Modified polyvinyl alcohol resins and adhesive, polarizer, and display device containing the same

Abstract

Provided are a modified polyvinyl alcohol-based resin with an acrylic group introduced thereto and including a hydroxyl group formed during the introduction of the acrylic group, an adhesive including the modified polyvinyl alcohol-based resin having excellent adhesion, humidity resistance, and water resistance, an adhesive including a polyvinyl alcohol-based resin, and a compound having an epoxy group, and an acrylic group, a polarizing plate and an image display device including the adhesive. The adhesive for a polarizing plate according to an embodiment of the present invention has excellent adhesion, humidity resistance, and water resistance as well as having excellent solubility with respect to water and an increase in adhesion while physical properties of a typical polyvinyl alcohol-based resin are maintained.

1 . A modified polyvinyl alcohol-based resin with an acrylic group introduced thereto and comprising a hydroxyl group formed during the introduction of the acrylic group. 
     
     
         2 . The modified polyvinyl alcohol-based resin of  claim 1 , wherein the acrylic group is introduced in a range of about 0.1 mol % to about 50 mol %. 
     
     
         3 . The modified polyvinyl alcohol-based resin of  claim 1 , wherein the modified polyvinyl alcohol-based resin is obtained by performing a reaction between a polyvinyl alcohol-based resin and a compound having epoxy and acrylic groups. 
     
     
         4 . The modified polyvinyl alcohol-based resin of  claim 1 , wherein the modified polyvinyl alcohol-based resin comprises a repeating unit of the following Chemical Formula A and at least one repeating unit of the following Chemical Formulas B1, B2, and B3. 
       
         
           
           
               
               
           
         
       
       (where n is an integer between about 490 and about 1700, m is an integer between about 10 and about 900, n+m is an integer between about 500 and about 1800, R 1  is substituted or unsubstituted C 1 -C 20  alkandiyl, a substituted or unsubstituted 1- to 7-membered cyclic group, a substituted or unsubstituted 1- to 7-membered heterocyclic group including a heteroatom selected from the group consisting of N, S, or O, a substituted or unsubstituted C 6 -C 14  aromatic group, or a substituted or unsubstituted 1- to 7-membered heteroaromatic group including at least one heteroatom selected from the group consisting of N, S, or O, R 2  is a substituted or unsubstituted C 1 -C 20  alkyl group, a substituted or unsubstituted 1- to 7-membered cyclic group, a substituted or unsubstituted 1- to 7-membered heterocyclic group including at least one heteroatom selected from the group consisting of N, S, or O, a substituted or unsubstituted C 6 -C 14  aromatic group, or a substituted or unsubstituted 1- to 7-membered heteroaromatic group including at least one heteroatom selected from the group consisting of N, S, or O, and when R 1  and R 2  are substituted with a substituent, the substituent is a C 1 -C 20  alkyl group, a halogen atom selected from the group consisting of F, Cl, Br, or I, a 1- to 7-membered cyclic group, a 1- to 7-membered heterocyclic group including at least one heteroatom selected from the group consisting of N, S, or O, a C 6 -C 14  aromatic group, or a 1- to 7-membered heteroaromatic group including at least one heteroatom selected from the group consisting of N, S, or O) 
     
     
         5 . The modified polyvinyl alcohol-based resin of  claim 4 , wherein the modified polyvinyl alcohol-based resin further comprises a repeating unit of the following Chemical Formula C, a sum of the number (n) of the repeating unit of Chemical Formula A and the number (l) of the repeating unit of Chemical Formula C is an integer between about 490 and about 1700, the number (l) of the repeating unit of Chemical Formula C in the sum of n and l is an integer between about 1 and about 80, the number (m) of the one repeating unit of Chemical Formulas B1, B2, and B3 is an integer between about 10 and about 900, and a sum of n, m, and l is an integer between about 500 and about 1800. 
       
         
           
           
               
               
           
         
       
       (where 1 is an integer between about 1 and 80, and R 3  is an acetoacetyl group, a carboxylic acid group, an acrylic group, or a urethane group) 
     
     
         6 . The modified polyvinyl alcohol-based resin of  claim 3 , wherein an average degree of polymerization of the polyvinyl alcohol-based resin is in a range of about 500 and about 1800. 
     
     
         7 . The modified polyvinyl alcohol-based resin of  claim 3 , wherein the compound having epoxy and acrylic groups is represented as the following Chemical Formula 1 or Chemical Formula 2. 
       
