Silicon-containing monomers end-capped with polymerizable cationic hydrophilic groups

• US 20070142584A1
• 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, Salamone, Joseph
• Granted Patent: US 7,759,408 B2
• Time in Patent Office: Days
• US Class Current: 526/264
• CPC Class Codes: A61L 27/18 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C08F 222/102 of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
• CPC Class Codes: C08F 290/06 Polymers provided for in subclass C08G
• CPC Class Codes: C08F 290/061 Polyesters; Polycarbonates
• CPC Class Codes: C08F 290/068 Polysiloxanes
• CPC Class Codes: C08G 77/388 containing nitrogen
• CPC Class Codes: C08L 101/02 characterised by the presence of specified groups , e.g. terminal or pendant functional groups
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

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 polymer compositions comprise polymerized silicon-containing monomers end-capped with polymerizable cationic hydrophilic groups.

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 is selected from the group consisting of monomers having the following formulae:

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 compromising 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;

metacrylamide, N,N-dimethylacrylamide;

methacrylates;

ethylene glycol dimethacrylate, methyl methacrylate, allyl methacrylate;

hydrophilic vinyl carbonates, hydrophilic vinyl carbamate monomers;

hydrophilic oxazolone monomers, methacryloxypropyl 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.

22. The monomer mix of claim 5 wherein the second monomer is methacryloxypropyl tris(trimethylsiloxy)silane.

23. The monomer mix of claim 22 further comprising 1-vinyl-2 pyrrolidone, 2-hydroxyethyl methacrylate and 2,2′

-azobis (2-methylpropionitrile).

24. The monomer mix of claim 23 further comprising N-N-dimethylacrylamide

25. The monomer mix of claim 23 further comprising 1,3-Propanediol.

26. A device comprising the polymerized monomer mix of claim 24.

27. A device comprising the polymerized monomer mix of claim 25.

21. A silicon containing monomer end-capped with ethylenically unsaturated cationic hydrophilic groups.