US2804073A - Fluid surgical dressing - Google Patents

Fluid surgical dressing Download PDF

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Publication number
US2804073A
US2804073A US333366A US33336653A US2804073A US 2804073 A US2804073 A US 2804073A US 333366 A US333366 A US 333366A US 33336653 A US33336653 A US 33336653A US 2804073 A US2804073 A US 2804073A
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Prior art keywords
film
dressing
skin
adhesive
former
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US333366A
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William F Gallienne
May William E Le
Pereny Louis
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PROTECTIVE TEATMENTS Inc
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PROTECTIVE TEATMENTS Inc
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    • 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
    • A61L26/0014—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S424/00—Drug, bio-affecting and body treating compositions
    • Y10S424/13—Burn treatment
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S602/00—Surgery: splint, brace, or bandage
    • Y10S602/904—Film-forming bandage material

Definitions

  • This invention relates to a surgical dressing for wounds, burns and the like and, more particularly, to a transparent releasably adhesive dressing adapted to be applied as a liquid or spray.
  • a surgical dressing in the form of a tough, elastic, transparent film with mildly bacteriostatic properties.
  • the film is non toxic, chemically inert, insoluble in body fluids; it is resistant to water while being sufficiently permeable to moisture vapor to prevent formation of blisters thereunder.
  • the transparent film dressing includes an adhesive component providing controllable adhesion such that it adheres to normal skin sufficiently to anchor the film firmly yet be readily peelable for removal, and has little if any adhesion to raw flesh of an open wound or burned area or to newly formed skin beneath the dressing.
  • this dressing is stable, impermeable to coliform group organisms, sterile, and adapted to be applied by wiping on, brushing and in theform of a spray. It is of such character that laymen Without medical training can apply the dressing so as to form an artificial skin over a wound or burn to stabilize the injured area and protect it until further medical treatment is obtained.
  • a further object of this invention is to provide in liquid composition a film forming component, a controlled adhesion producer, a plasticizer, and a bacteriostatic agent in a nontoxic vehicle for application to form a dressing of the character described.
  • Still another object of. this invention is to provide a liquid composition of the character described including a controlled adhesion producing component, separate from the film forming component, which forms releasable adhesion to normal skin without adhering to the injured area.
  • Another object of this invention is to provide a liquid composition of the character described which upon drying forms a tough, elastic film over a wound sufliciently permeable to permit outward moisture vapor transmission from the wound while being substantially impermeable to the inward passage of infection promoting organ- 1sms.
  • Still a further object of this invention is to provide a liquid composition of the character described which upon drying produces over a wound a transparent elastic film adherent to normal skin, nonadherent to raw flesh, and peelable from normal skin without softening or other treatment.
  • Still another object of this invention is to provide a liquid composition of the character described for application to human skin and injured areas thereof, with the composition having a toxicity or allergic reactivity level at least as low as conventional surgical dressing adhesives, and being substantially free of medication.
  • a further object of this invention is to provide a solvent or dispersion vehicle adapted to admit of application of a tough, elastic, transparent film dressing of the character described and of low smarting, nonirritating and nontoxic physiological effect on exposed tissue in open wounds, burns, and the like.
  • a sterile dressing may be of controlling importance particularly to prevent loss of body fluids and continued exposure of the injured area to bacteria and other sources of infection.
  • the loss of serum from the burned area is an important source of shock and perhaps fatality.
  • emergency treatment adapted for safe application by essentially untrained personnel.
  • a human being has suifered 50% body burns, it has been found that it may require a trained doctor and nurse over an hour to apply a standard ointment and pressure bandage consisting of several pounds ofointment and perhaps yards of bandage to provide emergency treatment.
  • the same burned area could be satisfactorily treated in ,about five minutes by two laymen using but four spray infection occasioned by repeated removals of the dressing to inspect the wound.
  • a sprayable plastic composition is produced which will form upon application a transparent film over the injured area.
  • the film in addition to being transparent, is water-resistant and insoluble in body fluids.
  • it is sufiiciently semipermeable to admit of the outward penetration of water vapor to preclude the formation of a water blister under the dressing when perspiration and/ or other body fluids collect.
  • Such semipermeability does not destroy the cgntinuity of the film nor render it permeable to the inward passage of objectionable bacteria, and is essentially a controlled degree of moisture-vapor transmission as opposed to mechanical porosity.
  • the film is also, when applied sufficiently adhesive to normal skin surrounding the injured area to maintain itself in position, yet readily removable by peeling without softening or other treatment.
  • the film has, however, very limited if any adhesiveness for the exposed raw flesh of the injured area, and is of such character as to avoid adhesion to newly formed skin growing under the dressing. That is, compositions according to this invention exhibit selective adhesion to dry instead of wet skin or flesh.
  • Both the final dressing and its sprayable liquid original composition are relatively nontoxic to either normal skin or the injured area and exhibit low allergic reactivity.
  • the allergic reactivity level is less than that of medically accepted commercial surgical adhesive tape.
  • the solvent or vehicle utilized preferably has a relatively low smarting level and is of such character aswill not promote flow of blood or other body fluids.
  • the sprayable dressing For application of the sprayable dressing by essentially untrained personnel, it includes substantially no medication, although it preferably includes components to maintain sterility or a bacteriostatic condition-i. e., it stabilizes and maintains existing conditions in the injured area preceding or following suitable professional medical treatent.
  • the original liquid composition before application is substantially stable and nonoxidizing for convenient storage and maintains its own sterility and/or includes components which discourage the existence of obnoxious bacteria. Because of the selective or controlled adhesion to dry or healthy skin without adhesion to raw flesh and because of the insolubility of film components in body fluids there is substantially no transfer of film components into the Wound or to newly formed skin beneath the bandage.
  • a sprayable surgical dressing having the attributes noted has been produced according to this invention bythe combination of a film former, an adhesion producer, a plasticizer, and a bacteriostatic agent, which components are admixed to form, with a suitable vehicle, a liquid solution or emulsion.
  • the liquid compositions according to this invention are stable to exposure to temperatures ranging from 65 F. to +165 F. in storage and are usable at temperatures ranging from 20 F. up to 130 F.
  • the smarting level in contact with raw fiesh may be lower than when volatile organic solvents are used, although a solution of the liquid compositions may be readily post-emulsified to decrease the smarting effect if desired.
  • the drying time of the film can be easily controlled, and is usually of the order of five minutes, while with application of the dressing in the form of a Water emulsion, this time may be increased if desired to about fifteen minutes or more.
  • the film former may be present in the proportion of about 100 parts by weight; the adhesion producer in from 5 to 80 parts by weight with approximately 50 parts being preferred; the plasticizer in up to 80 parts by weight with approximately 50 being preferred; and the bacteriostatic agent in up to 2 parts by Weight with approximately .25 being preferred.
  • the bacteriostatic agent may be present as a part of the adhesion producing component. Sufficient nontoxic and volatile solvent is incorporated to produce the desired consistency with about 800 parts being preferred. 7
  • Such a composition is packed in metal containers or so-called aerosol spray-type containers accompanied by suitable well-known spray propellants such as halogenatedaliphatic type or compressed gaseous type propellants if application is desired by aerosol spray. It may also be applied by compressed gas spray, brushing, flowing, wiping on, or dipping.
