Plasma surface treatment of silicone hydrogel contact lenses with a flexible carbon coating

• US 6,213,604 B1
• Filed: 05/20/1999
• Issued: 04/10/2001
• Est. Priority Date: 05/20/1999
• Status: Expired due to Fees

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: McGee, Joseph A., Grobe, George L. III, Valint, Paul L. Jr., Ammon, Daniel M. Jr.
• Primary Examiner(s): Sugarman, Scott J.
• Application Number:
  US09/315,558
• Time in Patent Office: 691 Days
• Field of Search: 351/160.R, 351/160.H, 351/161, 351/162, 351/177, 427/574
• US Class Current: 351/177
• CPC Class Codes: B29D 11/00038 Production of contact lenses
• CPC Class Codes: B29D 11/00865 Applying coatings; tinting; colouring printing, marking or copying processes B41M; identification in general G09F3/00; producing decorative effects in general B44C; positioning or marking of lenses B24B13/0055
• CPC Class Codes: C08J 2383/04 Polysiloxanes
• CPC Class Codes: C08J 7/056 Forming hydrophilic coatings
• CPC Class Codes: C08J 7/06 with compositions not containing macromolecular substances
• CPC Class Codes: C08J 7/123 Treatment by wave energy or particle radiation C08J7/18 takes precedence
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

The present invention is directed to the surface treatment of silicone hydrogel contact lenses. In particular, the present invention is directed to a method of modifying the surface of a contact lens to increase its hydrophilicity by coating the lens with a carbon-containing layer made from a diolefinic compound having 4 to 8 carbon atoms. In one embodiment, an optically clear, hydrophilic coating is provided upon the surface of a silicone hydrogel lens by sequentially subjecting the surface of the lens to: a plasma oxidation reaction, followed by a plasma polymerization reaction in a the presence of a diolefin in the absence of air. Finally, the resulting carbon layer is rendered hydrophilic by a further plasma oxidation reaction or by the attachment of a hydrophilic polymer chains.

Claims

1. A method for treating the surface of a silicone hydrogel contact lens, which method comprises the sequential steps of:

(a) subjecting the surface of the lens to a plasma oxidation reaction;

(b) subjecting the oxidized surface of the lens to a plasma polymerization reaction in a hydrocarbon atmosphere comprising a diolefin having four to eight carbon atoms in the effective absence of oxygen, to form a carbon layer having a thickness of at least 50 to 500 Angstroms; and

(c) rendering the carbon layer of step (b) hydrophilic by either subjecting the surface to a plasma oxidization or by a secondary coating of a hydrophilic polymer.

2. The method of claim 1, wherein the lens surface of step (b) is subjected to a plasma oxidation with an oxidizing source of oxygen or nitrogen to form a hydrophilic surface by creating hydrophilic functional groups on the surface of the carbon layer.

3. The method of claim 1, wherein the lens surface of step (b) is coated with hydrophilic polymeric chains either by a free-radical graph polymerization or by the attachment of preformed polymers containing a reactive group that bonds to complementary reactive groups on the suface of the lens.

4. The method of claim 1, wherein the plasma oxidation in step (b) is carried out at 10 to 1000 watts for a period of 10 seconds to 10 minutes, at a pressure of 0.001 to 1.0 torr.

5. The method of claim 1, wherein the oxidation reaction of steps (a) and (c) are independently conducted in an oxygen or nitrogen containing atmosphere selected from at least one of ambient air, oxygen gas, hydrogen peroxide, ammonia, water, and combinations thereof.

6. The method of claim 1, wherein the plasma polymerization reaction of step (b) is conducted in an atmosphere comprising isoprene and/or 1,3-butadiene.