The Agent Contains Organic Compound Containing Phosphorus (e.g., Lecithin) Patents (Class 516/56)
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Patent number: 11406722Abstract: Stable perfluorocarbon nanodroplet compositions with properties such as low-boiling points and small particle diameters are provided for improved performance in ultrasound imaging and therapeutic applications. Methods of producing stabilized nanodroplet compositions and methods of using the compositions are further provided to allow for improved performance in ultrasound imaging techniques and/or therapeutic applications.Type: GrantFiled: March 16, 2018Date of Patent: August 9, 2022Assignee: The Board of Regents of The University of Texas SystemInventors: Caroline de Gracia Lux, Jacques Lux, Alexander M. Vezeridis, Robert F. Mattrey
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Patent number: 10980745Abstract: Provided are oil-in-water microemulsions for formulating pharmaceutically active compounds. The microemulsions contain oils, surfactants, water, and the pharmaceutical compounds, and are produced by mixing an aqueous phase and a lipid phase in which each phase contains at least one surfactant in a defined ratio whereby the resulting microemulsion has very small dispersed particles, and, is thermodynamically very stable.Type: GrantFiled: October 1, 2019Date of Patent: April 20, 2021Assignees: SIFI S.p.A., Consiglio Nazionale delle RicercheInventors: Elena Solfato, Ilenia Abbate, Cristina Maria Concetta Zappulla, Manuela Santonocito, Santa Viola, Sandro De Falco, Francesco Giuliano
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Patent number: 9522377Abstract: The present invention provides a method for forming a dispersion comprising non-lamellar amphiphile particles having improved phase behavior, particle size distribution and/or storage stability, said method comprising forming a dispersion of lamellar and optionally non-lamellar particles comprising at least one structuring agent in a polar solvent, heating said particles to an elevated temperature, followed by cooling, wherein said heating is to a temperature and for a period sufficient to provide, after cooling, a measurable improvement in phase behavior, particle size distribution and/or storage stability.Type: GrantFiled: August 4, 2004Date of Patent: December 20, 2016Assignee: CAMURUS ABInventors: Gert Wörle, Fredrik Tiberg, Markus Johnsson, Heike Bunjes, Britta Siekmann, Justas Barauskas
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Patent number: 9486408Abstract: The embodiment described herein are related nanoemulsions comprising botulinum toxins. In one embodiment, the nanoemulsions are prepared by high pressure microfluidization and comprise a particle size distribution exclusively between 10 and 300 nm. The nanoemulsions contemplated by the present invention are useful for the cosmetic and medical treatment of muscular contracture states. For example, botulinum toxin may relax facial muscles such that skin wrinkles become smoother and less noticeable. Further, the present invention contemplates a cosmetic formulation that may be self-administered, for example, in the privacy of one's home and without medical supervision.Type: GrantFiled: October 9, 2012Date of Patent: November 8, 2016Assignee: University of Massachusetts LowellInventors: Jonathan Edelson, Robert Nicolosi
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Patent number: 9352291Abstract: A method for dispersing oil spilled into the aqueous environment comprising the treatment of the spilled oil with an oil dispersant composition comprising a phospholipid and a polysaccharide derivative is disclosed.Type: GrantFiled: February 10, 2012Date of Patent: May 31, 2016Assignee: The University of Southern MississippiInventors: Robert Y. Lochhead, Sarah Elizabeth Morgan, Samy Madbouly, Yan Zong
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Patent number: 8557861Abstract: The present invention provides injectable oil-in-water emulsions of taxoid drugs or other water insoluble drugs. The present invention also provides methods for preparing and using such oil-in-water emulsions.Type: GrantFiled: September 28, 2004Date of Patent: October 15, 2013Assignee: Mast Therapeutics, Inc.Inventor: Andrew Xian Chen
