Polymeric materials having enhanced ion and water transport property and medical devices comprising same

• US 20070049713A1
• Filed: 08/30/2005
• Published: 03/01/2007
• Est. Priority Date: 08/30/2005
• Status: Active Grant

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: Kunzler, Jay, Salamone, Joseph
• Granted Patent: US 7,390,863 B2
• Time in Patent Office: Days
• US Class Current: 526/279
• CPC Class Codes: C08F 220/282 and containing two or more oxygen atoms
• CPC Class Codes: C08F 230/08 containing silicon
• CPC Class Codes: C08G 77/42 Block-or graft-polymers containing polysiloxane sequences polymerising aliphatic unsaturated monomers on to a polysiloxane C08F283/12

Abstract

A polymeric material having enhanced oxygen permeability and ion and water transport rates comprises units of a first monomer and a second monomer, which comprises linear poly(ethylene oxide), cyclic poly(ethylene oxide), or combinations thereof. Medical devices, such as ophthalmic devices, are made from such polymeric materials.

Claims

1. A polymeric material comprising units of a first monomer and units of a second monomer, wherein the first monomer comprises a slioxane-containing compound, and the second monomer is selected from the group consisting of linear poly(ethylene oxide), cyclic poly(ethylene oxide), and combinations thereof, each having a polymerizable group.

2. The polymeric material of claim 1, wherein the second monomer is a linear poly(ethylene oxide).

3. The polymeric material of claim 1, wherein the second monomer is selected from the group consisting of cyclic poly(ethylene oxide), and combinations of a cyclic poly(ethylene oxide) and linear poly(ethylene oxide).

4. The polymeric material of claim 1, further comprising units of an additional monomer that is selected from the group consisting of hydrophobic monomers, hydrophilic monomers, and combinations thereof.

5. The polymeric material of claim 1, wherein the cyclic poly(ethylene oxide) comprises a crown ether having from 4 to, and including, 10 oxygen atoms.

6. The polymeric material of claim 5, wherein a number of oxygen atoms of the crown ether is in a range from 4 to, and including, 8.

7. The polymeric material of claim 5, wherein one or more oxygen atoms are replaced by an atom selected from the group consisting of nitrogen, sulfur, phosphorus, and combinations thereof.

8. The polymeric material of claim 1, wherein the polymerizable group is selected from the group consisting of vinyl, allyl, acryloyl, acryloyloxy, methacryloyl, methacryloyloxy, epoxide, isocyanate, isothiocyanate, amino, hydroxyl, alkoxy, mercapto, anhydride, carboxylic, fumaryl, styryl, itaconyl, maleimido, methacrylamido, acrylamido, and combinations thereof.

9. The polymeric material of claim 1, wherein the polymerizable group is selected from the group consisting of vinyl, allyl, acryloyl, acryloyloxy, methacryloyl, methacryloyloxy, epoxide, and combinations thereof.

10. The polymeric material of claim 1, wherein the siloxane-containing compound is a polysiloxanylalkyl(meth)acrylic monomer represented by Formula VII

12. The polymeric material of claim 1, wherein the siloxane-containing compound is selected from the group consisting of silicone-containing vinyl carbonate, silicone-containing vinyl carbamate, and combinations thereof.

11. The polymeric material of claim 11, wherein the polysiloxanylalkyl(meth)acrylic monomer is 3-methacryloyloxypropyltris(trimethylsiloxy)silane.

13. A polymeric material comprising units of a first monomer and units of a second monomer, wherein the second monomer is selected from the group consisting of linear poly(ethylene oxide), cyclic poly(ethylene oxide), and combinations thereof, each having a polymerizable group;

the first monomer is a siloxane-containing compound;

the polymerizable group is selected from the group consisting of vinyl, allyl, acryloyl, acryloyloxy, methacryloyl, methacryloyloxy, epoxide, isocyanate, isothiocyanate, amino, hydroxyl, alkoxy, mercapto, anhydride, carboxylic, fumaryl, styryl, itaconyl, maleimido, methacrylamido, acrylamido, and combinations thereof; and

the cyclic poly(ethylene oxide) has a number of oxygen atoms in a range from 4 to, and including, 10.

14. The polymeric material of claim 13, wherein the second monomer is a cyclic poly(ethylene oxide) having a number of oxygen atoms in a range from 4 to, and including, 10.

