Adhesive compositions, articles incorporating same and methods of manufacture

• US 20040247655A1
• Filed: 06/05/2003
• Published: 12/09/2004
• Est. Priority Date: 06/05/2003
• Status: Active Grant

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Etzold, Beatrice C., Asmus, Robert A., Packard, Joy A.
• Granted Patent: US 9,278,155 B2
• Time in Patent Office: Days
• US Class Current: 424/449
• CPC Class Codes: A61L 15/58 Adhesives
• CPC Class Codes: C08K 5/053 Polyhydroxylic alcohols
• CPC Class Codes: C08L 1/00 Compositions of cellulose, modified cellulose or cellulose derivatives
• CPC Class Codes: C08L 2666/26 Natural polymers, natural resins or derivatives thereof according to C08L1/00 - C08L5/00, C08L89/00, C08L93/00, C08L97/00 or C08L99/00
• CPC Class Codes: C08L 39/04 Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
• CPC Class Codes: C08L 5/00 Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
• CPC Class Codes: C09J 133/24 Homopolymers or copolymers of amides or imides

Abstract

A hydrophilic, pressure-sensitive adhesive composition comprising crosslinked poly(N-vinyl lactam), a swelling agent, and a modifying polymer in an amount sufficient to form a cohesive pressure-sensitive adhesive composition is provided. The composition is useful as a medical secural of percutaneous devices. The composition is also useful as a drug delivery device to deliver antimicrobial agents, pharmaceuticals or other active ingredients to or through skin. A method of preparation of the composition is also disclosed.

Claims

1. An adhesive composition comprising:

a first polymer comprising a cross-linked poly (N-vinyl lactam);

a swelling agent; and

a second modifying polymer swellable in the swelling agent;

the first polymer forms a pressure sensitive adhesive in the presence of the swelling agent; and

the second modifying polymer and the swelling agent reduce the adhesiveness of the first polymer while at least maintaining the cohesion of the composition.

2. The composition of claim 1 further comprising an antimicrobial agent.

3. The composition of claim 2 wherein the antimicrobial agent is chlorhexidine gluconate.

4. The composition of claim 2 wherein the antimicrobial agent is selected from the group consisting of parachlorometaxylenol;

triclosan;

chlorhexidine and salts thereof;

poly hexamethylene biguanide and salts thereof;

iodine;

idodophors;

silver oxide;

silver and its salts;

peroxides;

antibiotics; and

combinations of the foregoing.

5. The composition of claim 1 wherein the poly (N-vinyl lactam) is selected from the group consisting of poly N-vinyl-2-pyrrolidone, poly N-vinyl-2-valerolactam, poly N-vinyl-2-caprolactam, and combinations of the foregoing.

6. The composition of claim 1 wherein the swelling agent is selected from the group consisting of monohydric alcohols;

polyhydric alcohols;

glycerol;

polyglycerols;

sorbitol;

polyhydric alcohol ethoxylates;

methoxides of polyethylene glycol;

methoxides of polyhydric alcohol ethoxylates; and

combinations of the foregoing.

7. The composition of claim 6 wherein the monohydric alcohols consist of ethanol, isopropanol, n-propanol, and combinations of the foregoing.

8. The composition of claim 6 wherein the polyhydric alcohols consist of propylene glycol, dipropylene glycol, polyethylene glycol, and combinations of the foregoing.

9. The composition of claim 8 wherein the polyethylene glycol is of a molecular weight between 200 and 600.

10. The composition of claim 6 wherein the polyglycerols consist of diglycerin, triglycerol, polyglycerin-3, hexaglycerol, decaglycerol and combinations of the foregoing.

11. The composition of claim 6 wherein the polyhydric alcohol ethoxylates consist of sorbeth-6, sorbeth-30, glycereth-1to glycereth-31.

12. The composition of claim 6 wherein the methoxides of polyethylene glycol consist of methoxy polyethylene glycol-2 to methoxy polyethylene glycol-00.

13. The composition of claim 6 wherein the methoxides of polyhydric alcohol ethoxylates is glycereth-7 methoxide.

14. The adhesive composition of claim 1, wherein the swelling agent is greater than 50% of the total weight of the composition.

15. The adhesive composition of claim 1 wherein the second modifying polymer comprises a polysaccharide, polysaccharide derivatives, acrylate, acrylate derivatives, cellulose, cellulose derivatives, and combinations thereof.

16. The composition of claim 15 wherein the second modifying polymer is selected from the group consisting of hydroxypropyl guar;

guar gum;

hydroxyethyl cellulose;

hydroxypropyl cellulose;

hydroxypropyl methylcellulose;

polymeric quaternary ammonium salt of hydroxyethyl cellulose reacted with trialkyl ammonium substituted epoxide;

copolymers of hydroxyethyl cellulose and diallyldimethyl ammonium chloride; and

derivatives and combinations of the foregoing.

