IP Library Granted Patent US 10,143,771
Granted Patent B2
US 10,143,771 · App. 14/598,016 · Granted Dec 4, 2018

Antioxidant and antimicrobial wound dressing materials

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Quick Facts
Patent No.
US 10,143,771
App. No.
14/598,016
Granted
Dec 4, 2018
Kind
B2
Abstract

A wound dressing material may include a polymeric substrate, a silver salt, and a dyestuff to photostabilize the silver salt. The substrate may include collagen and/or oxidized regenerated cellulose complexed to Ag+, and the dyestuff may, for example, be an aniline or acridine dye. Also disclosed are methods of making such materials, and wound dressings that include such materials.

Claims (55)

1. A method of manufacture of an antioxidant wound dressing material, comprising the steps of: dyeing a polymeric substrate material with a dye which stabilizes silver salts against photochemical reduction; and treating the substrate material with a silver salt dissolved or dispersed in water or an organic solvent.

2. The method according to claim 1 , wherein the polymeric substrate material comprises a solid bioabsorbable material.

3. The method according to claim 2 , wherein the solid bioabsorbable material comprises collagens, oxidized celluloses, chitosans, galactomannans, or glycosaminoglycans.

4. The method according to claim 1 , wherein the polymeric substrate material comprises celluloses, alginates, polyacrylates, polyurethanes, or polyamides.

5. The method according to claim 1 , wherein the polymeric substrate comprises an anionic polymer, and said silver salt comprises a salt of Ag + with the anionic polymer.

6. The method according to claim 1 , wherein the dye comprises an antioxidant dyestuff.

7. The method according to claim 6 , wherein the antioxidant dyestuff comprises gentian violet, aniline blue, methylene blue, crystal violet, acriflavine, 9-aminoacridine, acridine yellow, acridine orange, proflavin, quinacrine, brilliant green, trypan blue, trypan red, malachite green, azacrine, methyl violet, methyl orange, methyl yellow, ethyl violet, acid orange, acid yellow, acid blue, acid red, thioflavin, aiphazurine, indigo blue, or methylene green.

8. The method according to claim 1 , wherein the polymeric substrate consists essentially of a mixture of an oxidized cellulose with a collagen and/or a chitosan.

9. The method according to claim 1 , further comprising:

sterilizing the antioxidant wound dressing material; and

packaging the wound dressing material in a microorganism-impermeable container.

10. The method according to claim 1 , wherein the antioxidant wound dressing material has a free radical activity in a diphenylpicrylhydrazyl (DPPH) test for antioxidant activity of at least about 15%.

11. A wound dressing, comprising:

an antioxidant wound dressing material comprising a silver salt and an antioxidant dye; and

a backing sheet configured to be attached to the antioxidant wound dressing material to extend around edges of the antioxidant wound dressing material to form a backing sheet marginal region;

wherein the antioxidant dye is adapted to stabilize silver salts against photochemical reduction; and

the antioxidant dye is present in an amount of from about 0.2 wt. % to about 2 wt. % based on a dry weight of the antioxidant wound dressing material.

12. The wound dressing according to claim 11 , wherein the antioxidant wound dressing material and the backing sheet are sterile and packaged in a microorganism-impermeable container.

13. The wound dressing according to claim 11 , wherein the backing sheet is liquid impermeable.

14. The wound dressing according to claim 11 , wherein the backing sheet has a thickness in a range of approximately 10 to 1,000 μmicrometers.

15. The wound dressing according to claim 11 , wherein the backing sheet has a thickness in a range of approximately 100 to 500 μmicrometers.

16. The wound dressing according to claim 11 , wherein the backing sheet comprises a polymer comprising polyurethanes poly alkoxyalkyl acrylates methacrylates.

17. The wound dressing according to claim 16 , wherein the backing sheet comprises a continuous layer of a high density blocked polyurethane foam.

18. The wound dressing according to claim 11 , further comprising an absorbent layer disposed between the antioxidant wound dressing material and the backing sheet.

19. The wound dressing according to claim 18 , wherein the absorbent layer comprises gauzes, nonwoven fabrics, superabsorbents, or hydrogels.

20. The wound dressing according to claim 18 , wherein the absorbent layer comprises an open-celled hydrophilic polyurethane foam.

21. The wound dressing according to claim 11 , further comprising an adhesive layer disposed between the antioxidant wound dressing material and the backing sheet.

22. The wound dressing according to claim 11 , wherein a removable cover sheet is disposed on a wound-facing surface of the wound dressing.

23. The wound dressing according to claim 11 , wherein the backing sheet is coated with a pressure sensitive adhesive.

24. The wound dressing according to claim 11 , wherein the antioxidant wound dressing material is in the form of a continuous solid sheet, a solid sheet with at least one aperture, a web, a woven fabric, a knitted fabric, a nonwoven fabric, a freeze-dried sponge or a solvent-dried sponge.

