US20070270730A1 - Polyurethane foams for wound management - Google Patents
Polyurethane foams for wound management Download PDFInfo
- Publication number
- US20070270730A1 US20070270730A1 US11/732,575 US73257507A US2007270730A1 US 20070270730 A1 US20070270730 A1 US 20070270730A1 US 73257507 A US73257507 A US 73257507A US 2007270730 A1 US2007270730 A1 US 2007270730A1
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- United States
- Prior art keywords
- polyurethane
- weight
- foams
- range
- component
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
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- 0 CCC(C)*[N+](C)(C)C.CCC(C)C(N)=O Chemical compound CCC(C)*[N+](C)(C)C.CCC(C)C(N)=O 0.000 description 2
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/425—Porous materials, e.g. foams or sponges
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
- A61L15/26—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
Definitions
- Suitable aqueous, anionically hydrophilicized polyurethane dispersions to be used as component (I) in the polyurethane foam forming compositions essential to the present invention comprise the reaction product of:
- the number average particle size of the specific polyurethane dispersions is preferably less than 750 nm and more preferably less than 500 nm. As used herein, the number average particle size is determined by laser correlation spectroscopy.
- the molar ratio of components which contain isocyanate groups to components which contain isocyanate-reactive groups is in the range from 1.05 to 3.5, preferably from 1.2 to 3.0 and more preferably in the range from 1.3 to 2.5, for the preparation of the NCO-functional prepolymers used as component A).
- Suitable polyisocyanates to be used as component A1) include the well-known aromatic, araliphatic, aliphatic and/or cycloaliphatic polyisocyanates which have an NCO functionality of ⁇ 2.
- component A1) comprises 1,6-hexamethylene diisocyanate, isophorone diisocyanate, the isomeric bis(4,4′-isocyanatocyclo-hexyl)methanes or also mixtures thereof.
- polyols such as trimethylolpropane, glycerol, erythritol, pentaerythritol, trimethylolbenzene or trishydroxyethyl isocyanurate.
- component A2) may comprise at least one hydroxyl-containing polycarbonate, preferably at least one polycarbonate diol, which have a number average molecular weight M n in the range from 400 to 8000 g/mol and preferably in the range from 600 to 3000 g/mol.
- hydroxyl-containing polycarbonate preferably at least one polycarbonate diol
- M n number average molecular weight
- the polycarbonate diol preferably contains 40% to 100% by weight of hexanediol, with preference being given to 1,6-hexanediol and/or hexanediol derivatives.
- hexanediol derivatives are based on hexanediol and have ester or ether groups as well as terminal OH groups.
- Such derivatives are obtainable by the reaction of hexanediol with excess caprolactone, or by etherification of hexanediol with itself to form di- or trihexylene glycol.
- Component A4) herein which is also optional, comprises one or more isocyanate-reactive, anionic or potentially anionic and optionally nonionic hydrophilicizing agents.
- the suitable isocyanate-reactive hydrophilicizing agents herein additionally contain one or more of anionic groups, potentially anionic groups and/or nonionic groups.
- Suitable anionically or potentially anionically hydrophilicizing compounds to be used as component A4) are any compounds which have at least one isocyanate-reactive group such as a hydroxyl group and also at least one other type of functionality, i.e. a functionality that is not an isocyanate-reactive group.
- anionic or potentially anionic hydrophilicizing agents for component A4) are those of the aforementioned kind that have carboxylate or carboxyl groups and/or sulfonate groups.
- Examples of these are the monohydroxyl-functional polyalkylene oxide polyether alcohols which contain on average 5 to 70 and preferably 7 to 55 ethylene oxide units per molecule, and are obtainable in a conventional manner by alkoxylation of suitable starter molecules. Such a process is described in, for example, Ullmanns Encyclomann der ischen Chemie, 4th edition, volume 19, Verlag Chemie, Weinheim pages 31-38.
