Cationic end-capped siloxane prepolymer for reduced cross-link density

• US 20070242215A1
• Filed: 04/13/2006
• Published: 10/18/2007
• Est. Priority Date: 04/13/2006
• Status: Active Grant

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: Schorzman, Derek, Kunzler, Jay
• Granted Patent: US 7,960,447 B2
• Time in Patent Office: Days
• US Class Current: 351/160.R
• CPC Class Codes: C07F 7/0838 Compounds with one or more Si-O-Si sequences compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21
• CPC Class Codes: C08F 230/08 containing silicon
• 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 hydrophilic dicationic siloxane prepolymers with one polymerizable vinyl moiety instead of two polymerizable vinyl moieties, resulting in contact lenses and/or biomedical devices with reduced cross-link density and modulus without detracting from other properties.

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 has a structure selected from the group consisting of

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;

methacrylic acids, acrylic acids;

acrylic substituted alcohols;

2-hydroxyethylmethacrylate, 2-hydroxyethylacrylate;

vinyl lactams;

N-vinyl pyrrolidone (NVP) N-vinyl caprolactone;

acrylamides;

methacrylamide, N,N-dimethylacrylamide;

methacrylates;

ethylene glycol dimethacrylate, methyl methacrylate, allyl methacrylate;

hydrophilic vinyl carbonates, hydrophilic vinyl carbamate monomers;

hydrophilic oxazolone monomers, 3-methacryloyloxypropyl tris(trimethylsiloxy)silane, ethylene glycol dimethacrylate (EGDMA), allyl methacrylate (AMA) 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 8 wherein the contact lens is a rigid gas permeable contact lens.

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

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

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

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

15. The device of claim 13 wherein the 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;

extracting the polymerized device; and

packaging and sterilizing 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 extraction solvent is water.

21. A silicon containing monomer containing an ethylenically unsaturated group and at least two cationic hydrophilic groups.

22. The silicon containing monomer of claim 21 wherein the at least two cationic hydrophilic groups are ammonium containing groups.

23. The silicon containing monomer of claim 22 having at least one counter ion 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.