CA2164124A1 - Process for obtaining highly purified phosphatidylcholine - Google Patents
Process for obtaining highly purified phosphatidylcholineInfo
- Publication number
- CA2164124A1 CA2164124A1 CA002164124A CA2164124A CA2164124A1 CA 2164124 A1 CA2164124 A1 CA 2164124A1 CA 002164124 A CA002164124 A CA 002164124A CA 2164124 A CA2164124 A CA 2164124A CA 2164124 A1 CA2164124 A1 CA 2164124A1
- Authority
- CA
- Canada
- Prior art keywords
- phosphatidylcholine
- phosphatides
- gum
- lecithin
- product
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 73
- 239000008349 purified phosphatidyl choline Substances 0.000 title claims abstract description 18
- 239000000787 lecithin Substances 0.000 claims abstract description 45
- 235000010445 lecithin Nutrition 0.000 claims abstract description 45
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims abstract description 39
- 229940067606 lecithin Drugs 0.000 claims abstract description 39
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229960001231 choline Drugs 0.000 claims abstract description 18
- 235000010469 Glycine max Nutrition 0.000 claims abstract description 10
- 244000068988 Glycine max Species 0.000 claims abstract description 10
- 239000000463 material Substances 0.000 claims abstract description 10
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 43
- 239000000047 product Substances 0.000 claims description 38
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 23
- 238000000926 separation method Methods 0.000 claims description 15
- 239000010409 thin film Substances 0.000 claims description 15
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 14
- 235000021588 free fatty acids Nutrition 0.000 claims description 9
- 125000005456 glyceride group Chemical group 0.000 claims description 8
- 150000002576 ketones Chemical class 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000839 emulsion Substances 0.000 claims description 5
- 239000002244 precipitate Substances 0.000 claims description 5
- 238000001556 precipitation Methods 0.000 claims description 5
- 238000011084 recovery Methods 0.000 claims description 4
- 230000001376 precipitating effect Effects 0.000 claims 2
- 239000002031 ethanolic fraction Substances 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 239000007858 starting material Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 150000003626 triacylglycerols Chemical class 0.000 description 6
- CFWRDBDJAOHXSH-SECBINFHSA-N 2-azaniumylethyl [(2r)-2,3-diacetyloxypropyl] phosphate Chemical compound CC(=O)OC[C@@H](OC(C)=O)COP(O)(=O)OCCN CFWRDBDJAOHXSH-SECBINFHSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000003463 adsorbent Substances 0.000 description 4
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000002502 liposome Substances 0.000 description 3
- 150000003905 phosphatidylinositols Chemical class 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 2
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 229910052593 corundum Inorganic materials 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 238000001030 gas--liquid chromatography Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 2
- 229960000367 inositol Drugs 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- -1 magnetic tapes Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 150000008105 phosphatidylcholines Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 229910001845 yogo sapphire Inorganic materials 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- SUHOOTKUPISOBE-UHFFFAOYSA-N O-phosphoethanolamine Chemical compound NCCOP(O)(O)=O SUHOOTKUPISOBE-UHFFFAOYSA-N 0.000 description 1
- 102000003867 Phospholipid Transfer Proteins Human genes 0.000 description 1
- 108090000216 Phospholipid Transfer Proteins Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000012675 alcoholic extract Substances 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 210000001557 animal structure Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000008344 egg yolk phospholipid Substances 0.000 description 1
- 229940068998 egg yolk phospholipid Drugs 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 235000004626 essential fatty acids Nutrition 0.000 description 1
- 239000000469 ethanolic extract Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000008350 hydrogenated phosphatidyl choline Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000003127 radioimmunoassay Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
- C07F9/103—Extraction or purification by physical or chemical treatment of natural phosphatides; Preparation of compositions containing phosphatides of unknown structure
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/077,684 US5453523A (en) | 1993-06-16 | 1993-06-16 | Process for obtaining highly purified phosphatidylcholine |
| US08/077,684 | 1993-06-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2164124A1 true CA2164124A1 (en) | 1994-12-22 |
Family
ID=22139489