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Publication number: 20130075337Abstract: A method for dispersing oil spilled into the aqueous environment comprising the treatment of the spilled oil with an oil dispersant composition comprising a phospholipid and a polysaccharide derivative is disclosed.Type: ApplicationFiled: February 10, 2012Publication date: March 28, 2013Applicant: THE UNIVERSITY OF SOUTHERN MISSISSIPPIInventors: Robert Y. Lochhead, Sarah E. Morgan, Samy Madbouly, Yan Zong
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Patent number: 8361215Abstract: Disclosed is an emulsifier comprising, as an active ingredient, a polyfluoroalkylphosphonic acid salt represented by the general formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cP(O)(OM1)(OM2), wherein M? is a hydrogen atom, an alkali metal, an ammonium base, or an organic amine base, M2 is an alkali metal, an ammonium base, or an organic amine base, n is an integer of 1 to 6, a is an integer of 1 to 4, b is an integer of 1 to 3, and c is an integer of 1 to 3. An aqueous solution or organic solvent solution of the emulsifier can be effectively used to emulsify a perfluoropolyether oil or a perfluorocarbon compound. The resulting emulsion exhibits excellent emulsification stability, and thus can be effectively used as a mold-releasing agent.Type: GrantFiled: October 7, 2010Date of Patent: January 29, 2013Assignee: Unimatec Co., Ltd.Inventors: Yoshiyama Kaneumi, Seiichiro Murata, Katsuyuki Sato
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Patent number: 8158687Abstract: The present invention concerns an oil-in-water emulsion wherein the oil droplets of a diameter in the range of 5 nm to hundreds of micrometers exhibit a nano-sized structurization with hydrophilic domains with a diameter size in the range of 0.5 to 200 nm and being formed by a lipophilic additive.Type: GrantFiled: May 18, 2005Date of Patent: April 17, 2012Assignee: Nestec S.A.Inventors: Anan Yaghmur, Liliana De Campo, Laurent Sagalowicz, Martin Leser, Otto Glatter, Martin Michel, Heribert Johann Watzke
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Patent number: 8076378Abstract: A dispersant comprising a polyester chain obtainable by polymerising a hydroxy carboxylic acid or lactone thereof such as ?-caprolactone with a cyclic alkylene carbonate such as 5,5-dimethyltrimethylene carbonate. The dispersant may be in the form of a phosphate ester where the polyester chain is reacted with a phosphating agent such as polyphosphoric acid or the polyester chain may be attached to a polyamine or polyimine such as polyethyleneimine.Type: GrantFiled: February 1, 2008Date of Patent: December 13, 2011Assignee: The Lubrizol CorporationInventor: Dean Thetford
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Patent number: 7935733Abstract: A dispersant for a more concentrated carbon nanotube solution, and a composition including the same are provided. The dispersant may have a hydrophobic chain structure with head groups capable of surrounding carbon nanotube particles. The dispersant may adsorbed onto the carbon nanotube particles. The composition may include the dispersant, an aqueous liquid medium and a carbon nanotube. The composition may further include an additive. It may be possible to produce a more concentrated carbon nanotube solution exhibiting an increase in dispersion of the carbon nanotube particles and/or more stability.Type: GrantFiled: June 6, 2006Date of Patent: May 3, 2011Assignee: Samsung Electronics Co., Ltd.Inventors: Seon Mi Yoon, Jeong Hee Lee, Eun Sung Lee, Jae Young Choi
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Patent number: 7776799Abstract: The invention concerns a method for cold rolling metals using an aqueous lubricant comprising: (1) at least a mixture based on at least an acid selected among saturated or unsaturated mono- or poly-carboxylic acids, comprising 5 to 40 carbon atoms; at least an acid phosphate ester of formula (RO)x-P(?O)(OH)x?, wherein: R is a hydrocarbon radical, optionally polyalkoxylated; x and x? being equal to 3; the carboxylic acid and/or the acid phosphate ester being optionally neutralized by an organic or mineral base; and (2) at least a natural or synthetic wax exhibiting a melting point not less than 50° C. and having an average particle size ranging between 0.5 and 10 ?m. The use of said lubricant enables to increase the productivity of the method by at least 15% relative to a method using a conventional lubricant.Type: GrantFiled: October 3, 2007Date of Patent: August 17, 2010Assignee: Rhodia ChimieInventors: Dominique Raison, Jean-Guy Le Helloco
