DD261363A5 - Neue polyhydroxylierte und hochfluorierte verbindungen, deren herstellung und verwendung als oberflaechenaktive stoffe - Google Patents
Neue polyhydroxylierte und hochfluorierte verbindungen, deren herstellung und verwendung als oberflaechenaktive stoffe Download PDFInfo
- Publication number
- DD261363A5 DD261363A5 DD87305442A DD30544287A DD261363A5 DD 261363 A5 DD261363 A5 DD 261363A5 DD 87305442 A DD87305442 A DD 87305442A DD 30544287 A DD30544287 A DD 30544287A DD 261363 A5 DD261363 A5 DD 261363A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- octyl
- propanoyl
- hexyl
- ethyl
- group
- Prior art date
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
- A61K9/0026—Blood substitute; Oxygen transporting formulations; Plasma extender
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/08—Plasma substitutes; Perfusion solutions; Dialytics or haemodialytics; Drugs for electrolytic or acid-base disorders, e.g. hypovolemic shock
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
- C07C43/1787—Unsaturated ethers containing hydroxy or O-metal groups containing six-membered aromatic rings and having unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
- C07D307/20—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- C07H15/10—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical containing unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/007—Organic compounds containing halogen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/56—Glucosides; Mucilage; Saponins
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/004—Surface-active compounds containing F
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8611084A FR2602774B1 (fr) | 1986-07-29 | 1986-07-29 | Nouvelles molecules amphiphiles polyhydroxylees et perfluoroalkylees ayant des proprietes tensioactives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD261363A5 true DD261363A5 (de) | 1988-10-26 |
Family
ID=9337904
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD87305442A DD261363A5 (de) | 1986-07-29 | 1987-07-28 | Neue polyhydroxylierte und hochfluorierte verbindungen, deren herstellung und verwendung als oberflaechenaktive stoffe |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4985550A (ja) |
| EP (1) | EP0255443B1 (ja) |
| JP (1) | JPH0816106B2 (ja) |
| CN (1) | CN87105263A (ja) |
| AT (1) | ATE81507T1 (ja) |
| AU (1) | AU608761B2 (ja) |
| CA (1) | CA1315778C (ja) |
| DD (1) | DD261363A5 (ja) |
| DE (1) | DE3782210T2 (ja) |
| DK (1) | DK392687A (ja) |
| ES (1) | ES2052594T3 (ja) |
| FR (1) | FR2602774B1 (ja) |
| GR (1) | GR3006524T3 (ja) |
| IE (1) | IE61102B1 (ja) |
| NO (1) | NO169542C (ja) |
| NZ (1) | NZ221232A (ja) |
| PT (1) | PT85425B (ja) |
Families Citing this family (81)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1223324B (it) * | 1987-10-28 | 1990-09-19 | Ausimont Spa | Microemulsioni acquose comprendenti perfluoropolieteri funzionali |
| US5055562A (en) * | 1988-02-01 | 1991-10-08 | Biomira, Inc. | Fluorocarbon chain-containing antigenic conjugates |
| CA1326665C (en) * | 1988-02-27 | 1994-02-01 | Ryohei Yamaoka | Fluorine-containing glycoside and its use |
| EP0375610A3 (en) * | 1988-12-19 | 1992-01-02 | Ciba-Geigy Ag | Perfluoroalkylthioglycosides |
| US20020150539A1 (en) * | 1989-12-22 | 2002-10-17 | Unger Evan C. | Ultrasound imaging and treatment |
| US5580575A (en) * | 1989-12-22 | 1996-12-03 | Imarx Pharmaceutical Corp. | Therapeutic drug delivery systems |
| US5656211A (en) * | 1989-12-22 | 1997-08-12 | Imarx Pharmaceutical Corp. | Apparatus and method for making gas-filled vesicles of optimal size |
