DE102012014465A1 - Emulsion, useful in a mixture with known skin care or wound-healing components for improving oxygen supply of human tissue, preferably skin or wound tissue, comprises perfluorocarbon compound and water, and polyelectrolyte - Google Patents

Emulsion, useful in a mixture with known skin care or wound-healing components for improving oxygen supply of human tissue, preferably skin or wound tissue, comprises perfluorocarbon compound and water, and polyelectrolyte Download PDF

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DE102012014465A1
DE102012014465A1 DE201210014465 DE102012014465A DE102012014465A1 DE 102012014465 A1 DE102012014465 A1 DE 102012014465A1 DE 201210014465 DE201210014465 DE 201210014465 DE 102012014465 A DE102012014465 A DE 102012014465A DE 102012014465 A1 DE102012014465 A1 DE 102012014465A1
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emulsion
wound
tissue
polyelectrolyte
skin
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Dr. Risse Gunter
Dr. Haufe Helfried
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Gmbu E V
Gmbu Ev Fachsektion Dresden
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Gmbu Ev Fachsektion Dresden
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/69—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing fluorine
    • A61K8/70—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing fluorine containing perfluoro groups, e.g. perfluoroethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/02—Halogenated hydrocarbons
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Dermatology (AREA)
  • Dispersion Chemistry (AREA)
  • Medicinal Preparation (AREA)

Abstract

Emulsion comprises at least one perfluorocarbon compound and water, and at least one polyelectrolyte.

Description

Die Erfindung betrifft Emulsionen von Perfluorocarbonverbindungen in Wasser. Die Perfluorocarbonemulsionen können zum Beispiel zur Verbesserung der Sauerstoffversorgung der menschlichen Haut und des Gewebes, insbesondere von Wundgewebe Anwendung finden.The invention relates to emulsions of perfluorocarbon compounds in water. For example, the perfluorocarbon emulsions can be used to improve the oxygenation of human skin and tissue, particularly wound tissue.

Perfluorocarbonverbindungen können große Mengen von Sauerstoff und anderen therapeutisch wirksamen Gasen lösen. Sie werden bereits eingesetzt, um Sauerstoff für kosmetische oder medizinisch therapeutische Zwecke in die Haut oder auch Wundgewebe zu übertragen. Um Perfluorocarbonverbindungen in eine topisch anwendbare Form zu bringen, werden diese im Allgemeinen unter Verwendung von Emulgatoren mit relativ großem Aufwand zu wasserhaltigen Emulsionen verarbeitet. Die Bindung der Perfluorocarbonverbindungen in Form von sehr kleinen Tropfen in wässrigen Emulsionen verbessert deren Einsetzbarkeit in lokalen Anwendungen. Außerdem können die emulgierten Perfluorocarbonverbindungen im Gemisch mit weiteren Komponenten eingesetzt werden, welche deren Wirkung unterstützen bzw. ergänzen.Perfluorocarbon compounds can dissolve large quantities of oxygen and other therapeutically active gases. They are already used to transfer oxygen for cosmetic or medical therapeutic purposes in the skin or wound tissue. In order to bring perfluorocarbon compounds into a topically applicable form, they are generally processed using emulsifiers with relatively great effort to aqueous emulsions. The binding of the perfluorocarbon compounds in the form of very small droplets in aqueous emulsions improves their applicability in local applications. In addition, the emulsified perfluorocarbon compounds can be used in admixture with other components which support or supplement their action.

Grundlegende Zusammenhänge zu Eigenschaften und zur Anwendung von Perfluorocarbonemulsionen als Blutersatzstoff werden von Spahn beschrieben ( Donat R Spahn, Blood substitutes Artificial oxygen carriers: perfluorocarbon emulsions, Crit Care. 1999; 3(5): R93–R97. Published online 1999 September 24 ).Fundamental relationships to properties and the use of perfluorocarbon emulsions as a blood substitute are described by Spahn ( Donat R Spahn, Blood substitutes Artificial oxygen carriers: perfluorocarbon emulsions, Crit Care. 1999; 3 (5): R93-R97. Published online 1999 September 24 ).

