Photoactivable nitrogen bases

Abstract

Compounds of the Formula (I), (II) and (III) wherein Ar is for example phenylene, biphenylene or naphthylene, all of which are unsubstituted or substituted by C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, CN, OR 11 , SR 11 , CH2OR 11 , COOR 12 , CONR 12 R 13 or halogen; R 1 , R 2 , R 7 and R 8 independently of one another other are hydrogen or C 1 -C 6 -alkyl; R 3 and R 5 together and R 4 and R 6 together form a C 2 -C 6 -alkylene bridge which is unsubstituted or substituted by one or more C 1 -C 4 -alkyl; R 11 is hydrogen or C 1 -C 6 -alkyl; R 12 and R 13 independently of one another for example are hydrogen, phenyl, C 1 -C 18 -alkyl, C 1 -C 18 -alkyl which is interrupted by one or more O; n is 1-10; X is O, S or NR 10 ; A and A 1 are suitable linking groups; are suitable as photolatent bases.

1 .- 18 . (canceled) 
     
     
         19 . A photolatent base compound of the formula (Ib) 
       
         
           
           
               
               
           
         
         wherein 
         Ar is phenylene, biphenylene, naphthylene, anthrylene or anthraquinonylene all of which are unsubstituted or are substituted by one or more C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, CN, OR 11 , SR 11 , CH 2 OR 11 , COOR 12 , CONR 12 R 13  or halogen; 
         R 1  and R 2  independently of one another other are hydrogen or C 1 -C 6 -alkyl; 
         R 11  is hydrogen or C 1 -C 6 -alkyl; 
         R 12  and R 13  independently of one another are hydrogen, phenyl, C 1 -C 18 -alkyl, C 1 -C 18 -alkyl which is interrupted by one or more O, or R 12  and R 13  are 
       
       
         
           
           
               
               
           
         
       
       wherein R 3  and R 5  together form a C 2 -C 6 -alkylene bridge which is unsubstituted or substituted by one or more C 1 -C 4 -alkyl; R 4  and R 6  together form a C 2 -C 6 -alkylene bridge which is unsubstituted or substituted by one or more C 1 -C 4 -alkyl, and R 1 , R 2  and Ar are as defined above;
 n is 1; 
 X is O, S or NR 10 ; 
 A is hydrogen, C 1 -C 18 -alkyl which optionally is interrupted by one or more O or N(R 13 ) and which uninterrupted or interrupted C 1 -C 18 alkyl is unsubstituted or is substituted by one or more C 1 -C 8 -alkyl, C 1 -C 6 -hydroxyalkyl, CN, OR 11 , SR 11 , NR 12 R 13 , COOR 12 , OCOR 14  or halogen; or 
 A is a n-valent polyalkylene-imine, if X is NR 13 ; 
 or additionally one or more X-A denote X n   −  Y n+  or X n   −  n Y + , if X is O; 
 R 10  has one of the meanings as given for A; 
 Y is an n-valent cationic counter ion; and 
 R 14  is —CH═CH 2  or —C(CH 3 )═CH 2 . 
 
     
     
         20 . The photolatent base compound of the formula (Ib) according to  claim 19 , wherein
 X is O or NR 10 .   
     
     
         21 . The photolatent base compound of the formula (Ib) according to  claim 19 , wherein
 Ar is phenylene;   R 1  and R 2  independently of one another other are hydrogen;   R 11  is hydrogen or C 1 -C 6 -alkyl;   X is O;   A is C 1 -C 18 -alkyl which optionally is interrupted by one or more O and which uninterrupted or interrupted C 1 -C 18 alkyl is unsubstituted or is substituted by OR 11 .   
     