| US6551576B1 (en) | 1989-12-22 | 2003-04-22 | Bristol-Myers Squibb Medical Imaging, Inc. | Container with multi-phase composition for use in diagnostic and therapeutic applications |
| US5733572A (en) * | 1989-12-22 | 1998-03-31 | Imarx Pharmaceutical Corp. | Gas and gaseous precursor filled microspheres as topical and subcutaneous delivery vehicles |
| US5585112A (en) * | 1989-12-22 | 1996-12-17 | Imarx Pharmaceutical Corp. | Method of preparing gas and gaseous precursor-filled microspheres |
| US5305757A (en) * | 1989-12-22 | 1994-04-26 | Unger Evan C | Gas filled liposomes and their use as ultrasonic contrast agents |
| US6088613A (en) * | 1989-12-22 | 2000-07-11 | Imarx Pharmaceutical Corp. | Method of magnetic resonance focused surgical and therapeutic ultrasound |
| US6001335A (en) * | 1989-12-22 | 1999-12-14 | Imarx Pharmaceutical Corp. | Contrasting agents for ultrasonic imaging and methods for preparing the same |
| US5922304A (en) * | 1989-12-22 | 1999-07-13 | Imarx Pharmaceutical Corp. | Gaseous precursor filled microspheres as magnetic resonance imaging contrast agents |
| US5542935A (en) | 1989-12-22 | 1996-08-06 | Imarx Pharmaceutical Corp. | Therapeutic delivery systems related applications |
| US6146657A (en) * | 1989-12-22 | 2000-11-14 | Imarx Pharmaceutical Corp. | Gas-filled lipid spheres for use in diagnostic and therapeutic applications |
| US5776429A (en) * | 1989-12-22 | 1998-07-07 | Imarx Pharmaceutical Corp. | Method of preparing gas-filled microspheres using a lyophilized lipids |
| FR2665705B1 (fr) * | 1990-08-09 | 1993-07-30 | Atta | Nouveaux derives fluores amphiphiles a structure telomere, leur procede de preparation et leur utilisation dans des preparations a usage biomedical. |
| US5874062A (en) * | 1991-04-05 | 1999-02-23 | Imarx Pharmaceutical Corp. | Methods of computed tomography using perfluorocarbon gaseous filled microspheres as contrast agents |
| US5205290A (en) | 1991-04-05 | 1993-04-27 | Unger Evan C | Low density microspheres and their use as contrast agents for computed tomography |
| FR2677360B1 (fr) * | 1991-06-05 | 1995-04-14 | Atta | Composes amphiphiles perfluoroalkyles du phosphore, leurs preparations et leurs applications notamment dans le domaine biomedical. |
| FR2679150A1 (fr) * | 1991-07-17 | 1993-01-22 | Atta | Preparations comprenant un fluorocarbure ou compose hautement fluore et un compose organique lipophile-fluorophile, et leurs utilisations. |
| MX9205298A (es) | 1991-09-17 | 1993-05-01 | Steven Carl Quay | Medios gaseosos de contraste de ultrasonido y metodo para seleccionar gases para usarse como medios de contraste de ultrasonido |
| US6875420B1 (en) | 1991-09-17 | 2005-04-05 | Amersham Health As | Method of ultrasound imaging |
| US5409688A (en) * | 1991-09-17 | 1995-04-25 | Sonus Pharmaceuticals, Inc. | Gaseous ultrasound contrast media |
| US6723303B1 (en) | 1991-09-17 | 2004-04-20 | Amersham Health, As | Ultrasound contrast agents including protein stabilized microspheres of perfluoropropane, perfluorobutane or perfluoropentane |
| GB9125454D0 (en) * | 1991-11-29 | 1992-01-29 | Isis Innovation | Oxygen transport agents |
| US5621144A (en) * | 1991-11-29 | 1997-04-15 | Isis Innovation Limited | Fluorinated compounds as oxygen transport agents |
| CA2131184A1 (en) * | 1992-04-03 | 1993-10-14 | Jan Willem Hubert Smeets | Selective n-acylation of amino alcohols |
| US5846516A (en) * | 1992-06-03 | 1998-12-08 | Alliance Pharmaceutial Corp. | Perfluoroalkylated amphiphilic phosphorus compounds: preparation and biomedical applications |
| US5350359A (en) * | 1992-07-16 | 1994-09-27 | Temple University Of The Commonwealth System Of Higher Education | Control, treatment and/or diagnosis of physiological conditions with degassed perfluorocarbon liquid |
