Silicone hydrogel contact lenses and methods of making silicone hydrogel contact lenses

• US 8,672,475 B2
• Filed: 09/30/2010
• Issued: 03/18/2014
• Est. Priority Date: 10/01/2009
• Status: Active Grant

• Current Assignee: Coopervision International Limited (The Cooper Cos., Inc.)
• Original Assignee: Coopervision International Holding Company LP (The Cooper Cos., Inc.)
• Inventors: Liu, Yuwen, Ji, Yuan, Morsley, David, Francis, Charles, Back, Arthur
• Primary Examiner(s): WILKES, ZACHARY W
• Application Number:
  US12/894,941
• Publication Number:
  US 20110085128A1
• Time in Patent Office: 1,265 Days
• Field of Search: 351/159.35, 351/159.15, 351/159.11, 351/159.12
• US Class Current: 351/159.33
• CPC Class Codes: B29D 11/00038 Production of contact lenses
• CPC Class Codes: B29D 11/00067 Hydrating contact lenses
• CPC Class Codes: B29D 11/00346 having nanosize structures or features, e.g. fillers
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: G02C 7/049 Contact lenses having special fitting or structural features achieved by special materials or material structures

Abstract

Silicone hydrogel contact lenses, when hydrated, have a plurality of depressions on one or more of the lens surfaces. The depressions have a depth less than 1 micrometer, or less than 100 nanometers. The silicone hydrogel contact lenses have not been subject to treatment with plasma. Methods of manufacturing the silicone hydrogel contact lenses are also disclosed.

Claims

1. A method of manufacturing a silicone hydrogel contact lens, comprising:

forming a silicone hydrogel contact lens body having an anterior surface and a posterior surface, wherein, after hydration in water or an aqueous solution, at least one of the anterior surface and the posterior surface of the lens body when wet is substantially smooth and comprises a plurality of depressions extending inwardly into the lens body from the substantially smooth surface, the plurality of depressions having at least one of an average diameter between about 150 nanometers and less than 1500 nanometers and an average density from about 100 depressions per 900 μ

m² to about 1200 depressions per 900 μ

m², and wherein the lens body has not been subjected to a form of plasma treatment, the lens body has not been treated with a polymerizable swelling agent after the lens body is formed, or both, at least one of the anterior surface and the posterior surface of the lens body has an average surface roughness from about 5 nanometers RMS to about 30 nanometers RMS, and the lens body has a swell factor of at least 20%.

2. The method of claim 1, wherein the forming step comprises polymerizing a polymerizable composition comprising reactive ingredients comprising at least one silicone-containing monomer, at least one silicone-containing macromer, at least one silicone-containing prepolymer, or mixtures thereof;

at least one hydrophilic monomer and at least one crosslinking agent effective to crosslink the reactive ingredients.

3. The method of claim 2, wherein the polymerizing step occurs at least partially in a contact lens mold comprising a non-polar material.

4. The method of claim 3, wherein the non-polar material comprises polypropylene.

5. The method of claim 3, wherein the non-polar material is a nucleated thermoplastic polypropylene resin.

6. The method of claim 2, wherein the reactive ingredients comprise a silicone-containing monomer with a molecular weight less than 700 Daltons.

7. The method of claim 2, wherein the reactive ingredients comprise a silicone-containing macromer with a molecular weight between about 700 Daltons and about 2,000 Daltons.

8. The method of claim 2, wherein the reactive ingredients comprise a silicone-containing prepolymer with a molecular weight greater than 2,000 Daltons.

9. The method of claim 1, wherein the forming step comprises polymerization of a polymerizable composition in the absence of a diluent.

10. The method of claim 1, wherein the lens body is not subjected to extraction with an organic solvent or an aqueous solution including an organic solvent component prior to hydration in the water or the aqueous solution.

11. The method of claim 1, wherein after hydration in water or an aqueous solution, the at least one of the anterior surface and the posterior surface of the lens body when wet comprises a plurality of depressions with an average diameter between about 150 nanometers and less than 1500 nanometers and an average density from about 100 depressions per 900 μ

m² to about 1200 depressions per 900 μ

m².

12. A silicone hydrogel contact lens, comprising:

a silicone hydrogel lens body comprising an anterior surface and a posterior surface, wherein, after hydration in water or an aqueous solution, at least one of the anterior surface and the posterior surface of the lens body when wet is substantially smooth and comprises a plurality of depressions extending inwardly into the lens body from the substantially smooth surface, the plurality of depressions having an average diameter between about 150 nanometers and less than 1500 nanometers, and wherein the lens body has not been subjected to a form of plasma treatment, the lens body has not been treated with a polymerizable swelling agent after the lens body is formed, or both, at least one of the anterior surface and the posterior surface of the lens body has an average surface roughness from about 5 nanometers RMS to about 30 nanometers RMS, and the lens body has a swell factor of at least 20%.

13. The contact lens of claim 12, wherein the plurality of depressions have an average diameter between about 130 nanometers and less than about 630 nanometers.

14. The contact lens of claim 12, wherein the plurality of depressions have an average depth from about 4 nanometers to about 100 nanometers.

15. The contact lens of claim 12, wherein the plurality of depressions have an average density from about 5 depressions per 900 μ

m² to about 1500 depressions per 900 μ

m².

16. The contact lens of claim 12, wherein, at least 12 hours after hydration in the water or the aqueous solution, the at least one of the anterior surface and the posterior surface of the lens body has an advancing contact angle of less than 100°

and a water break up time of greater than five seconds.

17. The contact lens of claim 12, wherein the lens body is fully or partially cured while in direct contact with a contact lens mold comprising a non-polar material.

18. The contact lens of claim 12, wherein the lens body comprises a reaction product of a polymerizable composition comprising:

reactive ingredients comprising at least one silicone-containing monomer, at least one silicone-containing macromer, at least one silicone-containing prepolymer, or mixtures thereof,

at least one hydrophilic monomer, and

at least one crosslinking agent that crosslinks the reactive ingredients during polymerization to form a polymer.

19. A silicone hydrogel contact lens, comprising:

a non-plasma treated silicone hydrogel lens body comprising an anterior surface and a posterior surface, at least one of the anterior surface and the posterior surface being substantially smooth and comprising a plurality of depressions extending inwardly into the lens body from the substantially smooth surface, the plurality of depressions having an average density from about 100 depressions per 900 μ

m² to about 1200 depressions per 900 μ

m², at least one of the anterior surface and the posterior surface of the lens body has an average surface roughness from about 5 nanometers RMS to about 30 nanometers RMS, and the lens body has a swell factor of at least 20%.