SYNTHESIS OF CATIONIC SILOXANE PREPOLYMERS

• US 20080182956A1
• Filed: 01/24/2008
• Published: 07/31/2008
• Est. Priority Date: 01/26/2007
• Status: Active Grant

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: Kunzler, Jay F., Schorzman, Derek A., Nunez, Ivan M., Stanbro, Jason K.
• Granted Patent: US 7,951,897 B2
• Time in Patent Office: Days
• US Class Current: 526/260
• CPC Class Codes: C08G 77/388 containing nitrogen
• CPC Class Codes: C08L 83/08 containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

This application is directed toward an improved method of synthesizing cationic siloxane prepolymers as well as a specific cationic siloxane prepolymer having improved compatibility with monofunctional siloxanyl methacrylate monomers and medical devices containing the cationic siloxane prepolymer.

Claims

1. A method of making a cationic siloxane prepolymer, the method comprising:

reacting a bis-halide polysiloxane with an alkyl functionalized hydroxy secondary amine in a first polar solvent to provide a first reaction product;

reacting the first reaction product with a methacrylating agent in the presence of a acid scavenger in a second polar solvent to provide a second reaction product; and

reacting the second reaction product with a quaternizing agent in a third polar solvent to provide the cationic siloxane prepolymer.

2. The method of claim 1 wherein the bis-halide polysiloxane is selected from the group consisting of bis-bromobutyl polydimethylsiloxane, bis-bromopropyl polydimethylsiloxane, bis-chloropropyl polydimethylsiloxane, and bis-3 -chlorobutyl polydimethylsiloxane.

3. The method of claim 1 wherein the alkyl functionalized hydroxy secondary amine is selected from the group consisting of 2-(methylamino)ethanol, 2-(ethylamino) ethanol, 2-(propylamino) ethanol and 2-(butylamino) ethanol.

4. The method of claim 1 wherein the methacrylating agent is selected from the group consisting of methacryloyl chloride, methacrylic anhydride, 2-isocyanatoethyl methacrylate, itaconic acid and itaconic anhydride.

5. The method of claim 1 wherein the quaternizing agent is selected from the group consisting of iodomethane, iodoethane, 1 -bromobutane, and methyl chloride.

6. The method of claim 1 further comprising the step of isolating the cationic siloxane prepolymer.

7. A monomer having the following formula:

8. A monomer mix useful for making polymerized biomaterials comprising at least one monomer of claim 7 and at least one second monomer.

9. The monomer mix of claim 8, further comprising in addition to the second monomer a hydrophobic monomer and a hydrophilic monomer.

10. The monomer mix of claim 8 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.

11. A device comprising a polymerization product of the monomer mixture of claim 8.

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

13. The device of claim 12 wherein the contact lens is a rigid gas permeable contact lens.

14. The device of claim 12 wherein the contact lens is a soft contact lens.

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

16. The device of claim 11 wherein the device is an intraocular lens.

17. The device of claim 16 wherein the intraocular lens is a phakic intraocular lens.

18. The device of claim 16 wherein the intraocular lens is an aphakic intraocular lens.

19. The device of claim 11 wherein the device is a corneal implant.

20. The device of claim 11 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.

21. A method of making a device comprising:

providing a monomer mixture comprising the monomer of claim 7 and at least a second monomer;

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

extracting the polymerized device.

22. The method of claim 21 wherein the step of extracting is performed with non-flammable solvents.

23. The method of claim 21 wherein the step of extracting is performed with water.

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

25. The monomer mix of claim 8 wherein the second monomer is selected from the group consisting of methacrylic acid, acrylic acid, 2-hydroxyethylmethacrylate, 2-hydroxyethylacrylate, N-vinyl pyrrolidone, N-vinyl caprolactone, methacrylamide, N-N-dimethylacrylamide, ethylene glycol dimethacrylate, methyl methacrylate, allyl methacrylate, methacryloxypropyl tris(trimethylsiloxy)silane and mixtures thereof.