US3928556A - Non-stinging wound dressing containing tertiary butyl alcohol - Google Patents

Non-stinging wound dressing containing tertiary butyl alcohol Download PDF

Info

Publication number
US3928556A
US3928556A US447032A US44703274A US3928556A US 3928556 A US3928556 A US 3928556A US 447032 A US447032 A US 447032A US 44703274 A US44703274 A US 44703274A US 3928556 A US3928556 A US 3928556A
Authority
US
United States
Prior art keywords
stinging
methacrylate
solvent
carbon atoms
wound dressing
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US447032A
Inventor
Ulf Allan Sweger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novitas Nuprot SA
Original Assignee
Novitas Nuprot SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Novitas Nuprot SA filed Critical Novitas Nuprot SA
Application granted granted Critical
Publication of US3928556A publication Critical patent/US3928556A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/30—Materials not provided for elsewhere for aerosols
    • 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
    • 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
    • A61L26/0023—Polysaccharides
    • 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
    • A61L26/0061—Use of materials characterised by their function or physical properties
    • A61L26/0076—Sprayable compositions

Definitions

  • ABSTRACT This invention is concerned with a solution of plastic material useful as a non-stinging wound dressing.
  • the solvent system is a mixture of stinging and nonstinging solvents in which the non-stinging solvent is primarily tertiary butyl alcohol.
  • the polarity of the solvent system is adjusted by altering the amount of stinging and non-stinging solvent to provide sufficient solvent capacity to dissolve the plastic material.
  • This wound dressing is preferably applied to the wound as an aerosol spray dressing containing a germicide.
  • the present invention is concerned with a clean, convenient, economical and effective wound dressing for small wounds, abrasions, burns, and varicose and decubitus ulcers.
  • Conventional gauze bandages and plasters do not protect wounds from infection and water, and must be changed often.
  • Conventional wound coverings often interfere with healing, inhibit normal bathing of the area around the wound, and are uneconomical in terms of staff time required for changing.
  • Wound dressings of plastic material in solvents avoid many of the problems associated with conventional dressings in that they protect a wound against infection, permit visual inspection of wound healing, allow the patient to maintain normal bathing habits, and are simple to apply. Despite obvious advantages these products are not widely used because of the enormous stinging pain associated with their application to unanesthetized raw surfaces (British Medical Journal, 2 July 3 (1954) at page 18).
  • the present invention encompasses a non-stinging wound dressing comprising a plastic material dissolved in a solvent system, the solvent system containing 70% or more non-stinging solvent, the non-stinging solvent containing more than 50% tertiary butyl alcohol.
  • the present invention includes the non-stinging wound dressings as set forth above further containing medicinally active agents and it also includes non-stinging aerosol spray wound dressings comprising propellant gases and a plastic material dissolved in a solvent system, the solvent system containing 70% or more non-stinging solvent, the nonstinging solvent containing 50% or more tertiary butyl alcohol.
  • a solvent system consisting of tertiary butyl alcohol alone or tertiary butyl alcohol in combination with other non-stinging solvents stinging solvents, or mixtures of stinging and non-stinging solvents within the above specified limitations is suitable for practicing the present invention.
  • the present invention encompasses also a method for dressing wounds, which comprises applying a film of any of the non-stinging wound dressings or non-stinging aerosol wound dressings herein described to a wound.
  • saturated hydrocarbons and chlorofluoro-substituted hydrocarbons are non-stinging solvents.
  • the saturated straight or branched chain hydrocarbons containing 5-8 'carbon atoms, saturated cyclic hydrocarbons containing 5-8 carbon atoms, and chlorofluoro-substituted saturated hydrocarbons containing 1-2 carbon atoms are non-stinging solvents.
  • Cyclopentane, cyclohexane, cycloheptane, cyclooctane, npentane, n-hexane, n-heptane, n-octane, fluorotrichloromethane, sym-tetrachlorodifluoroethane, trifluorotrichloroethane, difluorochloromethane, and sym-dichlorotetrafluoroethane are examples of nonstinging solvents.
  • Common polar solvents such as low molecular weight alcohols, ketones, and esters are determined to be stinging solvents by the above test.
  • Primary and secondary alcohols containing 1-6 carbon atoms, ketones containing 3-7 carbon atoms, esters of acids containing 1-4 carbon atoms and alcohols having 1-6 carbon atoms are stinging solvents useful for increasing polarity of the solvent system to facilitate dissolving the plastic material.
  • Methanol, ethanol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, isobutyl alcohol, secondary butyl alcohol, acetone, methyl ethyl ketone, ethyl acetate, methylamyl acetate, isopropyl acetate, ethyl lactate, chloroform, and trichloroethylene are suitable but not exclusive examples of a stinging polar solvent.
  • tertiary butyl alcohol alone does not sting. It has also been found that non-stinging solvents do not cause vasodilation or haemolysis of red blood cells.
  • Table 1 illustrates the relationship of stinging effects of solvents as determined by sandpaper wounds on the lower arm of human subjects and vasodilation as determined by microscopic examination.
  • Table 2 illustrates the haemolysis effects of stinging solvents or red blood cells as determined by ultraviolet spectroscopy. Surprisingly up to 15% of tertiary butyl alcohol does not cause haemolysis.
  • Polymers and copolymers prepared from lower alkyl acrylates and methacrylates having 1 to 3 carbon atoms in the alkyl group such as methyl acrylate, ethyl acrylate, isopropyl acrylate, methyl methacrylate, ethyl methacrylate, propyl methacrylate, methoxyethyl acrylate, ethoxyethyl acrylate, methoxyethyl methacrylate, ethoxyethyl methacrylate, acrylamide, methacrylamide, n-alkyl substituted acrylamides and methacrylamides such as N-methyl, ethyl, propyl acrylamides and methacrylamides, N-vinyl pyrrolidone, hydroxy-(lower alkyl) acrylates and methacrylates form suitable but not exclusive plastic material useful in practicing this invention.
  • Plastic materials selected from the group comprising poly(lower alkyl)methacrylate, poly-2-alkoxyethyl methacrylate and copolymers thereof are preferred.
  • N-butyl methacrylate, isobutyl methacrylate, 2-ethoxyethyl methacrylate, 80/20 copolymer of isobutyl methacrylate/n-butyl methacrylate and methyl methacrylate are preferable plastic materials.
  • Polyvinyl butyral, ethyl cellulose, polyvinyl ethyl ether, and polyisobutylene and copolymers thereof are representative of other desirable plastic materials.
  • medicinally active ingredients such as germicides, fungicides, antibiotics, steroids, local anesthetics or the like may be utilized by having the medicinally active ingredient suspended or entrapped in the polymer, or if desired, dissolved in the liquid phase of the system.
  • medicinally active ingredients examples include 2,4,4-trichloro-2'-hydroxydiphenyl ether, benzocaine, xylocaine, aspirin, sodium omadine (a derivative of l-hydroxypyridine-2-thione), hexachlorophene, bacitracin, cortisone, trimethyl benzyl ammonium chloride, cetyl pyridinium chloride, penicillin, Aureomycin (chlorotetracycline), chloromycetin (chloramphenicol), merthiolate, sulfanilamide, sulfathiaozole, sulfaguanidine, sulfapyridine, salicyclic acid, Griseofulvin, undecylenic acid, zinc undecylenate, tetracycline, Terracycin (hydroxytetracycline), dienestrol, ethynyl estradiol, diethyl stilbesterol, estradiol, methyl
  • the wound dressing of this invention of plastics in a solvent system is an effective method of treating wounds and may be applied by brushing, dabbing, by squeeze bottles or by aerosol spray. Aerosol spray is the preferred method of application, since it provides a thin, tough and transparent film.
  • the invention can be used to form spray-on bandages not only for human wound but also is useful in the field of veterinary medicine for wounds on the skins of animals such as dogs, cats, sheep, cattle (e.g. to protect cows having mastitis on their teats), goats, pigs and horses and zoological animals such as lions, tigers, deer, zebra, etc.
  • the film can be applied in a matter of seconds; there is no stinging upon application; healing of the wound can be observed; the patient may bathe normally, and the film is easily removed after several days.
  • this invention embodies effective methods of dressing wounds.
  • Aerosols require that the solvent, plastic material and medicinal, if any, be placed in a pressurized container with propellant gases.
  • propellant gases include those well known in the art.
  • compressed gases such as carbon dioxide, nitrous oxide, nitrogen, liquifiedvolative hydrocarbons such as propane, n-butane, isobutane and Z-methylbutane, methylene chloride, vinyl chloride, fluorinated compounds including perhalogenated compounds and fluorinated hydrocarbons such as dichlorodifluoromethane, 1,1,2- trichloro-l,2,2-trifluoroethane, trichlorofluoromethane, 1,2-dichlorotetrafluoroethane, octofluorocyclobutane, chlorodifluoromethane, l,l-difluoroethane, vinyl fluoride, vinylidene fluoride, 1-chloro-1,l-difluoroethane.
  • Non-stinging aerosol spray wound dressings of propellant gases and plastic material in a solvent system containing or more non-stinging solvent said nonstinging solvent containing 50% or more tertiary butyl alcohol, are in the scope of this invention.
  • Non-stinging solvent may be used alone or in combination with stinging solvents selected from the group comprising alcohols containing l-6 carbon atoms, ketones containing l-4 carbon atoms, and esters of acids containing l-4 carbon atoms and alcohols containing l-6 carbon atoms or mixtures of the aforementioned polar solvents.
  • Preferred non-stinging wound dressings suitable for dabbing and brushing are prepared from 525% solutions of plastic material selected from the group comprising poly(lower alkyl)methacrylate, poly-2-alkoxyethyl methacrylate, and copolymers thereof in tertiary butyl alcohol (at least 50%) and trichlorotrifluoroethane.
  • plastic material selected from the group comprising poly(lower alkyl)methacrylate, poly-2-alkoxyethyl methacrylate, and copolymers thereof in tertiary butyl alcohol (at least 50%) and trichlorotrifluoroethane.
  • a germicide such as 2,4,4-trichloro-2-hydroxydiphenyl ether is desirable.
  • up to 30% stinging solvent usually 0.5 to 30%, improves the solubility characteristics of the plastic material without causing any stinging.
  • the preferred non-stinging wound dressings are converted to non-stinging aerosol wound sprays by combining the non-stinging wound dressing with suitable propellant gases in a pressurized aerosol container.
  • a preferred formulation of a non-stinging aerosol spray wound dressing is:
  • a non-stinging wound dressing particularly suited for dabbing or brushing on a wound is prepared by dissolving 15 parts polyvinyl butyral in parts tertiary butyl alcohol.
  • EXAMPLE 2 A non-stinging wound dressing particularly suited for dabbing or brushing on a wound is prepared by dissolving l5 parts ethyl cellulose in 85 parts tertiary butyl alcohol.
  • EXAMPLE 3 A non-stinging wound dressing particularly suited for dabbing or brushing on a wound is prepared by dissolving 15 parts polyvinyl ethyl ether in 85 parts tertiary butyl alcohol.
  • EXAMPLE 4 A non-stinging wound dressing particularly suited for dabbing or brushing on a wound is prepared by dissolving l5 parts polyisobutylene in 85 parts tertiary butyl alcohol. 7
  • a non-stinging wound dressing particularly suited for dabbing or brushing on a wound is prepared by dissolving l5 parts of poly-n-butyl methacrylate in 45 parts of tertiary butyl alcohol and 40 parts of trichloro trifluoroethane.
  • a non-stinging wound dressing particularly suited for dabbing or brushing on a wound is prepared by dissolving l5 parts of poly-isobutyl methacrylate in 45 parts tertiary butyl alcohol and 40 parts trichlorotrifluoroethane.
  • EXAMPLE 7 A non-stinging wound dressing particularly suited for dabbing or brushing on a wound is prepared by dissolving 14 parts of a 95/5 copolymer of 2-ethoxyethyl methacrylate/methyl methacrylate and l part dibutyl phthalate in 45 parts of tertiary butyl alcohol and 40 parts of trichlorotrifluoroethane.
  • EXAMPLE 8 A non-stinging wound dressing particularly suited for dabbing or brushing on a wound is prepared by dissolving 15 parts of a 80/20 copolymer of isobutyl methacrylate/n-butyl methacrylate in 60 parts of tertiary butyl alcohol and 25 parts acetone.
  • a non-stinging wound dressing particularly suited for brushing or dabbing on a wound is prepared by dissolving l5 parts polyvinyl butyral in 77 parts tertiary butyl alcohol and 8 parts ethyl alcohol.
  • EXAMPLE 10 A non-stinging wound dressing particularly suited for brushing or dabbing on a wound is prepared by dissolving parts poly-2-ethoxyethoxy methacrylate in 60 parts tertiary butyl alcohol and parts ethyl acetate.
  • This formulation provides about 250 2 cm. X 7 cm. bandage strips.
  • a non-stinging wound dressing comprising film forming plastic material dissolved in a solvent system, said solvent system containing or more non-stinging solvent, said non-stinging solvent consisting of tertiary butyl alcohol and solvent selected from the group comprising straight and branched chain saturated hydrocarbons having 5-8 carbon atoms, saturated cyclic hydrocarbons having 5-8 carbon atoms and chlorofluoro substituted saturated hydrocarbons containing 1-2 carbon atoms and mixtures thereof wherein the non-stinging solvent contains 50% or more tertiary butyl alcohol, said film forming plastic material selected from the group comprising, N-butyl methacrylate, isobutyl methacrylate, 2-ethoxyethyl methacrylate, methyl methacrylate, polyvinyl butyral, ethyl cellulose, polyvinyl ethyl ether, polyisobutylene polymers and /20 isobutyl methacrylate/N-butyl methacrylate and
  • a non-stingingwound dressing comprising plastic material in asolvent system, said plastic material selected from the group comprising poly(- lower alkyl)methacrylate, poly-2-alkoxyethyl methacrylate and copolymers thereof.
  • a non-stinging wound dressing comprising a 525% solution of polyvinyl butyral in tertiary butyl alcohol.
  • a non-stinging wound dressing comprising a 5-25% solution of ethyl cellulose in tertiary butyl alcohol.
  • a non-stinging wound dressing comprising a 5-25% solution of polyvinylethyl ether in tertiary butyl alcohol.
  • a non-stinging wound dressing comprising a 5.-25% solution of polyisobutylene in tertiary butyl alcohol.
  • a non-stinging wound dressing comprising 5-25% solution of plastic material selected from the group comprising poly(lower alkyl)methacrylate, poly-2-alkoxyethyl methacrylate and copolymers thereof in a tertiary butyl alcohol/trichlorotrifluoroethane aolvent system.
  • a non-stinging wound dressing comprising 45 parts tertiary butyl alcohol, 40 parts trichlorotrifluoroethane, and 15 parts polyisobutyl methacrylate.
  • a non-stinging wound dressing comprising 45 parts tertiary butyl alcohol, 40 parts trichlorotrifluoroethane, and I5 parts poly-n-butylmethacrylate.
  • a non-stinging wound dressing comprising 45 parts tertiary butyl alcohol, 40 parts trichlorotrifluoroethane, l4 parts 95/5 copolymer of 2-ethoxyethyl methacrylate/methyl methacrylate, and dibutyl phthalate.
  • a non-stinging wound dressing comprising a 525% solution of plastic material selected from the group comprising poly(lower alkyl)methacrylate, poly-2-alkoxyethyl methacrylate and copolymers thereof in tertiary butyl alcohol containing 05-30 per cent stinging solvent.
  • a non-stinging wound dressing comprising 60 parts tertiary butyl alcohol, 25 parts acetone, and 15 parts of 80/20 copolymer of isobutyl methacrylate/n-butyl methacrylate.
  • a non-stinging wound dressing comprising 60 parts tertiary butyl alcohol, 25 parts ethyl acetate, and parts poly-Z-ethoxyethyl methacrylate.
  • a non-stinging wound dressing further containing a medicinally active ingredient.
  • a non-stinging wound dressing further containing a germicide.
  • a non-stinging wound dressing comprising film forming plastic material dissolved in a solvent system, said solvent system containing stinging solvent and 70% or more non-stinging solvent, said non-stinging solvent consisting of tertiary butyl alcohol and a solvent selected from the group comprising straight and branched chain saturated hydrocarbons having 5-8 carbon atoms; saturated cyclic hydrocarbons having 5-8 carbon atoms and chlorofluoro substituted saturated hydrocarbons containing l-2 carbon atoms and mixtures thereof wherein the non-stinging solvent contains 50% or more tertiary butyl alcohol, said stinging solvent selected from the group comprising primary and secondary alcohols containing l-6 carbon atoms, ketones containing l-4 carbon atoms, esters of acids containing l-4 carbon atoms and alcohols containing l-6 carbon atoms, said film forming plastic material selected from the group comprising, N-butyl methacrylate, isobutyl methacrylate, 2-ethoxy
  • a non-stinging aerosol spray wound dressing comprising propellant gases together with film forming plastic material dissolved in a solvent system, said solvent system containing 70% or more non-stinging solvent, said non-stinging solvent consisting of tertiary butyl alcohol and solvent selected from the group comprising straight and branched chain saturated hydrocarbons having 5-8 carbon atoms, saturated cyclic hydrocarbons having 5-8 carbon atoms and chlorofluoro substituted saturated hydrocarbons containing l-2 carbonatoms and mixtures thereof wherein the nonstinging solvent contains 50% or more tertiary butyl alcohol, said film forming plastic material selected from the group comprising, N-butyl methacrylate, isobutyl methacrylate, 2-ethoxyethyl methacrylate, methyl methacrylate, polyvinyl butyral, ethyl cellulose, polyvinyl ethyl ether, polyisobutylene polymers and 80/20 isobutyl methacrylate/N-butyl
  • a non-stinging aerosol spray wound dressing comprising:
  • a non-stinging aerosol spray wound dressing further containing a germicide.
  • a non-stinging aerosol spray wound dressing comprising propellant gases together with film forming plastic material dissolved in a solvent system, said solvent system containing stinging solvent and or more non-stinging solvent, said non-stinging solvent consisting of tertiary butyl alcohol and a solvent selected from the group comprising straight and branched chain saturated hydrocarbons having 5-8 carbon atoms, saturated cyclic hydrocarbons having 5-8 carbon atoms and chlorofluoro substituted saturated hydrocarbons containing l-2 carbon atoms and mixtures thereof wherein the non-stinging solvent contains 50% or more tertiary butyl.
  • said stinging solvent selected from the group comprising primary and secondary alcohols containing l-6 carbon atoms, ketones containing l-4 carbon atoms, esters of acids containing l-4 carbon atoms and alcohols containing l-6 carbon atoms
  • said film forming plastic material selected from the group comprising, N-butyl methacrylate, isobutyl methacrylate, Z-ethoxyethyl methacrylate, methyl methacrylate, -polyvinyl butyral, ethyl cellulose, polyvinylethyl ether,polyisobutylene polymers and /20 isobutyl methacrylate/N-butyl methacrylate and /5 2-ethoxyethyl methacrylate/methyl methacrylate copolymers, said film -forming plastic material being skin adherent and washable upon drying.
  • a non-stinging aerosol spray wound dressing further containing a germicide, fungicide, antibiotic, steroid or local anesthetic.
  • a method for dre's'sin'g wounds comprising applying to the wound a thin film of a non-stinging wound dressing comprising film forming plastic material dissolved in a solvent system, said solvent system containing stinging solvent and 70% of'more non-stinging solvent, said non-stinging solvent consisting of tertiary butyl alcohol and a solvent selected from the group comprising straight and branched chain saturated hydrocarbons having 5-8 carbon atoms; saturated cyclic hydrocarbons having 5-8 carbon atoms and chlorofluoro substituted saturated hydrocarbons containing l2 carbon atoms and mixtures thereof wherein the non-stinging solvent contains 50% or more tertiary butyl alcohol, said stinging solvent selected from the group comprising primary and secondary alcohols containing l-6 carbon atoms,.ketones containing l-4 carbon atoms, esters of acids containing 1-4 carbon atoms and alcohols containing l-6 carbon atoms, said film forming plastic material selected from the group comprising

