Ocular lens material and process for producing the same

Abstract

An ocular lens material comprising a siloxane-containing polymer obtained by polymerizing a monomer mixture containing (A) a siloxane macromonomer having at least two active unsaturated groups and a number average molecular weight of 2,000 to 100,000; and (B) a vinyl ester of lower fatty acid as essential components. An ocular lens material comprising a polymer obtained by saponification of the siloxane-containing polymer. Processes for producing the ocular lens materials. The ocular lens materials are excellent not only in lipid-stain resistance, wettability and oxygen permeability, but also in flexibility, particularly, shape recovery at the same time.

1 . An ocular lens material comprising a siloxane-containing polymer obtained by polymerizing a monomer mixture containing (A) a siloxane macromonomer having at least two active unsaturated groups and a number average molecular weight of 2,000 to 100,000; and (B) a vinyl ester of lower fatty acid as essential components.  
     
     
         2 . The ocular lens material of  claim 1 , wherein said monomer mixture further contains (C) a silicon-containing monomer.  
     
     
         3 . The ocular lens material of  claim 1 , wherein said monomer mixture further contains (D) a fluorine-containing monomer.  
     
     
         4 . The ocular lens material of  claim 2 , wherein the weight ratio of the total of said siloxane macromonomer (A) and said silicon-containing monomer (C) to said vinyl ester of lower fatty acid (B), the total weight of (A) and (C)/the weight of (B), is 30/70 to 90/10.  
     
     
         5 . The ocular lens material of  claim 3 , wherein the weight ratio of the total of said siloxane macromonomer (A), said vinyl ester of lower fatty acid (B) and said silicon-containing monomer (C) to said fluorine-containing monomer (D), the total weight of (A), (B) and (C)/the weight of (D), is at least 20/80.  
     
     
         6 . The ocular lens material of  claim 2 , wherein the weight ratio of said siloxane macromonomer (A) to said silicon-containing monomer (C), the weight of (A)/the weight of (C), is at least 20/80.  
     
     
         7 . The ocular lens material of  claim 1 , wherein said siloxane macromonomer (A) is a macromonomer represented by the formula (I-1):  
       A 1 -(-U 1 —S 1 —) n —U 2 —S 2 —U 3 -A 2    (I-1)  
       wherein each of A 1  and A 2  is independently an active unsaturated group, an active unsaturated group having an alkylene group having 1 to 20 carbon atoms or an active unsaturated group having an alkylene glycol group having 1 to 20 carbon atoms; 
 U 1  is a diurethane type group which contains urethane bonds formed with adjacent A 1  and adjacent S 1  on both sides or which contains urethane bonds with adjacent two S 1  on both sides;  
 U 2  is a diurethane type group which contains urethane bonds formed with adjacent A 1  and adjacent S 2  on both sides or which contains urethane bonds with adjacent S 1  and adjacent S 2  on both sides;  
 U 3  is a diurethane type group which contains urethane bonds formed with adjacent S 2  and adjacent A 2  on both sides;  
 each of S 1  and S 2  is independently a group represented by the formula:  
                     
 in which each of R 1  and R 2  is independently an alkylene group having 1 to 20 carbon atoms, each of R 3 , R 4 , R 5 , R 6 , R 7  and R 8  is independently a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms which may be substituted with a fluorine atom, or a group represented by the formula:  
 A 3 -U 4 —R—O—R 2 -  
 in which A 3  is an active unsaturated group, an active unsaturated group having an alkylene group having 1 to 20 carbon atoms or an active unsaturated group having an alkylene glycol group having 1 to 20 carbon atoms, U 4  is a urethane type group which contains urethane bonds formed with adjacent A 3  and adjacent R 1  on both sides, each of R 1  and R 2  is the same as the above, x is an integer of 1 to 1500, y is 0 or an integer of 1 to 1499, and x+y is an integer of 1 to 1500; and  
 n is 0 or an integer of 1 to 10; or  
 a macromonomer represented by the formula (I-2):  
 B 1 —S 3 —B 1   (I-2)  
 wherein B 1  is an active unsaturated group having urethane bond, and S 3  is a group represented by the formula:  
                     
