Macroinitiator containing hydrophobic segment

Abstract

The present invention relates to macroinitiators comprising at least one hydrophobic segments in a molecule, wherein a molecular weight of the hydrophobic segment is 300 to 1800. The present invention further relates to block copolymers, wetting agent and polymeric materials having the block copolymers of the present invention associated with, which is suitable for medical devices, particularly for ophthalmic devices, including contact lenses, ophthalmic lenses, punctal plugs and artificial corneas.

1 . A macro initiator comprising one or two hydrophobic segments in a molecule, wherein a molecular weight of the hydrophobic segments is 300 to 1800. 
     
     
         2 . The macro initiator according to  claim 1 , wherein the hydrophobic segment is a segment made from polysiloxane. 
     
     
         3 . The macro initiator according to  claim 2 , expressed by formula (a0) or (a1). Formula: 
       
         
           
           
               
               
           
         
         (wherein in (a0) and (a1), R 1  is one type of group selected from an alkyl group or an alkoxy group; 
         R 2  is one type of group selected from (CH 2 ) n  and (CH 2 ) m —O(CH 2 ) n ; 
         m and n are independent, ranging from 1 to 16; a is from 4 to 19; b is from 1 to 6, and X is one type of group selected from O, NH, and S). 
       
     
     
         4 . A block copolymer comprising one hydrophobic segment and one hydrophilic segment, wherein a molecular weight of the hydrophobic segment is 300 to 1800. 
     
     
         5 . The block copolymer according to  claim 4 , wherein the hydrophobic segment is a segment made from polysiloxane. 
     
     
         6 . The block copolymer according to  claim 5 , expressed by formula (b1). Formula: 
       
         
           
           
               
               
           
         
         (wherein in (b1), R 1  is one type of group selected from an alkyl group or an alkoxy group; 
         R 2  is one type of group selected from (CH 2 ) n  and (CH 2 ) m —O(CH 2 ) n ; 
         m and n are independent, ranging from 1 to 16; a is from 4 to 19; b is from 1 to 6, c is from 1 to 10,000, X is one type of group selected from O, NH, and S; and R 3  and R 4  represent groups made of monomers with hydrophilicity wherein a monomer is expressed by general formula (n)). 
       
       
         
           
           
               
               
           
         
       
     
     
         7 . The block copolymer according to any one of  claims 1  through  6 , wherein a weight-average molecular weight is from approximately 10,000 to approximately 3,000,000. 
     
     
         8 . The block copolymer according to any one of  claims 4  through  7 , further comprising approximately 0.01 to approximately 5 weight % of a hydrophobic segment and approximately 95 to approximately 99.9 weight % of a hydrophilic segment. 
     
     
         9 . The block copolymer according to any one of  claims 4  through  8 , wherein the hydrophilic segment is made from a hydrophilic polymer selected from a group consisting of poly-N-vinyl-2-pyrrolidone, poly-N-vinyl-2-piperidone, poly-N-vinyl-2-caprolactum, poly-N-vinyl-3-methyl-2-caprolactum, poly-N-vinyl-3-methyl-2-piperidone, poly-N-vinyl-4-methyl-2-piperidone, poly-N-vinyl-4-methyl-2-caprolactum, poly-N-vinyl-3-ethyl-2-pyrrolidone, poly-N-vinyl-4,5-dimethyl-2-pyrrolidone, polyvinyl imidazole, poly-N—N-dimethyl acrylamide, poly-N-vinyl-N-methyl acetamide, polyvinyl alcohol, polyacrylic acid, polymethacrylic acid, and poly(hydroxyethyl methacrylate), as well as blends and copolymers thereof. 
     
     
         10 . A medical material comprising a block copolymer according to any one of  claims 4  through  9 . 
     
     
         11 . A manufacturing method for a block copolymer according to any one of  claims 4  through  9 , wherein a monomer that can form a hydrophilic segment is polymerized using a macro initiator according to any one of  claims 1  through  3 . 
     
     
         12 . A contact lens wetting agent, comprising a block copolymer containing one or more hydrophobic segments and one or more hydrophilic segments, wherein a molecular weight of the hydrophobic segment is 300 to 1800. 
     
