Photosensitive amine generator, photocurable composition and photoreactive adhesive composition

Abstract

The invention provides compounds which can generate amine by irradiation with light and are excellent both in photodecomposability and in reactivity and compatibility with amine-curable compounds, and photo-setting compositions containing the compounds. The compounds are carbamoyloxyimino compounds represented by the structural formula (I); and the compositions each comprise one or more of the carbamoyloxyimino compounds and an amine-curable compound. In the formula (I), R1 is an n-valent organic group; R2 and R3 are each hydrogen or an aromatic or aliphatic group; and n is an integer of 1 or above.

1 . A photosensitive amine generator containing a carbamoyloxyimino group and represented by the structural formula 1  
       
         
           
           
               
               
           
         
       
       wherein R1 is an n-valent organic group; R2 and R3 are independently hydrogen, an aromatic group, or an aliphatic group; and n is an integer of 1 or larger.  
     
     
         2 . The photosensitive amine generator as recited in  claim 1 , wherein R1 in the structural formula 1 is the organic group represented by the structural formula 2  
       
         
           
           
               
               
           
         
       
       wherein R4 is an (m+n)-valent organic group; R5 is at least one selected from the group consisting of isocyanate, (meth)acryloyl and vinyl groups; if R5 exists in plurality, R5's may be identical to or different from each other; and m is a positive integer of 1 or larger.  
     
     
         3 . The photosensitive amine generator as recited in  claim 1  or  2 , wherein one of R2 and R3 in said structural formula 1 is hydrogen or an aliphatic group, and the other is an aromatic group.  
     
     
         4 . The photosensitive amine generator as recited in  claim 1 , wherein said R1 is an aromatic group.  
     
     
         5 . The photosensitive amine generator as recited in  claim 2  or  3 , wherein R4 in said structural formula 2 is an aromatic group.  
     
     
         6 . The photosensitive amine generator as recited in any one of claims  1 - 5 , wherein R2 and R3 are independently selected from the group consisting of hydrogen, a methyl group, phenyl group and a naphthyl group.  
     
     
         7 . A photosensitive amine generator characterized as comprising a polymer or oligomer made via copolymerization of a compound having a free-radically polymerizable group with a monomer having a (meth)acryloyl group and a carbamoyloxyimino group.  
     
     
         8 . A photocurable composition characterized as containing the photosensitive amine generator as recited in any one of claims  1 - 7  and an amine-curable compound.  
     
     
         9 . The photocurable composition as recited in  claim 8 , further containing a thioxanthone sensitizer.  
     
     
         10 . A photocurable composition characterized as containing: 
 A: an amine-curable compound; and    B: a photosensitive amine generator having a carbamoyloxyimino group.    
     
     
         11 . The photocurable composition as recited in  claim 10 , wherein said compound B having a carbamoyloxyimino group is a compound obtained by reacting an isocyanate group of a urethane prepolymer with an oxime compound.  
     
     
         12 . The photocurable composition as recited in  claim 10 , wherein said compound B having a carbamoyloxyimino group is a compound having a carbamoyloxyimino group and a functional group selected from an isocyanate group, an epoxy group and a free-radically polymerizable group.  
     
     
         13 . The photocurable composition as recited in any one of claims  10 - 12 , further containing a thioxanthone sensitizer.  
     
     
         14 . A photocurable composition characterized as containing: 
 A: an amine-curable compound;    B′: a photosensitive amine generator having a free-radically polymerizable group and a carbamoyloxyimino group; and    C: a free-radical photoinitiator.    
     
     
         15 . A photocurable composition characterized as containing: 
 A′: a urethane prepolymer; and    B: a photosensitive amine generator having a carbamoyloxyimino group.    
     
     
         16 . The photocurable composition as recited in  claim 15 , wherein said compound B having a carbamoyloxyimino group comprises a polymer or oligomer made via copolymerization of a compound having a free-radically polymerizable group with a monomer having a (meth)acryloyl group and a carbamoyloxyimino group.  
     
     
         17 . A photocurable composition characterized as containing: 
 A′: a urethane prepolymer;    B′: a photosensitive amine generator having a free-radically polymerizable group and a carbamoyloxyimino group; and    C′: a free-radical photoinitiator.    
     
     
         18 . The photocurable composition as recited in any one of claims  15 - 17 , further containing a thioxanthone sensitizer.  
     
     
         19 . A photoreactive adhesive composition characterized as comprising the photocurable composition as recited in any one of claims  8 - 18 .