Abstract

This invention is concerned with a solution of plastic material useful as a non-stinging wound dressing. The solvent system is a mixture of stinging and non-stinging solvents in which the nonstinging solvent is primarily tertiary butyl alcohol. The polarity of the solvent system is adjusted by altering the amount of stinging and non-stinging solvent to provide sufficient solvent capacity to dissolve the plastic material. This wound dressing is preferably applied to the wound as an aerosol spray dressing containing a germicide.

Description

United States Patent [1 1 Sweger 1 NON-STINGING WOUND DRESSING CONTAINING TERTIARY BUTYL ALCOHOL [75] Inventor: Ulf Allan Sweger, Marbella, Spain [73] Assignee: Novitas Nuprot SA, Freibourg,
Switzerland 22 Filed: Feb. 28, 1974 21 Appl. No.: 447,032
[30] Foreign Application Priority Data Dec. 23, 1975 [56] References Cited I UNITED STATES PATENTS 3,297,536 l/l967 Baron 424/47 3,568,394 3/1971 Margolis....
Lanthier et a1.
Gould et a1. 424/45 Primary Examiner-Stanley J. Friedman Attorney, Agent, or Firm-John J. McDonnell [57] ABSTRACT This invention is concerned with a solution of plastic material useful as a non-stinging wound dressing. The solvent system is a mixture of stinging and nonstinging solvents in which the non-stinging solvent is primarily tertiary butyl alcohol. The polarity of the solvent system is adjusted by altering the amount of stinging and non-stinging solvent to provide sufficient solvent capacity to dissolve the plastic material. This wound dressing is preferably applied to the wound as an aerosol spray dressing containing a germicide.
22 Claims, No Drawings NON-STINGING WOUND DRESSING CONTAINING TERTIARY BUTYL ALCOHOL The present invention is concerned with a clean, convenient, economical and effective wound dressing for small wounds, abrasions, burns, and varicose and decubitus ulcers. Conventional gauze bandages and plasters do not protect wounds from infection and water, and must be changed often. Conventional wound coverings often interfere with healing, inhibit normal bathing of the area around the wound, and are uneconomical in terms of staff time required for changing. Wound dressings of plastic material in solvents avoid many of the problems associated with conventional dressings in that they protect a wound against infection, permit visual inspection of wound healing, allow the patient to maintain normal bathing habits, and are simple to apply. Despite obvious advantages these products are not widely used because of the enormous stinging pain associated with their application to unanesthetized raw surfaces (British Medical Journal, 2 July 3 (1954) at page 18).
It is an object of this invention to prepare a non-stinging wound spray of plastics in a solvent system.
In its broadest context the present invention encompasses a non-stinging wound dressing comprising a plastic material dissolved in a solvent system, the solvent system containing 70% or more non-stinging solvent, the non-stinging solvent containing more than 50% tertiary butyl alcohol. The present invention includes the non-stinging wound dressings as set forth above further containing medicinally active agents and it also includes non-stinging aerosol spray wound dressings comprising propellant gases and a plastic material dissolved in a solvent system, the solvent system containing 70% or more non-stinging solvent, the nonstinging solvent containing 50% or more tertiary butyl alcohol. A solvent system consisting of tertiary butyl alcohol alone or tertiary butyl alcohol in combination with other non-stinging solvents stinging solvents, or mixtures of stinging and non-stinging solvents within the above specified limitations is suitable for practicing the present invention. The present invention encompasses also a method for dressing wounds, which comprises applying a film of any of the non-stinging wound dressings or non-stinging aerosol wound dressings herein described to a wound.
By applying solvents to open wounds produced by sandpaper on the lower arm of subjects it has been discovered that saturated hydrocarbons and chlorofluoro-substituted hydrocarbons are non-stinging solvents. The saturated straight or branched chain hydrocarbons containing 5-8 'carbon atoms, saturated cyclic hydrocarbons containing 5-8 carbon atoms, and chlorofluoro-substituted saturated hydrocarbons containing 1-2 carbon atoms are non-stinging solvents. Cyclopentane, cyclohexane, cycloheptane, cyclooctane, npentane, n-hexane, n-heptane, n-octane, fluorotrichloromethane, sym-tetrachlorodifluoroethane, trifluorotrichloroethane, difluorochloromethane, and sym-dichlorotetrafluoroethane are examples of nonstinging solvents.
Common polar solvents such as low molecular weight alcohols, ketones, and esters are determined to be stinging solvents by the above test. Primary and secondary alcohols containing 1-6 carbon atoms, ketones containing 3-7 carbon atoms, esters of acids containing 1-4 carbon atoms and alcohols having 1-6 carbon atoms are stinging solvents useful for increasing polarity of the solvent system to facilitate dissolving the plastic material. Methanol, ethanol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, isobutyl alcohol, secondary butyl alcohol, acetone, methyl ethyl ketone, ethyl acetate, methylamyl acetate, isopropyl acetate, ethyl lactate, chloroform, and trichloroethylene are suitable but not exclusive examples of a stinging polar solvent.
It has unexpectedly been found that of monohydroxy alcohols containing from 1 6 carbon atoms, tertiary butyl alcohol alone does not sting. It has also been found that non-stinging solvents do not cause vasodilation or haemolysis of red blood cells. Table 1 illustrates the relationship of stinging effects of solvents as determined by sandpaper wounds on the lower arm of human subjects and vasodilation as determined by microscopic examination. Table 2 illustrates the haemolysis effects of stinging solvents or red blood cells as determined by ultraviolet spectroscopy. Surprisingly up to 15% of tertiary butyl alcohol does not cause haemolysis.
Table l Stinging Pain vasodilation methyl alcohol yes pronounced ethyl alcohol yes pronounced n-propyl alcohol yes pronounced isopropyl alcohol yes pronounced n-butyl alcohol yes pronounced isobutyl alcohol yes pronounced sec-butyl alcohol yes pronounced tert-butyl alcohol no none acetone yes pronounced ethyl acetate yes pronounced ethylene chloride yes pronounced ethyl lactate yes pronounced chloroform yes pronounced methyl amyl acetate yes pronounced methyl ethyl ketone yes pronounced methyl glycol yes pronounced isopropyl acetate yes pronounced propylene glycol yes pronounced trichloroethylene yes pronounced trichlorotrifluoroethane no none difluorodichloromethane no none fluorotrichloromethane no none difluorochloromethane no none dichlorodifluoromethane no none sym-dichlorotetrafluoroethane no none Table 2 Haemolysis in Per Cent Solvent Per Cent by Volume methyl alcohol 5 15 25 60 100 100 ethyl alcohol 5 l0 I5 50 60 100 npropyl alcohol 0 5 15 30 60 100 isopropyl alcohol 0 5 15 30 60 100 tertiary butyl alcohol 0 0 0 0 0 0 ethyl acetate 0 15 SS l()() acetone 5 20 50 60 I00 100 From Tables 1 and 2 it is evident that of the low molecular weight alcohols tertiary butyl alcohol alone does not sting and it appears that stinging effects are related to vasodilation and haemolysis.
lt has most surprisingly been found that mixtures of stinging solvents and non-stinging solvents provide non-stinging solvent systems. Thus solvent systems containing up to 30% stinging solvent and 70% or more non-stinging solvent wherein the non-stinging solvent contains 50% or more tertiary butyl alcohol do not 3 produce a painful stinging effect when applied to a wound.
Polymers and copolymers prepared from lower alkyl acrylates and methacrylates having 1 to 3 carbon atoms in the alkyl group such as methyl acrylate, ethyl acrylate, isopropyl acrylate, methyl methacrylate, ethyl methacrylate, propyl methacrylate, methoxyethyl acrylate, ethoxyethyl acrylate, methoxyethyl methacrylate, ethoxyethyl methacrylate, acrylamide, methacrylamide, n-alkyl substituted acrylamides and methacrylamides such as N-methyl, ethyl, propyl acrylamides and methacrylamides, N-vinyl pyrrolidone, hydroxy-(lower alkyl) acrylates and methacrylates form suitable but not exclusive plastic material useful in practicing this invention.