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Patent number: 7589144Abstract: The invention concerns granules obtainable by drying an inverse emulsion, dispersed in an external aqueous phase: a) the inverse emulsion comprising an internal aqueous phase, including a hydrophilic active material, dispersed in an internal organic phase, said inverse emulsion including at least a non-ionic surfactant and/or at least an amphiphilic block polymer, and/or at least a cationic surfactant; b) the external aqueous phase including: at least a polyalkylated non-ionic surfactant and/or at least a polalkylated amphiphilic non-ionic polymer; at least a water soluble or water dispersible polymer in solid form in the presence of a water content of not more than 10 wt. % relative to the weight of said polymer and whereof the glass transition temperature is higher than 25° C., preferably higher than 50° C. The granules, once dispersed, enable to obtain a multiple emulsion.Type: GrantFiled: July 20, 2006Date of Patent: September 15, 2009Assignee: Rhodia ChimieInventors: Hélène Lannibois-Drean, Mikel Morvan, Laurent Taisne
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Publication number: 20090163606Abstract: Suspensions having additives for controlled dispersion including a solvent, an ion source, a particle source selected from a partially dissolving colloid or a non-dissolving colloid, and an additive where the additive is added to the solvent prior to the ion source and the particle source when the particle source is the partially dissolving colloid.Type: ApplicationFiled: December 20, 2007Publication date: June 25, 2009Inventors: GLEN HAROLD KIRBY, Brett Allen Boutwell
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Publication number: 20080070992Abstract: The present invention provides a method for preparing a solubilized composition containing an oil-soluble substance having both acid and heat resistance, including: the step of dissolving an oil-soluble substance and two or three emulsifiers selected from (1) an emulsifier E1 comprising an ester of a fatty acid having an HLB of not less than 10 and not more than 14 carbon atoms with a polyglycerol having a polymerization degree of not less than 3, (2) an emulsifier E2 comprising an ester of a fatty acid having an HLB of not less than 10 and not more than 14 carbon atoms with sucrose, or (3) an emulsifier E3 comprising lecithin in which phosphatidylcholine accounts for not less than 50% and/or lysolecithin in which lysophosphatidylcholine accounts for not less than 50% of a phospholipid content in (a) ethanol or (b) a mixed solvent of ethanol with at least one selected from the group consisting of acetone, hexane, and ethyl acetate to prepare a transparent solution; and the step of distilling the solvent off fType: ApplicationFiled: September 18, 2007Publication date: March 20, 2008Inventors: Akihito Hayashi, Chie Kato, Namiko Takahashi, Nobutoshi Hamaguchi, Hen-Sik Koh
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Patent number: 6828352Abstract: The present invention relates to synthetic, novel, preferably fatty phosphoric acid esters which, when neutralized with a neutralizing agent, is revealed as a new surface active agent. Formulations are presented which demonstrate a method for using the disclosed surface active agent to prepare stable oil-in-water, water-in-oil emulsions and various solutions of varying polarity and viscosity for use in a variety of dermatological applications, and/or wherever emulsions or solutions according to the present invention may be used.Type: GrantFiled: January 28, 2003Date of Patent: December 7, 2004Assignee: Walter Merton Company, Inc.Inventor: Arnold W. Fogel
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Patent number: 6806238Abstract: The invention concerns the use as extreme pressure additive in aqueous lubricants used for deforming or transforming metals, lamellar crystallites having a length (L) ranging between 0.1 and 100 &mgr;m, a width (I) ranging between 0.Type: GrantFiled: July 24, 2002Date of Patent: October 19, 2004Assignee: Rhodia ChimieInventors: Gilles Lorentz, Jean-Marie Georgees
