CA2265835C - Moisture-regulating adhesive dressing - Google Patents

Moisture-regulating adhesive dressing Download PDF

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Publication number
CA2265835C
CA2265835C CA002265835A CA2265835A CA2265835C CA 2265835 C CA2265835 C CA 2265835C CA 002265835 A CA002265835 A CA 002265835A CA 2265835 A CA2265835 A CA 2265835A CA 2265835 C CA2265835 C CA 2265835C
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Canada
Prior art keywords
adhesive
adhesive dressing
transmission rate
vapor transmission
moisture vapor
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Expired - Fee Related
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CA002265835A
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French (fr)
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CA2265835A1 (en
Inventor
Steven B. Heinecke
Donald H. Lucast
John T. Capecchi
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3M Co
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Minnesota Mining and Manufacturing Co
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Publication of CA2265835A1 publication Critical patent/CA2265835A1/en
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F13/00—Bandages or dressings; Absorbent pads
    • A61F13/02—Adhesive plasters or dressings
    • A61F13/023—Adhesive plasters or dressings wound covering film layers without a fluid handling layer

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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Vascular Medicine (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)
  • Laminated Bodies (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

An adhesive dressing includes an adhesive composition in the form of a substantially continuous layer on at least a portion of a conformable backing in which the adhesive composition and the backing are selected such that the adhesive dressing has an Inverted Buffered Saline Moisture Vapor Transmission Rate of at least about 9000 g/m2/24 hrs.