  • suitable well-known spray propellants such as halogenatedaliphatic type or compressed gaseous type propellants if application is desired by aerosol spray. It may also be applied by compressed gas spray, brushing, flowing, wiping on, or dipping.
  • the film forming component may be of the class consisting of vinyl polymers (including vinyl chloride-vinylidine component copolymers, vinyl chloride-vinyl acetate copolymers and carboxylated or hydroxylated modifications of such copolymers, vinyl chloride-butadiene polymers, vinyl butyral polymers, vinyl acetate polymers, etc.), polyacrylic and polymethacrylic esters and polymers, cellulose acetate butyrate, ethyl cellulose, and compatible combinations thereof.
  • vinyl polymers including vinyl chloride-vinylidine component copolymers, vinyl chloride-vinyl acetate copolymers and carboxylated or hydroxylated modifications of such copolymers, vinyl chloride-butadiene polymers, vinyl butyral polymers, vinyl acetate polymers, etc.
  • polyacrylic and polymethacrylic esters and polymers cellulose acetate butyrate, ethyl cellulose, and compatible combinations thereof.
  • the adhesion producing component may be one or compatible combinations of such resins as glycerol phthalate, abietic acid-glycerol and organic acid and/or phenol modifications of such abietic acid glycerol, amine-aldehyde resins, and resins containing maleic anhydride or phenols (including cresols).
  • resins as glycerol phthalate, abietic acid-glycerol and organic acid and/or phenol modifications of such abietic acid glycerol, amine-aldehyde resins, and resins containing maleic anhydride or phenols (including cresols).
  • the plasticizer may be one or a combination of such monomeric substances as dioctyl phthalate, butyl phthallyl butyl glycollate, di-2(ethyl-hexyl) azelate, acetylated castor oil, phthalic anhydride-vegetable oil derivatives, tricresyl phosphate, o.- and p.-toluene sulfonamides; or polymeric substances such as chlorinated paratfin, cumarone-indene, sebacic acid polymers, treated raw oiticia and other vegetable oils (treated to produce compatibility with film formers).
  • the bacteriostatic agent may satisfactorily be maleic anhydride (as included, for example, in the adhesive component), phenols (including cresols), and compatible physiologically appropriate mercury compounds.
  • Satisfactory volatile solvents for the above include one or a combination of such solvents as organic esters (e. g., ethyl acetate), ketones (e. g. acetone), organic ethers or oxides (e. g. ethylene oxide), aromatic hydrocarbons (e. g., toluene), or chlorinated aliphatic hydrocarbons (e. g., methylene chloride).
  • organic esters e. g., ethyl acetate
  • ketones e. g. acetone
  • organic ethers or oxides e. g. ethylene oxide
  • aromatic hydrocarbons e. g., toluene
  • chlorinated aliphatic hydrocarbons e. g., methylene chloride
  • the solvent component is chosen to produce the desired drying rate and viscosity of liquid composition with regard to method of application, ease of storage, traumatic smarting effect, etc.
  • such a solution may be post-e
  • a satisfactory method of preparation of the composition includes adding the film former slowly to the solvent with agitation in a suitable covered container taking care to avoid agglomeration. The remaining ingredients are added upon the complete solution of the film former and agitation is continued until all ingredients are dissolved. After suitable filtration to remove any suspended foreign matter, the liquid composition is packed into aerosol spray containers at approximately 0 F. in known manner, or otherwise packaged as desired.
  • Example 1 Parts by weight Hydroxylated vinyl acetate-vinyl chloride co-polymer 100 Maleic anhydride modified, glycerol-abietic-Vacid resin 50 Sebacic acid co-polymer type plasticizer 50 Ethyl acetate 600 GP acetone 200
  • Example 2 N-butyl methacrylate polymer 120 Butyl phthalyl butyl glycollate 30 Phenol-modified glycerol-abietic-acid resin 50 Ethyl acetate 800
  • Example 3 Ethyl cellulose Di-octyl phthalate 80
  • Example 4 Vinyl chloride-vinyl acetate resin VAGH Paraplex G-SO (proprietary epoxidated-oil type plasticizer) 50 Amberlac D-96 (maleic anhydride modified glycerolabietic-acid resin) 50 Ethyl acetate 800 In
  • volatile chlorinated solvents have no deleterious effect on dried film properties when added to the liquid composition in the range of one volume of composition to two volumes of solvent.
  • concentration of plasticizer may also be varied to produce the desired flexibility or softness indicated by the requirements of use.
  • the above noted maleic anhydride modified resin includes the bacteriostatic component because of its fungistatic and bacteriostatic properties and the proportions may be varied to a limited extent to produce the desired hardness, adhesiveness and flexibility suited for a particular application.
  • a suitable composition of the aqueous emulsion type embodying this invention includes a film forming component in the form of a latex oremulsion on a 50% nonvolatile basis in the range of approximately 200 parts by weight, a separate adhesion producer up to 80 parts by weight with 5 parts being preferred, a plasticizer up to 80 parts by weight with 1 part being preferred, a bacteriostatic agent up to 2 parts by weight with .25 being preferred (may be included with adhesion producer), and volatile solvents up to 20 parts by weight with 5 being preferred.
  • the above composition is emulsified with a suitable emulsifying agent, a protective colloid and thickener if desired, and an anti-foaming agent to give an emulsion of desired consistency depending upon application requirements. For the above ranges approximately 450 parts of water is preferred.
  • the film forming component in the form of an aqueous emulsion or latex, may be any of those substances noted above, although it has been found that cellulose acetate butyrate and ethyl cellulose are more appropriate for solvent type application than for the emulsion type.
  • the adhesion producer can be any of those listed above and the plasticizing and bacteriostatic components include those mentioned for the solution type composition.
  • Appropriate solvents include alcohols as well as the solvents listed above. Satisfactory emulsifying agents are selected from commercially available non-ionic, anionic or cationic surface active agents depending upon the selection of the film former latex and compatibility therewith as well as the ability to form a stable emulsion with the selected adhesive component.
  • the protective colloid added is selected from such substances as methyl cellulose, carboxymethyl cellulose, polyvinyl alcohol, solubilized protein, etc., of such grades as will produce the desired viscosity in the completed composition depending upon the requirements of method of application and use.
  • the latex or film former is usually commercially available as an emulsion.
  • a second emulsion is made by dissolving the adhesion producing component, bacteriostatic agent and plasticizer in the least quantity of volatile solvent which will form a complete solution. It has been found that this usually results in a concentration of approximately 50% nonvolatiles.
  • the emulsifying agent and anti-foaming agent are added to this solution and stirred until well dispersed. With vigorous agitation, sufficient water is added to produce the desired emulsion containing approximately 25% nonvolatiles.
  • emulsion type 200 parts of film former latex are placed into a stainless steel mixing tank and then the 25% adhesion producer emulsion is slowly added thereto with good but not too vigorous agitation. Sufficient water is then added to reduce the nonvolatile content of the mixture to approximately 15% to 25% as desired. Finally sufficient amount of a solution of 3 parts methyl cellulose in 97 parts of cool water is added to produce the desired viscosity and stability. It will be noted that the proportion of volatile solvents used in this composition is purposely kept low to minimize the smarting action of the composition upon first contacting raw flesh.
