Hydrophilic macromonomers having alpha,beta-conjugated carboxylic terminal group and medical devices incorporating same

• US 20080004410A1
• Filed: 06/30/2006
• Published: 01/03/2008
• Est. Priority Date: 06/30/2006
• Status: Abandoned Application

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: Lai, Yu-Chin, Lang, Weihong
• Application Number:
  US11/479,209
• Publication Number:
  US 20080004410A1
• Time in Patent Office: Days
• US Class Current: 526/264
• CPC Class Codes: C08F 290/06 Polymers provided for in subclass C08G
• CPC Class Codes: C08F 290/061 Polyesters; Polycarbonates
• CPC Class Codes: C08F 290/068 Polysiloxanes
• CPC Class Codes: C08J 2433/00 Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
• CPC Class Codes: C08J 7/0427 with only one layer of a composition containing a polymer binder with more layers C08J7/042
• CPC Class Codes: C08J 7/056 Forming hydrophilic coatings
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

A macromonomer comprises an α,β-conjugated terminal carboxylic group and a plurality of hydrophilic groups. Polymeric materials comprise such a macromonomer are used advantageously to provide a hydrophilic or lubricious (or both) coating on medical devices. Such polymeric materials can comprise units of other hydrophilic monomers.

Claims

1. A macromonomer comprising an α

,β

-conjugated terminal carboxylic group and a plurality of hydrophilic groups.

2. The macromonomer of claim 1, wherein the α

,β

-conjugated terminal carboxylic group comprises maleate, fumarate, or itaconate group.

3. The macromonomer of claim 1, wherein the plurality of hydrophilic groups are selected from the group consisting of N-vinylpyrrolidone, alkylene oxides, glyceryl methacrylate, glyceryl acrylate, dimethyl methacrylamide, dimethyl acrylamide, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, erythritol methacrylate, erythritol acrylate, xylitol methacrylate, xylitol acrylate, sorbitol methacrylate, sorbitol acrylate, derivatives thereof, combinations thereof, or mixtures thereof.

4. The macromonomer of claim 2, wherein the plurality of hydrophilic groups are selected from the group consisting of N-vinylpyrrolidone, alkylene oxides, glyceryl methacrylate, glyceryl acrylate, dimethyl methacrylamide, dimethyl acrylamide, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, erythritol methacrylate, erythritol acrylate, xylitol methacrylate, xylitol acrylate, sorbitol methacrylate, sorbitol acrylate, derivatives thereof, combinations thereof, or mixtures thereof.

5. The macromonomer of claim 1, wherein the plurality of hydrophilic groups comprise N-vinylpyrrolidone.

6. A polymer comprising units of a macromonomer that comprises an α

,β

-conjugated terminal carboxylic group and a plurality of hydrophilic groups.

7. The polymer of claim 6, wherein the α

,β

-conjugated terminal carboxylic group comprises maleate, fumarate, or itaconate group.

8. The polymer of claim 6, wherein the plurality of hydrophilic groups are selected from the group consisting of N-vinylpyrrolidone, polymerizable alkylene oxides, glyceryl methacrylate, glyceryl acrylate, dimethyl methacrylamide, dimethyl acrylamide, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, erythritol methacrylate, erythritol acrylate, xylitol methacrylate, xylitol acrylate, sorbitol methacrylate, sorbitol acrylate, derivatives thereof, combinations thereof, or mixtures thereof.

9. The polymer of claim 8, further comprising units of an additional hydrophilic monomer.

10. The polymer of claim 7, wherein the plurality of hydrophilic groups are selected from the group consisting of N-vinylpyrrolidone, polymerizable alkylene oxides, glyceryl methacrylate, glyceryl acrylate, dimethyl methacrylamide, dimethyl acrylamide, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, erythritol methacrylate, erythritol acrylate, xylitol methacrylate, xylitol acrylate, sorbitol methacrylate, sorbitol acrylate, derivatives thereof, combinations thereof, or mixtures thereof.

11. The polymer of claim 6, wherein the plurality of hydrophilic groups comprise N-vinylpyrrolidone.

12. The polymer of claim 7, wherein the plurality of hydrophilic groups comprise N-vinylpyrrolidone.

13. A medical device comprising a surface coating that comprises units of a macromonomer that comprises an α

,β

-conjugated terminal carboxylic group and a plurality of hydrophilic groups.

14. The medical device of claim 13, wherein the α

,β

-conjugated terminal carboxylic group comprises maleate, fumarate, or itaconate group.

15. The medical device of claim 13, wherein the plurality of hydrophilic groups are selected from the group consisting of N-vinylpyrrolidone, polymerizable alkylene oxides, glyceryl methacrylate, glyceryl acrylate, dimethyl methacrylamide, dimethyl acrylamide, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, erythritol methacrylate, erythritol acrylate, xylitol methacrylate, xylitol acrylate, sorbitol methacrylate, sorbitol acrylate, derivatives thereof, combinations thereof, or mixtures thereof.