- These compounds are either pure polyethylene oxide ethers or mixed polyalkylene oxide ethers, containing at least 30 mol % and preferably at least 40 mol % of ethylene oxide units, based on all alkylene oxide units present.
- Preferred nonionically hydrophilicizing compounds for component A4) include those of the aforementioned kind that are block (co)polymers prepared by blockwise addition of alkylene oxides onto suitable starters.
- Suitable starter molecules for such nonionic hydrophilicizing agents include saturated monoalcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, sec-butanol, the isomeric pentanols, hexanols, octanols and nonanols, n-decanol, n-dodecanol, n-tetradecanol, n-hexadecanol, n-octadecanol, cyclohexanol, the isomeric methylcyclohexanols or hydroxymethylcyclohexane, 3-ethyl-3-hydroxymethyloxetane or tetrahydrofurfuryl alcohol, diethylene glycol monoalkyl ethers such as, for example diethylene glycol monobutyl ether, unsaturated alcohols such as allyl alcohol, 1,
- component B1) can comprise monofunctional isocyanate-reactive amine compounds, for example, methylamine, ethylamine, propylamine, butylamine, octylamine, laurylamine, stearylamine, isononyloxypropylamine, dimethylamine, diethylamine, dipropylamine, dibutylamine, N-methylaminopropylamine, diethyl(methyl)aminopropylamine, morpholine, piperidine, or suitable substituted derivatives thereof, amide-amines formed from diprimary amines and monocarboxylic acids, monoketimes of diprimary amines, primary/tertiary amines, such as N,N-dimethylaminopropylamine.
- monofunctional isocyanate-reactive amine compounds for example, methylamine, ethylamine, propylamine, butylamine, octylamine, laurylamine, stearylamine,
- Preferred anionic or potentially anionic hydrophilicizing agents for component B2) are those of the aforementioned kind that have carboxylate or carboxyl groups and/or sulfonate groups, such as the salts of N-(2-aminoethyl)- ⁇ -alanine, of 2-(2-aminoethylamino)ethanesulfonic acid or of the addition product of IPDA and acrylic acid (see Example 1 of EP-A 0 916 647).
- Production by the acetone process typically involves the constituents A2) to A4) and the polyisocyanate component A1) being wholly or partly introduced as an initial charge to produce an isocyanate-functional polyurethane prepolymer, and optionally diluted with a water-miscible but isocyanate-inert solvent and heated to temperatures in the range from 50 to 120° C.
- the rate of the isocyanate addition reaction can be increased using the catalysts known in polyurethane chemistry.
- Useful solvents include the customary aliphatic, keto-functional solvents such as acetone, 2-butanone, etc., which can be added not just at the start of the production process but also later, and optionally in portions. Acetone and 2-butanone are preferred.
- the molar ratio of components which contain isocyanate groups to components which contain isocyanate-reactive groups is in the range from 1.05 to 3.5, preferably in the range from 1.2 to 3.0 and more preferably in the range from 1.3 to 2.5.
- the neutralizing step to effect either partial or complete conversion of potentially anionic groups into anionic groups utilizes bases such as tertiary amines such as, for example, trialkylamines having 1 to 12 and preferably 1 to 6 carbon atoms and more preferably 2 to 3 carbon atoms in every alkyl radical or alkali metal bases such as the corresponding hydroxides.
- bases such as tertiary amines such as, for example, trialkylamines having 1 to 12 and preferably 1 to 6 carbon atoms and more preferably 2 to 3 carbon atoms in every alkyl radical or alkali metal bases such as the corresponding hydroxides.
- Chain termination is typically carried out using component B1) one or more amines having an isocyanate-reactive group such as methylamine, ethylamine, propylamine, butylamine, octylamine, laurylamine, stearylamine, isononyloxypropylamine, dimethylamine, diethylamine, dipropylamine, dibutylamine, N-methylaminopropylamine, diethyl(methyl)aminopropylamine, morpholine, piperidine or suitable substituted derivatives thereof, amide-amines formed from diprimary amines and monocarboxylic acids, monoketimes of diprimary amines, primary/tertiary amines, such as N,N-dimethylaminopropylamine.
