Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K38/00—Medicinal preparations containing peptides
  • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
  • A61K38/43—Enzymes; Proenzymes; Derivatives thereof
  • A61K38/46—Hydrolases (3)
  • A61K38/48—Hydrolases (3) acting on peptide bonds (3.4)
  • A61K38/482—Serine endopeptidases (3.4.21)
• • 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
  • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
  • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
  • B01J13/0091—Preparation of aerogels, e.g. xerogels
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
  • C09D5/16—Antifouling paints; Underwater paints
  • C09D5/1606—Antifouling paints; Underwater paints characterised by the anti-fouling agent
  • C09D5/1637—Macromolecular compounds
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
  • C09D5/16—Antifouling paints; Underwater paints
  • C09D5/1687—Use of special additives
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
  • C09D7/40—Additives
  • C09D7/60—Additives non-macromolecular
  • C09D7/61—Additives non-macromolecular inorganic
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
  • C09D7/40—Additives
  • C09D7/65—Additives macromolecular
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
  • C09D7/40—Additives
  • C09D7/70—Additives characterised by shape, e.g. fibres, flakes or microspheres
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K3/00—Use of inorganic substances as compounding ingredients
  • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
  • C08K3/20—Oxides; Hydroxides
  • C08K3/22—Oxides; Hydroxides of metals
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K3/00—Use of inorganic substances as compounding ingredients
  • C08K3/34—Silicon-containing compounds

Definitions

• the present invention relates to the field of gels and the use of gels as means for storage and controlled release of component therefrom.
• Sol-gel chemistry has been used for many years. Most research has been directed towards inorganic gels created by hydrolysis of metal alkoxides. NASA has developed aerogels where the strength and the heat insulation properties of these materials have been optimized. Many other scientists have been reporting on the use of gels and aerogels for control of drug delivery. Here the gel performs the role as a sponge absorbing medically active compounds for later slow release. The process of interest is here diffusion out of the inert gel material. Yet another direction of research has been to encapsulate large molecules like proteins or even live bacteria or cells into the gel network. It has been found that in many cases the enzymes encapsulated in the gel retain their activity. In special cases as observed with Lipases they may even display significantly enhanced activity when located in the gel network. The gel is thus used as a bioreactor where the enzyme is staying fixed while the reactants and the products diffuse in and out of the very open gel network. Also in these last two situations it is important that the gel is strong and that it can retain its properties during the processes.
• Aerogel particles have been proposed for use in controlled release of pharmaceuticals, see e.g. U.S. Pat. No. 6,994,842 B2.
• Active compounds are a necessity for protection against biological growth in the coatings field. Due to environmental restrictions against traditional biocides and fungicides the need for more environmentally acceptable solutions is growing. Even though attempts to use enzymes and/or other organic molecules can be found in literature the success is restricted.
• the water-borne systems may have stability problems since sedimentation during storage result in a pigment and binder precipitate and a water enzyme liquid phase.
• the enzyme react in an autodegradation whereby the enzyme activity is significantly reduced. For this purpose it would be highly significant if the enzyme could be prevented from degradation during storage.
• Aerogels have been known to be useful as additives in paint formulations since they among other properties may introduce thixotropic properties. This property allows industrial spraying of thicker films of good quality.
• WO 2002/074868 discloses thixotropic paint formulations comprising silica aerogel.
• the present invention provides a composition comprising a gel wherein is entrapped at least one active component such that release of said at least one active component from said composition is substantially caused by degradation of said gel.
• the present invention relates to a composition
• a composition comprising an aerogel wherein is entrapped at least one active component such that release of said at least one active component from said composition is substantially caused by degradation of said aerogel.
• the present invention relates to a composition
• a composition comprising an wet gel wherein is entrapped at least one active component such that release of said at least one active component from said composition is substantially caused by degradation of said gel.
• the gel is prepared in a solvent mixture identical in composition to the paint in which it is planned to be incorporated.
• said at least one active component substantially is not liberated from said composition by diffusion out of said composition.
• sol means a solution of various reactants that are undergoing hydrolysis and condensation reactions.
• the molecular weight of the oxide species produced continuously increases. As these species grow, they may begin to link together in a three-dimensional network.