16. The medical device of claim 13, wherein the coating further comprises units of an additional hydrophilic monomer.

17. The medical device of claim 13, wherein the plurality of hydrophilic groups comprise N-vinylpyrrolidone.

18. The medical device of claim 14, wherein the plurality of hydrophilic groups are selected from the group consisting of N-vinylpyrrolidone, polymerizable alkylene oxides, glyceryl methacrylate, glyceryl acrylate, dimethyl methacrylamide, dimethyl acrylamide, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, erythritol methacrylate, erythritol acrylate, xylitol methacrylate, xylitol acrylate, sorbitol methacrylate, sorbitol acrylate, derivatives thereof, combinations thereof, or mixtures thereof.

19. The medical device of claim 14, wherein the plurality of hydrophilic groups comprise N-vinylpyrrolidone.

20. The medical device of claim 13, wherein the medical device comprises polysiloxanes.

21. The medical device of claim 20, wherein the medical device comprises hydrogel based on polysiloxanes.

22. The medical device of claim 13, wherein the medical device is a contact lens, intraocular lens, corneal inlay, corneal ring, keratoprothesis, wound dressing, catheter, or implant.

23. A method for providing increased comfort to a user of a medical device, the method comprising contacting the medical device with a coating material that comprises units of a macromonomer that comprises an α

,β

-conjugated terminal carboxylic group and a plurality of hydrophilic groups.

24. The method of claim 23, wherein the α

,β

-conjugated terminal carboxylic group comprises maleate, fumarate, or itaconate group.

25. The method of claim 23, wherein the plurality of hydrophilic groups are selected from the group consisting of N-vinylpyrrolidone, polymerizable alkylene oxides, glyceryl methacrylate, glyceryl acrylate, dimethyl methacrylamide, dimethyl acrylamide, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, erythritol methacrylate, erythritol acrylate, xylitol methacrylate, xylitol acrylate, sorbitol methacrylate, sorbitol acrylate, derivatives thereof, combinations thereof, or mixtures thereof.

26. The method of claim 24, wherein the plurality of hydrophilic groups are selected from the group consisting of N-vinylpyrrolidone, polymerizable alkylene oxides, glyceryl methacrylate, glyceryl acrylate, dimethyl methacrylamide, dimethyl acrylamide, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, erythritol methacrylate, erythritol acrylate, xylitol methacrylate, xylitol acrylate, sorbitol methacrylate, sorbitol acrylate, derivatives thereof, combinations thereof, or mixtures thereof.

27. The method of claim 23, further comprising contacting the medical device with a linking compound in addition to contacting the medical device with the coating material.

28. The method of claim 23, further comprising increasing a population of surface functional groups of the medical device before the step of contacting.

29. The method of claim 28, wherein said increasing the surface functional groups is effected by a method selected from the group consisting of surface implantation of moieties that comprise said functional groups, surface reaction, and combinations thereof.

30. The method of claim 29, wherein the step of increasing the population of the surface functional groups is carried out in a plasma discharge or a corona discharge environment.

31. A method for making a medical device having an increased surface hydrophilicity, or lubricity, or both, the method comprising:

(a) providing the medical device comprising a polymeric material having at least a surface functional group;

(b) providing a coating material that comprises units of a macromonomer that comprises an α

,β

-conjugated terminal carboxylic group and a plurality of hydrophilic groups; and

(c) contacting the medical device with the coating material at a condition sufficient to produce the medical device having an increased surface hydrophilicity, or lubricity, or both.

32. The method of claim 31, wherein the α

,β

-conjugated terminal carboxylic group comprises maleate, fumarate, or itaconate group.

33. The method of claim 31, wherein the plurality of hydrophilic groups are selected from the group consisting of N-vinylpyrrolidone, polymerizable alkylene oxides, glyceryl methacrylate, glyceryl acrylate, dimethyl methacrylamide, dimethyl acrylamide, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, erythritol methacrylate, erythritol acrylate, xylitol methacrylate, xylitol acrylate, sorbitol methacrylate, sorbitol acrylate, derivatives thereof, combinations thereof, or mixtures thereof.

34. The method of claim 32, wherein the plurality of hydrophilic groups are selected from the group consisting of N-vinylpyrrolidone, polymerizable alkylene oxides, glyceryl methacrylate, glyceryl acrylate, dimethyl methacrylamide, dimethyl acrylamide, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, erythritol methacrylate, erythritol acrylate, xylitol methacrylate, xylitol acrylate, sorbitol methacrylate, sorbitol acrylate, derivatives thereof, combinations thereof, or mixtures thereof.

35. The method of claim 31, further comprising contacting the medical device with a linking compound in addition to contacting the medical device with the coating material.

36. The method of claim 31, further comprising increasing a population of said at least a surface functional group before the step of contacting.

37. The method of claim 36, wherein said increasing the population of said at least a surface functional group is effected by a method selected from the group consisting of surface implantation of moieties that comprise said functional groups, surface reaction, and combinations thereof.

38. The method of claim 37, wherein the step of increasing the population of said at least a surface functional group is carried out in a plasma discharge or a corona discharge environment.