Photoreactive monomers

Abstract

Photoreactive monomer which has (i) at least one free-radically polymerizable C—C double bond, (ii) at least one hydrophilic group selected from an ethylene glycol group and a polyethylene glycol group having at least 2 ethylene glycol units and (iii) at least one photoreactive group, the photoreactive group being a photoenolizable carbonyl group, and also a method for preparing the photoreactive monomers.

1 - 8 : (canceled) 
     
     
         9 . A method for preparing a compound represented formula (I): 
       
         
           
           
               
               
           
         
         wherein
 n is an integer from 0 to 29, and 
 R is hydrogen or methyl, comprising: 
 reacting an ethylene glycol having the number of ethylene glycol groups corresponding to n=0 to 29 with p-toluenesulfonyl chloride; 
 reacting with a compound which comprises a photoreactive group represented by the formula: 
 
       
       
         
           
           
               
               
           
         
         wherein
 R 1  is hydrogen or an organic residue, 
 R 2  is hydrogen or an organic residue, and 
 R 3  represents one or more substituents on the aromatic ring which are identical or different from one another and are optionally linked to one another via one or more ring systems; and 
 reacting with a (meth)acryloyl halide. 
 
       
     
     
         10 . The method of  claim 9 , wherein n is an integer from 3 to 19. 
     
     
         11 . The method of  claim 9 , wherein the (meth)acryloyl halide is a (meth)acryloyl chloride. 
     
     
         12 . The method of  claim 9 , wherein R is hydrogen. 
     
     
         13 . The method of  claim 9 , wherein R is methyl. 
     
     
         14 . The method of  claim 9 , wherein R 1  is hydrogen. 
     
     
         15 . The method of  claim 9 , wherein R 1  is an organic residue and wherein the organic residue is an alkyl group or an aryl group. 
     
     
         16 . The method of  claim 9 , wherein R 1  is an organic residue and wherein the organic residue is a C 1 -C 20  alkyl group or an aryl group having a mono- to trinuclear aromatic ring system containing 6 to 14 carbon ring members. 
     
     
         17 . A method for preparing a compound represented formula (II): 
       
         
           
           
               
               
           
         
         wherein
 n is an integer from 0 to 19, and 
 R is hydrogen or methyl, comprising: 
 reacting a poly(ethylene glycol) (meth)acrylate having the number of ethylene glycol groups corresponding to n=0 to 19 with p-toluenesulfonyl chloride; and 
 reacting with a compound which comprises a photoreactive group represented by the formula: 
 
       
       
         
           
           
               
               
           
         
         wherein
 R 1  is hydrogen or an organic residue, 
 R 2  is hydrogen or an organic residue, and 
 R 3  represents one or more substituents on the aromatic ring which are identical or different from one another and are optionally linked to one another via one or more ring sy stems. 
 
       
     
     
         18 . The method of  claim 17 , wherein n is an integer from 1 to 9. 
     
     
         19 . The method of  claim 17 , wherein R is hydrogen. 
     
     
         20 . The method of  claim 17 , wherein R is methyl. 
     
     
         21 . The method of  claim 17 , wherein R 1  is hydrogen. 
     
     
         22 . The method of  claim 17 , wherein R 1  is an organic residue and wherein the organic residue is an alkyl group or an aryl group. 
     
     
         23 . The method of  claim 17 , wherein R 1  is an organic residue and wherein the organic residue is a C 1 -C 20  alkyl group or an aryl group having a mono- to trinuclear aromatic ring system containing 6 to 14 carbon ring members. 
     
     
         24 . The method of  claim 17 , wherein R 2  is hydrogen. 
     
     
         25 . The method of  claim 17 , wherein R 2  is an organic residue and wherein the organic residue is an alkyl group or an aryl group. 
     
     
         26 . The method of  claim 17 , wherein R 3  is hydrogen. 
     
     
         27 . The method of  claim 17 , wherein R 3  is hydrogen, an alkyl group or an aryl group. 
     
     
         28 . The method of  claim 17 , wherein R 3  is hydrogen, a C 1 -C 20  alkyl group or an aryl group having a mono- to trinuclear aromatic ring system containing 6 to 14 carbon ring members.