Synthetic resin wound dressing and method of treatment using same

• US 4,563,184 A
• Filed: 10/17/1983
• Issued: 01/07/1986
• Est. Priority Date: 10/17/1983
• Status: Expired due to Term

• Current Assignee: Enquay, Inc.
• Original Assignee: Bernard Korol
• Inventors: Korol, Bernard
• Primary Examiner(s): Hoke, Veronica P.
• Application Number:
  US06/542,754
• Time in Patent Office: 813 Days
• Field of Search: 523/111, 523/122, 128/156, 128/334, 128/335.5, 424/28, 424/33, 424/81, 524/173, 524/560
• US Class Current: 602/52
• CPC Class Codes: A61L 15/24 Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof A61L15/225 takes precedence
• CPC Class Codes: A61L 15/44 Medicaments
• CPC Class Codes: A61L 2300/414 Growth factors
• CPC Class Codes: A61L 2300/602 Type of release, e.g. controlled, sustained, slow
• CPC Class Codes: A61L 26/0014 obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61L 26/0066 Medicaments; Biocides
• CPC Class Codes: A61L 26/008 Hydrogels or hydrocolloids
• CPC Class Codes: C08K 5/0008 Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
• CPC Class Codes: C08K 5/0016 Plasticisers
• CPC Class Codes: C08L 33/04 Homopolymers or copolymers of esters C08L43/04 takes precedence
• CPC Class Codes: C08L 33/14 of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen

Abstract

A synthetic resin wound dressing (e.g., a burn wound dressing) is disclosed consisting essentially of a polymer, such as poly(2-hydroxyethylmethacrylate), referred to as PHEMA, an organic solvent, such as polyethylene glycol (PEG), and a hydrogen binding plasticizer, such as dimethylsulfoxide (DMSO). The plasticizer regulates the set-up time of the synthetic resin so that the more plasticizer present, the shorter the set-up time. The dressing may be applied to the wound site in the form of a paste for the in situ curing or setting thereof, or the dressing may be preformed and then applied to the wound site. A variety of drug agents (e.g., silver sulfadiazine) may be incorporated in the synthetic resin so as to result in the time released administration of the drug agent to the area of the skin (e.g., a burn wound site or the like) covered by the wound dressing. A method of treatment using this dressing is also disclosed.

Claims

1. In combination with a synthetic resin wound dressing of the type wherein a particulate, hydrophilic, water swellable polymer of an acrylate or acrylamide, is combined with an inert, non-toxic, water miscible organic solvent of polyethylene glycol, capable of forming a paste with said polymer, the improvement which comprises, a hydrogen bonding plasticizer of dimethylsulfoxide mixed with the combined polymer and solvent, with said polymer ranging between about 30%-55% by weight of said dressing, with said solvent ranging between about 20%-60% by weight of said dressing, and with said plasticizer being present in a plasticizing amount ranging up to about 20% by weight of said dressing.

4. A synthetic resin wound dressing as set forth in claim 1, 2, or 3 and further comprising as a further ingredient a medicament agent, said medicament agent is a material selected from the group consisting of a germicide, a fungicide, an antimicrobial agent, an antibiotic, an analgesic, a hormone agent, an anti-inflammatory agent, a cardiovascular agent, an anticonvulsant agent, a pulmonary agent, and a muscle relaxant.

6. The synthetic resin wound dressing as set forth in claim 1, 2, or 3 wherein said polymer is poly(2-hydroxyethylmethacrylate), said solvent being polyethylene glycol hving a molecular weight ranging between about 200-2000, and said hydrogen bonding plasticizer being dimethylsulfoxide with the amount of said plasticizer directly controlling the set-up of the composition in forming a substantially occlusive film, and with the length of the set-up time decreasing as the quantity of the plasticizer increases such that set-up times of less than about 30 seconds or less may be realized when the above-stated maximum quantity of said plasticizer is present, to about 45 minutes when a minimum amount of said plasticizer is present.

7. A synthetic resin wound dressing as set forth in claim 1, 2, or 3 wherein said polymer is poly(2-hydroxyethylmethacrylate).

8. A synthetic resin wound dressing as set forth in claim 7 wherein said solvent is polyethylene glycol having a molecular weight ranging between about 200-2000.

9. A synthetic resin wound dressing as set forth in claim 1, 2, or 3 wherein said bandage-type dressing comprises a substrate having a layer of said paste applied to one face thereof.

