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
  • A61L15/20—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons 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
  • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
  • A61L15/18—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing inorganic 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
  • 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
  • A61L15/28—Polysaccharides or their derivatives
• • 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
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P17/00—Drugs for dermatological disorders
  • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
• • 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
• • 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
  • A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
  • A61L2300/204—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials with nitrogen-containing functional groups, e.g. aminoxides, nitriles, guanidines
  • A61L2300/208—Quaternary ammonium compounds
• • 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

• This invention relates wound dressings which comprise an antimicrobial composition where the dressing can be applied to skin, wounds, cuts, abrasions or burns for the prevention or treatment of infections. More particularly the invention relates to a dressing capable of providing effective antimicrobial activity while at the same time avoiding wound and skin irritation and retardation of wound healing. In particular the invention relates to a dressing comprising chemically modified cellulosic fibres comprising an antimicrobial composition where the dressing properties are not compromised by the addition of the antimicrobial composition.
• Non-antibiotic antimicrobials are non-selective chemical agents that can be safe to use on living tissue.
• Molecular iodine, ionic silver and oxidising agents such as sodium hypochlorite and chlorine dioxide have been recognised as antimicrobial agents with effectiveness against a wide range of micro-organisms.
• One barrier is that these antimicrobial agents tend to react with organic materials found in the wound other than the intended microbial targets.
• a further barrier is in the delivery of the antimicrobial composition to the wound.
• the dressing be sufficiently usable such that the antimicrobial wound dressing is conformable, in its dry state, so that a close contact between the wound bed and the dressing is obtained, that the antimicrobial wound dressing maintain its form and structure upon storage and that sufficient strength is maintained in the dressing.
• the dressing is stiff, it is possible that not only will the dressing not conform to the wound site on the patient but also will not conform to the contour of the wound bed. In that circumstance, voids can exist between the dressing and the wound which allow bacteria to grow.
• WO 2012/136968 discloses an antimicrobial composition suitable for use on skin and wounds comprising a source of antimicrobial metal ion and a quaternary cationic surfactant.
• the presence of the quaternary cationic surfactant enhances the effect of the antimicrobial metal ion so that the performance of the antimicrobial metal ion is improved.
• the presence of the quaternary cationic surfactant can increase the rate at which the antimicrobial metal ion exerts its antimicrobial effect.
• the composition preferably also comprises ethylenediaminetetra-acetic acid (EDTA).
• EDTA is preferably present as the di-, tri- or tetra-basic salts of EDTA. We have found that these salts enhance the antimicrobial effect of the ionic metal in disrupting biofilm.
• the presence of the quaternary cationic surfactant enhances the effect of the antimicrobial metal ion, when that metal ion is being applied to a wound from a wound dressing, the presence of the surfactant can affect the drying properties of the dressing so that dressing performance is affected and the wound dressing is sufficiently usable. Treatment with a quaternary cationic surfactant can especially affect the rate of drying of the dressing, increasing it so that the resulting dressing is stiff and does not conform well to the wound.
• GB-A-2220881 and GB-A-2094802 describe the production of carboxymethylcellulose fibres from regenerated cellulose fibres (viscose rayon) fibres or from cotton. It is also known that carboxymethylcellulose fibre of greater absorbency and strength can be produced from solvent-spun cellulose fibre. Such fibres are described in EP 0616650 and are manufactured by reacting solvent spun cellulose fibre with a strong alkali and a monochloroacetic reagent. It is also known that alternative chemical modification of cellulose fibres is possible and also has the effect of increasing the absorbency of the cellulose fibre.
• the cellulose fibre can for instance be modified by sulphonation, for example by substitution with an alkyl sulphonate at one or more of the hydroxyl groups on the anhydroglucose monomers that make up the cellulose backbone forming ether linkages.
• Modified cellulose of this type is known as cellulose sulphonate or cellulose alkyl sulphonate some of the insoluble forms of which are described in WO2012/061225.
• Modifying the cellulose fibre requires the fibre to be exposed to one or more reagents which modify the cellulose by substitution, the degree of substitution determining the absorbency and solubility of the fibre.
• the fibres are washed to remove any unreacted alkali, chloroacetate, alkylsulphonate, other modifying agent or any by-products such as sodium chloride or sodium glycollate.
• An aqueous wash is generally used initially, preferably a mixture of water with a water-miscible organic solvent such as water and IMS (industrial methylated spirit), the major portion of the wash being organic solvent.
• the fibres can be treated with the antimicrobial composition including an antimicrobial metal in a manner such as those described in EP1318842, EP1425050, EP1882482, EP1343510 or EP2262545.
• fibres are dried at low temperature for instance as described in EP 0680344, by forced air drying or radiant heat drying.
• the washing step or steps and the treatment steps, to which the fibres are subjected following modification involve the use of relatively high percentages of organic solvents such as IMS
• the drying of the fibres requires the solvents that are released to be managed from an environmental and safety perspective.
• the treating modified cellulose fibres with an antimicrobial composition comprising a cationic surfactant can result in fibres that have different drying characteristics than untreated fibres, and lead to decreased usability of the resulting wound dressing. For instance, for fibres with an increased rate and/or extent of drying insufficient moisture can lead to embrittlement which in turn leads to fibre breakage on opening, carding and needling and the formation of dust.
• the subsequent reduced length staple fibre may then produce a weaker and lighter fabric with less loft, and lower absorbency. More importantly, the conformability of the dressing can be affected which itself can lead to poor antimicrobial performance as the dressing is not in close contact with the wound.
• the invention provides a wound dressing comprising modified cellulosic fibres treated with an antimicrobial composition comprising a source of an antimicrobial metal ion and a quaternary cationic surfactant, the dressing having a moisture content of at least 10% or at least 10.5%, 11%, 12%, 13%, 14% or 15%, more preferably between 10% and 20% by weight at the time of packaging in a sealed package to maintain the moisture content in that range until the time of use of the dressing.
• antimicrobial a substance that inhibits the growth of, or kills, micro-organisms from the taxonomical kingdoms of bacteria, fungi and protozoa.
• An effective antimicrobial composition is therefore one which is used to reduce and prevent the spread and proliferation of micro-organisms in a specific application. In wound care this can be interpreted in terms of control of cross-infection, prevention or elimination of infection and the reduction of recalcitrant bioburden that can cause delayed healing and chronicity.
• the dressing according to a first aspect of the invention comprises an antimicrobial agent, preferably a metal ion for example the transition metals, antimony, silver, iron, nickel, copper, chromium, manganese, gold, gallium, germanium, mercury, arsenic, aluminium, lead, zinc, bismuth, tin and palladium.
• the metal ion is silver.
• the antimicrobial agent is preferably included in the dressing at a level of from 0.01% to 10% by weight, more preferably 0.1% to 5% and even more preferably 0.5% to 1.5% by weight or 1% to 5%.
• the antimicrobial metal ion is preferably in an aqueous solution comprising from 0.00001% to 1.0% by weight or more preferably 0.0001% to 0.1%, even more preferably 0.0001% to 0.02% by weight or 0.001% to 1.0% by weight.
• the dressings according to the invention comprise a cationic surfactant.
• the cationic surfactant can be a quaternary ammonium salt, an alkyl pyridinium salt, an alkyl imidazolium salt, an alkyl morpholinium salt, a benzethonium salt or an ethoxylated quaternary ammonium salt or mixtures thereof.
• the salt is a quaternary ammonium salt, it is selected from the group of monoalkyl trimethyl ammonium salts, dialkyl dimethyl ammonium salts and monoalkyl monobenzyl dimethyl ammonium salts.
• the cationic surfactant is a quaternary cationic surfactant and more preferably a quaternary ammonium surfactant.
• the cationic surfactant is selected from the group of benzethonium, benzalkonium, dimethyldialkylonium, alkylpyridinium and alkyltrimethylammonium cations with any counter ion, for example: bromide, chloride, acetate or methyl sulphate.
• the quaternary cationic surfactant is present at a level of more than or equal to 0.025% by weight, more preferably from 0.05% to 4% by weight and more preferably from 0.1% to 2% by weight.
• the dressing preferably comprises a metal chelating agent, for example a citrate or polyphosphate or ethylenediaminetetra-acetic acid (EDTA).
• EDTA is preferably present as the di-, tri- or tetra-basic salts of EDTA. We have found that these salts enhance the antimicrobial effect of the ionic metal in disrupting biofilm.
• the pH of the composition is preferably between 4 and 8, more preferably between 4 and 6 and most preferably between 4.5 and 5.5.
• the desired pH may be achieved by incorporating buffering agents in the composition.
• buffering agents which may be included are citric acid/di-sodium hydrogen phosphate, citric acid/sodium citrate, acetic acid/sodium acetate.
• the buffering agent may conveniently be present in an amount of about 0.5% to 2% by weight of the composition so as to provide an isotonic composition.
• the antimicrobial compositions may be in the form of a solution which can be used as a spray to be applied to the dressing or a solution dip into which the dressing can be immersed.
• the pH of the formulation is buffered at around 5.5 as this does not alter the pH balance of the peri-wound tissue and therefore protects it.
• EDTA is preferably present in the compositions at a level of 0.1% to 4% by weight of the composition, more preferably less than 2% by weight, more preferably 0.2 to 1% by weight.
• the dressings according to the invention can be made by modifying cellulosic fibres for instance by the methods described in EP 0616650 or WO 2012/061225 to obtain a fibre which is capable of gelling on the absorption of exudate from the wound.
• the antimicrobial metallic ion can then be added to the fibres by an ion exchange process in a largely organic solvent followed by washing in an aqueous organic solution which also comprises an optional salt for photostabilising the metallic ion if appropriate and the optional metal chelating agent.
• the fibre is then washed again in an organic solvent wash and warm air dried.
• the fibre can then be processed to form a dressing by conventional means.
• the optional photostabilising agent can be added as described in EP1343510.
• the moisture content of the dressing is between 10% and 20%.
• the moisture content of the dressing is between 11% and 18%, more preferably it is between 11.5% and 15% by weight and most preferably it is between 11.5 and 13% by weight.
• the moisture content of dressing is at least 10% or at least 10.5%, 11%, 11.5%, 12%, 12.5%, 13%, 13.5%, 14%, 14.5% or 15%.
• a moisture content of 12% or 12.5% is particularly preferred.
• the moisture content of the dressing may, amongst other techniques, be measured indirectly by measuring conductivity of the resulting wound dressing. In other embodiments, the moisture content of the dressing may be measured by measuring the loss on drying of the manufactured dressing.
• the moisture content may be measured by titration techniques (Karl Fischer) which is done by solvent extraction of the water in the dressing or by oven heating followed by water capture by solvent chemicals.
• the method of measuring moisture content in a dressing is not limited to the above, but may be accomplished using other techniques and/or by other technologies known in the field.
• the moisture content of the dressings provided herein may be maintained by controlling environmental conditions during manufacturing.
• cleanrooms may be employed during manufacturing controlling several environmental factors, including air pressure, air flow (including directional flow), air quality (including filtration) and humidity (including room temperature and pressure). All of these environmental factors may contribute to the establishment of the required moisture content of the dressings as disclosed herein.
• temperature control is typically maintained at 18° C., +2° C., preferably +1° C.
• Relative humidity is typically maintained at pre-determined levels, including at least at 50% RH, 55% RH, 60% RH, 65% RH, 70% RH, 75% RH, 80% RH, 85% RH +5% RH, and preferably at +3% RH, depending upon the moisture content of the fibre being processed. These environmental factors may also be adjusted against each other in order to achieve the moisture content desired as disclosed herein.
• dressings that are further processed (for example, textiled or conditioned) and/or stored are first packaged in moisture impermeable packaging material or film and sealed prior to movement or storage of the dressings.
• moisture-impermeable packaging material include polyethylene, aluminium, polyester, mixtures thereof or any other suitable material or mixtures thereof, including a trilaminate film of polyethylene, aluminium foil and a polyester that ensures protection from light, oxygen and moisture transmission.
• the improvement in usability of wound dressings comprising surfactants as described herein results in the substantial maintenance of conformability as compared to a wound dressing without surfactant present.
• the improvement in usability of wound dressings comprising surfactants as described herein results in a measurable improvement in tensile strength as compared to wound dressings with a moisture content of less than 10%.
• the improvement in usability of wound dressings comprising surfactants as described herein results in a measurable improvement in tensile strength as compared to wound dressings stored at ambient temperature or in zero humidity conditions.
• the improvement in usability of wound dressings comprising surfactants as described herein results in the substantial maintenance of wound dressing structure, including lack of dust formation, as compared to wound dressings stored at ambient temperature or in zero humidity conditions.
• Dressings according to the invention were prepared modification of solvent spun cellulose tow to a degree of substitution of 0.3 to form carboxymethylcellulose, neutralising to a pH of 5.5 with an organic acid. Adding 1.2% cationic silver by an ion exchange process in a largely organic solvent such as by the process described in EP1343510, washing in an aqueous organic solution containing sodium chloride and di-sodium EDTA for light stabilisation and to entrain approximately 0.4% EDTA. Followinged by washing in organic solvent wash containing fibre finishing agents including tween 20 and benzethonium chloride (to give 0.135% benzethonium chloride on the finished product). Warm air drying, cutting to staple and processing into a nonwoven felt by carding and a needle punching process. The dressings were cut to size from the felt and packaged in a light, moisture and vapour impermeable heat sealed foil pouch.
• the dressings were removed from the packs and then subjected to various controlled environments.
• Samples were tested immediately after opening the packs. Samples removed from the other environments were sealed into plastic bags during removal, and then tested immediately. The plastic bags (also preconditioned in corresponding controlled environments) were used to maintain the humidity of the environment of the samples until the point of testing.
• LOD of the samples was determined using the Ohaus moisture balance MB23 operated in accordance with the instruction manual. A sample mass of greater than 1 gram was used. Samples were cut to fit within the weighing pan, ensuring there was adequate clearance from the heating element. A standardised method was used with a maximum temperature limit of 110° C. The endpoint was determined automatically when the sample mass stopped reducing and was stable. Under these conditions the fabric did not char. Typically, samples would be subjected to a 10 minute cycle.
• 2.5 cm ⁇ 7.5 cm rectangular strips were cut from along the length (machine direction) and across the width (transverse direction) using a ribbon cutting die and press. Samples were conditioned as described in the table. The peak force and the extension at which that force occurred were recorded when a 50 mm test length was stretched at a constant separation rate of 100 mm per minute.
• Loss on drying is the summation of all the volatile substances that can be removed by heating at 110° C. These include ethanol, water and to some degree acetic acid.
• fibres for use in wound dressings according to the invention can be successfully textiled between 42% and 50% RH at around 18 to 20° C.
• Trials suggest that fibres with 10.5% to 11.5% w/w moisture content can be carded efficiently.
• AQUACEL Ag commercial product, absorbent, gelling, fibrous-felt dressing containing 1.2% w/w ionic silver.
• AQUACEL Ag treated with an antimicrobial composition comprising di-sodium EDTA and benzethonium chloride during the addition of silver to the fibres.
• AQUACEL Ag according to the invention that is those treated with an antimicrobial composition comprising di-sodium EDTA and benzethonium chloride were produced by the method of example 1.
• the resulting dressings were conditioned in a laboratory environment maintained at an average temperature of 20° C. ⁇ 2° C. and an average relative humidity of 65% RH ⁇ 4% for at least 24 hours prior to testing.
• the dressings had a moisture content as shown below.
• the AQUACEL Ag dressings were similarly conditioned and packaged.
• Dressing conformability was assessed using a panel of three laboratory staff who were given six samples each of the dressing according to the invention and correspondingly sized AQUACEL Ag as a comparator (or control). They wrapped each dressing around their forearm (in the dry state directly from the packaging) and scored how well each dressing conformed to the shape of the arm using a comparative score based on a five point system.

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• 2013
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