• alcogel as used herein means a wet gel which can be removed from its original container and can stand on its own.
• An alcogel consists of two parts, a solid part and a liquid part.
• the solid part is formed by the three-dimensional network of linked oxide particles.
• the liquid part (the original solvent of the Sol) fills the free space surrounding the solid part.
• the liquid and solid parts of an alcogel occupy the same apparent volume.
• supercritical fluid means a substance that is above its critical pressure and critical temperature.
• a supercritical fluid possesses some properties in common with liquids (density, thermal conductivity) and some in common with gases (fills its container, does not have surface tension).
• aerogel as used herein means what remains when the liquid part of an alcogel is removed without damaging the solid part. Removal of the liquid part can be achieved by e.g. supercritical extraction. If made correctly, the aerogel retains the original shape of the alcogel and at least 50% (typically >85%) of the alcogel's volume.
• xerogel as used herein means what remains when the liquid part of an alcogel is removed by evaporation, or similar methods. Xerogels may retain their original shape, but often crack. The shrinkage during drying is often extreme ( ⁇ 90%) for some xerogels.
• cryogel as used herein means what remains when an alcogel is frozen and the previously liquid part of the alcogel is removed by evaporation keeping the alcogel frozen all the time. Cryogels may retain their original shape, but often crack. The shrinkage during drying may be substantial for some cryogels. Addition of suitable surfactants in the alcogel may relieve this problem.
• substantially as used herein means considerably such as when expressed as a percentage at least 25%, such as at least 40%, such as at least 50%, such as at least 75%, such as at least 85%, such as at least 95%.
• release of X is substantially caused by degradation of said gel means that release of X is caused considerably by degradation of said gel.
• the present invention reverse in a sense the priorities and thereby providing a new area of applications.
• molecules are entrapped in the gel, e.g. during the SOL-GEL process. Since pores in the gel frequently will be between 1 and 20 nm the network is capable of encapsulating large molecules where the gel network creates bottleneck for passing. Other smaller molecules may be retained by the strong interaction with the cavity walls in the gel. Thus the molecules claimed to be of interest for the invention are molecules displaying no pronounced tendency to leach out of the gel.
• the loaded gel prepared in the liquid form or as an aerogel, cryogel or xerogel is designed by its chemical composition to be degradable under the conditions where it is planned to be used.
• the degradation may be chemical—as it happens with hydrolysis in water—where the pH of the water strongly influences the hydrolysis rate of metal alkoxy based gels.
• the degradation may however be purely mechanical as it is occurring when grains of the gel are present at a surface where friction wear down the grains.
• the gel differs markedly from the classes 2 and 3 and in most cases from class 1 since optimization of strength occur for a completely different set of criteria in the space research.
• the encapsulation of molecules in the gel may have a number of effects to be exploited in the present invention changing the release profile during gel decomposition.
• the gels prepared according to this invention are foreseen to have application in
• Silica aerogels may be prepared according to traditional microparticle sol-gel processing.
• the coating has to degrade due to mechanical friction.
• the parameters that influence the polishing rate is the choice of binders, their concentration as well as the choice of pigments/fillers and their concentration.
• the water up-take can be reduced in several ways:
• the present invention provides an gel modified by an interpenetrating network of a polymer.
• the polymer is chosen to fulfil the criteria:
• polymers where the environmental and toxicological clearances already have been obtained.
• examples of such substances are polyethyleneglycols, polylactic acid, polyvinylalkohol, polyvinylpyrrolidone, poly-lysine, heparins, poly-hyaluronic acid, polysaccarides and many more.
• the gel is typically silica based.
• the silicon may fully or partly be replaced by other tri- or tetra-valent metal ions.
• an aerogel containing enzyme rely on the controlled availability of sufficient large quantities of enzyme at a give time to impede or reduce the evolution of the biofilm and the settlement of algae, mussels and barnacles in the bacteria film.
• Various enzymes may be suitable as active components in the composition of the present invention.
• the at least one enzyme or protein comprises at least one enzyme selected from the group consisting of hemicellulolytically active enzymes, amylolytically active enzymes and/or cellulolytically active enzymes.
