Dye for an intraocular lens and an intraocular lens using it

Abstract

The present invention provides lenses for eyes having visible light transmission properties near to those of human crystalline lenses, particularly coloring techniques effective for soft lenses for eyes. The present invention is a yellow dye capable of chemical bonding to a silicone which is a material of the intraocular lens or capable of copolymerizing with a radical polymerizable monomer which is a material of the intraocular lens.

1 . A dye for an intraocular lens having the following formula [I] or [II], wherein formula [I] is represented by the general formula:  
       
         
           
           
               
               
           
         
         wherein R 1  is linear or branched alkyl of C 1 -C 10  or phenyl; when R 1  is phenyl, one or more hydrogens of its aromatic ring may be substituted by linear or branched alkyl of C 1 -C 10 , linear or branched alkoxyl of C 1 -C 10 , hydroxy, amino, sulfo, nitro, halogen, carboxy, —C(═O)—O—R 4  or —C(═O)—NH—R 4 , wherein R 4  is linear or branched alkyl of C 1 -C 10 ,  
         R 2  is linear or branched alkyl of C 1 -C 10 , amino or phenyl; when R 2  is amino, one or both hydrogens thereof may be substituted by linear or branched alkyl of C 1 -C 10 ; or when R 2  is phenyl, one or more hydrogens of its aromatic ring may be substituted by linear or branched alkyl of C 1 -C 10 , linear or branched alkoxyl of C 1 -C 10 , hydroxy, amino, sulfo, nitro, halogen, carboxy, —C(═O)—O—R 4 , C(═O)—NH—R 4 , wherein R 4  is linear or branched alkyl of C 1 -C 10 ,  
         R 3  is phenyl or naphthyl, one or more hydrogens thereof are linear or branched alkyl of C 1 -C 10 , linear or branched alkoxyl of C 1 -C 10 , hydroxy, amino, sulfo, nitro, halogen, carboxy, —C(═O)—O—R 4 , —C(═O)—NH—R 4 , wherein R 4  is linear or branched alkyl of C 1 -C 10 , and  
         in formula [I], at least one hydrogen of the aromatic ring constituted in R 1 , R 2  or R 3  is substituted by any of CH 2 ═CH—(CH 2 ) m —, CH 2 ═CH—(CH 2 ) m —X 1 —(CH 2 ) n —, CH 2 ═C(R 5 )—(CH 2 ) m —X 1 —C(═O)—(CH 2 ) n —, CH 2 ═C(R 5 )—(CH 2 ) m —C(═O)—X 1 —(CH 2 ) n —, {CH 2 ═C(R 5 )—(CH 2 ) m —} 2 N— (CH 2 ) n —, or {CH 2 ═C(R 5 )—(CH 2 ) m —} 2 N—C(═O)—(CH 2 ) n —; wherein X 1  is —O— or —NR 6 —, R 5  and R 6  are independently hydrogen, or linear or branched alkyl of C 1 ˜C 10 , and m and n are independently integers of  0  to  10 , and wherein formula [II] is represented by the general formula:  
         
           
             
             
                 
                 
             
           
         
         wherein R 11 , R 12 , R 13  R 14 , R 15  R 16  R 17  R 18  R 19 , and R 20  are independently selected from hydrogen, hydroxy, halogen, or linear or branched alkyl of C 1 -C 10 , and at least one of them is a substituted group represented by:  
         
           
             
             
                 
                 
             
           
         
         wherein R 21  and R 22  are independently hydrogen or methyl, R 23  is hydrogen or linear or branched alkyl of C 1 ˜C 10 , X 11 , X 12  and X 13 , independently, have covalent bonds, or linear or branched bivalent spacer groups, or —(CH 2 ) m —O—(CH 2 ) n —, wherein m and n are independently integers of  0  to  10 .  
       
     
     
         2 - 33 . (canceled)  
     
     
         34 . The dye according to  claim 1 , wherein the formula [I] has a constitution of an enol type or a keto type.  
     