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Publication number: 20040167232Abstract: Nanoemulsions having a droplet diameter of less than 3 &mgr;m and which exhibit good temperature stability are comprised of: (a) water; (b) a mineral oil, a Guerbet alcohol or a combination thereof; (c) an alkyl and/or alkenyl oligoglycoside; (d) an alkyl ether phosphate.Type: ApplicationFiled: December 4, 2003Publication date: August 26, 2004Inventors: Joaquin Bigorra Llosas, Rafael Pi Subirana, Marta Torres Fernandez, Gabriela Caldero
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Patent number: 6780824Abstract: Emulsifier system containing a) ethoxylates/propoxylates of fatty alcohols with 8 to 18 C atoms in the alcohol with 2 to 6 ethylene oxide units and 4 to 8 propylene oxide units, b) fatty alcohols and/or fatty alcohol propoxylates with 12 to 24 C atoms in the alcohol and 0 to 3 propylene oxide units and/or distillation residue of these fatty alcohols and c) phosphates, selected from: c1) mono- and/or diesters of phosphoric acid with alkanols with 10-20 C atoms, c2) mono- and/or diesters of phosphoric acid with ethoxylated and/or propoxylated alkanols with 10-20 C atoms and/or c3) phosphates of polyethylene glycol ethers and/or polypropylene glycol ethers, and the water-soluble salts of each of these, in a weight ratio a:b:c=1:0.3:0.1 to 1:4:1; anti-corrosive and emulsifier system with these components, emulsion concentrate with these components, oil-in-water emulsion obtainable therefrom and use thereof as a cleaning, anti-corrosive and low-temperature lubricant emulsion.Type: GrantFiled: October 31, 2002Date of Patent: August 24, 2004Assignee: Henkel Kommanditgesellschaft auf Aktien (Henkel KGaA)Inventors: Hans-Peter Oelscher, Juergen Geke
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Publication number: 20030149118Abstract: The invention is directed to a method and composition which inhibits the oxidation of omega-3 and omega-6 polyunsaturated lipids in an aqueous emulsion. This invention is especially directed to a method and composition which inhibits the oxidation of long chain omega-3 polyunsaturated lipids in an aqueous emulsion. When soy protein, and in particular, soy protein isolates, are blended with omega-3 and/or omega-6 polyunsaturated lipids, the rate of oxidation of the omega-3 and/or omega-6 lipids is reduced and the shelf life of such lipids is extended.Type: ApplicationFiled: February 28, 2003Publication date: August 7, 2003Applicant: Kraft Foods Holdings, Inc.Inventors: Ahmad Akashe, Steven E. Hill
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Patent number: 6593376Abstract: A process for preparing amphiphilic compounds having at least two hydrophilic and at least two hydrophobic groups by reacting an olefinic substrate having at least two double bonds with an organic hydroperoxide to form an oxirane ring, opening, the oxirane ring with an alcohol in the presence of a catalyst system comprising a molybdenum compound as a first catalyst component and a second catalyst component selected from the group consisting of boron trifluoride, alumina, 1,8-diazzabicyclo-(5.4.0)-undec-7-ene, 1,4-diazabicyclo-(2,2,2)-octane.Type: GrantFiled: December 30, 1999Date of Patent: July 15, 2003Assignee: SASOL Germany GmbHInventors: Mark Rüsch gen. Klaas, Klaus Kwetkat, Siegfried Warwel
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Patent number: 6566408Abstract: Aqueous surfactant compositions of alkyl phosphate ester salts having a molar ratio of mono- to di-alkyl phosphate esters equal to or greater than 80:20, and amphoteric surfactants essentially free of tetra-alkyl ammonium moieties. The aqueous surfactant compositions have very low dermal irritation properties.Type: GrantFiled: August 1, 2000Date of Patent: May 20, 2003Assignee: Rhodia, Inc.Inventors: Phillip Loraine Cotrell, Alvino Gabbianelli, Robert Lee Reierson
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Patent number: 6562875Abstract: An aqueous emulsion containing from about 0.1 to about 70 weight percent of a mixture of a) one or more alkoxylated alcohols of formula RO(C2H4O)x(C3H6O)yZ wherein R is straight or branched C4-C40 alkyl; x is 0 to about 25; y is less than 1 to about 50 and Z is H or the residue of an organic acid, and b) an effective emulsifying amount of one or more anionic surfactants and use of the emulsion to inhibit foaming in papermaking processes.Type: GrantFiled: August 30, 2001Date of Patent: May 13, 2003Assignee: Ondeo Nalco CompanyInventors: Gilles Corbel, James J. Svarz, Alan Smith
