Skin adhesive hydrogel, its preparation and uses

• US 5,306,504 A
• Filed: 12/09/1992
• Issued: 04/26/1994
• Est. Priority Date: 12/09/1992
• Status: Expired due to Fees

• Current Assignee: Ridge Scientific Enterprises, Inc.
• Original Assignee: Paper Manufacturers Company
• Inventors: Lorenz, Donald H.
• Primary Examiner(s): Page, Thurman K.
• Assistant Examiner(s): VENKAT, JYOTHSNA A
• Application Number:
  US07/987,642
• Time in Patent Office: 503 Days
• Field of Search: 424/443, 424/445, 424/448, 424/449, 424/401, 424/486, 424/487
• US Class Current: 424/449
• CPC Class Codes: A61F 13/023 wound covering film layers without a fluid retention layer
• CPC Class Codes: A61F 13/0246 characterised by the skin-adhering layer
• CPC Class Codes: A61F 2013/0037 for cosmesis
• CPC Class Codes: A61F 2013/00523 with hydrogel wound bandages with alginate A61F2013/00229; adhesive for plasters; with hydrogel A61F2013/00676; water-based A61F2013/00689; for use on mucosae A61F2013/00714; for use on wounds A61F2013/00719; wound humidity control with hydrocolloids or superabsorbers A61F2013/00748; with absorbent adhesives A61F2013/00757; with fumed silica A61F2013/00787; with viscoelastic oil-elastomer gel A61F2013/00893
• CPC Class Codes: A61F 2013/00527 artificial skin
• CPC Class Codes: A61F 2013/00638 Gel
• CPC Class Codes: A61F 2013/00646 Medication patches, e.g. transcutaneous
• CPC Class Codes: A61F 2013/00676 hydrogel
• CPC Class Codes: A61F 2013/00689 water-based
• CPC Class Codes: A61F 2013/00719 adhesives for use on wounds
• CPC Class Codes: A61F 2013/00757 with absorbent adhesives
• CPC Class Codes: A61F 2013/00868 thin film
• CPC Class Codes: A61F 2013/00906 for transcutaneous or transdermal drugs application
• CPC Class Codes: A61F 2013/0091 with disinfecting or anaesthetics means, e.g. anti-mycrobic
• CPC Class Codes: A61F 2013/00919 for physical therapy, e.g. cold or magnetic
• CPC Class Codes: A61L 15/58 Adhesives
• CPC Class Codes: A61L 15/585 Mixtures of macromolecular compounds
• CPC Class Codes: A61L 15/60 Liquid-swellable gel-forming materials, e.g. super-absorbents
• CPC Class Codes: A61L 24/043 Mixtures of macromolecular materials
• CPC Class Codes: C08L 39/06 Homopolymers or copolymers of N-vinyl-pyrrolidones
• CPC Class Codes: C08L 79/02 : Polyamines

Abstract

A skin adhesive hydrogel formed by mixing in aqueous medium: (A) major proportion of a high molecular weight water-soluble polyvinylpyrrolidone having ring opened pyrrolidone groups and (B) a minor proportion of a water-soluble multifunctional amine-containing polymer to form a water insoluble, water swellable cross-linked salt between carboxyl groups of the ring opened pyrrolidone groups and basic amine groups of the polyfunctional amine-containing polymer. The reaction is advantageously carried out in the presence of a plasticizer.

Claims

1. A skin adhesive hydrogel composition comprising a water-insoluble, water-swellable cross-linked ampholyte salt of

A. a high molecular weight water-soluble polyvinylpyrrolidone having ring opened pyrrolidone groups providing at least 1.5×

10^-2 milliequivalents of carboxylic acid groups per gram of polymer, and

B. a water-soluble multifinctional amine-containing polymer selected from the group consisting of polyethyleneimine, amine-terminated polyethylene oxide, amine-terminated polyethylene/polypropylene oxide, polymers of dimethyl amino ethyl methacrylate and copolymers of dimethyl amino ethyl methacrylate and vinyl pyrrolidone.

