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WO2004037307A1 - Pansement fluidique comprenant du polyurethanne partiellement durci - Google Patents

Pansement fluidique comprenant du polyurethanne partiellement durci Download PDF

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Publication number
WO2004037307A1
WO2004037307A1 PCT/GB2003/004609 GB0304609W WO2004037307A1 WO 2004037307 A1 WO2004037307 A1 WO 2004037307A1 GB 0304609 W GB0304609 W GB 0304609W WO 2004037307 A1 WO2004037307 A1 WO 2004037307A1
Authority
WO
WIPO (PCT)
Prior art keywords
wound dressing
wound
composition
component
polyurethane
Prior art date
Application number
PCT/GB2003/004609
Other languages
English (en)
Inventor
Deborah Addison
Edward Schonfeld
Peter Wachtel
Sally-Anne Norris
Original Assignee
Johnson & Johnson Medical Limited
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from GB0303821A external-priority patent/GB2394418B/en
Application filed by Johnson & Johnson Medical Limited filed Critical Johnson & Johnson Medical Limited
Priority to EP03769648A priority Critical patent/EP1558300A1/fr
Priority to AU2003278338A priority patent/AU2003278338A1/en
Priority to US10/532,520 priority patent/US7538257B2/en
Publication of WO2004037307A1 publication Critical patent/WO2004037307A1/fr
Priority to US12/470,620 priority patent/US8481801B2/en

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Classifications

    • 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
    • A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
    • A61L26/0009—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials
    • A61L26/0019—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds

Definitions

  • the present invention relates to fluid wound dressings that can be used to fill cavity wounds.
  • Cavity wounds can be a problem to treat due to high levels of exudate production, the irregular contours of the wound site, the loss of tissue (sometimes undermining the surrounding skin) and the potential for tracts or sinuses.
  • the full extent of the cavity wound is not always obvious from a visual assessment, which complicates the treatment choice.
  • the main wound management regime for cavity wounds is much the same as for other wounds, that is to say moist wound healing and exudate management.
  • the standard treatments tend to be based around packing the cavity with gauze, alginates or some other absorbent material.
  • This primary dressing is often held in place with a secondary dressing, such as a film, foam or gauze, depending on the level of exudation.
  • the care giver also needs to ensure that all of the cavity wound dressing is removed after treatment, unless the dressing is fully bioresorbable.
  • Cavity wounds can be heavily exuding, and it is therefore desirable to use a cavity wound filling material that can transport material by capillary action or diffusion from the wound site to a moisture-absorbent secondary dressing.
  • US-A-4837285 describes the use for soft tissue cavity filling of resorbable collagen sponge beads having diameters of from 0.1 to 4.0 mm.
  • the beads have pore sizes of from 50 to 350 micrometers. Such beads can be difficult to handle, and are not suitable for use as a removable, absorbent dressing for deep wounds.
  • DE-A-4037931 describes a deep cavity wound dressing structure consisting of a cavity-filling plug of resorbable collagen foam containing an array of hollow resorbable filaments.
  • the filaments are bundled together at one end, and connected to a drain for wound fluid, whereby the wound fluid is continuously drained from the wound cavity through the hollow filaments.
  • Such a structure is relatively expensive to construct, and insufficiently conformable to a wide range of wound cavity shapes.
  • EP-A-0171268 describes absorbent, non-adherent wound dressings for use in the treatment of deep wounds, wherein the dressing comprises a porous bag containing individual pieces of a conformable, resilient, absorbent hydrophilic foam.
  • the porous bag may be provided with a string to assist removal of the bag from the wound after use. This structure may be insufficiently conformable to a wide range of wound cavity shapes.
  • the present invention provides a wound dressing composition comprising a partially cured polyurethane fluid.
  • wound dressing composition refers to a composition suitable for injection directly into wounds to provide a dressing for the wound. It does not encompass hardening compositions for orthopedic casts or the like.
  • polyurethane in this specification encompasses polymers comprising urethane and/or urea linkages.
  • the wound dressing according to the present invention is a fluid.
  • the fluid may be a liquid, preferably a viscous liquid, or it may be a paste, or it may be a non- Newtonian fluid. This property makes the wound dressing composition especially suitable for completely filling a cavity wound by injection or pouring, or simply by working the fluid into the wound cavity in with a spatula or similar implement.
  • the wound dressing composition comprises a partially cured polyurethane fluid.
  • a partially cured polyurethane fluid Preferably, it comprises at least 50% by weight of the polyurethane components, and more preferably at least 75%, 90%, or 95% by weight of the polyurethane components.
  • the polyurethane fluid is partially cured. That is to say, it has been prepared by mixing a diisocyanate or a polyisocyanate composition with a curing composition, such as a diol or polyol composition, but the reaction between the components has not gone to completion. For example, at least 1 % of the isocyanate groups originally present in the isocyanate composition may still be present (i.e.
  • the absolute amount of unreacted isocyanate in the wound dressing composition is low, in order to reduce adverse reaction of isocyanate in vivo.
  • the absolute amount of unreacted isocyanate present in the composition according to the invention is less than about 4wt.% (i.e. about 1meq NCO/gram), more preferably less than about 2wt.%, and most preferably from about 0.1wt.% to about 1 wt.%.
  • the polyurethane fluid starts to cure on mixing of the two components and continues to cure in situ in the wound to form a wound filling dressing that conforms exactly to the shape of the wound.
  • the resulting cured polyurethane is preferably soft and flexible for comfort, but preferably has sufficient wet and dry tensile strength to be removed in one piece from the wound after use.
  • the dry tensile strength of the as-cured polyurethane is at least about 5N/cm 2 , more preferably at least about 10N/cm2.
  • the wet tensile strength after immersion in physiological saline for 24 hours at 25C is at least 50% of the dry tensile strength, more preferably at least 75% of the dry tensile strength.
  • the cured polyurethane is preferably sufficiently hydrophilic to wick exudate from the wound to a secondary dressing, but preferably does not absorb enough wound fluid to give rise to swelling that would exert undesirable pressure.
  • the absorbency of physiological saline at 25°C after 24 hours is less than 200wt.% based on the weight of the as-cured polyurethane, more preferably less than 100wt.%.
  • the wound dressing composition comprises additives, for example selected from the group consisting of humectants, plasticisers, hydrocolloids, blowing agents, medicaments, siloxane wetting agents and mixtures thereof.
  • the optional plasticisers assist in providing a flexible, soft cured polyurethane in situ in the wound.
  • Suitable plasticisers include medically acceptable mineral oils, silicone oils, vegetable oils, stearates, hydrogenated ethers and esters, and mixtures thereof.
  • humectants assist in maintaining the desired moist wound healing environment in situ in the wound.
  • Suitable humectants include medically acceptable polyhydric alcohols such as glycerol, sorbitol, soft paraffin, urea creams, lanoline, sodium pyrrolidone carboxylate (PCANa), gamma linolenic acid (evening primrose oil) and soya oil, tea tree oil, coconut oil (or any other nut oil), camomile, aloe vera, jojoba oil, cocoamide or mixtures thereof.
  • polyhydric alcohols such as glycerol, sorbitol, soft paraffin, urea creams, lanoline, sodium pyrrolidone carboxylate (PCANa), gamma linolenic acid (evening primrose oil) and soya oil, tea tree oil, coconut oil (or any other nut oil), camomile, aloe vera, jojoba oil, cocoamide or
  • the optional hydrocolloids assist in adjusting the water absorbency and wicking properties of the cured polyurethane composition.
  • Suitable hydrocolloids include alginates, pectin, gums such as guar gum or xanthan gum, modified celluloses such as carboxymethyl cellulose and hydroxyethyl cellulose, modified starches such as sodium starch glycolate, and mixtures thereof.
  • the optional blowing agents provide the cured polyurethane with a foamed or porous structure to increase its permeability to wound fluid. Suitable blowing agents include water (which reacts with isocyanate groups to form urea linkages and carbon dioxide), and citric acid/sodium bicarbonate or formic acid or hydroflurocarbon.
  • the wound dressing compositions according to the invention have a curing time of from about 0.1 to about 180 minutes, preferably about 2 to about 30 minutes.
  • the optional siloxane wetting agents provide the cured polyurethane with increased wetting or wicking properties.
  • Suitable surfactants include dimethyl siloxanes, PLURONICS (Registered Trade Mark of BASF), BRIJ (Registered Trade Mark of ICI) or mixtures thereof
  • the present invention provides a wound dressing comprising a wound dressing composition according to the first aspect of the invention.
  • the wound dressing according to this aspect of the invention may further comprise reinforcing elements to assist removal of the cured polyurethane composition in one piece from the wound.
  • Suitable reinforcing elements include woven or nonwoven fabrics, polymer webs or meshes.
  • the reinforcing elements may be introduced into the wound cavity before, during or immediately after introduction of the partially cured polyurethane fluid.
  • the wound dressing according to the invention may further comprise drainage elements to assist drainage of exudate from wounds.
  • Suitable drainage elements includes flexible polymeric tubes and flexible biodegradable tubes, such as those described in DE-A-4037931 , the entire content of which is incorporated herein by reference.
  • the present invention provides a wound dressing kit comprising: (a) a polyurethane prepolymer; and (b) a curing agent for the polyurethane prepolymer.
  • the components (a) and (b) are adapted to be used in combination to form a wound dressing composition according to the present invention.
  • the components (a) and (b) are stored separately in a single package for mixing immediately before use.
  • the package may comprise a barrier between the components that can be opened to allow the components to mix inside the package immediately before use.
  • the package may comprise a mixing chamber for sterile mixing of the components immediately before use.
  • the wound dressing kit is adapted for the preparation of a wound dressing according to the invention by mixing of components (a) and (b).
  • the kit may further comprise reinforcing elements and/or drainage elements as hereinbefore described. It may further comprise a secondary dressing for application over the wound dressing of the invention.
  • both component (a) and component (b) are liquid at temperatures above 10°C, preferably at temperatures above 5°C, and more preferably at temperatures above 0°C. This assists mixing of the components at ambient temperatures.
  • Component (a) preferably comprises an isocyanate capped prepolymer.
  • the isocyanate-capped prepolymer comprises from 0.1 to 1 meq NCO groups/g.
  • the isocyanate-capped prepolymer is an isocyanate-capped polyether or polyester prepolymer.
  • the prepolymer may be an isocyanate- capped oxyethylene/oxypropylene copolymer. This enables the properties of the polyurethane to be regulated by varying the ration of ethylene oxide to propylene oxide in the prepolymer (high ethylene oxide gives a more hydrophilic product).
  • component (a) may be an isocyanate-capped castor oil, or derivative thereof.
  • component (a) may be produced by reacting a diisocyanate such as isophorone diisocyanate (IPDI) with castor oil, or a glycerol mono- or diester of ricinoleic acid, or a derivative thereof produced by reaction with ethylene oxide or propylene oxide such as CASPOL 5001 or other ricinoleic acid derivatives such as CASPOL 5003
  • the prepolymer is a reaction product of an aliphatic isocyanate, since polyurethanes manufactured from aliphatic isocyanates have superior mechanical properties and superior light stability.
  • the isocyanates used in the prepolymer reaction can be selected from, but not limited to the following: 1 ,4 tetramethylene diisocyanate
  • IPDI Isophorone diisocyanate Methylene bis(4-cyclohexyl)-isocyanate Meta or para xylylene diisocyanate
  • Degussa's T-6040 a mixture of IPDI and its trimer
  • isocyanate capped prepolymers include Degussa's Vestanat (Registered Trade Mark) EPU-937 prepolymer based on IPDI.
  • Other prepolymers could include the HYPOLs (although not aliphatic, they would still work) and other aliphatic prepolymers based on H 12 MDI (4,4'-dicyclohexylmethane diisocyanate) or CHDI (Trans 1 ,4-cyclohexane diisocyanate)
  • Component (a) may further comprise the plasticisers, humectants and hydrocolloids.
  • Component (b) may further comprise the plasticisers, humectants and hydrocolloids.
  • a preferred polyol for preparation of the wound dressings and wound dressing kits according to the present invention is castor oil and other esters of ricinoleic acid and its derivatives.
  • One such derivative is a monoricinoleate ester to which either ethylene oxide or propylene oxide has been added to the hydroxyl group on the ricinoleate, available under the Registered Trade Mark CASPOL 5001.
  • component (b) comprises water as a foaming and polymerising agent.
  • the water in the component (b) reacts with the isocyanate prepolymer to cross-link the isocyanate groups in urea linkages and release CO 2 , which causes the polyurethane reaction mixture to form a foam.
  • the amount of water in the component (b) is from 0.02 to 0.1 parts by weight per part by weight of the isocyanate prepolymer.
  • component (b) comprises chain extending or terminating agents, catalysts or mixtures thereof.
  • component (b) may comprise diamine chain extending/terminating compounds such as 1 ,4-butane diol, 1 , 5- pentane diol or 1 ,6-hexane diol or diamines such as DDM (4, 4' diaminodiphenylmethane) or DAB (1 , 3 diaminobenzene)
  • component (b) further comprises a catalyst for the polymerisation, preferably a diamine such as diazobicyclo octane or dimethylaminoethyl ether.
  • a catalyst for the polymerisation preferably a diamine such as diazobicyclo octane or dimethylaminoethyl ether.
  • the catalysts are present in component (b) in an amount of 0.005 to 0.02 parts by weight, based on one part by weight of the isocyanate prepolymer.
  • Catalysts such as tertiary amines and organometal compounds, most preferably organotin catalysts may also be present.
  • the catalyst to be employed should be a non-cytotoxic catalyst, for example one of the catalysts listed in US Patent 4,332,927, the entire content of which is incorporated herein by reference.
  • an organotin derivative made with castor oil for example, an organotin derivative made with castor oil.
  • the component (b) comprises a polyurethane or polyurea chain terminating compound, preferably selected from monohydric alcohols and amines. More preferably, the component (b) comprises a mixture of mono-amines and diamines.
  • the amounts of chain extending and terminating compounds influence the physical properties of the foam.
  • amine/diamine chain terminating/extending compounds react with the prepolymer very much faster than water and alcohols. For example, the tackiness of the foam increases with increasing monohydric alcohol or monoamine content in component (b).
  • the chain extending and terminating compounds are present in component (b) in an amount of 0.05 to 0.4 parts for alcohols and 0.01 to 0.05 parts for the amines, based on one part by weight of the isocyanate prepolymer.
  • blowing agents and surfactants may also be present in component (b)
  • Component (b) may comprise wound therapeutic materials.
  • Suitable therapeutic materials include: antiseptics such as molecular silver, silver sulfadiazine or chlorhexidine; pain relieving agents such as lignocaine; anti-scarring agents such as mannose-6-phosphate, and agents for promoting wound healing such as growth factors.
  • the present invention provides the use of components (a) and (b) as hereinbefore described for the preparation of a wound dressing composition comprising a partially cured polyurethane fluid for application directly to a wound as a wound dressing.
  • the wound dressing composition is a composition according to the first aspect of the present invention.
  • the present invention further provides a method of treatment of a wound comprising applying thereto a wound dressing composition comprising a partially cured polyurethane fluid.
  • the wound dressing composition is a composition according to the first aspect of the present invention.
  • the composition is applied so as to substantially completely fill the wound.
  • the composition is allowed to cure in the wound.
  • any features that are described as optional or preferred in connection with any one aspect of the present invention are likewise optional or preferred in connection with any other aspect of the invention.
  • the components (a) and (b) described in connection with the kits according to the present invention may be mixed to prepare a wound dressing composition according to any embodiment of the first aspect of the invention.
  • VESTANAT (Degussa) A prepolymer based on isophorone diisocyanate.
  • T-6040 (Degussa) A mixture of isophorone diisocyanate and its trimer
  • EPU-937 (Degussa) A prepolymer based on isophorone diisocyanate.
  • CASPOL 5001 (CasChem) A dihydroxy castor oil derivative ACCLAIM (Bayer) A polypropylene glycol
  • COTIN (CasChem) A proprietary urethane catalyst
  • Purity Gum 59 A low viscosity starch derived from waxy maize
  • SAFOAM B A sodium hydrogen carbonate or sodium bicarbonate
  • a prepolymer was prepared as follows.
  • the prepolymer was prepared by reacting a mixture of Glycerol based polyether polyol (Poly-G-76-120) and a hydroxy terminated polyoxyalkylene polyol (Poly-G- 55-56) with VERSANAT IPDI and sufficient catalyst (Cotin1707) to form the desired prepolymer.
  • the prepolymer had an NCO content of less than 5% resulting in a lower initial NCO value of the final wound dressing.
  • a wound dressing was made using the prepolymer prepared above in component (a).
  • a dressing was prepared using two different methods: (1) mixing the components and pouring the mixture into a plastic cup and (2) mixing the components and coating the mixture onto a release liner. After curing, the coated film was stripped from the release liner and die cut into ribbon and various other shapes. An attractive, sponge-like product was obtained. The strips exhibited very good mechanical integrity both wet and dry.
  • composition can be adjusted to obtain a softer wound dressing.
  • the composition of the above formulation is used here as an example to demonstrate the isocyanate concentration of an initial prototype composition as a function of time.
  • the measured free NCO of the prepolymer before final compounding was less than 5%. It should be kept in mind that the formulation is catalysed, and when the catalysed and un-catalysed portions are mixed together, reaction quickly occurs. Accordingly, available NCO was determined by titration immediately after mixing, and also after 15 and 30 minutes. The data is presented in the following table:

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Materials For Medical Uses (AREA)

Abstract

L'invention concerne une composition de pansement comprenant un fluide polyuréthanne partiellement durci. La composition peut être injectée directement dans une plaie où elle se durcie de manière à former un pansement remplissant une plaie. L'invention concerne également un pansement comprenant une telle composition, ainsi qu'un kit destiné à la préparation de tels pansements et comprenant (a) un prépolymère polyuréthanne; et (b) un agent de durcissement destiné au prépolymère polyuréthanne. Les composants du polyuréthanne comprennent des produits de réaction d'un diisocyanate avec de l'huile de ricin ou un ester associé d'un acide ricinoléique ou de ses dérivés.
PCT/GB2003/004609 2002-10-25 2003-10-24 Pansement fluidique comprenant du polyurethanne partiellement durci WO2004037307A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP03769648A EP1558300A1 (fr) 2002-10-25 2003-10-24 Pansement fluidique comprenant du polyurethanne partiellement durci
AU2003278338A AU2003278338A1 (en) 2002-10-25 2003-10-24 Fluid wound dressing comprising partially cured polyurethane
US10/532,520 US7538257B2 (en) 2002-10-25 2003-10-24 Fluid wound dressing comprising partially cured polyurethane
US12/470,620 US8481801B2 (en) 2002-10-25 2009-05-22 Fluid wound dressing comprising partially cured polyurethane

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US42108502P 2002-10-25 2002-10-25
US60/421,085 2002-10-25
GB0303821A GB2394418B (en) 2002-10-25 2003-02-19 Fluid wound dressing
GB0303821.3 2003-02-19

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US10/532,520 A-371-Of-International US7538257B2 (en) 2002-10-25 2003-10-24 Fluid wound dressing comprising partially cured polyurethane
US12/470,620 Division US8481801B2 (en) 2002-10-25 2009-05-22 Fluid wound dressing comprising partially cured polyurethane

Publications (1)

Publication Number Publication Date
WO2004037307A1 true WO2004037307A1 (fr) 2004-05-06

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PCT/GB2003/004609 WO2004037307A1 (fr) 2002-10-25 2003-10-24 Pansement fluidique comprenant du polyurethanne partiellement durci

Country Status (3)

Country Link
EP (1) EP1558300A1 (fr)
AU (1) AU2003278338A1 (fr)
WO (1) WO2004037307A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007115696A3 (fr) * 2006-04-08 2008-07-10 Bayer Materialscience Ag Mousses polyuréthane pour soigner des plaies
WO2009043499A3 (fr) * 2007-10-05 2010-03-25 Bayer Innovation Gmbh Articles biomédicaux en mousse
CN101885828B (zh) * 2009-05-11 2012-11-21 第一工业制药株式会社 两液型聚氨酯树脂组合物
WO2020040783A1 (fr) * 2018-08-24 2020-02-27 Avent, Inc. Polyuréthanes utilisés en tant que supports d'apport d'oxygène
FR3087126A1 (fr) 2018-10-16 2020-04-17 Jean Francois Van Cleef Dispositif composite de protection moulant une plaie

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4542012A (en) * 1982-07-02 1985-09-17 Minnesota Mining And Manufacturing Company Film-forming composition containing an antimicrobial agent and methods
US4614787A (en) * 1984-11-13 1986-09-30 Thermedics, Inc. Drug dispensing wound dressing
EP0269071A2 (fr) * 1986-11-26 1988-06-01 Dentsply International, Inc. Diacrylate d'uréthane à chaîne allongé et formation d'une empreinte dentaire
EP0336406A2 (fr) * 1988-04-08 1989-10-11 Becton, Dickinson and Company Film détachable durcissable par la lumière ultra-violette et méthode pour sa préparation
US5135964A (en) * 1988-04-08 1992-08-04 Becton, Dickinson And Company Ultraviolet cured peelable film and method therefor
US5192536A (en) * 1990-10-26 1993-03-09 Huprich Carl A Method and composition for coating a wound with polyether polyurethane

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4542012A (en) * 1982-07-02 1985-09-17 Minnesota Mining And Manufacturing Company Film-forming composition containing an antimicrobial agent and methods
US4614787A (en) * 1984-11-13 1986-09-30 Thermedics, Inc. Drug dispensing wound dressing
EP0269071A2 (fr) * 1986-11-26 1988-06-01 Dentsply International, Inc. Diacrylate d'uréthane à chaîne allongé et formation d'une empreinte dentaire
EP0336406A2 (fr) * 1988-04-08 1989-10-11 Becton, Dickinson and Company Film détachable durcissable par la lumière ultra-violette et méthode pour sa préparation
US5135964A (en) * 1988-04-08 1992-08-04 Becton, Dickinson And Company Ultraviolet cured peelable film and method therefor
US5192536A (en) * 1990-10-26 1993-03-09 Huprich Carl A Method and composition for coating a wound with polyether polyurethane

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007115696A3 (fr) * 2006-04-08 2008-07-10 Bayer Materialscience Ag Mousses polyuréthane pour soigner des plaies
WO2007115781A3 (fr) * 2006-04-08 2008-07-24 Bayer Innovation Gmbh Articles moussants biomédicaux
JP2009533500A (ja) * 2006-04-08 2009-09-17 バイエル・マテリアルサイエンス・アクチェンゲゼルシャフト 創傷処置用ポリウレタンフォーム
JP2009533335A (ja) * 2006-04-08 2009-09-17 バイエル・イノベーシヨン・ゲー・エム・ベー・ハー 生物学的医療用発泡物品
US8197835B2 (en) 2006-04-08 2012-06-12 Bayer Innovation Gmbh Biomedical foam articles
WO2009043499A3 (fr) * 2007-10-05 2010-03-25 Bayer Innovation Gmbh Articles biomédicaux en mousse
CN101885828B (zh) * 2009-05-11 2012-11-21 第一工业制药株式会社 两液型聚氨酯树脂组合物
WO2020040783A1 (fr) * 2018-08-24 2020-02-27 Avent, Inc. Polyuréthanes utilisés en tant que supports d'apport d'oxygène
FR3087126A1 (fr) 2018-10-16 2020-04-17 Jean Francois Van Cleef Dispositif composite de protection moulant une plaie
WO2020079330A1 (fr) 2018-10-16 2020-04-23 Van Cleef Jean Francois Dispositif composite de protection moulant une plaie

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EP1558300A1 (fr) 2005-08-03
AU2003278338A1 (en) 2004-05-13

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