• the one or more bioactive agent(s) comprises endopeptidases.
• the endopeptidase(s) comprises a Subtilisin (EC 3.4.21.62).
• the Subtilisin (EC 3.4.21.62) has the following characteristics: (i) optimum activity at a pH in the range of about 7-10, and (ii) optimum activity at a temperature in the range of about 55-65° C.
• the Subtilisin (EC 3.4.21.62) is in one embodiment Alcalase.
• the hemicellulolytically active enzyme(s) is selected from the group consisting of Endo-1,4-beta-xylanase (E.C. 3.2.1.8), Xylan endo-1,3-beta-xylosidase (E.C. 3.2.1.32). Glucuronoarabinoxylan endo-1,4-beta-xylanase (E.C. 3.2.1.136), Betamannosidase (E.C. 3.2.1.25), Mannan endo-1,4-beta-mannosidase (5 E.C. 3.2.1.78) and Mannan endo-1,6-beta-mannosidase (E.C. 3.2.1.101).
• Endo-1,4-beta-xylanase E.C. 3.2.1.8
• Xylan endo-1,3-beta-xylosidase E.C. 3.2.1.32
• the hemicellulolytically active enzyme is a xylanase.
• the xylanase is an endo-1,4-beta-xylanase (E.C. 3.2.1.8).
• the amylolytically active enzyme(s) can in one embodiment be an amylase.
• the one or more amylolytically active enzyme(s) is selected from the group consisting of ⁇ - and ⁇ -amylases, amyloglucosidases (E.C. 3.2.1.3), pullulanases, ⁇ -1,6-endoglucanases, ⁇ -1,4-exoglucanases and isoamylases.
• the one or more amylolytically active enzyme(s) can also be amyloglucosidase.
• amyloglucosidase is an 1,4-alpha-glucosidase.
• the anti-fouling composition agent comprises one or more gel(s) and at least one xylanase and at least one amyloglucosidase.
• the anti-fouling composition agent comprises one or more gel(s) and at least one endo-1,4-beta-xylanase (E.C. 3.2.1.8) and at least one 1,4-alpha-glucosidase (E.C. 3.2.1.3).
• the present invention provides an aerogel comprising bacteriophages. Bacteriophages are much smaller than the bacteria they destroy—usually between 20 and 200 nm in size.
• Bacteriophages are viruses targeting and preying on bacteria. In this sense they are universally present in low concentrations. They are highly specific and therefore constitute no danger for species outside the family of bacteria for which they are targeted.
• Bacteriophages are not capable of multiplying unless they are prying on the bacteria they target. They are seen as a possible therapy against multi drug resistant strains of many bacteria. As complex proteins they themselves can naturally be attacked and consumed by other organisms.
• the hydrogel network may by a suitable treatment be disintegrated to small fragments the size of micrometers. Still the bacteriophages will be encapsulated in these fragments. These small fragments may be distributed in a paint formulation and be applied to create a coating. During degradation (with antifouling paint it will be polishing rate) of the paint bacteriophages will slowly be released. If a biofilm with the target family of bacteria grows on the surface of the paint the bacteriophages will rapidly attack the bacteria and multiply as long as the family of bacteria is present on the surface.
• Non-limiting examples of lytic bacteriophages suitable for used according to the present invention is ⁇ phage-lysogen, T2 phage, T4 phage, T7 phage.
• hydrogels are a poor choice since they will be polar and incompatible with the organic phase.
• conversion of the hydrogel to an aerogel/cryogel will be required. After this conversion the dried gel can be suspended in the organic phase. This ensures a better distribution in the coating film and a better storage stability.
• the present invention relates to the following aspects:
• the invention does not chemically modify the bacteriophages. Therefore they introduce no new substances to the environment.
• the gelforming substances has been chosen to be based on metal oxides benign to the organisms and the environment.