- an isocyanate-reactive group such as methylamine, ethylamine, propylamine, butylamine, octylamine, laurylamine, stearyl
- the coagulants can be used in solid form or as aqueous solutions or dispersions. It is preferred to use coagulants as aqueous dispersions or solutions.
- auxiliary agents and additive materials to be used as component (III) herein are foam auxiliaries such as foam formers and stabilizers, thickeners or thixotroping agents, antioxidants, light stabilizers, emulsifiers, plasticizers, pigments, fillers and/or flow control agents.
- foam auxiliaries such as foam formers and stabilizers, thickeners or thixotroping agents, antioxidants, light stabilizers, emulsifiers, plasticizers, pigments, fillers and/or flow control agents.
- Such fatty acid derivatives are typically based on fatty acids such as lauric acid, myristic acid, palmitic acid, oleic acid, stearic acid, ricinoleic acid, behenic acid or arachidic acid, coco fatty acid, tallow fatty acid, soya fatty acid and their hydrogenation products.
- fatty acids such as lauric acid, myristic acid, palmitic acid, oleic acid, stearic acid, ricinoleic acid, behenic acid or arachidic acid, coco fatty acid, tallow fatty acid, soya fatty acid and their hydrogenation products.
- thickeners can be used. Suitable thickeners include derivatives of dextrin, of starch or of cellulose such as, for example, cellulose ethers or hydroxyethylcellulose, organic wholly synthetic thickeners based on polyacrylic acids, polyvinylpyrrolidones, polymethacrylic compounds or polyurethanes (associative thickeners) and also inorganic thickeners, such as bentonites or silicas.
- aqueous binders can also be present in the polyurethane foam forming compositions of the present invention.
- aqueous binders can be constructed, for example, of polyester, polyacrylate, polyepoxy or other polyurethane polymers.
- radiation-curable binders such as described in, for example, U.S. Pat. No. 5,684,081, the disclosure of which is hereby incorporated by reference (and which is believed to correspond to EP-A-0 753 531), is also possible.
- Mechanical frothing can be effected using any desired mechanical stirring, mixing and/or dispersing techniques. Air is generally introduced, but nitrogen and other gases can also be used for this purpose.
- Drying is generally effected using conventional heating and drying apparatus, such as (circulating air) drying cabinets, hot air or IR radiators. Drying by leading (or passing) the coated substrate over heated surfaces, for example rolls, is also possible.
- heating and drying apparatus such as (circulating air) drying cabinets, hot air or IR radiators. Drying by leading (or passing) the coated substrate over heated surfaces, for example rolls, is also possible.
- Useful substrates on which the polyurethane foams can be applied include, for example, papers or films which facilitate simple detachment of the wound contact material before it is used to cover an injured site.
- Human or animal tissue such as skin can similarly serve as a substrate, so that direct closure of an injured site is possible by a wound contact material produced in situ.
- the foam densities of the polyurethane foams are typically in the range from 50 to 800 g/liter, preferably in the range from 100 to 500 g/liter and more preferably in the range from 100 to 250 g/liter (mass of all input materials [in g] based on the foam volume of one liter).
- the polyurethane foams After drying, the polyurethane foams have a microporous, at least partial open-cell structure comprising intercommunicating cells.
- the density of the dried foams is typically below 0.4 g/cm 3 , preferably below 0.35 g/cm 3 , more preferably 0.01 to 0.3 g/cm 3 and most preferably in the range from 0.1 to 0.3 g/cm 3 .
- component (I) the polyurethane dispersion and component (II) the coagulant which may each contain any optional components (III) including foam auxiliaries if necessary and/or desired, are separately provided and are then mixed with each other immediately before or during application to the tissue which is to be covered. Frothing here is accomplished by simultaneous decompression of a blowing gas which was present in at least one of the components (I) and/or (II). To consolidate the foam formed, it is subsequently dried. For drying in this embodiment, temperatures of 20 to 40° C. are sufficient. When additional heat sources such as a hair dryer or an IR red light lamp are used, forced thermal drying up to a maximum temperature of 80° C. is also possible.
