ATMOSPHERIC PLASMA COATING FOR OPHTHALMIC DEVICES

• US 20120137635A1
• Filed: 11/23/2011
• Published: 06/07/2012
• Est. Priority Date: 12/01/2010
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Qiu, Yongxing, Pruitt, John Dallas, Kolluru, Chandana, Matsuzawa, Yasuo, Dunkle, Maria A.
• Granted Patent: US 9,156,213 B2
• Time in Patent Office: Days
• US Class Current: 53/433
• 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

Abstract

The invention provides a method of coating and thereby affecting the surface properties of a substrate such as a contact lens or other ophthalmic device. The method comprises the steps of generating an atmospheric plasma flow from a working gas and controlling the continuity of the atmospheric plasma flow with a power generator, and, introducing the atmospheric plasma flow to a substrate surface.

Claims

1. A method for producing ready-to-use silicone hydrogel contact lenses each having a durable plasma hydrophilic coating, comprising the steps of:

(a) generating an atmospheric plasma flow from a working gas, wherein the working gas comprises at least one organic compound selected from the group consisting of a C₁-C₁₂ alkane, an oxaalkane having up to 12 carbon atoms, a C₂-C₁₂ alkene, an oxaalkene having up to 12 carbon atoms, a C₂-C₁₂ alkyne, a C₁-C₁₂ alkanol, a cycloalkanol having up to 12 carbon atoms, an oxaallyne having up to 12 carbon atoms, a mono-clooxaalkane having up to 12 carbon atoms, a bi-clooxaalkane having up to 12 carbon atoms, a tricycloalkane having up to 12 carbon atoms, an aromatic hydrocarbon having up to 12 carbon atoms, and combinations, wherein the at least one organic compound is unsubstituted or substituted by hydroxy, amino, formyl or carboxyl, and has up to 12 carbon atoms;

(b) controlling the continuity of the atmospheric plasma flow with a power generator;

(c) introducing the atmospheric plasma flow to a surface of a wet or blot-died wet silicone hydrogel contact lens to form a plasma coating on the wet or blot-dried wet silicone hydrogel contact lens;

(d) placing and sealing the silicone hydrogel contact lens with the plasma coating thereon in a lens package containing a buffered saline; and

(e) autoclaving the sealed lens package containing the silicone hydrogel contact lens with the plasma coating thereon so as to obtain the ready-to-use silicone hydrogel contact lens, wherein the plasma coating on the ready-to-use silicone hydrogel contact lens survives autoclaving and imparts to the ready-to-use silicone hydrogel contact lens a hydrophilicity/wettability characterized by having a water-break-up time of at least about 5 seconds and/or no more than about 30% of increase in average water contact angle relative to the same plasma coating before autoclaving.

2. The method of claim 1, wherein the at least one organic compound is selected from the group consisting of an alkane having up to 8 carbon atoms, an alkyne having up to 8 carbon atoms, an alkanol having up to 8 carbon atoms, a cycloalkanol having up to 8 carbon atoms, and combinations thereof.

3. The method of claim 1, wherein the organic compound is acetylene.

4. The method of claim 1, wherein the working gas comprises air, nitrogen, oxygen, or a mixture thereof.

5. The method of claim 1, wherein the working gas comprises at least one vinylic monomer selected from the group consisting of acrylamide, methacrylamide, N,N-dimethylacrylamide, N,N-dimethylmethacrylamide, 2-acrylamidoglycolic acid, 3-acryloylamino-1-propanol, N-hydroxyethyl acrylamide, N-[tris(hydroxymethyl)methyl]-acrylamide, N-methyl-3-methylene-2-pyrrolidone, 1-ethyl-3-methylene-2-pyrrolidone, 1-methyl-5-methylene-2-pyrrolidone, 1-ethyl-5-methylene-2-pyrrolidone, 5-methyl-3-methylene-2-pyrrolidone, 5-ethyl-3-methylene-2-pyrrolidone, 1-n-propyl-3-methylene-2-pyrrolidone, 1-n-propyl-5-methylene-2-pyrrolidone, 1-isopropyl-3-methylene-2-pyrrolidone, 1-isopropyl-5-methylene-2-pyrrolidone, 1-n-butyl-3-methylene-2-pyrrolidone, 1-tert-butyl-3-methylene-2-pyrrolidone, 2-hydroxyethylmethacrylate, 2-hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, trimethylammoniurn 2-hydroxy propylmethacrylate hydrochloride, aminopropyl methacrylate hydrochloride, dimethylaminoethyl methacrylate, glycerol methacrylate, N-vinyl-2-pyrrolidone, allyl alcohol, vinylpyridine, a C₁-C₄-alkoxy polyethylene glycol methacrylate having a weight average molecular weight of up to 1500, a C₁-C₄-alkoxy polyethylene glycol acrylate having a weight average molecular weight of up to 1500, methacrylic acid, N-vinyl formamide, N-vinyl acetamide, N-vinyl isopropylamide, N-vinyl-N-methyl acetamide, N-vinyl caprolactam, and mixtures thereof.

