DOCSLIB.ORG

United States Patent (19) 11) Patent Number: 4,859,363 Davis Et Al

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
United States Patent (19) 11) Patent Number: 4,859,363 Davis Et Al United States Patent (19) 11) Patent Number: 4,859,363 Davis et al. (45) Date of Patent: Aug. 22, 1989 54 EMULSIONS OF PERFLUOROCARBONS IN (56) References Cited AQUEOUSMEDIA U.S. PATENT DOCUMENTS (75) Inventors: Stanley S. Davis, Nottingham; David 3,775,489 11/1973 Margrave et al. .................. 570/130 E. M. Wotton, Bristol, both of United 3,778,381 12/1973 Rosano et al. ....... ... 252/32 X Kingdom 3,823,091 7/1974 Samejima et al. ... o os e s vs 252/312 73) Assignee: I.S.C. Chemicals Limited, London, 3,911,138 10/1975 Clark, Jr. ......... ... 514/756 X United Kingdom 3,993,581 11/1976 Yokoyama et al.................. 252/312 21 Appl. No.: 143,282 Primary Examiner-Richard D. Lovering Attorney, Agent, or Firm-Fleit, Jacobson, Cohn, Price, 22 Filed: Jan. 7, 1988 Holman & Stern Related U.S. Application Data (57) ABSTRACT 63 Continuation of Ser. No. 833,017, Feb. 26, 1986, aban Increased stability is conferred on oil-in-water emul doned. sions of perfluorocarbons by addition of a minor (30) Foreign Application Priority Data (0.1-5% w/v) amount of a fluorinated compound of higher boiling point than the perfluorocarbon being Feb. 26, 1985 GB United Kingdom ................. 8504916 emulsified. The added fluorinated compound is prefera 51) Int. Cl." ....................... A61K9/10; A61K 31/25; bly a perfluorinated saturated polycyclic hydrocarbon. B01J 13/00 The most preferred additive is perfluoroperhydrofluo 52 U.S. C. .................................... 252/312; 514/755; ranthene. 514/832 58) Field of Search ................ 252/312; 514/755, 832; 570/130 6 Claims, 2 Drawing Sheets U.S. Patent Aug. 22, 1989 Sheet 1 of 2 4,859,363 Absolute Stability Cont [-ja ZZZZZZZ7777777||5 ?///////////////71., LT-15ZZZZZZZZZZZZZZZZZZZZZZZZZZZ? 0.8 quae Stability Data cr: Day k.k. O°C 37°C 0.4 0.2 U.S. Patent Aug. 22, 1989 Sheet 2 of 2 4859,363 cae cae 0.6 0.4 |(~15 LL ?CD cô 0.2 7777777777777||5 L-1=ZZZZZZZZZZZZZZZ…, [-]=;ZZZZZZZZZZZZZZZZZZZZZZZ) ©cae 0.6 Absolute Stability Ok FG4. O2 4,859,363 1. 2. Ostwald ripening (see e.g. Davis et al. (1981) J. Colloid EMUSONS OF PERFLUOROCARBONS IN Interface Sci. 80:508). AQUEOUSMEDIA Molecular diffusion will occur if the oil has a finite solubility in water and if the particles are very small. It This is a continuation of application Ser. No. 5 will occur even if the droplets have excellent barriers to 06/833/017, filed Feb. 26, 1986, now abandoned. coalescence but can be prevented in hydrocarbon emul This invention relates to emulsions of perfluorocar sions using mixed oil systems, that is by the addition of bons in aqueous media, to provide emulsions suitable for a very small quantity of higher boiling point material carrying oxygen or other gases, e.g. in an artificial (e.g. soyabean oil). Thus, if molecular diffusion is the blood application. 10 cause of instability in perfluorodecalin emulsions, at It has long been hypothesised that emulsions of cer tempts at creating even more effective barriers to co tain perfluorocarbons in aqueous media could constitute alescence will be to no avail. Similar considerations ideal blood substitutes, chiefly because of their inertness apply to any pure perfluorocarbon system. and their ability to transport oxygen and other life-sup porting materials around a human or animal body. 15 BRIEF DESCRIPTION OF THE DRAWINGS Normally such emulsions are formed with the aid of FIGS. 1-4 show the stability of the emulsions as a a non-ionic surface-active agent such as those known as function of the presence of C13 and C16 at different times polaxamers (as hereinafter defined) or a phosphatide and at different temperatures. (egg or soy lecithin). However a problem inherent in such emulsion tech 20 DETALED DESCRIPTION OF THE nology is the tendency of the emulsion to de-stabilize on INVENTION storage and for the emulsion droplets to grow in size. According to the present invention there is provided For some