- additional heat sources such as a hair dryer or an IR red light lamp
- the ready-produced prepolymer was dissolved with 4830 g of acetone and, during the process, cooled down to 50° C., and subsequently admixed with a solution of 25.1 g of ethylenediamine, 116.5 g of isophoronediamine, 61.7 g of diaminosulfonate and 1030 g of water metered in over 10 minutes. The mixture was subsequently stirred for 10 minutes. Then, a dispersion was formed by addition of 1250 g of water. This was followed by removal of the solvent by distillation under reduced pressure.
- the white dispersion obtained had the following properties: Solids content: 61% Particle size (LKS): 312 nm Viscosity (viscometer, 23° C.): 241 mPas pH (23° C.): 6.02
- the white dispersion obtained had the following properties: Solids content: 59% Particle size (LKS): 350 nm Viscosity (viscometer, 23° C.): 126 mPas pH (23° C.): 7.07
- the polyurethane dispersions produced as described in Examples 1-6 were mixed with the foam auxiliaries as set forth in the amounts indicated in Table 1 and frothed by means of a commercially available hand stirrer (stirrer made of bent wire) to a I liter foam volume. While stirring was continued, the foams obtained were finally coagulated by addition of Coagulant 1 in the amount set forth in Table 1; coagulation left foam volume unchanged (slight increase in viscosity). Thereafter, the foams were drawn down on silicone-coated paper by means of a blade coater set to the gap height reported in Table 1. Table 1 similarly recites the drying conditions for the foams produced as indicated. Clean white foams having good mechanical properties and a fine porous structure were obtained without exception.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Materials Engineering (AREA)
- Hematology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dermatology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Polyurethanes Or Polyureas (AREA)
- Materials For Medical Uses (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Medicinal Preparation (AREA)
- Prostheses (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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US13/448,576 US8629195B2 (en) | 2006-04-08 | 2012-04-17 | Production of polyurethane foams |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102006016636.1 | 2006-04-08 | ||
DE102006016636A DE102006016636A1 (de) | 2006-04-08 | 2006-04-08 | Polyurethan-Schäume für die Wundbehandlung |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/245,264 Continuation US20090099082A1 (en) | 2006-04-08 | 2008-10-03 | Production of polyurethane foams |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/448,576 Continuation-In-Part US8629195B2 (en) | 2006-04-08 | 2012-04-17 | Production of polyurethane foams |
Publications (1)
Publication Number | Publication Date |
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US20070270730A1 true US20070270730A1 (en) | 2007-11-22 |
Family
ID=38457916
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/732,575 Abandoned US20070270730A1 (en) | 2006-04-08 | 2007-04-04 | Polyurethane foams for wound management |
US12/296,380 Expired - Fee Related US8197835B2 (en) | 2006-04-08 | 2007-04-05 | Biomedical foam articles |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/296,380 Expired - Fee Related US8197835B2 (en) | 2006-04-08 | 2007-04-05 | Biomedical foam articles |
Country Status (17)
Cited By (33)
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US20080070999A1 (en) * | 2006-09-16 | 2008-03-20 | Bayer Materialscience Ag | Alkylpolyglycosides useful as stabilizers for pur foams |
US20090054542A1 (en) * | 2007-08-23 | 2009-02-26 | Bayer Materialscience Ag | Eo/po block copolymers useful as stabilizers for pur foams |
