Antimicrobial gels

Patent metadata

Field	Value
Publication number	US-9492549-B2
Application number	US-201113640652-A
Country	US
Kind code	B2
Filing date	Apr 13, 2011
Priority date	Apr 14, 2010
Publication date	Nov 15, 2016
Grant date	Nov 15, 2016

Abstract

The present invention pertains to antimicrobial compositions comprising inter alia at least one alkenyl- and/or alkynyl-substituted polysiloxane, at least one polysiloxane comprising silicon-bonded hydrogen atoms, and at least one hydrosilylation catalyst, as well as antimicrobial silicone gels, wound dressings, and methods of preparing the above.

First claim

The invention claimed is:

1. An antimicrobial composition comprising at least one alkenyl- and/or alkynyl-substituted polysiloxane, at least one polysiloxane comprising silicon-bonded hydrogen atoms, and at least one hydrosilylation catalyst, wherein the composition further comprises at least one silver salt and at least one hydrophilic component, wherein the at least one hydrophilic component promotes release of the at least one silver salt such that the antimicrobial composition has an accumulated silver release of at least 0.3% of the total silver content in the initial antimicrobial composition after 24 hours, and wherein the at least one hydrophilic component makes the antimicrobial composition, when cross-linked, swell at least 5% (wt/wt) after 24 hours in a water solution containing 8.298 g/L of sodium chloride and 0.368 g/L of calcium chloride dihydrate, as measured by the free swell absorption method, wherein the at least one alkenyl- and/or alkynyl-substituted polysiloxane is covalently crosslinked to the at least one polysiloxane comprising silicon-bonded hydrogen atoms, thereby forming an antimicrobial gel.

2. The antimicrobial composition of claim 1 , wherein the at least one hydrophilic component comprises a glucose, xylitol, sorbitol, mannitol, cyclodextrin, cellulose, hemicellulose, carboxymethylated cellulose, chitosan, dextran, chitin, amylose, amylopectin, polyethylene glycol, polypropylene glycol, copolymer of polyethylene glycol and polypropylene glycol, polyglycerol, poly(acrylic acid), copolymer of acrylic acid and C 10 -C 30 alkyl acrylate, poly(acrylamide), maleic anhydride polymer, maleic anhydride copolymer, or carboxy methyl cellulose, methyl cellulose, hydroxymethylpropylcellulose, ethylcellulose, carboxyethylcellulose, hydroxypropylcellulose, hydroxyethylcellulose, carboxymethylcellulose, cellulose alkyl sulfonate, polystyrene sulphonate, vinyl acid, vinyl alcohol, or a mixture thereof.

3. The antimicrobial composition of claim 1 , wherein the concentration of the at least one hydrophilic component is between 3% and 40% (w/w).

4. The antimicrobial composition of claim 1 , wherein the antimicrobial composition further comprises between 1% and 5% (w/w) silica particles.

5. The antimicrobial composition of claim 1 , wherein the silver salt concentration is between 1% and 30% (w/w).

6. The antimicrobial composition of claim 1 , wherein the antimicrobial composition further comprises at least one siloxane-containing copolymer.

7. The antimicrobial composition of claim 6 , wherein the at least one siloxane-containing copolymer comprises at least one siloxane polymer network, at least one siloxane polyether (SPE), or a mixture thereof.

8. The antimicrobial composition of claim 6 , wherein the at least one siloxane-containing copolymer is present at a concentration of between 0.1% and 30% (w/w).

9. The antimicrobial composition of claim 7 , wherein the at least one siloxane-containing copolymer is the at least one siloxane polymer network, wherein the at least one siloxane polymer network comprises a poly-ether-siloxane copolymer network.

10. The antimicrobial composition according to claim 1 , wherein the at least one hydrophilic component comprises a mono-polysaccharide, di-polysaccharide, sugar alcohol, polyol, polyether, polyester, polyamide, polymer comprising a pendant carboxylic acid group, a polymer comprising a pendant sulphonate group, or a mixture thereof.

11. The antimicrobial composition of claim 1 , wherein the at least one silver salt comprises Ag 2 SO 4 , Ag 2 SO 3 ; AgNO 3 , Ag 2 CO 3 , Ag 3 PO 4 , silver zirconium, silver citrate, silver acetate, silver lactate, or a mixture thereof.

