High Refractive-Index, Hydrophilic Monomers and Polymers, and Ophthalmic Devices Comprising Such Polymers

Abstract

A hydrophilic, aromatic-based monomer has an aromatic group substituted with at least one hydrophilic substituent and a reactive functional group. Polymers comprising such a hydrophilic, aromatic-based monomers avoid or reduce the risk of forming vacuoles of absorbed water. Furthermore, such polymers have high refractive index, and, thus, are advantageously used for making ophthalmic devices, such as intraocular lenses, contact lenses, corneal rings, corneal inlays, and keratoprostheses.

1 . A compound having a formula of
   G-D-Ar  (I)   wherein Ar is a C 6 -C 24  aromatic group having a hydrophilic substituent selected from the group consisting of —COOH, —CH 2 —CH 2 OH, —(CHOH) 2 —CH 2 OH, —CH 2 —CHOH—CH 2 OH, —C(O)O—NH 2 , —C(O)—N(CH 3 ) 2 , poly(alkyleneglycol) and combinations thereof, D is a divalent linking group, and G is a reactive functional group.   
     
     
         2 . The compound of  claim 1 , wherein the hydrophilic substituent is selected from the group consisting of —COOH, —CH 2 —CH 2 OH, and combinations thereof. 
     
     
         3 . The compound of  claim 1 , wherein the hydrophilic substituent is poly(alkylene glycol). 
     
     
         4 . The compound of  claim 6 , wherein said poly(alkylene glycol) is poly(ethylene glycol) having a formula of —(O—CH 2 —CH 2 ) n OH, wherein n is an integer and 1≦n≦50. 
     
     
         5 . A compound having a formula of
   G-D-Ar  (I)   wherein Ar is a C 6 -C 24  aromatic group having a hydrophilic substituent selected from the group consisting of carboxamide, dialkyl-substituted carboxamide, amino, alkanolamino, sulfonate, phosphonate, sulfate, phosphate, ureido, substituted sugars, and combinations thereof, D is a divalent linking group, and G is a reactive functional group.   
     
     
         6 . The compound of  claim 1 , wherein G is selected from the group consisting of vinyl, allyl, acryloyl, acryloyloxy, methacryloyl, methacryloyloxy, epoxide, isocyanate, isothiocyanate, amino, hydroxyl, mercapto, anhydride, carboxylic, fumaryl, styryl, and combinations thereof. 
     
     
         7 . The compound of  claim 1 , wherein D is selected from the group consisting of saturated straight C 1 -C 10  hydrocarbons, unsaturated straight C 1 -C 10  hydrocarbons, saturated branched C 3 -C 10  hydrocarbons, unsaturated branched C 3 -C 10  hydrocarbons, saturated cyclic C 3 -C 10  hydrocarbons, unsaturated cyclic C 3 -C 10  hydrocarbons, and alkyloxy substituents. 
     
     
         8 . The compound of  claim 1 , wherein the compound has a formula of 
       
         
           
           
               
               
           
         
         wherein R is hydrogen or CH 3 ; D is a divalent group selected from the group consisting of saturated straight C 1 -C 10  hydrocarbons, unsaturated straight C 1 -C 10  hydrocarbons, saturated branched C 3 -C 10  hydrocarbons, unsaturated branched C 3 -C 10  hydrocarbons, saturated cyclic C 3 -C 10  hydrocarbons, unsaturated cyclic C 3 -C 10  hydrocarbons, and alkoxy substituents; E is selected from the group consisting of carboxy, carboxamide, and monohydric and polyhydric alcohol substituents; and m is an integer from 1 to, and including, 5. 
       
     
     
         9 . The compound of  claim 1 , wherein the compound is 
       
         
           
           
               
               
           
         
         wherein R is hydrogen or CH 3 . 
       
     
     
         10 . The compound of  claim 1 , wherein the compound is 
       
         
           
           
               
               
           
         
         wherein R is hydrogen or CH 3 . 
       
     
     
         11 . The compound of  claim 1 , wherein the hydrophilic, aromatic-based monomer has a formula of 
       
         
           
           
               
               
           
         
         wherein R is hydrogen or CH 3 , and R 1  is —C(O)O—NH 2  or —C(O)—N(CH 3 ) 2 .