US-Patent 4859363 beschreibt eine Öl-in-Wasser Emulsion von Perfluorocarbonen, welche durch den Zusatz von Perfluorocarbonverbindungen mit erhöhtem Siedepunkt stabilisiert werden. Eine derartige Emulsion umfasst zum Beispiel Perfluorodecalin, Pluronic F108, Perfluorperhydrophenanthren und destilliertes Wasser. U.S. Patent 4,859,363 describes an oil-in-water emulsion of perfluorocarbons which are stabilized by the addition of perfluorocarbon compounds of elevated boiling point. Such an emulsion includes, for example, perfluorodecalin, pluronic F108, perfluoroperhydrophenanthrene and distilled water.

US-Patent 3962439 beansprucht eine Perfluorocarbonemulsionin in der ein Phospholipid als Emulgator und eine Fettsäure und deren Metallsalz oder Monoglycerid enthalten sind US Patent 3962439 claims a perfluorocarbon emulsion in which a phospholipid as an emulsifier and a fatty acid and its metal salt or monoglyceride are contained

United States Patent Application 20100144861 beansprucht eine Perfluorocarbongel-Zusammensetzung, das 10–90 wt % Perfluorocarbon, welches Perfluoro-Tert-butylcyclohexan sein kann und 8–70 wt % Wasser enthält. Als Dispergator werden Polyoxyethylene-Polyoxypropylen-Blockcopolymere eingesetzt, wie Poloxamer 105 und Poloxamer 188. United States Patent Application 20100144861 claims a perfluorocarbon gel composition which may be 10-90 wt% perfluorocarbon, which may be perfluoro tert-butyl cyclohexane and contains 8-70 wt% water. The dispersant used are polyoxyethylene-polyoxypropylene block copolymers, such as poloxamer 105 and poloxamer 188.

Ein Nachteil solcher Emulsionen ist, dass sie nicht dauerhaft stabil sind, so dass es im Verlauf von Wochen oder Monaten zu Entmischungsvorgängen, verbunden mit dem Wachstum von Tropfen, kommt. Es wird deshalb vorgeschlagen, die Lagerstabilität der Emulsionen durch Anwendung von komplexen Gemischen von Emulgatoren oder Gemischen von verschiedenen Fluorocarbonverbindungen zu verbessern.A disadvantage of such emulsions is that they are not permanently stable so that segregation processes associated with the growth of drops occur over weeks or months. It is therefore proposed to improve the storage stability of the emulsions by using complex mixtures of emulsifiers or mixtures of different fluorocarbon compounds.

Zum Beispiel beanspruchen US2011/0306581A1 und WO2010077671 Perfluorocarbonemulsion mit verbesserter Stabilität unter Verwendung von Polyethylenoxid-Blockcopolymeren.For example, claim US2011 / 0306581A1 and WO2010077671 Perfluorocarbon emulsion with improved stability using polyethylene oxide block copolymers.

In DE 10 2009 026 718 A1 wird die Anwendung von Fluorcarbonen zur Hautbehandlung zur Porenverfeinerung vorgeschlagen. Dazu werden die Fluorcarbone mit vergleichsweise großem Aufwand in Liposomen oder Vesikeln eingeschlossen.In DE 10 2009 026 718 A1 the use of fluorocarbons for skin treatment for pore refining is proposed. For this purpose, the fluorocarbons are enclosed in liposomes or vesicles with comparatively great effort.

Ziel der Erfindung ist deshalb eine verbesserte Stabilität von Perfluorocarbonemulsionen und eine Verringerung des Aufwandes zur Herstellung derartiger Emulsionen.The aim of the invention is therefore an improved stability of perfluorocarbon emulsions and a reduction of the effort for the preparation of such emulsions.

Erfindungsgemäß wird diese Aufgabe durch die Perfluorocarbonemulsion mit den Merkmalen des Anspruchs 1 gelöst. Weitere spezielle oder bevorzugte Ausführungsformen der vorliegenden Erfindung sind Gegenstand der abhängigen Ansprüche.According to the invention, this object is achieved by the perfluorocarbon emulsion having the features of claim 1. Further specific or preferred embodiments of the present invention are the subject of the dependent claims.

