Polymerizable surfactants and their use as device forming comonomers

Abstract

This invention describes the use of polymerizable surfactants at percent by weight of less than 15% as comonomers in forming ophthalmic devices such as contact lenses, intraocular lenses, corneal implants, etc.

1 . An ophthalmic device comprising: 
 a polymerized comonomer mixture comprising at least one polymerizable surfactant selected from the group consisting of poloxamers having at least one end terminal functionalized, reverse poloxamers having at least one end terminal functionalized, poloxamines having at least one end terminal functionalized, reverse poloxamines having at least one end terminal functionalized and mixtures thereof, wherein the polymerizable surfactant is present in comonomer mixture prior to polymerization at less than 15% by weight.    
   
   
       2 . The ophthalmic device of  claim 1  wherein the ophthalmic device is a contact lens.  
   
   
       3 . The ophthalmic device of  claim 2  wherein the contact lens is a rigid gas permeable contact lens.  
   
   
       4 . The ophthalmic device of  claim 2  wherein the lens is a soft contact lens.  
   
   
       5 . The ophthalmic device of  claim 2  wherein the lens is a hydrogel contact lens.  
   
   
       6 . The ophthalmic device of  claim 1  wherein the lens is an intraocular lens.  
   
   
       7 . The ophthalmic device of  claim 6  wherein the lens is a phakic intraocular lens.  
   
   
       8 . The ophthalmic device of  claim 6  wherein the lens is an aphakic intraocular lens.  
   
   
       9 . The ophthalmic device of  claim 1  wherein the device is a corneal implant.  
   
   
       10 . The ophthalmic device of  claim 1  further comprising as part of the comonomer mixture an organo silicon compound.  
   
   
       11 . The ophthalmic device of  claim 10  wherein the silicon compound is selected from the group consisting of siloxanyl (meth)acrylate, siloxanyl (meth)acrylamide, siloxynyl vinyl carbamate, polymerizable siloxane oligomers and macromonomers and mixtures thereof.  
   
   
       12 . The ophthalmic device of  claim 10  further comprising as part of the monomer mixture at least one member selected from the group consisting of crosslinking agents, internal wetting agents, hydrophilic monomers and toughening agents.  
   
   
       13 . The ophthalmic device of  claim 12  wherein the hydrophilic monomers are selected from the group consisting of hydrophilic acrylic-, methacrylic-, itaconic-, styrenyl-, acrylamido-, methacrylamido- and vinyl-containing monomers and mixtures thereof.  
   
   
       14 . The ophthalmic device of  claim 13  wherein the hydrophilic monomers are selected from the group consisting of monomers containing the acrylic group represented by the formula:  
     
       
         
         
             
             
         
       
     
     wherein X is hydrogen or methyl and Y is —O—, —OQ—, —NH—, —NQ— and —NH(Q)—, and Q is an alkyl or substituted alkyl group; and mixtures thereof.  
   
   
       15 . The ophthalmic device of  claim 13  wherein the vinyl-containing hydrophilic monomers are selected from the group consisting of N-vinyllactams, N-vinylpyrrolidone, N-vinyl-N-methylacetamide, N-vinyl-N-ethylacetamide, N-vinyl-N-ethylformamide, N-vinylformamide, and mixtures thereof.  
   
   
       16 . The ophthalmic device of  claim 13  wherein the hydrophilic monomers are selected from the group consisting of as N,N-dimethylacrylamide, 2-hydroxyethyl methacrylate, glycerol methacrylate, 2-hydroxyethyl methacrylamide, methacrylic acid, acrylic acid and mixtures thereof.  
   
   
       17 . The ophthalmic device of  claim 1  further comprising as part of the comonomer mixture an ethylenically unsaturated hydrophilic monomer selected from the group consisting of ethylenically unsaturated polyoxyalkylenes, ethylenically unsaturated polyacrylamides, ethylenically unsaturated polyvinylpyrrolidones, ethylenically unsaturated polyvinyl alcohols, ethylenically unsaturated poly (hydroxyethyl methacrylate), ethylenically unsaturated N-alkyl-N-vinyl acetamides and mixtures thereof.  
   