17. The composition of claim 16 wherein the hydroxyethyl cellulose is hydrophobically modified.

18. The composition of claim 16 wherein the hydroxyethyl cellulose is reacted with trialkyl ammonium substituted epoxide.

19. The composition of claim 18 wherein the trialkyl ammonium substituted epoxide is selected from the group consisting of trimethyl ammonium substituted epoxide;

lauryl dimethyl ammonium substituted epoxide; and

derivatives and combinations of the foregoing.

20. The composition of claim 1 wherein:

the first polymer is present in the composition in an amount between 5% and 50% by weight;

the swelling agent is present in an amount of at least 55% by weight; and

the second polymer is present in an amount between 0.1% and 40% by weight.

21. The composition of claim 20 further comprising an antimicrobial agent in an amount up to 10% by weight.

22. The composition of claim 21 wherein first polymer is poly N-vinyl-2-pyrrolidone;

the swelling agent is triglycerol;

the second polymer is selected from the group consisting of hydroxypropyl guar;

guar gum;

hydroxyethyl cellulose;

hydroxypropyl cellulose;

hydroxypropyl methylcellulose;

polymeric quaternary ammonium salt of hydroxyethyl cellulose reacted with trialkyl ammonium substituted epoxide;

copolymers of hydroxyethyl cellulose and diallyldimethyl ammonium chloride; and

derivatives and combinations of the foregoing; and

the antimicrobial agent is chlorhexidine gluconate.

23. The composition of claim 1 configured as a medical sealant for sealing a junction between living skin and a medical instrument penetrating through the skin.

24. The composition of claim 23 wherein the medical sealant comprises first and second major surfaces, each major surface associated with a release liner.

25. The composition of claim 24 wherein a first release liner is associated with the first major surface and having a first release value, a second release liner is associated with the second major surface and having a second release value different from the first release value.

26. The composition of claim 25, wherein the adhesive composition is configured in a substantially heart-shaped outline.

27. A method for the manufacture of the adhesive composition of claim 1, the method comprising

(a) irradiating with gamma radiation the precursor of the first polymer to cross-link the precursor;

(b) mixing the crosslinked first polymer with the swelling agent and the second modifying polymer to provide the composition of claim 1.

28. A medical article comprising a backing layer and the adhesive composition of claim 1.

29. The medical article according to claim 28, wherein the article comprises a medical tape, a wound dressing, a bandage or a medical skin covering.

30. A pharmaceutical delivery device comprising:

an adhesive layer for contacting skin and a backing layer, the adhesive layer adhered to the backing layer and comprising the adhesive composition of claim 1.

31. The delivery device according to claim 30, wherein the adhesive layer further comprises a topical, transdermal, or iontophoretic therapeutic agent.

32. The delivery device according to claim 30, wherein the adhesive layer further comprises an excipient, a solvent, or a penetration enhancing agent.

33. The composition according to claim 1, wherein the poly(N-vinyl lactam) is poly(N-vinyl pyrrolidone) and the amount of the swelling agent ranges from about 60 to about 80 weight percent of the composition.

34. The composition according to claim 33, wherein the poly(N-vinyl lactam) is poly(N-vinyl-2-pyrrolidone) homopolymer.

35. The composition according to claim 33, wherein the poly(N-vinyl lactam) is a copolymer of N-vinyl-2-pyrrolidone monomer and a non-N-vinyl lactam comonomer selected from the group consisting of N,N-dimethylacrylamide, acrylic acid, methacrylic acid, hydroxyethylmethacrylate, acrylamide, vinyl acetate, and 2-acrylamido-2-methyl-1-propane sulfonic acid or its salt;

the copolymer comprising N-vinyl-2-pyrrolidone monomeric units in an amount no less than about 50 weight percent of the poly(N-vinyl lactam).

36. The composition according to claim 33, wherein the copolymer comprises N-vinyl-2-pyrrolidone monomeric units in an amount from about 70 to about 100 weight percent of the poly(N-vinyl lactam).

37. The composition according to claim 1, wherein the radiation-crosslinked poly(N-vinyl lactam) has a Swelling Capacity of at least 15 milliliters of water per gram of the radiation-crosslinked poly(N-vinyl lactam).

38. The composition according to claim 1, wherein the cross-linked poly(N-vinyl lactam) is radiation-crosslinked while in solid form.

39. The composition according to claim 1, wherein the modifying polymer and the swelling agent are present in the composition in unirradiated form.

40. The composition of claim 1, wherein the second modifying polymer and the swelling agent reduce the adhesiveness of the first polymer while increasing the cohesion of the composition.