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WO2007136176A1 - Pansement à base de mousse de polyuréthanne comportant une couche médicamenteuse et son procédé de fabrication - Google Patents

Pansement à base de mousse de polyuréthanne comportant une couche médicamenteuse et son procédé de fabrication Download PDF

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Publication number
WO2007136176A1
WO2007136176A1 PCT/KR2007/002078 KR2007002078W WO2007136176A1 WO 2007136176 A1 WO2007136176 A1 WO 2007136176A1 KR 2007002078 W KR2007002078 W KR 2007002078W WO 2007136176 A1 WO2007136176 A1 WO 2007136176A1
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WO
WIPO (PCT)
Prior art keywords
drug
polyurethane
layer
weight
parts
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.)
Ceased
Application number
PCT/KR2007/002078
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English (en)
Inventor
Won Il Kim
Jeong Yeol Kang
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WONBIOGEN CO Ltd
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WONBIOGEN CO Ltd
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Publication of WO2007136176A1 publication Critical patent/WO2007136176A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
    • B32B5/18—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by features of a layer of foamed material
    • 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
    • A61L15/07—Stiffening bandages
    • A61L15/10—Stiffening bandages containing organic materials
    • 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
    • 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
    • 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
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A61L15/44—Medicaments
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B27/065—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of foam
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/40—Layered products comprising a layer of synthetic resin comprising polyurethanes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
    • B32B5/18—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by features of a layer of foamed material
    • B32B5/20—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by features of a layer of foamed material foamed in situ
    • 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
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
    • A61L2300/23—Carbohydrates
    • 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
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
    • A61L2300/30—Compounds of undetermined constitution extracted from natural sources, e.g. Aloe Vera
    • 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
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
    • A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
    • 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
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/60—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
    • A61L2300/606—Coatings
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2266/00—Composition of foam
    • B32B2266/02—Organic
    • B32B2266/0214—Materials belonging to B32B27/00
    • B32B2266/0278—Polyurethane
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2535/00—Medical equipment, e.g. bandage, prostheses or catheter

Definitions

  • the present invention relates to a polyurethane form dressing and a method for manufacturing the same. More specifically, the present invention relates to a polyurethane foam dressing comprising a drug-containing layer and a method for manufacturing the same.
  • OpSiteTM was introduced as a semipermeable transparent thin film in the early 1970s which keeps the wounded area wet, and facilitates lysis of necrotic tissues and formation of granulation tissues, thereby accelerating wound healing.
  • OpSite involvescongestion of excessive exudates in the wounded area, and causes festering of the skin around the wound, thus allowing the exudates to flow out. For this reason, OpSite has a disadvantage, e.g., inconvenience associated with intentional release of exudates from the wound.
  • DuoDERM was introduced as a hydrocolloidal dressing in 1982.
  • DuoDERMTM is attached to a wounded area, it reacts with exudates secreted from the wound, thus imparting a wet environment as a gel state and promoting epithelialisation of the wound.
  • DuoDERMTM is impermeable to a gas such as oxygen or carbon dioxide, or water vapor, thus disadvantageously involving congestion of excessive exudates and rendering the gel to remain on the wound after replacement.
  • Korean Patent No. 0404140 discloses a method for preparing a polyurethane foam dressing which comprises mixing/stirring a polyurethane prepolymer having an isocyanate-terminal, a crossliking agent, a foaming agent, an antibacterial agent and other additives, and injecting the mixture in a mold, followed by foaming.
  • a method for manufacturing a polyurethane foam dressing comprising:
  • FIGs. 1 to 6 are a schematic view illustrating a polyurethane foam dressing according to the present invention.
  • FIGs. 7 to 9 are a scanning electron micrograph (SEM) of a polyurethane foam dressing according to the present invention.
  • FIG. 10 is a graph showing a drug release behavior of each sample in accordance with variation in an antibacterial agent concentration and a production method.
  • the present invention is directed to a method for manufacturing a polyurethane foam dressing, the method comprising: forming a nonporous waterproof polyurethane film layer, forming a tacky gel-like polyurethane foam layer; laminating the polyurethane foam layer on the polyurethane film layer; and forming a drug- containing layer.
  • a method for manufacturing a polyurethane foam dressing comprising: forming a nonporous waterproof polyurethane film layer, forming a tacky gel-like polyurethane foam layer; laminating the polyurethane foam layer on the polyurethane film layer; and forming a drug- containing layer.
  • the polyurethane resin used herein is a hydrophilic polyurethane resin into which at lease one hydrophilic group is introduced.
  • a polyurethane film layer with waterproofing as well as moisture permeability is produced.
  • the polyurethane film layer constitutes the outside of a dressing produced according to the present invention.
  • the term a "moisture permeable/waterproof film” or “moisture permeable waterproof film” used herein refers to a polyurethane film with both moisture permeability and waterproofing which is produced with polyurethane having at least one hydrophilic group.
  • the pigment there may be preferably used an organic or inorganic pigment well- known in the art which consists of a polyurethane resin as a vehicle, and methyl ethyl ketone and dimethylformamide as a solvent. Preferred is the use of an organic pigment.
  • isocyanate is added to a mixture of polyol and diol, followed by reacting each other, to prepare a polyurethane prepolymer.
  • the polyol may be selected from polypropylene oxide glycol, polyethylene oxide glycol, polytetramethylene ether glycol, ethylene oxide/propylene oxide copolymer, polytetrahydrofuran/ethylene oxide copolymer, polytetrahydrofuran/propylene oxide copolymer, polybutylene carbonate glycol, polyhexamethylene carbonate glycol, poly- caprolactone glycol, polyethylene adipate, polybutylene adipate, polyneopentyl adipate and polyhexamethylene adipate. These polyols may be used alone or in combination thereof.
  • Preferred is the use of a mixture of polyethylene oxide glycol and polypropylene oxide glycol, each having at least two hydroxyl groups and a molecular weight of 500 to 6,000 in a molar ratio of 4 : 6 to 8 : 2, or an ethylene oxide/propylene oxide copolymer in which the content of ethylene oxide is 20 to 90%.
  • the isocyanate may be selected from aromatic isocyanates, aliphatic isocyanates, substituted isocyanates and mixtures thereof. Specific examples of the isocyanate include 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, methylene diphenyl di- isocyanate, 1,5-naphtalene diisocyanate, tolidine diisocyanate, hexamethylene- 1,6-diisocyanate, isoporone diisocyanate, xylene diisocyanate, cyclohexylene- 1,4-diisocyanate, lysine diisocyanate and tetramethylene-xylene diisocyanate.
  • polystyrene resin may be used alone or in combination thereof.
  • Preferred is the use of isoporone diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate and methylene diphenyl isocyanate.
  • the diol may be selected from ethylene glycol, propylene glycol, 1,3-butanediol,
  • 1,4-butanediol 1,5-pentanediol, 1,6-hexanediol
  • Methylene glycol diethylene glycol, tetraethylene glycol, dipropylene glycol, dibutylene glycol, neopentyl glycol, 1,4-cyclohexane dimethanol and 2-methyl-l,3-pentanediol.
  • diols may be used alone or in combination thereof.
  • Preferred is the use of ethylene glycol, propylene glycol, 1,4-butanediol or a combination thereof.
  • an antioxidant well-known in the art may be added to a polyurethane prepolymer using a conventional method.
  • suitable antioxidants include phenyl-beta-naphtalamine, cysteine hydrochloride, dibutylhydroxytoluene, nordihy- droguaiaretic acid, butylhydroxyanisole, phosphoric acid, citric acid, ascorbic acid, erythorbic acid, propyl gallate, and products available from Ciba Specialty Chemicals Corp., such as IRGANOX 1010TM, IRGANOX 1035TM, IRGANOX 1076TM, IRGANOX 1330TM, IRGANOX 1425WLTM, IRGANOX 3114TM, IRGANOX B215TM, IRGANOX B220TM, IRGANOX B225TM, IRGANOX B561TM, IRGANOX B313TM, IRGANOX B501WTM
  • the antioxidant may be preferably added in an amount of 0.05% to 5% by weight, based on the total weight of the polyurethane prepolymer.
  • DIW deionized water
  • surfactant a surfactant
  • any surfactant well-known in the art may be used in accordance with a conventional use and method.
  • suitable surfactants include: ethylene oxide/propylene oxide block copolymers available from BASF Corp., such as F-68 , F-87TM, F-88TM, F- 108TM and F- 127TM; silicon-based surfactants available from BASF Corp., such as L-580TM, L-603TM, L-688TM, L-5420TM, SZ- 1703TM, L-6900TM, L-3150TM, Y-7931TM, L- 1580TM, L-5340TM, L-5333TM, L-6701TM, L-5740MTM, L-3002TM and L- 626 ; and surfactants available from Dow chemicals Corp., such as DOWFAX 63N10 TM, DOWFAX 63N30TM, DOWFAX 81N13TBTM, DOWFAX DF- 111TM, DOWFAX DF- 117TM
  • the foaming mixture may comprise a moisturizer, e.g., glycerin.
  • a moisturizer e.g., glycerin.
  • Any moisturizer may be used without particular limitation so long as it is applicable to human body and exists as a liquid phase.
  • a liquefied moisturizer prepared by dissolving an aqueous natural polymer in distilled water may be used.
  • Preferred is the use of glycerin only in view of a preparation process.
  • the foaming mixture may further comprise a well-known super absorbent polymer as an auxiliary absorber to improve the absorbability of polyurethane foams.
  • the foaming mixture is applied to a release sheet to a thickness of 0.05 to 10 D to produce an uncured polyurethane foam layer as a tacky gel.
  • the foaming mixture stirred at a high speed in the previous step is applied to a uniform thickness on a release sheet using a coating gauge. After 1 to 2 minutes, a polyurethane foam layer in a tacky gel-state is obtained. In this step, a polyurethane foam layer is produced in a gel-like tacky state in which the applied foaming mixture is uncured, immediately followed by a subsequent process.
  • release sheet there is no particular limitation. Preferred is the use of a silicon-treated release sheet.
  • the polyurethane film layer and the polyurethane foam layer thus produced in the previous step are laminated, followed by drying using a hot air drier.
  • the resulting laminate is allowed cool to room temperature.
  • the release sheets in contact with the polyurethane film layer and the polyurethane foam layer are sequentially peeled off to obtain a polyurethane foam dressing.
  • the uncured gel- like tacky polyurethane foam layer and the polyurethane film layer are laminated, followed by drying using a hot air drier at about 100 0 C for one minute.
  • the lamination can be carried out in a simple manner without using any adhesive agent.
  • the polyurethane foam layer and the waterproof polyurethane film layer cannot be laminated for a tack- free time at which polyurethane foams lose gel properties and tack.
  • a polyurethane prepolymer is mixed with a foaming mixture with stirring at a high speed of about 3,000 RPM. The mixture is applied to a uniform thickness on a silicon-treated release sheet.
  • the polyurethane foam layer and the waterproof polyurethane film layer are laminated such that release sheet- free sides of the two layers face each other. Then, the laminate is dried in a hot air drier at about 100 0 C for one minute. After completion of the drying, the release sheet in contact with the polyurethane film layer is peeled off. The resulting layer is aged in a hot air drier at about 7O 0 C for a predetermined time. The release sheet in contact with the foam layer is peeled off to produce a laminated polyurethane foam dressing.
  • the reason for removal of the release sheet of the waterproof polyurethane film layer after the drying in a hot air drier is that in a case where a polyurethane film layer is aged in a hot air drier at about 7O 0 C without hot-air drying, a polyurethane foam dressing is shrunken and curled, thus making it difficult to wind the dressing in a roll shape and inhibiting evaporation of the remaining moisture from the foam layer. Insufficient moisture evaporation causes a deterioration in the absorbability and absorption speed for wound exudates of the wound contact layer 11 of the polyurethane foam dressing. After the aging for a predetermined time, the polyurethane foam dressing is shrunken to some extent.
  • the waterproof film layer is also shrunken to create natural wrinkles.
  • a wrinkle-pattern release sheet e.g., AS- 175 available from Asahi roll Co., Ltd.
  • AS- 175 available from Asahi roll Co., Ltd.
  • a drug-containing solution with a viscosity of 2,000 to 4,000 cps/25°C is applied to the foam layer of the laminated polyurethane dressing, to form a drug-containing layer.
  • the drug-containing solution is prepared by dissolving or dispersing a drug in a solvent e.g., deionized water (DIW) and adding a pharmaceutically acceptableexcipient or viscosity control agent thereto to adjust the viscosity of the solution to 2,000 to 4,000 cps/25°C.
  • DIW deionized water
  • drug of thedrug-containing solution used in the present invention refers to all substances for directly or indirectly contributing to wound healing (e.g., moisturizers or wound-healing adjuvants) as well as substances (e.g., antimicrobial agents) conventionally known in the art as medicines.
  • the drug may include an antimicrobial agent well-known in the art to prevent infection and growth of various germs.
  • suitable antimicrobial agents include silver sulfadiazine, povidone iodine, iodine, iodide ionic salts, fradiomycin sulfate, acrinol, chlorohexidine, benzalkonium chloride, benzethonium chloride and sodium fusidate.
  • Another well-known drug may be incorporated in the dressing of the present invention for treatment and prevention of the wound.
  • a moisturizer or wound-healing adjuvant may be incorporated singly, or together with another drug e.g., antimicrobial agent.
  • the moisturizer and wound-healing adjuvant impart a wet environment to a wound, prevent formation of a scab over the wound, enables favorable healing of the wound, and prevent precipitation of a drug (e.g., an antimicrobial agent) in the solution via uniform dispersion of the drug which results from enhancement in the viscosity of the solution.
  • a drug e.g., an antimicrobial agent
  • the moisturizer and wound-healing adjuvant enhance the viscosity of the solution, thus preventing the drug-containing solution from permeating into the polyurethane foam layer.
  • moisturizer and wound-healing adjuvant examples include propylene glycol alginate, methyl cellulose, sodium carboxymethyl cellulose, calcium carboxymethyl cellulose, sodium carboxymethyl starch, vaseline, sodiumalginate, ammonium alginate, potassium alginate, calcium alginate, sodium caseinate, guar gum, locust bean gum, xanthan gum, cyclodextrin, gum arabic, gellan gum, carrageenan, karaya gum, casein, tara gum, tamarind gum, tragacanth gum, pectin, glucomannan, gum ghatti, ara- binogalactan, furcelleran, pullulan, glucosamine, carboxymethyl cellulose, chitin, chitosan, hyaluronic acid, amino acid, L-asparaginic acid, L-sodium aspartate, DL- alanine, L-isoleucine, lysine hydrochloride,
  • Sugar for showing bacteriostasis and granulation growth activities may be added as a wound-healing adjuvant.
  • specific examples of the sugar include sucrose, sorbitol, mannitol, fructose, dextrose,xylitol, lactose, maltose, maltitol and trehalose.
  • a natural material capable of exhibiting antiinflammatory, antibacterial and antifungal actions, and skin regeneration effect.
  • the natural material include teatree oil, Sophora angustifolia extract, iris extract, Glycyrrhiza glabra extract, bioflavonoids derived from grapefruit seeds, naringin, polypeptides, tocopherols, asiatic acid derived from Centella asiatica, madecasic acid, ⁇ -glucan extracted from mushrooms, Neem extract, witch hazel extract, allantoin, Portulace oleracea extract, Ponciri fructus extract, phytosphingosine, aloe extract and a combination thereof.
  • the solvent used herein may be a pharmaceutically acceptable solvent. Any solvent may be used without particular limitation so long as it is pharmaceutically acceptable, and dissolves or disperse a target drug.
  • suitable solvents include, but are not particularly limited to deionized water (DIW), ethanol and methanol. Preferred is the use of deionized water.
  • any excipient well-known in the pharmaceutical industry may be used herein without limitation.
  • glycerin may be used.
  • Any viscosity control agent may be used without particular limitation so long as it is pharmaceutically acceptable.
  • carboxymethyl cellulose sodiumalginate and carrageenan.
  • the drug may be used singly or in combination thereof in a predetermined dosage.
  • the drug may be added in an amount of 2 to 50 parts by weight, based on 100 parts by weight of a solvent, e.g., deionized water (DIW).
  • a solvent e.g., deionized water (DIW).
  • the drug e.g., a moisturizer and wound-healing adjuvant
  • another drug e.g., an antimicrobial agent
  • the viscosity of the drug-containing solution can be adjusted to 2,000 to 4,000 cps/25°C without using any excipient or viscosity control agent.
  • the viscosity of the drug-containing solution is 2,000 cps/°C or less, the drug- containing solution may be dis advantageously permeated into the polyurethane foam dressing.
  • the viscosity is 4,000 cps/25°C or higher, there may be a difficulty in applying the drug-containing layer to the surface of the polyurethane foam dressing.
  • the application may be carried out using a method such as knife-over-roll coating or release sheet mold processing.
  • a method such as knife-over-roll coating or release sheet mold processing.
  • knife-over-roll coating is used.
  • the drug-containing solution is applied to a roll whose surface has a negative of a uniform pattern (e.g., circle or line), followed by drawing with a knife, allowing the solution to be in contact with the surface of the polyurethane foam dressing.
  • a uniform pattern e.g., circle or line
  • the dressing is dried in a hot air drier at 100 0 C for 30 sec to produce a drug-containing layer.
  • the viscosity of the solution suitable for application ranges from 2,000 to 4,000 cps/25°C.
  • the solution has a low viscosity of 2,000 cps/25°C or less, there is a risk that the solution is insufficiently adhered to the negative of the roll.
  • the viscosity is 4,000 cps/25°C or higher, there may be a difficulty in transcribing the drug-containing layer to the surface of the polyurethane foam dressing.
  • the formation of the drug-containing layer may be carried out by applying the solution to a uniform pattern-embossed release sheet or a perforated release sheet to a desired thickness using a coating gauge, laminating a polyurethane foam dressing on the sheet and drying the laminate in a hot air drier. Taking process conditions or the state of products into the consideration, those skilled in the art process will be able to select a suitable method.
  • the drug-containing layer 30 may have various shapes via the mentioned methods.
  • FIGs. 4 to 6 show various shapes of a drug-containing layer 30.
  • FIG. 4 shows the surface of a polyurethane foam dressing to which the drug-containing layer 30 is applied in circle patterns.
  • FIG. 5 shows the surface of a polyurethane foam dressing to which the drug-containing layer 30 is applied in a region except for the circle patterns.
  • FIG. 6 shows the surface of a polyurethane foam dressing to which the drug-containing layer 30 is applied in a continuous lattice pattern.
  • the shapes of the drug-containing layer 30 according to the present invention shown in FIGs. 4 to 6 are given for illustrative purposes. Accordingly, the drug-containing layer 30 may have a variety of shapes such as a simple linear shape, e.g., straight, perpendicular, inclined, or curved line.
  • the area of the drug-containing layer is preferably 30 to 90% with respect to the total area of the foam layer.
  • the area of the drug-containing layer is 30% or less, the drug cannot be evenly delivered to the wound.
  • the area of the drug- containing layer is 90% or higher, exudate absorption is slow due to an excessive area of the drug-containing layer.
  • the polyurethane foam dressing having the drug-containing layer produced according to the present invention includes: an outer film layer composed of a nonporous waterproof polyurethane film; a foam layer arranged on the outer film layer, the foam layer composed of polyurethane foams; and a drug-containing layer arranged on the foam layer wherein the drug of the drug-containing layer is immiscible with polyurethane constituting the foam layer.
  • FIG. 1 is a cross-sectional view illustrating schematically a polyurethane foam dressing according to the present invention.
  • the polyurethane foam includes an outer film layer 20 composed of a nonporous waterproof polyurethane film; a foam layer 10 composed of expandedpolyurethane foams; and a drug-containing layer 30 in this order.
  • the outer film layer 20 is composed of a moisture permeable/waterproof polyurethane film and constitutes an outermost side of the dressing, i.e. an outermost layer on the opposite side of the surface in contact with skin.
  • the outer film layer 20 has a high moisture permeability of 400 to 3,000 g/D/day (relative humidity: 10 to 90%, 37 0 C, Desiccant Method), prevents infection of bacteria and microbe from the outside, prevents escape of exudates, and imparts a moisture environment to the wound.
  • the polyurethane foam layer 10 is composed of expanded polyurethane foams which are formed by subjecting expansion molding to polyurethane on a sheet.
  • the polyurethane foam layer 10 has a bilayer structure including: a wound contact layer 11, in which a plurality of open cells with a diameter of 1 to 50 D are formed; and an inner absorption layer 12, in which a plurality of open cells with a diameter of 1 to 600 D are formed.
  • the bilayer structure is naturally formed during the production process.
  • FIG. 2 is a schematic view illustrating the surface of the wound contact layer 11.
  • FIG. 3 is a schematic view illustrating the surface of the inner absorption layer 12.
  • the wound contact layer 11 has open cells with a diameter of 1 to 50 D, absorbs exudates and does not adhere to the wound.
  • the inner absorption layer 12 has a plurality of open cells with a diameter of 1 to 600 D, exhibits exudate absorbability of 100 to 1,000 wt%, based on the weight thereof and has a density range of 0.1 to 0.5 g/D.
  • the drug-containing layer 30 is formed on the foam layer and contains a drug immiscible with polyurethane constituting the foam layer.
  • the drug-containing layer 30 takes up 30 to 90% of the total area of the foam layer and has a thickness range of 10 D to 1 D. As shown in FIGs. 4 to 6, the drug-containing layer 30 may have a variety of shapes.
  • FIGs. 7 to 9 are a scanning electron micrograph (SEM) of the polyurethane foam dressing according to the present invention.
  • FIG. 7 is a scanning electron micrograph (SEM) of the wound contact layer 11.
  • FIG. 8 is a scanning electron micrograph (SEM) of the inner absorption layer 12.
  • FIG. 9 is a scanning electron micrograph (SEM) of the outer film layer 20. It can be confirmed from FIGs. 7 and 8 that the inner absorption layer 12 has a great deal of large-size open cells, as compared to the wound contact layer 11.
  • the outer film layer 20 is non-porous, allowing waterproofing.
  • the polyurethane mixture solution was applied to a predetermined thickness on a matt release sheet (available from Youlchon Chemical Co., Ltd.) using a thickness gauge.
  • the sheet was dried in a hot air drier at 100 0 C for 30 minutes to form a moisture permeable waterproof polyurethane film on one surface of the release sheet.
  • the thickness of the moisture-permeable waterproof polyurethane film thus formed was 30 D.
  • Example 1 were added 80 parts by weight of deionized water (DIW), 20 parts by weight of glycerin as a moisturizer and 2 parts by weight of a surfactant (F-68 available from BASF Corp.). After stirring at a rate of 3,000 RPM for 10 sec, the mixture was applied to a silicon release sheet (available from Youlchon Chemical Co., Ltd.), rendering the sheet to be coated with the mixture using a 2.2 mm thickness gauge.
  • DIW deionized water
  • F-68 available from BASF Corp.
  • Example of a moisture permeable waterproof polyurethane film was laminated on the coating such that a gap between the film and the coating was adjusted to 2.2 mm, immediately followed by drying in ahot air drier at 100 0 C for one minute.
  • a polyurethane foam dressing was produced using knife-over-roll coating such that it includes a drug- containing layer taking up 30% of the total area of the foam layer and having a thickness of 0.2 mm, as shown in FIG. 1.
  • the mechanical properties were measured using a universal test machine (Instron) under conditions of 50 N load cell, 20 mm gauge width, 30 D gauge length, and 100 D/min cross head speed.
  • a sample with a size of 5 cm x 5 cm was prepared from the dressing. After the sample was stood at room temperature for 24 hours, an initial weight A of the sample was measured. After dipping in distilled water at 37 0 C for 24 hours, the sample was drawn off and subjected to removal of moisture present on the surface thereof. Then, a final weight B of the sample was measured. The water absorption was calculated from the following equation:
  • thermohydrostat in accordance with ASTM E96-94 (desiccant method).
  • the temperature of the thermohydrostat was 37 0 C and the relative humidity was 80%.
  • a 6 to 8 week-old rat (weight: 250 to 300 g) was targeted for the test.
  • the rat was intraperitoneally anesthetized with nenbutal.
  • the rat was allowed spontaneous respiration without additional endotracheal intubation or oxygen supply.
  • the dorsal part of the rat was sheared and completely subjected to hair removal with a razor.
  • the target site was sterilized with povidone and alcohol, and surgically operated under sterile environment. A skin defect of 80 ⁇ D was made on the dorsal part.
  • the wound site was washed with a physiological saline solution and subjected to moisture removal using a dry gauze.
  • a dressing was attached to the wound site such that the size of the dressing was about 1 D larger than that of the wound site.
  • the dressing was covered with two gauzes, and was slightly fitted on the rat body using an elastic bandage to prevent the dressing from being detached.
  • dressing exchange was performed at an interval of 3 days which ranges from 3 days to 15 days. Epithelium growth of the skin defect site, detachment of granulation tissue upon dressing exchange and wound healing effects were measured via biopsy using an optical microscope with the passage of time.
  • Example 1 were added 80 parts by weight of deionized water (DIW), 20 parts by weight of glycerin as a moisturizer and 2 parts by weight of a surfactant (F-68 available from BASF Corp.). After stirring at a rate of 3,000 RPM for 10 sec, the mixture was applied to a silicon release sheet (available from Youlchon Chemical Co., Ltd.), rendering the sheet to be coated with the mixture using a 2.2 D thickness gauge.
  • DIW deionized water
  • F-68 available from BASF Corp.
  • Example of a moisture-permeable waterproof polyurethane film was laminated on the coating such that a gap between the film and the coating was adjusted to 2.2 D, immediately followed by drying in ahot air drier at 100 0 C for one minute.
  • a polyurethane foam dressing was produced using knife-over-roll coating such that it includes a drug- containing layer taking up 50% of the total area of the foam layer having a thickness of 0.2 D, as shown in FIG. 1.
  • Example 1 were added 80 parts by weight of deionized water (DIW), 20 parts by weight of glycerin as a moisturizer and 2 parts by weight of a surfactant (F-68 available from BASF Corp.). After stirring at a rate of 3,000 RPM for 10 sec, the mixture was applied to a silicon release sheet (available from Youlchon Chemical Co., Ltd.), rendering the sheet to be coated with the mixture using a 2.2 D thickness gauge.
  • DIW deionized water
  • F-68 available from BASF Corp.
  • Example of a moisture-permeable waterproof polyurethane film was laminated on the coating such that a gap between the film and the coating was adjusted to 2.2 D, immediately followed by drying in ahot air drier at 100 0 C for one minute.
  • a polyurethane foam dressing was produced using knife-over-roll coating such that it includes a drug- containing layer taking up 80% of the total area of the foam layer having a thickness of 0.2 D, as shown in FIG. 1.
  • Example 1 were added 80 parts by weight of deionized water (DIW), 20 parts by weight of glycerin as a moisturizer and 2 parts by weight of a surfactant (F-68TM available from BASF Corp.). After stirring at a rate of 3,000 RPM for 10 sec, the mixture was applied to a silicon release sheet (available from Youlchon Chemical Co., Ltd.), rendering the sheet to be coated with the mixture using a 2.2 mm thickness gauge.
  • DIW deionized water
  • F-68TM available from BASF Corp.
  • Example of a moisture-permeable waterproof polyurethane film was laminated on the coating such that a gap between the film and the coating was adjusted to 2.2 D, immediately followed by drying in ahot air drier at 100 0 C for one minute.
  • a polyurethane foam dressing was produced using knife-over-roll coating such that it includes a drug- containing layer taking up 90% of the total area of the foam layer and having a thickness of 0.2 D, as shown in FIG. 1.
  • Example 1 were added 80 parts by weight of deionized water (DIW), 20 parts by weight of glycerin as a moisturizer, 2 parts by weight of a surfactant (F-68 available from BASF Corp.), 3 parts by weight of sodium fusidate and 3 parts by weight of Centella asiatica extract. After stirring at a rate of 3,000 RPM for 10 sec, the mixture was applied to a silicon release sheet (available from Youlchon Chemical Co., Ltd.), rendering the sheet to be coated with the mixture using a 2.2 mm thickness gauge.
  • Example of a moisture-permeable waterproof polyurethane film was laminated on the coating such that a gap between the film and the coating was adjusted to 2.2 D, immediately followed by drying in ahot air drier at 100 0 C for one minute.
  • Example 1 were added 80 parts by weight of deionized water (DIW), 20 parts by weight of glycerin as a moisturizer and 2 parts by weight of a surfactant (F-68 available from BASF Corp.). After stirring at a rate of 3,000 RPM for 10 sec, the mixture was applied to a silicon release sheet (available from Youlchon Chemical Co., Ltd.), rendering the sheet to be coated with the mixture using a 2.2 D thickness gauge.
  • DIW deionized water
  • F-68 available from BASF Corp.
  • Example of a moisture-permeable waterproof polyurethane film was laminated on the coating such that a gap between the film and the coating was adjusted to 2.2 D, immediately followed by drying in ahot air drier at 100 0 C for one minute.
  • the resulting laminate was aged in a hot air drier at 7O 0 C for 24 hours. Then, the release sheet in contact with the foam layer was peeled off to produce a 2 D thickness of a polyurethane foam dressing which includes a 30 D thickness of an outer film layer with moisture-permeable waterproofing.