  • liquid compositions embodying this invention are also readily controlled.
  • the emulsion type noted above is essentially noninflammable and a solution type comprising a vinyl copolymer film former, an amine-aldehyde adhesive and a phosphate-ester plasticizer all dissolved in methylene chloride exhibits a very low degree of inflammability.
  • Either the solution type or the emulsion type of composition will produce upon drying a satisfactory dressing of the character described.
  • the absence or low degree of medication indicates complete safety in the use of such dressing by substantially untrained laymen.
  • the plastic film produced after evaporation of either the volatile solvents or the aqueous emulsion is tough, elastic, transparent, and of controlled adhesiveness to normal skin.
  • the film is water resistant and the extractability of components thereof by water or body fluids is virtually negligible.
  • the composition is sterile and bacteriostatic, it need not include bactericidal agents or other medication.
  • the liquid compositions produced are stable and nonoxidizing and, if spray application is desired, are of sufficiently low viscosity. Storage problems are minimized since, except as desired to control evaporation of solvent, there is no need for air tight or other pressure type containers for storage.
  • the film, after application can be peeled away from normal skin Without softening or other treatment and without a further application of solvent or water.
  • the film upon application exhibits substantially no adhesiveness for raw flesh and, after drying, no adhesiveness for newly formed skin growing under the dressing so that disturbance of the healing wound or other trauma is virtually non-existent upon removal of the dressing.
  • the fihn While the fihn is water resistant and impermeable to coliform organisms, it is semipermeable to water vapor which might otherwise collect beneath the applied dressing and form either blisters or channels through the dressing to the outside leaving entranceways for obnoxious infection producing material. Accordingly, with the dressing applied, healing therebeneath proceeds under essentially anaerobic conditions.
  • the film formers utilized when applied according to this invention, produce uniform and substantially bubble-free films free of accidental gas channels or infection admitting openings. Since the dried film is substantially resistant to passage of medicaments therethrough, it may be used to protect selected skin areas from medications desired to be applied only to other areas of the body.
  • a liquid dressing for application to skin to provide upon drying an elastic semipermeable self-sustaining peel-able film dressing for wounds, burns and incisions comprising a volatile liquid vehicle for said dressing, a film-former providing upon drying a semipermeable elastic film for controlled outward moisture vapor transmission and substantial impermeability to bacteria and selected from the class consisting of vinyl polymers, including polyacrylic and polymethacrylic ester polymers, cellulose acetate butyrate, ethyl cellulose, and compatible combinations thereof, a synthetic resinous adhesive compatible with said film-former for adhering said film dressing to normal skin but being substantially nonadherent to raw flesh, the cohesive strength of said film dressing being greater than the adhesive strength of said adhesive for peelable removability of said film dressingfrom skin to which it is applied, and a plasticizer for said filmformer and said adhesive effecting in said film dressing controlled flexibility and elasticity thereof for conforming to movements and contours of skin to which it is applied, said film-former and adhesive and plasticizer all being homo
  • a liquid dressing for application to skin to provide upon drying an elastic semipermeable self-sustaining peelable transparent film dressing for wounds, burns and incisions comprising a non-irritating volatile liquid vehicle for said dressing, a synthetic resinous elastomeric film-former providing upon drying a semipermeable elastic film for controlled outward moisture vapor transmission and substantial impermeability to bacteria and selected from the class consisting of vinyl polymers, including polyacrylic and polymethacrylic ester polymers,
  • a liquid dressing for application to skin to provide upon drying an elastic semipermeable self-sustaining peelable transparent film dressing for wounds, burns and incisions comprising a major proportion of volatile solvent for said dressing, a resin film-former providing upon drying a semipermeable elastic film for controlled outward moisture vapor transmission and substantial impermeability to bacteria and selected from the class consisting of vinyl polymers, including polyacrylic and polymethacrylic ester polymers, cellulose acetate butyrate, ethyl cellulose, and compatible combinations thereof, a synthetic resin "adhesive compatible with said film-former for ad hering said film dressing to normal skin but being substantially nonadherent to raw flesh, the cohesive strength of said film dressing being greater than adhesive strength of said adhesive for peelable removal of said film dressing from skin to which it is applied, a plasticizer for said film-former and said adhesive effecting in said film dressing controlled flexibility and elasticity thereof for conforming to movements and contours of skin to which it is applied, and a bacteriostatic component for maintaining

Description

United States Patent 2,804,073 FLUID SURGICAL DRESSING William F. Gallienne, Springfield, and William E. Le May and Louis Pereny, Dayton, Ohio, assignors to Protective Treatments, Inc, Dayton, Ohio, a corporation of Ohio N0 Drawing. Application January 26, 1953,
Serial No. 333,366
6 Claims. (Cl. 128-156) This invention relates to a surgical dressing for wounds, burns and the like and, more particularly, to a transparent releasably adhesive dressing adapted to be applied as a liquid or spray.
According to this invention a surgical dressing is provided in the form of a tough, elastic, transparent film with mildly bacteriostatic properties. The film is non toxic, chemically inert, insoluble in body fluids; it is resistant to water while being sufficiently permeable to moisture vapor to prevent formation of blisters thereunder. The transparent film dressing includes an adhesive component providing controllable adhesion such that it adheres to normal skin sufficiently to anchor the film firmly yet be readily peelable for removal, and has little if any adhesion to raw flesh of an open wound or burned area or to newly formed skin beneath the dressing. Essentially this dressing is stable, impermeable to coliform group organisms, sterile, and adapted to be applied by wiping on, brushing and in theform of a spray. It is of such character that laymen Without medical training can apply the dressing so as to form an artificial skin over a wound or burn to stabilize the injured area and protect it until further medical treatment is obtained.
It is accordingly an object of this invention to provide as a new composition a sprayable liquid to be applied to wounds, burns, and the like to form thereover a nontoxic, sterile, releasably adhesive, transparent, water resistant, bacteriostatic, semipermeable film.
A further object of this invention is to provide in liquid composition a film forming component, a controlled adhesion producer, a plasticizer, and a bacteriostatic agent in a nontoxic vehicle for application to form a dressing of the character described.
Still another object of. this invention is to provide a liquid composition of the character described including a controlled adhesion producing component, separate from the film forming component, which forms releasable adhesion to normal skin without adhering to the injured area.
Another object of this invention is to provide a liquid composition of the character described which upon drying forms a tough, elastic film over a wound sufliciently permeable to permit outward moisture vapor transmission from the wound while being substantially impermeable to the inward passage of infection promoting organ- 1sms.
Still a further object of this invention is to provide a liquid composition of the character described which upon drying produces over a wound a transparent elastic film adherent to normal skin, nonadherent to raw flesh, and peelable from normal skin without softening or other treatment.
Still another object of this invention is to provide a liquid composition of the character described for application to human skin and injured areas thereof, with the composition having a toxicity or allergic reactivity level at least as low as conventional surgical dressing adhesives, and being substantially free of medication.
2,804,073 Patented Aug. 27, 1957 A further object of this invention is to provide a solvent or dispersion vehicle adapted to admit of application of a tough, elastic, transparent film dressing of the character described and of low smarting, nonirritating and nontoxic physiological effect on exposed tissue in open wounds, burns, and the like.