Description

l0152025CA 02265835 2005-10-2760557—607lMOISTURE-REGULATING ADHESIVE DRESSINGBackground of the InventionThe invention relates to regulating the amount ofmoisture associated with a wound site during the healingpIOC€SS.Wound dressings are designed to adhere to apatient’s skin in order to protect an underlying woundduring the healing process. To be effective, such dressingsmust conform and adhere to moist skin without sticking toIn addition,the wound surface. such dressings must controlthe amount of moisture associated with the wound site.Summary of the InventionThe invention features an adhesive dressing thatincludes an adhesive composition in the form of asubstantially continuous layer on at least a portion of aconformable backing in which the adhesive composition andthe backing are selected such that said adhesive dressinghas an Inverted Buffered Saline Moisture Vapor TransmissionRate of at least about 9000 g/mg/24 hrs.According to one aspect of the present invention,there is provided an adhesive dressing comprising anadhesive composition in the form of a substantiallycontinuous layer on at least a portion of a conformablebacking consisting of a single layer of material, whereinsaid adhesive composition comprises the reaction product of:(a) an acrylic or methacrylic acid ester of a non—tertiaryalcohol having between 4 and 14 carbon atoms, inclusive;(b) a hydrophilic, ethylenically unsaturated monomer; and(c) at least 15 parts by weight of an ethylenically_]__l015CA 02265835 2005-10-2760557-6071unsaturated monomer having one or more carboxylic acidgroups, said adhesive composition and said backing beingselected such that said adhesive dressing has an InvertedBuffered Saline Moisture Vapor Transmission Rate of at leastabout 9000 g/m2/24 hrs.In preferred embodiments, the adhesive dressinghas an Inverted Buffered Saline Moisture Vapor TransmissionRate of at least about 10,000 g/mg/24 hrs, more preferably atleast about 12,000 g/mg/24 hrs. Particularly preferred areadhesive dressings having an Inverted Buffered SalineMoisture Vapor Transmission Rate of between about 9000 andabout 16,000 g/m2/24 hrs.The adhesive dressing preferably has an InvertedBuffered Saline Moisture Vapor Transmission Rate that is atleast about four times greater than the Inverted WaterMoisture Vapor Transmission Rate (as measured according toASTM E—96—80). In some1015202530W0 98/15245CA 02265835 1999-03-09PCT/US97/17223preferred embodiments, the adhesive dressing has anInverted Water Moisture Vapor Transmission Rate of nogreater than about 3000 g/m2/24 hrs.A preferred adhesive composition includes thereaction product of: (a) an acrylic or methacrylicacid ester of a non-tertiary alcohol having between 4and 14 carbon atoms, inclusive; (b) a hydrophilic,ethylenically unsaturated monomer; and (c) at least 15parts by weight of an ethylenically unsaturatedmonomer having one or more carboxylic acid groups. By"hydrophilic" it is meant that the monomer has a highaffinity for water. Examples of preferred hydrophilicmonomers include an acrylate or methacrylate—terminated polyalkylene glycol. An example of apreferred ethylenically unsaturated monomer having oneor more carboxylic acid groups is acrylic acid.Examples of preferred acrylic or methacrylic acidesters include iso—octyl acrylate, 2—ethylhexylacrylate, n—butyl acrylate, or a combination thereof.A particularly preferred adhesive compositionincludes the reaction product of iso—octyl acrylate,an acrylate or methacrylate—terminated polyalkyleneglycol, and acrylic acid.The backing preferably includes athermoplastic polyurethane.‘ It preferably has anInverted Buffered Saline Moisture Vapor TransmissionRate of at least about 9000 g/m2/24 hrs. It mayinclude one or more layers of material which may bethe same as, or different from, each other. Moreover,the backing preferably has a wet tensile strength ofat least about 20 x 106 N/m2.The invention provides an adhesive dressinguseful for treating wounds which effectively regulatesthe amount of moisture in contact with the wound-2-1015202530W0 98/15245CA 02265835 1999-03-09PCT/US97/17223underlying the dressing. The moisture vaportransmission rate of the dressing changes in responseto changes in the pH of the body fluids associatedwith the underlying wound. It is thus possible tomaintain a moist environment sufficient to prevent theunderlying wound from dehydrating without creatingpools of liquid that can cause adhesive failure. Thedressing also exhibits a high moisture vaportransmission rate while retaining its structuralintegrity in moist environments. Moreover, the use ofa continuous adhesive composition provides improvedadhesion to skin relative to dressings featuringpatterned adhesive compositions on a backing, andavoids creating channels for fluid leakage.Other features and advantages of the inventionwill be apparent from the following description of thepreferred embodiments thereof, and from the claims.Description of the Preferred EmbodimentsThe adhesive dressings feature an adhesivecomposition provided on a hydrophilic backing in theform of a substantially continuous layer. Thedressings are designed to optimize the moisturecontent of an underlying wound while remaining adheredto skin.The invention was made possible, in part, bythe inventors‘ discovery of a new method for measuringmoisture vapor transmission rate. This method, calledthe Inverted Buffered Saline Moisture VaporTransmission Test, measures moisture vaportransmission rate in a slightly alkaline environment(e.g., about pH 7.2 to 7.4) typical of the environmentassociated with a fresh wound. The method is similarto the Inverted Water Moisture Vapor Transmission Testoften used to measure the moisture vapor transmission_3_1015202530WO 98/15245CA 02265835 1999-03-09PCT/US97/17223properties of films, except that it substitutesThe method thusprovides a good indication of the moisture vaporbuffered saline for deionized water.transmission rate requirements of the wound, therebyproviding the basis for designing dressings designedto meet these requirements.As the wound heals, the pH of the woundenvironment changes. The Inverted Water MoistureVapor Transmission Test provides a good measure of themoisture vapor transmission rate requirements of thewound at neutral pH.Using the Inverted Buffered Saline MoistureVapor Transmission Rate Test and Inverted WaterMoisture Vapor Transmission Rate Test as guides, theoptimum dressings for wound management are those inwhich the adhesive composition and the backing areselected such that the dressing exhibits an InvertedBuffered Saline Moisture Vapor Transmission Rate of atleast about 9,000 g/m2/24 hrs. and an Inverted WaterMoisture Vapor Transmission Rate of no greater thanabout 3,000 g/m2/24 hrs.The backing is a conformable, hydrophilic,polymeric material which has a high moisture vaportransmission rate (as measured according to both theInverted Buffered Saline Moisture Vapor TransmissionRate Test and the Inverted Water Moisture VaporTransmission Rate Test), yet retains its structuralintegrity in a moist environment. Preferably, thebacking has an Inverted Buffered Saline Moisture VaporTransmission Rate of at least about 9,000 g/m2/24 hrs,an Inverted Water Moisture Vapor Transmission Rate ofat least about 9,000 g/m2/24 hrs., and a wet tensilestrength of at least about 20 X 106 N/m2.1015202530W0 98/ 15245CA 02265835 1999-03-09PCT /U S97/ 1 7223The backing may include one or more layers ofmaterial tailored to achieve the above—describedmoisture vapor transmission and structural integrityproperties. Examples of suitable materials includehydrophilic thermoplastic urethanes commerciallyavailable from B.F. Goodrich under the tradedesignation "EstaneTM"including, for example,EstaneTM 58237 and EstaneTM 58245; hydrophilicthermoplastic polyether-amide block copolymerscommercially available from ATOCHEM under the tradedesignation "PEBAX 4011;" and polyether-ester blockcopolymers.The adhesive composition is provided on asurface of the backing in the form of a substantiallycontinuous layer. Preferably, it is in the form of apressure sensitive adhesive. The adhesive compositionis selected such that it cooperates with the backingto yield a dressing having the aforementioned moisturevapor transmission characteristics. Preferably, theadhesive composition is a hydrophilic compositionhaving a sufficiently high concentration of acidicgroups such that it has a moisture vapor transmissionrate that approximates the pH of the wound siteunderlying the dressing, and changes in response tochanges in the pH of the wound site.A preferred adhesive composition is thereaction product of (a) 50 to 80 parts of an acrylicor methacrylic acid ester of a non-tertiary alcoholhaving between 4 and 14 carbon atoms, inclusive; (b)10 to 30 parts by weight of a hydrophilic,ethylenically unsaturated monomer; and (c) at least 15parts by weight (e.g., 15-25 parts by weight) of anethylenically unsaturated monomer having one or morecarboxylic acid groups.1015202530W0 98/ 15245CA 02265835 1999-03-09PCT/US97/ 17223Examples of suitable acrylic and methacrylicacid ester monomers include esters prepared byreaction with alcohols such a l—butanol, 2—butanol, 1-pentanol, 2—pentanol, 3-pentanol, 2—methyl-1—butanol,1-hexanol, 2-hexanol, 2—methyl—1—pentanol, 3-methyl—1—pentanol, 2~ethyl—1-butanol, 3,5,5-trimethyl-1-hexanol, 3—heptanol, 1-octanol, 2-octanol, isooctylalcohol, 2-ethyl—1—hexanol, 1-decanol, 1—dodecanol, 1-tridecanol, 1-tetradecanol, and the like, as well ascombinations thereof. Particularly preferred estermonomers include isooctyl acrylate, 2-ethyl hexylacrylate, and n-butyl acrylate.Examples of suitable ethylenically unsaturatedhydrophilic monomers include free radically reactivehydrophilic oligomers (a polymer having a low numberof repeating units, generally 2 to 20) and/or polymersother suitableethylenically unsaturated hydrophilic monomers includeincluding poly(alkylene oxides).macromonomers, e.g., acrylate—terminated poly(ethyleneoxide), methacrylate—terminated poly(ethylene oxide),methoxy poly(ethylene oxide) methacrylate, butoxypoly(ethylene oxide) methacrylate, p-vinyl benzyl-terminated poly(ethylene oxide), methoxy poly(ethyleneoxide) acrylate, butoxy poly(ethylene oxide) acrylate,poly(ethylene oxide) diacrylate, poly(ethylene oxide)dimethacrylate, and combinations thereof.Particularly preferred ethylenically unsaturatedhydrophilic monomers include acrylate and methacrylateesters prepared from mono-hydroxyl-terminatedpoly(lower alkylene oxides) such as polyethylene andpolypropylene glycols commercially available under theTMutrade designation "Carbowax from Union CarbideCorp. in a variety of molecular weights (e.g.,TM TM TM 750’Carbowax 350, Carbowax 550, Carbowax-6-1015202530CA 02265835 2005-10-2760557-6071CarbowaxTM 2000, and CarbowaxTM 5000). An example ofa preferred acrylate-terminated poly(ethylene glycol)is commercially available from Shin-Nakamura ChemicalCo., Ltd., Japan, under the designation "NK Ester AM-90G."Examples of suitable carboxylic acid-containing monomers include acrylic acid, methacrylicacid, itaconic acid, and combinations thereof. Thepreferred monomer is acrylic acid.other useful materials that can be added tothe adhesive composition include chain transfer agentsfor controlling molecular weight (e.g., carbontetrabromide, mercaptans, or alcohols), tackifiers,plasticizers (e.g., polyethylene glycol, polypropyleneglycol, or glycerin), perfumes, deodorants,antioxidants, and pharmacologically active ingredientssuch as drugs, antibiotics, and anti-microbial agents.The chain transfer agents are added to the monomermixture. The other materials can be added to themonomer mixture or to the polymerized composition.The adhesive compositions can be preparedaccording to a variety of well-known polymerizationtechniques, including solution, emulsion, and bulkpolymerization (e.g., actinic radiation-initiatedpolymerization as described in Martens et al., U.S.Patent No. 4,181,752. They may be used alone orblended with discrete, crosslinked polymermicrospheres as described in U.S. Patent No. 6,479,073.The microspheres are prepared via a freeradical suspension polymerization process. They may1015202530W0 98/15245CA 02265835 1999-03-09PCT/U S97/ 17223be solid or hollow, and either tacky or tack—free.The tack-free microspheres can be elastomeric orplastic. The microspheres typically have diametersranging from about 1 micrometer to about 300micrometers. The amount of microspheres preferably isbetween about 1% and about 75% by volume, and isselected to yield a blend having a substantiallysmooth, exposed surface available for adhesion afterapplying the adhesive composition to the backing.The invention will now be described further byway of the following examples.EXAMPLESTest ProceduresInverted Water Moisture Vapor TransmissionRateThe moisture vapor transmission rate wasmeasured according to ASTM E—96—8O using a modifiedPayne cup method. Specifically, a 35 mm diametersample of 1 mil (0.025 mm) thick material to be testedcontaining no perforations was cut. The sample wasplaced between adhesive—containing surfaces of twofoil adhesive rings, each having a one inch (2.54 cm)diameter hole. The holes of each ring were carefullyaligned. Finger pressure was used to form afoil/sample/foil assembly that was flat, wrinkle—free,and had no void areas in the exposed sample.A 4 oz. (0.14 kg) glass jar was filled half-way with distilled water. The jar was fitted with ascrew—on cap having a 1.50 inch (3.8 cm) diameter holein the center thereof and with a 1.75 inch (4.45 cm)diameter rubber washer having a 1.12 inch (2.84 cm)diameter hole in its center. The rubber washer wasplaced on the lip of the jar and the foil/sampleassembly was placed on the rubber washer. The lid was._8..1015202530W0 98/15245CA 02265835 1999-03-09PCTIUS97l17223then screwed loosely on the jar.The assembly was placed in a chamber at 100°F(38°C) and 20% relative humidity for four hours. Thecap was tightened inside the chamber so that thesample was level with the cap (no bulging) and therubber washer was in proper seating position.At the end of four hours, the foil/sampleassembly was removed from the chamber and weighedimmediately to the nearest 0.01 gram (initial weightW1). The assembly was then returned to the chamberfor at least 18 hours, after which it was removed andweighed immediately to the nearest 0.01 gram (finalweight W2). The moisture vapor transmission rate(MVTR) in grams of water vapor transmitted per squaremeter of sample area in 24 hours was calculatedaccording to the following formula (where "T" refersto exposure time in hours):MVTR = (wl - W2) (4.74 x 104)/TThree measurements of each sample were made,and the average value taken. The MVTR values arereported in Table 1 in g/m2/24 hrs.Inverted Buffered Saline Moisture Vapor TransmissionEggThe procedure is the same as the InvertedWater Moisture Vapor Transmission Rate Test exceptthat phosphate—buffered saline is substituted fordistilled water. The MVTR values are reported inTable 1 in g/m2/24 hours.Example 1An adhesive composition featuring a pressuresensitive adhesive matrix blended with polymericmicrospheres was prepared as follows.1015202530CA 02265835 2005-10-2760557-6071To prepare the microspheres, a monomer mixturewas prepared by dissolving 4.8 g of acrylic acid, 2.4giof CarbowaxTM 750 acrylate (polyethylene oxideacrylate) and 1.13 g LucidolTM-70 (70% benzoylperoxide) in 232.8 g of iso-octyl acrylate. Asurfactant solution was prepared by dissolving 0.75 gof sodium dodecyl benzene sulfonate in 360 g of water.The monomer mixture was then added to the surfactantsolution, and the resulting mixture emulsified using aGifford-WoodTM mixer until the droplet size was lessthan 5 micrometers. The emulsion was charged to a 1liter baffled reactor, heated to 65°C, degassed withN2, and allowed to react for 8 hours. Microsphereshaving an average diameter of about 2 micrometers wereformed during the reaction period.The adhesive matrix was prepared according tothe procedures described generally in.PCT US84/00506and WP 84/03837 using a monomer mixture containing 70parts by weight'isooctyl acrylate, 15 parts by weightacrylic acid, and 15 parts by weight CarbowaxTM 750acrylate (polyethylene oxide acrylate). The matrixwas then blended with the microspheres (30microspheres per hundred parts matrix) using aLightening—brand mixer and applied to a release linermade of silicone-coated kraft paper.Next, a 25 micrometer thick film of EstaneT“58237 thermoplastic polyurethane (B.F. Goodrich Co.)was extruded and laminated to the adhesiveThe thickness of the adhesivecomposition was 25 microns (1 mil).composition.. A dressing wasprepared according to the procedure described inExample 1 of Heinecke et al., U.S. 5,531,855to provide a frame delivery101520CA 02265835 2005-10-2760557-6071system of 6 cm x 7 cm or 10 cm x 12 cm.The moisture vapor transmission properties ofthe dressing were measured and are reported in Table1.Example 2The procedure of Example 1 was followed exceptthat the adhesive composition did not contain anymicrospheres. The moisture vapor transmissionproperties of the dressing were measured and arereported in Table 1.Example 3The procedure of Example 1 was followed exceptthat the matrix was prepared from a monomer mixturecontaining 60 parts isooctyl acrylate, 20 parts byweight acrylic acid, and 20 parts by weight CarbowaxTM750 acrylate (polyethylene oxide acrylate). Themoisture vapor transmission properties of the dressingwere measured and are reported in Table 1.TABLE 1MOISTURE VAPOR TRANSMISSION RATE (G/M2/24 HRS)EXAMPLE INVERTED WATER INVERTEDMVTR BUFFERED SALINEMVTR1 1540 16,0002 1200 9,1003 2800 11,000ESTANE 58237* 16,000 16,000* EstaneTM 58237 polyurethane backing (25 micrometerthickness) without any adhesive composition.