time, various workers have been studying an oil-in-water emulsion of a perfluorinated hydrocar the properties of perfluorochemicals and their potential 25 bon in an aqueous medium, wherein the emulsion is use as blood substitutes, not only for blood transfusion stabilized by the addition of a minor amount of a fluori but also for tissue oxygenation (cancer chemotherapy), nated compound of a higher boiling point than the per treatment of infarct, as scanning agents in nuclear mag fluorinated compound being emulsified. netic resonance, and for the preservation of organ trans Preferably the fluorinated compound of higher boil plants. The literature contains a wealth of information 30 ing point is a perfluorinated saturated polycyclic hydro on the preparation of various emulsion systems, the carbon, such as one of the following: properties of various fluorocarbon liquids and their perfluoroperhydrofluorene, C13F22 clearance from the body of animals, as well as some perfluoroperhydrophenanthrene, C14F24 limited clinical studies conducted in Japan and else perfluoroperhydrofluoranthene, C16F26 where. At the present time, the Green Cross Corpora 35 Of the above, perfluoroperhydrofluoranthene is par tion of Japan have available two commercial emulsion ticularly preferred. systems that seem to show good promise in clinical The fluorinated compound of higher boiling point is studies. However a major problem still exists with re suitably added in an amount of from 0.1 to 5% (w/v) of gard to the stability of emulsions produced with fluoro the stabilized emulsion, more preferably from 0.5% to carbons that have acceptable clearance characteristics. 40 2% (w/v). By far the most information available exists on the The perfluorinated hydrocarbon forming the emul material perfluorodecalin. This seems to be ideal in sion is preferably perfluorodecalin. terms of its low biological toxicity as well as its accept Other examples of fluorinated compounds of higher able clearance from the body after administration. Un boiling point include materials sold under the trade fortunately this compound does not give emulsions,. 45 names KRYTOX (RTM) and GALDEN (RTM) (per stable at room temperature for extended periods, with fluoroethylene oxide/propylene oxide copolymers). out resorting to complex mixtures of emulsifying sub It is believed that the higher boiling component of the stances or to mixtures of fluorocarbons. As a conse emulsion acts to stabilize the composition by dissolving quence, a detailed effort is being made, by various re n the fluorocarbon oil and thus by suppressing the de search groups, to produce an emulsion which has better 50 stabilizing "Ostwald ripening" effect which is inherent physiological and stability characteristics. In some in such an oil-in-water emulsion and gives rise to insta cases, the physiological requirements have even taken bility problems in other commercial formulations such second place to the stability requirement. as FLUOSOL-DA (RTM). We believe that the two aspects of stability and physi Preferably the emulsion is formed with the aid of a ological behaviour may not be separable; that is a per 55 surface active agent of the poloxamer type. Poloxamers fluorocarbon which gives the required physiological are a class of non-ionic surface active agents being po effects will, as a consequence, also be somewhat unsta lyoxyethylene-polyoxypropylene-polyoxyethylene ble when emulsified, and moreover, that other research block co-polymeric surfactants, sold under the trade groups appear to have considered emulsion stability in a name pluronic. - too simplistic way. The major way in which the drop 60 lets in emulsions can grow in size is by a process of The invention in another aspect provides the use as a droplet coalescence. Normally, this can be retarded, blood substitute of an emulsion of a perfluorocarbon in and practically eliminated, by using emulsifying agents an aqueous medium, according to the first aspect of the that can form electrostatic and mechanical barriers at invention. the oil/water interface. However, a much more subtle 65 The invention