值的,这归因于其结构。
已经发现,可在温和条件下简单地制备出配位化合物。该盐可高产率地分离。
已经惊人地发现,这种新型盐是稳定的。它们可在室温下分离并储存。
以下更详细地解释本发明的一个一般例子。
具有以下通式的化合物:
D+ -N(CF3)2 (Ⅱ)
其中D+选自碱金属,可通过欧洲专利申请No.99101982所述的方法来制备。其它合适的N(CF3)2-基团的提供者是具有以下通式的化合物:
GN(CF3)2 (Ⅳ)
其中G选自氟化磺酰胺和氟化酰胺。
首先装入通式(Ⅱ)或(Ⅳ)化合物在选自乙腈、二乙氧基乙烷和二甲基甲酰胺的合适极性有机溶剂中的溶液。在-40℃至80℃的温度下,优选在室温下,加入等摩尔量的具有以下通式的盐:
[([R1(CR2R3)k]lAx)yKt]+ -E (Ⅲ)
其中:
Kt=N、P、As、Sb、S或Se,
A=N、P、P(O)、O、S、S(O)、SO2、As、As(O)、Sb或Sb(O),
R1、R2和R3相同或不同且分别为H、卤素、取代和/或未取代烷基CnH2n+1、具有1-18个碳原子和一个或多个双键的取代和/或未取代链烯基、具有1-18个碳原子和一个或多个三键的取代和/或未取代炔基、取代和/或未取代环烷基CmH2m-1、单-或多取代和/或未取代苯基、取代和/或未取代杂芳基,
A可按各种位置包括在R1、R2和/或R3中,
Kt可包括在环或杂环中,
键接到Kt上的基团可以相同或不同,
其中:
n为1-18
m为3-7
k为0或1-6
l为1或2(如果x=1)和1(如果x=0)
x为0或1
y为1-4,
且-E=F-、Cl-、Br-、I-、BF4 -、ClO4 -、AsF6 -、SbF6 -、或PF6 -。
通过施加减压,去除可能形成的所有挥发性副产物。但所形成的副产物通常是不溶于这些溶剂并被过滤掉的盐。
在减压下去除溶剂。所得反应产物的产率超过80%。大多数盐在室温下是稳定的且不会熔化分解。
这种新型化合物可用于包含常规导电盐的电解质。合适的电解质的例子为包含选自LiPF6、LiBF4、LiClO4、LiAsF6、LiCF3SO3、LiN(CF3SO2)2和LiC(CF3SO2)3及其混合物的导电盐的那些。这些电解质还可包含有机异氰酸酯(DE 199 44 603)以降低水含量。另外,这些电解质可包含有机碱金属盐(DE 199 10 968)作为添加剂。合适的碱金属盐为具有以下通式的碱金属硼酸盐:
Li+B-(OR1)m(OR2)p
其中:
m和p为0、1、2、3或4且m+p=4,且
R1和R2相同或不同,根据需要通过单键或双键相互直接连接,而且在每种情况下单独或共同为芳族或脂族羧酸、二羧酸或磺酸基团,或在每种情况下单独或共同为可未取代或被A或Hal单取代至四取代的选自苯基、萘基、蒽基和菲基的芳环,或在每种情况下单独或共同为可未取代或被A或Hal单取代至三取代的选自吡啶基、吡唑基(pyrazyl)或联吡啶基的杂环芳环,或在每种情况下单独或共同为可未取代或被A或Hal单取代至四取代的选自芳族羟基羧酸和芳族羟基磺酸的芳族羟基酸,
且Hal为F、Cl或Br,
且A为具有1-6个碳原子的可被单卤化至三卤化的烷基。另外合适的是具有以下通式的碱金属醇盐:
Li+OR-
其中R为芳族或脂族羧酸、二羧酸或磺酸基团,或为可未取代或被A或Hal单取代至四取代的选自苯基、萘基、蒽基和菲基的芳环,或为可未取代或被A或Hal单取代至三取代的选自吡啶基、吡唑基或联吡啶基的杂环芳环,或为可未取代或被A或Hal单取代至四取代的选自芳族羟基羧酸和芳族羟基磺酸的芳族羟基酸,
且Hal为F、Cl或Br,
且A为具有1-6个碳原子的可被单卤化至三卤化的烷基。
具有以下结构式的锂配盐也可存在于电解质中:
其中:
R1和R2相同或不同,如果需要通过单键或双键相互直接连接,而且在每种情况下单独或共同为可未取代或被烷基(C1-C6)、烷氧基(C1-C6)或卤素(F、Cl、Br)单取代至六取代的选自苯基、萘基、蒽基和菲基的芳环,或在每种情况下单独或共同为可未取代或被烷基(C1-C6)、烷氧基(C1-C6)或卤素(F、Cl、Br)单取代至四取代的选自吡啶基、吡唑基或嘧啶基的芳族杂环,或在每种情况下单独或共同为可未取代或被烷基(C1-C6)、烷氧基(C1-C6)或卤素(F、Cl、Br)单取代至四取代的选自羟基苯羧基、羟基萘羧基、羟基苯磺酰基和羟基萘磺酰基的芳环,
R3-R6在每种情况下单独或成双地,如果需要通过单键或双键相互直接连接,具有以下含义:
1.烷基(C1-C6)、烷氧基(C1-C6)或卤素(F、Cl、Br)
2.选自以下的芳环:
可未取代或被烷基(C1-C6)、烷氧基(C1-C6)或卤素(F、Cl、Br)单取代至六取代的苯基、萘基、蒽基和菲基,
可未取代或被烷基(C1-C6)、烷氧基(C1-C6)或卤素(F、Cl、Br)单取代至四取代的吡啶基、吡唑基或嘧啶基,
该盐可通过以下方法(DE 199 32 317)制成:
a)将3-、4-、5-、6-取代酚在合适溶剂中与氯磺酸进行混合,
b)将来自a)的中间体与氯三甲基硅烷进行反应,然后将产物过滤并进行分馏,
c)将来自b)的中间体与四甲氧基硼酸锂(1-)在合适溶剂中进行反应,然后从中分离出最终产物。
但也可使用这样的电解质,其中包含具有以下通式的化合物(DE 19953 638):
X-(CYZ)m-SO2N(CR1R2R3)2
其中:
X为H、F、Cl、CnF2n+1、CnF2n-1、或(SO2)kN(CR1R2R3)2,
Y为H、F或Cl
Z为H、F或Cl
R1、R2和R3为H和/或烷基、氟代烷基或环烷基
m为0-9且如果X=H,m不为0
n为1-9
k为0(如果m=0)和k为1(如果m=1-9),
该化合物通过将部分氟化或全氟化的烷基磺酰氟与二甲基胺在有机溶剂中进行反应而制成,以及具有以下通式的配盐(DE 199 51 804):
其中:
x、y为1、2、3、4、5或6
Mx+为金属离子
E为路易斯酸,选自BR1R2R3、AlR1R2R3、PR1R2R3R4R5、AsR1R2R3R4R5和VR1R2R3R4R5,
R1-R5相同或不同,如果需要通过单键或双键相互直接连接,而且在每种情况下单独或共同为:
卤素(F、Cl、Br),
可被F、Cl、Br部分或完全取代的烷基或烷氧基(C1-C8),
可未取代或被烷基(C1-C8)或F、Cl、Br单取代至六取代的选自苯基、萘基、蒽基和菲基的芳环,如果需要通过氧键接,
可未取代或被烷基(C1-C8)或F、Cl、Br单取代至四取代的选自吡啶基、吡唑基和嘧啶基的芳族杂环,根据需要通过氧键接,且
Z为OR6、NR6R7、CR6R7R8、OSO2R6、N(SO2R6)(SO2R7)、C(SO2R6)(SO2R7)(SO2R8)或OCOR6,其中:
R6-R8相同或不同,根据需要通过单键或双键相互直接连接,且在每种情况下单独或共同为:
氢原子或定义如R1-R5,该化合物通过将相应硼或磷路易斯酸-溶剂加成物与锂或四烷基铵酰亚胺、甲烷化物(methanide)或三氟甲磺酸盐(triflate)进行反应而制成。
其中:
M为金属离子或四烷基铵离子,
x、y为1、2、3、4、5或6,
R1-R4相同或不同地为烷氧基或羧基(C1-C8),可通过单键或双键相互直接键接。这些硼酸盐通过将四烷氧基硼酸锂或烷醇锂与硼酸酯的1∶1混合物在非质子传递溶剂中与合适的羟基或羧基化合物,按照2∶1或4∶1的比率进行反应而制成。
这种新型化合物还可用于包含通式(Ⅰ)氟烷基磷酸锂的电解质:
Li+[PFx(CyF2y+1-zHz)6-x]- (Ⅰ)
其中:
1=x=5
3=y=8
0=z=2y+1
且配体(CyF2y+1-zHz)可相同或不同,但排除具有通式(Ⅰ’)的化合物:Li+[PFa(CHbFc(CF3)d)e]-(Ⅰ′)
其中a为2-5的整数,b=0或1,c=0或1,d=2,且
e为1-4的整数,前提是b和c不同时为0且a+e的总和为6,且配体(CHbFc(CF3)d)可以相同或不同(DE 100 08 955)。制备通式(Ⅰ)氟烷基磷酸锂的方法的特征在于,将至少一种具有以下通式的化合物:
HmP(CnH2n+1)3-m (Ⅲ),
OP(CnH2n+1)3 (Ⅳ),
ClmP(CnH2n+1)3-m (Ⅴ),
FmP(CnH2n+1)3-m (Ⅵ),
CloP(CnH2n+1)5-o (Ⅶ)或
FoP(CnH2n+1)5-o (Ⅷ),
其中,在每种情况下,
0<m<2、3<n<8且0<o<4,
通过在氟化氢中进行电解而氟化,将所得的氟化产物混合物通过萃取、相分离和/或蒸馏进行分级,然后将所得氟化烷基正膦与氟化锂在非质子传递溶剂或溶剂混合物中,在没有水分的存在下进行反应,然后将具有通式(Ⅰ)的所得盐通过常规方法进行纯化和分离。
这种新型化合物还可用于包含下式盐的电解质:
Li[P(OR1)a(OR2)b(OR3)c(OR4)dFe]其中0<a+b+c+d≤5且a+b+c+d+e=6,且R1-R4分别独立地为烷基、芳基或杂芳基,其中至少两个R1-R4可通过单键或双键相互直接连接(DE100 16 801)。这些化合物通过将具有以下结构式的磷(Ⅴ)化合物与氟化锂在有机溶剂的存在下反应制成:P(OR1)a(OR2)b(OR3)c(OR4)dFe
其中0<a+b+c+d≤5且a+b+c+d+e=5,且R1-R4定义如上。
这种新型化合物可用于电化学电池的电解质中,该电池包括由选自Sb、Bi、Cd、In、Pb、Ga和锡或其合金的涂覆金属芯组成的阳极材料(DE 100 16 024)。制备所述阳极材料的方法的特征在于:
a)将所述金属芯或合金芯的悬浮液或溶胶在乌洛托品中制成,
b)用C5-C12-烃乳化该悬浮液,
c)将该乳液沉淀到金属芯或合金芯上,然后
d)通过将该体系进行热处理,将金属氢氧化物或羟基氧化物转化成相应的氧化物。
这种新型化合物还可用于电化学电池的电解质中,该电池包括由常规锂嵌入和***化合物组成的阴极、或由锂混合氧化物颗粒组成的阴极材料,其中所述锂混合氧化物颗粒通过将颗粒悬浮在有机溶剂中,将该悬浮液与可水解金属化合物的溶液和水解溶液进行混合,然后过滤、干燥并根据需要煅烧该涂覆颗粒而涂覆有一种或多种金属氧化物(DE 199 22 522)。它们还可由涂覆有一种或多种聚合物的锂混合氧化物颗粒(DE 199 46 066)组成,所述颗粒通过这样一种方法而得到,其中:将颗粒悬浮在溶剂中,随后将涂覆颗粒过滤、干燥并根据需要进行煅烧。另外,这种新型化合物可用于包括阴极的体系,该阴极由单独地或多重地涂有碱金属化合物和金属氧化物的锂混合氧化物颗粒(DE100 14 884)组成。制备这些材料的方法的特征在于,将颗粒悬浮在有机溶剂中,加入悬浮在有机溶剂中的碱金属盐化合物,加入溶解在有机溶剂中的金属氧化物,将该悬浮液与水解溶液进行混合,然后将涂覆颗粒过滤、干燥并煅烧。
具有通式(Ⅰ)的反应产物还可用作各种试剂中的N(CF3)2基团提供者。另外,它们可用作液晶的前体。
将等摩尔量的选自卤代乙酸烷基酯的化合物(优选溴乙酸乙酯)加入溶解在合适溶剂中的按照本发明制成的结构式(Ⅰ)化合物中。将该混合物回流1-4小时,优选2小时。加入水,然后使用合适的有机溶剂萃取有机相。将萃取液干燥,随后蒸馏去除溶剂。
以下实施例用于更详细说明本发明而非限定之。
实施例
实施例1
在室温下,在搅拌下,将4.63克(19.5毫摩尔)Rb+-N(CF3)2(由2.04克(19.5毫摩尔)RbF和5.56克(19.5毫摩尔)CF3SO2N(CF3)2在20厘米3无水乙腈中制成)的溶液加入6.40克(19.4毫摩尔)(C4H9)4N+BF4 -在5厘米3无水乙腈中的溶液。过滤出沉淀RbBF4,然后用无水乙腈洗涤。减压去除溶剂,然后分离出7.5克白色粉末。
(C4H9)4N+-N(CF3)2的产率为98%。
分析:
实测值: 计算值:
C 54.67 54.80
H 9.56 9.20
F 28.70 28.90
N 7.15 7.10
19F NMR(CCl3F):-38.32s(溶剂:CH3CN)、-37.66s(溶剂:CD2Cl2);熔点:123-125℃。
实施例2
在室温下,将0.568克(2.39毫摩尔)Rb+-N(CF3)2(由0.25克(2.39毫摩尔)RbF和0.69克(2.39毫摩尔)CF3SO2N(CF3)2在2厘米3无水乙腈中制成)的溶液加入0.66克(2.37毫摩尔)(C4H9)4N+Cl-在1厘米3无水乙腈中的溶液。过滤出沉淀RbCl,然后用无水乙腈洗涤。减压蒸馏去除溶剂,然后分离出0.77克白色粉末。(C4H9)4N+-N(CF3)2的产率为82.2%。
19F NMR光谱与实施例1所得相同。
实施例3