Überraschend zeigte sich, dass Polyelektrolyte vorteilhaft als Emulgatoren zur Herstellung von Perfluorocarbonemulsionen verwendbar sind. Das ist besonders überraschend, da erfindungsgemäß auch stark hydrophile Polyelektrolyte als Emulgatoren zur Herstellung von Perfluorocarbonemulsionen verwendbar sind. Es handelt sich dabei nicht um Verbindungen mit hydrophilen und lipophilen Anteilen, wie die herkömmlich als Emulgatoren verwendeten Tenside. Polyelektrolyte sind wasserlösliche Verbindungen mit großer Kettenlänge (Polymere), die anionische (Polysäuren) oder kationische (Polybasen) dissoziierbare Gruppen tragen. Das können zum Beispiel Acrylamid-Copolymere, Alginate, Ligninsulfonate, Pektine, Polyacrylsäuren und entsprechende Copolymere, Polyvinylschwefelsäure, Polycarbonsäuren Polyphosphorsäuren, Polysaccharide, Aminopolysiloxane, Polystyrolsulfonat, Phenole, Poly-Diallyldimethyl-ammoniumchlorid, Polyethylenimin, Polyvinylamin, Polyvinylpyridin und Polyvinylammoniumchlorid sein. Vorteilhaft einsetzbar sind aber auch Naturprodukte bzw. modifizierte Naturprodukte, wie Chitosan. In den bekannten Perfluorocarbonemulsionen werden derartige Materialien teilweise zur Erhöhung der Viskosität eingesetzt. Eine Verwendung als Emulgator wurde bisher noch nicht beschrieben.Surprisingly, it has been found that polyelectrolytes can be advantageously used as emulsifiers for the production of perfluorocarbon emulsions. This is particularly surprising because, according to the invention, highly hydrophilic polyelectrolytes can also be used as emulsifiers for the preparation of perfluorocarbon emulsions. These are not compounds with hydrophilic and lipophilic components, such as the surfactants conventionally used as emulsifiers. Polyelectrolytes are water soluble long chain compounds (polymers) bearing anionic (polyacids) or cationic (polybases) dissociable groups. These may be, for example, acrylamide copolymers, alginates, ligninsulfonates, pectins, polyacrylic acids and corresponding copolymers, polyvinylsulfuric acid, polycarboxylic acids, polyphosphoric acids, polysaccharides, aminopolysiloxanes, polystyrenesulfonate, phenols, poly-diallyldimethylammonium chloride, polyethylenimine, polyvinylamine, polyvinylpyridine and polyvinylammonium chloride. However, natural products or modified natural products such as chitosan are also advantageously usable. In the known perfluorocarbon emulsions, such materials are sometimes used to increase the viscosity. A use as an emulsifier has not yet been described.

Die erfindungsgemäße Emulsion kann vorteilhaft im Gemisch mit bereits bekannten hautpflegenden oder wundheilungsfördernden Komponenten zur Verbesserung der Sauerstoffversorgung von menschlichem Gewebe, insbesondere der Haut oder von Wundgewebe eingesetzt werden. Zum Beispiel sind Komponenten geeignet, die natürliche Bestandteile der Haut sind bzw. diesen weitgehend entsprechen. Das können Hautlipide sein, wie Triglyzeride, Squalane, Ceramide, Phospholipide, Cholesterol bzw. Phytosterole. Vorteilhaft ist weiterhin der Zusatz von Komponenten, die eine Erweiterung von Blutgefäßen und damit eine verstärkte Durchblutung des Gewebes bewirken. Das kann zum Beispiel L-Arginin sein.The emulsion according to the invention may advantageously be used in admixture with already known skin-care or wound-healing-promoting components for improving the oxygen supply of human tissue, in particular the skin or wound tissue. For example, components which are natural components of the skin or largely correspond to them are suitable. These may be skin lipids, such as triglycerides, squalane, ceramides, phospholipids, cholesterol or phytosterols. Another advantage is the addition of components that cause dilation of blood vessels and thus increased blood flow to the tissue. This can be L-arginine, for example.

Ausführungsbeispiel 1Embodiment 1

Zu 0,33 g Perfluorodecalin werden 0,08 g einer 10%igen wässrigen Polyacrylsäurelösung und 2,38 g Wasser gegeben. Das zweiphasige Gemisch wird mittels einer Ultraschallsonotrode mit Ultraschall behandelt. In wenigen Sekunden tritt eine vollständige Dipergierung des Perfluorodecalins ein. Die so hergestellte Perfluorodecalinemulsion ist zur Verbesserung Sauerstoffversorgung von Haut oder Wundgewebe geeignet.To 0.33 g of perfluorodecalin is added 0.08 g of a 10% aqueous solution of polyacrylic acid and 2.38 g of water. The biphasic mixture is sonicated by an ultrasonic sonotrode. In a few seconds, a complete perfluorodecalin dipergation occurs. The perfluorodecalin emulsion thus prepared is suitable for improving the oxygenation of skin or wound tissue.