10. A synthetic resin wound dressing as set forth in claim 9 wherein said substrate is a biaxially stretchable substrate.

11. A synthetic resin wound dressing as set forth in claim 1, 2, or 3 wherein said polymer is a polymer of

hydroxy(C₂ -C₄ -alkyl)methacrylate, hydroxy(C₂ -C₄ alkyl)

acrylate, hydroxy(C₂ -C₄ alkoxyC₂ -C₄ -alkyl)methacrylate,

hydroxy(C₂ -C₄ alkoxyC₂ -C₄ alkyl)acrylate,

alkoxy(C₂ -C₄ alkoxyC₂ -C₄ alkyl)methacrylate,

alkoxy(C₂ -C₄ alkoxyC₂ -C₄ alkyl)acrylate,

N-(C₁ -C₄ alkyl)acrylamide, N-(C₁ -C₄ alkyl)methacrylamide,

N,N-di(C₁ -C₄ -alkyl)acrylamide,

N,N-(di(C₁ -C₄ alkyl)methacrylamide,

vicinal-epoxy(C₁ -C₄ alkyl)methacrylate, or

vicinal-epoxy(C₁ -C₄ alkyl)acrylate.

12. A synthetic resin wound dressing as set forth in claim 11 wherein said polymer is at least slightly crosslinked and has a molecular weight of at least 50,000.

13. A synthetic resin wound dressing as set forth in claim 1, 2, or 3 wherein said plasticizer is a liquid having a solubility parameter ranging between about 10.7 to about 12.6.

14. A synthetic resin wound dressing as set forth in claim 1, 2, or 3 wherein said solvent is polyethylene glycol of the general formula H(OCH₂ CH₂)_n OH, where n is greater than or equal to 4.

15. A synthetic resin wound dressing as set forth in claim 14 wherein said polyethylene glycol solvent has a molecular weight ranging between about 200-2000, and has a boiling point of about 200°

C.

16. A synthetic resin wound dressing as set forth in claim 15 wherein said polyethylene glycol has a molecular weight ranging between about 200-800.

17. A synthetic resin wound dressing as set forth in claim 4 wherein said antimicrobial agent is silver sulfadiazine.

18. A synthetic resin wound dressing as set forth in claim 17 wherein said silver sulfadiazine is present in said wound dressing ranging between about 0.5 to about 7% by weight.

19. A synthetic resin wound dressing as set forth in claim 4 wherein said cardiovascular agent is nitroglycerine.

20. A synthetic resin wound dressing as set forth in claim 19 wherein said nitroglycerine is present in said wound dressing ranging between about 0.5 to about 10% by weight.

21. A synthetic resin wound dressing as set forth in claim 4 wherein said antimicrobial agent is nitrofurazone.

22. A synthetic resin wound dressing as set forth in claim 21 wherein said nitrofurazone is present in said wound dressing ranging between about 0.5 to about 10% by weight.

23. A synthetic resin wound dressing as set forth in claim 4 wherein said antimicrobial agent is silver nitrate.

24. A synthetic resin wound dressing as set forth in claim 23 wherein said silver nitrate is present in said wound dressing ranging between about 0.5 to about 10% by weight.

25. A synthetic resin wound dressing as set forth in claim 4 wherein said antimicrobial agent consists essentially of silver sulfadiazine, nitrofurazone, or silver nitrate with the weight of said antimicrobial agent ranging between about 0.5 to about 10% by weight of said dressing.

26. A synthetic resin wound dressing as set forth in claim 4 wherein said antimicrobial agent is mafenide acetate.

27. A synthetic resin wound dressing as set forth in claim 26 wherein said mafenide acetate is present in said wound dressing ranging between about 0.5 to about 10% by weight.

2. A synthetic resin wound dressing of the bonding type comprising a particulate, hydrophilic, water swellable polymer of an acrylate or acrylamide, an inert, non-toxic water miscible organic solvent of polyethylene glycol, the improvement which comprises, a hydrogen bonding plasticizer mixed with said polymer and solvent, said plasticizer is a material selected from the group consisting of dimethylsulfoxide, dimethylphthalate, 2,3-butylene carbonate, dimethylformamide, dimethyltetramethylene sulfone, diethylsulfone, methylene glycolate, methylpropyl sulfone, and butyrolactone, said polymer ranging between 30%-55% by weight of said dressing, with said solvent ranging between about 20%-60% by weight of said dressing, and said plasticizer ranging up to about 20% by weight of said dressing.

