PROCESS FOR PRODUCING AN ANTIMICROBIAL COATING

• US 20080152685A1
• Filed: 12/11/2007
• Published: 06/26/2008
• Est. Priority Date: 12/20/2006
• Status: Abandoned Application

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: Ingham, Scott J., Salamone, Joseph C., Blackwell, Richard I., Scheuer, Catherine
• Application Number:
  US11/954,073
• Publication Number:
  US 20080152685A1
• Time in Patent Office: Days
• US Class Current: 424/412
• CPC Class Codes: C08J 2439/00 Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Derivatives of such polymers
• CPC Class Codes: C08J 2479/00 Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2461/00 - C08J2477/00
• CPC Class Codes: C08J 7/0427 with only one layer of a composition containing a polymer binder with more layers C08J7/042
• CPC Class Codes: C08J 7/123 Treatment by wave energy or particle radiation C08J7/18 takes precedence

Abstract

A process for covalently attaching an antimicrobial coating to a polymeric surface. The process comprises contacting the surface of the polymer with a plasma having reactive nitrogen compounds to provide a plasma-treated surface with —NHR groups, wherein R is hydrogen, hydroxyl or C_1-2alkyl, reacting the —NHR groups with a surface linking agent, and attaching an amine-containing polymer to the linking agent to form the antimicrobial coating. The surface linking agent is selected from the group consisting of dihaloalkyl, a dihaloalkenyl, and a dihalomethylaryl. The invention is also directed to a contact lens case or a contact lens with an antimicrobial coating.

Claims

1. A process for covalently attaching an antimicrobial coating to a polymeric surface, the process comprising:

contacting the surface of the polymer with a plasma having reactive nitrogen compounds to provide a plasma-treated surface with —

NHR groups, wherein R is hydrogen, hydroxyl or C_1-2alkyl;

reacting the —

NHR groups with a surface linking agent selected from the group consisting of dihaloalkyl, a dihaloalkenyl, and a dihalomethylaryl, and

attaching an amine-containing polymer to the linking agent to form the antimicrobial coating.

2. The process of claim 1 wherein the plasma is generated in the presence of ammonia.

3. The process of claim 1 wherein the surface linking agent is a dihaloalkyl.

4. The process of claim 1 wherein the surface linking agent is an α

,ω

-dihaloalkane or an α

,ω

-dihalo-2-alkene.

5. The process of claim 4 wherein the α

,ω

-dihaloalkane is 1,4-dibromobutane and the α

,ω

-dihalo-2-alkene is 1,4-bromo-2-butene.

6. The process of claim 1 wherein the surface linking agent is a dihalomethylaryl compound.

7. The process of claim 6 wherein the dihalomethylaryl compound is 1,4-bis(dichloromethyl)benzene.

8. The process of claim 1 wherein the antimicrobial, amine-containing polymer comprises an amine selected from the group consisting of a tertiary amine group and a pyridine group.

9. The process of claim 1 wherein the antimicrobial, amine-containing polymer comprises poly(4-vinylpyridine).

10. The process of claim 1 wherein the polymer surface is the surface of a contact lens case.

11. The process of claim 1 wherein the polymer surface is the surface of a contact lens.

12. A process of attaching an antimicrobial coating to an interior surface of a contact lens case, the process comprising:

providing a contact lens case with an exposed interior surface;

contacting the interior surface of the lens case with a plasma having reactive nitrogen compounds to provide a plasma-treated surface with —

NHR groups, wherein R is hydrogen, hydroxyl or C_1-2alkyl;

reacting the —

NHR groups with a surface linking agent selected from the group consisting of dihaloalkyl, a dihaloalkenyl, and a dihalomethylaryl, and

attaching an amine-containing polymer to the linking agent to form the antimicrobial coating on the interior surface of the lens case.

13. The process of claim 12 wherein the antimicrobial, amine-containing polymer comprises an amine selected from the group consisting of a tertiary amine group and a pyridine group.

14. The process of claim 12 wherein the antimicrobial, amine-containing polymer comprises poly(4-vinylpyridine).

15. A contact lens case comprising an antimicrobial coating wherein the antimicrobial coating is prepared by a process comprising:

providing a contact lens case with an exposed interior surface;

contacting the interior surface of the lens case with a plasma having reactive nitrogen compounds to provide a plasma-treated surface with —

NHR groups, wherein R is hydrogen, hydroxyl or C_1-2alkyl;

reacting the —

NHR groups with a surface linking agent selected from the group consisting of dihaloalkyl, a dihaloalkenyl, and a dihalomethylaryl, and

attaching an amine-containing polymer to the linking agent to form the antimicrobial coating on the interior surface of the lens case.

16. The process of claim 15 wherein the antimicrobial, amine-containing polymer comprises an amine selected from the group consisting of a tertiary amine group and a pyridine group.

17. The process of claim 15 wherein the antimicrobial, amine-containing polymer comprises poly(4-vinylpyridine).

18. The process of claim 15 wherein the contact lens case comprises polypropylene.