Process for surface modifying substrates and modified substrates resulting therefrom

• US 6,852,353 B2
• Filed: 07/23/2001
• Issued: 02/08/2005
• Est. Priority Date: 08/24/2000
• Status: Expired due to Term

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Lally, John Martin, Winterton, Lynn Cook, Qiu, Yongxing
• Primary Examiner(s): Michener, Jennifer Kolb
• Application Number:
  US09/911,218
• Publication Number:
  US 20030143335A1
• Time in Patent Office: 1,296 Days
• Field of Search: 427/169, 427/414, 427/415, 427/248.1, 427/2.1, 427/2.24, 427/2.25, 427/2.28, 427/2.3, 427/164, 427/168, 427/407, 427/421, 427/430.1
• US Class Current: 427/2.24
• CPC Class Codes: A61L 27/34 Macromolecular materials
• CPC Class Codes: C08J 7/16 with polymerisable compounds
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

The present invention generally relates to a method of modifying the surface of substrates such as contact lenses and other biomedical articles by at least partially coating the surfaces of such substrates with a polymeric tie layer having reactive sites. Various other moieties may then be chemically attached to the article surface by reaction of the other moieties with the reactive sites through classical chemical attachment mechanisms.

Claims

1. A method for modifying the surface of an article, said method comprising the steps of:

a) depositing at least a polyelectrolytic tie layer onto the surface of said article, wherein said polyelectrolytic tie layer is composed of (i) one layer of a first polyionic material which is adsorbed onto, heteropolarly bound onto, and/or entraped on the surface of the article or (ii) at least one layer of the first polyionic material which is adsorbed onto, heteropolarly bound onto, and/or entraped on the surface of the article and at least one layer of a second polyionic material having charges opposite of the charges of the first polyionic material, wherein said first and second polyionic materials have functional group which provide reactive sites; and

b) covalently linking a layer of an active agent to said reactive sites, wherein the active agent is an anti-microbial agent or a polymerization initiator capable of initiating a radical polymerization of ethylenically unsaturated compounds.

2. The method of claim 1 wherein, in the step of depositing, two or more polyelectrolytic tie layers are successively deposited onto said article surface.

3. The method of claim 1 wherein, in the step of depositing, one polyelectrolytic tie layer is deposited onto said article surface.

4. The method of claim 1 wherein said polyelectrolytic tie layer is deposited onto said article surface by contacting said article with one or more polyionic material solutions.

5. The method of claim 4 wherein said layer is deposited by dipping said article into a first solution comprising the first polyionic material having positive or negative charges, removing said article from said first solution, dipping said article into a second solution comprising the second polyionic material having charges that are opposite of the charges of the first polyionic material, and removing said article from said second solution.

6. The method of claim 4 wherein said polyelectrolytic tie layer is deposited onto said article surface by dipping said article into a solution comprising the first polyionic material and the second polyionic material and then removing said article from said solution.

7. The method of claim 4 wherein said contacting occurs by spraying a solution onto the medical device.

8. The method of claim 7 wherein said polyelectrolytic tie layer is deposited by spraying said article with a first solution comprising the first polyionic material having positive or negative charges and then spraying said article with a second solution comprising the second polyionic material having charges opposite of the charges of the first polyionic material.

9. The method of claim 7 wherein said polyelectrolytic tie layer is deposited onto said article surface by spraying said article with a solution comprising the first polyionic material and the second polyionic material.

10. The method of claim 1 wherein said article is a biomedical device.

11. The method of claim 10 wherein said biomedical device is a contact lens.

12. The method of claim 1 wherein said polyelectrolytic layer is deposited onto said article surface by spin-coating said article.

13. The method of claim 1 wherein said polyelectrolytic tie layer is deposited onto said article surface by vapor deposition.

14. The method of claim 4, wherein said polyelectrolytic tie layer is deposited onto the surface of said article by:

(1) spraying said article with a first solution comprising the first polyionic material and then dipping said article into a second solution comprising the second polyionic material having charges opposite of the changes of the first polyionic material;

or (2) dipping said article into the first solution comprising the first polyionic material and then spraying said article with the second solution comprising the second polyionic material having charges opposite of the charges of the first polyionic material.

15. The method of claim 1, wherein the active agent is a polymerization initiator capable of initiating a radical polymerization of ethylenically unsaturated compounds, and wherein the method further comprises the steps of:

(c) contacting the initiator-modified article with a solution of a hydrophilic monomer or macromer; and

(d) graft-polymerizing the hydrophilic monomer or macromer onto on the surface of the article.

16. The method of claim 15, wherein the step (c) is carried out by immersing the article in the solution or depositing a layer of the hydrophilic monomer or macromer on the initiator-modified article surface by dipping, spraying, spreading, knife coating, pouring, rolling, spin coating, or vacuum vapor depositing technique.

17. The method of claim 16, wherein the solution is a solution of a hydrophilic monomer selected from the group consisting of hydroxy-substituted C₂-C₄-alkyl acrylate, hydroxy-substituted C₂-C₄-alkyl methacrylate, acrylamide, methacrylamide, N,N-di-C₁-C₄-alkyl acrylamide, N,N-di-C₁-C₄-alkyl methacrylamide, hydroxy-substituted C₂-C₄-alkyl acrylamide, hydroxy-substituted C₂-C₄-alkyl methacrylamide, hydroxy-substituted C₁-C₄-alkyl vinyl ether, 2-acrylamido-2-methylpropanesulfonic acid, N-vinylpyrrole, N-vinylsuccinimide N-vinylpyrrolidone, 2-vinylpyridine, 4-vinylpyridine, acrylic acid, methacrylic acid, mono-C₁-C₄-alkylamino-C₁-C₄-alkyl acrylate, mono-C₁-C₄-alkylamino-C₁-C₄-alkyl methacrylate, di-C₁-C₄-alkylamino-C₁-C₄-alkyl acrylate, di-C₁-C₄-alkylamino-C₁-C₄-alkyl methacrylates, and allylalcohol.

18. The method of claim 16, wherein the solution is a solution of a hydrophilic macromer.

19. The method of claim 1, wherein the active agent is an antimicrobial agent having a functional group capable of reacting with the functional groups of the first polyionic material and/or the second polyionic material.