   
       18 . The ophthalmic device of  claim 17  wherein the ethylenic unsaturation is provided by a group selected from (meth)acrylate, (meth)acrylamide, styrenyl, alkenyl, vinyl carbonate, vinyl carbamate groups and mixtures thereof.  
   
   
       19 . The ophthalmic device of  claim 1  further comprising hydrophobic monomers.  
   
   
       20 . The ophthalmic device of  claim 19  wherein the hydrophobic monomer is selected from the group consisting of alkyl (meth)acrylates, N-alkyl (meth)acrylamides, alkyl vinylcarbonates, alkyl vinylcarbamates, fluoroalkyl (meth)acrylates, N-fluoroalkyl (meth)acrylamides, N-fluoroalkyl vinylcarbonates, N-fluoroalkyl vinylcarbamates, silicone-containing (meth)acrylates, (meth)acrylamides, vinyl carbonates, vinyl carbamates, styrenic monomers such as styrene, alpha-methyl styrene, ρ-methyl styrene, ρ-t-butyl monochloro styrene, and ρ-t-butyl dichloro styrene; polyoxypropylene (meth)acrylates, methyl methacrylate, dodecyl methacrylate, octafluoropentyl methacrylate, perfluorooctyl methacrylate, methacryoyl oxypropyl tris(trimethylsiloxy)silane (TRIS) and mixtures thereof.  
   
   
       21 . The ophthalmic device of  claim 1  further comprising a free radical thermal polymerization initiators selected from the group consisting of organic peroxides such as acetyl peroxide, lauroyl peroxide, decanoyl peroxide, stearoyl peroxide, benzoyl peroxide, t-butyl peroxypivalate, peroxydicarbonate and mixtures thereof.  
   
   
       22 . The ophthalmic device of  claim 1  further comprising a UV initiator.  
   
   
       23 . A method of forming an ophthalmic device comprising: 
 providing a polymerizable mixture comprising a comonomer mixture comprising at least one polymerizable surfactant selected from the group consisting of poloxamers having at least one end terminal functionalized, reverse poloxamers having at least one end terminal functionalized, poloxamines having at least one end terminal functionalized, reverse poloxamines having at least one end terminal functionalized and mixtures thereof, wherein the polymerizable surfactant is present in an amount of less than 15% by weight of the polymerizable monomer mixture;    subjecting the polymerizable mixture to polymerizing conditions; and, shaping the polymerizable mixture into the desired shape of the ophthalmic device.    
   
   
       24 . The method of  claim 23  wherein the step of shaping occurs after subjecting the polymerizable mixture to polymerization conditions.  
   
   
       25 . The method of  claim 23  wherein the step of shaping comprises cutting, lathing, polishing and combinations thereof.  
   
   
       26 . The method of  claim 23  further comprising the step of placing the polymerizable mixture comprising a comonomer mixture comprising at least one polymerizable surfactant selected from the group consisting of poloxamers having at least one end terminal functionalized, reverse poloxamers having at least one end terminal functionalized, poloxamines having at least one end terminal functionalized, reverse poloxamines having at least one end terminal functionalized and mixtures thereof in a mold prior to the step of subjecting the polymerizable mixture to polymerization conditions.  
   
   
       27 . The method of  claim 26  wherein the step of polymerizing is conducted in a mold selected from the group consisting of spinning molds and stationary molds.  
   
   
       28 . The method of  claim 23  wherein the step of polymerizing is conducted in an appropriate mold or vessel to form buttons, plates or rods.  
   
   
       29 . The method of  claim 23  further comprising the step of hydrating the polymerized mixture.  
   
   
       30 . The method of  claim 23  wherein the ophthalmic device formed is selected from the group consisting of rigid gas permeable contact lens, soft contact lens, intraocular lens, phakic intraocular lens, aphakic intraocular lens and corneal implant.