| FR2694559B1 (fr) * | 1992-08-06 | 1994-10-28 | Atta | Nouveaux dérivés amphiphiles d'aminoacides ou de peptides, leur procédé de préparation et leur utilisation dans des préparations à usage biomédical. |
| IL108416A (en) | 1993-01-25 | 1998-10-30 | Sonus Pharma Inc | Colloids with phase difference as contrast ultrasound agents |
| WO1994016739A1 (en) * | 1993-01-25 | 1994-08-04 | Sonus Pharmaceuticals, Inc. | Phase shift colloids as ultrasound contrast agents |
| US5824781A (en) * | 1993-08-16 | 1998-10-20 | Hsia; Jen-Chang | Compositions and methods utilizing nitroxides in combination with biocompatible macromolecules |
| TW381022B (en) | 1993-08-16 | 2000-02-01 | Hsia Jen Chang | Compositions and methods utilizing nitroxides to avoid oxygen toxicity, particularly in stabilized, polymerized, conjugated, or encapsulated hemoglobin used as a red cell substitute |
| US5725839A (en) * | 1993-08-16 | 1998-03-10 | Hsia; Jen-Chang | Compositions and methods utilizing nitroxides in combination with biocompatible macromolecules for ERI or MRI |
| US5736121A (en) * | 1994-05-23 | 1998-04-07 | Imarx Pharmaceutical Corp. | Stabilized homogenous suspensions as computed tomography contrast agents |
| FR2720943B1 (fr) * | 1994-06-09 | 1996-08-23 | Applic Transferts Technolo | Emulsions inverses stables à forte concentration en composé(s) fluoré(s) et leur utilisation pour l'administration pulmonaire de médicaments et pour la fabrication d'émulsions multiples. |
| US5562893A (en) * | 1994-08-02 | 1996-10-08 | Molecular Biosystems, Inc. | Gas-filled microspheres with fluorine-containing shells |
| US5965109A (en) * | 1994-08-02 | 1999-10-12 | Molecular Biosystems, Inc. | Process for making insoluble gas-filled microspheres containing a liquid hydrophobic barrier |
| US5730955A (en) * | 1994-08-02 | 1998-03-24 | Molecular Biosystems, Inc. | Process for making gas-filled microspheres containing a liquid hydrophobic barrier |
| US6743779B1 (en) | 1994-11-29 | 2004-06-01 | Imarx Pharmaceutical Corp. | Methods for delivering compounds into a cell |
| US5830430A (en) * | 1995-02-21 | 1998-11-03 | Imarx Pharmaceutical Corp. | Cationic lipids and the use thereof |
| US5997898A (en) * | 1995-06-06 | 1999-12-07 | Imarx Pharmaceutical Corp. | Stabilized compositions of fluorinated amphiphiles for methods of therapeutic delivery |
| US5667809A (en) * | 1995-06-07 | 1997-09-16 | Alliance Pharmaceutical Corp. | Continuous fluorochemical microdispersions for the delivery of lipophilic pharmaceutical agents |
| US6139819A (en) * | 1995-06-07 | 2000-10-31 | Imarx Pharmaceutical Corp. | Targeted contrast agents for diagnostic and therapeutic use |
| US6231834B1 (en) | 1995-06-07 | 2001-05-15 | Imarx Pharmaceutical Corp. | Methods for ultrasound imaging involving the use of a contrast agent and multiple images and processing of same |
| US5874481A (en) * | 1995-06-07 | 1999-02-23 | Alliance Pharmaceutical Corp. | Fluorochemical solutions for the delivery of lipophilic pharmaceutical agents |
| US6521211B1 (en) * | 1995-06-07 | 2003-02-18 | Bristol-Myers Squibb Medical Imaging, Inc. | Methods of imaging and treatment with targeted compositions |
| US5611344A (en) * | 1996-03-05 | 1997-03-18 | Acusphere, Inc. | Microencapsulated fluorinated gases for use as imaging agents |
| HU226714B1 (en) * | 1996-03-05 | 2009-07-28 | Acusphere | Microencapsulated fluorinated gases for use as imaging agents |
| DE69736981D1 (de) | 1996-05-01 | 2007-01-04 | Imarx Pharmaceutical Corp | In vitro verfahren zum einbringen von nukleinsäuren in eine zelle |