在室温下,将0.62克(2.61毫摩尔)RB+-N(CF3)2(由0.273克(2.61毫摩尔)RbF和0.75克(2.63毫摩尔)CF3SO2N(CF3)2在2厘米3无水乙腈中制成)的溶液加入0.883克(2.60毫摩尔)(C4H9)4P+Br-在1厘米3无水乙腈中的溶液。过滤出沉淀RbBr,然后用无水乙腈洗涤。减压蒸馏去除溶剂,然后分离出0.97克白色粉末。(C4H9)4P+-N(CF3)2的产率为90.7%。
19F NMR(CCl3F):-36.49s(溶剂:CH3CN);熔点:85-86℃。
实施例4
在室温下,将0.522克(2.20毫摩尔)Rb+-N(CF3)2(由0.23克(2.20毫摩尔)RbF和0.63克(2.21毫摩尔)CF3SO2N(CF3)2在3厘米3无水乙腈中制成)的溶液与0.84克(2.16毫摩尔)Rh3(PhCH2)P+Cl-在1厘米3无水乙腈中的悬浮液进行混合,并搅拌10分钟。过滤出沉淀RbCl,然后用无水乙腈洗涤。减压蒸馏去除溶剂,然后分离出0.96克白色粉末。Ph3(PhCH2)P+-N(CF3)2的产率为88.0%。
19F NMR(CCl3F):-36.66s(溶剂:CH3CN);
熔点:114-115℃。
实施例5
在-40℃下,将0.017克(0.18毫摩尔)(CH3)4N+F-在0.5厘米3无水二氯甲烷中的溶液与0.052克(0.18毫摩尔)CF3SO2N(CF3)2进行混合。将反应溶液加热至室温,用相同量的无水乙腈稀释,然后用19F NMR光谱进行分析。所观察到的信号属于盐(CH3)4N+-N(CF3)2。在干燥的氩气气氛下蒸馏去除溶剂,然后分离出0.037克白色、高吸湿性材料。产率为90.2%。
19F NMR(CCl3F):-40.8s;熔点:120-125℃。
实施例6
将0.837克(2.12毫摩尔)(C4H9)4N+-N(CF3)2在2厘米3无水二氯甲烷中的溶液与0.271克(1.62毫摩尔)BrCH2COOC2H5进行混合。将该混合物回流2小时。加入水,然后每次用10厘米3二氯甲烷萃取有机相3次。将萃取液在MgSO4上干燥,然后蒸馏去除溶剂。所得产物(CF3)2NCH2COOC2H5由GC证实。产率为93.3%。
Claims (7)
1.具有以下通式的化合物:
[([R1(CR2R3)k]lAx)yKt]+ -N(CF3)2 (Ⅰ)
其中:
Kt为N、P、As、Sb、S或Se,
A为N、P、P(O)、O、S、S(O)、SO2、As、As(O)、Sb或Sb(O),
R1、R2和R3相同或不同且分别为H、卤素、取代和/或未取代烷基CnH2n+1、具有1-18个碳原子和一个或多个双键的取代和/或未取代链烯基、具有1-18个碳原子和一个或多个三键的取代和/或未取代炔基、取代和/或未取代环烷基CmH2m-1、单-或多取代和/或未取代苯基、取代和/或未取代杂芳基,
A可按各种位置包括在R1、R2和/或R3中,
Kt可包括在环或杂环中,
键接到Kt上的基团可以相同或不同,
其中:
n为1-18
m为3-7
k为0或1-6
l为1或2(如果x=1)和1(如果x=0)
x为0或1
y为1-4。
2.制备根据权利要求1的化合物的方法,其特征在于,将具有以下通式的碱金属盐
D+ -N(CF3)2 (Ⅱ)
中D+选自碱金属,在极性有机溶剂中与具有以下通式的盐进行反应:
[([R2(CR2R3)k]lAx)yKt]+ -E (Ⅲ)其中:
Kt、A、R1、R2、R3、k、l、x和y定义如权利要求1,且
-E为F-、Cl-、Br-、I-、BF4 -、ClO4 -、AsF6 -、SbF6 -、或PF6 -。
3.根据权利要求2的制备权利要求1化合物的方法,其特征在于,将具有以下通式的化合物:
GN(CF3)2 (Ⅳ)
其中G选自氟化磺酰胺和氟化酰胺,在极性有机溶剂中与其中-E=F-的通式(Ⅲ)化合物进行反应。
4.根据权利要求2和3的制备权利要求1化合物的方法,其特征在于,所述反应在-40℃至80℃的温度下进行。
5.根据权利要求2-4的制备权利要求1化合物的方法,其特征在于,所述反应在选自乙腈、二乙氧基乙烷和二甲基甲酰胺的极性有机溶剂中进行。
6.通式(Ⅰ)化合物作为将N(CF3)2基团引入有机化合物的试剂的应用。