in a further aspect provides a method means of instability can occur in which the small parti of stabilizing an oil-in-water emulsion of a perfluori cles become small and the large particles become bigger nated hydrocarbon in an aqueous medium, wherein through a process of molecular diffusion, known as there is added to the said emulsion a minor amount of a 4,859,363 3 4. fluorinated compound of higher boiling point than the TABLE 1. perfluorinated compound emulsified. Stability Testing of Fluorocarbon Emulsions The invention will be further described with refer Coulter Counter Analysis: reported as % change in cumulative percentage oversize after 7 days storage at ence to the following illustrative Examples, which de 5 roon ten perature. scribe the making of typical formulations according to Change in this invention (Examples 1a to 1c), together with the percentage procedure used to test the emulsions for stability (Ex Example greater than ample 2 and Table 1). No. Emulsion type 0.83 um 1.05 um O la Perfluorodecalin -- EXAMPLE 1 Perfluoroperhydrofluorene O - 4 b Perfluorodecalin -- Preparation of perfluorochemical emulsions with Perfluoroperhydrofluoranthene 2 c Perfluorodecalin -- enhanced stability Perfluorperhydrophenanthene 4. 2 Emulsions were prepared using an ultrasonic 15 d Perfluorodecain alone homogeniser (Dawe Soniprobe) (10 minutes homogeni (as control) 14 10 sation at setting 5). The formulae were as follows for 50 The invention will be further described with refer ml of emulsion: ence to the accompanying drawings, wherein FIGS. 1 Example la 20 to 4 are bar charts (histograms) which illustrate the stability of emulsions formed from perfluorodecalin in Perfluorodecalin, 10 mi (20g) aqueous media without addition of a higher-boiling Pluronic F108 (Poloxamer 388), 1 g component and with the addition of higher-boiling Perfluoroperhydrofluorene, 0.5 ml (1 g)(2% w/v) components defined as follows: r Distilled water to 100%, to 50 m 25 C13: Perfluoroperhydrofluorene (C13F22) C16: Perfluoroperhydrofluoranthene (C16F26) Example lb In these bar-charts stability is expressed as a fraction of perfect stability (i.e.
Load more

Recommended publications
  • Concentrated Stable Fluorchemical Aqueous Emulsions
    Europaisches Patentamt © J European Patent Office © Publication number: 0 282 949 Office europeen des brevets A2 © EUROPEAN PATENT APPLICATION (y Application number: 88104014.1 © mt. ci.«: A61K 9/00 , A61 K 9/50 , A61 K 47/00 © Date of filing: 14.03.88 © Priority: 20.03.87 US 28521 © Applicant: AIR PRODUCTS AND CHEMICALS, INC. © Date of publication of application: Route no. 222 21.09.88 Bulletin 88/38 Trexlertown Pennsylvania 18087(US) © Designated Contracting States: © Inventor: Schweighardt, Frank Kenneth BE CH DE ES FR GB IT Li NL SE 509 Bastian Lane Rd No. 3 Allentown, PA 18104(US) Inventor: Kayhart, Charles Randall Baidy Hill Road P.O.B. 195 Alburtis, PA 18011 (US) © Representative: Dipi.-lng. Schwabe, Dr. Dr. Sandmair, Dr. Marx Stuntzstrasse 16 D-8000 MUnchen 80(DE) © Concentrated stable fluorchemical aqueous emulsions. © A stable concentrated aqueous emulsion of perfluorochemical, a phospholipid and a triglyceride of fatty acids has been demonstrated which has enhanced stability, diminished particle size and heightened tolerance by biological systems. The emulsion has utility as an oxygen transport medium, such as artificial blood. The emulsion can optionally include addition emulsifiers of SURFYNOL®SE surfactant and PLURONIC® P-105 surfactant. The emulsion is produced using an improved emulsification technique. < 03 CM CO a. Ill Xerox Copy Centre 0 282 949 CONCENTRATED STABLE FLUOROCHEMICAL AQUEOUS EMULSIONS TECHNICAL FIELD The present invention is directed to biologically acceptable oxygen transport media comprising high s concentration aqueous emulsions of perfluorochemicals in complex emulsification systems. More specifi- cally, the present invention is directed to an aqueous perfluorochemical emulsion having utility in the field of resuscitative fluids for oxygen transport and volume expansion in mammals, such as artificial or synthetic blood.
