Polymeric composition for ocular devices

Abstract

Polymeric and co-polymeric compositions useful for preparing ophthalmic and ocular devices, such as implantable intraocular lenses (IOL) and contact lenses, and processes of forming the compositions and devices are provided. The disclosed polymeric or co-polymeric composition may include a curcuminoid compound as a UV-blocker, and is derived from a pre-polymerization mixture of monomers which comprises at least 50 weight percents acrylate monomers and exhibiting visible light transparency and ultraviolet light opacity. The disclosed co-polymeric composition may alternatively, or in addition, be derived from a pre-polymerization mixture of defined monomers.

What is claimed is: 
     
         1 . A co-polymeric composition comprising a polymeric backbone composed of a plurality of backbone units covalently linked to one another, said backbone units being derived from a pre-polymerization mixture of monomers which comprises:
 a first aromatic acrylate monomer, characterized as forming a first homopolymer having a refractive index that ranges from 1.50 to 1.53;   a second aromatic acrylate monomer, characterized as forming a second homopolymer having a Tg lower by a range of 2° C. to 15° C. than a Tg of said first homopolymer;   a third monomer, characterized as forming a third homopolymer having a Tg that ranges from 10 to 35° C.;   a fourth monomer, characterized as forming a fourth homopolymer which is capable of absorbing water to at least 30% of the total weight of said fourth homopolymer; and   a fifth monomer, being a crosslinking monomer,   wherein:   a concentration of said first aromatic acrylate monomer ranges from 50% to 60% of the total weight of the composition;   a concentration of said second aromatic acrylate monomer ranges from 15% to 20% of the total weight of the composition;   a concentration of said third monomer ranges from 10% to 15% of the total weight of the composition;   a concentration of said fourth monomer ranges from 5% to 10% of the total weight of the composition;   a concentration of said fifth monomer ranges from 2% to 5% of the total weight of the composition; and   the composition is being formulated for ophthalmic application and characterized by at least one of:   a glass transition temperature not higher than 15° C.;   a loop pull force mechanical strength of at least 40 grams;   a Shore A hardness that ranges from 77 to 80; and   an unfolding time of less than 6 seconds.   
     
     
         2 . The composition of  claim 1 , wherein said first aromatic monomer is selected from the group consisting of 2-phenoxyethyl acrylate, 2-phenoxy ethyl methacrylate, 2-benzyloxy ethyl acrylate, 2-benzyloxy ethyl methacrylate and combinations thereof. 
     
     
         3 . The composition of  claim 1 , wherein said second aromatic monomer is selected from the group consisting of 2-phenylethyl acrylate, benzyl acrylate, cyclohexyl acrylate, 2-chlorophenyl acrylate, 4-methyl benzyl acrylate, 2,4,6-tribromophenyl acrylate, pentabromophenyl acrylate and any combinations thereof. 
     
     
         4 . The composition of  claim 1 , wherein said third monomer is selected from the group consisting of cellosolve methacrylate, methoxy ethyl acrylate, polyethylene glycol monomethacrylate, 1-dihydroxyperflurobutyl methacrylate, 2,5-dibromopropyl methacrylate, hexyl methacrylate, glycerol monomethacrylate, trifluroethyl methacrylate, butyl methacrylate, n-ocyl/isooctyl methacrylate, n-decyl/isodecyl methacrylate, ethyl methacrylate, ethylene triglycol methacrylate, butyl diglycol methacrylate, methoxy polyethylene glycol 350 methhacrylate, methoxy polyethylene glycol 500 methhacrylate, methoxy polyethylene glycol 1000 methhacrylate, methoxy polyethylene glycol 2000 methhacrylate, methoxy polyethylene glycol 5000 methhacrylate, polypropylene glycon methacrylate, ethoxytriglycol methacrylate, 2-ethoxyethoxy ethyl methacrylate, methoxy triethyleglycol methacrylate, phenoxy polyethylene glycol monomethacrylate and any combinations thereof. 
     
     
         5 . The composition of  claim 1 , wherein said forth monomer is selected from the group consisting of hydroxyl ethyl methacrylate, glycerol monomethacrylate, ethylene triglycol methacrylate, butyl diglycol methacrylate, methoxy polyethylene glycol 350 methhacrylate, methoxy polyethylene glycol 500 methhacrylate, methoxy polyethylene glycol 1000 methhacrylate, methoxy polyethylene glycol 2000 methhacrylate, methoxy polyethylene glycol 5000 methhacrylate, polypropylene glycon methacrylate, ethoxytriglycol methacrylate, methoxy triethyleglycol methacrylate, phenoxy polyethylene glycol monomethacrylate and any combinations thereof. 
     
