Cationic hydrophilic siloxanyl monomers

• US 20070142583A1
• Filed: 01/27/2006
• Published: 06/21/2007
• Est. Priority Date: 12/21/2005
• 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, Ammon, Daniel, Salamone, Joseph
• Granted Patent: US 7,622,512 B2
• Time in Patent Office: Days
• US Class Current: 526/264
• 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 compromising 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;

methacrylic acids, acrylic acids;

itaconic acid;

itaconic acid esters;

acrylic substituted alcohols;

2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate;

vinyl lactams;

N-vinylpyrrolidone (NVP) N-vinylcaprolactone;

acrylamides;

methacrylamide, N,N-dimethylacrylamide;

methacrylates;

ethylene glycol dimethacrylate, methyl methacrylate, allyl methacrylate;

hydrophilic vinyl carbonates, hydrophilic vinyl carbamate monomers;

hydrophilic oxazolone monomers, 3-methacryloxypropyl tris(trimethylsiloxy)silane, ethylene glycol dimethacrylate (EGDMA), allyl methacrylate (AMA) 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;

extracting the unpolymerized monomers from the polymerized device; and

packaging and sterilizing 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 11 wherein the step of extracting is performed with water.

4. A monomer having the following formula (II) below:

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