Pressure sensitive adhesives having quaternary ammonium functionality, articles, and methods

• US 7,005,031 B2
• Filed: 01/16/2002
• Issued: 02/28/2006
• Est. Priority Date: 01/16/2002
• Status: Expired due to Term

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Lucast, Donald H., Zhu, Dong-Wei
• Primary Examiner(s): YAO, SAMCHUAN CUA
• Application Number:
  US10/052,032
• Publication Number:
  US 20030175503A1
• Time in Patent Office: 1,504 Days
• Field of Search: 156/330.9, 156/331.1, 156/333, 156/327, 523/111, 528/71, 424/78.06, 424/78.07, 424/78.08, 424/78.35, 424/78.37
• US Class Current: 156/330.9
• CPC Class Codes: A61L 15/58 Adhesives
• CPC Class Codes: A61L 15/585 Mixtures of macromolecular compounds
• CPC Class Codes: C08L 33/00 Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 33/02 Homopolymers or copolymers of acids; Metal or ammonium salts thereof
• CPC Class Codes: C08L 71/00 Compositions of polyethers obtained by reactions forming an ether link in the main chain of polyacetals C08L59/00; of epoxy resins C08L63/00; of polythioether-ethers C08L81/02; of polyether-sulfones C08L81/06; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 71/02 Polyalkylene oxides
• CPC Class Codes: C09J 133/02 Homopolymers or copolymers of acids; Metal or ammonium salts thereof
• CPC Class Codes: C09J 2301/302 the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
• CPC Class Codes: Y10T 428/28 Web or sheet containing structurally defined element or component and having an adhesive outermost layer

Abstract

A pressure sensitive adhesive composition is provided that includes a pressure sensitive adhesive polymer. The polymer includes: at least one copolymerized monoethylenically unsaturated (meth)acrylic acid ester monomer, wherein the (meth)acrylic acid ester monomer, when homopolymerized, has a Tg of less than about 25° C.; at least one copolymerized monoethylenically unsaturated reinforcing monomer, wherein the reinforcing monomer, when homopolymerized, has a Tg of at least about 25° C.; covalently bonded quarternary ammonium functionality; and, optionally, at least one copolymerized monoethylenically unsaturated poly(alkylene oxide) monomer. The composition optionally further includes at least one nonreactive poly(alkylene oxide) polymer and/or at least one antimicrobial agent.

Claims

1. A pressure sensitive adhesive composition comprising a pressure sensitive adhesive polymer comprising:

at least one copolymerized monoethylenically unsaturated (meth)acrylic acid ester monomer, wherein the (meth)acrylic acid ester monomer, when homopolymerized, has a Tg of less than about 25°

C.;

at least one copolymerized monoethylenically unsaturated reinforcing monomer, wherein the reinforcing monomer, when homopolymerized, has a Tg of at least about 25°

C.; and

at least one copolymerized poly(alkylene oxide) (meth)acrylic acid ester monomer;

wherein the pressure sensitive adhesive polymer is functionalized with quaternary ammonium functional groups, and further wherein the quaternary ammonium functional groups are covalently bonded to the polymer.

2. The pressure sensitive adhesive composition of claim 1 further comprising at least one nonreactive poly(alkylene oxide) polymer.

3. The pressure sensitive composition of claim 2 wherein the nonreactive poly(alkylene oxide) polymer comprises copolymerized monomers selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide, trimethylene oxide, tetramethylene oxide, their corresponding glycols, and mixtures thereof.

4. The pressure sensitive adhesive composition of claim 1 wherein the pressure sensitive adhesive polymer has a Tg of no greater than about 10°

C.

5. The pressure sensitive adhesive composition of claim 4 wherein the pressure sensitive adhesive polymer has a Tg of no greater than about −

10°

C.

6. The pressure sensitive adhesive composition of claim 5 wherein the pressure sensitive adhesive polymer has a Tg of no greater than about −

20°

C.

7. The pressure sensitive adhesive composition of claim 1 wherein the pressure sensitive adhesive polymer is inherently antimicrobial.

8. The pressure sensitive adhesive composition of claim 1 further comprising at least one antimicrobial agent.

9. The pressure sensitive adhesive composition of claim 8 wherein the antimicrobial agent is present in an amount of at least about 0.05 wt-%, based on the total weight of the pressure sensitive adhesive composition.

