Silicone hydrogel contact lenses
View Patent ↗Silicone hydrogels, including vinyl carbonate endcapped polysiloxanes containing a fluorinated side chain, are useful as biomaterials, especially hydrogel biomaterials, including contact lens materials. The hydrogels are the hydrated polymerization product of a monomer mixture comprising a hydrophilic monomer and a polysiloxane-containing monomer, have an oxygen permeability of at least about 120 Barrers, a water content of at least about 20 weight percent, and a modulus no greater than about 83 g/mm 2 .
1. A hydrogel that is the hydrated polymerization product of a monomer mixture comprising a hydrophilic monomer selected from the group consisting of N-vinyl-N-methyl acetamide, N-vinyl-N-ethyl acetamide, N-vinyl-N-ethyl formamide, N-vinyl formamide, N-vinyl pyrrolidone and mixtures thereof, and a polysiloxane-containing monomer, wherein said 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 40 to 57 g/mm 2 .
2. The hydrogel of claim 1 , having a modulus from 51 to 57 g/mm 2 .
3. The hydrogel of claim 1 , having a modulus from 40 to 51 g/mm 2 .
4. The hydrogel of claim 1 , having a water content from 23.6% to 30.5% by weight.
5. The hydrogel of claim 2 , having a water content from 23.6% to 30.5% by weight.
6. The hydrogel of claim 1 , having an oxygen permeability from 127 Barrers to 147 Barrers.
7. The hydrogel of claim 1 , wherein said monomer mixture further comprises a monofunctional polysiloxanylalkyl monomer.
8. The hydrogel 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.
9. The hydrogel of claim 8 , wherein the monofunctional polysiloxanylalkyl monomer is selected from the group consisting of 3-[tris(trimethylsiloxy)silyl] propyl vinyl carbamate and 3-[tris(trimethylsiloxy)silyl] propyl vinyl carbonate.
10. The hydrogel of claim 1 , wherein the hydrophilic monomer includes N-vinyl pyrrolidinone.
11. A contact lens made from the polymerization product of a monomer mixture that comprises a hydrophilic monomer selected from the group consisting of N-vinyl-N-methyl acetamide, N-vinyl-N-ethyl acetamide, N-vinyl-N-ethyl formamide, N-vinyl formamide, N-vinyl pyrrolidone and mixtures thereof, and a polysiloxane-containing monomer, wherein said contact lens is composed of a hydrogel having an oxygen permeability of at least about 120 Barrers, a water content of at least about 20 weight percent, and a modulus from 40 to 57 g/mm 2 .
12. The contact lens of claim 11 , having a modulus from 51 to 57 g/mm 2 .
13. The contact lens of claim 11 , having a modulus from 40 to 51 g/mm 2 .
14. The contact lens of claim 11 , having a water content from 23.6% to 30.5% by weight.
15. The hydrogel of claim 12 , having a water content from 23.6% to 30.5% by weight.
16. The contact lens of claim 11 , having an oxygen permeability from 127 Barrers to 147 Barrers.
17. The contact lens of claim 11 , wherein the hydrophilic monomer includes N-vinyl pyrrolidinone.
18. The contact lens of claim 11 , wherein said monomer mixture further comprises a monofunctional polysiloxanylalkyl monomer.
19. The contact lens of claim 18 , 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.
20. The contact lens of claim 19 , wherein the monofunctional polysiloxanylalkyl monomer is selected from the group consisting of 3-[tris(trimethylsiloxy)silyl] propyl vinyl carbamate and 3-[tris(trimethylsiloxy)silyl] propyl vinyl carbonate.
21. A hydrogel that is the hydrated polymerization product of a monomer mixture comprising a hydrophilic monomer and a polysiloxane-containing monomer, wherein said hydrogel has an oxygen permeability of at least about 120 Barrers, a water content from 23.6% to 30.5% by weight, and a modulus from 40 to 57 g/mm 2 .
22. The hydrogel of claim 21 , having a modulus from 51 to 57 g/mm 2 .
23. The hydrogel of claim 21 , having a modulus from 40 to 51 g/mm 2 .
24. A contact lens made from the polymerization product of a monomer mixture that comprises a hydrophilic monomer and a polysiloxane-containing monomer, wherein said contact lens is composed of a hydrogel having an oxygen permeability of at least about 120 Barrers, a water content from 23.6% to 30.5% by weight, and a modulus from 40 to 57 g/mm 2 .
25. The contact lens of claim 24 , having a modulus from 51 to 57 g/mm 2 .
26. The contact lens of claim 24 , having a modulus from 40 to 51 g/mm 2 .