Interpenetrating polymer network hydrophilic hydrogels for contact lens

Abstract

An interpenetrating polymer network (IPN) composition and a process for the manufacture of hydrogel contact lens using the invention material. The polymeric materials are formed by polymerization of: (1) an unsaturated alkyl(meth)acrylate or its derivatives such as 2-hydroxyethyl methacrylate as the principle monomer; (2) optionally vinyl containing comonomer(s) to enhance the resulting hydrogel water absorbing capability; (3) polymerizable multi-functional crosslinking agent(s); (4) an irradiation initiator and/or thermal initiator; (5) optionally other additives to impart the resulting hydrogel specific properties such as ultra-violet blocking ability and handling colors; in the presence of a soluble, hydrophilic IPN agent such as polyvinylpyrrolidone (PVP) or poly-2-ethyl-2-oxazoline (PEOX) with a specific molecular weight range. The novel hydrophilic hydrogel material in the present invention can be used to produce a spherical contact lens, a toric contact lens, a multifocal contact lens, a toric-multifocal contact lens, and other medical devices. The inventive hydrogel material shows a low degree of surface friction, a low dehydration rate, and a high degree of biodeposit resistance.

What is claimed is:  
     
         1 . A hydrogel composition comprising: 
 I. at least one polymer; and    II. at least one interpenetrating polymer network agent, interpenetrating said at least one polymer, selected from the group consisting of: 
 (A) at least one polymer comprising one or more monomeric units comprising at least one ═N—C(═O)— group;  
 (B) at least one polymer comprising one or more monomeric units comprising at least on N-oxide group;  
 (C) at least one polymer comprising both ═N—C(═O)— and N-oxide groups of (A) and (B); and  
 (D) mixtures thereof;  
   III. at least one polymer crosslinker selected from the group consisting of polyethylene glycol dimethacrylate and ethylene glycol dimethacrylate; and    IV. optionally, at least one material selected from the group consisting of monomers, polymerization initiators, ultraviolet absorbing materials, colorants, antiseptic agents, and combinations thereof.    
     
     
         2 . A hydrogel composition comprising: 
 I. at least one polymer; and    II. at least one interpenetrating polymer network agent, interpenetrating said at least one polymer, selected from the group consisting of: 
 (A) at least one polymer comprising one or more monomeric units comprising at least one ═N—C(═O)— group;  
 (B) at least one polymer comprising one or more monomeric units comprising at least on N-oxide group;  
 (C) at least one polymer comprising both ═N—C(═O)— and N-oxide groups of (A) and (B); and  
 (D) mixtures thereof;  
   III. at least one sulfoxide containing material selected from the group consisting of sulfoxide-containing methacrylates, sulfoxide containing acrylates, and combinations thereof; and    IV. optionally, at least one material selected from the group consisting of monomers, polymer crosslinkers, polymerization initiators, ultraviolet absorbing materials, colorants, antiseptic agents, and combinations thereof.    
     
     
         3 . A interpenetrating polymer network, contact lens composition comprising: 
 I. at least one polymer; and    II. at least one interpenetrating polymer network agent, interpenetrating said at least one polymer, selected from the group consisting of: 
 (A) at least one polymer comprising one or more monomeric units comprising at least one ═N—C(═O)— group;  
 (B) at least one polymer comprising one or more monomeric units comprising at least on N-oxide group;  
 (C) at least one polymer comprising both ═N—C(═O)— and N-oxide groups of (A) and (B); and  
 (D) mixtures thereof; and  
   III. optionally, at least one material selected from the group consisting of monomers, polymer crosslinkers, polymerization initiators, ultraviolet absorbing materials, colorants, antiseptic agents, and combinations thereof.    
     