    [Show full text]
  • (Title of the Thesis)*
    FLUOROCARBENE, FLUOROALKYL, AND FLUORIDE COMPLEXES OF FIRST-ROW TRANSITION METALS Graham Mark Lee Thesis submitted to the Faculty of Graduate and Postdoctoral Studies University of Ottawa In partial fulfillment of the requirements for the degree of Doctor of Philosophy Ottawa-Carleton Chemistry Institute Faculty of Science University of Ottawa © Graham Mark Lee, Ottawa, Canada, 2017 Abstract Fluorinated organic compounds play important roles in our society, as these products range from life-saving pharmaceuticals and agrochemicals, to fluoropolymers with extremely high thermal and chemical stability. Although elemental fluorine (F2) is the most reactive element, some fluoro- organic compounds are chemically inert. As such, controlled reactivity of fluorine or highly- fluorinated organic fragments is a considerable, yet important challenge for synthetic chemists. Fluoro-organometallic chemistry has been studied for decades, as researchers attempt to maximize the potential of metal mediated/catalyzed processes for the synthesis of fluorinated organic molecules. Within this framework, metal fluorocarbene complexes are particularly interesting because of their highly tunable reactivity, and are proposed for use in important metathesis/polymerization reactions of perfluorinated alkenes. While considerable work is still needed to make these proposed reactions a reality, this thesis outlines contributions from our F F research group. We showed that cobalt fluorocarbene complexes CpCo(=CFR )(PPh2Me) (R = F, CF3) undergo [2+2] cycloaddition reactions with tetrafluoroethylene (TFE) and phenylacetylene to form perfluorometallacyclobutane and partially fluorinated metallacyclobutene products, respectively. For both reactions, computational studies reveal a stepwise ring-closing mechanism, which proceeds through a singlet 1,4-diradical intermediate. Next, the formation of CpCo(=CF2)(L) complexes is achieved via the direct addition of difluorocarbene, generated in situ, to a cobalt(I) precursor.
    [Show full text]
  • "Fluorine Compounds, Organic," In: Ullmann's Encyclopedia Of
    Article No : a11_349 Fluorine Compounds, Organic GU¨ NTER SIEGEMUND, Hoechst Aktiengesellschaft, Frankfurt, Federal Republic of Germany WERNER SCHWERTFEGER, Hoechst Aktiengesellschaft, Frankfurt, Federal Republic of Germany ANDREW FEIRING, E. I. DuPont de Nemours & Co., Wilmington, Delaware, United States BRUCE SMART, E. I. DuPont de Nemours & Co., Wilmington, Delaware, United States FRED BEHR, Minnesota Mining and Manufacturing Company, St. Paul, Minnesota, United States HERWARD VOGEL, Minnesota Mining and Manufacturing Company, St. Paul, Minnesota, United States BLAINE MCKUSICK, E. I. DuPont de Nemours & Co., Wilmington, Delaware, United States 1. Introduction....................... 444 8. Fluorinated Carboxylic Acids and 2. Production Processes ................ 445 Fluorinated Alkanesulfonic Acids ...... 470 2.1. Substitution of Hydrogen............. 445 8.1. Fluorinated Carboxylic Acids ......... 470 2.2. Halogen – Fluorine Exchange ......... 446 8.1.1. Fluorinated Acetic Acids .............. 470 2.3. Synthesis from Fluorinated Synthons ... 447 8.1.2. Long-Chain Perfluorocarboxylic Acids .... 470 2.4. Addition of Hydrogen Fluoride to 8.1.3. Fluorinated Dicarboxylic Acids ......... 472 Unsaturated Bonds ................. 447 8.1.4. Tetrafluoroethylene – Perfluorovinyl Ether 2.5. Miscellaneous Methods .............. 447 Copolymers with Carboxylic Acid Groups . 472 2.6. Purification and Analysis ............. 447 8.2. Fluorinated Alkanesulfonic Acids ...... 472 3. Fluorinated Alkanes................. 448 8.2.1. Perfluoroalkanesulfonic Acids
    [Show full text]
  • And Perfluoroalkyl Substances (PFAS): Sources, Pathways and Environmental Data
