Contact lenses

• US 6,849,671 B2
• Filed: 10/09/2001
• Issued: 02/01/2005
• 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: Steffen, Robert B., Turner, David C., Vanderlaan, Douglas
• Primary Examiner(s): Cain, Edward J.
• Application Number:
  US09/973,645
• Publication Number:
  US 20040209973A1
• Time in Patent Office: 1,211 Days
• Field of Search: 523/106, 523/107
• US Class Current: 523/107
• CPC Class Codes: C08F 230/085 the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
• 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: C08L 83/04 Polysiloxanes
• CPC Class Codes: C09D 133/02 Homopolymers or copolymers of acids; Metal or ammonium salts thereof
• CPC Class Codes: C09D 133/10 Homopolymers or copolymers of methacrylic acid esters
• CPC Class Codes: C09D 133/26 Homopolymers or copolymers of acrylamide or methacrylamide
• 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

The invention provides silicone hydrogel contact lenses that exhibit reduced back surface debris and reduced incidence of superior epithelial arcurate lesions.

Claims

1. A silicone contact lens comprising a center stiffness of about 1 psi·

mm² or less and a lenticular junction stiffness of about 4.4 psi·

mm² or less, wherein the lens exhibits an advancing contact angle of less than about 120 degrees.

2. The contact lens of claim 1, wherein lenticular junction stiffness is about 4 psi·

mm² or less.

3. The lens of claim 1, wherein a center stiffness of about 0.5 psi·

mm² or less and a lenticular junction stiffness of about 4 psi·

mm² or less.

4. The contact lens of claim 1, 2, or 3, wherein the advancing contact angle is less than about 80 degrees.

5. The contact lens of claim 1, 2 or 3, wherein the advancing contact angle is less than about 55 degrees.

6. The lens of claim 4, further comprising an internal wetting agent selected from the group consisting of polyamides, polylactams, polyimides, polylactones, and combinations thereof.

7. The contact lens of claim 4, further comprising the reaction product of a silicone based macromer and a polymerizable mixture comprising Si_8-10 monomethacryloxy terminated polydimethyl siloxane, polydimethylsiloxane other than Si_8-10 monomethacryloxy terminated polydimethyl siloxane, and a hydrophilic monomer.

8. The contact lens of claim 4, further comprising the reaction product of a silicone based macromer Group Transfer Polymerization product and a polymerizable mixture comprising Si_8-10monomethacryloxy terminated polydimethyl siloxane, polydimethylsiloxane other than Si_8-10 monomethacryloxy terminated polydimethyl siloxane, and a hydrophilic monomer.

9. The contact lens of claim 7, wherein the macromer is the product of a reaction mixture comprising the 2-hydroxyethyl methacrylate, methyl methacrylate, methacryloxypropyltris(trimethylsiloxy)silane, and mono-methacryloxypropyl terminated mono-butyl terminated polydimethylsiloxane.

10. The contact lens of claim 8, wherein the macromer is the product of a reaction mixture comprising the 2-hydroxyethyl methacrylate, methyl methacrylate, methacryloxypropyltris(trimethylsiloxy)silane, and mono-methacryloxypropyl terminated mono-butyl terminated polydimethylsiloxane.

11. The contact lens of claim 9, wherein the macromer is the polymerization product of reaction mixture comprising about 19.1 moles of 2-hydroxyethyl methacrylate, about 2.8 moles of methyl methacrylate, about 7.9 moles of methacryloxypropyltris(trimethylsiloxy)silane, and about 3.3 moles of mono-methacryloxypropyl terminated mono-butyl terminated polydimethylsiloxane.

12. The contact lens of claim 10, wherein the macromer is the polymerization product of reaction mixture comprising about 19.1 moles of 2-hydroxyethyl methacrylate, about 2.8 moles of methyl methacrylate, about 7.9 moles of methacryloxypropyltris(trimethylsiloxy)silane, and about 3.3 moles of mono-methacryloxypropyl terminated mono-butyl terminated polydimethylsiloxane.

13. The contact lens of claim 9, wherein the polymerizable mixture comprises Si Si_8-10 monomethacryloxy terminated polydimethyl siloxane;

methacryloxypropyl tris(trimethyl siloxy) silane;

N,N-dimethylacrylamide;

2-hydroxy ethyl methacrylate; and

tetraethyleneglycol dimethacrylate.