Plastic materials selected from the group comprising poly(lower alkyl)methacrylate, poly-2-alkoxyethyl methacrylate and copolymers thereof are preferred. For example, N-butyl methacrylate, isobutyl methacrylate, 2-ethoxyethyl methacrylate, 80/20 copolymer of isobutyl methacrylate/n-butyl methacrylate and methyl methacrylate are preferable plastic materials. Polyvinyl butyral, ethyl cellulose, polyvinyl ethyl ether, and polyisobutylene and copolymers thereof are representative of other desirable plastic materials.
Furthermore, medicinally active ingredients such as germicides, fungicides, antibiotics, steroids, local anesthetics or the like may be utilized by having the medicinally active ingredient suspended or entrapped in the polymer, or if desired, dissolved in the liquid phase of the system. Examples of such medicinally active ingredients include 2,4,4-trichloro-2'-hydroxydiphenyl ether, benzocaine, xylocaine, aspirin, sodium omadine (a derivative of l-hydroxypyridine-2-thione), hexachlorophene, bacitracin, cortisone, trimethyl benzyl ammonium chloride, cetyl pyridinium chloride, penicillin, Aureomycin (chlorotetracycline), chloromycetin (chloramphenicol), merthiolate, sulfanilamide, sulfathiaozole, sulfaguanidine, sulfapyridine, salicyclic acid, Griseofulvin, undecylenic acid, zinc undecylenate, tetracycline, Terracycin (hydroxytetracycline), dienestrol, ethynyl estradiol, diethyl stilbesterol, estradiol, methyltestosterone, progesterone, ascorbic acid. Thus this system of plastic material in a non-stinging solvent is an effective means for topically administering drugs.
The wound dressing of this invention of plastics in a solvent system is an effective method of treating wounds and may be applied by brushing, dabbing, by squeeze bottles or by aerosol spray. Aerosol spray is the preferred method of application, since it provides a thin, tough and transparent film. The invention can be used to form spray-on bandages not only for human wound but also is useful in the field of veterinary medicine for wounds on the skins of animals such as dogs, cats, sheep, cattle (e.g. to protect cows having mastitis on their teats), goats, pigs and horses and zoological animals such as lions, tigers, deer, zebra, etc. The film can be applied in a matter of seconds; there is no stinging upon application; healing of the wound can be observed; the patient may bathe normally, and the film is easily removed after several days. Thus, this invention embodies effective methods of dressing wounds.
Aerosols require that the solvent, plastic material and medicinal, if any, be placed in a pressurized container with propellant gases. Suitable propellant gases include those well known in the art. There can be used compressed gases such as carbon dioxide, nitrous oxide, nitrogen, liquifiedvolative hydrocarbons such as propane, n-butane, isobutane and Z-methylbutane, methylene chloride, vinyl chloride, fluorinated compounds including perhalogenated compounds and fluorinated hydrocarbons such as dichlorodifluoromethane, 1,1,2- trichloro-l,2,2-trifluoroethane, trichlorofluoromethane, 1,2-dichlorotetrafluoroethane, octofluorocyclobutane, chlorodifluoromethane, l,l-difluoroethane, vinyl fluoride, vinylidene fluoride, 1-chloro-1,l-difluoroethane. The propellant should contain a substantial amount of volatile material boiling at not over 20 C., but there can also be present a significant amount of less volative material boiling up to 50 C. Therefore non-stinging aerosol spray wound dressings of propellant gases and plastic material in a solvent system containing or more non-stinging solvent, said nonstinging solvent containing 50% or more tertiary butyl alcohol, are in the scope of this invention. Non-stinging solvent may be used alone or in combination with stinging solvents selected from the group comprising alcohols containing l-6 carbon atoms, ketones containing l-4 carbon atoms, and esters of acids containing l-4 carbon atoms and alcohols containing l-6 carbon atoms or mixtures of the aforementioned polar solvents.
Preferred non-stinging wound dressings suitable for dabbing and brushing are prepared from 525% solutions of plastic material selected from the group comprising poly(lower alkyl)methacrylate, poly-2-alkoxyethyl methacrylate, and copolymers thereof in tertiary butyl alcohol (at least 50%) and trichlorotrifluoroethane. The addition of a germicide such as 2,4,4-trichloro-2-hydroxydiphenyl ether is desirable. The addition of up to 30% stinging solvent, usually 0.5 to 30%, improves the solubility characteristics of the plastic material without causing any stinging.
The preferred non-stinging wound dressings are converted to non-stinging aerosol wound sprays by combining the non-stinging wound dressing with suitable propellant gases in a pressurized aerosol container.
A preferred formulation of a non-stinging aerosol spray wound dressing is:
0.00M! 400 ppm based on polymer content pol tetrafluoroethylene dic lorophene EXAMPLE 1 A non-stinging wound dressing particularly suited for dabbing or brushing on a wound is prepared by dissolving 15 parts polyvinyl butyral in parts tertiary butyl alcohol.
EXAMPLE 2 A non-stinging wound dressing particularly suited for dabbing or brushing on a wound is prepared by dissolving l5 parts ethyl cellulose in 85 parts tertiary butyl alcohol.
EXAMPLE 3 A non-stinging wound dressing particularly suited for dabbing or brushing on a wound is prepared by dissolving 15 parts polyvinyl ethyl ether in 85 parts tertiary butyl alcohol.
EXAMPLE 4 A non-stinging wound dressing particularly suited for dabbing or brushing on a wound is prepared by dissolving l5 parts polyisobutylene in 85 parts tertiary butyl alcohol. 7
EXAMPLE 5 A non-stinging wound dressing particularly suited for dabbing or brushing on a wound is prepared by dissolving l5 parts of poly-n-butyl methacrylate in 45 parts of tertiary butyl alcohol and 40 parts of trichloro trifluoroethane.
EXAMPLE 6 A non-stinging wound dressing particularly suited for dabbing or brushing on a wound is prepared by dissolving l5 parts of poly-isobutyl methacrylate in 45 parts tertiary butyl alcohol and 40 parts trichlorotrifluoroethane.
EXAMPLE 7 A non-stinging wound dressing particularly suited for dabbing or brushing on a wound is prepared by dissolving 14 parts of a 95/5 copolymer of 2-ethoxyethyl methacrylate/methyl methacrylate and l part dibutyl phthalate in 45 parts of tertiary butyl alcohol and 40 parts of trichlorotrifluoroethane.
EXAMPLE 8 A non-stinging wound dressing particularly suited for dabbing or brushing on a wound is prepared by dissolving 15 parts of a 80/20 copolymer of isobutyl methacrylate/n-butyl methacrylate in 60 parts of tertiary butyl alcohol and 25 parts acetone.
EXAMPLE 9 A non-stinging wound dressing particularly suited for brushing or dabbing on a wound is prepared by dissolving l5 parts polyvinyl butyral in 77 parts tertiary butyl alcohol and 8 parts ethyl alcohol.
EXAMPLE 10 A non-stinging wound dressing particularly suited for brushing or dabbing on a wound is prepared by dissolving parts poly-2-ethoxyethoxy methacrylate in 60 parts tertiary butyl alcohol and parts ethyl acetate. I
EXAMPLE ll I An aerosol spray container is charged with 200 g. of
This formulation provides about 250 2 cm. X 7 cm. bandage strips.
What is claimed is:
l. A non-stinging wound dressing comprising film forming plastic material dissolved in a solvent system, said solvent system containing or more non-stinging solvent, said non-stinging solvent consisting of tertiary butyl alcohol and solvent selected from the group comprising straight and branched chain saturated hydrocarbons having 5-8 carbon atoms, saturated cyclic hydrocarbons having 5-8 carbon atoms and chlorofluoro substituted saturated hydrocarbons containing 1-2 carbon atoms and mixtures thereof wherein the non-stinging solvent contains 50% or more tertiary butyl alcohol, said film forming plastic material selected from the group comprising, N-butyl methacrylate, isobutyl methacrylate, 2-ethoxyethyl methacrylate, methyl methacrylate, polyvinyl butyral, ethyl cellulose, polyvinyl ethyl ether, polyisobutylene polymers and /20 isobutyl methacrylate/N-butyl methacrylate and /5 2-ethoxyethyl methacrylate/methyl methacrylate copolymers, said film forming plastic material being skin adherent and washable upon drying.