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Patent number: 6559183Abstract: The present invention relates to a composition comprising a nano-emulsion that contains 5-aminolevulinic acid as well as a carrier in an aqueous phase. This invention also relates to a pharmaceutical preparation containing this composition. The nano-emulsions of this type can be used in photodynamic therapy as well as in the photodiagnostic detection of proliferatives cells.Type: GrantFiled: July 26, 2001Date of Patent: May 6, 2003Assignee: ASAT AG Applied Science & TechnologyInventors: Hans W. Schmid, Gerd Burmeister
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Patent number: 6548557Abstract: The present invention relates to synthetic, novel, preferably fatty phosphoric acid esters which, when neutralized with a neutralizing agent, is revealed as a new surface active agent. Formulations are presented which demonstrate a method for using the disclosed surface active agent to prepare stable oil-in-water, water-in-oil emulsions and various solutions of varying polarity and viscosity for use in a variety of dermatological applications, and/or wherever emulsions or solutions according to the present invention may be used.Type: GrantFiled: November 6, 2000Date of Patent: April 15, 2003Assignee: Walter Merton Co., Inc.Inventor: Arnold W. Fogel
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Patent number: 6541016Abstract: This invention relates to monoalkyl phosphoric esters, dialkyl phosphoric esters, and, in small amounts, trialkyl phosphoric esters or salts thereof, which are preferably based on &bgr;-branched fatty alcohols, particularly Guerbet alcohol, which are effective in lowering the surface tension of both polar and also nonpolar liquids, and which have high stability, even at elevated temperatures, and low sensitivity to electrolytes and acids. The invention further relates to the use of such mixtures as emulsifiers in cosmetic and pharmaceutical formulations, and to the resulting products.Type: GrantFiled: February 26, 1998Date of Patent: April 1, 2003Assignee: Clariant GmbHInventors: Angelika Turowski-Wanke, Matthias Löffler, Oliver Eyrisch, Werner Skrypzak
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Patent number: 6528545Abstract: Fluorocarbon emulsions comprising a stabilizing, particle size controlling fluorophilic/hydrophilic compound which can have the formula RF1—W—RH1 (I) wherein RF1 is a linear, branched or cyclic C2-14 fluorocarbon group; RH1 is a linear, branched or cyclic C2-18 saturated or unsaturated hydrocarbon group; and W is absent or is a bivalent species chosen from the group consisting of —O—, —S—, or various fluorinated structures. Use of the fluorophilic/lipophilic compound in the dispersions of the invention provides stable particle size and efficient emulsification. The dispersions of the invention can comprise biologically useful additive and can be used for various purposes, as oxygen carriers, contrast agents, or diagnostic agents.Type: GrantFiled: June 2, 2000Date of Patent: March 4, 2003Inventors: Jean G. Riess, Michele Postel, Luis Sole-Violan, Marie-Pierre Krafft, Chantal Cornelus
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Patent number: 6448297Abstract: The invention relates to alkyl phosphates, in particular their mixtures, of the formula in which R is C12-C22-alkyl, preferably C14-C18-alkyl, X is a group of the formulae NH3R1, NH2R2R3 or NHR4R5R6, Y is as defined for R or is as defined for X, and R1 is C8-C22-alkyl, R2 and R3 are C1-C22-alkyl or cyclohexyl, and R4, R5 and R6 are C1-C4-alkyl. These compounds, in particular the mixtures of mono- and diesters, are suitable as emulsifiers in the preparation of aqueous emulsions.Type: GrantFiled: June 1, 2000Date of Patent: September 10, 2002Assignee: Clariant GmbHInventors: Angelika Turowski-Wanke, Matthias Löffler