Other objects and advantages of this invention will be apparent from the following description and the appended claims.
In the treatment of many injuries, the immediate application of a sterile dressing may be of controlling importance particularly to prevent loss of body fluids and continued exposure of the injured area to bacteria and other sources of infection. For example, in burns where large areas of skin are destroyed, the loss of serum from the burned area is an important source of shock and perhaps fatality. Especially in instances where large numbers of people may be severely injured is it important to have available emergency treatment adapted for safe application by essentially untrained personnel. Considering, for example, a situation where a human being has suifered 50% body burns, it has been found that it may require a trained doctor and nurse over an hour to apply a standard ointment and pressure bandage consisting of several pounds ofointment and perhaps yards of bandage to provide emergency treatment. By contrast, the same burned area could be satisfactorily treated in ,about five minutes by two laymen using but four spray infection occasioned by repeated removals of the dressing to inspect the wound.
According to this invention a sprayable plastic composition is produced which will form upon application a transparent film over the injured area. The film, in addition to being transparent, is water-resistant and insoluble in body fluids. At the same time it is sufiiciently semipermeable to admit of the outward penetration of water vapor to preclude the formation of a water blister under the dressing when perspiration and/ or other body fluids collect. Such semipermeability does not destroy the cgntinuity of the film nor render it permeable to the inward passage of objectionable bacteria, and is essentially a controlled degree of moisture-vapor transmission as opposed to mechanical porosity.
In addition to being tough and sufliciently elastic to protect the wound and accommodate body movement, the film is also, when applied sufficiently adhesive to normal skin surrounding the injured area to maintain itself in position, yet readily removable by peeling without softening or other treatment. The film has, however, very limited if any adhesiveness for the exposed raw flesh of the injured area, and is of such character as to avoid adhesion to newly formed skin growing under the dressing. That is, compositions according to this invention exhibit selective adhesion to dry instead of wet skin or flesh.
Both the final dressing and its sprayable liquid original composition are relatively nontoxic to either normal skin or the injured area and exhibit low allergic reactivity. With the preferred compositions described below, the allergic reactivity level is less than that of medically accepted commercial surgical adhesive tape. The solvent or vehicle utilized preferably has a relatively low smarting level and is of such character aswill not promote flow of blood or other body fluids.
For application of the sprayable dressing by essentially untrained personnel, it includes substantially no medication, although it preferably includes components to maintain sterility or a bacteriostatic condition-i. e., it stabilizes and maintains existing conditions in the injured area preceding or following suitable professional medical treatent. The original liquid composition before application is substantially stable and nonoxidizing for convenient storage and maintains its own sterility and/or includes components which discourage the existence of obnoxious bacteria. Because of the selective or controlled adhesion to dry or healthy skin without adhesion to raw flesh and because of the insolubility of film components in body fluids there is substantially no transfer of film components into the Wound or to newly formed skin beneath the bandage.
A sprayable surgical dressing having the attributes noted has been produced according to this invention bythe combination of a film former, an adhesion producer, a plasticizer, and a bacteriostatic agent, which components are admixed to form, with a suitable vehicle, a liquid solution or emulsion. In addition to the dry film properties noted above, the liquid compositions according to this invention are stable to exposure to temperatures ranging from 65 F. to +165 F. in storage and are usable at temperatures ranging from 20 F. up to 130 F. In the form of an aqueous emulsion, the smarting level in contact with raw fieshmay be lower than when volatile organic solvents are used, although a solution of the liquid compositions may be readily post-emulsified to decrease the smarting effect if desired. When volatile solvents are used, the drying time of the film can be easily controlled, and is usually of the order of five minutes, while with application of the dressing in the form of a Water emulsion, this time may be increased if desired to about fifteen minutes or more.
Considering a solution type liquid composition to give upon drying a plastic dressing embodying this invention, the film former may be present in the proportion of about 100 parts by weight; the adhesion producer in from 5 to 80 parts by weight with approximately 50 parts being preferred; the plasticizer in up to 80 parts by weight with approximately 50 being preferred; and the bacteriostatic agent in up to 2 parts by Weight with approximately .25 being preferred. The bacteriostatic agent may be present as a part of the adhesion producing component. Sufficient nontoxic and volatile solvent is incorporated to produce the desired consistency with about 800 parts being preferred. 7
Such a composition is packed in metal containers or so-called aerosol spray-type containers accompanied by suitable well-known spray propellants such as halogenatedaliphatic type or compressed gaseous type propellants if application is desired by aerosol spray. It may also be applied by compressed gas spray, brushing, flowing, wiping on, or dipping.
The film forming component may be of the class consisting of vinyl polymers (including vinyl chloride-vinylidine component copolymers, vinyl chloride-vinyl acetate copolymers and carboxylated or hydroxylated modifications of such copolymers, vinyl chloride-butadiene polymers, vinyl butyral polymers, vinyl acetate polymers, etc.), polyacrylic and polymethacrylic esters and polymers, cellulose acetate butyrate, ethyl cellulose, and compatible combinations thereof. The adhesion producing component may be one or compatible combinations of such resins as glycerol phthalate, abietic acid-glycerol and organic acid and/or phenol modifications of such abietic acid glycerol, amine-aldehyde resins, and resins containing maleic anhydride or phenols (including cresols). The plasticizer may be one or a combination of such monomeric substances as dioctyl phthalate, butyl phthallyl butyl glycollate, di-2(ethyl-hexyl) azelate, acetylated castor oil, phthalic anhydride-vegetable oil derivatives, tricresyl phosphate, o.- and p.-toluene sulfonamides; or polymeric substances such as chlorinated paratfin, cumarone-indene, sebacic acid polymers, treated raw oiticia and other vegetable oils (treated to produce compatibility with film formers). The bacteriostatic agent may satisfactorily be maleic anhydride (as included, for example, in the adhesive component), phenols (including cresols), and compatible physiologically appropriate mercury compounds.
Satisfactory volatile solvents for the above include one or a combination of such solvents as organic esters (e. g., ethyl acetate), ketones (e. g. acetone), organic ethers or oxides (e. g. ethylene oxide), aromatic hydrocarbons (e. g., toluene), or chlorinated aliphatic hydrocarbons (e. g., methylene chloride). The solvent component is chosen to produce the desired drying rate and viscosity of liquid composition with regard to method of application, ease of storage, traumatic smarting effect, etc. As noted above, such a solution may be post-emulsified by the addition of appropriate emulsifying agents, anti-foaming agents, and Water.
A satisfactory method of preparation of the composition includes adding the film former slowly to the solvent with agitation in a suitable covered container taking care to avoid agglomeration. The remaining ingredients are added upon the complete solution of the film former and agitation is continued until all ingredients are dissolved. After suitable filtration to remove any suspended foreign matter, the liquid composition is packed into aerosol spray containers at approximately 0 F. in known manner, or otherwise packaged as desired.