2. As in claim I, a non-stingingwound dressing comprising plastic material in asolvent system, said plastic material selected from the group comprising poly(- lower alkyl)methacrylate, poly-2-alkoxyethyl methacrylate and copolymers thereof.
3. As in claim 1, a non-stinging wound dressing comprising a 525% solution of polyvinyl butyral in tertiary butyl alcohol.
4. As in claim 1, a non-stinging wound dressing comprising a 5-25% solution of ethyl cellulose in tertiary butyl alcohol.
5. As in claim 1, a non-stinging wound dressing comprising a 5-25% solution of polyvinylethyl ether in tertiary butyl alcohol.
6. As in claim 1, a non-stinging wound dressing comprising a 5.-25% solution of polyisobutylene in tertiary butyl alcohol.
7. As in claim 1, a non-stinging wound dressing comprising 5-25% solution of plastic material selected from the group comprising poly(lower alkyl)methacrylate, poly-2-alkoxyethyl methacrylate and copolymers thereof in a tertiary butyl alcohol/trichlorotrifluoroethane aolvent system.
8. As-in claim 1, a non-stinging wound dressing comprising 45 parts tertiary butyl alcohol, 40 parts trichlorotrifluoroethane, and 15 parts polyisobutyl methacrylate.
9. As in claim 1, a non-stinging wound dressing comprising 45 parts tertiary butyl alcohol, 40 parts trichlorotrifluoroethane, and I5 parts poly-n-butylmethacrylate.
10. As in claim 1, a non-stinging wound dressing comprising 45 parts tertiary butyl alcohol, 40 parts trichlorotrifluoroethane, l4 parts 95/5 copolymer of 2-ethoxyethyl methacrylate/methyl methacrylate, and dibutyl phthalate.
11. As in claim 1, a non-stinging wound dressing comprising a 525% solution of plastic material selected from the group comprising poly(lower alkyl)methacrylate, poly-2-alkoxyethyl methacrylate and copolymers thereof in tertiary butyl alcohol containing 05-30 per cent stinging solvent.
12. As in claim I, a non-stinging wound dressing comprising 60 parts tertiary butyl alcohol, 25 parts acetone, and 15 parts of 80/20 copolymer of isobutyl methacrylate/n-butyl methacrylate.
13. As in claim 1, a non-stinging wound dressing comprising 60 parts tertiary butyl alcohol, 25 parts ethyl acetate, and parts poly-Z-ethoxyethyl methacrylate.
14. As in claim 1, a non-stinging wound dressing further containing a medicinally active ingredient.
15. As in claim 1, a non-stinging wound dressing further containing a germicide.
16. As in claim 1, a non-stinging wound dressing comprising film forming plastic material dissolved in a solvent system, said solvent system containing stinging solvent and 70% or more non-stinging solvent, said non-stinging solvent consisting of tertiary butyl alcohol and a solvent selected from the group comprising straight and branched chain saturated hydrocarbons having 5-8 carbon atoms; saturated cyclic hydrocarbons having 5-8 carbon atoms and chlorofluoro substituted saturated hydrocarbons containing l-2 carbon atoms and mixtures thereof wherein the non-stinging solvent contains 50% or more tertiary butyl alcohol, said stinging solvent selected from the group comprising primary and secondary alcohols containing l-6 carbon atoms, ketones containing l-4 carbon atoms, esters of acids containing l-4 carbon atoms and alcohols containing l-6 carbon atoms, said film forming plastic material selected from the group comprising, N-butyl methacrylate, isobutyl methacrylate, 2-ethoxyethyl methacrylate, methyl methacrylate, polyvinyl butyral, ethyl cellulose, polyvinyl ethyl ether, polyisobutylene polymers and 80/20 isobutyl methacrylate/N- butyl methacrylate and 95/5 2-ethoxyethyl methacrylate/methyl methacrylate copolymers, said film forming plastic material being skin adherent and washable upon drying.
17. A non-stinging aerosol spray wound dressing comprising propellant gases together with film forming plastic material dissolved in a solvent system, said solvent system containing 70% or more non-stinging solvent, said non-stinging solvent consisting of tertiary butyl alcohol and solvent selected from the group comprising straight and branched chain saturated hydrocarbons having 5-8 carbon atoms, saturated cyclic hydrocarbons having 5-8 carbon atoms and chlorofluoro substituted saturated hydrocarbons containing l-2 carbonatoms and mixtures thereof wherein the nonstinging solvent contains 50% or more tertiary butyl alcohol, said film forming plastic material selected from the group comprising, N-butyl methacrylate, isobutyl methacrylate, 2-ethoxyethyl methacrylate, methyl methacrylate, polyvinyl butyral, ethyl cellulose, polyvinyl ethyl ether, polyisobutylene polymers and 80/20 isobutyl methacrylate/N-butyl methacrylate and 95/5 2-ethoxyethyl methacrylate/methyl methacrylate copolymers, said film forming plastic material being skin adherent and washable upon drying.
18. As in claim 17, a non-stinging aerosol spray wound dressing comprising:
tertiary butyl alcohol 2.54% Z-ethoxyethylmethacrylate 3.09% methyl methacrylate 0.01% ethyl acetate 0.55% amyl acetate 0.0l% l.l ,2-trichlorol ,2,2-trifluoroethane 24.80% trichlorofluoromethane 47.00%
p0 ymer content 19. As in claim 17, a non-stinging aerosol spray wound dressing further containing a germicide.
20. As in claim 17, a non-stinging aerosol spray wound dressing comprising propellant gases together with film forming plastic material dissolved in a solvent system, said solvent system containing stinging solvent and or more non-stinging solvent, said non-stinging solvent consisting of tertiary butyl alcohol and a solvent selected from the group comprising straight and branched chain saturated hydrocarbons having 5-8 carbon atoms, saturated cyclic hydrocarbons having 5-8 carbon atoms and chlorofluoro substituted saturated hydrocarbons containing l-2 carbon atoms and mixtures thereof wherein the non-stinging solvent contains 50% or more tertiary butyl. alcohol, said stinging solvent selected from the group comprising primary and secondary alcohols containing l-6 carbon atoms, ketones containing l-4 carbon atoms, esters of acids containing l-4 carbon atoms and alcohols containing l-6 carbon atoms, said film forming plastic material selected from the group comprising, N-butyl methacrylate, isobutyl methacrylate, Z-ethoxyethyl methacrylate, methyl methacrylate, -polyvinyl butyral, ethyl cellulose, polyvinylethyl ether,polyisobutylene polymers and /20 isobutyl methacrylate/N-butyl methacrylate and /5 2-ethoxyethyl methacrylate/methyl methacrylate copolymers, said film -forming plastic material being skin adherent and washable upon drying.
21. As in claim 17, a non-stinging aerosol spray wound dressing further containing a germicide, fungicide, antibiotic, steroid or local anesthetic.
22. A method for dre's'sin'g wounds comprising applying to the wound a thin film of a non-stinging wound dressing comprising film forming plastic material dissolved in a solvent system, said solvent system containing stinging solvent and 70% of'more non-stinging solvent, said non-stinging solvent consisting of tertiary butyl alcohol and a solvent selected from the group comprising straight and branched chain saturated hydrocarbons having 5-8 carbon atoms; saturated cyclic hydrocarbons having 5-8 carbon atoms and chlorofluoro substituted saturated hydrocarbons containing l2 carbon atoms and mixtures thereof wherein the non-stinging solvent contains 50% or more tertiary butyl alcohol, said stinging solvent selected from the group comprising primary and secondary alcohols containing l-6 carbon atoms,.ketones containing l-4 carbon atoms, esters of acids containing 1-4 carbon atoms and alcohols containing l-6 carbon atoms, said film forming plastic material selected from the group comprising N-butyl methacrylate, isobutyl methacrylate, 2-ethoxyethyl methacrylate, methyl methacrylate, polyvinyl butyral, ethyl cellulose, polyvinyl ethyl ether, polyisobutylene polymers and 80/20 isobutyl methacrylate/N-butyl methacrylate and 95/5 2-ethoxyethyl methacrylate/methyl methacrylate copolymers, said film forming plastic material being skin adherent and washable upon drying.

Claims (22)

1. A NON-STINGING WOUND DRESSING COMPRISING FILM FORMING PLASTIC MATERIAL DISSOLVED IN A SOLVENT SYSTEM, SAID SOLVENT SYSTEM CONTAINING 70% OR MORE NON-STINGING SOLVENT, SAID NON-STINGING SOLVENT CONSISTING OF TERTIARY BUTYL ALCOHOL AND SOLVENT SELECTED FROM THE GROUP COMPRISING STRAIGHT AND BRANCHED CHAIN SATURATED HYDROCARBONS HAVING 5-8 CARBON ATOMS, SATURATED CYCLIC HYDROCARBONS HAVING 5-8 CRBON ATOMS AND CHLOROFLUORO SUBSTITUTED SATURATED HYDROCARBONS CONTANING 1-2 CARBON ATOMS AND MIXTURES THEREOF WHEREIN THE NON-STINGING SOLVENT CONTAINS 50% OR MORE TERTIARY BUTYL ALCOHOL, SAID FILM FORMING PLASTIC MATERIAL SELECTED FROM THE GROUP COMPRISING, N-BUTYL METHACRYLATE, ISOBUTYL METHACRYLATE, 2-ETHOXYLETHYL METHACRYLATE, METHYL METHACRYLATE, POLYVINYL BUTYRAL, ETHYL CELLULOSE, POLYVINYL ETHYL ETHER, POLYSIOBUTYL ENE POLYMERS AND 80.20 ISOBUTYL METHACRYLATE /N-BUTYL METHACRYLATE AND 95/5 2-ETHOXYETHYL METHACRYLATE/METHYL METHACRYLATE COPOLYMERS, SAID FILM FORMING PLASTIC MATERIAL EING SKIN ADHERENT AND WASHABLE UPON DYING.
2. As in claim 1, a non-stinging wound dressing comprising plastic material in a solvent system, said plastic material selected from the group comprising poly(lower alkyl)methacrylate, poly-2-alkoxyethyl methacrylate and copolymers thereof.
3. As in claim 1, a non-stinging wound dressing comprising a 5-25% solution of polyvinyl butyral in tertiary butyl alcohol.
4. As in claim 1, a non-stinging wound dressing comprising a 5-25% solution of ethyl cellulose in tertiary butyl alcohol.
5. As in claim 1, a non-stinging wound dressing comprising a 5-25% solution of polyvinyl ethyl ether in tertiary butyl alcohol.
6. As in claim 1, a non-stinging wound dressing comprising a 5-25% solution of polyisobutylene in tertiary butyl alcohol.
7. As in claim 1, a non-stinging wound dressing comprising 5-25% solution of plastic material selected from the group comprising poly(lower alkyl)methacrylate, poly-2-alkoxyethyl methacrylate and copolymers thereof in a tertiary butyl alcohol/trichlorotrifluoroethane aolvent system.
8. As in claim 1, a non-stinging wound dressing comprising 45 parts tertiary butyl alcohol, 40 parts trichlorotrifluoroethane, and 15 parts polyisobutyl methacrylate.
9. As in claim 1, a non-stinging wound dressing comprising 45 parts tertiary butyl alcohol, 40 parts trichlorotrifluoroethane, and 15 parts poly-n-butyl methacrylate.
10. As in claim 1, a non-stinging wound dressing comprising 45 parts tertiary butyl alcohol, 40 parts trichlorotrifluoroethane, 14 parts 95/5 copolymer of 2-ethoxyethyl methacrylate/methyl meThacrylate, and dibutyl phthalate.
11. As in claim 1, a non-stinging wound dressing comprising a 5-25% solution of plastic material selected from the group comprising poly(lower alkyl)methacrylate, poly-2-alkoxyethyl methacrylate and copolymers thereof in tertiary butyl alcohol containing 0.5-30 per cent stinging solvent.
12. As in claim 1, a non-stinging wound dressing comprising 60 parts tertiary butyl alcohol, 25 parts acetone, and 15 parts of 80/20 copolymer of isobutyl methacrylate/n-butyl methacrylate.
13. As in claim 1, a non-stinging wound dressing comprising 60 parts tertiary butyl alcohol, 25 parts ethyl acetate, and 15 parts poly-2-ethoxyethyl methacrylate.
14. As in claim 1, a non-stinging wound dressing further containing a medicinally active ingredient.
15. As in claim 1, a non-stinging wound dressing further containing a germicide.
16. As in claim 1, a non-stinging wound dressing comprising film forming plastic material dissolved in a solvent system, said solvent system containing stinging solvent and 70% or more non-stinging solvent, said non-stinging solvent consisting of tertiary butyl alcohol and a solvent selected from the group comprising straight and branched chain saturated hydrocarbons having 5-8 carbon atoms; saturated cyclic hydrocarbons having 5-8 carbon atoms and chlorofluoro substituted saturated hydrocarbons containing 1-2 carbon atoms and mixtures thereof wherein the non-stinging solvent contains 50% or more tertiary butyl alcohol, said stinging solvent selected from the group comprising primary and secondary alcohols containing 1-6 carbon atoms, ketones containing 1-4 carbon atoms, esters of acids containing 1-4 carbon atoms and alcohols containing 1-6 carbon atoms, said film forming plastic material selected from the group comprising, N-butyl methacrylate, isobutyl methacrylate, 2-ethoxyethyl methacrylate, methyl methacrylate, polyvinyl butyral, ethyl cellulose, polyvinyl ethyl ether, polyisobutylene polymers and 80/20 isobutyl methacrylate/N-butyl methacrylate and 95/5 2-ethoxyethyl methacrylate/methyl methacrylate copolymers, said film forming plastic material being skin adherent and washable upon drying.
17. A non-stinging aerosol spray wound dressing comprising propellant gases together with film forming plastic material dissolved in a solvent system, said solvent system containing 70% or more non-stinging solvent, said non-stinging solvent consisting of tertiary butyl alcohol and solvent selected from the group comprising straight and branched chain saturated hydrocarbons having 5-8 carbon atoms, saturated cyclic hydrocarbons having 5-8 carbon atoms and chlorofluoro substituted saturated hydrocarbons containing 1-2 carbon atoms and mixtures thereof wherein the non-stinging solvent contains 50% or more tertiary butyl alcohol, said film forming plastic material selected from the group comprising, N-butyl methacrylate, isobutyl methacrylate, 2-ethoxyethyl methacrylate, methyl methacrylate, polyvinyl butyral, ethyl cellulose, polyvinyl ethyl ether, polyisobutylene polymers and 80/20 isobutyl methacrylate/N-butyl methacrylate and 95/5 2-ethoxyethyl methacrylate/methyl methacrylate copolymers, said film forming plastic material being skin adherent and washable upon drying.
18. As in claim 17, a non-stinging aerosol spray wound dressing comprising:
19. As in claim 17, a non-stinging aerosol spray wound dressing furthEr containing a germicide.