25. The wound dressing according to claim 11 , wherein the antioxidant wound dressing material comprises from about 0.01 wt. % to about 5 wt. % of silver, based on a dry weight of the antioxidant wound dressing material.

26. A wound dressing, comprising:

an antioxidant wound dressing material, comprising:

a silver salt, and

a dye which stabilizes the silver salt against photochemical reduction; and

a backing sheet configured to be attached to the antioxidant wound dressing material and to extend around edges of the antioxidant wound dressing material to form a margin.

27. A wound dressing, comprising:

an antioxidant wound dressing material comprising from about 0.01 wt. % to about 5 wt. % of silver, based on a dry weight of the antioxidant wound dressing material; and

a backing sheet configured to be attached to the antioxidant wound dressing material and to extend around edges of the antioxidant wound dressing material to form a margin.

28. A wound dressing, comprising:

an antioxidant wound dressing material comprising a dye adapted to stabilize silver salts against photochemical reduction; and

a backing sheet configured to be attached to the antioxidant wound dressing material and to extend around edges of the antioxidant wound dressing material to form a margin.

29. The wound dressing of claim 28 , wherein the dye is present in an amount of from about 0.2 wt. % to about 2 wt. % based on a dry weight of the antioxidant wound dressing material.

30. The wound dressing of claim 11 , wherein the antioxidant dye comprises gentian violet, aniline blue, methylene blue, crystal violet, acriflavine, 9-aminoacridine, acridine yellow, acridine orange, proflavin, quinacrine, brilliant green, trypan blue, trypan red, malachite green, azacrine, methyl violet, methyl orange, methyl yellow, ethyl violet, acid orange, acid yellow, acid blue, acid red, thioflavin, alphazurine, indigo blue, or methylene green.

31. The wound dressing of claim 11 , wherein the antioxidant dye has an antioxidant activity of at least about 15% in the diphenylpicrylhydrazyl (DPPH) test.

32. The wound dressing of claim 11 , wherein the silver salt comprises silver oxide, silver chromate, silver allantoinate, silver borate, silver glycerolate, silver nitrate, silver acetate, silver chloride, silver sulfate, silver lactate, silver bromide, silver iodide, silver carbonate, silver citrate, silver laurate, silver deoxycholate, silver salicylate, silver p-aminobenzoate, or silver p-aminosalicylate.

33. The wound dressing of claim 26 , wherein the dye comprises gentian violet, aniline blue, methylene blue, crystal violet, acriflavine, 9-aminoacridine, acridine yellow, acridine orange, proflavin, quinacrine, brilliant green, trypan blue, trypan red, malachite green, azacrine, methyl violet, methyl orange, methyl yellow, ethyl violet, acid orange, acid yellow, acid blue, acid red, thioflavin, alphazurine, indigo blue, or methylene green.

34. The wound dressing of claim 26 , wherein the dye has an antioxidant activity of at least about 15% in the diphenylpicrylhydrazyl (DPPH) test.

35. The wound dressing of claim 26 , wherein the silver salt comprises silver oxide, silver chromate, silver allantoinate, silver borate, silver glycerolate, silver nitrate, silver acetate, silver chloride, silver sulfate, silver lactate, silver bromide, silver iodide, silver carbonate, silver citrate, silver laurate, silver deoxycholate, silver salicylate, silver p-aminobenzoate, or silver p-aminosalicylate.

36. The wound dressing of claim 27 , wherein the dye comprises gentian violet, aniline blue, methylene blue, crystal violet, acriflavine, 9-aminoacridine, acridine yellow, acridine orange, proflavin, quinacrine, brilliant green, trypan blue, trypan red, malachite green, azacrine, methyl violet, methyl orange, methyl yellow, ethyl violet, acid orange, acid yellow, acid blue, acid red, thioflavin, alphazurine, indigo blue, or methylene green.

37. The wound dressing of claim 27 , wherein the dye has an antioxidant activity of at least about 15% in the diphenylpicrylhydrazyl (DPPH) test.

38. The wound dressing of claim 27 , wherein the silver salt comprises silver oxide, silver chromate, silver allantoinate, silver borate, silver glycerolate, silver nitrate, silver acetate, silver chloride, silver sulfate, silver lactate, silver bromide, silver iodide, silver carbonate, silver citrate, silver laurate, silver deoxycholate, silver salicylate, silver p-aminobenzoate, or silver p-aminosalicylate.

39. The wound dressing of claim 28 , wherein the dye comprises gentian violet, aniline blue, methylene blue, crystal violet, acriflavine, 9-aminoacridine, acridine yellow, acridine orange, proflavin, quinacrine, brilliant green, trypan blue, trypan red, malachite green, azacrine, methyl violet, methyl orange, methyl yellow, ethyl violet, acid orange, acid yellow, acid blue, acid red, thioflavin, alphazurine, indigo blue, or methylene green.