     
         6 . The composition of  claim 1 , wherein said fifth monomer is selected from the group consisting of ethylene glycol dimethacrylate, 1,4-butane diol diacrylate, glycerol dimethacrylate, allyl methacrylate, 1,6 heaxane diol diacrylate, 1,4-butanediol dimethacrylate, 1,6-hexane diol dimethacrylate and any combinations thereof. 
     
     
         7 . The composition of  claim 1 , wherein said mixture further comprises a curing agent selected from the group consisting of a peroxy catalyst, an oxide catalysts, tert-butyl peroxy-2-ethylhexanoate, 2,4,6-trimethylbenzoyldiphenylphosphine oxide and any combinations thereof. 
     
     
         8 . The composition of  claim 1 , further comprising an ultraviolet absorbing compound selected from the group consisting of a benzophenone, 2-hydroxybenzophenone, 2-(2-hydroxyphenyl)benzotriazole, 2-acryloxyethoxy hydroxyl benzophenone, phenol-2-(5-chloro-2H-benozotriazol-2-yl)-6-(1,1-)dimethyl-4-methyl, 4-benzoyl-3-hydroxyphenyl-2-methacrylate, 2-[4-(2h-1,2,3-benzotriazol2-yl)-3-hydroxyphenoxy]ethyl-2-methacrylate and any combinations thereof. 
     
     
         9 . The composition of  claim 1 , further comprising at least one curcuminoid compound incorporated therein or thereon said curcuminoid compound is selected from the group consisting of curcumin, bisdemethoxycurcumin, monodemethoxycurcumin and tetrahydroxycurcumin. 
     
     
         10 . A co-polymeric composition comprising a polymeric backbone composed of a plurality of backbone units covalently linked to one another and a curcuminoid compound incorporated in or on the composition, said backbone units being derived from a pre-polymerization mixture of monomers which comprises:
 a first aromatic acrylate monomer, characterized as forming a first homopolymer having a refractive index that ranges from 1.50 to 1.53;   a second aromatic acrylate monomer, characterized as forming a second homopolymer having a Tg lower by a range of 2° C. to 30° C. than a Tg of said first homopolymer;   a third monomer, characterized as forming a third homopolymer having a Tg lower than 35° C.;   a fourth monomer, characterized as forming a fourth homopolymer which is capable of absorbing water to at least 20% of the total weight of said fourth homopolymer; and   a fifth monomer, being a crosslinking monomer,   wherein:   a concentration of said first aromatic acrylate monomer ranges from 50% to 60% of the total weight of the composition;   a concentration of said second aromatic acrylate monomer ranges from 15% to 20% of the total weight of the composition;   a concentration of said third monomer ranges from 10% to 15% of the total weight of the composition;   a concentration of said fourth monomer ranges from 5% to 10% of the total weight of the composition;   a concentration of said fifth monomer ranges from 2% to 5% of the total weight of the composition; and   the composition is formulated for ophthalmic application and characterized by at least one of:   a glass transition temperature not higher than 15° C.;   a loop pull force mechanical strength of at least 40 grams;   a Shore A hardness that ranges from 77 to 80; and   an unfolding time of less than 6 seconds.   
     
     
         11 . The composition of  claim 10 , having a visible light transmission of at least 95% of incident visible light. 
     
     
         12 . The composition of  claim 10 , having a refractive index of at least 1.53. 
     
     
         13 . The composition of  claim 10 , having loop pull force mechanical strength of at least 40 grams. 
     
     
         14 . The composition of  claim 10 , having an unfolding time of less than 6 seconds. 
     
     
         15 . The composition of  claim 10 , having a leachable content of less than 0.6%. 
     
     
         16 . An ophthalmic or ocular device, comprising the composition of  claim 10 . 
     
     
         17 . The device of  claim 16 , selected from the group consisting of an intraocular lens (IOL), a contact lens, an implantable ocular device, a keratoprosthesis, a phakic lens, an aphakic lens, a corneal ring, a capsular bag extension ring, a corneal inlay and a corneal onlay. 
     
     
         18 . The composition of  claim 10 , further characterized by at least one of:
 a visible light transmission of at least 97% of incident visible light; and   a refractive index of at least 1.53.   
     
     
         19 . An ophthalmic or ocular device, comprising the composition of  claim 1 . 
     
     
         20 . The ophthalmic or ocular device of  claim 19 , selected from the group consisting of an intraocular lens (IOL), a contact lens, an implantable ocular device, a keratoprosthesis, a phakic lens, an aphakic lens, a corneal ring, a capsular bag extension ring, a corneal inlay and a corneal onlay.