7.通式(Ⅰ)化合物在制备液晶化合物中的应用。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19941566A DE19941566A1 (de) | 1999-09-01 | 1999-09-01 | Stabile (CF3)2N-Salze und Verfahren zu deren Herstellung |
DE19941566.8 | 1999-09-01 |
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CN201110193754XA Division CN102351717A (zh) | 1999-09-01 | 2000-08-31 | 稳定的(cf3)2n-盐及其制备方法 |
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CN00126092A Pending CN1286245A (zh) | 1999-09-01 | 2000-08-31 | 稳定的(cf3) 2n-盐及其制备方法 |
CN201110193754XA Pending CN102351717A (zh) | 1999-09-01 | 2000-08-31 | 稳定的(cf3)2n-盐及其制备方法 |
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US (1) | US6582849B1 (zh) |
EP (1) | EP1081129B1 (zh) |
JP (1) | JP4638006B2 (zh) |
KR (1) | KR100685563B1 (zh) |
CN (2) | CN1286245A (zh) |
BR (1) | BR0003885A (zh) |
CA (1) | CA2317284A1 (zh) |
DE (2) | DE19941566A1 (zh) |
RU (1) | RU2257376C2 (zh) |
TW (1) | TWI221832B (zh) |
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EP1205998A2 (de) | 2000-11-10 | 2002-05-15 | MERCK PATENT GmbH | Elektrolyte |
DE10055811A1 (de) | 2000-11-10 | 2002-05-29 | Merck Patent Gmbh | Tetrakisfluoroalkylborat-Salze und deren Verwendung als Leitsalze |
DE10107118A1 (de) | 2001-02-14 | 2002-08-29 | Merck Patent Gmbh | Verfahren zur Herstellung von Bis(trifluormethyl)imido-Salzen |
DE10258671A1 (de) | 2002-12-13 | 2004-06-24 | Merck Patent Gmbh | Ionische Flüssigkeiten mit [N(CF3)2]-Anionen |
US7541492B2 (en) * | 2005-10-26 | 2009-06-02 | Toyota Jidosha Kabushiki Kaisha | Perfluoroalkanesulfonamide compounds |
CA2630785C (en) * | 2005-12-02 | 2013-07-30 | Kanto Denka Kogyo Co., Ltd. | Ionic liquid containing phosphonium cation having p-n bond and method for producing same |
US20070129568A1 (en) * | 2005-12-06 | 2007-06-07 | Ngimat, Co. | Ionic liquids |