  • a polyurethane foam dressing was produced using knife-over-roll coating such that it includes a drug- containing layer taking up 10% of the total area of the foam layer of the dressing produced in the step (3) and having a thickness of 0.2 D, as shown in FIG. 2.
  • Example 1 were added 80 parts by weight of deionized water (DIW), 20 parts by weight of glycerin as a moisturizer and 2 parts by weight of a surfactant (F-68 available from BASF Corp.). After stirring at a rate of 3,000 RPM for 10 sec, the mixture was applied to a silicon release sheet (available from Youlchon Chemical Co., Ltd.), rendering the sheet to be coated with the mixture using a 2.2 D thickness gauge.
  • DIW deionized water
  • F-68 available from BASF Corp.
  • Example of a moisture-permeable waterproof polyurethane film was laminated on the coating such that a gap between the film and the coating was adjusted to 2.2 D, immediately followed by drying in ahot air drier at 100 0 C for one minute.
  • Comparative Production Example 4 (Sample 1): 10 D/D [175] Comparative Production Example 5 (Sample 2): 30 D/D [176] Comparative Production Example 6 (Sample 3): 60 D/D [177] After stirring at a rate of 3,000 RPM for 10 sec, the mixture was applied to a silicon release sheet (available from Youlchon Chemical Co., Ltd.), rendering the sheet to be coated with the mixture using a 2.2 D thickness gauge.
  • a silicon release sheet available from Youlchon Chemical Co., Ltd.
  • Example of a moisture-permeable waterproof polyurethane film was laminated on the coating such that a gap between the film and the coating was adjusted to 2.2 D, immediately followed by drying in ahot air drier at 100 0 C for one minute.
  • a drug release test for the polyurethane foam dressing thus produced was conducted to obtain the release speedand release amount of the drug contained therein. The test was carried out in accordance with the following conditions and methods. The drug release behavior was observed for 48 hours. The results were shown in Table 4 and FIG. 10.
  • a segment of 2 cm x 2 cm was prepared from a silver sulfadiazine-containing polyurethane foam dressing.
  • Drug release test for the segment was conducted in a shaking incubator (DA-SI-LL, Donga Science) under conditions of a temperature range of 37+5 0 C and a rate of 100 RPM.
  • a released drug of 3 mL was collected using a microsyringe at regular intervals. To maintain the desired sink conditions of the released drug, a drug was supplemented in an amount and temperature equivalent to the collected one.
  • the concentration of the sample collected was detected at 254 nm using a UV Spectrometer and plotted as a graph representing a ratio (D/D) of a released drug amount to a total drug amount contained in the polyurethane foam dressing. The results were shown in Table 4 and FIG. 10.
  • Example 1 were added 80 parts by weight of deionized water (DIW), 20 parts by weight of glycerin as a moisturizer and 2 parts by weight of a surfactant (F-68 available from BASF Corp.). After stirring at a rate of 3,000 RPM for 10 sec, the mixture was applied to a silicon release sheet (available from Youlchon Chemical Co., Ltd.), rendering the sheet to be coated with the mixture using a 2.2 D thickness gauge.
  • DIW deionized water
  • F-68 available from BASF Corp.
  • Example of a moisture-permeable waterproof polyurethane film was laminated on the coating such that a gap between the film and the coating was adjusted to 2.2 D, immediately followed by drying in ahot air drier at 100 0 C for one minute.
  • DIW deionized water
  • a polyurethane foam dressing was produced using knife-over-roll coating such that it includes a drug-containing layer taking up 80% of the total area of the foam layer of the dressing produced in the step (3) and having a thickness of 0.2 D, as shown in FIG. 2.
  • a novel method for coating a drug on the surface of the dressing according to the present invention enables production of a polyurethane foam dressing capable of decreasing a use amount of an expensive antibacterial agent and increasing a drug release amount, as compared to conventional methods wherein a wound healing adjuvant (e.g., antibacterial agent) is included in the polyurethane dressing.
  • a wound healing adjuvant e.g., antibacterial agent
  • the present invention provides a polyurethane foam dressing comprising a novel drug-containing layer to which an improved drug addition method is applied.
  • drug release can be favorably carried out by a drug- containing layer separated from a foam layer. Accordingly, there can be prevented drug waste which results from addition of excessive drugs.
  • the polyurethane foam dressing enables drug release, regardless of secretion/nonsecretion of exudates and the amount of exudates secreted, thus enabling sufficient delivery of drugs even to wounds hardly secreting exudates as well as wounds in a middle or late stage.
  • a foam dressing in any shape suitable for wound conditions can be manufactured and be put to practical use.

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Abstract

La présente invention concerne un pansement à base de mousse de polyuréthanne comportant une couche médicamenteuse et son procédé de fabrication, permettant la cicatrisation d'une plaie infectée ou d'une plaie à risque d'infection. Grâce à la formation d'une couche médicamenteuse séparée d'une couche de mousse, le pansement à base de mousse polyuréthanne permet l'administration efficace de médicaments à la plaie, indépendamment de la sécrétion ou non d'exsudat et de la quantité d'exsudat sécrété. Le procédé comprend la formation d'une couche non poreuse de film polyuréthanne imperméable à l'eau, la formation d'une couche collante de mousse polyuréthanne de type gel, la stratification de la couche de mousse polyuréthanne sur la couche de film polyuréthanne, et la formation d'une couche médicamenteuse. Le pansement à base de mousse polyuréthanne est apte à la prévention de perte de médicament provoquée par l'addition de médicament excédentaire, selon une libération efficace de médicaments grâce à la couche médicamenteuse séparée de la couche de mousse. En outre, le pansement à base de mousse polyuréthanne permet la libération efficace de médicaments, indépendamment de la sécrétion ou non d'exsudat, permettant ainsi une administration efficace de médicaments même à des plaies ne sécrétant que peu d'exsudat ainsi qu'à des plaies qui sont au stade intermédiaire ou avancé.
PCT/KR2007/002078 2006-05-19 2007-04-27 Pansement à base de mousse de polyuréthanne comportant une couche médicamenteuse et son procédé de fabrication Ceased WO2007136176A1 (fr)

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WO2013054103A1 (fr) * 2011-10-10 2013-04-18 Queen Mary University Of London Revêtements antimicrobiens
EP2656862A1 (fr) * 2012-04-24 2013-10-30 The Procter & Gamble Company Substrat comprenant un ou plusieurs oligosaccharides du lait humain et article absorbant jetable comprenant le substrat
CN103495199A (zh) * 2013-10-08 2014-01-08 山东赛克赛斯药业科技有限公司 一种治疗激光灼伤和烧烫伤的水凝胶伤口敷料及其制备方法
EP2525955A4 (fr) * 2010-01-20 2014-04-02 Kci Licensing Inc Garnitures en mousse pour blessures pourvues de régions de densités supérieure et inférieure, pansements, et méthodes
CN115382000A (zh) * 2022-07-11 2022-11-25 上海健康医学院 一种具有抗菌涂层的敷料及其制备方法

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KR101022884B1 (ko) 2009-06-12 2011-03-16 주식회사 원바이오젠 약물층을 포함하는 폴리우레탄 폼 드레싱제 및 그 제조방법
KR102253879B1 (ko) 2018-07-30 2021-05-20 주식회사 원바이오젠 은-활성탄 복합체를 함유하는 폴리우레탄 폼 드레싱재 및 그 제조방법
KR102158195B1 (ko) * 2018-12-17 2020-09-22 유한회사 팜스코리아 약물 수용홈이 형성된 폼 드레싱재
KR20210055949A (ko) 2019-11-08 2021-05-18 주식회사 엠마헬스케어 국소부위 상처 치료용 콜드플라즈마 및 저준위레이저 융합 패치

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KR20020046619A (ko) * 2000-12-15 2002-06-21 박명환 다층구조의 폼 드레싱재 및 그 제조방법
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Cited By (12)

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Publication number Priority date Publication date Assignee Title
EP2525955A4 (fr) * 2010-01-20 2014-04-02 Kci Licensing Inc Garnitures en mousse pour blessures pourvues de régions de densités supérieure et inférieure, pansements, et méthodes
US9770368B2 (en) 2010-01-20 2017-09-26 Kci Licensing, Inc. Foam wound inserts with regions of higher and lower densities, wound dressings, and methods
EP3569376A1 (fr) * 2010-01-20 2019-11-20 KCI Licensing, Inc. Garnitures en mousse pour blessures pourvues de régions de densités supérieure et inférieure, pansements et procédés
US10792191B2 (en) 2010-01-20 2020-10-06 Kci Licensing, Inc. Foam wound inserts with regions of higher and lower densities, wound dressings, and methods
US11224542B2 (en) 2010-01-20 2022-01-18 Kci Licensing, Inc. Foam wound inserts with regions of higher and lower densities, wound dressings, and methods
WO2013054103A1 (fr) * 2011-10-10 2013-04-18 Queen Mary University Of London Revêtements antimicrobiens
EP2656862A1 (fr) * 2012-04-24 2013-10-30 The Procter & Gamble Company Substrat comprenant un ou plusieurs oligosaccharides du lait humain et article absorbant jetable comprenant le substrat
WO2013163075A1 (fr) * 2012-04-24 2013-10-31 The Procter & Gamble Company Substrat comprenant un ou plusieurs oligosaccharides de lait humain et article absorbant jetable comprenant le substrat
US9492337B2 (en) 2012-04-24 2016-11-15 The Procter & Gamble Company Substrate comprising one or more human milk oligosaccharides and disposable absorbent article comprising the substrate
CN103495199A (zh) * 2013-10-08 2014-01-08 山东赛克赛斯药业科技有限公司 一种治疗激光灼伤和烧烫伤的水凝胶伤口敷料及其制备方法
CN103495199B (zh) * 2013-10-08 2015-10-21 山东赛克赛斯药业科技有限公司 一种治疗激光灼伤和烧烫伤的水凝胶伤口敷料及其制备方法
CN115382000A (zh) * 2022-07-11 2022-11-25 上海健康医学院 一种具有抗菌涂层的敷料及其制备方法

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