    Poly- and perfluoroalkyl substances (PFAS): sources, pathways and environmental data Chief Scientist’s Group report August 2021 We are the Environment Agency. We protect and improve the environment. We help people and wildlife adapt to climate change and reduce its impacts, including flooding, drought, sea level rise and coastal erosion. We improve the quality of our water, land and air by tackling pollution. We work with businesses to help them comply with environmental regulations. A healthy and diverse environment enhances people's lives and contributes to economic growth. We can’t do this alone. We work as part of the Defra group (Department for Environment, Food & Rural Affairs), with the rest of government, local councils, businesses, civil society groups and local communities to create a better place for people and wildlife. Published by: Author: Emma Pemberton Environment Agency Horizon House, Deanery Road, Environment Agency’s Project Manager: Bristol BS1 5AH Mark Sinton www.gov.uk/environment-agency Citation: Environment Agency (2021) Poly- and © Environment Agency 2021 perfluoroalkyl substances (PFAS): sources, pathways and environmental All rights reserved. This document may data. Environment Agency, Bri be reproduced with prior permission of the Environment Agency. Further copies of this report are available from our publications catalogue: www.gov.uk/government/publications or our National Customer Contact Centre: 03708 506 506 Email: research@environment- agency.gov.uk 2 of 110 Research at the Environment Agency Scientific research and analysis underpins everything the Environment Agency does. It helps us to understand and manage the environment effectively. Our own experts work with leading scientific organisations, universities and other parts of the Defra group to bring the best knowledge to bear on the environmental problems that we face now and in the future.
    [Show full text]
  • Polytetrafluoroethylene: Synthesis and Characterization of the Original Extreme Polymer
    Polytetrafluoroethylene: Synthesis and Characterization of the Original Extreme Polymer Gerard J. Putsa, Philip Crousea and Bruno M. Amedurib* aDepartment of Chemical Engineering, University of Pretoria, Pretoria 0002, South Africa. b Ingenierie et Architectures Macromoléculaires, Institut Charles Gerhardt, UMR 5253 CNRS, UM, ENSCM, Place Eugène Bataillon, 34095 Montpellier Cedex 5, France. Correspondence to: Bruno Ameduri (E-mail: [email protected]) 1 ABSTRACT This review aims to be a comprehensive, authoritative, and critical review of general interest to the chemistry community (both academia and industry) as it contains an extensive overview of all published data on the homopolymerization of tetrafluoroethylene (TFE), detailing the TFE homopolymerization process and the resulting chemical and physical properties. Several reviews and encyclopedia chapters on the properties and applications of fluoropolymers in general have been published, including various reviews that extensively report copolymers of TFE (listed below). Despite this, a thorough review of the specific methods of synthesis of the homopolymer, and the relationships between synthesis conditions and the physico-chemical properties of the material prepared, has not been available. This review intends to fill that gap. As known, PTFE and its marginally modified derivatives comprise some 6065 % of the total international fluoropolymer market with a global increase of ca. 7 % per annum of its production. Numerous companies, such as Asahi Glass, Solvay Specialty Polymers, Daikin, DuPont/Chemours, Juhua, 3F and 3M/Dyneon, etc., produce TFE homopolymers. Such polymers, both high molecular-mass materials and waxes, are chemically inert, hydrophobic, and exhibit an excellent thermal stability as well as an exceptionally low co-efficient of friction. These polymers find use in applications ranging from coatings and lubrication to pyrotechnics, and an extensive industry (electronic, aerospace, wires and cables, as well as textiles) has been built around them.