20. As in claim 17, a non-stinging aerosol spray wound dressing comprising propellant gases together with film forming plastic material dissolved in a solvent system, said solvent system containing stinging solvent and 70% or more non-stinging solvent, said non-stinging solvent consisting of tertiary butyl alcohol and a solvent selected from the group comprising straight and branched chain saturated hydrocarbons having 5-8 carbon atoms, saturated cyclic hydrocarbons having 5-8 carbon atoms and chlorofluoro substituted saturated hydrocarbons containing 1-2 carbon atoms and mixtures thereof wherein the non-stinging solvent contains 50% or more tertiary butyl alcohol, said stinging solvent selected from the group comprising primary and secondary alcohols containing 1-6 carbon atoms, ketones containing 1-4 carbon atoms, esters of acids containing 1-4 carbon atoms and alcohols containing 1-6 carbon atoms, said film forming plastic material selected from the group comprising, N-butyl methacrylate, isobutyl methacrylate, 2-ethoxyethyl methacrylate, methyl methacrylate, polyvinyl butyral, ethyl cellulose, polyvinyl ethyl ether, polyisobutylene polymers and 80/20 isobutyl methacrylate/N-butyl methacrylate and 95/5 2-ethoxyethyl methacrylate/methyl methacrylate copolymers, said film forming plastic material being skin adherent and washable upon drying.
21. As in claim 17, a non-stinging aerosol spray wound dressing further containing a germicide, fungicide, antibiotic, steroid or local anesthetic.
22. A method for dressing wounds comprising applying to the wound a thin film of a non-stinging wound dressing comprising film forming plastic material dissolved in a solvent system, said solvent system containing stinging solvent and 70% of more non-stinging solvent, said non-stinging solvent consisting of tertiary butyl alcohol and a solvent selected from the group comprising straight and branched chain saturated hydrocarbons having 5-8 carbon atoms; saturated cyclic hydrocarbons having 5-8 carbon atoms and chlorofluoro substituted saturated hydrocarbons containing 1-2 carbon atoms and mixtures thereof wherein the non-stinging solvent contains 50% or more tertiary butyl alcohol, said stinging solvent selected from the group comprising primary and secondary alcohols containing 1-6 carbon atoms, ketones containing 1-4 carbon atoms, esters of acids containing 1-4 carbon atoms and alcohols containing 1-6 carbon atoms, said film forming plastic material selected from the group comprising N-butyl methacrylate, isobutyl methacrylate, 2-ethoxyethyl methacrylate, methyl methacrylate, polyvinyl butyral, ethyl cellulose, polyvinyl ethyl ether, polyisobutylene polymers and 80/20 isobutyl methacrylate/N-butyl methacrylate and 95/5 2-ethoxyethyl methacrylate/methyl methacrylate copolymers, said film forming plastic material being skin adherent and washable upon drying.
US447032A 1973-03-02 1974-02-28 Non-stinging wound dressing containing tertiary butyl alcohol Expired - Lifetime US3928556A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
SE7302949A SE370626B (en) 1973-03-02 1973-03-02

Publications (1)

Publication Number Publication Date
US3928556A true US3928556A (en) 1975-12-23

Family

ID=20316788

Family Applications (1)

Application Number Title Priority Date Filing Date
US447032A Expired - Lifetime US3928556A (en) 1973-03-02 1974-02-28 Non-stinging wound dressing containing tertiary butyl alcohol

Country Status (14)

Country Link
US (1) US3928556A (en)
JP (1) JPS5046819A (en)
AR (1) AR200305A1 (en)
BE (1) BE811814A (en)
BR (1) BR7401566D0 (en)
DE (1) DE2409475A1 (en)
DK (1) DK131611C (en)
FR (1) FR2219793B1 (en)
GB (1) GB1417491A (en)
IE (1) IE38952B1 (en)
IL (1) IL44319A0 (en)
NL (1) NL7402893A (en)
SE (1) SE370626B (en)
ZA (1) ZA741320B (en)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0030576A1 (en) * 1978-09-22 1981-06-24 Masti-Kure Products Co., Inc. Film-forming alcoholic microbicidal teat dip and method of use thereof
US4548807A (en) * 1983-08-03 1985-10-22 Geoffrey J. Westfall Mastitis prevention
US4584192A (en) * 1984-06-04 1986-04-22 Minnesota Mining & Manufacturing Company Film-forming composition containing an antimicrobial agent and methods of use
US4716032A (en) * 1983-08-03 1987-12-29 Geoffrey J. Westfall Aerosol spray composition for mastitis prevention
US4921691A (en) * 1985-08-22 1990-05-01 Stockel Richard F Spray on wound dressing compositions
US5312688A (en) * 1988-08-10 1994-05-17 Teijin Limited Acaricide fiber material and process for producing same
US5948400A (en) * 1997-11-20 1999-09-07 Smith & Nephew Inc. Method of applying a pressure-sensitive adhesive wound dressing and water-based skin treatment composition
US6358443B1 (en) 1995-05-18 2002-03-19 Alkermes Controlled Therapeutics, Inc. Production scale method of forming microparticles
US6579469B1 (en) 1999-10-29 2003-06-17 Closure Medical Corporation Cyanoacrylate solutions containing preservatives
US20090324664A1 (en) * 2008-06-30 2009-12-31 Ulman John T Spray-on, non-woven fabric system and multilayer topical covering
CN102772801A (en) * 2012-08-10 2012-11-14 江苏长泰药业有限公司 Wound spray for treating bruises and preparation method of wound spray
CN103157126A (en) * 2012-03-26 2013-06-19 何星剑 Woundplast glue and preparing method thereof
US20160206777A1 (en) * 2007-03-16 2016-07-21 University Of Maryland, Baltimore Advanced functional biocompatible polymeric matrix used as a hemostatic agent and system for damaged tissues and cells
CN105920649A (en) * 2016-06-07 2016-09-07 东莞市万佳医疗科技有限公司 Water-proof and breathable wound protecting material and preparation method thereof
US20160331863A1 (en) * 2013-12-18 2016-11-17 Crawford Wondcare Ltd. Methods for the prevention and treatment of skin problems exacerbated by moisture and/or friction
US9717679B1 (en) * 2012-12-17 2017-08-01 Touchless Designs LLC Methods for the prevention and treatment of animal skin conditions
US11491255B2 (en) 2015-04-06 2022-11-08 3M Innovative Properties Company Removable film forming gel compositions and methods for their application