As a specific example of a solution type composition embodying this invention, satisfactory results have been experienced with a combination of:
Example 1 Parts by weight Hydroxylated vinyl acetate-vinyl chloride co-polymer 100 Maleic anhydride modified, glycerol-abietic-Vacid resin 50 Sebacic acid co-polymer type plasticizer 50 Ethyl acetate 600 GP acetone 200 Example 2 N-butyl methacrylate polymer 120 Butyl phthalyl butyl glycollate 30 Phenol-modified glycerol-abietic-acid resin 50 Ethyl acetate 800 Example 3 Ethyl cellulose Di-octyl phthalate 80 Maleic anhydride modified, glycerol-abietic-acid resin 40 Ethyl acetate 800 Example 4 Vinyl chloride-vinyl acetate resin VAGH Paraplex G-SO (proprietary epoxidated-oil type plasticizer) 50 Amberlac D-96 (maleic anhydride modified glycerolabietic-acid resin) 50 Ethyl acetate 800 In the above examples the particular solvent was chosen for rate of drying, although other solvent blends may be used where necessary to slow up drying or to meet special requirements. It has been found, for example, that volatile chlorinated solvents have no deleterious effect on dried film properties when added to the liquid composition in the range of one volume of composition to two volumes of solvent. The concentration of plasticizer may also be varied to produce the desired flexibility or softness indicated by the requirements of use. The above noted maleic anhydride modified resin includes the bacteriostatic component because of its fungistatic and bacteriostatic properties and the proportions may be varied to a limited extent to produce the desired hardness, adhesiveness and flexibility suited for a particular application. p q
A suitable composition of the aqueous emulsion type embodying this invention includes a film forming component in the form of a latex oremulsion on a 50% nonvolatile basis in the range of approximately 200 parts by weight, a separate adhesion producer up to 80 parts by weight with 5 parts being preferred, a plasticizer up to 80 parts by weight with 1 part being preferred, a bacteriostatic agent up to 2 parts by weight with .25 being preferred (may be included with adhesion producer), and volatile solvents up to 20 parts by weight with 5 being preferred. The above composition is emulsified with a suitable emulsifying agent, a protective colloid and thickener if desired, and an anti-foaming agent to give an emulsion of desired consistency depending upon application requirements. For the above ranges approximately 450 parts of water is preferred.
The film forming component, in the form of an aqueous emulsion or latex, may be any of those substances noted above, although it has been found that cellulose acetate butyrate and ethyl cellulose are more appropriate for solvent type application than for the emulsion type. The adhesion producer can be any of those listed above and the plasticizing and bacteriostatic components include those mentioned for the solution type composition. Appropriate solvents include alcohols as well as the solvents listed above. Satisfactory emulsifying agents are selected from commercially available non-ionic, anionic or cationic surface active agents depending upon the selection of the film former latex and compatibility therewith as well as the ability to form a stable emulsion with the selected adhesive component. The protective colloid added is selected from such substances as methyl cellulose, carboxymethyl cellulose, polyvinyl alcohol, solubilized protein, etc., of such grades as will produce the desired viscosity in the completed composition depending upon the requirements of method of application and use.
In preparing a composition of the emulsion type embodying this invention, the latex or film former is usually commercially available as an emulsion. A second emulsion is made by dissolving the adhesion producing component, bacteriostatic agent and plasticizer in the least quantity of volatile solvent which will form a complete solution. It has been found that this usually results in a concentration of approximately 50% nonvolatiles. The emulsifying agent and anti-foaming agent are added to this solution and stirred until well dispersed. With vigorous agitation, sufficient water is added to produce the desired emulsion containing approximately 25% nonvolatiles. As one example of the emulsion type, 200 parts of film former latex are placed into a stainless steel mixing tank and then the 25% adhesion producer emulsion is slowly added thereto with good but not too vigorous agitation. Sufficient water is then added to reduce the nonvolatile content of the mixture to approximately 15% to 25% as desired. Finally sufficient amount of a solution of 3 parts methyl cellulose in 97 parts of cool water is added to produce the desired viscosity and stability. It will be noted that the proportion of volatile solvents used in this composition is purposely kept low to minimize the smarting action of the composition upon first contacting raw flesh.
The degree of inflammability of liquid compositions embodying this invention is also readily controlled. For example, the emulsion type noted above is essentially noninflammable and a solution type comprising a vinyl copolymer film former, an amine-aldehyde adhesive and a phosphate-ester plasticizer all dissolved in methylene chloride exhibits a very low degree of inflammability.
Either the solution type or the emulsion type of composition will produce upon drying a satisfactory dressing of the character described. The absence or low degree of medication indicates complete safety in the use of such dressing by substantially untrained laymen. The plastic film produced after evaporation of either the volatile solvents or the aqueous emulsion is tough, elastic, transparent, and of controlled adhesiveness to normal skin. The film is water resistant and the extractability of components thereof by water or body fluids is virtually negligible. Although the composition is sterile and bacteriostatic, it need not include bactericidal agents or other medication.
The liquid compositions produced are stable and nonoxidizing and, if spray application is desired, are of sufficiently low viscosity. Storage problems are minimized since, except as desired to control evaporation of solvent, there is no need for air tight or other pressure type containers for storage. The film, after application, can be peeled away from normal skin Without softening or other treatment and without a further application of solvent or water. The film upon application exhibits substantially no adhesiveness for raw flesh and, after drying, no adhesiveness for newly formed skin growing under the dressing so that disturbance of the healing wound or other trauma is virtually non-existent upon removal of the dressing. While the fihn is water resistant and impermeable to coliform organisms, it is semipermeable to water vapor which might otherwise collect beneath the applied dressing and form either blisters or channels through the dressing to the outside leaving entranceways for obnoxious infection producing material. Accordingly, with the dressing applied, healing therebeneath proceeds under essentially anaerobic conditions. The film formers utilized, when applied according to this invention, produce uniform and substantially bubble-free films free of accidental gas channels or infection admitting openings. Since the dried film is substantially resistant to passage of medicaments therethrough, it may be used to protect selected skin areas from medications desired to be applied only to other areas of the body.
While the compositions and products herein described constitute preferred embodiments of the invention, it is to be understood that the invention is not limited to these precise compositions and products, and that changes may be made therein without departing from the scope of the invention which is defined in the appended claims.
What is claimed is:
l. A liquid dressing for application to skin to provide upon drying an elastic semipermeable self-sustaining peel-able film dressing for wounds, burns and incisions, comprising a volatile liquid vehicle for said dressing, a film-former providing upon drying a semipermeable elastic film for controlled outward moisture vapor transmission and substantial impermeability to bacteria and selected from the class consisting of vinyl polymers, including polyacrylic and polymethacrylic ester polymers, cellulose acetate butyrate, ethyl cellulose, and compatible combinations thereof, a synthetic resinous adhesive compatible with said film-former for adhering said film dressing to normal skin but being substantially nonadherent to raw flesh, the cohesive strength of said film dressing being greater than the adhesive strength of said adhesive for peelable removability of said film dressingfrom skin to which it is applied, and a plasticizer for said filmformer and said adhesive effecting in said film dressing controlled flexibility and elasticity thereof for conforming to movements and contours of skin to which it is applied, said film-former and adhesive and plasticizer all being homogeneously admixed in said liquid vehicle for liquid application to skin.
2. A liquid dressing for application to skin to provide upon drying an elastic semipermeable self-sustaining peelable transparent film dressing for wounds, burns and incisions, comprising a latex film-former emulsion providing upon drying a semipermeable elastic film for controlled outward moisture vapor transmission and substantial impermeaoility to bacteria, a synthetic resinous emulsifiable adhesive compatible with said film-former for adhering said film dressing to normal skin but being substantially nonadherent to raw flesh, the cohesive strength of said film dressing being greater than the adhesive strength of said adhesive for peelable removability of said film dressing from skin to which it is applied, and a plasticizer for said film-former and said adhesive efiecting in said film dressing controlled flexibility and elasticity thereof for conforming to movements and contours of skin to Which it is applied, an emulsifying agent for all said components, and water, all said components being uniformly dispersed in water emulsion for liquid application to skin. a
3. A liquid dressing for application to skin to provide upon drying an elastic semipermeable self-sustaining peelable transparent film dressing for wounds, burns and incisions, comprising a non-irritating volatile liquid vehicle for said dressing, a synthetic resinous elastomeric film-former providing upon drying a semipermeable elastic film for controlled outward moisture vapor transmission and substantial impermeability to bacteria and selected from the class consisting of vinyl polymers, including polyacrylic and polymethacrylic ester polymers,
cellulose acetate butyrate, ethyl cellulose, and compatible combinations thereof, a synthetic resinous adhesive compatible with said film former for adhering said film dressing to normal skin but being substantially nonadherent to raw flesh and selected from the class consisting of glycerol phthalate, abietic-acid-glycerol and organic acid and vinyl modifications thereof, amine aldehyde resins, maleic anhydride modified resins, vinyl modified resins, and compatible combinations thereof, the cohesive strength of said film dressing being greater than adhesive strength of said adhesive for peelable removability of said film dressing from skin to which it is applied, and a plasticizer for said film former and said adhesive effecting in said film dressing controlled flexibility and elasticity thereof for conforming to movements and contours of skin to which it is applied, said film former and adhesive and plasticizer all being homogeneously admixed in said liquid vehicle for liquid application to skin.
4. A liquid dressing for application to skin to provide upon drying an elastic semipermeable self-sustaining peelable transparent film dressing for wounds, burns and incisions, comprising a major proportion of volatile solvent for said dressing, a resin film-former providing upon drying a semipermeable elastic film for controlled outward moisture vapor transmission and substantial impermeability to bacteria and selected from the class consisting of vinyl polymers, including polyacrylic and polymethacrylic ester polymers, cellulose acetate butyrate, ethyl cellulose, and compatible combinations thereof, a synthetic resin "adhesive compatible with said film-former for ad hering said film dressing to normal skin but being substantially nonadherent to raw flesh, the cohesive strength of said film dressing being greater than adhesive strength of said adhesive for peelable removal of said film dressing from skin to which it is applied, a plasticizer for said film-former and said adhesive effecting in said film dressing controlled flexibility and elasticity thereof for conforming to movements and contours of skin to which it is applied, and a bacteriostatic component for maintaining the sterility of said dressing during storage and use, all said components being homogeneously admixed in 7 said volatile solvent to sprayable consistency for application to skin.
5. A liquid dressing for application to skin to provide upon drying an elastic semipermeable self-sustaining peelable transparent film dressing for wounds, burns and incisions, comprising a non-irritating volatile liquid vehi le for said dressing, approximately 100 parts by weight of a synthetic resinous elastomeric film-former providing upon drying a semipermeable elastic film for controlled outward, moisture vapor transmission and substantial impermeability to bacteria and selected from the class consisting of vinyl polymers, including polyacrylic and polymethacrylic ester polymers, cellulose acetate butyrate, ethyl cellulose, and compatible combinations thereof; approximately 5 to parts by weight of a synthetic resinous adhesive compatible with said film former for. adhering said film dressing to normal skin bntbeing substantially nonadherent to raw flesh and selected from the class consisting of glycerol phthalate, abietic-acid-glycerol and organic acid and vinyl modifications thereof, amine aldehyde resins, maleic anhydride modified resins, vinyl modified resins, and compatible combinations thereof, the cohesive strength of said film dressing being greater than adhesive strength of said adhesive for peelable removability of said film dressing from skin to which it is applied, and up to approximately 80 parts by weight of a plasticizer for said film former and said adhesive efifecting in'said film dressing controlled flexibility and elasticity thereof for conforming to movements and contours of skin to which it is applied, said film former and adhesive and plastlcizer all being homogeneously admixed in said liquid vehicle for liquid application to skin.
6. A liquid dressing for application to skin to provide upon drying an elastic semipermeable self-sustaining peelable transparent film dressing for wounds, burns and incisions, comprising a non-irritating volatile liquid vehicle for said dressing, approximately parts by weight of a synthetic resinous elastomeric film-former providing upon drying a semipermeable elastic film for controlled outward moisture vapor transmission and substantial impermeability to bacteria and selected from the class consisting of vinyl polymers, including polyacrylic and polymethacrylic ester polymers, cellulose acetate butyrate, ethyl cellulose, and compatible combinations thereof, approximately 50 parts by weight of a synthetic resinous adhesive compatible with said film former for adhering said film dressing to normal skin but being sul stantially nonadherent to raw flesh and selected from the class consisting of, glycerol phthalate, abietic-acidglycerol and organic acid and vinyl modifications thereof, amine aldehyde resins, maleic anhydride modified resins, vinyl modified resins, and compatible combinations thereof, the cohesive strength of said film dressing being greater than adhesive strength of said adhesive for peelable removability of said film dressing from skin to which it is applied, and up to approximately 50 parts by weight of a plasticizer for said film former and said adhesive effecting in said film dressing controlled flexibility and elasticity thereof for conforming to movements and contours of skin to which it is applied, said film former and adhesive and plasticizer all being homogeneously admixed in said liquid vehicle for liquid application to skin.
References Cited in the file of this patent 'UNITED STATES PATENTS 2,231,407 Castor Feb. 11, 1941 2,415,901 Nelson et al. Feb. 18, 1947 2,456,387 Cooper Dec. 14, 1948 2,481,419 Hamilton Sept. 6, 1949 2,563,593 Engel Aug. 7, 1951 2,580,488 Vogl Jan. 1, 1952 FOREIGN PATENTS 558,100 Great Britain 1943 OTHER REFERENCES Choy et al.: U. S. Armed Forces Med. 1., 3:124155, September 1952.
J. A. M. A., Aug. 5, 1944, vol. 125, pp. 969-973, reprint pp. 1-21, Local Treatment of Thermal Cutaneous Burns, esp. page 15.

