Antimicrobial-containing silicone lubricious coatings

Patent metadata

Field	Value
Publication number	US-11464889-B2
Application number	US-201916697223-A
Country	US
Kind code	B2
Filing date	Nov 27, 2019
Priority date	Nov 29, 2018
Publication date	Oct 11, 2022
Grant date	Oct 11, 2022

Abstract

Novel, lubricious antimicrobial coatings for medical devices are disclosed. The coatings provide improved lubricity and durability and are readily applied in coating processes at low temperatures that do not deform the device and preserves the antimicrobial effectiveness of the antimicrobial agent. The present invention is also directed to a novel platinum catalyst for use in such coatings. The catalyst provides for rapid curing, while inhibiting cross-linking at ambient temperatures, thereby improving the production pot life of the coatings.

First claim

We claim:

1. A medical device coated with a lubricious silicone coating, comprising:
a medical device having a surface; and,
a lubricious silicone coating on at least a part of the surface, the coating formed from a coating composition comprising:
a cross-linkable silicone polymer having reactive functionalities;
optionally, a silica-containing composition;
a silicone cross-linking agent;
an antimicrobial agent selected from the group consisting of triclosan, chlorhexidine, polyhexamethylene biguanide (PHMB), octenidine, and silver; and,
a catalyst, wherein said catalyst consists essentially of platinum divinyltetramethyldisiloxane vinylcyclohexanol complex having the formula:
Pt[(CH 2 ═CH)(CH 3 ) 2 Si] 2 O·C 6 H 10 (OH)(C═CH).

2. The medical device of claim 1 , wherein the cross-linkable silicone polymer is selected from the group consisting of vinyl terminated polydialkylsiloxane, vinyl terminated polydimethylsiloxane, vinyl terminated polydiphenylsilane-dimethylsiloxane copolymer, vinyl terminated polyphenylmethylsiloxane, vinyl terminated polyfluoropropylmethyl-dimethylsiloxane copolymer and vinyl terminated polydiethylsiloxane.

3. The medical device of claim 1 , wherein the cross-linkable silicone polymer comprises vinyl terminated polydimethylsiloxane.

4. The medical device of claim 1 , wherein the antimicrobial agent is triclosan.

5. The medical device of claim 1 , wherein the silicone cross-linking agent is selected from the group consisting of polymethylhydrosiloxane, polymethylhydro-co-polydimethylsiloxane, polyethylhydrosiloxane, polymethylhydrosiloxane-co-octylmethylsiloxane, and polymethylhydrosiloxane-co-methylphenylsiloxane.

6. The medical device of claim 1 , wherein the silicone cross-linking agent comprises polymethylhydrosiloxane.

7. The medical device of claim 1 , wherein the silica-containing composition comprises a trimethyl silyl surface treated silica filler.

8. The medical device of claim 1 , wherein the silica-containing composition is selected from the commercially available reactive silica-containing silicone bases including HCR (high consistent rubber) bases and LSR (liquid silicone rubber) bases.

9. The medical device of claim 8 , wherein the silica-containing composition is a liquid silicone rubber base.

10. The medical device of claim 1 , wherein the coating composition additionally comprises about 20 wt. % to about 99.5 wt. % of an organic solvent, based upon the weight of the coating composition.

11. The medical device of claim 1 , wherein the coating solution comprises about 1 to 40 wt. % (total solids) of triclosan antimicrobial agent.

12. The medical device of claim 1 , wherein the coating composition comprises about 0.2 wt. % to about 1.8 wt. % of the silicone cross-linking agent based on total solids, wherein the coating composition additionally comprises about 75 wt. % to about 99.5 wt. % of an organic solvent, based upon the weight of the coating composition.

13. The medical device of claim 1 , wherein the coating composition comprises about 0.0004 wt. % to about 0.0036 wt. % of the platinum catalyst, based on total solids, wherein the coating composition additionally comprises about 75 wt. % to about 99.5 wt. % of an organic solvent, based upon the weight of the coating composition.

14. The medical device of claim 1 , wherein the coating composition additionally comprises a solvent selected from the group consisting of xylene, toluene, pentane, hexane, heptanes, octane, mixtures of higher molecular weight olefins, and combinations thereof.

15. The medical device of claim 1 , wherein the medical device comprises a biocompatible material selected from the group consisting of stainless steels, PTFE, glasses, ceramics, polymers, refractory metal alloys, memory alloys, and composites of metals and non-metals.

16. The medical device of claim 1 , wherein the medical device is selected from the group consisting of surgical needles, sutures, hypodermic needles, surgical scalpels, catheters, cutting blades, surgical probes, endoscopes, scissors, and cutting blades.

17. The medical device of claim 16 , wherein the medical device comprises a surgical suture.

18. The medical device of claim 1 , wherein the coating further comprises a non-cross-linkable siloxane.

19. The medical device of claim 18 , wherein the non-cross-linkable siloxane is trimethylsilyl-terminated polydimethylsiloxane.

20. A coating composition comprising:
a cross-linkable silicone polymer having reactive functionalities;
optionally a silica-containing composition;
optionally a non-cross-linkable siloxane;
a silicone cross-linking agent;
an antimicrobial agent selected from the group consisting of triclosan, chlorhexidine, polyhexamethylene biguanide (PHMB), octenidine, and silver; and
a catalyst, wherein said catalyst consists essentially of platinum divinyltetramethyldisiloxane vinylcyclohexanol complex having the formula:
Pt[(CH 2 ═CH)(CH 3 ) 2 Si] 2 O·C 6 H 10 (OH)(C═CH).

21. The coating composition of claim 20 , wherein the composition is curable at temperatures above about 70 C.

22. The coating composition of claim 21 , wherein the composition is curable at temperatures of about 95 C in about 2 minutes.

Assignees

• Ethicon Inc

Inventors

• Ou Duan Li
• Cichocki Jr Frank R

Classifications

• C09D5/14

  Paints containing biocides, e.g. fungicides, insecticides or pesticides (C09D5/16 takes precedence) · CPC title

• C10M2229/0445

  used as base material · CPC title

• A61L2420/02

  Methods for coating medical devices · CPC title

• A61L2300/404

  Biocides, antimicrobial agents, antiseptic agents · CPC title

• C10M107/50

  containing silicon · CPC title