• TMOS Tetramethyl orthosilicate 98% from Aldrich
• Methanol Methanol reagent PH. EUR. from Bie & Berntsen
• PVA Polyvinyl alcohol, with a degree of polymerisation of 2000 and a degree of hydrolysation of 86-89 mol %, from Fluka Chemika
• PVA Polyvinyl alcohol, with a degree of polymerisation of 2000 and a degree of hydrolysation of 86-89 mol %, from Fluka Chemika
• 100 mL Esperase solution HPF from Novozymes
• 6.279 g dry enzyme was obtained, which was dissolved quickly (about 5 minutes) in the PVA solution and the obtained viscous enzyme solution was added drop wise to 1) during mixing.
• the solution was mixed for additionally 15 minutes.
• antifreeze proteins have recently been described in a patent application disclosed by its owner RUC.
• the antifreeze protein from Rhagium mordax may be taken as an example.
• the protein has been expressed in a microorganism.
• the antifreeze protein is therefore available in a solution similar to the Espherase used in example 1 and 2.
• the procedure for creation of aerogels incorporating antifreeze proteins will therefore substantially be the same as used for Espherase.
• a suspension of Escherichia coli T2 bacteriophages 10 12 pr ml can be used as replacement for the Espherase solutions in the procedures described in example 1 and 2.
• the low temperature and pressure used in the formation of the aerogel is of critical importance for the viability of the bacteriophages during the aerogel formation.
• TMOS Tetramethyl orthosilicate 98% from Aldrich
• Methanol Methanol reagent PH. EUR. from Bie & Berntsen
• TMOS Tetramethyl orthosilicate 98% from Aldrich
• Properase solution Properase 1600 L from Danisco
• Aerogels Including Enzymes, Bacteriophages and/or Other Active Components in a Water-Borne Coating
• This composition contains two binders, where one is degrading (alkyde) and the other is giving hardness (acrylic).
• alkyde dispersion can of course be omitted if another binder is included that can contribute to degradation in sea water and thus to the polishing rate.
• the number of binders can be extended to three or more.
• the binders can be dispersions containing, alkyde or other polyesters, acrylic/acrylic copolymers, polyvinylacetate, urethanes, rosins, water-soluble resins etc.
• the pigment chosen in this case contributes to the polishing rate.
• Other choices of pigments could contain other metals as titanium (rutile and/or anatase), iron, manganese, molybdenum, etc. It is also possible to use organic pigments in the composition. Likewise can other fillers, film formers (coalescing agents), co-solvents, thickeners and other additives be used.
• the aerogel should be regarded as an additive, where the amount normally will be under 5% and in most cases significantly less than 2%. The reason is that the aerogel introduces a different rheological behaviour of the wet product as well as other mechanical properties of the dry coating.
• the dispersion agent is chosen to fit to the pigment in the specific type of paint/coating.
• the aerogel can have an impact on the choice and amount of dispersion agent due to a large surface area.
• the amount of each component is optimised in the specific composition/formulation.
• composition could also be formulated as a matte clear coating to be used either as an anti-fouling coating or as a coating at or above the water line.
• One starting formulation is:
• the binder emulsion and binder emulsion amount is chosen in accordance with the use of the paint. In the same way is the type and amount of pigment and fillers chosen.
• binder emulsions examples include styrene-acrylics, acrylic-copolymers, vinyl acetates, vinyl acetate/ethylene, alkyds, PU-alkyds, polyurethanes etc. Also in this case water-soluble polymers can be included in a formulation. Due to environmental regulations it is expected that cosolvents and coalescing agents will be minimized further.
• One starting formulation is:
• Binder Primal AC-337 (acrylic emulsion) 42.0 Dispersion agent Tego 740 W 0.4 Defoamer Foamex 1488 0.2 Water 35.76 Propylene glycol 5.0 Filler Microdol 1 10.0 Texanol 1.0 Amine 0.2 Thickener RM 825 0.5 Aerogel, with 5% PEG or PVA and/or 0.8 active compound(s) Hostatint oxide red E-OR 4.0 In-can preservation 0.14 Totally 100.0
• a wood stain is basically prepared in the same manner as an architectural paint for walls and ceilings. Very often is an alkyd emulsion used often in combination with an acrylic emulsion. It can also be a hybride binder emulsion, e.g. core-shell technology. Furthermore, the possibility of using water-soluble alkyd resins is available. Alkyd polyurethane emulsions, polyurethane dispersions alone or in combination with acrylic emulsions/water-dilutable polyester resins or self-crosslinking acrylic emulsion among other possibilities can also be mentioned. 2C systems are an option. In this type of composition nano particles may also be present to achieve specific physical properties.