12. The antimicrobial composition of claim 1 , wherein the at least one hydrophilic component comprises a sorbitol, mannitol, polyethylene glycol, or carboxy methyl cellulose, or a mixture thereof.

13. An antimicrobial gel produced from a composition comprising at least one alkenyl- and/or alkynyl-substituted polysiloxane, at least one polysiloxane comprising silicon-bonded hydrogen atoms, and at least one hydrosilylation catalyst, wherein the composition further comprises at least one silver salt and at least one hydrophilic component, wherein the at least one hydrophilic component promotes release of the at least one silver salt such that the antimicrobial gel has an accumulated silver release of at least 0.3% of the total silver content in the initial antimicrobial gel after 24 hours, and wherein the at least one hydrophilic component makes the antimicrobial composition, when cross-linked, swell at least 5% (wt/wt) after 24 hours in a water solution containing 8.298 g/L of sodium chloride and 0.368 g/L of calcium chloride dihydrate, as measured by the free swell absorption method, wherein the gel is produced through crosslinking the at least one alkenyl- and/or alkynyl-substituted polysiloxane and the at least one polysiloxane comprising silicon-bonded hydrogen atoms.

14. The antimicrobial gel of claim 13 , wherein the crosslinking of the polysiloxanes is carried out using curing.

15. The antimicrobial gel of claim 13 , wherein the antimicrobial gel further comprises one or more excipients comprising a siloxane-containing copolymer, silica particle, or a mixture thereof.

16. The antimicrobial gel of claim 13 , wherein the corrected zone of inhibition (CZoI) of microbial growth brought about by the antimicrobial gel is at least 2 mm at 24 h.

17. The antimicrobial gel of claim 13 , wherein a circular sample of the antimicrobial gel, assessed using the two-compartment test method, having a diameter of about 20 mm and a coat weight of about 500 g/m 2 , when exposed to 4 ml of bacteria-containing chemical simulated wound fluid at a temperature of 37° C., is able to reduce the number of colony forming units (CFUs) of Staphylococcus aureus from 10 6 to at least 10 5 in 24 h.

18. The antimicrobial gel of claim 13 , wherein the gel has an adhesion with steel of between 0.1 and 2 N as measured by ASTM Internationals' standard D3330/D3330M-04, method F.

19. The antimicrobial gel of claim 13 , wherein the at least one hydrophilic component comprises a glucose, xylitol, sorbitol, mannitol, cyclodextrin, cellulose, hemicellulose, carboxymethylated cellulose, chitosan, dextran, chitin, amylose, amylopectin, polyethylene glycol, polypropylene glycol, copolymer of polyethylene glycol and polypropylene glycol, polyglycerol, poly(acrylic acid), copolymer of acrylic acid and C 10 -C 30 alkyl acrylate, poly(acrylamide), maleic anhydride polymer, maleic anhydride copolymer, or carboxy methyl cellulose, methyl cellulose, hydroxymethylpropylcellulose, ethylcellulose, carboxyethylcellulose, hydroxypropylcellulose, hydroxyethylcellulose, carboxymethylcellulose, cellulose alkyl sulfonate, polystyrene sulphonate, vinyl acid, vinyl alcohol, or a mixture thereof.

20. The antimicrobial gel of claim 13 , wherein the concentration of the at least one hydrophilic component is between 3% and 40% (w/w).

21. The antimicrobial gel of claim 13 , wherein the antimicrobial gel further comprises between 1% and 5% (w/w) silica particles.

22. The antimicrobial gel of claim 13 , wherein the silver salt concentration is between 1% and 30% (w/w).

23. The antimicrobial gel of claim 13 , wherein the antimicrobial gel further comprises at least one siloxane-containing copolymer.

24. The antimicrobial gel of claim 23 , wherein the at least one siloxane-containing copolymer comprises a

Assignees

• Löwenhielm Peter
• Holmén Malin
• Hansson Dennis
• Bergstrand Sofia
• Areskoug Stefan
• Moelnlycke Health Care Ab

Inventors

• Löwenhielm Peter
• Holmén Malin
• Hansson Dennis
• Bergstrand Sofia
• Areskoug Stefan

Classifications

• A61P31/12

  Antivirals · CPC title

• A61P31/02

  Local antiseptics · CPC title

• A61P31/10

  Antimycotics · CPC title

• A61P31/04

  Antibacterial agents · CPC title

• C08J2383/12

  containing polyether sequences · CPC title