Siloxane prepolymer containing pendant and end-capping cationic and polymerizable groups

• US 7,528,208 B2
• Filed: 11/30/2006
• Issued: 05/05/2009
• Est. Priority Date: 01/06/2006
• Status: Expired due to Fees

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: Kunzler, Jay F., Salamone, Joseph C., Schorzman, Derek A.
• Primary Examiner(s): Price; Elvis O
• Application Number:
  US11/565,151
• Publication Number:
  US 20070160649A1
• Time in Patent Office: 887 Days
• Field of Search: 528/28, 528/33, 528/24, 528/26, 528/35, 528/27, 528/37, 528/32, 528/42, 526/279
• US Class Current: 528/28
• CPC Class Codes: C08G 77/388 containing nitrogen
• CPC Class Codes: C08G 77/452 containing nitrogen-containing sequences
• 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 random copolymers 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 siloxane prepolymer containing pendant and end-capping cationic and polymerizable groups.

Claims

1. A cationic random copolymer of formula (I):

2. The cationic random copolymer 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 cationic random copolymer 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. A monomer mix useful for making polymerized biomaterials comprising at least one cationic random copolymer of claim 1 and at least a second monomer.

5. The monomer mix of claim 4, further comprising in addition to the second monomer a hydrophobic monomer and a hydrophilic monomer.

6. The monomer mix of claim 4 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.

7. A device comprising the cationic random copolymer of claim 1 as a polymerized comonomer.

8. The device of claim 7 wherein the device is a contact lens.

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

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

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

12. The device of claim 7 wherein the device is an intraocular lens.

13. The device of claim 12 wherein the intraocular lens is a phakic intraocular lens.

14. The device of claim 12 wherein the intraocular lens is an aphakic intraocular lens.

15. The device of claim 7 wherein the device is a corneal implant.

16. The device of claim 7 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.

17. A method of making a device comprising:

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

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

extracting the polymerized device.

18. The method of claim 17 wherein the step of extracting is performed with non-flammable solvents.

19. The method of claim 18 wherein the non-flammable solvent is water.

20. The monomer mix of claim 4 wherein the second monomer is selected from the group consisting of methacrylic acid, acrylic acid, 2-hydroxyethyl methacrylate, 2-hydroxyethylacrylate, N-vinyl pyrrolidone, N-vinyl caprolactone, methacrylamide, N,N-dimethylacrylamide, ethylene glycol dimethacrylate, methyl methacrylate, allyl methacrylate, 3-methacryloxypropyl tris(trimethylsiloxy)silane and mixtures thereof.

21. The method of claim 17 further comprising the step of packaging and sterilizing the polymerized device.

22. The cationic random copolymer of claim 1, wherein at least one R1 is a radical of Formula IV.