• the difference in the composition from a wood stain is mainly the choice of binder and pigmentation. But the problem is the same with regard to biological growth. Which means that a designed aerogel with enzyme(s) and/or other active compounds may be used in this type of coating with a slow degradation rate. We would expect that the same type aerogel as for wood stain should be used.
• One starting formulation is:
• bacteroiophages can be used against the Listeria monocytogenes bacteria it may also be used against Salmonella , which may be of interest in connection with materials in direct as well as in-direct contact with food.
• the use could include prints on materials as paper, plastic, metal foils etc.
• aerogels can be extended to floor polishes, glues, lacquers, primers, sealers, anti-graffiti products etc.
• aerogels including active compounds can be of interest for coatings used on plastic, concrete and steel.
• the applications can be both for DIY (do-it-yourself) products as well as for industrial applications.
• aerogels including antifreeze protein might extend the use of water-borne products with regard to application. Being able to apply a product at low temperatures and still get film forming is of great interest as well as being able to extend shelf life at low temperatures.
• One starting formulation is:
• a solvent-based wood stain is typically made with an alkyd binder system. It can also be combined with other binders (eg. Polyesters, modified alkyds, rosins and vegetable oils). Binder hybrids and/or copolymers are also a possibility.
• Floor compositions are often solvent-based 2C binder systems.
• Thermoplastic acrylic binders can be used in industrial compositions. Alkyds have in this type of application a short to medium oil length, mainly due to the drying time. Again the binders are often functionalised and can be used with different chemistry and in different combinations. Industrial compositions include products for coil coating and heavy-duty applications.
• Aerogels Including Enzymes, Bacteriophages and/or Other Active Components in Other Coatings
• Aerogels may find use in coatings that are dried in another manner than solvent-based or water-borne coatings. Examples are UV (or EB) drying coatings for floors and furniture. Here degradation might not be the purpose, but basically to achieve an antibacterial effect.
• the drying process can also be a combination of physical drying and radiation.

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• Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Materials Engineering (AREA)
• Epidemiology (AREA)
• Animal Behavior & Ethology (AREA)
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• Public Health (AREA)
• General Health & Medical Sciences (AREA)
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• Proteomics, Peptides & Aminoacids (AREA)
• Bioinformatics & Cheminformatics (AREA)
• Gastroenterology & Hepatology (AREA)
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• 2008
  • 2008-11-12 EP EP08849324.2A patent/EP2215168B1/fr not_active Not-in-force
  • 2008-11-12 US US12/742,464 patent/US20100269731A1/en not_active Abandoned
  • 2008-11-12 KR KR1020107012628A patent/KR20100110294A/ko not_active Application Discontinuation
  • 2008-11-12 WO PCT/DK2008/050272 patent/WO2009062518A1/fr active Application Filing
  • 2008-11-12 DK DK08849906.6T patent/DK2209856T3/da active
  • 2008-11-12 US US12/742,649 patent/US20110056408A1/en not_active Abandoned
  • 2008-11-12 ES ES08849906T patent/ES2749224T3/es active Active
  • 2008-11-12 JP JP2010533437A patent/JP5670736B2/ja not_active Expired - Fee Related
  • 2008-11-12 CN CN2008801245297A patent/CN102137900A/zh active Pending
  • 2008-11-12 EP EP08849906.6A patent/EP2209856B1/fr active Active
  • 2008-11-12 PL PL08849906T patent/PL2209856T3/pl unknown
  • 2008-11-12 PT PT88499066T patent/PT2209856T/pt unknown
  • 2008-11-12 WO PCT/EP2008/065417 patent/WO2009062975A1/fr active Application Filing
  • 2008-11-12 DK DK08849324.2T patent/DK2215168T3/da active
• 2013
  • 2013-02-08 US US13/762,562 patent/US20130273116A1/en not_active Abandoned
• 2014
  • 2014-01-15 US US14/156,313 patent/US9827296B2/en active Active

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