14. The contact lens of claim 10, wherein the polymerizable mixture comprises Si_7-9 monomethacryloxy terminated polydimethyl siloxane;

methacryloxypropyl tris(trimethylsiloxy) silane;

N,N-dimethylacrylamide;

2-hydroxyethyl methacrylate; and

tetraethyleneglycol dimethacrylate.

15. The contact lens of claim 13, wherein the macromer is present in an amount of about 10 to about 60 wt percent, the Si_8-10 monomethacryloxy terminated polydimethyl siloxane is present in an amount of about 0 to about 45 wt percent;

the methacryloxypropyl tris(trimethylsiloxy) silane is present in an amount of about 0 to about 40 wt percent;

the N,N-dimethylacrylamide is present in an amount of about 5 to about 40 wt percent;

the 2-hydroxyethyl methacrylate is present in an amount of about 0 to about 10 wt percent; and

the tetraethyleneglycol dimethacrylate is present in an amount of about 0 to about 5 wt percent.

16. The contact lens of claim 14, wherein the macromer is present in an amount of about 10 to about 60 wt percent, the Si_8-10 monomethacryloxy terminated polydimethyl siloxane is present in an amount of about 0 to about 45 wt percent;

the methacryloxypropyl tris(trimethyl siloxy) silane is present in an amount of about 0 to about 40 wt percent;

the N,N-dimethylacrylamide is present in an amount of about 5 to about 40 wt percent;

the 2-hydroxyethyl methacrylate is present in an amount of about 0 to about 10 wt percent; and

the tetraethyleneglycol dimethacrylate is present in an amount of about 0 to about 5 wt percent.

17. The contact lens of claim 13, wherein the macromer is present in an amount of about 15 to about 25 wt percent, the Si_8-10 monomethacryloxy terminated polydimethyl siloxane is present in an amount of about 20 to about 30 wt percent;

the methacryloxypropyl tris(trimethyl siloxy) silane is present in an amount of about 15 to about 25 wt percent;

the N,N-dimethylacrylamide is present in an amount of about 20 to about 30 wt percent;

the 2-hydroxyethyl methacrylate is present in an amount of about 2 to about 7 wt percent; and

the tetraethyleneglycol dimethacrylate is present in an amount of about 0 to about 5 wt percent.

18. The contact lens of claim 14, wherein the macromer is present in an amount of about 15 to about 25 wt percent, the Si_8-10 monomethacryloxy terminated polydimethyl siloxane is present in an amount of about 20 to about 30 wt percent;

the methacryloxypropyl tris(trimethyl siloxy) silane is present in an amount of about 15 to about 25 wt percent;

the N,N-dimethyl acrylamide is present in an amount of about 20 to about 30 wt percent;

the 2-hydroxyethyl methacrylate is present in an amount of about 2 to about 7 wt percent; and

the tetraethyleneglycol dimethacrylate is present in an amount of about 0 to about 5 wt percent.

19. The contact lens of claim 13, wherein the polymerizable mixture further comprises poly(N-vinyl pyrrolidinone).

20. The contact lens of claim 14, wherein the polymerizable mixture further comprises poly(N-vinyl pyrrolidinone).

21. The contact lens of claim 15, wherein the polymerizable mixture further comprises about 0 to about 10 wt percent poly(N-vinyl pyrrolidinone).

22. The contact lens of claim 16, wherein the polymerizable mixture further comprises about 0 to about 10 wt percent poly(N-vinyl pyrrolidinone).

23. The contact lens of claim 17, wherein the polymerizable mixture further comprises about 2 to about 7 wt percent poly(N-vinyl pyrrolidinone).

24. The contact lens of claim 18, wherein the polymerizable mixture further comprises about 2 to about 7 wt percent poly(N-vinyl pyrrolidinone).

25. The contact lens of claim 4, further comprising a coating selected from the group consisting of poly(acrylic acid), poly(methacrylic acid), poly(maleic acid), poly(itaconic acid), poly(acrylamide), poly(dimethacrylamide), block or random copolymers of (meth)acrylic acid, acrylic acid, maleic acid, itaconic acid with any reactive vinyl monomer, carboxymethylated polymers, such as carboxymethylcellulose, dextran, polyvinyl alcohol, polyethylene oxide, poly(2-hydroxy ethyl methacrylate), polysulfonates, polysulfates, polylactam, polyglycolic acid, polyamines, and mixtures thereof.