40. The wound dressing of claim 28 , wherein the dye has an antioxidant activity of at least about 15% in the diphenylpicrylhydrazyl (DPPH) test.

41. The wound dressing of claim 28 , wherein the silver salt comprises silver oxide, silver chromate, silver allantoinate, silver borate, silver glycerolate, silver nitrate, silver acetate, silver chloride, silver sulfate, silver lactate, silver bromide, silver iodide, silver carbonate, silver citrate, silver laurate, silver deoxycholate, silver salicylate, silver p-aminobenzoate, or silver p-aminosalicylate.

Assignments (13)
RELEASE OF SECURITY INTEREST IN PATENTS Recorded Nov 7, 2019
From: WILMINGTON TRUST, NATIONAL ASSOCIATION
To: KCI USA, INC.; KCI LICENSING, INC.
Reel/Frame 050966/0547 →
RELEASE OF SECURITY INTEREST IN PATENTS Recorded Nov 6, 2019
From: WILMINGTON TRUST, NATIONAL ASSOCIATION
To: KINETIC CONCEPTS, INC.; KCI USA, INC.; ACELITY L.P. INC.; CHIRON HOLDINGS, INC.; CHIRON TOPCO, INC.; KCI ANIMAL HEALTH, LLC; KCI HOLDING COMPANY, INC.; KCI HOMECARE, INC.; KCI IMPORTS, INC.; KCI INTERNATIONAL, INC.; KCI LICENSING, INC.; KCI PROPERTIES LIMITED; KCI REAL HOLDINGS, L.L.C.; KCI REAL PROPERTY LIMITED; KCI USA REAL HOLDINGS, L.L.C.; TECHNIMOTION, LLC
Reel/Frame 050945/0278 →
RELEASE OF SECURITY INTEREST Recorded Oct 11, 2019
From: BANK OF AMERICA, N.A.
To: KCI USA, INC.
Reel/Frame 050710/0955 →
RELEASE OF SECURITY INTEREST REEL/FRAME 040098/0268 Recorded Feb 8, 2017
From: WILMINGTON TRUST
To: KCI USA, INC.
Reel/Frame 041666/0320 →
SECURITY AGREEMENT Recorded Feb 7, 2017
From: KCI USA, INC., AS GRANTOR
To: BANK OF AMERICA, N.A., AS COLLATERAL AGENT
Reel/Frame 041650/0013 →
LIMITED THIRD LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Oct 7, 2016
From: KCI USA, INC.; LIFECELL CORPORATION; KCI LICENSING, INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 040291/0237 →
SECOND LIEN SECURITY AGREEMENT Recorded Sep 21, 2016
From: KCI USA, INC.; LIFECELL CORPORATION; KCI LICENSING, INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 040098/0268 →
SECURITY INTEREST Recorded Feb 17, 2016
From: KINETIC CONCEPTS, INC.; KCI USA, INC.; ACELITY L.P. INC.; CHIRON HOLDINGS, INC.; CHIRON TOPCO, INC.; KCI ANIMAL HEALTH, LLC; KCI HOLDING COMPANY, INC.; KCI HOMECARE, INC.; KCI IMPORTS, INC.; KCI INTERNATIONAL, INC.; KCI LICENSING, INC.; KCI PROPERTIES LIMITED; KCI REAL HOLDINGS, L.L.C.; KCI REAL PROPERTY LIMITED; KCI USA REAL HOLDINGS, L.L.C.; LIFECELL CORPORATION; TECHNIMOTION, LLC
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 037845/0497 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 25, 2015
From: ETHICON, INC.; JOHNSON & JOHNSON MEDICAL LIMITED
To: SYSTAGENIX WOUND MANAGEMENT IP CO. B.V.
Reel/Frame 036410/0439 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 25, 2015
From: ETHICON, INC.; JOHNSON & JOHNSON; JOHNSON & JOHNSON MEDICAL LIMITED; JOHNSON & JOHNSON MEDICAL B.V.; JANSSEN PHARMACEUTICA N.V.; CILAG AG; CILAG HOLDING AG; JEVCO LIMITED
To: SYSTAGENIX WOUND MANAGEMENT (US), INC.; SYSTAGENIX WOUND MANAGEMENT IP CO. B.V.
Reel/Frame 036414/0755 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 25, 2015
From: ADDISON, DEBORAH; GREENHALGH, DAVID; CULLEN, BREDA MARY
To: ETHICON, INC.
Reel/Frame 036409/0085 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 25, 2015
From: ETHICON, INC.; JOHNSON & JOHNSON MEDICAL LIMITED
To: SYSTAGENIX WOUND MANAGEMENT (US), INC.
Reel/Frame 036409/0371 →
MERGER AND CHANGE OF NAME Recorded Aug 25, 2015
From: SYSTAGENIX WOUND MANAGEMENT (US), INC.; KCI USA, INC.
To: KCI USA, INC.
Reel/Frame 036415/0139 →