6. The method of claim 1, wherein the working gas comprises N,N-dimethylacrylamide, 2-hydroxyethylmethacrylate, 2-hydroxyethyl acrylate, N-vinyl-2-pyrrolidone, glycerol methacrylate, a C₁-C₄-alkoxy polyethylene glycol methacrylate having a weight average molecular weight of up to 1500, a C₁-C₄-alkoxy polyethylene glycol acrylate having a weight average molecular weight of up to 1500, methacrylic acid, N-vinyl formamide, N-vinyl acetamide, N-vinyl isopropylamide, N-vinyl-N-methyl acetamide, acrylamide, methacrylamide, or a combination thereof.

7. The method of claim 1, wherein the working gas comprises a carrier gas comprising at least one inert gas selected from the group consisting of argon, helium, xenon and combinations thereof.

8. The method of claim 1, wherein the atmospheric plasma flow is introduced onto the surface of the wet or blot-dried wet silicone hydrogel contact lens through a nozzle at atmospheric pressure.

9. The method of claim 1, wherein in the step (c) a uniform plasma cloud completely surrounds or spreads over the boundary layer of a substrate surface.

10. The method of claim 1, wherein the step (c) is performed in a chamber including an entrance valve for introducing the plasma flow into the chamber and an exit valve for releasing the plasma flow from the chamber at a defined rate.

11. The method of claim 1, further comprising controlling the atmospheric plasma flow with a power amplifier, wherein the power amplifier is adapted to effect a flow that is continuous or pulsed.

12. The method of claim 1, wherein the ready-to-use silicone hydrogel contact lens has at least one property selected from the group consisting of:

(i) an averaged water contact angle of about 80 degrees or less;

(ii) an oxygen permeability of at least about 40 barrers;

(iii) an elastic modulus of from about 0.1 MPa to about 2.0 MPa; and

(iv) an equilibrium water content of from about 15% to about 55% by weight when fully hydrated; and

(vi) combinations thereof.

13. The method of claim 2, wherein the working gas comprises air, nitrogen, oxygen, or a mixture thereof.

14. The method of claim 3, wherein the working gas comprises air, nitrogen, oxygen, or a mixture thereof.

15. The method of claim 2, wherein the working gas comprises N,N-dimethylacrylamide, 2-hydroxyethylmethacrylate, 2-hydroxyethyl acrylate, N-vinyl-2-pyrrolidone, glycerol methacrylate, a C₁-C₄-alkoxy polyethylene glycol methacrylate having a weight average molecular weight of up to 1500, a C₁-C₄-alkoxy polyethylene glycol acrylate having a weight average molecular weight of up to 1500, methacrylic acid, N-vinyl formamide, N-vinyl acetamide, N-vinyl isopropylamide, N-vinyl-N-methyl acetamide, acrylamide, methacrylamide, or a combination thereof.

16. The method of claim 3, wherein the working gas comprises N,N-dimethylacrylamide, 2-hydroxyethylmethacrylate, 2-hydroxyethyl acrylate, N-vinyl-2-pyrrolidone, glycerol methacrylate, a C₁-C₄-alkoxy polyethylene glycol methacrylate having a weight average molecular weight of up to 1500, a C₁-C₄-alkoxy polyethylene glycol acrylate having a weight average molecular weight of up to 1500, methacrylic acid, N-vinyl formamide, N-vinyl acetamide, N-vinyl isopropylamide, N-vinyl-N-methyl acetamide, acrylamide, methacrylamide, or a combination thereof.

17. The method of claim 14, wherein the working gas comprises N,N-dimethylacrylamide, 2-hydroxyethylmethacrylate, 2-hydroxyethyl acrylate, N-vinyl-2-pyrrolidone, glycerol methacrylate, a C₁-C₄-alkoxy polyethylene glycol methacrylate having a weight average molecular weight of up to 1500, a C₁-C₄-alkoxy polyethylene glycol acrylate having a weight average molecular weight of up to 1500, methacrylic acid, N-vinyl formamide, N-vinyl acetamide, N-vinyl isopropylamide, N-vinyl-N-methyl acetamide, acrylamide, methacrylamide, or a combination thereof.

18. The method of claim 15, wherein the working gas comprises N,N-dimethylacrylamide, 2-hydroxyethylmethacrylate, 2-hydroxyethyl acrylate, N-vinyl-2-pyrrolidone, glycerol methacrylate, a C₁-C₄-alkoxy polyethylene glycol methacrylate having a weight average molecular weight of up to 1500, a C₁-C₄-alkoxy polyethylene glycol acrylate having a weight average molecular weight of up to 1500, methacrylic acid, N-vinyl formamide, N-vinyl acetamide, N-vinyl isopropylamide, N-vinyl-N-methyl acetamide, acrylamide, methacrylamide, or a combination thereof.

19. The method of claim 17, wherein the working gas comprises a carrier gas comprising at least one inert gas selected from the group consisting of argon, helium, xenon and combinations thereof.

20. The method of claim 18, wherein the working gas comprises a carrier gas comprising at least one inert gas selected from the group consisting of argon, helium, xenon and combinations thereof.