DE102006031149A1 (de) | 2006-07-04 | 2008-01-10 | Merck Patent Gmbh | Fluortenside |
DE102006032391A1 (de) * | 2006-07-04 | 2008-01-17 | Merck Patent Gmbh | Fluortenside |
DE102006031143A1 (de) * | 2006-07-04 | 2008-01-24 | Merck Patent Gmbh | Fluortenside |
DE102006031151A1 (de) | 2006-07-04 | 2008-01-10 | Merck Patent Gmbh | Fluortenside |
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DE3909802A1 (de) * | 1988-07-27 | 1990-04-05 | Merck Patent Gmbh | Difluormethylverbindungen |
DE4011812A1 (de) * | 1990-04-12 | 1991-10-17 | Consortium Elektrochem Ind | Tetrasubstituierte methane mit fluessigkristallinen eigenschaften |
US5827602A (en) | 1995-06-30 | 1998-10-27 | Covalent Associates Incorporated | Hydrophobic ionic liquids |
-
1999
- 1999-09-01 DE DE19941566A patent/DE19941566A1/de not_active Withdrawn
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2000
- 2000-08-28 DE DE50004137T patent/DE50004137D1/de not_active Expired - Lifetime
- 2000-08-28 EP EP00118126A patent/EP1081129B1/de not_active Expired - Lifetime
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- 2000-08-30 CA CA002317284A patent/CA2317284A1/en not_active Abandoned
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JP4638006B2 (ja) | 2011-02-23 |
RU2257376C2 (ru) | 2005-07-27 |
KR100685563B1 (ko) | 2007-02-22 |
KR20010067135A (ko) | 2001-07-12 |
JP2001122834A (ja) | 2001-05-08 |
EP1081129B1 (de) | 2003-10-22 |
US6582849B1 (en) | 2003-06-24 |
CA2317284A1 (en) | 2001-03-01 |
EP1081129A3 (de) | 2001-03-21 |
DE50004137D1 (de) | 2003-11-27 |
DE19941566A1 (de) | 2001-03-08 |
CN102351717A (zh) | 2012-02-15 |
BR0003885A (pt) | 2001-04-03 |
EP1081129A2 (de) | 2001-03-07 |
TWI221832B (en) | 2004-10-11 |
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