    [Show full text]
  • Environmental Property Modeling of Perfluorodecalin and Its Implications for Environmental Fate and Hazards
    Aerosol and Air Quality Research, 11: 903–907, 2011 Copyright © Taiwan Association for Aerosol Research ISSN: 1680-8584 print / 2071-1409 online doi: 10.4209/aaqr.2010.12.0106 Environmental Property Modeling of Perfluorodecalin and its Implications for Environmental Fate and Hazards Wen-Tien Tsai* Graduate Institute of Bioresources, National Pingtung University of Science and Technology, Pingtung 912, Taiwan ABSTRACT In a variety of medical and industrial uses, small amounts of perfluorodecalin (C10F18) may have been released into the environment. However, it may significantly contribute to the global warming due to its highly radiative efficiency and global warming potential (GWP). Using the chemical similarity approach, this article aimed at calculating the fate properties and discussing the environmental implications of the perfluorinated compound for the purpose of mitigating its emissions. The environmental fate properties of perfluorodecalin, including octanol-water partition coefficient, water solubility and Henry’s law constant, were first estimated in the present study. These predicted values were further compared with those of other chemically similar compounds such as naphthalene, decalin and decane. From the computational findings, perfluorodecalin, which has exceptionally low solubility in water and high vaporization from the water bodies, tends to be hydrophobic and partitioned into organic matter, suggesting that it will sink into the atmosphere. Also addressed in the paper was a possible proposal for forming trifluoroacetic
    [Show full text]
  • Environmental Protection Agency
    Vol. 79 Thursday, No. 238 December 11, 2014 Part III Environmental Protection Agency 40 CFR Part 98 Greenhouse Gas Reporting Program: Addition of Global Warming Potentials to the General Provisions and Amendments and Confidentiality Determinations for Fluorinated Gas Production; Final Rule VerDate Sep<11>2014 19:57 Dec 10, 2014 Jkt 235001 PO 00000 Frm 00001 Fmt 4717 Sfmt 4717 E:\FR\FM\11DER3.SGM 11DER3 tkelley on DSK3SPTVN1PROD with RULES3 73750 Federal Register / Vol. 79, No. 238 / Thursday, December 11, 2014 / Rules and Regulations ENVIRONMENTAL PROTECTION Production source category to reduce 566–1744 and the telephone number for AGENCY the level of detail in which emissions the Air Docket is (202) 566–1742. are reported, eliminate the mass-balance FOR FURTHER INFORMATION CONTACT: 40 CFR Part 98 emission calculation method, and Carole Cook, Climate Change Division, [EPA–HQ–OAR–2009–0927; FRL–9919–70– clarify the emission factor method. Office of Atmospheric Programs (MC– OAR] These amendments also include an 6207J), Environmental Protection alternative verification approach for this RIN 2060–AR78 Agency, 1200 Pennsylvania Ave. NW., source category in lieu of collecting Washington, DC 20460; telephone Greenhouse Gas Reporting Program: certain data elements for which the EPA number: (202) 343–9263; fax number: Addition of Global Warming Potentials has identified disclosure concerns and (202) 343–2342; email address: to the General Provisions and for which the reporting deadline was [email protected]. For technical Amendments and Confidentiality deferred until March 31, 2015. In information, please go to the Determinations for Fluorinated Gas addition, this action establishes Greenhouse Gas Reporting Rule Program Production confidentiality determinations for Web site at http://www.epa.gov/ certain reporting requirements of the ghgreporting/index.html.
    [Show full text]
  • Stable Emulsions of Highly Fluorinated Organic Compound
    ratentamt JcuropaiscnesEuropean Patent Office Qj) Publication number: 0 231 091 Office europeen des brevets A1 tUHUPEAN PATENT APPLICATION (21) Application number: 87300454.3 © Int. CI.3: A 61 K 9/10 A 61 K 31/02 © Dateoffiling: 20.01.87 (30) Priority: 24.01.86 US 822291 5) Applicant: CHILDREN'S HOSPITAL MEDICAL CENTER 09.07.86 US 883713 Elland and Bethesda Avenues Cincinnati Ohio 45229(US) \*3; Date of publication of application : © Applicant: HemaGenPFC 05.08.87 Bulletin 87/32 1177 California Street Suite 1600 San Francisco California 94108IUS) @ Designated Contracting States: AT BE CH DE ES FR GB GR IT LI LU NL SE © Inventor: Clark, LelandC. Jr. 218 Greendate Avenue Cincinnati, Ohio 45229(US) © Inventor: Shaw, Robert F. 1750 Taylor Street San Francisco California 94133(US) © Representative: Allen, Oliver John Richard et al, Lloyd Wise, TregearSiCo. Norman House 105-109 Strand London, WC2R0AE{GB) ■y oiauieomuisionsoinigniyTiuonnaiea organic compound. 5j) Stable emulsions of highly fluorinated organic com- lounds for use as oxygen transport agents, "artificial floods" or red blood cell substitutes and as contrast agents or biological imaging. The emulsions comprise a highly luorinated organic compound, an oil that is not substantially urface active and not significantly soluble in water, a sur- actant and water. 3 •i M tm u oyaon Printing Company Ltd 0231091 +1+ oTApLK emulsions of highly fluorinated organic compounds. This invention relates to stable emulsions of highly fluorinated organic compounds and to processes of making and using them, such emulsions are especially useful in compositions for use as oxygen transport agents, "artificial bloods" or red blood cell substitutes and as contrast agents for biological imaging.