         
           
           
               
               
           
         
       
       (where R 1  is substituted or unsubstituted C 1 -C 20  alkandiyl, a substituted or unsubstituted 1- to 7-membered cyclic group, a substituted or unsubstituted 1- to 7-membered heterocyclic group including a heteroatom selected from the group consisting of N, S, or O, a substituted or unsubstituted C 6 -C 14  aromatic group, or a substituted or unsubstituted 1- to 7-membered heteroaromatic group including at least one heteroatom selected from the group consisting of N, S, or O, R 2  is a substituted or unsubstituted C 1 -C 20  alkyl group, a substituted or unsubstituted 1- to 7-membered cyclic group, a substituted or unsubstituted 1- to 7-membered heterocyclic group including at least one heteroatom selected from the group consisting of N, S, or O, a substituted or unsubstituted C 6 -C 14  aromatic group, or a substituted or unsubstituted 1- to 7-membered heteroaromatic group including at least one heteroatom selected from the group consisting of N, S, or O, and when R 1  and R 2  are substituted with a substituent, the substituent is a C 1 -C 20  alkyl group, a halogen atom selected from the group consisting of F, Cl, Br, or I, a 1- to 7-membered cyclic group, a 1- to 7-membered heterocyclic group including at least one heteroatom selected from the group consisting of N, S, or O, a C 6 -C 14  aromatic group, or a 1- to 7-membered heteroaromatic group including at least one heteroatom selected from the group consisting of N, S, or O) 
     
     
         8 . An adhesive for a polarizing plate comprising the modified polyvinyl alcohol-based resin of  claim 1 . 
     
     
         9 . An adhesive for a polarizing plate comprising about 100 parts by weight of the polyvinyl alcohol-based resin and about 0.001 to 10 parts by weight of the compound having epoxy and acrylic groups. 
     
     
         10 . The adhesive for a polarizing plate of  claim 9 , wherein an average degree of polymerization of the polyvinyl alcohol-based resin is in a range of about 500 and about 1800. 
     
     
         11 . The adhesive for a polarizing plate of  claim 9 , wherein the compound having epoxy and acrylic groups is represented as the following Chemical Formula 1 or Chemical Formula 2. 
       
         
           
           
               
               
           
         
       
       (where R 1  is substituted or unsubstituted C 1 -C 20  alkandiyl, a substituted or unsubstituted 1- to 7-membered cyclic group, a substituted or unsubstituted 1- to 7-membered heterocyclic group including a heteroatom selected from the group consisting of N, S, or O, a substituted or unsubstituted C 6 -C 14  aromatic group, or a substituted or unsubstituted 1- to 7-membered heteroaromatic group including at least one heteroatom selected from the group consisting of N, S, or O, R 2  is a substituted or unsubstituted C 1 -C 20  alkyl group, a substituted or unsubstituted 1 to 7-membered cyclic group, a substituted or unsubstituted 1- to 7-membered heterocyclic group including at least one heteroatom selected from the group consisting of N, S, or O, a substituted or unsubstituted C 6 -C 14  aromatic group, or a substituted or unsubstituted 1- to 7-membered heteroaromatic group including at least one heteroatom selected from the group consisting of N, S, or O, and when R 1  and R 2  are substituted with a substituent, the substituent is a C 1 -C 20  alkyl group, a halogen atom selected from the group consisting of F, Cl, Br, or I, a 1- to 7-membered cyclic group, a 1- to 7-membered heterocyclic group including at least one heteroatom selected from the group consisting of N, S, or O, a C 6 -C 14  aromatic group, or a 1- to 7-membered heteroaromatic group including at least one heteroatom selected from the group consisting of N, S, or O) 
     
     
         12 . The adhesive for a polarizing plate of  claim 8 , wherein the adhesive for a polarizing plate further comprises an initiator selected from the group consisting of 2,2′-azo-bis(isobutyronitrile) (AIBN)-based and persulfate-based water-soluble initiators. 
     
     
         13 . The adhesive for a polarizing plate of  claim 12 , wherein the initiator is added to a maximum of about 10 wt %. 
     
     
         14 . A polarizing plate comprising a polarizer and a protective film adhered to each other with the adhesive for a polarizing plate of  claim 8 . 
     
     
         15 . A display device comprising the polarizing plate of  claim 14 . 
     
     
         16 . The adhesive for a polarizing plate of  claim 9 , wherein the adhesive for a polarizing plate further comprises an initiator selected from the group consisting of 2,2′-azo-bis(isobutyronitrile) (AIBN)-based and persulfate-based water-soluble initiators. 
     
     
         17 . The adhesive for a polarizing plate of  claim 16 , wherein the initiator is added to a maximum of about 10 wt %. 
     
     
         18 . A polarizing plate comprising a polarizer and a protective film adhered to each other with the adhesive for a polarizing plate of  claim 9 . 
     
     
         19 . A display device comprising the polarizing plate of  claim 18 .