Claims (1)

1. A LIQUID DRESSING FOR APPLICATION TO SKIN TO PROVIDE UPON DRYING AN ELASTIC SEMIPERMEABLE SELF-SUSTANING PEELABLE FILM DRESSING FOR WOUNDS, BURNS AND INCISIONS, COMPRISING A VOLATILE LIQUID VEHICLE FOR SAID DRESSING, A FILM-FORMER PROVIDING UPON DRYING A SEMIPERMEABLE ELASTIC FILM FOR CONTROLLED OUTWARD MOISTURE VAPOR TRANSMISSION AND SUBSTANTIAL IMPERMEABILITY TO BACTERIA AND SELECTED FROM THE CLASS CONSISTING OF VINYL POLYMERS, INCLUDING POLYARCYLIC AND POLYMETHACRYLIC ESTER POLYMERS, CELLULOSE ACETATE BUTYRATE, ETHYL CELLULOSE, AND COMPATIBLE COMBINATION THEREOF, A SYNTHETIC RESINOUS ADHESIVE COMPATIBLE WITH SAID FILM-FORMER FOR ADHERING SAID FILM DRESSING TO NORMAL SKIN BUT BEING SUBSTANTIALLY NONADHERENT TO RAW FLESH THE COHESIVE STRENGTH OF SAID FILM DRESSING BEING GREATER THAN THE ADHESIVE STRENGTH OF SAID ADHESIVE FOR PEELIABLE REMOVABILITY OF SAID FILM DRESSING FROM SKIN TO WHICH IT IS APPLIED, AND A PLASTICIZER FOR SAID FILMFORMER AND SAID ADHESIVE EFFECTING IN SAID FILM DRESSING CONTROLLED FLEXIBILITY AND ELASTICITY THEREOF FOR CONFORMING TO MOVEMENTS AND CONTOURS OF SKIN TO WHICH IT IS APPLIED, SAID FILM-FORMER AND ADHESIVE AND PLASTICIZER ALL BEING HOMOGENEOUSLY ADMIXED IN SAID LIQUID VEHICLE FOR LIQUID APPLICATION TO SKIN.
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US2952584A (en) * 1956-08-21 1960-09-13 Whitmire Res Lab Inc Treatment of cattle
US2972545A (en) * 1957-09-11 1961-02-21 Johnson & Johnson Dressing composition
DE1106456B (en) * 1958-12-10 1961-05-10 Krieger & Co Nachf C Carrier varnish for remedies
US3066071A (en) * 1959-09-22 1962-11-27 American Cyanamid Co Prevention of bovine masttis
US3089811A (en) * 1959-02-24 1963-05-14 Gillette Inhibitor Co Aryl mercuric fungicidal compositions
US3100180A (en) * 1960-12-19 1963-08-06 Minnesota Mining & Mfg Dermal protective compositions
US3150048A (en) * 1958-03-21 1964-09-22 Ciba Ltd Nail lacquer removing preparations
US3172808A (en) * 1965-03-09 Method of treating wounds
US3220865A (en) * 1961-06-23 1965-11-30 Eastman Kodak Co Cellulose acetate butyrate emulsion coating
US3287222A (en) * 1962-03-16 1966-11-22 Roussel Uclaf Method for preparation of synthetic fiber medical dressing impregnated with therapeutic
US3476853A (en) * 1965-04-13 1969-11-04 Colgate Palmolive Co Sprayed opaque bandage composition
US3667472A (en) * 1961-10-19 1972-06-06 Borden Inc Adhesive for living tissue
US3847155A (en) * 1972-01-26 1974-11-12 O Bernaola Methods for the elimination of scars using copolymer films in place of surgical sutures
US3935308A (en) * 1974-08-08 1976-01-27 The United States Of America As Represented By The Secretary Of The Navy Wound covering and method of application
US4186190A (en) * 1978-11-13 1980-01-29 The United States Of America As Represented By The Secretary Of The Navy Method of treating burns using a poly-ε-caprolactone
WO1982000099A1 (en) * 1980-07-09 1982-01-21 Key Pharma Polymeric diffusion matrix for administration of drugs
FR2497815A1 (en) * 1981-01-13 1982-07-16 Bard Inc C R FILMOGENE COPOLYMER COMPOSITION AND DISPENSING SYSTEM FOR FORMING PROTECTIVE FILM ON SKIN
US4444933A (en) * 1982-12-02 1984-04-24 Borden, Inc. Adhesive cyanoacrylate compositions with reduced adhesion to skin
USRE31886E (en) * 1968-07-09 1985-05-14 T. J. Smith & Nephew Limited Moisture-vapor-permeable pressure-sensitive adhesive materials
US4584192A (en) * 1984-06-04 1986-04-22 Minnesota Mining & Manufacturing Company Film-forming composition containing an antimicrobial agent and methods of use
US4921691A (en) * 1985-08-22 1990-05-01 Stockel Richard F Spray on wound dressing compositions
EP0398489A2 (en) * 1989-04-10 1990-11-22 Minnesota Mining And Manufacturing Company Film-forming emulsion containing iodine and methods of use
US4985239A (en) * 1985-09-13 1991-01-15 Kao Corporation Microlatex hair cosmetic composition
US5024838A (en) * 1988-03-02 1991-06-18 Vicente Parrilla Compositions for the treatment of skin injuries
AU627340B2 (en) * 1989-07-18 1992-08-20 Ethicon Inc. Polymeric liquid dressing for skin
US5254132A (en) * 1992-09-01 1993-10-19 Medlogic, Inc. Methods for treating suturable wounds by use of sutures and cyanoacrylate adhesives
US5306490A (en) * 1992-04-20 1994-04-26 Medlogic, Inc. Methods for retarding blister formation by use of cyanoacrylate adhesives
WO1995000153A1 (en) * 1993-06-25 1995-01-05 Medlogic Global Corporation Methods for inhibiting skin ulceration by use of cyanoacrylate adhesives
US5580565A (en) * 1994-09-01 1996-12-03 Medlogic Global Corporation Use of cyanoacrylate adhesives for providing a protective barrier film for the skin
US5653769A (en) * 1994-02-24 1997-08-05 Medlogic Global Corporation Methods for reducing skin irritation from artificial devices by use of cyanoacrylate adhesives
US5763412A (en) * 1997-04-08 1998-06-09 Becton Dickinson And Company Film-forming composition containing chlorhexidine gluconate
US6200596B1 (en) * 1992-09-25 2001-03-13 3M Innovative Properties Company Skin treatment with adhesion enhancement properties
US6342213B1 (en) 1992-06-09 2002-01-29 Medlogic Global Corporation Methods for treating non-suturable wounds by use of cyanoacrylate adhesives
US6492434B1 (en) 1994-06-23 2002-12-10 Flowers Park Ltd. Methods for inhibiting skin ulceration by use of cyanoacrylate adhesives
US20070259029A1 (en) * 2006-05-08 2007-11-08 Mcentire Edward Enns Water-dispersible patch containing an active agent for dermal delivery
US20070258935A1 (en) * 2006-05-08 2007-11-08 Mcentire Edward Enns Water dispersible films for delivery of active agents to the epidermis
US20080057090A1 (en) * 2006-09-01 2008-03-06 Mcentire Edward Enns Wrinkle masking film composition for skin
US20080085972A1 (en) * 2006-10-05 2008-04-10 O'brien Emmett Patrick Switchable adhesive article for attachment to skin and method of using the same
US20110076244A1 (en) * 2009-09-25 2011-03-31 Pharmasol Corporation Surface coatings for skin
US10314935B2 (en) 2009-01-07 2019-06-11 Entrotech Life Sciences, Inc. Chlorhexidine-containing antimicrobial laminates
US11039615B2 (en) 2014-04-18 2021-06-22 Entrotech Life Sciences, Inc. Methods of processing chlorhexidine-containing polymerizable compositions and antimicrobial articles formed thereby