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2627343C3 (en) * 1976-06-18 1980-06-26 Hoechst Ag, 6000 Frankfurt Aerosol formulations and aerosol packs
US4379863A (en) * 1981-01-13 1983-04-12 C. R. Bard, Inc. Copolymer composition and delivery system for providing a protective barrier film for the skin
JPS61137814A (en) * 1984-12-07 1986-06-25 Yamada Seiyaku Kk Anti-inflammatory analgesic solution for external use
GB9408545D0 (en) * 1994-04-29 1994-06-22 Zyma Sa Compositions
CN106139239A (en) * 2016-07-12 2016-11-23 东莞市万佳医疗科技有限公司 Full-service fluid dressing and preparation method thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3297536A (en) * 1964-09-15 1967-01-10 Robert R Baron Method of treating skin and reducing pore size
US3568394A (en) * 1967-08-24 1971-03-09 Dart Ind Inc Method for preparing aerosol antiperspirant compositions
US3577376A (en) * 1967-12-06 1971-05-04 Gulf Oil Canada Ltd Interpolymerization of acrylamide,vinyl acetate and other monomers by using a solubilizing agent to dissolve the acrylamide in the vinyl acetate
US3577516A (en) * 1969-12-02 1971-05-04 Nat Patent Dev Corp Preparation of spray on bandage

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3297536A (en) * 1964-09-15 1967-01-10 Robert R Baron Method of treating skin and reducing pore size
US3568394A (en) * 1967-08-24 1971-03-09 Dart Ind Inc Method for preparing aerosol antiperspirant compositions
US3577376A (en) * 1967-12-06 1971-05-04 Gulf Oil Canada Ltd Interpolymerization of acrylamide,vinyl acetate and other monomers by using a solubilizing agent to dissolve the acrylamide in the vinyl acetate
US3577516A (en) * 1969-12-02 1971-05-04 Nat Patent Dev Corp Preparation of spray on bandage

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0030576A1 (en) * 1978-09-22 1981-06-24 Masti-Kure Products Co., Inc. Film-forming alcoholic microbicidal teat dip and method of use thereof
US4548807A (en) * 1983-08-03 1985-10-22 Geoffrey J. Westfall Mastitis prevention
US4716032A (en) * 1983-08-03 1987-12-29 Geoffrey J. Westfall Aerosol spray composition for mastitis prevention
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
US5312688A (en) * 1988-08-10 1994-05-17 Teijin Limited Acaricide fiber material and process for producing same
US6358443B1 (en) 1995-05-18 2002-03-19 Alkermes Controlled Therapeutics, Inc. Production scale method of forming microparticles
US5948400A (en) * 1997-11-20 1999-09-07 Smith & Nephew Inc. Method of applying a pressure-sensitive adhesive wound dressing and water-based skin treatment composition
US6579469B1 (en) 1999-10-29 2003-06-17 Closure Medical Corporation Cyanoacrylate solutions containing preservatives
US20160206777A1 (en) * 2007-03-16 2016-07-21 University Of Maryland, Baltimore Advanced functional biocompatible polymeric matrix used as a hemostatic agent and system for damaged tissues and cells
US10179145B2 (en) * 2007-03-16 2019-01-15 University Of Maryland, College Park Advanced functional biocompatible polymeric matrix used as a hemostatic agent and system for damaged tissues and cells
US20090324664A1 (en) * 2008-06-30 2009-12-31 Ulman John T Spray-on, non-woven fabric system and multilayer topical covering
CN103157126A (en) * 2012-03-26 2013-06-19 何星剑 Woundplast glue and preparing method thereof
CN102772801A (en) * 2012-08-10 2012-11-14 江苏长泰药业有限公司 Wound spray for treating bruises and preparation method of wound spray
CN102772801B (en) * 2012-08-10 2014-10-15 江苏长泰药业有限公司 Wound spray for treating bruises and preparation method of wound spray
US9717679B1 (en) * 2012-12-17 2017-08-01 Touchless Designs LLC Methods for the prevention and treatment of animal skin conditions
US20160331863A1 (en) * 2013-12-18 2016-11-17 Crawford Wondcare Ltd. Methods for the prevention and treatment of skin problems exacerbated by moisture and/or friction
US11491255B2 (en) 2015-04-06 2022-11-08 3M Innovative Properties Company Removable film forming gel compositions and methods for their application
CN105920649A (en) * 2016-06-07 2016-09-07 东莞市万佳医疗科技有限公司 Water-proof and breathable wound protecting material and preparation method thereof

Also Published As

Publication number Publication date
FR2219793B1 (en) 1977-09-16
IL44319A0 (en) 1974-05-16
BR7401566D0 (en) 1974-11-05
AR200305A1 (en) 1974-10-31
GB1417491A (en) 1975-12-10
DK131611B (en) 1975-08-11
BE811814A (en) 1974-09-04
DK131611C (en) 1976-01-19
FR2219793A1 (en) 1974-09-27
JPS5046819A (en) 1975-04-25
SE370626B (en) 1974-10-28
ZA741320B (en) 1975-04-30
IE38952B1 (en) 1978-07-05
DE2409475A1 (en) 1974-09-12
NL7402893A (en) 1974-09-04
AU6612374A (en) 1975-08-28
IE38952L (en) 1974-09-02

Similar Documents

Publication Publication Date Title
US3928556A (en) Non-stinging wound dressing containing tertiary butyl alcohol
US4303066A (en) Burn dressing
US3932602A (en) Non-stinging wound dressing
US4210633A (en) Flurandrenolide film formulation
US4272518A (en) Plastic wound bandage
US4287177A (en) Wound covering material
US11471481B2 (en) Rapid-deposition thin-film forming compositions as effective wound care treatment
US3880158A (en) Spray-spun bandage composition
US4374126A (en) Film forming antimicrobial material
US4393048A (en) Protective gel composition for wounds
JP3560977B2 (en) Gels for the treatment of skin disorders and for disinfecting their skin
US3577516A (en) Preparation of spray on bandage
AU614179B2 (en) Compositions and in situ methods for forming films on body tissue
US4073291A (en) Topical device for administering tretinoin
JPH06225932A (en) Composition that is possible to extrude for local or percutanous medicine distribution
JPS60150755A (en) Wound treating article made of synthetic resin and its treatment and use
EP0107376A1 (en) Polyvinylpyrrolidone gel dressings
Ågren et al. A comparative study of three occlusive dressings in the treatment of full-thickness wounds in pigs
US3079299A (en) Self-propelling medicinal ointment composition containing polyethylene and method ofapplication
WO2023198086A1 (en) Antibacterial healing-promoting functionalized dressing and preparation method therefor
JP6716841B2 (en) Hemostatic material
JPH0368369A (en) Liquid polymer bandage for dermic injury treat- ment
EP0489206A1 (en) Synthetic skin substitutes
Bakhrushina et al. Spray Film-Forming systems as promising topical in situ Systems: A review
CA2852210C (en) Composition and method for treating wounds