     
         35 . The dye according to  claim 1 , wherein the formula [I] comprises the compounds 4-(4-acryloyloxyphenyl)azo-3-methyl-1-phenyl-5-pyrazolone, 4-(4-methacryloylphenyl)azo-3-methyl-1 phenyl-5-pyrazolone, 4-(4-methacryloyloxyphenyl)azo-3-methyl-1-phenyl-5-pyrazolone, 3-methyl-1-phenyl-4-(4-vinylphenyl)azo-5-pyrazolone, 1-(4-tert-butylphenyl)-3-methyl-4-(4-vinylphenyl)azo-5-pyrazolone, 4-(4-allylphenyl)azo-3-methyl-1-phenyl-5-pyrazolone, 4-(4-hydroxy-3-allylphenyl)azo-3-methyl-1-phenyl-5-pyrazolone, 4-allyloxyphenylazo-3-methyl-1-phenyl-5-pyrazolone, 4-(4-allyloxymethylphenyl)azo-3-methyl-1-phenyl-5-pyrazolone, 4-allyloxycarbonylphenylazo-3-methyl-1-phenyl-5-pyrazolone, 4-(4-allyloxycarbonylphenyl)azo-3-methyl-1-phenyl-5-pyrazolone, 4-(4-allylphenyl)azo-1-(4-tert-butylphenyl)-3-methyl-5-pyrazolone, 4-(4-allyloxyphenyl)azo-1-(4-tert-butylphenyl)-3-methyl-5-pyrazolone, 4-(4-allyloxycarbonylphenyl)azo-1-(4-tert-butylphenyl)-3-methyl-5-pyrazolone, 4-(4-acryloylphenyl)azo-1-(4-tert-butylphenyl)-3-methyl-5-pyrazolone, 4-(4-acryloyloxyphenyl)azo-1-(4-tert-butylphenyl)-3-methyl-5-pyrazolone, 1-(4-tert-butylphenyl)-4-(4-methacryloylphenyl)azo-3-methyl-5-pyrazolone, 1-(4-tert-butylphenyl)-4-(4-methacryloyloxyphenyl)azo-3-methyl-5-pyrazolone, 1-(4-allylphenyl)-3-methyl-4-phenylazo-5-pyrazolone, 1-(4-allylphenyl)-4-(4-tert-butylphenyl)azo-3-methyl-5-pyrazolone, 1-(4-allyloxyphenyl)-4-(4-tert-butylphenyl)azo-3-methyl-5-pyrazolone, 1-(4-allyloxycarbonylphenyl)-4-(4-tert-butylphenyl)azo-3-methyl-5-pyrazolone, 1-(4-allylphenyl)-4-(2-tert-butylphenyl)azo-3-methyl-5-pyrazolone, 1-(4-allylphenyl)-4-(4-sec-butylphenyl)azo-3-methyl-5-pyrazolone, 1-(4-allylphenyl)-4-(2-tert-butylphenyl)azo-3-methyl-5-pyrazolone, 1-(4-allylphenyl)-4-(2-sec-butylphenyl)azo-3-methyl-5-pyrazolone, 1-(4-acryloylphenyl)-3-methyl-4-phenylazo-5-pyrazolone, 4-(3-methyl-1-phenyl-5-pyrazolone-4-yl)azoallylanilido, 4-(3-methyl-1-phenyl-5-pyrazolone-4-yl)azoallylanilido, N-allyl-4-(3-methyl-1-phenyl-5-pyrazolone-4-yl)azobenzamide, N,N-diallyl-4-(3-methyl-1-phenyl-5-pyrazolone-4-yl)azobenzamide and the like.  
     
     
         36 . The dye according to  claim 1 , wherein the formula [II] comprises the compounds N,N-diallyl-4-aminoazobenzene, N-allyl-4-aminoazobenzene, 4-allyloxymethylazobenzene, N,N-dimethacryl-4-aminoazobenzene, N-methacryl-4-aminoazobenzene, 4-methacryloxymethylazobenzene, N,N-diallyl-4-(2-aminoethyl)azobenzene, N,N-diallyl-4-aminomethylazobenzene, N-allyl-4-(2-aminoethyl)azobenzene, N-allyl-4-aminomethylazobenzene, N,N-diethyl-4-amino-3-allylazobenzene, N,N-dimethyl-4-amino-3-allylazobenzene, N,N-diethyl-4-amino-4′-allylazobenzene, N,N-dimethyl-4-amino-4′-allylazobenzene and the like, but these are not limited to the above compounds.  
     