10. The pressure sensitive adhesive composition of claim 8 wherein the antimicrobial agent is selected from the group consisting of iodine, complexed forms of iodine, chlorhexidine salts, parachlorometaxylenol, triclosan, hexachlorophene, fatty acid esters, phenols, surfactants having a C12–

C22 hydrophobe and a quaternary ammonium group, quaternary amines, quaternary silanes, hydrogen peroxide, silver, silver salts, silver oxide, silver sulfadiazine, and combinations thereof.

11. The pressure sensitive adhesive composition of claim 10 wherein the antimicrobial agent is a chlorhexidine salt.

12. The pressure sensitive adhesive composition of claim 1 wherein the monoethylenically unsaturated reinforcing monomer is a quaternary ammonium monomer.

13. An article comprising a backing and the pressure sensitive adhesive composition of claim 1 on at least a portion of a surface thereof.

14. The article of claim 13 which adheres to wet skin.

15. The article of claim 14 which has an initial wet skin adhesion of at least about 0.8 N/dm.

16. The article of claim 15 which has an initial wet skin adhesion of at least about 1.6 N/dm.

17. The article of claim 14 which has an initial dry skin adhesion of at least about 0.8 N/dm.

18. The article of claim 14 which has an initial wet skin adhesion that is at least about 65% of the initial dry skin adhesion.

19. The article of claim 13 which is a medical article.

20. A method of using an adhesive article, the method comprising:

providing an adhesive article comprising a backing and the pressure sensitive adhesive composition of claim 1 disposed on at least a portion of a surface thereof; and

adhering the adhesive article to skin.

21. A pressure sensitive adhesive composition comprising a pressure sensitive adhesive polymer comprising:

at least one copolymerized monoethylenically unsaturated (meth)acrylic acid ester monomer, wherein the (meth)acrylic acid ester monomer, when homopolymerized, has a Tg of less than about 25°

C.; and

at least one copolymerized monoethylenically unsaturated reinforcing monomer, wherein the reinforcing monomer, when homopolymerized, has a Tg of at least about 25°

C.;

at least one copolymerized poly(alkylene oxide) (meth)acrylic acid ester monomer;

wherein the pressure sensitive adhesive polymer is functionalized with quaternary ammonium functional groups;

wherein the quaternary ammonium functional groups are covalently bonded to the polymer; and

further wherein the pressure sensitive adhesive composition adheres to wet skin.

22. A method of using an adhesive article, the method comprising:

providing an adhesive article comprising a backing and the pressure sensitive adhesive composition of claim 21 disposed on at least a portion of a surface thereof; and

adhering the adhesive article to skin.

23. An article comprising a backing and the pressure sensitive adhesive composition of claim 21 on at least a portion of a surface thereof.

24. A pressure sensitive adhesive composition comprising a pressure sensitive adhesive polymer comprising:

at least one copolymerized monoethylenically unsaturated (meth)acrylic acid ester monomer, wherein the (meth)acrylic acid ester monomer, when homopolymerized, has a Tg of less than about 25°

C.;

at least one copolymerized quaternary ammonium monomer, wherein the quaternary ammonium monomer, when homopolymerized, has a Tg of at least about 25°

C.; and

at least one copolymerized poly(alkylene oxide) (meth)acrylic acid ester monomer;

wherein the pressure sensitive adhesive polymer is functionalized with quaternary ammonium functional groups, and further wherein the quaternary ammonium functional groups are covalently bonded to the polymer.

25. The pressure sensitive adhesive composition of claim 24 further comprising at least one nonreactive poly(alkylene oxide) polymer.

26. The pressure sensitive adhesive composition of claim 24 wherein the pressure sensitive adhesive is inherently antimicrobial.

27. An article comprising a backing and the pressure sensitive adhesive composition of claim 24 disposed on at least a portion of a surface thereof.

28. A method of using an adhesive article, the method comprising:

providing an adhesive article comprising a backing and the pressure sensitive adhesive composition of claim 24 disposed on at least a portion of a surface thereof; and

adhering the adhesive article to skin.