2. The composition of claim 1 wherein the multifunctional amine - containing polymer is selected from the group consisting of polyethyleneimine, amine-terminated polyethylene oxide and amine-terminated polyethylene oxide/polypropylene oxide.

3. The composition of claim 2 wherein the multifunctional amine-containing polymer is polyethyleneimine and the ratio, by weight, of polyvinyl pyrrolidone to polyethyleneimine is from about 15:

1 to about 40;

1.

4. The composition of claim 1 wherein the ring opened polyvinylpyrrolidone has a K-value of at least about 50.

5. The composition of claim 1 comprising also a plasticizer for the hydrogel.

6. The composition of claim 5 wherein the plasticizer is selected from the group consisting of glycerine, ethylene glycol, polypropylene glycol and polyethylene glycol.

7. In a system for attachment to the skin of animals including humans, for cosmetic or medical purposes and including a skin adhesive hydrogel, a plasticizer therefor and a component adapted to impart the desired cosmetic or medical result to or through the skin, the improvement wherein the skin adhesive hydrogel comprises the composition of claim 1.

8. The system of claim 7 in the form of a wound or burn dressing or packing comprising a polymeric film backing controlling the moisture-vapor-transmission rate and wherein the component adopted to impart the desired medical effect is an antimicrobial agent.

9. The system of claim 7 in the form of an electrically conductive electrode adhesive agent wherein the component adapted to provide the desired medical effect is an electrolyte salt.

10. The system of claim 7 in the form of an adhesive agent for attaching a catheter hub or ostomy product to the skin wherein the component adapted to provide the desired medical effect is an antimicrobial agent.

11. The system of claim 9 comprising also an iontophoretic drug.

12. The system of claim 7 in the form of a face mask or nail wrap wherein the component adapted to provide the desired cosmetic effect is a skin moisturizing agent.

13. The system of claim 7 comprising also a transdermal drug.

14. The system of claim 13 comprising also a skin adsorption enhancing agent.

18. The method of claim 14 wherein the ring opened polyvinylpyrrolidone has a K-value of at least about 50.

19. The method of claim 14 wherein the water content of the reaction mixture is from about 40 to about 75%, by weight.

20. The method of claim 14 wherein the reaction is conducted in the presence of a plasticizer.

21. The method of claim 20 wherein the plasticizer is selected from the group consisting of glycerine, ethylene glycol, polypropylene glycol and polyethylene glycol.

22. The method of claim 20 wherein the amount of plasticizer in the reaction mixture is from about 1 to about 30%, by weight, based on the total reaction mixture.

15. The method of making a polymer for skin adhesive hydrogel which comprises mixing in aqueous medium

A. a high molecular weight water-soluble polyvinylpyrrolidone having ring opened pyrrolidone groups providing at least 1.5×

10 milliequivalents of carboxylic acid groups per gram of polymer, and

B. a water-soluble multifunctional amine-containing polymer selected from the group consisting of polyethyleneimine, amine terminated polyethylene oxide, amine terminated polyethylene/polypropylene oxide, polymers of dimethyl amino ethyl methacrylate and copolymers of dimethyl amino ethyl methacrylate and vinyl pyrrolidone until reaction between acid groups of the ring opened polyvinyl-pyrrolidone and basic amine groups of the water-soluble multifunctional amine-containing polymer form a water-insoluble, water-swellable cross-linked ampholyte salt.

16. The method of claim 15 wherein the multifunctional amine-containing polymer is selected from the group consisting of polyethyleneimine, amine-terminated polyethylene oxide and amine-terminated polyethylene oxide/polypropylene oxide.

17. The method of claim 16 wherein the multifunctional amine-containing polymer comprises polyethyleneimine and the ratio, by weight, of polyvinyl pyrrolidone to polyethyleneimine is from about 15:

1 to about 40;

1.