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002164124A Abandoned CA2164124A1 (en) | 1993-06-16 | 1994-06-16 | Process for obtaining highly purified phosphatidylcholine |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US5453523A (OSRAM) |
| EP (1) | EP0703918B1 (OSRAM) |
| JP (1) | JPH08511547A (OSRAM) |
| AU (1) | AU7110694A (OSRAM) |
| CA (1) | CA2164124A1 (OSRAM) |
| DE (1) | DE69426114T2 (OSRAM) |
| WO (1) | WO1994029326A1 (OSRAM) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5453523A (en) * | 1993-06-16 | 1995-09-26 | Emulsion Technology, Inc. | Process for obtaining highly purified phosphatidylcholine |
| US6140519A (en) * | 1998-12-07 | 2000-10-31 | Archer-Daniels-Midland Company | Process for producing deoiled phosphatides |
| CA2354705C (en) * | 1998-12-07 | 2009-10-20 | Archer-Daniels-Midland Company | Process for producing deoiled phosphatides |
| US6833149B2 (en) * | 1999-01-14 | 2004-12-21 | Cargill, Incorporated | Method and apparatus for processing vegetable oil miscella, method for conditioning a polymeric microfiltration membrane, membrane, and lecithin product |
| EP1289543A2 (en) | 2000-05-24 | 2003-03-12 | Eli Lilly And Company | Formulations and methods for treating hypercoagulable states |
| DE10251963A1 (de) * | 2002-11-08 | 2004-05-19 | Lts Lohmann Therapie-Systeme Ag | Transmucosale pharmazeutische Darreichungsform |
| US20050170063A1 (en) * | 2004-01-29 | 2005-08-04 | Lalit Chordia | Production of powder and viscous material |
| US20050220949A1 (en) * | 2004-03-31 | 2005-10-06 | Blas Arzubi | Highly bioefficient isoflavone-phospholipid molecular complexes and methods of making and using the same |
| US7297356B2 (en) * | 2004-05-10 | 2007-11-20 | Grain States Soya, Inc. | Method for manufacturing animal feed, method for increasing the rumen bypass capability of an animal feedstuff and animal feed |
| JP4029110B1 (ja) * | 2006-12-26 | 2008-01-09 | タマ生化学株式会社 | 植物ステロールとホスファチジルコリンの組成物及びその製造方法 |
| US11247964B2 (en) | 2009-05-01 | 2022-02-15 | Rrip, Llc | Method of processing phospholipid based lipid materials |
| US20120009136A1 (en) * | 2010-07-09 | 2012-01-12 | The Dial Corporation | Antiperspirant products comprising natural phospholipids and methods for manufacturing the same |
| EP2841117B1 (en) * | 2012-04-27 | 2019-11-27 | Biomet Manufacturing, LLC | Compositions and methods for coating implant surfaces to inhibit surgical infections |
| US20130288951A1 (en) * | 2012-04-27 | 2013-10-31 | Biomet Manufacturing Corp. | Compositions and methods for coating implant surfaces to inhibit surgical infections |
| US10561674B2 (en) | 2012-12-02 | 2020-02-18 | Lipogen Ltd. | Processes for the preparation of phospholipid-enriched dairy products as neutraceuticals for the formulation of functional foods |
| BR112015017744B1 (pt) * | 2013-01-31 | 2020-11-24 | Upfield Europe B.V. | processo para fabricação de uma emulsão água-em-óleo e sistema em fase contínua oleosa comestível |
| AU2014243102B2 (en) * | 2013-03-26 | 2018-04-26 | Lipid Therapeutics Gmbh | Pharmaceutical formulation comprising phosphatidylcholine for the treatment of ulcerative colitis |
| US9353137B2 (en) * | 2014-02-07 | 2016-05-31 | Ghassem Amoabediny | Method for separation and purification of phosphatidylcholine employing magnetic nanoparticles and compositions so produced |
| CN106456617A (zh) * | 2014-05-19 | 2017-02-22 | 医药公司 | 氯维地平纳米颗粒及其药物组合物 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2718797C3 (de) * | 1977-04-27 | 1987-06-19 | A. Nattermann & Cie GmbH, 5000 Köln | Verfahren zur Gewinnung fließfähiger ölhaltiger gereinigter Phosphatidylcholin |
| DE3227001C1 (de) * | 1982-07-20 | 1983-07-07 | A. Nattermann & Cie GmbH, 5000 Köln | Verfahren zur Gewinnung von mit Phosphatidylcholin hochangereicherten ethanolischen Phosphatidfraktionen |
| US5008037A (en) * | 1988-04-04 | 1991-04-16 | Emulsion Technology, Inc. | Emulsifier for water-in-oil emulsions |
| US5453523A (en) * | 1993-06-16 | 1995-09-26 | Emulsion Technology, Inc. | Process for obtaining highly purified phosphatidylcholine |
-
1993
- 1993-06-16 US US08/077,684 patent/US5453523A/en not_active Expired - Lifetime
-
1994
- 1994-06-16 AU AU71106/94A patent/AU7110694A/en not_active Abandoned
- 1994-06-16 JP JP7502213A patent/JPH08511547A/ja active Pending
- 1994-06-16 CA CA002164124A patent/CA2164124A1/en not_active Abandoned
- 1994-06-16 WO PCT/US1994/006819 patent/WO1994029326A1/en not_active Ceased
- 1994-06-16 DE DE69426114T patent/DE69426114T2/de not_active Expired - Fee Related
- 1994-06-16 EP EP94920238A patent/EP0703918B1/en not_active Expired - Lifetime
-
1995
- 1995-06-05 US US08/463,238 patent/US5703255A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0703918A4 (OSRAM) | 1996-04-24 |
| DE69426114D1 (de) | 2000-11-16 |
| JPH08511547A (ja) | 1996-12-03 |
| WO1994029326A1 (en) | 1994-12-22 |
| US5453523A (en) | 1995-09-26 |
| EP0703918B1 (en) | 2000-10-11 |
| DE69426114T2 (de) | 2001-05-10 |
| US5703255A (en) | 1997-12-30 |
| AU7110694A (en) | 1995-01-03 |
| EP0703918A1 (en) | 1996-04-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |