Polymer compositions with bioactive agent, medical articles, and methods

• US 8,193,267 B2
• Filed: 05/19/2010
• Issued: 06/05/2012
• Est. Priority Date: 12/05/2003
• Status: Active Grant

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Burton, Scott A., Hyde, Patrick D., Rao, Prabhakara S., Ylitalo, Caroline M.
• Primary Examiner(s): Nerangis, Vickey
• Application Number:
  US12/782,863
• Publication Number:
  US 20100233273A1
• Time in Patent Office: 748 Days
• Field of Search: 524/403, 524/413, 524/432, 523/122
• US Class Current: 524/403
• CPC Class Codes: A61L 15/18 containing inorganic materials
• CPC Class Codes: A61L 15/22 containing macromolecular materials
• CPC Class Codes: A61L 15/46 Deodorants or malodour counteractants, e.g. to inhibit the formation of ammonia or bacteria
• CPC Class Codes: A61L 2300/102 Metals or metal compounds, e.g. salts such as bicarbonates, carbonates, oxides, zeolites, silicates
• CPC Class Codes: A61L 2300/104 Silver, e.g. silver sulfadiazine
• CPC Class Codes: A61L 2300/622 Microcapsules
• CPC Class Codes: A61P 17/02 for treating wounds, ulcers, burns, scars, keloids, or the like
• CPC Class Codes: A61P 31/00 Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics

Abstract

A polymer composition that includes a hydrophilic polymer, an optional secondary organic polymer, and a bioactive agent distributed therein, wherein the bioactive agent is selected from the group consisting of a silver compound, a copper compound, a zinc compound, and combinations thereof.

Claims

1. A method of making a polymer composition, wherein the method comprises:

combining a dispersion comprising hydrophilic organic microparticles with water and a metal compound under conditions effective to distribute substantially all of the metal compound within the hydrophilic organic microparticles, wherein the metal compound is selected from the group consisting of a silver compound, a copper compound, a zinc compound, and combinations thereof;

wherein the silver compound has a solubility in water of at least 0.1 gram per liter in water;

adding a hydroxide source to convert the metal compound to the corresponding metal oxide within the hydrophilic organic microparticles;

wherein the resulting metal oxide is in the form of particles having an average particle size of less than 1 micron;

optionally adding a secondary organic polymer to the dispersion; and

optionally removing a substantial portion of the water.

2. The method of claim 1 wherein the dispersion comprising the microparticles is combined with water in an amount of 1 to 20 wt % based on the total weight of the polymer composition.

3. The method of claim 1 further comprising the step of adding an oxidizing agent to form a higher valence metal oxide.

4. The method of claim 1 further comprising extruding or molding the composition.

5. The method of claim 1 wherein the dispersion comprising hydrophilic organic microparticles further comprises a hydrophobic liquid.

6. The method of claim 5 where in the hydrophobic liquid is mineral oil.

7. A method of making a polymer composition, wherein the method comprises:

combining monomers for a hydrophilic organic polymer with a metal compound under conditions effective to polymerize the monomers and distribute substantially all of the metal compound within the hydrophilic organic polymer, wherein the metal compound is selected from the group consisting of a silver compound, a copper compound, a zinc compound, and combinations thereof;

wherein the silver compound has a solubility in water of at least 0.1 gram per liter in water;

adding a hydroxide source to convert the bioactive agent to the corresponding metal oxide within the hydrophilic organic polymer;

wherein the resulting metal oxide is in the form of particles having an average particle size of less than 1 micron; and

optionally adding a secondary organic polymer to the hydrophilic organic polymer wherein the monomers for a hydrophilic organic polymer are dispersed in a hydrophobic liquid.