    [Show full text]
  • Perfluorodecalin and Bone Regeneration F
    EuropeanF Tamimi Cells et al .and Materials Vol. 25 2013 (pages 22-36) DOI: 10.22203/eCM.v025a02 Perfluorodecalin and bone ISSN regeneration 1473-2262 PERFLUORODECALIN AND BONE REGENERATION F. Tamimi1,*, P. Comeau1, D. Le Nihouannen2, Y.L. Zhang1, D.C. Bassett1, S. Khalili1, U. Gbureck3, S.D. Tran1, S. Komarova1, and J.E. Barralet1 1Faculty of Dentistry, McGill University, Montreal, Quebec, Canada 2University of Bordeaux, Bordeaux, France 3University of Würzburg, Würzburg, Germany Abstract Introduction Perfluorodecalin (PFD) is a chemically and biologically Bone repair and regeneration is highly dependent on inert biomaterial and, as many perfluorocarbons, is also the progeny of mesenchymal stem cells (MSCs) and hydrophobic, radiopaque and has a high solute capacity for their ability to affect healing at an injured site. Upon gases such as oxygen. In this article we have demonstrated, bone injury, bone marrow (BM) provides large numbers both in vitro and in vivo, that PFD may significantly of MSCs that replicate and differentiate to lineages of enhance bone regeneration. Firstly, the potential benefit mesenchymal tissues, including bone, and marrow stroma of PFD was demonstrated by prolonging the survival of (Caplan, 1991; Pittenger et al., 1999; Jiang et al., 2002). bone marrow cells cultured in anaerobic conditions. These Despite these properties, MSCs alone have proven to findings translated in vivo, where PFD incorporated into be unable to promote bone repair, and they require the bone-marrow-loaded 3D-printed scaffolds substantially support of a scaffolding biomaterial. Synthetic scaffolds improved their capacity to regenerate bone. Secondly, in allow cell migration, growth and differentiation into the addition to biological applications, we have also shown site; however, they lack the biological activity of MSCs.
    [Show full text]
  • Stabilization of Fluorocarbon Emulsions Stabilisierung Von Fluorkohlenstoff-Emulsionen Stabilisation D'emulsions De Fluorocarbone
    ~™ llll III II II II II II IMI I II I II (19) J European Patent Office Office europeen des brevets (1 1 ) EP 0 666 736 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publicationation and mention (51) |nt. CI.6: A61 K 9/00 of the grant of the patent: 18.12.1996 Bulletin 1996/51 (86) International application number: PCT/US93/10286 (21) Application number: 94901211.6 (87) International publication number: (22) Date of filing : 27.1 0.1 993 WO 94/09625 (1 1 .05.1 994 Gazette 1 994/1 1 ) (54) STABILIZATION OF FLUOROCARBON EMULSIONS STABILISIERUNG VON FLUORKOHLENSTOFF-EMULSIONEN STABILISATION D'EMULSIONS DE FLUOROCARBONE (84) Designated Contracting States: (72) Inventors: AT BE CH DE DK ES FR GB GR IE IT LI LU MC NL • WEERS, Jeffry, Greg PTSE San Diego, CA 92129 (US) • KLEIN, David, Henry (30) Priority: 27.10.1992 US 967700 Carlsbad, CA 92008 (US) • JOHNSON, Cindy, Shizuko (43) Date of publication of application: Oceanside, CA 92056 (US) 16.08.1995 Bulletin 1995/33 (74) Representative: VOSSIUS & PARTNER (73) Proprietor: ALLIANCE PHARMACEUTICAL Postfach 86 07 67 CORPORATION 81634 Munchen (DE) San Diego California 92121 (US) (56) References cited: WO-A-93/01798 US-A- 4 859 363 CO CO CO r»- CD CO Note: Within nine months from the publication of the mention of the grant of the European patent, give CO any person may notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in o a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid.