     
         13 . The contact lens wetting agent according to  claim 12 , wherein the block copolymer is a block copolymer expressed by formula (b1) or (b2) below. 
       
         
           
           
               
               
           
         
         (wherein in (b1) and (b2), R 1  is one type of group selected from an alkyl group or an alkoxy group; 
         R 2  is selected from the group consisting of (CH 2 ) n  or (CH 2 ) m —O(CH 2 ) n ; 
         m and n are independent, ranging from 1 to 16; a is from 4 to 19; b is from 1 to 6, c is from 1 to 10,000, X is one type of group selected from O, NH, and S; and R 3  and R 4  represent groups made of monomers with hydrophilicity wherein a monomer is expressed by general formula (n)). 
       
       
         
           
           
               
               
           
         
       
     
     
         14 . The contact lens wetting agent according to  claim 12  or  13 , wherein a weight-average molecular weight of the block copolymer is from approximately 10,000 to approximately 3,000,000. 
     
     
         15 . The contact lens wetting agent according to any one of  claims 12  through  14 , wherein the block copolymer contains approximately 0.01 to approximately 5 weight % of a hydrophobic segment and approximately 95 to approximately 99.9 weight % of a hydrophilic segment. 
     
     
         16 . The contact lens wetting agent according to any one of  claims 12  through  15 , wherein the hydrophilic segment is a segment made from a hydrophilic polymer selected from the group consisting of poly-N-vinyl-2-pyrrolidone, poly-N-vinyl-2-piperidone, poly-N-vinyl-2-caprolactum, poly-N-vinyl-3-methyl-2-caprolactum, poly-N-vinyl-3-methyl-2-piperidone, poly-N-vinyl-4-methyl-2-piperidone, poly-N-vinyl-4-methyl-2-caprolactum, poly-N-vinyl-3-ethyl-2-pyrrolidone, poly-N-vinyl-4,5-dimethyl-2-pyrrolidone, polyvinyl imidazole, poly-N—N-dimethyl acrylamide, poly-N-vinyl-N-methyl acetamide, polyvinyl alcohol, polyacrylic acid, polymethacrylic acid, and poly(hydroxyethyl methacrylate), as well as blends and copolymers thereof. 
     
     
         17 . A contact lens wetting agent solution, comprising a contact lens wetting agent according to any one of  claims 12  through  16 . 
     
     
         18 . The contact lens wetting agent solution according to  claim 17 , wherein the contact lens wetting agent solution is a packaging solution or a storage solution. 
     
     
         19 . A medical material comprising silicone hydrogel and a block copolymer according to any one of  claims 4  through  9 . 
     
     
         20 . The medical material according to  claim 19 , comprising approximately 0.1 ppm to approximately 30% of the block copolymer. 
     
     
         21 . The medical material according to any one of  claims 18  through  20 , wherein a hydrophilic monomer that is used in the silicone hydrogel is selected from a group consisting of N,N-dimethyl acrylamide (DMA), 2-hydroxyethyl acrylate, glycerol methacrylate, 2-hydroxyethyl methacrylate amide, polyethylene glycol mono methacrylate, methacrylic acid, acrylic acid, N-vinyl pyrrolidone, N-vinyl-N-methyl acetamide, N-vinyl-N-ethyl acetamide, N-vinyl-N-ethyl form amide, N-vinyl formamide, N-2-hydroxyethyl vinyl carbamate, N-carboxy-beta-alanine N-vinylester, reactive polyethylene polyol, hydrophilic vinyl carbonate, vinyl carbamate monomer, hydrophilic oxazolone monomer, hydrophilic oxazoline monomer, and combinations thereof. 
     
     
         22 . The medical material according to any one of  claims 18  through  21 , wherein a silicone monomer that is used in the silicone hydrogel has a hydroxyl group. 
     
     
         23 . The medical material according to  claim 22 , wherein an amount of component derived from a silicone monomer that is used in the silicone hydrogel is approximately 5 to approximately 95 weight %.