Contact lenses with mucin affinity

• US 20070116741A1
• Filed: 11/21/2005
• Published: 05/24/2007
• Est. Priority Date: 11/21/2005
• Status: Abandoned Application

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: McGee, Joseph, Valint, Paul, Vanderbilt, David
• Application Number:
  US11/284,025
• Publication Number:
  US 20070116741A1
• Time in Patent Office: Days
• US Class Current: 424/428
• CPC Class Codes: A61L 27/34 Macromolecular materials
• CPC Class Codes: A61L 27/50 Materials characterised by their function or physical properties , e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

A biomedical device surface, such as a contact lens surface, is covalently linked to a cationic copolymer. The copolymer may include monomeric units derived from an ethylenically unsaturated monomer containing a quaternary ammonium moiety and monomeric units derived from an ethylenically unsaturated monomer containing a moiety reactive with complementary reactive functionalities at the lens surface. The copolymer may be covalently linked directly to the lens surface, or covalently linked with an intermediate polymer reactive with both the lens surface and the copolymer.

Claims

1. a biomedical device comprising a surface covalently linked to a cationic copolymer.

2. The biomedical device of claim 1, wherein the copolymer comprises cationic monomeric units and hydrophobic monomeric units.

3. The biomedical device of claim 1, which is an ophthalmic device.

4. The biomedical device of claim 3, which is a contact lens.

5. The contact lens of claim 4, wherein the copolymer comprises monomeric units derived from an ethylenically unsaturated monomer containing a quaternary ammonium moiety.

6. The contact lens of claim 5, wherein the copolymer comprises monomeric units derived from at least one of formula (X) or formula (XI):

—

(R¹¹)—

N⁺(R¹²)(R¹³)(R¹⁴) 

 

(X)

wherein;

R¹¹ is C(1-3) alkylene; and

each of R¹², R¹³ and R¹⁴ is independently methyl or ethyl;

—

(R²¹)—

N⁺(R²²)(R²³)(R²⁴) 

 

(XI)

wherein;

R²¹ is C(1-10) alkylene or fluoroalkylene;

each of R²² and R²³ is independently methyl or ethyl; and

R²⁴ is C(4-22) alkyl or fluoroalkyl.

7. The contact lens of claim 6, wherein the copolymer comprises monomeric units derived from both formula (X) or formula (XI).

8. The contact lens of claim 6, wherein the copolymer comprises monomeric units derived from formula (X) and a non-cationic, ethylenically unsaturated hydrophobic monomer.

9. The contact lens of claim 4, wherein the copolymer further comprises monomeric units derived from an ethylenically unsaturated monomer containing a moiety reactive with complementary reactive functionalities at the lens surface.

10. The contact lens of claim 9, wherein the copolymer is covalently linked to the lens surface with the moiety reactive with the complementary functionality at the lens surface.

11. The contact lens of claim 4, wherein the copolymer comprises:

hydrophilic, cationic monomeric units;

hydrophobic, cationic monomeric units; and

monomeric units derived from an ethylenically unsaturated monomer containing a moiety reactive with complementary reactive functionalities at the lens surface.

12. The contact lens of claim 11, wherein the copolymer further comprises monomeric units derived from a non-cationic, ethylenically unsaturated hydrophilic monomer in an amount sufficient to render the copolymer water soluble.

13. The contact lens of claim 4, wherein the copolymer is covalently bound to the lens surface through primary amine or hydroxyl radicals at the lens surface.

14. The contact lens of claim 4, wherein the copolymer is linked to the lens surface with an intermediate polymer reactive with both the lens surface and the copolymer.

15. The contact lens of claim 14, wherein the intermediate polymer is covalently linked to the lens surface and to the cationic copolymer.

16. The contact lens of claim 15, wherein the copolymer comprises:

cationic monomeric units; and

monomeric units derived from an ethylenically unsaturated monomer containing a moiety reactive with complementary reactive functionalities of the intermediate polymer.

17. The contact lens of claim 16, wherein the copolymer further comprises monomeric units derived from a non-cationic, ethylenically unsaturated hydrophilic monomer in an amount sufficient to render the copolymer water soluble.

18. The biomedical device of claim 1, wherein the cationic copolymer complexes with mucin.

19. The contact lens of claim 4, wherein the cationic copolymer complexes with epithelial mucin.

20. The contact lens of claim 4, wherein the cationic copolymer is complexed with epithelial mucin.

21. A method comprising covalently linking to a biomedical device surface a cationic copolymer.

22. The method of claim 21, wherein the biomedical device is an ophthalmic device.

23. The method of claim 22, which is a contact lens.

24. The method of claim 23, wherein the copolymer comprises reactive moieties that are covalently linked to complementary reactive functionalities on the lens surface.

25. The method of claim 24, further comprising subjecting the surface of the lens to a plasma treatment that provides the complementary reactive functionalities on the lens surface.

26. The method of claim 24, wherein an intermediate polymer is linked to the lens surface, and the cationic copolymer is linked to the intermediate polymer.

27. The method of claim 26, wherein the intermediate polymer is reactive with reactive functionality on the lens surface and reactive functionalities on the cationic copolymer.

28. The method of claim 27, further comprising subjecting the surface of the lens to a plasma treatment that provides complementary reactive functionalities on the lens surface for the intermediate polymer.

29. The method of claim 23, further comprising placing the contact lens in the eye, whereby mucin complexes with the cationic copolymer.

30. A biomedical device comprising a cationic copolymer covalently linked to a surface of the device, said copolymer complexing with epithelial mucin.

31. The biomedical device of claim 30, which is a contact lens, said copolymer complexing with epithelial mucin.

32. A copolymer comprising:

monomeric units derived from an ethylenically unsaturated monomer containing a quaternary ammonium moiety;

monomeric units derived from an ethylenically unsaturated hydrophobic monomer; and

monomeric units derived from an ethylenically unsaturated monomer containing a moiety reactive with complementary reactive functionalities at a biomedical device surface.