Ausführungsbeispiel 2Embodiment 2

Zu 0,4 g Perfluorodecalin werden 0,025 g Lupamin 9095 und 2,38 g Wasser gegeben. Das zweiphasige Gemisch wird mittels einer Ultraschallsonotrode mit Ultraschall behandelt. In wenigen Sekunden tritt eine vollständige Dipergierung des Perfluorodecalins ein. Die so hergestellte Perfluorodecalinemulsion ist zur Verbesserung Sauerstoffversorgung von Haut oder Wundgewebe geeignet.To 0.4 g of perfluorodecalin 0.025 g Lupamin 9095 and 2.38 g of water are added. The biphasic mixture is sonicated by an ultrasonic sonotrode. In a few seconds, a complete perfluorodecalin dipergation occurs. The perfluorodecalin emulsion thus prepared is suitable for improving the oxygenation of skin or wound tissue.

ZITATE ENTHALTEN IN DER BESCHREIBUNG QUOTES INCLUDE IN THE DESCRIPTION

Diese Liste der vom Anmelder aufgeführten Dokumente wurde automatisiert erzeugt und ist ausschließlich zur besseren Information des Lesers aufgenommen. Die Liste ist nicht Bestandteil der deutschen Patent- bzw. Gebrauchsmusteranmeldung. Das DPMA übernimmt keinerlei Haftung für etwaige Fehler oder Auslassungen.This list of the documents listed by the applicant has been generated automatically and is included solely for the better information of the reader. The list is not part of the German patent or utility model application. The DPMA assumes no liability for any errors or omissions.

Zitierte PatentliteraturCited patent literature

  • US 4859363 [0004] US 4859363 [0004]
  • US 3962439 [0005] US 3962439 [0005]
  • US 20100144861 [0006] US 20100144861 [0006]
  • US 2011/0306581 A1 [0008] US 2011/0306581 A1 [0008]
  • WO 2010077671 [0008] WO 2010077671 [0008]
  • DE 102009026718 A1 [0009] DE 102009026718 A1 [0009]

Zitierte Nicht-PatentliteraturCited non-patent literature

  • Donat R Spahn, Blood substitutes Artificial oxygen carriers: perfluorocarbon emulsions, Crit Care. 1999; 3(5): R93–R97. Published online 1999 September 24 [0003] Donat R Spahn, Blood substitutes Artificial oxygen carriers: perfluorocarbon emulsions, Crit Care. 1999; 3 (5): R93-R97. Published online 1999 September 24 [0003]

Claims (6)

