Silicone gel adhesive with hydrophillic and antimicrobial properties

Patent metadata

Field	Value
Publication number	US-10370571-B2
Application number	US-201314648633-A
Country	US
Kind code	B2
Filing date	Mar 13, 2013
Priority date	Dec 7, 2012
Publication date	Aug 6, 2019
Grant date	Aug 6, 2019

Abstract

Adhesive compositions are provided that include a crosslinked silicone gel, a hydrophilic component dispersed in the silicone gel, and an antimicrobial agent dispersed in the silicone gel. The adhesive composition is readily applied to (and removed from) skin, and has desirable hydrophilic and antimicrobial properties. Advantageously, the hydrophilic component in the crosslinked silicone gel is not readily extractable (e.g., into a pH 7 buffer). Surprisingly, the combination of hydrophilic component with antimicrobial agent in the crosslinked silicone gel can provide a synergistic level of antimicrobial activity.

First claim

What is claimed is:

1. An adhesive composition comprising:
a) 35 to 95 weight percent of a silicone gel based on a total weight of the adhesive composition, the silicone gel comprising a crosslinked poly(diorganosiloxane) having terminal groups of formula O—Si(R 1 )(R 2 ) 2 wherein R 1 is hydroxyl, alkyl, or aryl and each R 2 is independently alkyl or aryl;
b) 5 to 50 weight percent of a hydrophilic component based on the total weight of the adhesive composition, the hydrophilic component being dispersed in the silicone gel, wherein the hydrophilic component comprises a carbohydrate having at least 3 hydroxyl groups, a carbohydrate derivative having at least 3 hydroxyl groups, or a combination thereof and wherein the hydrophilic component is covalently crosslinked to the poly(diorganosiloxane) by electron beam or gamma ray radiation; and
c) 0.1 to 20 weight percent of an antimicrobial agent based on the total weight of the adhesive composition, the antimicrobial agent being dispersed in the silicone gel, wherein the antimicrobial agent comprises elemental copper, elemental silver, a silver-containing compound, or a combination thereof;

wherein less than 10 weight percent of the hydrophilic component is extractable from the adhesive composition into a phosphate buffer saline solution at pH 7 within 24 hours at room temperature and wherein the adhesive composition is a pressure sensitive adhesive.

2. The adhesive composition of claim 1 , wherein the silicone gel is crosslinked in the absence of a peroxide, condensation catalyst, or hydrosilation catalyst.

3. The adhesive composition of claim 1 , wherein the silicone gel is substantially free of —SiH groups.

4. The adhesive composition of claim 1 , wherein the silicone gel is crosslinked using an electron beam.

5. The adhesive composition of claim 1 , wherein the hydrophilic component is a cellulosic material, and wherein the cellulosic material is optionally methoxylated or ethoxylated.

6. The adhesive composition of claim 1 , wherein the hydrophilic component is a monosaccharide, reduced monosaccharide, disaccharide, reduced disaccharide, polysaccharide, reduced polysaccharide, methoxylated or ethoxylated derivatives thereof, or combination thereof.

7. The adhesive composition of claim 1 , wherein the antimicrobial agent comprises a copper salt, silver salt, or a combination thereof.

8. The adhesive composition of claim 1 , wherein the adhesive composition comprises 40 to 80 weight percent silicone gel, 10 to 40 weight percent hydrophilic component, 0.5 to 10 weight percent antimicrobial agent, and 5 to 49.5 weight percent tackifier, wherein each amount is based on a total weight of the adhesive composition.

9. The adhesive composition of claim 1 , further comprising a tackifier.

10. The adhesive composition of claim 9 , wherein the tackifier is a silicate resin.

11. The adhesive composition of claim 1 , wherein the adhesive composition further comprises 0.1 to 59.9 weight percent of a tackifier, based on a total weight of the adhesive composition.

12. The adhesive composition of claim 1 , wherein the poly(diorganosiloxane) comprises a poly(dimethylsiloxane) having —Si(OH)(CH 3 ) 2 or —Si(CH 3 ) 3 terminal groups.

13. The adhesive composition of claim 1 , wherein the poly(diorganosiloxane) is of formula 2:

wherein each R 1 is independently hydroxyl, alkyl, or aryl, and wherein each R 2 , R 3 , R 4 , R 5 , and R 6 is independently alkyl or aryl, and m and n are integers, and at least one of m or n is not zero.

14. An article comprising a substrate and a layer of the adhesive composition of claim 1 adhered to the substrate.

15. The article of claim 14 , wherein the layer of the adhesive composition has a thickness of 20 micrometers to 200 micrometers.

16. The article of claim 14 , wherein the substrate comprises at least one of paper, polymeric film, and woven cloth and non-woven cloth.

17. The adhesive composition of claim 1 , wherein the adhesive composition is positioned adjacent to human or animal skin.

18. The adhesive composition of claim 17 , wherein the adhesive composition is positioned over a wound site.

19. The article of claim 14 , wherein the article is a medical dressing.

20. The adhesive composition of claim 1 , wherein the adhesive composition comprises 45 to 60 weight percent silicone gel, 20 to 35 weight percent hydrophilic component, 1 to 5 weight percent antimicrobial agent, and 10 to 34 weight percent tackifier, wherein each amount is based on a total weight of the adhesive composition.

Assignees

• 3M Innovative Properties Co

Inventors

• Determan Michael D
• Tse Kiu-Yuen
• Chatterjee Joon

Classifications

• C09J183/04 Primary

  Polysiloxanes · CPC title

• C08L9/02

  Copolymers with acrylonitrile · CPC title

• A61L2300/404

  Biocides, antimicrobial agents, antiseptic agents · CPC title

• A61L2300/104

  Silver, e.g. silver sulfadiazine · CPC title

• A61L2300/102

  Metals or metal compounds, e.g. salts such as bicarbonates, carbonates, oxides, zeolites, silicates · CPC title