Nanohybrid polymers for ophthalmic applications

Abstract

The present invention relates to novel materials particularly useful for ophthalmic applications and methods for making and using the same. More particularly, the present invention relates to relatively soft, optically transparent, foldable, high refractive index materials particularly suited for use in the production of intraocular lenses, contact lenses, and other ocular implants and to methods for manufacturing and using the same.

What is claimed is: 
     
         1 . A composition comprising: a high refractive index monomer comprising a carbazole or naphthyl moiety, carbazole, naphthalene or a naphthyl group; a hydrophobic monomer, a hydrophilic monomer, and a crosslinker. 
     
     
         2 . The composition of  claim 1 , wherein said composition includes an ultraviolet light absorbing material. 
     
     
         3 . The composition of  claim 1 , wherein said composition includes an ultraviolet light absorbing material selected from the group consisting of beta-(4-benzotriazoyl-3-hydroxyphenoxy) ethyl acrylate, 4-(2-acryloxyethoxy)-2-hydroxybenzophenone, 4-methacryloxy-2-hydroxybenzo-phenone, 2-(2′-methacryloxy-5′-methylphenyl) benzo-triazole, 2-(2′-hydroxy-5′-methacryloxy-ethylphenyl)-2H-benzotriazole, 2-[3′-tert-Butyl-T-hydroxy-5′-(3″-methacyloyloxypropyl) phenyl]-5-chlorobenzotriazole, 2-(3′-tert-Butyl-5′-(3-dimethylvinylsilylp-ropoxy)-2′-hydroxyphenyl]-5-methoxybenzo-triazole, 2-(3′-Allyl-2′-hydroxy-5-′-methylphenyl) benzotriazole, 2-[3′-tert-Butyl-2′-hydroxy-5′-[3″-methacryloyl-oxypropoxy) phenyl]-5-methoxybenzotriazole and 2-[3′-tert-Butyl-2′-hydr-oxy-5′-(3″-methacryloyloxypropoxy) phenyl]-5-chloro-benzotriazole. 
     
     
         4 . A composition of  claim 1 , wherein the ultralight absorbing material is vinyl anthracene or derivatives there. 
     
     
         5 . The composition of  claim 1 , wherein said composition includes a monomeric dye. 
     
     
         6 . A composition of  claim 1 , wherein the monomeric dye absorbs light in the 400-700 nm region. 
     
     
         7 . A composition of  claim 1 , wherein the monomeric dye is disperse red 1 methacrylate. 
     
     
         8 . A composition of  claim 1 , wherein the monomeric dye is disperse red 13 methacrylate. 
     
     
         9 . A composition of  claim 1 , wherein the monomeric dye is disperse red 1 acrylate. 
     
     
         10 . A composition of  claim 1 , wherein the monomeric dye is disperse red 13 acrylate. 
     
     
         11 . A composition of  claim 1 , wherein the hydrophilic monomer(s) is selected from the group consisting of 2-hydroxy-ethylacrylate, 2-hydroxyethylmethacrylate, acrylamide, N-ornithine acrylamide, N-(2-hydroxypropyl)acrylamide, polyethyleneglycol acrylates, polyethyleneglycol methacrylates, N-vinyl pyrolidone, N-phenylacrylamide, dimethylaminopropyl methacrylamide, acrylic acid, benzylmeth-acrylamide, 4-hydroxybutylmethacrylate, glycerol mono methacrylate, glycerol mono acrylate, 2-sulfoethylmethacrylate, phenoxyethyl acrylate, phenoxy ethyl methacrylate, 2-(2-ethoxyethoxy)ethyl acrylate, 2-(2-ethoxyethoxy)ethyl methacrylate, furfuryl acrylate, furfuryl methacrylate, and methylthioethylacrylamide. 
     
     
         12 . A composition of  claim 1 , wherein the hydrophobic monomer(s) is selected from the group consisting of Lauryl methacrylate, lauryl acrylate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, n-decyl acrylate, n-decyl methacrylate, hexyl acrylate, hexyl metcarylate, stearyl acrylate, stearyl methacrylate, isodecyl acrylate, isodecyl methacrylate, isobornyl acrylate, isobornyl methacrylate, vinyl laurate, vinyl stearate, 1-hexadecyl acrylate, 1-hexadecyl methacrylate, n-myristyl acrylate, n-myristyl methacryalte, n-dodecyl methacrylamide, butyl acrylate, n-butyl methacrylate, isooctyl acrylate, isotridecyl acrylate, isooctyl methacrylate, and isotridecyl methacrylate. 
     
     
         13 . A copolymer comprising:
 a high refractive index monomer comprising a fused ring aromatic moiety coupled to a vinylically unsaturated moiety;   b) a hydrophobic monomer; and   a hydrophilic monomer.   
     
     
         14 . A copolymer of  claim 13  wherein the high refractive index monomer comprises; 
       
         
           
           
               
               
           
         
         wherein:
 R 1 -R 4  are separately and independently, H, C, X, or R c ; 
 R c  is any hydrocarbon moiety; and 
 X is any heteratom, providing that at least one of R 1 -R 4  must be a fused ring aromatic structure. 
 
       
     
     
         15 . A copolymer of  claim 13  wherein the high refractive index monomer comprises an ethylenically unsaturated moiety and a fused ring aromatic moiety. 
     
     
         16 . A copolymer of  claim 15  wherein the ethylenically saturated moiety comprises: 
       
         
           
           
               
               
           
         
         wherein:
 R 1 , R 3  and R 4  are separately and independently, H, C, X, or R c ; 
 R c  is any hydrocarbon moiety; and 
 X is any heteratom. 
 
       
     
     
         17 . A copolymer in accordance with  claim 13 , wherein the high refractive index monomer is selected from the group consisting of vinyl carbazole, vinyl naphthalene, and vinyl anthracene. 
     
     
         18 . A copolymer according to  claim 13  which comprises:
 a) at least about 15% by weight high refractive index monomer; 
 b) at least about 20 weight percent hydrophobic monomer; 
 c) at least about 10 weight percent hydrophilic monomer. 
 
     
     
         19 . A copolymer according to  claim 18  wherein the high refractive index monomer is selected from the group consisting of vinyl naphthalene, vinyl carbazole, and vinyl anthracene. 
     
     
         20 . A method of making a high refractive index copolymer comprising the steps of:
 a) providing a mixture of monomers specified in  claim 1 ;   b) mixing the monomer for a time period of at least 20 minutes at about room temperature;   c) sonicating the mixture of monomers for a time period of at least 10 minutes at about room temperature to produce copolymer nanoclusters in substantially hydrophobic matrix.   
     
     
         21 . A method according to  claim 20  which includes a further step of mixing the sonicated mixture for a time period of at least about 15 minutes.