US20090092647A1 (en) * | 2007-10-05 | 2009-04-09 | Bayer Materialscience Ag | Polyurethane foams for wound management |
US20090099082A1 (en) * | 2007-10-05 | 2009-04-16 | Bayer Materialscience Ag | Production of polyurethane foams |
US20090148501A1 (en) * | 2007-10-19 | 2009-06-11 | Bayer Materialscience Ag | Process for the preparation of aromatized chewing foams for cosmetic products |
US20090263431A1 (en) * | 2007-10-05 | 2009-10-22 | Bayer Innovation Gmbh | Polyurethane foams for wound management |
US20100030171A1 (en) * | 2008-08-01 | 2010-02-04 | Canada T Andrew | Composite article suitable for use as a wound dressing |
US20110038808A1 (en) * | 2006-10-25 | 2011-02-17 | Bayer Materialscience Ag | Flavored chewable foams and a process for their production |
US20110110996A1 (en) * | 2008-07-04 | 2011-05-12 | Bayer Materialscience Ag | Layer composite, suitable as a wound dressing, comprising a polyurethane foam layer, an absorber layer and a cover layer |
US20110160633A1 (en) * | 2008-08-27 | 2011-06-30 | Bayer Materialscience Ag | Method for producing shaped polyurethane foam wound dressings |
US20110171277A1 (en) * | 2008-09-19 | 2011-07-14 | Bayer Materialscience Ag | Wound dressing having a polyurethane foam layer and a cover layer made of thermoplastic polymer |
US20110201715A1 (en) * | 2008-08-27 | 2011-08-18 | Bayer Materialscience Ag | Method For Producing Shaped Polyurethane Foam Wound Dressings |
US20110262504A1 (en) * | 2010-04-21 | 2011-10-27 | Geert Andre Deleersnyder | Liquid cleaning and/or cleansing composition |
US20110275728A1 (en) * | 2009-01-24 | 2011-11-10 | Bayer Materialscience Ag | Dispersed two-component polyurethane foams |
US20110294911A1 (en) * | 2009-01-24 | 2011-12-01 | Bayer Materialscience Ag | Polyurethane surfactant stabilized polyurethane foams |
US8440602B2 (en) | 2009-12-22 | 2013-05-14 | The Procter & Gamble Company | Liquid cleaning and/or cleansing composition comprising a divinyl benzene cross-linked styrene polymer |
US8440603B2 (en) | 2011-06-20 | 2013-05-14 | The Procter & Gamble Company | Liquid cleaning and/or cleansing composition comprising a polylactic acid biodegradable abrasive |
US8440604B2 (en) | 2008-09-30 | 2013-05-14 | The Procter & Gamble Company | Liquid hard surface cleaning composition |
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US8470759B2 (en) | 2011-06-20 | 2013-06-25 | The Procter & Gamble Company | Liquid cleaning and/or cleansing composition comprising a polyhydroxy-alkanoate biodegradable abrasive |
US8546316B2 (en) | 2010-09-21 | 2013-10-01 | The Procter & Gamble Company | Liquid detergent composition with natural abrasive particles |
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US8629195B2 (en) | 2006-04-08 | 2014-01-14 | Bayer Materialscience Ag | Production of polyurethane foams |
US8629095B2 (en) | 2010-04-21 | 2014-01-14 | The Procter & Gamble Company | Liquid cleaning and/or cleansing composition comprising polyurethane foam abrasive particles |
US8680036B2 (en) | 2009-12-22 | 2014-03-25 | The Procter & Gamble Company | Liquid cleaning composition comprising color-stable polyurethane abrasive particles |
US8759270B2 (en) | 2011-06-20 | 2014-06-24 | The Procter & Gamble Company | Liquid detergent composition with abrasive particles |
US8852643B2 (en) | 2011-06-20 | 2014-10-07 | The Procter & Gamble Company | Liquid cleaning and/or cleansing composition |
US9163201B2 (en) | 2012-10-15 | 2015-10-20 | The Procter & Gamble Company | Liquid detergent composition with abrasive particles |
US9353337B2 (en) | 2010-09-21 | 2016-05-31 | The Procter & Gamble Company | Liquid cleaning composition |
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- 2007-04-05 JP JP2009503489A patent/JP2009533335A/ja active Pending
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