Cross-linkable polyionic coatings for medical devices

• US 20080226922A1
• Filed: 02/06/2008
• Published: 09/18/2008
• Est. Priority Date: 02/09/2007
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Voigt, Andreas, Schmid, Katharina, Ferreiro, Maria Gonzalez, Muller, Achim, Krohne, Lutz
• Granted Patent: US 8,147,897 B2
• Time in Patent Office: Days
• US Class Current: 428/413
• CPC Class Codes: C08J 7/056 Forming hydrophilic coatings
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: Y10T 428/31511 Of epoxy ether

Abstract

A method for making an article comprising a core material and a coating thereon, the method comprising the steps of:

(a) providing the core material;
(b) applying one or more layers of a crosslinkable polycationic material, wherein the polycationic material is a reaction product of:
(i) an epoxide of formula (I)

wherein X equals bromo, chloro, iodo, or cyano, and R¹, R², R³, R⁴, independently of one another, are selected from the group consisting of hydrogen, linear or branched C₁-C₆-alkyl, and linear or branched C₁-C₆-alkyl which is substituted with halogen, and
(ii) a polymer having repeating units comprising one or more secondary or tertiary amine group(s);
(c) applying one or more layers of a polyanionic material; and
(d) cross-linking the layers of polyelectrolytes formed by steps (b) and (c).

The articles obtainable by the method of the invention have desirable characteristics regarding adherence to the core material, durability, hydrophilicity, and wettability and are thus useful for the manufacture of medical articles such as ophthalmic devices.

Claims

1. A method for making an article comprising a core material and a coating thereon, the method comprising the steps of:

(a) providing the core material;

(b) applying one or more layers of a crosslinkable polycationic material, wherein the polycationic material is a reaction product of;

(i) an epoxide of formula (I)

2. The method according to claim 1, wherein X equals chloro and R¹, R², R³, R⁴ are each hydrogen.

3. The method according to claim 1 or 2, wherein the repeating units of the polymer comprise one or more secondary amine group(s).

4. The method according to claim 3, wherein the secondary amine groups comprising polymer is selected from the group consisting of a poly(alkylene imine) and a poly(amidoamine).

5. The method according to claim 4, wherein the poly(amidoamine) is a polycondensate derived from a polyamine and a dicarboxylic acid.

6. The method according to claim 5, wherein the poly(amidoamine) is a polycondensate derived from diethylene triamine and adipic acid.

7. The method device according to any one of claims 1 to 6, wherein the polyanionic material is selected from the group consisting of carboxy substituted carbohydrates, alginates, polyacrylic acid, polymethacrylic acid, and mixtures thereof.

8. The method according to claim 7, wherein the polyanionic material is a carboxymethyl cellulose.

9. The method according to claim 8, wherein the polyanionic material is a carboxymethyl cellulose and the poly(amidoamine) is a polycondensate derived from diethylene triamine and adipic acid.

10. The method according to any one of claims 1 to 9, wherein the article is an ophthalmic device.

11. The method of claim 10, wherein the ophthalmic device is a contact lens.

12. The method according to any one of claims 1 to 11, wherein the core material is made of a silicone hydrogel.

13. The method according to any one of claims 1 to 12, wherein the crosslinking is achieved by a heat sterilization process.

14. An article obtained by the method of any one of claims 1 to 13.

15. The article according to claim 14, which is an medical device, preferably an ophthalmic device, and more preferably a contact lens.

16. Use of a crosslinkable polycationic material according to any one of claims 1 to 6 for coating a medical device.