Perfluorocarbonemulsion, dadurch gekennzeichnet, dass in der Emulsion neben mindestens einer Perfluorocarbonverbindung und Wasser mindestens ein Polyelektrolyt vorhanden ist.Perfluorocarbonemulsion, characterized in that in the emulsion in addition to at least one perfluorocarbon compound and water at least one polyelectrolyte is present. Perfluorocarbonemulsion nach 1, dadurch gekennzeichnet, dass sich darin, außer mindestens einem Polyelektrolyten, kein weiterer Emulgator befindetPerfluorocarbonemulsion according to 1, characterized in that it contains, except at least one polyelectrolyte, no further emulsifier Perfluorocarbonemulsion nach 1 oder 2, dadurch gekennzeichnet, dass es sich bei dem Polyelektrolyten um Acrylamid-Copolymere, Alginate, Chitosan, Ligninsulfonate, Pektine, Polyacrylsäuren und entsprechende Co-Polymere, Polyvinylschwefelsäure, Polycarbonsäuren, Polyphosphorsäuren, Polysaccharide, Aminopolysiloxane, Polystyrolsulfonat, Phenole, Poly-Diallyldimethyl-ammoniumchlorid, Polyethylenimin, Polyvinylamin, Polyvinylpyridin oder Polyvinylammoniumchlorid handelt.A perfluorocarbon emulsion according to 1 or 2, characterized in that the polyelectrolyte is acrylamide copolymers, alginates, chitosan, ligninsulfonates, pectins, polyacrylic acids and corresponding copolymers, polyvinylsulfuric acid, polycarboxylic acids, polyphosphoric acids, polysaccharides, aminopolysiloxanes, polystyrenesulfonate, phenols, poly Diallyldimethylammonium chloride, polyethylenimine, polyvinylamine, polyvinylpyridine or polyvinylammonium chloride. Perfluorocarbonemulsion nach 1 bis 3, dadurch gekennzeichnet, dass die Emulsion zur Verbesserung der Sauerstoffversorgung von menschlichem Gewebe, insbesondere der Haut oder von Wundgewebe eingesetzt wird.Perfluorocarbonemulsion according to 1 to 3, characterized in that the emulsion for improving the oxygen supply of human tissue, in particular the skin or wound tissue is used. Perfluorocarbonemulsion nach 1 bis 4, dadurch gekennzeichnet, dass die Emulsion im Gemisch mit bereits bekannten hautpflegenden oder wundheilungsfördernden Komponenten zur Verbesserung der Sauerstoffversorgung von menschlichem Gewebe, insbesondere der Haut oder von Wundgewebe eingesetzt wird.Perfluorocarbonemulsion according to 1 to 4, characterized in that the emulsion is used in admixture with already known skin-care or wound healing promoting components for improving the oxygenation of human tissue, especially the skin or wound tissue. Perfluorocarbonemulsion nach 1 bis 5, dadurch gekennzeichnet, dass die Emulsion innerhalb von wenigen Sekunden nur unter Einwirkung von Ultraschall herstellbar istPerfluorocarbonemulsion according to 1 to 5, characterized in that the emulsion can be produced within a few seconds only under the action of ultrasound
DE201210014465 2012-07-18 2012-07-18 Emulsion, useful in a mixture with known skin care or wound-healing components for improving oxygen supply of human tissue, preferably skin or wound tissue, comprises perfluorocarbon compound and water, and polyelectrolyte Withdrawn DE102012014465A1 (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102013018565A1 (en) 2013-10-28 2015-04-30 Gmbu E.V., Fachsektion Dresden Personal care products and their use

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3962439A (en) 1973-10-05 1976-06-08 The Green Cross Corporation Oxygen-transferable emulsion
US4859363A (en) 1985-02-26 1989-08-22 I.S.C. Chemicals Limited Emulsions of perfluorocarbons in aqueous media
DE102009026718A1 (en) 2009-06-04 2010-04-15 Henkel Ag & Co. Kgaa Cosmetic non-therapeutic use of at least one fluorocarbon, which is a perfluorinated hydrocarbon compound, in a topical composition for reducing the pore size of the skin, preferably facial skin
US20100144861A1 (en) 2008-11-25 2010-06-10 Gary Huvard Perfluorocarbon gel formulations
WO2010077671A2 (en) 2008-12-08 2010-07-08 University Of Utah Research Foundation Stable perfluorocarbon emulsion for use as an artificial oxygen carrier

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3962439A (en) 1973-10-05 1976-06-08 The Green Cross Corporation Oxygen-transferable emulsion
US4859363A (en) 1985-02-26 1989-08-22 I.S.C. Chemicals Limited Emulsions of perfluorocarbons in aqueous media
US20100144861A1 (en) 2008-11-25 2010-06-10 Gary Huvard Perfluorocarbon gel formulations
WO2010077671A2 (en) 2008-12-08 2010-07-08 University Of Utah Research Foundation Stable perfluorocarbon emulsion for use as an artificial oxygen carrier
US20110306581A1 (en) 2008-12-08 2011-12-15 University Of Utah Research Foundation Stable perfluorocarbon emulsion for use as an artificial oxygen carrier
DE102009026718A1 (en) 2009-06-04 2010-04-15 Henkel Ag & Co. Kgaa Cosmetic non-therapeutic use of at least one fluorocarbon, which is a perfluorinated hydrocarbon compound, in a topical composition for reducing the pore size of the skin, preferably facial skin

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Donat R Spahn, Blood substitutes Artificial oxygen carriers: perfluorocarbon emulsions, Crit Care. 1999; 3(5): R93-R97. Published online 1999 September 24

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102013018565A1 (en) 2013-10-28 2015-04-30 Gmbu E.V., Fachsektion Dresden Personal care products and their use

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