 in which each of R 1  and R 2  is independently an alkylene group having 1 to 20 carbon atoms, each of R 3 , R 4 , R 5 , R 6 , R 7  and R 8  is independently a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms which may be substituted with a fluorine atom, or a group represented by the formula:  
 A 3 —U 4 —R 1  —O—R 2 -  
 in which A 3  is an active unsaturated group, an active unsaturated group having an alkylene group having 1 to 20 carbon atoms or an active unsaturated group having an alkylene glycol group having 1 to 20 carbon atoms, U 4  is a urethane type group which contains urethane bonds formed with adjacent A 3  and adjacent R 1  on both sides, each of R 1  and R 2  is the same as the above, x is an integer of 1 to 1500, y is 0 or an integer of 1 to 1499, and x+y is an integer of 1 to 1500.  
 
     
     
         8 . The ocular lens material of  claim 1 , wherein said vinyl ester of lower fatty acid (B) is a compound represented by the formula (II):  
       
         
           
           
               
               
           
         
       
       wherein R is hydrogen atom or an alkyl group having 1 to 15 carbon atoms which may be substituted with a halogen atom.  
     
     
         9 . The ocular lens material of  claim 1 , wherein said vinyl ester of lower fatty acid (B) is vinyl acetate, vinyl propionate or vinyl pivalate.  
     
     
         10 . The ocular lens material of  claim 2 , wherein said silicon-containing monomer (C) is a silicon-containing (meth)acrylate.  
     
     
         11 . The ocular lens material of  claim 2 , wherein said silicon-containing monomer (C) is tris(trimethylsiloxy)silylpropyl acrylate.  
     
     
         12 . The ocular lens material of  claim 3 , wherein said fluorine-containing monomer (D) is a fluoroalkyl (meth)acrylate.  
     
     
         13 . An ocular lens material comprising a polymer prepared by saponifying a siloxane-containing polymer obtained by polymerizing a monomer mixture containing 
 (A) a siloxane macromonomer having at least two active unsaturated groups and a number average molecular weight of 2,000 to 100,000; and    (B) a vinyl ester of lower fatty acid as essential components.    
     
     
         14 . A process for producing an ocular lens material, characterized by preparing a siloxane-containing polymer by polymerization of a monomer mixture containing 
 (A) a siloxane macromonomer having at least two active unsaturated groups and a number average molecular weight of 2,000 to 100,000; and    (B) a vinyl ester of lower fatty acid as essential components; and then subjecting said siloxane-containing polymer to saponification.    
     
     
         15 . The process of  claim 14 , wherein said saponification is carried out by alkali treatment.  
     
     
         16 . The process of  claim 15 , wherein a methanol aqueous solution containing sodium hydroxide in a concentration of 0.01 to 1 mol/L is used for said alkali treatment as a treatment solution.  
     
     
         17 . The process of  claim 16 , wherein the volume ratio of methanol to water in said methanol aqueous solution, methanol/water, is 30/70 to 90/10.  
     
     
         18 . The process of  claim 15 , wherein after preparing said siloxane-containing polymer, a dye is dispersed in the siloxane-containing polymer and then, said dye is fixed to the siloxane-containing polymer during said saponification by said alkali treatment.  
     
     
         19 . The process of  claim 14 , wherein after preparing said siloxane-containing polymer, photo-irradiation is conducted and saponification is carried out subsequently.  
     
     
         20 . The process of  claim 19 , wherein said photo-irradiation is conducted by using ultraviolet ray whose wavelength is at most 380 nm.  
     
     
         21 . The process of  claim 19 , wherein said photo-irradiation is conducted out by using ultraviolet ray whose wavelength is at most 300 nm.  
     
     
         22 . The process of  claim 19 , wherein said photo-irradiation is conducted out for 0.1 to 600 minutes.