Silicone hydrogel lenses with water-rich surfaces

• US 8,939,577 B2
• Filed: 05/22/2013
• Issued: 01/27/2015
• Est. Priority Date: 07/30/2010
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Qiu, Yongxing, Pruitt, John Dallas, Thekveli, Sibichen J., Tucker, Robert Carey, Nelson, Jared
• Primary Examiner(s): GREECE, JAMES R
• Application Number:
  US13/900,136
• Publication Number:
  US 20130250234A1
• Time in Patent Office: 615 Days
• Field of Search: 351/159.33, 351/159.01, 351/159.02, 526/930, 521/905
• US Class Current: 351/159.33
• CPC Class Codes: B29D 11/00048 composed of parts with dissimilar composition B29D11/00057 takes precedence
• CPC Class Codes: B29D 11/00067 Hydrating contact lenses
• CPC Class Codes: B29D 11/00865 Applying coatings; tinting; colouring printing, marking or copying processes B41M; identification in general G09F3/00; producing decorative effects in general B44C; positioning or marking of lenses B24B13/0055
• CPC Class Codes: C08G 77/388 containing nitrogen
• CPC Class Codes: C08J 2383/04 Polysiloxanes
• CPC Class Codes: C08J 2383/08 containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
• CPC Class Codes: C08J 2433/02 Homopolymers or copolymers of acids; Metal or ammonium salts thereof
• CPC Class Codes: C08J 2433/26 Homopolymers or copolymers of acrylamide or methacrylamide
• CPC Class Codes: C08J 2487/00 Characterised by the use of unspecified macromolecular compounds, obtained otherwise than by polymerisation reactions only involving unsaturated carbon-to-carbon bonds
• CPC Class Codes: C08J 5/00 Manufacture of articles or shaped materials containing macromolecular substances manufacture of semi-permeable membranes B01D67/00 - B01D71/00
• CPC Class Codes: C08J 7/042 with two or more layers, where at least one layer of a composition contains a polymer binder
• CPC Class Codes: C08L 101/14 the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
• 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 133/14 of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
• CPC Class Codes: C09D 133/26 Homopolymers or copolymers of acrylamide or methacrylamide
• CPC Class Codes: C09D 171/02 Polyalkylene oxides
• CPC Class Codes: C09D 177/06 Polyamides derived from polyamines and polycarboxylic acids C09D177/10 takes precedence
• CPC Class Codes: C09D 5/1637 Macromolecular compounds
• CPC Class Codes: C09D 5/1681 Antifouling coatings characterised by surface structure, e.g. for roughness effect giving superhydrophobic coatings or Lotus effect
• CPC Class Codes: G02B 1/043 : Contact lenses
• CPC Class Codes: G02B 1/10 : Optical coatings produced by application to, or surface treatment of, optical elements G02B1/08 takes precedence
• CPC Class Codes: G02B 1/18 : Coatings for keeping optical surfaces clean, e.g. hydrophobic or photo-catalytic films G02B1/16 takes precedence
• CPC Class Codes: G02C 2202/06 : Special ophthalmologic or optometric aspects
• CPC Class Codes: G02C 2202/16 : Laminated or compound 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 is related to a hydrated silicone hydrogel contact lens having a layered structural configuration: a lower water content silicone hydrogel core (or bulk material) completely covered with a layer of a higher water content hydrogel totally or substantially free of silicone. A hydrated silicone hydrogel contact lens of the invention possesses high oxygen permeability for maintaining the corneal health and a soft, water-rich, lubricious surface for wearing comfort.

Claims

1. A silicone hydrogel contact lens having a layered structural configuration and a water content gradient from inside to outside of the silicone hydrogel contact lens, comprising:

a silicone hydrogel core (or bulk material) completely covered with an outer (surface) hydrogel layer having a thickness of at least about 0.1 μ

m as measured with atomic force microscopy across a cross section from the posterior surface to the anterior surface of the silicone hydrogel contact lens in fully hydrated state,

wherein the outer hydrogel layer is substantially free of silicone, and

wherein the water content of the outer hydrogel layer is at least about 1.2 folds (or about 120%) of the water content (designated as WC_SiHy) of the silicone hydrogel bulk material when being fully hydrated.

2. The silicone hydrogel contact lens of claim 1, wherein the outer hydrogel layer comprises two outer layers which merge at the peripheral edge of the silicone hydrogel contact lens, wherein the two outer layers are substantially identical to each other.

3. The silicone hydrogel contact lens of claim 2, wherein the outer (surface) hydrogel layer has:

a thickness of from about 0.1 μ

m to about 20 μ

m as measured with atomic force microscopy across a cross section from the posterior surface to the anterior surface of the silicone hydrogel contact lens in fully hydrated state;

a surface silicon atomic percentage of about 5% or less of total elemental percentage as measured by XPS analysis of the silicone hydrogel contact lens in dried state;

a water content that is at least about 1.3 folds (or about 130%) of the water content of the silicone hydrogel bulk material when being fully hydrated;

a reduced surface modulus of at least about 20% relative to the silicone hydrogel bulk material when being fully hydrated;

or a combination thereof.

