Silicone hydrogels based on fluorinated polysiloxanes

1. A silicone hydrogel that is the hydrated polymerization product of a monomer mixture comprising N-vinyl pyrrolidnone, a monofunctional polysiloxanylalkyl monomer, and a polysiloxane-containing monomer having a perfluorinated side chain on a terminal carbon, wherein said silicone hydrogel has an oxygen permeability of at least about 120 Barrers, a water content of at least about 20 weight percent, and a modulus from 61 to 97 g/mm 2 .

2. The hydrogel of claim 1 wherein the monofunctional polysiloxanylalkyl monomer is represented by the formula:

wherein:

X denotes —OCOO—, or —OCONR 4 — where each R 4 is H or lower alkyl;

R 3 denotes hydrogen or methyl;

h is 1 to 10; and

each R 2 independently denotes a lower alkyl or halogenated alkyl radical, a phenyl radical or a radical of the formula —Si(R 5 ) 3 wherein each R 5 is independently a lower alkyl radical or a phenyl radical.

3. The hydrogel of claim 1 having a modulus from 70 to 92 g/mm 2 .

4. The hydrogel of claim 1 having a water content from 21.5% to 26.9% by weight.

5. The hydrogel of claim 3 having a water content from 21.5% to 24.7% by weight.

6. The hydrogel of claim 1 wherein the polysiloxane-containing monomer having a perfluorinated side chain is present in the monomer mixture from 25% to 41% by weight of total monomer in the monomer mixture.

7. A silicone hydrogel contact lens made from the polymerization product of a monomer mixture that comprises N-vinyl pyrrolidone, a monofunctional polysiloxanylalkyl monomer, and a polysiloxane-containing monomer having a perfluorinated side chain on a terminal carbon, wherein said silicone hydrogel contact lens has an oxygen permeability of at least about 120 Barrers, a water content of at least about 20 weight percent, and a modulus from 61 to 97 g/mm 2 .

8. The contact lens of claim 7 wherein said hydrated polymerization product further comprises monomeric units of N-vinyl-N-methyl acetamide.

9. The contact lens of claim 7 wherein the monofunctional polysiloxanylalkyl monomer is represented by the formula:

wherein:

X denotes —OCOO—, or —OCONR 4 — where each R 4 is H or lower alkyl;

R 3 denotes hydrogen or methyl;

h is 1 to 10; and

each R 2 independently denotes a lower alkyl or halogenated alkyl radical, a phenyl radical or a radical of the formula —Si(R 5 ) 3 wherein each R 5 is independently a lower alkyl radical or a phenyl radical.

10. The contact lens of claim 9 wherein the monofunctional polysiloxanylalkyl monomer is selected from the group consisting of 3-[tris(trimethylsiloxy)silyl]propyl vinylcarbamate and 3-[tris(trimethylsiloxy)silyl]propyl vinylcarbonate.

11. The contact lens of claim 7 having a modulus from 70 to 92 g/mm 2 .

12. The contact lens of claim 7 having a water content from 21.5% to 26.9% by weight.

13. The contact lens of claim 7 wherein the polysiloxane-containing monomer having a perfluorinated side chain is present in the monomer mixture from 25% to 41% by weight of total monomer in the monomer mixture.

14. The contact lens of claim 12 having an oxygen permeability from 120.9 Barrers to 133.6 Barrers.

15. A silicone hydrogel contact lens made from the polymerization product of a monomer mixture that comprises N-vinyl-N-methyl acetamide and N-vinyl pyrrolidone, a monofunctional polysiloxanylalkyl monomer, and a polysiloxane-containing monomer having a perfluorinated side chain on a terminal carbon, wherein said silicone hydrogel contact lens has an oxygen permeability of at least about 120 Barrers, a water content of at least about 20 weight percent, and a modulus from 61 to 97 g/mm 2 .

16. The contact lens of claim 15 having an oxygen permeability from 120.9 Barrers to 133.6 Barrers.

17. The contact lens of claim 15 having a modulus from 70 to 92 g/mm 2 .

18. The contact lens of claim 15 wherein the polysiloxane-containing monomer having a perfluorinated side chain is present in the monomer mixture from 25% to 41% by weight of total monomer in the monomer mixture.