Claims (9)

CLAIMS:
1. An adhesive dressing comprising an adhesive composition in the form of a substantially continuous layer on at least a portion of a conformable backing consisting of a single layer of material, wherein said adhesive composition comprises the reaction product of:
(a) an acrylic or methacrylic acid ester of a non-tertiary alcohol having between 4 and 14 carbon atoms, inclusive;
(b) a hydrophilic, ethylenically unsaturated monomer; and (c) at least 15 parts by weight of an ethylenically unsaturated monomer having one or more carboxylic acid groups, said adhesive composition and said backing being selected such that said adhesive dressing has an Inverted Buffered Saline Moisture Vapor Transmission Rate of at least about 9000 g/m2/24 hrs.
2. The adhesive dressing of claim 1, wherein said adhesive dressing has an Inverted Buffered Saline Moisture Vapor Transmission Rate of at least about 10,000 g/m2/24 hrs.
3. The adhesive dressing of claim 1, wherein said adhesive dressing has an Inverted Buffered Saline Moisture Vapor Transmission Rate of at least about 12,000 g/m2/24 hrs.
4. The adhesive dressing of claim 1, wherein said adhesive dressing has an Inverted Buffered Saline Moisture Vapor Transmission Rate of between about 9,000 and about 16,000 g/m2/24 hrs.
5. The adhesive dressing of claim 1, wherein said adhesive dressing has an Inverted Water Moisture Vapor Transmission Rate of no greater than about 3,000 g/m2/24 hrs.
6. The adhesive dressing of claim 1, wherein said dressing has an Inverted Buffered Saline Moisture Vapor Transmission Rate that is at least about four times greater than the Inverted Water Moisture Vapor Transmission Rate.
7. The adhesive dressing of claim 1, wherein said backing comprises a thermoplastic polyurethane.
8. The adhesive dressing of claim 1, wherein said backing has an Inverted Buffered Saline Moisture Vapor Transmission Rate of at least about 9000 g/m2/24 hrs.
9. The adhesive dressing of claim 1, wherein said backing has a wet tensile strength of at least about 20 × 10 6N/m2.
CA002265835A 1996-10-07 1997-09-25 Moisture-regulating adhesive dressing Expired - Fee Related CA2265835C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US08/726,510 US5849325A (en) 1996-10-07 1996-10-07 Moisture-regulating adhesive dressing
US08/726510 1996-10-07
PCT/US1997/017223 WO1998015245A1 (en) 1996-10-07 1997-09-25 Moisture-regulating adhesive dressing

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CA2265835A1 CA2265835A1 (en) 1998-04-16
CA2265835C true CA2265835C (en) 2006-12-12

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US (1) US5849325A (en)
EP (1) EP0934042B1 (en)
JP (1) JP4344864B2 (en)
AU (1) AU4501997A (en)
CA (1) CA2265835C (en)
DE (1) DE69718035T2 (en)
WO (1) WO1998015245A1 (en)

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EP0934042B1 (en) 2002-12-18
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WO1998015245A1 (en) 1998-04-16
JP2001525689A (en) 2001-12-11
CA2265835A1 (en) 1998-04-16
US5849325A (en) 1998-12-15
DE69718035T2 (en) 2003-09-25
JP4344864B2 (en) 2009-10-14
AU4501997A (en) 1998-05-05

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