4. The silicone hydrogel contact lens of claim 2, wherein the outer (surface) hydrogel layer has:

a thickness of from about 0.25 μ

m to about 15 μ

m as measured with atomic force microscopy across a cross section from the posterior surface to the anterior surface of the silicone hydrogel contact lens in fully hydrated state;

a surface silicon atomic percentage of about 4% or less of total elemental percentage as measured by XPS analysis of the silicone hydrogel contact lens in dried state;

a water content that is at least about 1.4 folds (or about 140%) of the water content of the silicone hydrogel bulk material when being fully hydrated;

a reduced surface modulus of at least about 25% relative to the silicone hydrogel bulk material when being fully hydrated;

or a combination thereof.

5. The silicone hydrogel contact lens of claim 2, wherein the outer (surface) hydrogel layer has:

a thickness of from about 0.5 μ

m to about 12.5 μ

m as measured with atomic force microscopy across a cross section from the posterior surface to the anterior surface of the silicone hydrogel contact lens in fully hydrated state;

a surface silicon atomic percentage of about 3% or less of total elemental percentage as measured by XPS analysis of the silicone hydrogel contact lens in dried state;

a water content that is at least about 1.5 folds (or about 150%) of the water content of the silicone hydrogel bulk material when being fully hydrated;

a reduced surface modulus of at least about 30% relative to the silicone hydrogel bulk material when being fully hydrated;

or a combination thereof.

6. The silicone hydrogel contact lens of claim 3, wherein the outer (surface) hydrogel layer has:

a thickness of from about 1 μ

m to about 10 μ

m as measured with atomic force microscopy across a cross section from the posterior surface to the anterior surface of the silicone hydrogel contact lens in fully hydrated state;

a water content that is at least about 2 folds (or about 200%) of the water content of the silicone hydrogel bulk material when being fully hydrated;

a reduced surface modulus of at least about 35% relative to the silicone hydrogel bulk material when being fully hydrated;

or a combination thereof.

7. The silicone hydrogel contact lens of claim 4 , wherein the outer (surface) hydrogel layer has:

a thickness of from about 1 μ

m to about 10 μ

m as measured with atomic force microscopy across a cross section from the posterior surface to the anterior surface of the silicone hydrogel contact lens in fully hydrated state;

a water content that is at least about 2 folds (or about 200%) of the water content of the silicone hydrogel bulk material when being fully hydrated;

a reduced surface modulus of at least about 40% relative to the silicone hydrogel bulk material when being fully hydrated;

or a combination thereof.

8. The silicone hydrogel contact lens of claim 5, wherein the outer (surface) hydrogel layer has:

a thickness of from about 1 μ

m to about 10 μ

m as measured with atomic force microscopy across a cross section from the posterior surface to the anterior surface of the silicone hydrogel contact lens in fully hydrated state;

a water content that is at least about 2 folds (or about 200%) of the water content of the silicone hydrogel bulk material when being fully hydrated;

or a combination thereof.

9. The silicone hydrogel contact lens of claim 2, wherein the water content of the outer hydrogel layer is at least about 2 folds (or about 200%) of the water content of the silicone hydrogel bulk material when being fully hydrated.

10. The silicone hydrogel contact lens of claim 3, wherein the water content of the outer hydrogel layer is at least about 2 folds (or about 200%) of the water content of the silicone hydrogel bulk material when being fully hydrated.

11. The silicone hydrogel contact lens of claim 4, wherein the water content of the outer hydrogel layer is at least about 2 folds (or about 200%) of the water content of the silicone hydrogel bulk material when being fully hydrated.

12. The silicone hydrogel contact lens of claim 5, wherein the water content of the outer hydrogel layer is at least about 2 folds (or about 200%) of the water content of the silicone hydrogel bulk material when being fully hydrated.

13. The silicone hydrogel contact lens of claim 6, wherein the water content of the outer hydrogel layer is at least about 2 folds (or about 200%) of the water content of the silicone hydrogel bulk material when being fully hydrated.

14. The silicone hydrogel contact lens of claim 2, wherein the water content of the outer hydrogel layer is greater than 75% when being fully hydrated.

15. The silicone hydrogel contact lens of claim 2, wherein when being fully hydrated the silicone hydrogel bulk material has:

a water content (designated as WC_siHy) of from about 10% to about 70% by weight by weight;

a bulk elastic modulus of from about 0.3 MPa to about 1.8 MPa;

or a combination thereof.

16. The silicone hydrogel contact lens of claim 10, wherein when being fully hydrated the silicone hydrogel bulk material has a water content (designated as WC_siHy) of from about 10% to about 60% by weight.

17. The silicone hydrogel contact lens of claim 11, wherein when being fully hydrated the silicone hydrogel bulk material has:

a water content (designated as WC_siHy) of from about 15% to about 55% by weight.

18. The silicone hydrogel contact lens of claim 12, wherein when being fully hydrated the silicone hydrogel bulk material has:

a water content (designated as WC_siHy) of from about 15% to about 50% by weight.

