Cationic hydrophilic siloxanyl monomers

• US 7,622,512 B2
• Filed: 01/27/2006
• Issued: 11/24/2009
• 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: Ammon, Daniel, Linhardt, Jeffrey G., Salamone, Joseph C., Schorzman, Derek, Kunzler, Jay
• Primary Examiner(s): Zimmer; Marc S
• Application Number:
  US11/341,208
• Publication Number:
  US 20070142583A1
• Time in Patent Office: 1,397 Days
• Field of Search: None
• US Class Current: 523/107
• CPC Class Codes: C08F 226/10 N-Vinyl-pyrrolidone
• CPC Class Codes: C08F 230/08 containing silicon

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 polymeric compositions comprise polymerized cationic hydrophilic siloxanyl monomers.

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⁻

.

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

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

8. The monomer mix of claim 6 wherein the second monomer is selected from the group consisting of unsaturated carboxylic acids, itaconic acid esters, acrylic substituted alcohols, vinyl lactams, acrylamides, methacrylates, hydrophilic vinyl carbonates, hydrophilic vinyl carbamate monomers, hydrophilic oxazolone monomers, and mixtures thereof.

9. A biomedical device comprising a polymerized monomer mixture of claim 6.

10. A method of making a biomedical 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 unpolymerized monomers from the polymerized device.

11. The method of claim 10 wherein the step of extracting is performed with non-flammable solvents.

12. The method of claim 10 wherein the step of extracting is performed with water.

13. The method of claim 10 further comprising the step of packaging and sterilizing the polymerized device.

14. The monomer of claim 1 wherein each R1 is a trimethylsiloxanyl group.

15. The monomer mixture of claim 6 wherein the second monomer is selected from the group consisting of methacrylic acid, acrylic acid, itaconic acid, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, N-vinylpyrrolidone (NVP), N-vinylcaprolactone, methacrylamide, N,N-dimethylacrylamide, methyl methacrylate, 3 -methacryloxypropyl tris(trimethylsiloxy)silane, ethylene glycol dimethacrylate (EGDMA), allyl methacrylate (AMA) and mixtures thereof.

16. The biomedical device of claim 9 which is a contact lens.

17. The biomedical device of claim 16 wherein the contact lens is a rigid gas permeable contact lens, a soft contact lens or a hydrogel contact lens.

18. The biomedical device of claim 9 which is an intraocular lens.

19. The biomedical device of claim 18 wherein the intraocular lens is a phakic intraocular lens or an aphakic intraocular lens.

20. The biomedical device of claim 9 which is a corneal implant.

4. A monomer of formula (II):

5. A monomer selected from the group consisting of the following formulae: