Soft contact lenses

• US 6,943,203 B2
• Filed: 09/20/2001
• Issued: 09/13/2005
• Est. Priority Date: 03/02/1998
• Status: Expired due to Term

• Current Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Original Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Inventors: Hargiss, Marcie V., Love, Robert N., McCabe, Kevin P., Steffen, Robert B., Molock, Frank F., Turner, David C., Enns, John B., Hill, Gregory A., Vanderlaan, Douglas G., Alli, Azaam, Ford, James D., Maiden, Annie C.
• Primary Examiner(s): PENG, KUO LIANG
• Application Number:
  US09/957,299
• Publication Number:
  US 20020107324A1
• Time in Patent Office: 1,454 Days
• Field of Search: 525/288, 525/299, 525/301, 525/303, 526/279, 528/32, 523/106, 523/107
• US Class Current: 523/107
• CPC Class Codes: C08F 230/08 containing silicon
• CPC Class Codes: C08F 290/068 Polysiloxanes
• CPC Class Codes: C08L 43/04 Homopolymers or copolymers of monomers containing silicon
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

A soft contact lens containing a silicone-hydrogel made by curing a reaction mixture containing a silicone-containing monomer.

Claims

1. A contact lens comprising a silicone hydrogel comprising a mono-alkyl terminated polydiorganosiloxane having the structure:

where b=0 to 100;

R₅₈ is a monovalent group comprising at least one ethylenically unsaturated moiety;

each R₅₉ is independently a monovalent alkyl, or aryl group, which may be further substituted with alcohol, amine, ketone, carboxylic acid or ether groups;

R₆₀ is a monovalent alkyl, or aryl group, which may be further substituted with alcohol, amine, ketone, carboxylic acid or ether groups, and R₆₁ is independently alkyl or aromatic, or a monovalent siloxane chain comprising from 1 to 100 repeating Si—

O units;

wherein said silicone hydrogel comprises a Young'"'"'s modulus less than about 180 psi and a tan δ

of equal to or less than about 0.25 at a frequency of 1 Hz at 25°

C., provided that said mono-alkyl terminated polydiorganosiloxane is not a hydroxyalkylamine-functional silicone-containing monomer.

2. The contact lens of claim 1, wherein said silicone hydrogel has a Young'"'"'s modulus of less than about 100 psi.

3. The contact lens of claim 1, wherein said silicone hydrogel further comprises an O₂ Dk greater than about 40 barrer.

4. The contact lens of claims 1, 2, or 3, wherein said silicone hydrogel comprises about 2-70% wt of said mono-alkyl terminated polydiorganosiloxane, based on the total weight of reactive monomer.

5. The contact lens of claim 1, wherein b=4 to 16, R₅₈ is a monovalent group containing at least one styryl, vinyl, or methacrylate moiety, each R₅₉ is methyl, R₆₀ is C_3-8 alkyl group, and R₆₁ is methyl.

6. The contact lens of claim 1, wherein b=8 to 10, R₅₈ is a methacrylate moiety;

each R₅₉ is methyl, R₆₀ is a butyl group, and R₆₁ is methyl.

7. The contact lens of claim 1, wherein the mono-alkyl terminated polydiorganosiloxane is a monomethacryloxypropyl terminated polydimethylsiloxane.

8. The contact lens of claim 1, wherein said silicone hydrogel has a Young'"'"'s modulus of about 30-160 psi.

9. The contact lens of claim 1, wherein said silicone hydrogel has a Young'"'"'s modulus of about 40-130 psi.

10. The contact lens of claim 1, further comprising a surface layer that is more hydrophilic than said silicone hydrogel.

11. The contact lens of claim 10, further comprising a coating that is more hydrophilic than said silicone hydrogel.

12. The contact lens of claim 10, wherein the surface layer comprises poly(acrylic acid).

13. A silicone hydrogel contact lens comprising a (CT) of about 50 to about 160 μ

m and a Young'"'"'s modulus (B) of about 40 to about 300 psi, wherein (E)(CT)² is less than about 1 psi·

mm² wherein said silicone hydrogel comprises a mono-alkyl terminated polydiorganosiloxane having the structure;

where b=0 to 100;

R₅₈ is a monovalent group comprising at least one ethylenically unsaturated moiety;

each R₅₉ is independently a monovalent alkyl, or aryl group, which may be further substituted with alcohol, amine, ketone, carboxylic acid or ether groups;

R₆₀ is a monovalent alkyl, or aryl group, which may be further substituted with alcohol, amine, ketone, carboxylic acid or ether groups, and R₆₁ is independently alkyl or aromatic, or a monovalent siloxane chain comprising from 1 to 100 repeating Si—

O units, provided that said mono-alkyl terminated polydiorganosiloxane is not a hydroxyalkylamine-functional silicone-containing monomer.

14. The silicone hydrogel contact lens of claim 13, further comprising a tan δ

of equal to or less than about 0.3 at a frequency of 1 Hz at 25°

C.

15. The silicone hydrogel contact lens of claim 13, further comprising a O₂Dk greater than about 40 barrer.

16. The silicone hydrogel contact lens of claim 13, 14, or 15, comprising at least 5% wt of said mono-alkyl terminated polydiorganosiloxane.

17. The silicone hydrogel contact lens of claim 13, wherein b=4 to 16, R₅₈ is a monovalent group containing at least one styryl, vinyl, or methacrylate moiety, each R₅₉ is methyl, and R₆₀ is C_3-8 alkyl group.

18. The silicone hydrogel contact lens of claim 13, wherein b=8 to 10, R₅₈ is a methacrylate moiety;

each R₅₉ is methyl;

R₆₀ is a butyl group, and R₆₁ is methyl.

19. The silicone hydrogel contact lens of claim 13, wherein the mono-alkyl terminated polydiorganosiloxane is a monomethacryloxypropyl terminated polydimethylsiloxane.

20. The silicone hydrogel contact lens of claim 13, wherein the center thickness is less than about 85 μ

m.

21. The silicone hydrogel contact lens of claim 13, wherein the center thickness is less than about 100 μ

m and the Young'"'"'s modulus is less than about 100 psi.

22. The silicone contact lens of claim 13, wherein the amount of mono-alkyl terminated polydiorganosiloxane is about 20% wt.

23. The silicone hydrogel contact lens of claim 13, wherein the center thickness is less than 129 μ

m and the Young'"'"'s modulus is less than about 60 psi.

24. The silicone hydrogel contact lens of claim 13, wherein the amount of mono-alkyl terminated polydiorganosiloxane is about 30% wt.