29. A pressure sensitive adhesive composition comprising:

at least one antimicrobial agent;

at least one nonreactive poly(alkylene oxide) polymer; and

a pressure sensitive adhesive polymer comprising;

at least one copolymerized monoethylenically unsaturated (meth)acrylic acid ester monomer, wherein the (meth)acrylic acid ester monomer, when homopolymerized, has a Tg of less than about 25°

C.;

at least one copolymerized quaternary ammonium monomer, wherein the quaternary ammonium monomer, when homopolymerized, has a Tg of at least about 25°

C.; and

at least one copolymerized poly(alkylene oxide) (meth)acrylic acid ester monomer;

wherein the pressure sensitive adhesive polymer is functionalized with quaternary ammonium functional groups, and further wherein the quaternary ammonium functional groups are covalently bonded to the polymer.

30. An article comprising a backing and the pressure sensitive adhesive composition of claim 29 disposed on at least a portion of a surface thereof.

31. A method of using an adhesive article, the method comprising:

providing an adhesive article comprising a backing and the pressure sensitive adhesive composition of claim 29 disposed on at least a portion of a surface thereof; and

adhering the adhesive article to skin.

32. A pressure sensitive adhesive composition comprising a pressure sensitive adhesive polymer comprising:

at least one copolymerized monoethylenically unsaturated (meth)acrylic acid ester monomer, wherein the (meth)acrylic acid ester monomer, when homopolymerized, has a Tg of less than about 25°

C.;

at least one copolymerized monoethylenically unsaturated reinforcing monomer, wherein the reinforcing monomer, when homopolymerized, has a Tg of at least about 25°

C.; and

at least one copolymerized poly(alkylene oxide) (meth)acrylic acid ester monomer;

wherein the pressure sensitive adhesive polymer is functionalized with quaternary ammonium functional groups, and further wherein the quaternary ammonium functional groups are covalently bonded to the polymer; and

further wherein the pressure sensitive adhesive polymer includes no more than about 5 weight percent of copolymerized acidic monomers, based on the total weight of pressure sensitive adhesive polymer.

33. An article comprising a backing and the pressure sensitive adhesive composition of claim 32 disposed on at least a portion of a surface thereof.

34. A method of using an adhesive article, the method comprising:

providing an adhesive article comprising a backing and the pressure sensitive adhesive composition of claim 32 disposed on at least a portion of a surface thereof; and

adhering the adhesive article to skin.

35. A pressure sensitive adhesive composition comprising:

at least one antimicrobial agent; and

a pressure sensitive adhesive polymer comprising;

at least one copolymerized monoethylenically unsaturated (meth)acrylic acid ester monomer, wherein the (meth)acrylic acid ester monomer, when homopolymerized, has a Tg of less than about 25°

C.;

at least one copolymerized quaternary ammonium monomer, wherein the quaternary ammonium monomer, when homopolymerized, has a Tg of at least about 25°

C.; and

at least one copolymerized poly(alkylene oxide) (meth)acrylic acid ester monomer;

wherein the pressure sensitive adhesive polymer is functionalized with quaternary ammonium functional groups, and further wherein the quaternary ammonium functional groups are covalently bonded to the polymer.

36. An article comprising a backing and the pressure sensitive adhesive composition of claim 35 disposed on at least a portion of a surface thereof.

37. A method of using an adhesive article, the method comprising:

providing an adhesive article comprising a backing and the pressure sensitive adhesive composition of claim 35 disposed on at least a portion of a surface thereof, and

adhering the adhesive article to skin.

38. A method of making a pressure sensitive adhesive composition, the method comprising combining under conditions effective to cause polymerization:

at least one monoethylenically unsaturated (meth)acrylic acid ester monomer, which when homopolymerized, has a Tg of less than about 25°

C.;

at least one quaternary ammonium monomer, wherein the quaternary ammonium monomer, when homopolymerized, has a Tg of at least about 25°

C.; and

at least one poly(alkylene oxide) (meth)acrylic acid ester monomer;

wherein the pressure sensitive adhesive polymer is functionalized with quaternary ammonium functional groups, and further wherein the quaternary ammonium functional groups are covalently bonded to the polymer.

39. The method of claim 38 wherein the monomers are copolymerized prior to the addition of at least one nonreactive poly(alkylene oxide) polymer.

40. The method of claim 38 wherein the monomers are copolymerized prior to the addition of at least one antimicrobial agent.