    [Show full text]
  • (12) United States Patent (10) Patent No.: US 6,961,168 B2 Agrawal Et Al
    USOO696 1168B2 (12) United States Patent (10) Patent No.: US 6,961,168 B2 Agrawal et al. (45) Date of Patent: Nov. 1, 2005 (54) DURABLE ELECTROOPTIC DEVICES 4.902,108 A 2/1990 Byker ........................ 350/357 COMPRISING IONIC LIQUIDS 5,099,356 A * 3/1992 Ohsawa et al. ............. 359/270 (75) Inventors: Anoop Agrawal, Tucson, AZ (US); (Continued) John P. Cronin, Tucson, AZ (US); Juan C. L. Tonazzi, Tucson, AZ (US); FOREIGN PATENT DOCUMENTS Benjamin P. Warner, Los Alamos, NM (US); T. Mark McCleskey, Los JP O83294.79 6/1998 ......... CO7C/57/145 JP O1933.63 12/2001 .......... HO1M/10/40 Alamos, NM (US); Anthony K. WO O127690 4/2001 Burrell, Los Alamos, NM (US) WO O163350 8/2001 ........... GO2F/1/153 (73) Assignee: The Regents of the University of California, Los Alamos, NM (US) OTHER PUBLICATIONS (*) Notice: Subject to any disclaimer, the term of this Charles M. Gordon, “New Developments in Catalysis. Using patent is extended or adjusted under 35 Ionic Liquids, Applied Catalysis A: General, Vol. 222, pp. U.S.C. 154(b) by 24 days. 101-117, 2001. (21) Appl. No.: 10/741,903 (Continued) (22) Filed: Dec. 19, 2003 (65) Prior Publication Data Primary Examiner-Georgia Epps ASSistant Examiner William Choi US 2004/0257633 A1 Dec. 23, 2004 (74) Attorney, Agent, or Firm Samuel L. Borkowsky Related U.S. Application Data (57) ABSTRACT (63) Continuation-in-part of application No. 10/600,807, filed on Electrolyte Solutions for electrochromic devices Such as rear Jun. 20, 2003, now Pat. No. 6.853,472. view mirrors and displays with low leakage currents are (60) Provisional application No.
    [Show full text]
  • Risk Assessment of Fluorinated Substances in Cosmetic Products
    Risk assessment of fluorinated substances in cosmetic products Survey of chemical substances in consum- er products No. 169 October 2018 Publisher: The Danish Environmental Protection Agency Editors: Anna Brinch (COWI A/S) Allan Astrup Jensen (NIPSECT) Frans Christensen (COWI A/S) ISBN: 978-87-93710-94-8 The Danish Environmental Protection Agency publishes reports and papers about research and development projects within the environmental sector, financed by the Agency. The contents of this publication do not necessarily represent the official views of the Danish Environmental Protection Agency. By publishing this report, the Danish Environmental Protection Agency expresses that the content represents an important contribution to the related discourse on Danish environmental policy. Sources must be acknowledged. 2 The Danish Environmental Protection Agency / Risk assessment of fluorinated substances in cosmetic products Contents Preface 5 Summary and conclusion 6 1. Introduction 14 1.1 Background and purpose of the project 14 1.1.1 Purpose and delimitations 14 1.2 Regulation of cosmetic products 15 1.3 Description of the substances concerned 15 1.3.1 Limit values for the substances concerned 17 2. Survey of PFAS in cosmetic products 19 2.1 Method 19 2.2 Survey 19 2.2.1 Databases 19 2.2.2 Literature data 23 2.3 Summary of the survey 27 2.4 Criteria for selection of products for chemical analysis 27 3. Chemical analysis 29 3.1 Introduction 29 3.2 Method 29 3.2.1 Analytical method 30 3.3 Results 30 3.3.1 Selection of substances for hazard and risk assessment 36 4.
    [Show full text]