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US2415901A (en) * 1944-09-14 1947-02-18 Johnson & Johnson Pressure sensitive adhesive tape
US2456387A (en) * 1944-10-07 1948-12-14 Du Pont Nontacky synthetic film
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Cited By (48)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3172808A (en) * 1965-03-09 Method of treating wounds
US2952584A (en) * 1956-08-21 1960-09-13 Whitmire Res Lab Inc Treatment of cattle
US2972545A (en) * 1957-09-11 1961-02-21 Johnson & Johnson Dressing composition
US3150048A (en) * 1958-03-21 1964-09-22 Ciba Ltd Nail lacquer removing preparations
DE1106456B (en) * 1958-12-10 1961-05-10 Krieger & Co Nachf C Carrier varnish for remedies
US3089811A (en) * 1959-02-24 1963-05-14 Gillette Inhibitor Co Aryl mercuric fungicidal compositions
US3066071A (en) * 1959-09-22 1962-11-27 American Cyanamid Co Prevention of bovine masttis
US3100180A (en) * 1960-12-19 1963-08-06 Minnesota Mining & Mfg Dermal protective compositions
US3220865A (en) * 1961-06-23 1965-11-30 Eastman Kodak Co Cellulose acetate butyrate emulsion coating
US3667472A (en) * 1961-10-19 1972-06-06 Borden Inc Adhesive for living tissue
US3287222A (en) * 1962-03-16 1966-11-22 Roussel Uclaf Method for preparation of synthetic fiber medical dressing impregnated with therapeutic
US3476853A (en) * 1965-04-13 1969-11-04 Colgate Palmolive Co Sprayed opaque bandage composition
USRE31886E (en) * 1968-07-09 1985-05-14 T. J. Smith & Nephew Limited Moisture-vapor-permeable pressure-sensitive adhesive materials
USRE31887E (en) * 1968-07-09 1985-05-14 T. J. Smith & Nephew Limited Moisture-vapor-permeable pressure-sensitive adhesive materials
US3847155A (en) * 1972-01-26 1974-11-12 O Bernaola Methods for the elimination of scars using copolymer films in place of surgical sutures
US3935308A (en) * 1974-08-08 1976-01-27 The United States Of America As Represented By The Secretary Of The Navy Wound covering and method of application
US4186190A (en) * 1978-11-13 1980-01-29 The United States Of America As Represented By The Secretary Of The Navy Method of treating burns using a poly-ε-caprolactone
WO1982000099A1 (en) * 1980-07-09 1982-01-21 Key Pharma Polymeric diffusion matrix for administration of drugs
FR2497815A1 (en) * 1981-01-13 1982-07-16 Bard Inc C R FILMOGENE COPOLYMER COMPOSITION AND DISPENSING SYSTEM FOR FORMING PROTECTIVE FILM ON SKIN
US4444933A (en) * 1982-12-02 1984-04-24 Borden, Inc. Adhesive cyanoacrylate compositions with reduced adhesion to skin
AU568831B2 (en) * 1982-12-02 1988-01-14 Borden Chemical, Inc. 2-cyanoacrylate ester and polymer with reduced adhesion to skin
US4584192A (en) * 1984-06-04 1986-04-22 Minnesota Mining & Manufacturing Company Film-forming composition containing an antimicrobial agent and methods of use
US4921691A (en) * 1985-08-22 1990-05-01 Stockel Richard F Spray on wound dressing compositions
US4985239A (en) * 1985-09-13 1991-01-15 Kao Corporation Microlatex hair cosmetic composition
US5024838A (en) * 1988-03-02 1991-06-18 Vicente Parrilla Compositions for the treatment of skin injuries
US4978527A (en) * 1989-04-10 1990-12-18 Minnesota Mining And Manufacturing Company Film-forming emulsion containing iodine and methods of use
EP0398489A2 (en) * 1989-04-10 1990-11-22 Minnesota Mining And Manufacturing Company Film-forming emulsion containing iodine and methods of use
EP0398489A3 (en) * 1989-04-10 1992-04-22 Minnesota Mining And Manufacturing Company Film-forming emulsion containing iodine and methods of use
US5173291A (en) * 1989-04-10 1992-12-22 Minnesota Mining And Manufacturing Company Film-forming emulsion containing iodine and methods of use
AU627340B2 (en) * 1989-07-18 1992-08-20 Ethicon Inc. Polymeric liquid dressing for skin
US5306490A (en) * 1992-04-20 1994-04-26 Medlogic, Inc. Methods for retarding blister formation by use of cyanoacrylate adhesives
US6342213B1 (en) 1992-06-09 2002-01-29 Medlogic Global Corporation Methods for treating non-suturable wounds by use of cyanoacrylate adhesives
US5254132A (en) * 1992-09-01 1993-10-19 Medlogic, Inc. Methods for treating suturable wounds by use of sutures and cyanoacrylate adhesives
US6200596B1 (en) * 1992-09-25 2001-03-13 3M Innovative Properties Company Skin treatment with adhesion enhancement properties
WO1995000153A1 (en) * 1993-06-25 1995-01-05 Medlogic Global Corporation Methods for inhibiting skin ulceration by use of cyanoacrylate adhesives
US5403591A (en) * 1993-06-25 1995-04-04 Medlogic Global Corporation Methods for inhibiting skin ulceration by use of cyanoacrylate adhesives
US5653769A (en) * 1994-02-24 1997-08-05 Medlogic Global Corporation Methods for reducing skin irritation from artificial devices by use of cyanoacrylate adhesives
US6492434B1 (en) 1994-06-23 2002-12-10 Flowers Park Ltd. Methods for inhibiting skin ulceration by use of cyanoacrylate adhesives
US5580565A (en) * 1994-09-01 1996-12-03 Medlogic Global Corporation Use of cyanoacrylate adhesives for providing a protective barrier film for the skin
US5763412A (en) * 1997-04-08 1998-06-09 Becton Dickinson And Company Film-forming composition containing chlorhexidine gluconate
US20070259029A1 (en) * 2006-05-08 2007-11-08 Mcentire Edward Enns Water-dispersible patch containing an active agent for dermal delivery
US20070258935A1 (en) * 2006-05-08 2007-11-08 Mcentire Edward Enns Water dispersible films for delivery of active agents to the epidermis
US20080057090A1 (en) * 2006-09-01 2008-03-06 Mcentire Edward Enns Wrinkle masking film composition for skin
US20080085972A1 (en) * 2006-10-05 2008-04-10 O'brien Emmett Patrick Switchable adhesive article for attachment to skin and method of using the same
US7879942B2 (en) 2006-10-05 2011-02-01 Eastman Chemical Company Switchable adhesive article for attachment to skin and method of using the same
US10314935B2 (en) 2009-01-07 2019-06-11 Entrotech Life Sciences, Inc. Chlorhexidine-containing antimicrobial laminates
US20110076244A1 (en) * 2009-09-25 2011-03-31 Pharmasol Corporation Surface coatings for skin
US11039615B2 (en) 2014-04-18 2021-06-22 Entrotech Life Sciences, Inc. Methods of processing chlorhexidine-containing polymerizable compositions and antimicrobial articles formed thereby

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