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Patent number: 6432885Abstract: This invention relates to a well treatment fluid and a method to treat an/or fracture a subterranean formation comprising: injecting a well treatment fluid into the formation at sufficient pressure to fracture the formation wherein the fluid comprises: (a) one or more amphoteric surfactants; (b) water; and (c) one or more nonaqueous solvents; (d) optionally, an acid forming compound, and (e) provided that if the acid forming compound is present a hydrophilic alcohol may also be optionally present.Type: GrantFiled: August 26, 1999Date of Patent: August 13, 2002Assignee: Osca, Inc.Inventor: Daniel Patrick Vollmer
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Publication number: 20020090377Abstract: New emulsion and micelle formulations are described as are complexes of these formulations with biologically active substances. The novel formulations are different from cationic lipid vectors such as cationic liposomes in that the complexes formed between biologically active substances and the emulsion and micellar formulations of this invention are physically stable and their transfection activity is resistant to the presence of serum. These novel formulations are disclosed to be useful in areas such as gene therapy or vaccine delivery.Type: ApplicationFiled: January 2, 2002Publication date: July 11, 2002Inventors: Dexi Liu, Feng Liu, Jing-Ping Yang, Leaf Huang
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Patent number: 6417238Abstract: The present invention relates to synthetic, fatty phosphoric acid esters which, when neutralized with a neutralizing agent, is revealed as a new surface active agent, having emollient characteristics. Formulations are presented which demonstrate a method for using the disclosed surface active agent to prepare stable oil-in-water and water-in-oil emulsions of varying polarity and viscosity for use in a variety of dermatological applications, and/or wherever emulsions according to the present invention may be used.Type: GrantFiled: February 24, 2000Date of Patent: July 9, 2002Inventor: Arnold W. Fogel
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Publication number: 20010023262Abstract: An injectable physiologically acceptable aqueous phase fluorocarbon emulsion, which has substantially no free fluorocarbon, has an excellent stability is prepared by a process of the invention. Typically, more than about 99.8 wt. % of the fluorocarbon remains in the size range of about 0.2 to 0.4 microns even after being stored at room temperature for one year or more in sealed containers under a non-oxidizing atmosphere. The emulsion is useful in medical applications, for example, coronary angioplasty, cancer therapy, among others.Type: ApplicationFiled: January 21, 1999Publication date: September 20, 2001Inventors: STUART RAYNOLDS, ROBERT H. DETTRE
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Patent number: 6288130Abstract: The invention relates to oil-free glycerophospholipid formulations which contain a homogeneous mixture of glycerophospholipids and an anhydrous, liquid polyol compound such as glycerol in a molar ratio of 1:0.1 to 1. These formulations are produced, eg, by extracting a starting material consisting of an oil-containing glycerophospholipid (mixture) and the polyol component with a compressed hydrocarbon (mixture) in a rectifying column. The oil-free formulation can be obtained from the melt at the bottom of the column in the form of free-flowing powder, which is ideally suited for stabilising oil-in-water emulsions.Type: GrantFiled: September 20, 1999Date of Patent: September 11, 2001Assignee: SKW Trostberg AktiengesellschaftInventors: Jürgen Heidlas, Karl-Heinz Zirzow, Johann Wiesmüller, Martin Ober, Franz Michlbauer, Jürgen Graefe
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Patent number: 6262130Abstract: Stable, pumpable aqueous surfactant compositions of water and alkyl phosphate ester salts having a molar ratio of mono- to di- alkyl phosphate esters equal to or greater than 80:20, with the surfactant composition being essentially free of water-soluble alcohol or co-solvent. The pumpable aqueous surfactant compositions have a solids content of about 40% by weight or more and exhibit one or more pumpable regions over a range of pH values for the aqueous surfactant composition.Type: GrantFiled: November 23, 1999Date of Patent: July 17, 2001Assignee: Rhodia, Inc.Inventors: Paul-Joel Derian, Tao Gao, Pascal Jean-Claude Herve, Robert Lee Reierson
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Patent number: 6126946Abstract: A heat and shelf-stable oil-in-water emulsion useful as a tissue or cell-selective delivery vehicle. Radioactive or stable, synthetic or semi-synthetic polyhalogenated triglycerides, such as 2-oleoylglycerol-1,3-bis[7-(3-amino-2,4,6-triiodophenyl)heptanoate] or 2-oleoylglycerol-1,3-bis[.omega.-(3,5-bis-trifluoromethyl)hepatanoate] or phenyl acetate, can be incorporated into the lipophilic core of a lipoprotein-like emulsion particle. The lipophilic core is surrounded by a phospholipid membrane comprising cholesterol and apolipoproteins. For hepatocyte-selective delivery, the emulsion is chylomicron remnant-like by being in a size range of 50 to 200 nm as measured by number weighting analysis with a narrow size distribution (<2% greater than 300 nm) and having a composition simulating naturally-occurring chylomicron remnants. Use of cholesterol in the emulsion formula facilitates association of apolipoproteins, especially Apo E which are recognized by liver cells and necessary for binding and uptake.Type: GrantFiled: July 23, 1997Date of Patent: October 3, 2000Assignee: University of Michigan, The Board of RegentsInventors: Raymond E. Counsell, Marc A. Longino, Jamey P. Weichert, Douglas A. Bakan
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Patent number: 6113919Abstract: Fluorocarbon emulsions comprising a stabilizing, particle size controlling fluorophilic/hydrophilic compound which can have the formulaR.sub.F.sup.1 --W--R.sub.H.sup.1 (I)whereinR.sub.F.sup.1 is a linear, branched or cyclic C.sub.2-14 fluorocarbon group;R.sub.H.sup.1 is a linear, branched or cyclic C.sub.2-18 saturated or unsaturated hydrocarbon group; andW is absent or is a bivalent species chosen from the group consisting of --O--, --S--, or various fluorinated structures. Use of the fluorophilic/lipophilic compound in the dispersions of the invention provides stable particle size and efficient emulsification. The dispersions of the invention can comprise biologically useful additive and can be used for various purposes, as oxygen carriers, contrast agents, or diagnostic agents.Type: GrantFiled: June 7, 1995Date of Patent: September 5, 2000Assignee: Alliance Pharmaceutical Corp.Inventors: Jean G. Reiss, Michele Postel, Luis Sole-Violan, Marie-Pierre Krafft, Chantal Cornelus
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Patent number: 6103216Abstract: A heat and shelf-stable oil-in-water emulsion useful as a tissue or cell-selective delivery vehicle. Radioactive or stable, synthetic or semi-synthetic polyhalogenated triglycerides, such as 2-oleoylglycerol-1,3-bis[7-(3-amino-2,4,6-triiodophenyl)heptanoate] or 2-oleoylglycerol-1,3-bis[.omega.-(3,5-bis-trifluoromethyl)-heptanoate] or phenyl acetate, can be incorporated into the lipophilic core of a lipoprotein-like emulsion particle. The lipophilic core is surrounded by a phospholipid membrane comprising cholesterol and apolipoproteins. For hepatocyte-selective delivery, the emulsion is chylomicron remnant-like by being in a size range of 50 to 200 nm as measured by number weighting analysis with a narrow size distribution (<2% greater than 300 nm) and having a composition simulating naturally-occurring chylomicron remnants. Use of cholesterol in the emulsion formula facilitates association of apolipoproteins, especially Apo E which are recognized by liver cells and necessary for binding and uptake.Type: GrantFiled: November 15, 1996Date of Patent: August 15, 2000Assignee: The Board of Regents acting for and on behalf of the University of MichiganInventors: Raymond E. Counsell, Marc A. Longino, Jamey P. Weichert, Douglas A. Bakan
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Patent number: 6066753Abstract: The invention relates to mixtures of long-chain alkyl phosphates of the formula ##STR1## in which R is a mixture of C.sub.12 -C.sub.22, preferably C.sub.14 -C.sub.20, straight-chain alkyl radicals and C.sub.12 -C.sub.22, preferably C.sub.14 -C.sub.20, .beta.-branched alkyl radicals, and X and Y are identical or different and are hydrogen, alkali metal or an equivalent of an alkaline earth metal, ammonium, mono-, di- or tri-alkylammonium or an organic base, or X and/or Y are as defined under R. These esters are suitable as emulsifiers, in particular for oil-in-water emulsions of a cosmetic pharmaceutical nature.Type: GrantFiled: September 11, 1998Date of Patent: May 23, 2000Assignee: Clariant GmbHInventors: Angelika Turowski-Wanke, Matthias Loffler, Oliver Eyrisch
