Inherently antimicrobial quaternary amine hydrogel wound dressings

• US 6,800,278 B1
• Filed: 02/14/2000
• Issued: 10/05/2004
• Est. Priority Date: 10/28/1996
• Status: Expired due to Term

• Current Assignee: Avent Incorporated (Avanos Medical, Inc.)
• Original Assignee: Ballard Medical Products (Kimberly-Clark Corporation)
• Inventors: Rouns, Cameron G., Perrault, James J.
• Primary Examiner(s): Padmanabhan, Sreeni
• Assistant Examiner(s): JUSTICE, GINA CHIEUN YU
• Application Number:
  US09/503,770
• Time in Patent Office: 1,695 Days
• Field of Search: 424/78.06, 424/447, 424/409, 424/405, 424/484, 424/486, 424/487
• US Class Current: 424/78.06
• CPC Class Codes: A01N 2300/00 Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
• CPC Class Codes: A01N 25/10 Macromolecular compounds
• CPC Class Codes: A01N 33/12 Quaternary ammonium compounds
• CPC Class Codes: A01N 37/12 containing the group , wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
• CPC Class Codes: A01N 37/20 containing the group , wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
• CPC Class Codes: A61B 5/259 using conductive adhesive means, e.g. gels
• CPC Class Codes: A61K 31/785 Polymers containing nitrogen
• CPC Class Codes: A61K 47/32 Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers , poly(meth)acrylates, or polyvinyl pyrrolidone
• CPC Class Codes: A61K 9/0009 involving or responsive to electricity, magnetism or acoustic waves; Galenical aspects of sonophoresis, iontophoresis, electroporation or electroosmosis microelectromechanical systems A61K9/0097
• CPC Class Codes: A61K 9/0014 Skin, i.e. galenical aspects of topical compositions non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00
• CPC Class Codes: A61L 15/46 Deodorants or malodour counteractants, e.g. to inhibit the formation of ammonia or bacteria
• CPC Class Codes: A61L 15/60 Liquid-swellable gel-forming materials, e.g. super-absorbents
• CPC Class Codes: A61L 2300/208 Quaternary ammonium compounds
• CPC Class Codes: A61L 2300/404 Biocides, antimicrobial agents, antiseptic agents
• CPC Class Codes: C08F 20/34 Esters containing nitrogen , e.g. N,N-dimethylaminoethyl (meth)acrylate
• CPC Class Codes: C08F 20/60 containing nitrogen in addition to the carbonamido nitrogen
• CPC Class Codes: C08L 33/14 of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
• CPC Class Codes: H01B 1/122 Ionic conductors

Abstract

A composition and method for treating a wound with an inherently antimicrobial dressing. The dressing is a hydrogel containing from about 15 to 95 percent, and preferably from about 61 to 90 percent, by weight of a cationic quaternary amine acrylate polymer prepared by the polymerization of acryloyloxyethyl(or propyl)-trialkyl(or aryl)-substituted ammonium salts or acrylamidoethyl(or propyl)-trialkyl(or aryl)-substituted ammonium salts. The antimicrobial hydrogels are non-irritating to the wound, absorb wound exudate, and, due to the inherently antimicrobial properties, enhance the sterile environment around the wound. The hydrogels have sufficient adhesive properties that loose contact with the wound is assured but can also be removed without leaving any gel residue on the wound. The wound dressings are preferably formed on a substrate, such as a web or patch, for ease in application to and removal from the wound. If desired, additional antimicrobial or other pharmaceutically active agents can also be incorporated into the hydrogel structure.

Claims

1. A wound dressing adapted to cover and contact a wound, said wound dressing comprising a support structure in communication with a cationic aqueous hydrogel that comprises from about 15 to about 95 percent by weight of an inherently antimicrobial quaternary amine acrylate polymer having the formula:

wherein n is an integer of 2 to 3;

R′

, R′ and

R′

″

are independently selected from the group consisting of H, C₁ to C₈ alkyl, phenyl, tolyl, and benzyl;

X is selected from the group consisting of O and NH;

Y⁻

is selected from the group consisting of Cl⁻

, Br⁻

, HSO₄⁻

, and CH₃SO₄⁻

and m is an integer greater than 50,000.

2. A wound dressing as defined in claim 1, wherein R′

, R″

are methyl and R′

″

is benzyl.

3. A wound dressing as defined in claim 1, wherein R′

, R″ and

R′

″

are methyl.

4. A wound dressing as defined in claim 1, wherein X is O.

5. A wound dressing as defined in claim 1, wherein X is NH.

6. A wound dressing as defined in claim 1, wherein Y⁻

is Cl⁻

.

7. A wound dressing as defined in claim 1, wherein n is 2.

8. A wound dressing as defined in claim 1, wherein n is 3.

9. A wound dressing as defined in claim 1, wherein said acrylate polymer is formed from a monomer selected from the group consisting of acryloyloxyethyltrimethyl ammonium chloride, acryloyloxyethyltrimethyl ammonium methyl sulfate, acrylamidopropyltrimethyl ammonium chloride, acryloxyethyldimethylbenzyl ammonium chloride, and combinations thereof.

10. A wound dressing as defined in claim 1, wherein said support structure is affixed to said hydrogel.

11. A wound dressing as defined in claim 10, wherein said support structure includes a web or fibril material.

12. A wound dressing as defined in claim 10, wherein said support structure includes an impermeable backing.

13. A wound dressing as defined in claim 1, wherein said hydrogel comprises from about 61 to about 90 percent by weight of said acrylate polymer.

14. A wound dressing as defined in claim 1, wherein said hydrogel comprises from about 65 to about 75 percent by weight of said acrylate polymer.

15. A wound dressing comprising a support structure and a cationic aqueous hydrogel affixed to said support structure and adapted to cover a wound, said hydrogel comprising from about 61 to about 90 percent by weight of an inherently antimicrobial quaternary amine acrylate polymer having the formula:

wherein n is an integer of 2 to 3;

R′

, R″ and

R′

″

are independently selected from the group consisting of H, C₁ to C₈ alkyl, phenyl, tolyl, and benzyl;

X is selected from the group consisting of O and NH;

Y⁻

is selected from the group consisting of Cl⁻

, Br⁻

, HSO₄⁻

, and CH₃SO₄⁻

and m is an integer greater than 50,000.

16. A wound dressing as defined in claim 15, wherein X is O.

17. A wound dressing as defined in claim 15, wherein X is NH.

18. A wound dressing as defined in claim 15, wherein said hydrogel comprises from about 65 to about 75 percent by weight of said acrylate polymer.

19. A wound dressing as defined in claim 15, wherein n is 2.

20. A wound dressing as defined in claim 15, wherein n is 3.

21. A wound dressing as defined in claim 15, wherein said acrylate polymer is formed from a monomer selected from the group consisting of acryloyloxyethyltrimethyl ammonium chloride, acryloyloxyethyltrimethyl ammonium methyl sulfate, acrylamidopropyltrimethyl ammonium chloride, acryloxyethyldimethylbenzyl ammonium chloride, and combinations thereof.