26. The contact lens of claim 7, further comprising a coating selected from the group consisting of poly(acrylic acid), poly(methacrylic acid), poly(maleic acid), poly(itaconic acid), poly(acrylamide), poly(dimethacrylamide), block or random copolymers of (meth)acrylic acid, acrylic acid, maleic acid, itaconic acid with any reactive vinyl monomer, carboxymethylated polymers, such as carboxymethylcellulose, dextran, polyvinyl alcohol, polyethylene oxide, poly(2-hydroxyethyle methacrylate), polysulfonates, polysulfates, polylactam, polyglycolic acid, polyamines, and mixtures thereof.

27. The contact lens of claim 8, further comprising a coating selected from the group consisting of poly(acrylic acid), poly(methacrylic acid), poly(maleic acid), poly(itaconic acid), poly(acrylamide), poly(dimethacrylamide), block or random copolymers of (meth)acrylic acid, acrylic acid, maleic acid, itaconic acid with any reactive vinyl monomer, carboxymethylated polymers, such as carboxymethylcellulose, dextran, polyvinyl alcohol, polyethylene oxide, poly(2-hydroxyethyl methacrylate), polysulfonates, polysulfates, polylactam, polyglycolic acid, polyamines, and mixtures thereof.

28. The contact lens of claim 26, wherein the coating is poly(acrylic acid), poly(acrylamide), or poly(2-hydroxyethyl methacrylate).

29. The contact lens of claim 27, wherein the coating is poly(acrylic acid), poly(acrylamide), or poly(2-hydroxyethyl methacrylate).

30. The contact lens of claim 9, further comprising a coating selected from the group consisting of poly(acrylic acid), poly(methacrylic acid), poly(maleic acid), poly(itaconic acid), poly(acrylamide), poly(dimethacrylamide), block or random copolymers of (meth)acrylic acid, acrylic acid, maleic acid, itaconic acid with any reactive vinyl monomer, carboxymethylated polymers, such as carboxymethylcellulose, dextran, polyvinyl alcohol, polyethylene oxide, poly(2-hydroxyethyl methacrylate), polysulfonates, polysulfates, polylactam, polyglycolic acid, polyamines, and mixtures thereof.

31. The contact lens of claim 15, further comprising a coating selected from the group consisting of poly(acrylic acid), poly(methacrylic acid), poly(maleic acid), poly(itaconic acid), poly(acrylamide), poly(dimethacrylamide), block or random copolymers of (meth)acrylic acid, acrylic acid, maleic acid, itaconic acid with any reactive vinyl monomer, carboxymethylated polymers, such as carboxymethylcellulose, dextran, polyvinyl alcohol, polyethylene oxide, poly(2-hydroxyethyle methacrylate), polysulfonates, polysulfates, polylactam, polyglycolic acid, polyamines, and mixtures thereof.

32. The contact lens of claim 19, further comprising a coating selected from the group consisting of poly(acrylic acid), poly(methacrylic acid), poly(maleic acid), poly(itaconic acid), poly(acrylamide), poly(dimethacrylamide), block or random copolymers of (meth)acrylic acid, acrylic acid, maleic acid, itaconic acid with any reactive vinyl monomer, carboxymethylated polymers, such as carboxymethylcellulose, dextran, polyvinyl alcohol, polyethylene oxide, poly(2-hydroxyethyle methacrylate), polysulfonates, polysulfates, polylactam, polyglycolic acid, polyamines, and mixtures thereof.

33. A method for significantly reducing SEALs and back-trapped debris in a silicone hydrogel lens, comprising the step of providing a contact lens comprising a center stiffness of about 1 psi·

mm² or less and a lenticular junction stiffness of about 4.4 psi·

mm² or less, wherein the lens exhibits an advancing contact angle of less than about 120 degrees.

34. The method of claim 33, wherein the lens provided comprises a center stiffness less than about 1 psi·

mm² and the lenticular junction stiffness less than about 4 psi·

mm².

35. The method of claim 33, wherein the lens provided comprises a center stiffness less than about 0.5 psi·

mm² and the lenticular junction stiffness less than about 4 psi·

mm².

36. The method of claim 33, 34, or 35 wherein the lens exhibits an the advancing contact angle exhibited of less than about 80 degrees.