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Patent number: 6054494Abstract: The present invention relates to a phospholipid composition comprising two or more phospholipids, the electric conductivity and pH of a 5 wt. % suspension of the phospholipid composition in deionized water being in the range of 130 to 220 .mu.S/cm and in the range of 6.5 to 9.5, respectively; a process for producing the same; and the use of the same.Type: GrantFiled: July 13, 1998Date of Patent: April 25, 2000Assignee: Q. P. CorporationInventors: Hitoshi Narabe, Kiyoko Tanabe, Yasuhiko Shigematsu, Noriyuki Ishikawa, Mari Yamada, Hideaki Kobayashi
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Patent number: 6007826Abstract: An oil-in-water emulsion useful as a delivery vehicle of hydrophobic ingredients such as pharmaceutical drugs and cosmetic active agent; wherein the emulsion particles have a net positive charge (i.e. a positive zeta potential).Type: GrantFiled: October 15, 1996Date of Patent: December 28, 1999Assignee: Yisum Research Development Company of the Hebrew University of JerusalemInventors: Simon Benita, Efrat Elbaz
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Patent number: 5984519Abstract: In a fine particle producing device, particles of a substance contained in a fluid are caused to collide with each other under extremely high pressure, whereby the particles are emulsified, dispersed or reduced to finer particles in the fluid in an instant. One of the blocks mounted in a cylindrical sealed casing has a pair of curved channel portions for guiding converging high-speed fluid streams and a turbulence pocket formed at a position where the curved channel portions are joined for temporarily holding fluid turbulence caused by collision of the high-speed fluid streams.Type: GrantFiled: December 22, 1997Date of Patent: November 16, 1999Assignees: Genus Corporation, Hakusui Tech Co., Ltd.Inventors: Tadao Onodera, Chikara Kannari, Akikazu Koyano, Yoshihiro Furukawa, Kazutoshi Mitake, Fumio Yasuda, Fuminori Miyake, Fusamitsu Fujishima
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Patent number: 5985941Abstract: A heat and shelf-stable oil-in-water emulsion useful as a tissue or cell-selective delivery vehicle. Radioactive or stable, synthetic or semi-synthetic polyhalogenated triglycerides, such as 2-oleoylglycerol-1,3-bis[7-(3-amino-2,4,6-triiodophenyl)heptanoate] or 2-oleoylglycerol-1,3-bis[.omega.-(3,5-bis-trifluoromethyl)hepatanoate] or phenyl acetate, can be incorporated into the lipophilic core of a lipoprotein-like emulsion particle. The lipophilic core is surrounded by a phospholipid membrane comprising cholesterol and apolipoproteins. For hepatocyte-selective delivery, the emulsion is chylomicron remnant-like by being in a size range of 50 to 200 nm as measured by number weighting analysis with a narrow size distribution (<2% greater than 300 nm) and having a composition simulating naturally-occurring chylomicron remnants. Use of cholesterol in the emulsion formula facilitates association of apolipoproteins, especially Apo E which are recognized by liver cells and necessary for binding and uptake.Type: GrantFiled: June 30, 1995Date of Patent: November 16, 1999Assignee: University of MichiganInventors: Raymond E. Counsell, Marc A. Longino, Jamey P. Weichert, Douglas A. Bakan
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Patent number: RE38459Abstract: An injectable physiologically acceptable aqueous phase fluorocarbon emulsion, which has substantially no free fluorocarbon, has an excellent stability is prepared by a process of the invention. Typically, more than about 99.8 wt. % of the fluorocarbon remains in the size range of about 0.2 to 0.4 microns even after being stored at room temperature for one year or more in sealed containers under a non-oxidizing atmosphere. The emulsion is useful in medical applications, for example, coronary angioplasty, cancer therapy, among others.Type: GrantFiled: January 21, 1999Date of Patent: March 9, 2004Assignee: Thomas Jefferson UniversityInventors: Stuart Raynolds, Robert H. Dettre