| FR2750134B1 (fr) * | 1996-06-20 | 1998-08-14 | Ceca Sa | 1-c-perfluoroalkyl glycosides, procede de preparation et utilisations |
| US5837221A (en) * | 1996-07-29 | 1998-11-17 | Acusphere, Inc. | Polymer-lipid microencapsulated gases for use as imaging agents |
| US6414139B1 (en) | 1996-09-03 | 2002-07-02 | Imarx Therapeutics, Inc. | Silicon amphiphilic compounds and the use thereof |
| US5846517A (en) * | 1996-09-11 | 1998-12-08 | Imarx Pharmaceutical Corp. | Methods for diagnostic imaging using a renal contrast agent and a vasodilator |
| ATE231004T1 (de) * | 1996-09-11 | 2003-02-15 | Imarx Pharmaceutical Corp | Verbesserte verfahren zur diagnostischen bilderzeugung unter verwendung eines kontrastmittels und eines vasodilators |
| US5834519A (en) | 1996-10-11 | 1998-11-10 | Wayne State University | Stabilized gas-supersaturated emulsions and suspensions |
| US5907017A (en) * | 1997-01-31 | 1999-05-25 | Cornell Research Foundation, Inc. | Semifluorinated side chain-containing polymers |
| US6090800A (en) * | 1997-05-06 | 2000-07-18 | Imarx Pharmaceutical Corp. | Lipid soluble steroid prodrugs |
| US6120751A (en) | 1997-03-21 | 2000-09-19 | Imarx Pharmaceutical Corp. | Charged lipids and uses for the same |
| US6537246B1 (en) | 1997-06-18 | 2003-03-25 | Imarx Therapeutics, Inc. | Oxygen delivery agents and uses for the same |
| US6143276A (en) * | 1997-03-21 | 2000-11-07 | Imarx Pharmaceutical Corp. | Methods for delivering bioactive agents to regions of elevated temperatures |
| US6416740B1 (en) | 1997-05-13 | 2002-07-09 | Bristol-Myers Squibb Medical Imaging, Inc. | Acoustically active drug delivery systems |
| US5980936A (en) * | 1997-08-07 | 1999-11-09 | Alliance Pharmaceutical Corp. | Multiple emulsions comprising a hydrophobic continuous phase |
| US6548047B1 (en) | 1997-09-15 | 2003-04-15 | Bristol-Myers Squibb Medical Imaging, Inc. | Thermal preactivation of gaseous precursor filled compositions |
| US6123923A (en) * | 1997-12-18 | 2000-09-26 | Imarx Pharmaceutical Corp. | Optoacoustic contrast agents and methods for their use |
| US20010003580A1 (en) | 1998-01-14 | 2001-06-14 | Poh K. Hui | Preparation of a lipid blend and a phospholipid suspension containing the lipid blend |
| DE19948651B4 (de) * | 1999-09-29 | 2006-10-05 | Schering Ag | Para- und diamagnetische perfluorhaltige Verbindungen enthaltende galenische Formulierungen, deren Herstellung und Verwendung |
| GB2364702A (en) * | 2000-07-17 | 2002-02-06 | Unilever Plc | Perfluoroalkyl amphiphilic fabric treatment compounds |
| US7008535B1 (en) * | 2000-08-04 | 2006-03-07 | Wayne State University | Apparatus for oxygenating wastewater |
| ES2279113T3 (es) * | 2002-05-16 | 2007-08-16 | Daikin Industries, Ltd. | Compuestos tensioactivos no ionicos solubles en agua que contienen fluor, su utilizacion y procedimiento para la preparacion de los compuestos. |
| US7025697B2 (en) * | 2003-11-26 | 2006-04-11 | New Archery Products Corp. | Blade steering apparatus |
| US8012457B2 (en) * | 2004-06-04 | 2011-09-06 | Acusphere, Inc. | Ultrasound contrast agent dosage formulation |
| CN100396369C (zh) * | 2006-03-02 | 2008-06-25 | 翟健 | 一种杂化非离子氟表面活性剂及其合成方法 |
| EP2217337B1 (en) * | 2007-10-16 | 2016-07-20 | Tyco Fire Products LP | Fluoroalkenyl poly(1,6)glycosides |
| US20120309853A1 (en) * | 2011-06-06 | 2012-12-06 | E I Du Pont De Nemours And Company | Aldohexose-based fluoroadditives |
| DE102013102239A1 (de) * | 2013-03-06 | 2014-09-11 | Universität Zu Köln | Carbosilanhaltiger Feuerlöschschaum |
| CN105238567B (zh) * | 2015-10-10 | 2017-11-17 | 泉州市福达科技咨询有限公司 | 一种环保型含氟清洗剂及其制备方法 |
| FR3072246B1 (fr) * | 2017-10-13 | 2020-06-12 | Biodesiv Efnium | Polymere antimicrobien pour semences animales |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2891052A (en) * | 1956-04-10 | 1959-06-16 | Rohm & Haas | Anhydrosorbityl amides and process of preparation |
| DE1468176A1 (de) * | 1963-01-08 | 1968-12-12 | Lepetit Spa | Verfahren zur Herstellung von nichtzyklischen Xylit-Estern |
| US3839318A (en) * | 1970-09-27 | 1974-10-01 | Rohm & Haas | Process for preparation of alkyl glucosides and alkyl oligosaccharides |
| IT967894B (it) * | 1971-09-27 | 1974-03-11 | Fmc Corp | Composti anti macchia a base di poliuretani fluorurati e proces so per la loro applicazione a prodotti tessili |
| US3952066A (en) * | 1972-07-07 | 1976-04-20 | Thiokol Corporation | Derivatives of perfluoroalkyl iodide-allyl glycidyl ether adducts |
| US4089804A (en) * | 1976-12-30 | 1978-05-16 | Ciba-Geigy Corporation | Method of improving fluorinated surfactants |
| JPS601175A (ja) * | 1983-06-16 | 1985-01-07 | Daikin Ind Ltd | アスコルビン酸誘導体 |
| JPS604127A (ja) * | 1983-06-21 | 1985-01-10 | Daikin Ind Ltd | 抗菌剤 |
| JPS6028944A (ja) * | 1983-07-25 | 1985-02-14 | Kao Corp | 新規なポリオ−ルエ−テル化合物およびその製造方法ならびにこれを含有する化粧料 |
| JPS61107527A (ja) * | 1984-10-31 | 1986-05-26 | Matsushita Electric Ind Co Ltd | 磁気記録媒体 |
| GB8525871D0 (en) * | 1985-10-21 | 1985-11-27 | Tate & Lyle Plc | Chemical compound |
-
1986
- 1986-07-29 FR FR8611084A patent/FR2602774B1/fr not_active Expired - Fee Related
-
1987
- 1987-07-28 US US07/078,626 patent/US4985550A/en not_active Expired - Lifetime
- 1987-07-28 IE IE204587A patent/IE61102B1/en not_active IP Right Cessation
- 1987-07-28 DD DD87305442A patent/DD261363A5/de not_active IP Right Cessation
- 1987-07-28 PT PT85425A patent/PT85425B/pt not_active IP Right Cessation
- 1987-07-28 NO NO873168A patent/NO169542C/no unknown
- 1987-07-28 NZ NZ221232A patent/NZ221232A/xx unknown
- 1987-07-28 AU AU76194/87A patent/AU608761B2/en not_active Ceased
- 1987-07-28 DK DK392687A patent/DK392687A/da not_active Application Discontinuation
- 1987-07-29 EP EP87401769A patent/EP0255443B1/en not_active Expired - Lifetime
- 1987-07-29 CA CA000543291A patent/CA1315778C/en not_active Expired - Fee Related
- 1987-07-29 AT AT87401769T patent/ATE81507T1/de not_active IP Right Cessation
- 1987-07-29 CN CN198787105263A patent/CN87105263A/zh active Pending
- 1987-07-29 ES ES87401769T patent/ES2052594T3/es not_active Expired - Lifetime
- 1987-07-29 JP JP62191498A patent/JPH0816106B2/ja not_active Expired - Lifetime
- 1987-07-29 DE DE8787401769T patent/DE3782210T2/de not_active Expired - Fee Related
-
1992
- 1992-12-14 GR GR920402898T patent/GR3006524T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE81507T1 (de) | 1992-10-15 |
| GR3006524T3 (ja) | 1993-06-30 |
| DE3782210D1 (de) | 1992-11-19 |
| PT85425B (pt) | 1990-06-29 |
| NO873168L (no) | 1988-02-01 |
| CN87105263A (zh) | 1988-06-15 |
| NO169542C (no) | 1992-07-08 |
| ES2052594T3 (es) | 1994-07-16 |
| JPS6399066A (ja) | 1988-04-30 |
| NO169542B (no) | 1992-03-30 |
| PT85425A (en) | 1987-08-01 |
| DK392687D0 (da) | 1987-07-28 |
| US4985550A (en) | 1991-01-15 |
| FR2602774A1 (fr) | 1988-02-19 |
| DE3782210T2 (de) | 1993-04-22 |
| CA1315778C (en) | 1993-04-06 |
| AU7619487A (en) | 1988-02-04 |
| IE872045L (en) | 1988-01-29 |
| NZ221232A (en) | 1990-08-28 |
| EP0255443B1 (en) | 1992-10-14 |
| NO873168D0 (no) | 1987-07-28 |
| JPH0816106B2 (ja) | 1996-02-21 |
| FR2602774B1 (fr) | 1990-10-19 |
| IE61102B1 (en) | 1994-10-05 |
| AU608761B2 (en) | 1991-04-18 |
| DK392687A (da) | 1988-01-30 |
| EP0255443A1 (en) | 1988-02-03 |
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