Wettable silicone hydrogel contact lenses and related compositions and methods
View Patent ↗Silicone hydrogel contact lenses having ophthalmically acceptable surface wettabilities are obtained from pre-extracted polymerized silicone hydrogel contact lens products having relatively large amounts of removable or extractable materials. The silicone hydrogel contact lenses can be obtained from non-polar resin based contact lens molds and without surface treatments or an interpenetrating polymeric network of a polymeric wetting agent. Related lens products, polymerizable compositions, and methods are also described.
1. A method for producing a silicone hydrogel contact lens, comprising:
providing a polymerizable silicone hydrogel lens precursor composition in a contact lens shaped cavity of a non-polar resin contact lens mold, the polymerizable silicone hydrogel precursor composition comprising a silicone-containing component and a non-silicone containing component, the non-silicone containing component being present in an amount between about 10% to about 60% (w/w) based upon the weight of all reactive components of the precursor composition and said non-silicone containing component comprising an N-vinyl pyrrolidone (NVP) monomer and a N,N-dimethylacrylamide (DMA) monomer, and the contact lens mold comprising a first contact lens mold member and a second contact lens mold member assembled together;
polymerizing the polymerizable silicone hydrogel lens precursor composition in the non-polar resin contact lens mold using heat or ultraviolet light to form a pre-extracted polymerized silicone hydrogel contact lens product having a dry weight, the pre-extracted silicone hydrogel contact lens product having a removable monomeric component in an amount of at least 10% (w/w) based on the dry weight of the pre-extracted polymerized silicone hydrogel contact lens product;
extracting and hydrating the pre-extracted polymerized silicone hydrogel contact lens product by contacting the pre-extracted polymerized silicone hydrogel contact lens product with an extraction media to produce a silicone hydrogel contact lens having a dry weight no greater than 90% of the dry weight of the pre-extracted polymerized silicone hydrogel contact lens product; and
packaging the silicone hydrogel contact lens in a contact lens package,
wherein the silicone hydrogel contact lens has an advancing contact angle less than 90 degrees, a tensile modulus less than 1.0 MPa, an oxygen permeability from about 110 barrers to about 120 barrers, and a water content from about 45% to about 55% by weight.
2. The method of claim 1 , wherein the removable monomeric component is present in an amount of at least 15% (w/w) based on the dry weight of the pre-extracted polymerized silicone hydrogel contact lens product.
3. The method of claim 1 , wherein the silicone-containing component comprises a silicone monomer, a silicone macromer, or a silicone prepolymer, or combinations thereof, each of said silicone monomer, silicone macromer, or silicone prepolymer comprising a polymerizable functional group, said polymerizable functional group being a methacrylate functional group or an acrylamide functional group.
4. The method of claim 1 , wherein the silicone-containing component comprises a silicone monomer, a silicone macromer, or a silicone prepolymer, comprising acrylamide functional groups.
5. The method of claim 1 , wherein the contact lens mold comprises a polyolefin material.
6. The method of claim 5 , wherein the contact lens mold is a polypropylene contact lens mold.
7. The method of claim 1 , wherein the extraction media comprises an alcohol.
8. The method of claim 1 , wherein the extraction media comprises a mixture of alcohol and water.
9. The method of claim 1 , wherein the precursor composition further comprises a diluent present in an amount from about 1% to about 60% (w/w) of the lens precursor composition.
10. The method of claim 1 , wherein the precursor composition further comprises a diluent in an amount from about 1% to about 60% (w/w) of the lens precursor composition, and the diluent is hexanol, ethoxyethanol, isopropanol, propanol, decanol, or silicone oil, or combinations thereof.
11. The method of claim 10 , wherein the diluent is present in an amount from about 10% to about 30% (w/w).
12. The method of claim 1 , wherein the precursor composition further comprises a diluent in an amount from about 1% to about 60% (w/w) of the lens precursor composition, and the diluent is hexanol.
13. The method of claim 1 , wherein the silicone hydrogel contact lens has a modulus of about 0.8 MPa.
14. The method of claim 1 , wherein the silicone hydrogel contact lens has a modulus of about 0.7 MPa.
15. The method of claim 1 , wherein the silicone hydrogel contact lens has a modulus of about 0.6 MPa.
16. The method of claim 1 , wherein the silicone hydrogel contact lens has an advancing contact angle less than 90 degrees, and a contact angle hysteresis from about 5 degrees to about 35 degrees, wherein the contact angle hysteresis is the difference between the advancing contact angle and a receding contact angle of the silicone hydrogel contact lens.
17. A silicone hydrogel contact lens, comprising:
a lens body having a dry weight no greater than 90% of the dry weight of the lens body prior to an extraction, wherein said lens body had at least 10% (w/w) of a removable monomeric component removed based on the dry weight of the lens body prior to removal, and wherein said lens body comprises a polymerized silicone hydrogel precursor composition comprising a silicone-containing component and a non-silicone containing component, the non-silicone containing component being present in an amount between about 10% to about 60% (w/w) based upon the weight of all reactive components of the precursor composition and comprising an N-vinylpyrrolidone (NVP) monomer and a N,N-dimethylacrylamide (DMA) monomer, and wherein the lens body is a cast molded element obtained from a non-polar resin contact lens mold polymerized using heat or ultraviolet light, wherein the silicone hydrogel contact lens has an advancing contact angle less than 90 degrees, a tensile modulus less than about 1.0 MPa, an oxygen permeability from about 110 barrers to about 120 barrers, and a water content from about 45% to about 55% by weight.
18. A silicone hydrogel contact lens, comprising:
a lens body having a dry weight no greater than 90% of the dry weight of the lens body prior to an extraction, wherein said lens body had at least 10% (w/w) of a removable monomeric component removed based on the dry weight of the lens body prior to removal, and wherein said lens body comprises a polymerized silicone hydrogel precursor composition comprising a silicone-containing component and a non-silicone containing component, the silicone-containing component comprises a silicone monomer, a silicone macromer, or a silicone prepolymer, or combinations thereof, each of said silicone monomer, said silicone macromer, or silicone prepolymer comprising a polymerizable functional group, said polymerizable functional group being a methacrylate functional group or an acrylamide functional group, the non-silicone containing component being present in an amount between about 10% to about 60% (w/w) based upon the weight of all reactive components of the precursor composition and comprising an N-vinylpyrrolidone (NVP) monomer and a N,N-dimethylacrylamide (DMA) monomer, and wherein the lens body is a cast molded element obtained from a non-polar resin contact lens mold polymerized using heat or ultraviolet light, wherein the silicone hydrogel contact lens has an advancing contact angle less than 90 degrees, a tensile modulus less than about 1.0 MPa, an oxygen permeability from about 110 barrers to about 120 barrers, and a water content from about 45% to about 55% by weight.
19. The silicone hydrogel contact lens of claim 18 , wherein the silicone-containing component comprises a silicone monomer, a silicone macromer, or a silicone prepolymer, comprising acrylamide functional groups.
20. The silicone hydrogel contact lens of claim 19 , wherein the tensile modulus is from about 0.5 MPa to about 0.8 MPa.