19. The silicone hydrogel contact lens of claim 2, wherein the silicone hydrogel contact lens has at least one property selected from the group consisting of:

(a) an oxygen transmissibility of at least about 40 barrers/mm when being fully hydrated;

(b) a surface hydrophilicity characterized by having a water breakup time of at least about 10 seconds when being fully hydrated;

(c) a surface wettability characterized by having an averaged water contact angle of about 90 degrees or less when being fully hydrated;

(d) a surface lubricity characterized by having a critical coefficient of friction (designated as CCOF) of about 0.046 or less when being fully hydrated; and

(e) combinations thereof.

20. The silicone hydrogel contact lens of claim 3, wherein the silicone hydrogel contact lens has at least one property selected from the group consisting of:

(a) an oxygen transmissibility of at least about 60 barrers/mm when being fully hydrated;

(b) a surface hydrophilicity characterized by having a water breakup time of at least about 10 seconds when being fully hydrated;

(c) a surface wettability characterized by having an averaged water contact angle of about 80 degrees or less when being fully hydrated;

(d) a surface lubricity characterized by having a critical coefficient of friction (designated as CCOF) of about 0.043 or less when being fully hydrated; and

(e) combinations thereof.

21. The silicone hydrogel contact lens of claim 4, wherein the silicone hydrogel contact lens has at least one property selected from the group consisting of:

(a) an oxygen transmissibility of at least about 80 barrers/mm when being fully hydrated;

(b) a surface hydrophilicity characterized by having a water breakup time of at least about 10 seconds when being fully hydrated;

(c) a surface wettability characterized by having an averaged water contact angle of about 80 degrees or less when being fully hydrated;

(d) a surface lubricity characterized by having a critical coefficient of friction (designated as CCOF) of about 0.043 or less when being fully hydrated; and

(e) combinations thereof.

22. The silicone hydrogel contact lens of claim 5, wherein the silicone hydrogel contact lens has at least one property selected from the group consisting of:

(a) an oxygen transmissibility of at least about 40 barrers/mm when being fully hydrated;

(b) a surface hydrophilicity characterized by having a water breakup time of at least about 10 seconds when being fully hydrated;

(c) a surface wettability characterized by having an averaged water contact angle of about 80 degrees or less when being fully hydrated;

(d) a surface lubricity characterized by having a critical coefficient of friction (designated as CCOF) of about 0.043 or less when being fully hydrated; and

(e) combinations thereof.

23. The silicone hydrogel contact lens of claim 6, wherein the silicone hydrogel contact lens has at least one property selected from the group consisting of:

(a) an oxygen transmissibility of at least about 60 barrers/mm when being fully hydrated;

(b) a surface hydrophilicity characterized by having a water breakup time of at least about 10 seconds when being fully hydrated;

(c) a surface wettability characterized by having an averaged water contact angle of about 80 degrees or less when being fully hydrated;

(d) a surface lubricity characterized by having a critical coefficient of friction (designated as CCOF) of about 0.043 or less when being fully hydrated; and

(e) combinations thereof.

24. The silicone hydrogel contact lens of claim 2, wherein the outer hydrogel layer has a water content that is higher than WC_SiHy, as characterized either (a) by having a water-swelling ratio (WSR) of at least about 100% if WC_SiHy≦

45% or (b) by having a water-swelling ratio of at least about

25. The silicone hydrogel contact lens of claim 3, wherein the outer hydrogel layer has a water content that is higher than WC_SiHy, as characterized either (a) by having a water-swelling ratio (WSR) of at least about 100% if WC_SiHy≦

45% or (b) by having a water-swelling ratio of at least about

26. The silicone hydrogel contact lens of claim 4, wherein the outer hydrogel layer has a water content that is higher than WC_SiHy, as characterized either (a) by having a water-swelling ratio (WSR) of at least about 150% if WC_SiHy≦

45% or (b) by having a water-swelling ratio of at least about

27. The silicone hydrogel contact lens of claim 5, wherein the outer hydrogel layer has a water content that is higher than WC_SiHy, as characterized either (a) by having a water-swelling ratio (WSR) of at least about 150% if WC_SiHy≦

45% or (b) by having a water-swelling ratio of at least about

28. The silicone hydrogel contact lens of claim 15, wherein the outer hydrogel layer has a water content that is higher than WC_SiHy, as characterized either (a) by having a water-swelling ratio (WSR) of at least about 150% if WC_SiHy≦

45% or (b) by having a water-swelling ratio of at least about

29. The silicone hydrogel contact lens of claim 19, wherein the outer hydrogel layer has a water content that is higher than WC_SiHy, as characterized either (a) by having a water-swelling ratio (WSR) of at least about 150% if WC_SiHy≦

45% or (b) by having a water-swelling ratio of at least about

30. The silicone hydrogel contact lens of claim 22, wherein the outer hydrogel layer has a water content that is higher than WC_SiHy, as characterized either (a) by having a water-swelling ratio (WSR) of at least about 150% if WC_SiHy≦

45% or (b) by having a water-swelling ratio of at least about