Polymerizable siloxane-quaternary amine copolymers

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.

1 - 20 . (canceled) 
   
   
       21 . A silicon containing monomer end-capped with free radical polymerizable ethylenically unsaturated cationic hydrophilic groups. 
   
   
       22 . The silicone containing monomer of  claim 21 , wherein the free radical polymerizable ethylenically unsaturated cationic hydrophilic groups are terminated with a (meth)acrylate-containing moiety. 
   
   
       23 . The silicone containing monomer of  claim 21 , having one or more cationic silicone-containing units which are endcapped with the free radical polymerizable ethylenically unsaturated cationic hydrophilic groups. 
   
   
       24 . A monomer mixture useful for making polymerized biomaterials comprising at least one monomer of  claim 21  and at least one second monomer. 
   
   
       25 . The monomer mixture of  claim 24 , further comprising in addition to the second monomer a hydrophobic monomer and a hydrophilic monomer. 
   
   
       26 . The monomer mixture of  claim 24 , wherein the second monomer is selected from the group consisting of an unsaturated carboxylic acid, acrylic substituted alcohol, vinyl lactam, acrylamide, methacrylate, hydrophilic vinyl carbonate, hydrophilic vinyl carbamate monomer, hydrophilic oxazolone monomers and mixtures thereof. 
   
   
       27 . The monomer mixture of  claim 24 , wherein the second monomer is selected from the group consisting of methacrylic acid, acrylic acid, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, N-vinyl pyrrolidone, N-vinyl caprolactone, methacrylamide, N,N-dimethylacrylamide, ethylene glycol dimethacrylate, methyl methacrylate, allyl methacrylate, 3-methacryloyloxypropyl tris(trimethylsiloxy)silane and mixtures thereof. 
   
   
       28 . A biomedical device comprising the silicon-containing monomer of  claim 21  as a polymerized comonomer. 
   
   
       29 . A biomedical device comprising a polymerization product of the monomer mixture of  claim 24 . 
   
   
       30 . A biomedical device comprising a polymerization product of the monomer mixture of  claim 26 . 
   
   
       31 . The biomedical device of  claim 28 , wherein the device is a contact lens. 
   
   
       32 . The biomedical device of  claim 31 , wherein the contact lens is a rigid gas permeable contact lens. 
   
   
       33 . The biomedical device of  claim 31 , wherein the contact lens is a soft contact lens. 
   
   
       34 . The biomedical device of  claim 31 , wherein the contact lens is a hydrogel contact lens. 
   
   
       35 . The biomedical device of  claim 28 , wherein the device is an intraocular lens. 
   
   
       36 . The biomedical device of  claim 35 , wherein the intraocular lens is a phakic intraocular lens. 
   
   
       37 . The biomedical device of  claim 35 , wherein the intraocular lens is an aphakic intraocular lens. 
   
   
       38 . The biomedical device of  claim 28 , wherein the device is a corneal implant. 
   
   
       39 . The biomedical device of  claim 28 , 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. 
   
   
       40 . A method of making a biomedical device comprising:
 (a) providing a monomer mixture comprising the silicon-containing monomer of  claim 21  and at least a second monomer;   (b) subjecting the monomer mixture to free radical polymerization conditions to provide a polymerized device; and   (c) extracting the polymerized device.   
   
   
       41 . The method of  claim 40 , wherein the step of extracting is performed with a non-flammable solvent. 
   
   
       42 . The method of  claim 40  wherein the step of extracting is performed with water. 
   
   
       43 . The method of  claim 40 , further comprising the step of packaging and sterilizing the extracted polymerized device.