Silicon-containing monomers end-capped with polymerizable cationic hydrophilic groups

• US 7,759,408 B2
• Filed: 01/27/2006
• Issued: 07/20/2010
• Est. Priority Date: 12/21/2005
• Status: Expired due to Fees

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: Linhardt, Jeffrey G., Salamone, Joseph C., Schorzman, Derek, Kunzler, Jay
• Primary Examiner(s): Zimmer; Marc S
• Application Number:
  US11/341,209
• Publication Number:
  US 20070142584A1
• Time in Patent Office: 1,635 Days
• Field of Search: None
• US Class Current: 523/107
• CPC Class Codes: A61L 27/18 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C08F 222/102 of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
• 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: C08G 77/388 containing nitrogen
• CPC Class Codes: C08L 101/02 characterised by the presence of specified groups , e.g. terminal or pendant functional groups
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

The present invention relates to polymeric compositions useful in the manufacture of biocompatible medical devices. More particularly, the present invention relates to certain cationic monomers capable of polymerization to form polymeric compositions having desirable physical characteristics useful in the manufacture of ophthalmic devices. Such properties include the ability to extract the polymerized medical devices with water. This avoids the use of organic solvents as is typical in the art. The polymer compositions comprise polymerized silicon-containing monomers end-capped with polymerizable cationic hydrophilic groups.

Claims

1. A monomer of formula (I):

2. The monomer of claim 1 wherein X⁻

is selected from the group consisting of Cl⁻

, Br⁻

, I⁻

, CF₃CO₂⁻

, CH₃CO₂⁻

, HCO₃⁻

, CH₃SO₄⁻

, p-toluenesulfonate, HSO₄⁻

, H₂PO₄⁻

, NO₃⁻

, CH₃CH(OH)CO₂⁻

, SO₄²⁻

, CO₃²⁻

, HPO₄²⁻

and mixtures thereof.

3. The monomer of claim 1 wherein X⁻

is at least a single charged counter ion and is selected from the group consisting of Cl⁻

, Br⁻

, I⁻

, CF₃CO₂⁻

, CH₃CO₂⁻

, HCO₃⁻

, CH₃SO₄⁻

, p-toluenesulfonate, HSO₄⁻

, H₂PO₄⁻

, NO₃⁻

, and CH₃CH(OH)CO₂⁻

and mixtures thereof.

4. The monomer of claim 1 wherein the monomer is selected from the group consisting of monomers having the following formulae:

5. A monomer mix useful for making polymerized biomaterials comprising at least one monomer of claim 1 and at least one second monomer.

6. The monomer mix of claim 5, further comprising in addition to the second monomer a hydrophobic monomer and a hydrophilic monomer.

7. The monomer mix of claim 5 wherein the second monomer is selected from the group consisting of unsaturated carboxylic acids, acrylic substituted alcohols, vinyl lactams, acrylamides, methacrylates, hydrophilic vinyl carbonates, hydrophilic vinyl carbamate monomers, hydrophilic oxazolone monomers, and mixtures thereof.

8. A device comprising the monomer of claim 1 as a polymerized comonomer.

9. The device of claim 8 wherein the device is a contact lens.

10. The device of claim 9 wherein the contact lens is a rigid gas permeable contact lens.

11. The device of claim 9 wherein the contact lens is a soft contact lens.

12. The device of claim 9 wherein the contact lens is a hydrogel contact lens.

13. The device of claim 8 wherein the device is an intraocular lens.

14. The device of claim 13 wherein the intraocular lens is a phakic intraocular lens.

15. The device of claim 13 wherein the intraocular lens is an aphakic intraocular lens.

16. The device of claim 8 wherein the device is a corneal implant.

17. The device of claim 8 wherein the device is selected from the group consisting of heart valves, intraocular lenses, films, surgical devices, vessel substitutes, intrauterine devices, membranes, diaphragms, surgical implants, blood vessels, artificial ureters, artificial breast tissue, membranes for kidney dialysis machines, membranes for heart/lung machines, catheters, mouth guards, denture liners, ophthalmic devices, and contact lenses.

18. A method of making a device comprising:

providing a monomer mixture comprising the monomer of claim 1 and at least a second monomer;

subjecting the monomer mixture to polymerizing conditions to provide a polymerized device; and

extracting the polymerized device.

19. The method of claim 18 wherein the step of extracting is performed with non-flammable solvents.

20. The method of claim 18 wherein the step of extracting is performed with water.

22. The monomer mix of claim 5 wherein the second monomer is methacryloxypropyl tris(trimethylsiloxy)silane.

23. The monomer mix of claim 22 further comprising 1-vinyl-2 pyrolidone, 2-hydroxyethyl methacrylate and 2,2′

-azobis (2-methylpropionitrile).

24. The monomer mix of claim 23 further comprising N,N-dimethylacrylacide.

25. The monomer mix of claim 23 further comprising 1,3-Propanediol.

26. A device comprising the polymerized monomer mix of claim 24.

27. A device comprising the polymerized monomer mix of claim 25.

28. The monomer mix of claim 5 wherein the second monomer is selected from the group consisting of methacrylic acid, acrylic acid, 2-hydroxyethylmethacrylate, 2-hydroxyethylacrylate, N-vinylpyrrolidone, N-vinylcaprolactone, methacrylamide, N,N-dimethylacrylamide, ethylene glycol dimethylacrylate, methyl methacrylate, allyl methacrylate, methacryloxypropyltris(trimethylsiloxy)silane and mixtures thereof.

29. The method of claim 18 further comprising the step of packaging and sterilizing the polymerized device.

21. A silicon containing monomer end-capped with free radical polymerizable ethylenically unsaturated cationic hydrophilic groups.

30. A biomedical device that is a polymerization product of a monomer mixture comprising the silicon containing monomer of claim 21.

31. The biomedical device of claim 30, wherein the monomer mixture further comprises a hydrophobic monomer, a hydrophilic monomer or both.

32. The biomedical device of claim 30, wherein the monomer mixture further comprises a second monomer selected from the group consisting of unsaturated carboxylic acids, acrylic substituted alcohols, vinyl lactams, acrylamides, methacrylates, hydrophilic vinyl carbonates, hydrophilic vinyl carbamate monomers, hydrophilic oxazolone monomers, and mixtures thereof.

33. The biomedical device of claim 30, wherein the device is a contact lens.

34. The biomedical device of claim 33, wherein the contact lens is a rigid gas permeable contact lens.

35. The biomedical device of claim 33, wherein the contact lens is a soft contact lens.

36. The biomedical device of claim 30, wherein the device is an intraocular lens.

37. The biomedical device of claim 30, wherein the device is a corneal implant.