5. A synthetic resin wound dressing as set forth in claim 2 or 3 and wherein said dressing comprises, when said polymer, solvent, and hydrogen bonding plasticizer are mixed, a cured bandage type dressing having a controlled increased flexibility, elasticity, and surface adhesion, and which may be stored in bandage type form until usage.

3. A synthetic resin wound dressing of the preformed film type bandage comprising a particulate, hydrophilic, water swellable polymer of an acrylate or acrylamide, an inert nontoxic, water miscible organic solvent of polyethylene glycol, the improvement which comprises, a hydrogen bonding plasticizer of dimethylsulfoxide mixed with the combined polymer and solvent, said combination of polymer, solvent, and plasticizer being mixed in combination and cured to form a bandage type dressing with controlled flexibility and elasticity, and having an adherent surface, with said polymer ranging between about 30%-55% by weight of said dressing, with said solvent ranging between about 20%-60% by weight of said dressing, and with said plasticizer being present in a plasticizing amount ranging up to about 20% by weight of said dressing.

28. A synthetic resin wound dressing comprising a preformed polymer film of poly(hydroxyethylmethacrylate), a solvent of polyethylene glycol, a hydrogen bonding plasticizer of dimethylsulfoxide, and a medicinal agent of silver sulfadiazine, nitrofurazone, silver nitrate, or mafenide acetate, wherein said poly(hydroxyethylmethacrylate) ranges between 30%-55% by weight of said dressing, said polyethylene glycol ranges between about 20%-60% by weight of said dressing, said dimethylsulfoxide being present in a plasticizing amount ranges up to about 20% by weight of said dressing, said medicinal agent, or combinations thereof, ranges between about 0.5% to about 10% by weight of said dressing, and wherein said composition is mixed and formed into a precured bandage type wound dressing.

29. A process of treating a wound site comprising applying a synthetic resin film type bandage wound dressing to the wound site, said wound dressing consisting essentially of a particulate hydrophilic, water swellable polymer of an acrylate or acrylamide, an inert, non-toxic, water miscible, organic solvent of polyethylene glycol, and a hydrogen bonding plasticizer, said plasticizer selected from the group consisting of dimethylsulfoxide, dimethylphthalate, 2,3-butylene carbonate, dimethylformamide, dimethyltetramethylene sulfone, diethylsulfone, methylene glycolate, methylpropyl sulfone, and butryolactone, said polymer, solvent, and plasticizer capable of forming a flexible adherent film dressing, the said polymer ranging between about 30%-55% by weight of said dressing, with said solvent ranging between about 20%-60% by weight of said dressing, and with said plasticizer being present in a plasticizing amount ranging up to about 20% by weight of said dressing.

30. The process of claim 29 wherein, said polymer, solvent, and plasticizer are initially mixed, a settable paste results which may be formed into a flexible, elastic and adherent film type bandage for application directly on the wound site.

31. The process of claim 30 further comprising applying said mixture to an adherent substrate and permitting said mixture to cure thereby to form said preformed bandage-type dressing.

32. The process of claim 30 further comprising applying said mixture to a non-adherent surface and permitting said mixture to cure thereby to form said preformed bandage-type dressing.

33. The process of claim 29 further comprising adding a medicament agent, such as a germicide, a fungicide, an antimicrobial agent, an antibiotic, an analgesic, a hormone agent, an anti-inflammatory agent, a cardiovascular agent, an anticonvulsant agent, a pulmonary agent, or a muscle relaxant.

34. The process of claim 29 wherein said plasticizer is from the group of dimethylsulfoxide, dimethylphthalate, 2,3-butylene carbonate, dimethylformamide, dimethyltetramethylene sulfone, diethyl sulfone, methylene glycolate, methyl propyl sulfone or butyrolactone.

35. The process of claim 29 wherein said polymer is poly(2-hydroxyethylmethacrylate).

36. The process of claim 35 wherein said solvent is polyethylene glycol having a molecular weight ranging between about 200-2,000.

37. The process of claim 36 wherein said plasticizer is preferably dimethylsulfoxide.

38. The process of claim 29 wherein the dressing is applied to a burn wound site.

39. The process of claim 38 wherein the dressing comprises an antimicrobial agent such as silver sulfadiazine, silver nitrate, nitrofurazone, mafenide acetate, or mixtures thereof, said antimicrobial agent ranging up to about 10% by weight of said dressing.