Renewable surface treatment of silicone medical devices with reactive hydrophilic polymers

• US 6,599,559 B1
• Filed: 04/03/2000
• Issued: 07/29/2003
• Est. Priority Date: 04/03/2000
• Status: Expired due to Fees

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: Bonafini, James A. Jr., McGee, Joseph A., Valint, Paul L. Jr.
• Primary Examiner(s): Beck, Shrive P.
• Assistant Examiner(s): MARKHAM, WESLEY D
• Application Number:
  US09/541,588
• Time in Patent Office: 1,212 Days
• Field of Search: 427/2.1, 427/162, 427/164, 427/355, 427/2.24, 427/154, 427/155, 427/430.1, 427/444, 427/140, 427/371, 351/160.R, 351/160.M, 510/112-115
• US Class Current: 427/2.24
• CPC Class Codes: A61L 27/34 Macromolecular materials
• 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 7/048 Forming gas barrier coatings
• CPC Class Codes: C08J 7/056 Forming hydrophilic coatings
• CPC Class Codes: C08L 43/04 Homopolymers or copolymers of monomers containing silicon
• CPC Class Codes: C08L 83/00 Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: Y10T 428/31511 Of epoxy ether
• CPC Class Codes: Y10T 428/31663 As siloxane, silicone or silane

Abstract

The present invention is directed toward the renewable surface treatment of medical devices such as contact lenses and medical implants. In particular, the present invention is directed to a method of modifying the surface of a medical device to increase its biocompatibility or hydrophilicity by coating the device with a removable hydrophilic polymer by means of reaction between reactive functionalities on the hydrophilic polymer which functionalities are complementary to reactive functionalities on or near the surface of the medical device. The present invention is also directed to a contact lens or other medical device having such a surface coating.

Claims

1. A method for treating the surface of a medical device comprising:

(a) forming a medical device from a material comprising monomeric units having reactive functionalities selected from the group consisting of azlactone, carboxylic acid, amine, hydroxy and epoxy functionalities, and combinations thereof;

(b) forming a hydrophilic reactive polymer having complementary reactive functionalities along the polymer chain, said complementary reactive functionalities selected from the group consisting of azlactone, isocyanate, acid anhydride, epoxy, hydroxy, primary amine, secondary amine and carboxylic acid functionalities, and combinations thereof, wherein;

when the hydrophilic reactive polymer comprises hydroxy or amine complementary reactive functionalities, the medical device monomeric units comprise azlactone reactive functionalities, or when the hydrophilic reactive polymer comprises carboxylic acid complementary functionality, the medical device monomeric units comprise epoxy reactive functionalities;

(c) reacting the hydrophilic reactive polymer of (b) having complementary reactive functionalities along the polymer chain with said medical device monomeric unit reactive functionalities on or near the surface of the medical device of (a), thus forming a biocompatible surface on the medical device;

(d) removing the biocompatible surface of step (c); and

(e) repeating steps (b) and (c) to form a renewed biocompatible surface on said medical device having properties similar to the original biocompatible surface of step (c).

2. The method of claim 1, wherein the medical device is a silicone contact lens or intraocular lens and the hydrophilic reactive polymer is uncolored.

3. The method of claim 1, wherein the medical device is a silicone hydrogel, continuous-wear contact lens.

4. The method of claim 3 wherein said removing step (d) further comprises abrading said biocompatible surface with an abrasive particulate in an aqueous carrier solution.

5. The method of claim 4, wherein said abrasive particulate comprises silica or alumina.

6. The method of claim 1, wherein the hydrophilic reactive polymer comprises 1 to 100 mole percent of monomeric units having said reactive functionalities.

7. The method of claim 1, wherein the hydrophilic reactive polymer comprises 0 to 99 mole percent of monomeric units that are derived from non-reactive hydrophilic monomers.

8. The method of claim 1, wherein the polymer comprises 50 to 95 mole percent of monomeric units derived from non-reactive hydrophilic monomers selected from the group consisting of acrylamides, lactones, poly(alkylenepoxy)methacrylates, methacrylic acid or hydroxyalkyl methacrylates and 5 to 50 percent of monomeric units derived from functionally reactive monomers selected from the group consisting of epoxy, azlactone, and anhydride containing monomers.

9. The method of claim 1, wherein the medical device comprises a silicone hydrogel that is a polymerization product of a mixture comprising a silicon-containing monomer and a hydrophilic monomer.

10. The method of claim 1, wherein the hydrophilic reactive polymer comprises 0 to 35 mole percent monomeric units derived from hydrophobic monomers.

11. The method of claim 1, wherein the hydrophilic polymer comprises oxazolinone moieties having the following formula:

wherein R³ and R⁴ independently can be an alkyl group having 1 to 14 carbon atoms;

a cycloalkyl group having 3 to 14 carbon atoms;

an aryl group having 5 to 12 ring atoms;

an arenyl group having 6 to 26 carbon atoms; and

0 to 3 heteroatoms selected from S, N, and nonperoxidic 0;

or R³ and R⁴ taken together with the carbon to which they are joined can form a carbocyclic ring containing 4 to 12 ring atoms, and n is an integer 0 or 1.

12. The method of claim 11, wherein the polymer comprises the reaction product of a mixture of monomers comprising the monomer represented by the general formula:

where R¹ and R² independently denote a hydrogen atom or a lower alkyl radical with one to six carbon atoms, and R³ and R⁴ independently denote alkyl radicals with one to six carbon atoms or a cycloalkyl radicals with 5 or 6 carbon atoms.

13. The method of claim 12, wherein the monomer is selected from the group consisting of 2-isopropenyl-4,4-dimethyl-2-oxazolin-5-one and 2-vinyl-4,4-dimethyl-2-oxazolin-5-one.

14. The method of claim 11, in the medical device is dipped in a solution comprising at least one hydrophilic reactive polymer in the absence of a coloring substance.

15. The method of claim 1 wherein said removing step (d) further comprises abrading said biocompatible surface.

16. The method of claim 1, wherein the medical device is a rigid contact lens.

17. The method of claim 16, wherein the rigid contact lens is a rigid-gas-permeable contact lens.