     
         37 . The dye according to  claim 1 , wherein the formula [I] comprises the compounds  
       
         
           
           
               
               
           
         
       
     
     
         38 . The dye according to  claim 1 , wherein the formula [II] comprises the compounds  
       
         
           
           
               
               
           
         
       
     
     
         39 . The dye according to  claim 1 , wherein the dye has a maximum absorbance of about 350-450 nm.  
     
     
         40 . A dye for an intraocular lens having the following formula [I] or [II], wherein formula [I] is represented by the general formula:  
       
         
           
           
               
               
           
         
         wherein R 1  is linear or branched alkyl of C 1 -C 10  or phenyl; when R 1  is phenyl, one or more hydrogens of its aromatic ring may be substituted by linear or branched alkyl of C 1 -C 10 , linear or branched alkoxyl of C 1 -C 10 , hydroxy, amino, sulfo, nitro, halogen, carboxy, —C(═O)—O—R 4  or —C(═O)—NH—R 4 , wherein R 4  is linear or branched alkyl of C 1 -C 10 ,  
         R 2  is linear or branched alkyl of C 1 -C 10 , or phenyl; when R 1  is phenyl, one or more hydrogens of its aromatic ring may be substituted by linear or branched alkyl of C 1 -C 10 , linear or branched alkoxyl of C 1 -C 10 , hydroxy, amino, sulfo, nitro, halogen, carboxy, —C(═O)—O—R 4 , —C(═O)—NH—R 4 , wherein R 4  is linear or branched alkyl of C 1 -C 10 ,  
         R 3  is phenyl or naphthyl, one or more hydrogens thereof are linear or branched alkyl of C 1 -C 10 , linear or branched alkoxyl of C 1 -C 10 , hydroxy, amino, sulfo, nitro, halogen, carboxy, —C(═O)—O—R 4 , —C(═O)—NH—R 4 , wherein R 4  is linear or branched alkyl of C 1 -C 10 , and  
         in formula [I], at least one hydrogen of the aromatic ring constituted in R 1 , R 2  or R 3  is substituted by any of CH 2 ═CH—(CH 2 ) m —, CH 2 ═CH—(CH 2 ) m —X 1 —(CH 2 ) n —, CH 2 ═C(R 5 )—(CH 2 ) m —X 1 —C(═O)— (CH 2 ) n —, CH 2 ═C(R 5 )—(CH 2 ) m —C(═O)—X 1 —(CH 2 ) n —, {CH 2 ═C(R 5 )—(CH 2 ) m -} 2 N-(CH 2 ) n —, or {CH 2 ═C(R 5 )—(CH 2 ) m —} 2 N—C(═O)—(CH 2 ) n —;  
         wherein X 1  is —O— or —NR 6 —, R 5  and R 6  are independently hydrogen, or linear or branched alkyl of C 1 -C 10 , and m and n are independently integers of 0 to 10, and wherein formula [II] is represented by the general formula:  
         
           
             
             
                 
                 
             
           
         
         wherein R 11 , R 12 , R 13 , R 14 , R 15 R 16 , R 17 , R 18 , R 19 , and R 20  are independently selected from hydrogen, hydroxy, halogen, or linear or branched alkyl of C 1 -C 10 , and at least one of them is a substituted group represented by:  
         
           
             
             
                 
                 
             
           
         
         wherein R 21  and R 22  are independently hydrogen or methyl, R 23  is hydrogen or linear or branched alkyl of C 1 -C 10 , X 11 , X 12  and X 13 , independently, are —(CH 2 ) n — or —(CH 2 ) m —O—(CH 2 ) n —, wherein m and n are independently integers of 0 to 10.  
       
     
     
         41 . An intraocular lens using the material described in  claim 1 .  
     
     
         42 . An intraocular lens using the material described in  claim 34 .  
     
     
         43 . An intraocular lens using the material described in  claim 35 .  
     
     
         44 . An intraocular lens using the material described in  claim 36 .  
     
     
         45 . An intraocular lens using the material described in  claim 37 .  
     
     
         46 . An intraocular lens using the material described in  claim 38 .  
     
     
         47 . An intraocular lens using the material described in  claim 39.