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

• US 7,960,447 B2
• Filed: 04/13/2006
• Issued: 06/14/2011
• Est. Priority Date: 04/13/2006
• Status: Expired due to Fees

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: Schorzman, Derek, Kunzler, Jay
• Primary Examiner(s): Landau; Sharmila
• Assistant Examiner(s): BREDEFELD, RACHAEL EVA
• Application Number:
  US11/403,393
• Publication Number:
  US 20070242215A1
• Time in Patent Office: 1,888 Days
• Field of Search: None
• US Class Current: 523/107
• 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⁻

, SO₄ ²⁻

, 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 having 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, 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 conical 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.

21. 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-vinyl pyrrolidone (NVP), N-vinyl caprolactone, methacrylamide, N,N-dimethylacrylamide, ethylene glycol dimethacrylate, methyl methacrylate, allyl methacrylate, 3-methacryloyloxypropyl tris(trimethylsiloxy)silane and mixtures thereof.

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