8. The method of claim 7 where in the hydrophobic liquid is mineral oil.

9. The method of claim 7 further comprising subjecting the monomers to radiation.

10. A method of forming silver oxide in a hydrocolloid, the method comprising:

providing a mixture of a hydrocolloid and a solution of a silver compound with a solubility of at least 0.1 gram per liter in water;

wherein the hydrocolloid comprises hydrophilic particles;

adding a hydroxide source under conditions sufficient to convert the silver compound to a metal oxide of silver (I) and disperse the silver oxide within the hydrophilic particles of the hydrocolloid;

wherein the resulting silver oxide is in the form of particles having an average particle size of less than 1 micron.

11. The method of claim 10 wherein water is present in the solution in an amount of 1 to 20 wt % based on the total weight of the hydrocolloid.

12. The method of claim 10 wherein the hydrocolloid comprises hydrophilic particles dispersed in a hydrophobic liquid.

13. The method of claim 12 where in the hydrophobic liquid is mineral oil.

14. The method of claim 10 further comprising the step of adding an oxidizing agent to form a higher valence oxide of silver.

15. The method of claim 10 wherein the hydrophilic particles of the hydrocolloid have a particle size less than 10 microns.

16. The method of claim 10 further comprising the step of adding a hydrophobic polymer.

17. The method of claim 16 wherein the hydrophobic polymer comprises styrene-isoprene-styrene.

18. A method of making a polymer composition comprising:

combining;

a hydrophilic organic polymer dispersed within a hydrophobic liquid;

a metal compound selected from the group consisting of a silver compound, a copper compound, a zinc compound, and combinations thereof, wherein the silver compound has a solubility in water of at least 0.1 gram per liter in water; and

a hydroxide source that converts the metal compound to the corresponding metal oxide; and

dispersing the metal oxide within the hydrophilic organic polymer, which is dispersed within a hydrophobic liquid;

wherein the resulting dispersed metal oxide is in the form of particles having an average particle size of less than 1 micron.

19. A method of making a polymer composition comprising:

combining;

a hydrophilic organic polymer dispersed within a hydrophobic liquid;

a metal compound selected from the group consisting of a silver compound, a copper compound, a zinc compound, and combinations thereof, wherein the silver compound has a solubility in water of at least 0.1 gram per liter in water;

water in an amount of 1 to 20 wt % based on the total weight of the polymer composition; and

a hydroxide source that converts the metal compound to the corresponding metal oxide; and

providing conditions effective to convert the metal compound to the corresponding metal oxide and disperse the metal oxide within the hydrophilic organic polymer, which is dispersed within a hydrophobic liquid;

wherein the resulting dispersed metal oxide is in the form of particles having an average particle size of less than 1 micron.

20. The method of claim 19 where in the hydrophobic liquid is mineral oil.

21. The method of claim 19 wherein the hydrophilic polymer is selected from the group consisting of polyhydroxyalkyl acrylates and methacrylates;

poly(meth)acrylic acid and salts thereof;

polyvinyl alcohols;

polyoxyalkylenes;

polystyrene sulfonates;

polysaccharides;

alginates;

gums;

cellulosics;

polymers prepared from water-soluble hydrazine derivatives;

polyurethanes, mono-olefinic sulfonic acids and their salts; and

combinations thereof.

22. The method of claim 19 wherein the hydrophilic polymer is an amine-containing organic polymer selected from the group consisting of poly(quaternary amines), polylactams, polyamides, and combinations thereof.

23. The method of claim 22 wherein the amine-containing organic polymer is a quaternary ammonium salt of an organic polymer.

24. The method of claim 19 wherein the hydrophilic polymer comprises absorbent hydrophilic microparticles, wherein the microparticles comprise a carboxylic-acid containing organic polymer.

25. The method of claim 19 wherein the hydroxide source is added after combining the bioactive agent and the hydrophilic polymer.

26. The method of claim 19 further comprising combining an oxidizing agent with the hydrophilic polymer, the metal compound, and the hydroxide source.

27. The method of claim 26 wherein the oxidizing agent is added after combining the hydrophilic polymer, the metal compound, and the hydroxide source.