15. The polymeric material of claim 13, wherein the polymeric material is a silicone hydrogel.

16. The polymeric material of claim 13, wherein the polymeric material further comprises units of a hydrophilic monomer selected from the group consisting of 2-hydroxyethyl methacrylate (“

HEMA”

), 2-hydroxyethyl acrylate (“

HEA”

), 2-(2-ethoxyethoxy)ethyl(meth)acrylate, glyceryl(meth)acrylate, polyethylene glycol(meth)acrylate, tetrahydrofurfuryl(meth)acrylate, (meth)acrylamide, N,N′

-dimethylmethacrylamide, N,N′

-dimethylacrylamide, N-vinyl lactams, N-vinyl acetamide, tetraethylene glycol(meth)acrylate, triethylene glycol(meth)acrylate, tripropylene glycol(meth)acrylate, ethoxylated bisphenol-A (meth)acrylate, pentaerythritol(meth)acrylate, pentaerythritol(meth)acrylate, ditrimethylolpropane(meth)acrylate, ethoxylated trimethylolpropane(meth)acrylate, dipentaerythritol(meth)acrylate, alkoxylated glyceryl(meth)acrylate, vinyl carbonate, vinyl carbamate, and combinations thereof.

17. A medical device comprising a polymeric material that comprises units of a first monomer and units of a second monomer, wherein the second monomer is selected from the group consisting of linear poly(ethylene oxide), cyclic poly(ethylene oxide), and combinations thereof, each having a polymerizable group.

18. The medical device of claim 17, wherein the first monomer is a siloxane-containing compound.

19. The medical device of claim 17, wherein the second monomer is a linear poly(ethylene oxide).

20. The medical device of claim 17, wherein the second monomer is selected from the group consisting of cyclic poly(ethylene oxide), and combinations of a cyclic poly(ethylene oxide) and linear poly(ethylene oxide).

21. The medical device of claim 20, wherein the cyclic poly(ethylene oxide) is a crown ether having a number of oxygen atoms in a range from 4 to, and including, 10.

22. The medical device of claim 21, wherein the first monomer is a siloxane-containing compound.

23. The medical device of claim 22, wherein the first monomer is selected from the group consisting of polysiloxanylalkyl(meth)acrylic monomer, silicone-containing vinyl carbonate, silicone-containing vinyl carbamate, and combinations thereof.

24. The medical device of claim 17, wherein the polymeric material further comprises a material selected from the group consisting of UV absorbers, strengthening agents, crosslinking agents, and combinations thereof.

25. The medical device of claim 17, wherein the medical device is selected from the group consisting of contact lenses, corneal inlays, keratoprotheses, and intraocular lenses.

26. The medical device of claim 25, wherein the medical device has an oxygen permeability greater than about 60 barrers, and ion and water transport rates greater than a medical device that comprises a material that is free of linear or cyclic poly(ethylene oxide).

27. A method of making a polymeric material, the method comprising polymerizing a composition that comprises a first monomer and a second monomer, which is selected from the group consisting of polymerizable linear poly(ethylene oxide), polymerizable cyclic poly(ethylene oxide), and combinations thereof, wherein the first monomer is a siloxane-containing compound.

28. The method of claim 27, wherein the second monomer is a cyclic poly(ethylene oxide).

29. The method of claim 27, wherein the step of polymerizing is carried out under thermal polymerization or photopolymerization conditions.

30. A method of making a polymeric material, the method comprising:

(a) preparing a first prepolymer having units of a first monomer;

(b) preparing a second prepolymer having units of a second monomer; and

(c) polymerizing the first prepolymer with the second prepolymer to produce the polymeric material, wherein the first and second prepolymers have polymerizable terminals, and the second monomer is selected from the group consisting of polymerizable linear poly(ethylene oxide), polymerizable cyclic poly(ethylene oxide), and combinations thereof.

31. The method of claim 30, wherein the first monomer is a siloxane-containing compound and the second monomer is a cyclic poly(ethylene oxide).

32. The method of claim 30, wherein each of the steps (a), (b), and (c) is carried out under thermal polymerization or photopolymerization conditions.

33. A method of making a medical device, the method comprising:

(a) disposing in a mold a composition comprising a first monomer and a second monomer that is selected from polymerizable linear poly(ethylene oxide), cyclic poly(ethylene oxide), and combinations thereof, the mold having a cavity having a shape of the medical device; and

(b) polymerizing the composition to form the medical device.

34. The method of claim 33, wherein the first monomer comprises a siloxane-containing compound, and the second monomer comprises a material selected from the group consisting of cyclic poly(ethylene oxide) and combinations of linear and cyclic poly(ethylene oxide).

35. A method of making a medical device the method comprising:

(a) forming a solid block of a polymeric material comprising units of a first monomer and a second monomer that is selected from the group consisting of polymerizable linear poly(ethylene oxide), cyclic poly(ethylene oxide), and combinations thereof; and

(b) shaping the block to form the medical device.

36. The method of claim 35, wherein the step of shaping comprises:

(a) cutting the block into wafers; and

(b) machining or lathing the wafer to form of the medical device.

37. The method of claim 35, wherein the first monomer comprises a siloxane-containing compound, and the second monomer is selected from the group consisting of cyclic poly(ethylene oxide and combinations of linear and cyclic poly(ethylene oxide).