     
         4 . The composition of    claim 1   ,    2   , or  3  wherein said at least one polymer comprises at least one polymer comprising at least one monomer selected from the group consisting of: 2-hydroxyethylmethacrylate, 2-hydroxyethylacrylate, methylmethacrylate; methylacrylamide; methacrylamide; N,N-dimethyl-diacetoneacrylamide; 2-phosphatoethylmethacrylate; di-, tri-, tetra-, penta-, . . . polyethyleneglycol monoacrylate and methacrylate; 4- and 2-methyl-5-vinylpyridine; N-(3-methacrylamidopropyl)-N,N-dimethylamine; N-(3-methacrylamidopropyl) -N, N, N-trimethylarnine; 1-vinyl-, and 2-methyl-1-vinlyimidazole; N-(3-acrylamido-3-methylbutyl)-N,N-dimethylamine; 3,-hydroxypropyl methacrylate; N-vinyl imidazole; N-vinyl succinimide; N-vinyl diglycolylimide; N-vinyl glularimide; N-vinyl-3-morpholinorie; N-vinly-5-methyl-3-morpholinone; propyl methacrylate; propyla crylate; butyl acrylate; pentyl acrylate; dimethyl diphenyl methylvinyl siloxane; N-(1,1-dimethyl-3-oxobutyl)acrylamide; 2-ethyl-2-(hydroxy-methyl)-1,3-propanediol trimethacrylate; X-(dimethylvinylsilyi)-ω-[(dimethylvinyl-silyl)oxy]-dimethyl diphenyl methylvinyl siloxane; butyl(meth)acrylate; 2-hydroxybutyl methacrylate; vinyl acetate; pentyl methacrylate; vinyl propionate; 3-hydroxy-2-naphthyl methacrylate; vinyl alcohol; N-(formylmethyl)acrylamide; 2-ethoxyethyl methacrylate; 4-t-butyl-2-hydroxycyclohexyl methacrylate; 2-(methacryloyloxy)ethyl vinyl carbonate; vinyl[3-[3,3,3-trimethyl- 1,1 -bis(trimethylsiloxy)disiloxany]propyl] carbonate; 4,4′-(tetrapentacontmethylhepta-cosasiloxanylene)di-1-butanol; N-carboxy-β-alanine N-vinyl ester; 2-melhacryloyloxyethyl phosphorylcholine; and combinations thereof.  
     
     
         5 . The composition of    claim 1   ,    2   , or  3  wherein said at least one interpenetrating polymer network agent comprises from approximately 1% by dry weight to approximately 14% by dry weight and preferably from approximately 5% by dry weight to approximately 10% by dry weight of said composition.  
     
     
         6 . The composition of    claim 2    or    3    further comprising at least one sulfoxide containing material selected from the group consisting of sulfoxide-containing methacrylates, sulfoxide containing acrylates, and combinations thereof.  
     
     
         7 . The composition of    claim 1   ,    2   , or  3  wherein said at least one interpenetrating polymer network agent comprises a weight average molecular weight greater than approximately 10,000.  
     
     
         8 . The composition of    claim 2    or    3    wherein said polymer crosslinker comprises at least one member selected from the group consisting of at least one monomer and at least one polymer.  
     
     
         9 . The composition of    claim 6    wherein said at least one polymer crosslinker comprises a polymer comprising a weight average molecular weight range from approximately 300 to approximately 1500.  
     
     
         10 . The composition of    claim 6    wherein said at least one polymer crosslinker comprises from approximately 0.1% by dry weight to approximately 8% by dry weight and preferably from approximately 0.5% by dry weight to approximately 4% by dry weight of said composition.  
     
     
         11 . The composition of    claim 6    wherein said polymer crosslinker comprises at least one member selected from the group consisting of polyethylene glycol dimethacrylate and ethylene glycol dimethacrylate.  
     
     
         12 . The composition of    claim 1   ,    2   , or  3  wherein said optional monomers comprise at least one monomer selected from the group consisting of methyl methacrylate and N-vinyl lactams.  
     
     
         13 . The composition of    claim 11    wherein said N-vinyl lactam comprises N-vinylpyrrolidone.  
     
     
         14 . The composition of    claim 1   ,    2   , or  3  wherein said interpenetrating network agent comprises at least one agent selected from the group consisting of polyvinylpyrrolidone, polyvinylpyrrolidone iodine, poly-2-ethyl-2-oxazoline and poly(vinylpyridine N-oxide).  
     
     
         15 . An interpenetrating polymer network comprising at least one polymer and at least one interpenetrating polymer network agent interpenetrating said at least one polymer, said interpenetrating polymer network having a water loss of less than approximately 5.0 weight percent after 5 minutes at approximately 75% humidity and approximately 24° C. wherein preferably said at least one polymer comprises at least one member selected from the group consisting of HEMA and MAA, and preferably said agent comprises at least one member selected from the group consisting of polyvinylpyrrolidone, polyvinylpyrrolidone iodine, poly-2-ethyl-2-oxazoline, and poly(vinylpyridine N-oxide).  
     
     
         16 . An interpenetrating polymer network composition comprising sulfoxide.