EP4041326A1 - Agent tensioactif à base de mousse - Google Patents

Agent tensioactif à base de mousse

Info

Publication number
EP4041326A1
EP4041326A1 EP20875065.3A EP20875065A EP4041326A1 EP 4041326 A1 EP4041326 A1 EP 4041326A1 EP 20875065 A EP20875065 A EP 20875065A EP 4041326 A1 EP4041326 A1 EP 4041326A1
Authority
EP
European Patent Office
Prior art keywords
foam
urethane
wound dressing
antimicrobials
emulsion
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.)
Pending
Application number
EP20875065.3A
Other languages
German (de)
English (en)
Other versions
EP4041326A4 (fr
Inventor
Gary Fujii
Sam ON HO
Michael Mayeda
Phil Sheridan
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Keneric Healthcare LLC
Original Assignee
Molecular Express Inc
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
Application filed by Molecular Express Inc filed Critical Molecular Express Inc
Publication of EP4041326A1 publication Critical patent/EP4041326A1/fr
Publication of EP4041326A4 publication Critical patent/EP4041326A4/fr
Pending legal-status Critical Current

Links

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
    • 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
    • A61L15/46—Deodorants or malodour counteractants, e.g. to inhibit the formation of ammonia or bacteria
    • 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
    • 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
    • A61L15/48—Surfactants
    • 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
    • A61L15/60—Liquid-swellable gel-forming materials, e.g. super-absorbents
    • 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
    • A61L2300/10—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing inorganic materials
    • A61L2300/102—Metals or metal compounds, e.g. salts such as bicarbonates, carbonates, oxides, zeolites, silicates
    • A61L2300/104—Silver, e.g. silver sulfadiazine
    • 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

Definitions

  • the present invention relates generally to wound dressings such as are useful in treatment of exuding wounds both in first aid as well as longer term treatment situations, particularly where the dressing prevents or inhibit the growth of microbes in the wound bed, thus accelerating healing of the wound.
  • Flexible cellular polyurethane foams are used from such things as furniture cushioning, carpet underlayment, and cosmetic pads and applicators.
  • Cellular urethane foams have traditionally been prepared using TDI (toluene diisocyanate) polyisocyanate components.
  • MDI methylene diisocyanate
  • TDI toluene diisocyanate
  • HDI methylene diisocyanate
  • These starting materials can be used to manufacture dense foams, i.e., greater than 4.5 lb/ft 3 .
  • Various references in the prior art teach the use of resiliently compressible foamed plastic and similar synthetic materials for wound dressings. Such materials can permit comfortable application of pressure even on curved or other non-planar body surfaces.
  • a foamed plastic may not be critical in the case of cushioning, insulating or packing materials, they are highly critical for purposes of an adequate wound treatment-dressing.
  • British Patent 1417962 discloses the use of a non-reticulated polyurethane foam which is modified at the wound-facing inner surface, by application of heat and pressure, to give a layer of collapsed cells, which layer is soft, pliant, and facilitates flow of moisture from the wound into the body of the foam material.
  • U.S. Pat. No. 3,903,232 discloses hydrophilic cross-linked polyurethane foams, which are said to be useful for the absorption of body fluids and may be used for external body cleaning, for internal body usage, and as absorptive products such as diapers.
  • the foams are prepared by reacting particular isocyanate-capped polyoxyethylene polyols having an isocyanate functionality greater than 2 with large amounts of an aqueous reactant, preferably water.
  • EP-A-0335669 discloses a hydrophilic foam composition
  • a hydrophilic foam composition comprising the “in situ” reaction product of an isocyanate-capped polyether prepolymer, a hydrophilic agent capable of absorbing water, an adjuvant comprising an alcohol, a wetting agent and water.
  • One application which is proposed for the foam composition is in the manufacture of wound dressings.
  • the composition is said to carry the adjuvant releasably, so that at least a portion of the adjuvant is released into an external liquid (e.g., wound exudate) with which the foam composition comes into contact.
  • U.S. Pat. No. 4,728,323 discloses a method of manufacturing a wound dressing which is comprised of a “substrate” coated with an antimicrobially effective film of a silver salt.
  • the film is preferably deposited on the substrate by vapor or sputter deposition techniques.
  • the support sheet with the attached dressing is suspended in a vacuum vessel and all of the air is removed.
  • the material is vaporized by heating to its melting point with an electron beam.
  • U.S. Pat. No 4,738,849 discloses a composite wound dressing with separate layers which are subjected to what appears to be a liquid treatment followed by freeze drying.
  • U.S. Pat. No. 4,997,425 discloses a wound dressing which, in one embodiment, is said to release an antimicrobial material.
  • the antimicrobial solution is poured into a vessel and then subjected to quenching and freezing under vacuum so that a sheet-molded porous layer is produced.
  • U.S. Pat. No. 5,455,604 discloses a wound dressing of multiply layers which includes a “net” in which the strands and junctures are formed integrally during manufacture. The use of a hydrophilic polyurethane foam together with a silver salt which incorporation into the proto-foam prior to polymerization is discussed.
  • U.S. Patent Publication No. 2002/0168400 discloses a resin foam wound dressing in which the resin layer has a collagen layer dispersed over the foam layer, followed by freeze drying.
  • U.S. Patent Publication No. 2005/0124724 discloses a polymer composition which has a bio-active agent “distributed therein.”
  • Another object of the present invention is to provide a wound dressing having at least a wound contacting layer which comprises an absorbent polyurethane foam, and a composition comprising a combination of active wound treatment-dressing components or agents incorporated therein.
  • the wound dressing of the invention provides wound treatment, by providing a wound dressing (for humans and animals) that can have embedded within the dressing itself, anti-microbial/anti- viral/anti-fungal/anti-anthelmintic molecules.
  • this combination of features exhibits the ability to assist skin and exposed tissue to heal faster and more naturally by preventing and aborting infection, and by actually encouraging tissue growth via increased blood-flow, while noticeably reducing wound pain and discomfort.
  • the preferred invention comprises a urethane foam pad dressing; one or more hydrophilic surfactants incorporated therein, and optionally, one or more antimicrobials also incorporated therein, preferably as a pre-formed mixture with the hydrophilic surfactants.
  • the preferred wound treatment-dressing includes a dressing body having at least a wound contacting surface layer which is formed from a biocompatible, moisture permeable, urethane open-cell foam.
  • the foam which makes up at least the wound contacting surface of the dressing body exists as a foam matrix comprised of interconnected foam cells with cell walls which has incorporated therein a combination of inorganic antimicrobials as active agents, the active agents being incorporated into the foam matrix both topically on a foam cell surface and integrally within the foam cell wall.
  • the preferred hydrophilic surfactants can be of several different types such as the alkylene oxide polymers discussed in Herzberger et ah, Chem. Rev. 116: 2170- 2243, 2016.
  • Poloxamers and Pluronics include, but are not limited to, poloxamer-101, -105, -105 benzoate, -108, -122, -123, -124, - 181, -182, -182 dibenzoate, -183, -184, -185, -188, -212, -215, -217, -231, - 234, - 235, -237, -238, -282, -284, -288, -331, -333, -334, -335, -338, -401, -402, -403, and -407 and pluronics L10, L31, L35, L44, L61, L62, L64 L92, and L121.
  • the active agents that can be incorporated into the hydrophilic foam of the present invention can be selected from a group consisting of gram-positive antimicrobials, gram negative antimicrobials, iodine, and ionic and colloidal silver.
  • Antibacterial, antifungal, and antiviral properties may be conveyed in any appropriate matter for example the addition of silver salts in the form of zinc oxides, titanium dioxides, silver sulfates, silver citrates, silver acetates, silver carbonates, silver lactates and silver phosphates, for example. Additionally, zeolites containing approximately 15% by weight of silver ion may also be used.
  • the foam body of the wound treatment dressing has incorporated therein a zirconium phosphate-based ceramic ion-exchange resin containing silver in the form of silver ions which slowly releases silver ions via an ion exchange mechanism.
  • the preferred foam body has a volume absorbency ratio which is greater than about 12:1 and the gentian- violet and methylene blue components are present in the foam matrix as particles which range in diameter from about 10 nanometers to 800 microns.
  • the active agents are at least partially embedded within the foam cells, which thereby immobilizes the active agent.
  • each antimicrobial agent is physically mixed into the polymer foam ingredients prior to foaming.
  • the selected antimicrobial agents are embedded in the foam compartment walls.
  • the foam is non-leaching with respect to the anti microbial agents.
  • “Non-leaching” as used herein refers to no more than 10%, preferably no more than 5%, and most preferably no more than 1% or 0.1% of one or more anti microbial agents are leached when measured in accordance with BS EN ISO 10993- 12:2012.
  • the anti-microbial agents include methylene blue, gentian violet and silver (as ions or salts), and the silver is non-leachable.
  • hydrophilic surfactant incorporated into the polyurethane foam
  • other hydrophilic materials such as hydrogels, or natural or synthetic fibers or sponges may find utility as well.
  • Exemplary polyurethane foams of the invention are composed of diisocyanate molecules either as monomers or as pre -polymers, a hydrophilic surfactant and, optionally, one or more antimicrobial agents.
  • the resulting hydrophilic foam products can be used wherever wound dressings are required and in combination with other wound care products including, but not limited to, cosmetic pads, puffs, applicators, foam gauzes, bandages, wipes, gels, collagen pads, creams, ointments or the like.
  • Various open-cell- structure polymer “foam” membranes are known in the prior art. So-called “liquid immersion” techniques with air drying are taught in the prior art for manufacturing foams of the general type under consideration.
  • a preferred wound treatment-dressings comprise a dressing body having at least a wound contacting surface layer which is formed from a medically inert urethane open-cell foam.
  • a medically inert urethane open-cell foam there may be other polymer foams of the same general type, such as open-cell sponge rubber or foamed plastics, which can be impregnated with the active agents to be described, and which may become obvious to others skilled in the art of open-cell foam production.
  • open-cell polymer foams are included in the scope of this invention, as well as absorbent fiber materials.
  • a foam preparation may be prepared as follows:
  • An aqueous solution is prepared by mixing 120 gallons distilled H2O) with
  • [0029] Mix 1000 lbs of Hypol 2002 with 1250 to 15001bs of the aqueous solution. Each 1000 lbs of the aqueous solution will produce about 670-lbs of dry foam.
  • the temperature of the aqueous solution can be in the range of 45° F to 50° F, and the Hypol 2002 may be at 80° F.
  • the mixing head creates an emulsion of Hypol 2002 pre-polymer in water, and the function of the mixing head is to create a uniform emulsion.
  • the mixing head emulsifier unit is the primary determinant of the size and distribution of the polymer-aqueous emulsion and the resulting cell structure of the foam.
  • foaming reaction begins. Typically, the mixture might be mixed for 15-seconds, dropped onto the continuous roll-table and get evenly spread. The emulsion will begin to creme (rise and foam), and then cure for at least 10- minutes. The mix should be spread quickly and evenly across the width of a release paper roll, and individualized distribution boxes or knife doctor blades, are needed to get a uniform layer prior to the gel and creme time.
  • gellation initiates, the formation of the gel provides sufficient strength to sustain the pressure from the CO2 formation which stretches the gel and forms a pore or cell. Dry nitrogen gas is typically introduced at the mix head to instill very fine tiny bubbles into the emulsion to act as nucleation sites for the CO2 off-gassing. It is the precursor to the open cell structure formed by the CO2 gas and constrained by urethane gelation and cross-linking.
  • the foam may then be dried in a radio-frequency (RF) dryer, or, a hot-air suction dryer.
  • RF radio-frequency
  • Table 1 Characteristics of wound dressing foam made with different surfactants.
  • Leachates in deionized water from a foam wound dressing lot prepared according to the invention was were analyzed in triplicate for methylene blue, gentian violet and silver concentrations in accordance with BS EN ISO 10993-12:2012.
  • the methylene blue and gentian violet contents of the extract were analyzed by reverse-phase HPLC. Detection of components was by UV absorbance at 590 nm and 660 nm for methylene blue and gentian violet, respectively. Methylene blue eluted at approximately 6.7 min; gentian violet eluted at approximately 15.3 min. Methylene blue and gentian violet quantification was accomplished by correlation of peak areas to respective standard curves. Measurements were performed in triplicate. Concentrations were reported as averages with standard deviations Silver concentration of the leached liquid was analyzed by ICP-MS. All samples were measured in triplicate according to EPA 6020 ⁇
  • the leached methylene blue concentration was 0.1112 + 0.0005 mg/g dressing, the leached gentian violet concentration was 0.0249 + 0.0005 mg/g dressing, and the leached silver concentrations was 1.02 + 0.04 pg/g dressing.
  • Percent leaching from the foam is as follows:

Landscapes

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

Abstract

L'invention concerne un pansement en mousse d'uréthane ; un ou plusieurs tensioactifs hydrophiles incorporés dans celui-ci, et facultativement, un ou plusieurs agents antimicrobiens également incorporés dans celui-ci, de préférence sous la forme d'un mélange préformé avec les tensioactifs hydrophiles.
EP20875065.3A 2019-10-10 2020-10-09 Agent tensioactif à base de mousse Pending EP4041326A4 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201962913696P 2019-10-10 2019-10-10
PCT/US2020/055062 WO2021072254A1 (fr) 2019-10-10 2020-10-09 Agent tensioactif à base de mousse

Publications (2)

Publication Number Publication Date
EP4041326A1 true EP4041326A1 (fr) 2022-08-17
EP4041326A4 EP4041326A4 (fr) 2023-11-01

Family

ID=75438168

Family Applications (1)

Application Number Title Priority Date Filing Date
EP20875065.3A Pending EP4041326A4 (fr) 2019-10-10 2020-10-09 Agent tensioactif à base de mousse

Country Status (2)

Country Link
EP (1) EP4041326A4 (fr)
WO (1) WO2021072254A1 (fr)

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5455604A (en) 1991-04-29 1995-10-03 Tektronix, Inc. Ink jet printer architecture and method
US20020168400A1 (en) 2001-05-11 2002-11-14 Biocore Medical Technologies, Inc. Collagen/synthetic resin foam wound dressing
CA2486057A1 (fr) * 2002-05-16 2003-11-27 Ferris Pharmaceuticals, Inc. Compositions de mousse hydrophile presentant des proprietes antibacteriennes
EP1493452B1 (fr) * 2003-06-18 2010-02-03 Corpura B.V. Mousse de polyuréthane hydrophile flexible ayant une activité antimicrobiènne
US7745509B2 (en) 2003-12-05 2010-06-29 3M Innovative Properties Company Polymer compositions with bioactive agent, medical articles, and methods
US8343523B2 (en) * 2005-08-22 2013-01-01 Quick-Med Technologies, Inc. Disinfectant with durable activity based on alcohol-soluble quaternary ammonium polymers and copolymers
EP2072063A1 (fr) 2007-12-22 2009-06-24 Bayer Innovation GmbH Mousse de polyuréthane à base de pré-polymère hydrophile cellulaire résistante aux infections, procédé pour sa fabrication et son utilisation dans des pansements antiseptiques
EP2467173B8 (fr) * 2009-08-21 2019-06-19 Novan, Inc. Pansements, procédés d'utilisation de ceux-ci et procédés de formation de ceux-ci
EP3328460A4 (fr) 2015-07-28 2019-03-27 NewMedical Technology, Inc. Systèmes et procédés de production de mousses hydrophiles
GB201711181D0 (en) * 2017-07-12 2017-08-23 Smith & Nephew Polymer foam material, device and use

Also Published As

Publication number Publication date
EP4041326A4 (fr) 2023-11-01
WO2021072254A1 (fr) 2021-04-15

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