     
         22 . The photolatent base compound of the formula (Ib) according to  claim 19 , which is 4-(hexahydro-pyrrolo[1,2-a]pyrimidin-1-ylmethyl)-benzoic acid methyl ester: 
       
         
           
           
               
               
           
         
       
     
     
         23 . A composition comprising
 (A) at least one photolatent base compound of formula (Ib)   
       
         
           
           
               
               
           
         
         wherein 
         Ar is phenylene, biphenylene, naphthylene, anthrylene or anthraquinonylene all of which are unsubstituted or are substituted by one or more C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, CN, OR 11 , SR 11 , CH 2 OR 11 , COOR 12 , CONR 12 R 13  or halogen; 
         R 1 , and R 2  independently of one another other are hydrogen or C 1 -C 6 -alkyl; 
         R 11  is hydrogen or C 1 -C 6 -alkyl; 
         R 12  and R 13  independently of one another are hydrogen, phenyl, C 1 -C 18 -alkyl, C 1 -C 18 -alkyl which is interrupted by one or more O, or R 12  and R 13  are 
       
       
         
           
           
               
               
           
         
       
       wherein R 3  and R 5  together form a C 2 -C 6 -alkylene bridge which is unsubstituted or substituted by one or more C 1 -C 4 -alkyl; R 4  and R 6  together form a C 2 -C 6 -alkylene bridge which is unsubstituted or substituted by one or more C 1 -C 4 -alkyl, and R 1 , R 2  and Ar are as defined above;
 n is 1; 
 X is O, S or NR 10 ; 
 A is hydrogen, C 1 -C 18 -alkyl which optionally is interrupted by one or more O or N(R 13 ) and which uninterrupted or interrupted C 1 -C 18 alkyl is unsubstituted or is substituted by one or more C 1 -C 8 -alkyl, C 1 -C 6 -hydroxyalkyl, CN, OR 11 , SR 11 , NR 12 R 13 , COOR 12 , OCOR 14  or halogen; or 
 A is a n-valent polyalkylene-imine, if X is NR 13 ; 
 or additionally one or more X-A denote X n   −  Y n+  or X n   −  n Y + , if X is O; 
 R 10  has one of the meanings as given for A; 
 Y is an n-valent cationic counter ion; and 
 R 14  is —CH═CH 2  or —C(CH 3 )═CH 2 ; and 
 (B) at least one organic compound which is capable of a base-catalysed addition, condensation or substitution reaction or which is converted into a different form by a base-catalysed reaction. 
 
     
     
         24 . The composition according to  claim 23 , wherein component (B) is an organic material which is polymerized or crosslinked by a base-catalyzed reaction. 
     
     
         25 . The composition according to  claim 23 , wherein component (B) is one of the following systems:
 a) acrylic copolymers with alkoxysilane and/or alkoxysiloxane side groups;   b) two-component systems comprising hydroxyl-containing polyacrylates, polyesters and/or polyethers and aliphatic or aromatic polyisocyanates;   c) two-component systems comprising functional polyacrylates and polyepoxide, the polyacrylate containing thiol, amino, carboxyl and/or anhydride groups;   d) two-component systems comprising fluorine-modified or silicone-modified, hydroxyl-containing polyacrylates, polyesters and/or polyethers and aliphatic or aromatic polyisocyanates;   e) two-component systems comprising (poly)ketimines and aliphatic or aromatic polyisocyanates;   f) two-component systems comprising (poly)ketimines and unsaturated acrylic resins or acetoacetate resins or methyl α-acrylamidomethylglycolate;   h) two-component systems comprising (poly)oxazolidines and polyacrylates containing anhydride groups or unsaturated acrylic resins or polyisocyanates;   i) two-component systems comprising epoxy-functional polyacrylates and carboxyl-containing or amino-containing polyacrylates;   l) polymers based on allyl glycidyl ether;   m) two-component systems comprising a (poly)alcohol and/or polythiol and a (poly)isocyanate;   n) two-component systems comprising an α,β-ethylenically unsaturated carbonyl compound and a polymer containing activated CH 2  groups;   o) two-component systems comprising a polymer containing activated CH 2  groups, the activated CH 2  groups being present either in the main chain or in the side chain or in both, or a polymer containing activated CH 2  groups such as (poly)acetoacetates and (poly)cyanoacetates, and a polyaldehyde crosslinker;   p) two-component or one-component systems comprising blocked isocyanates and a hydrogen donor;   q) thiol Michael systems.   
     
     
         26 . The composition according to  claim 23 , wherein component (B) is an epoxy resin or a mixture of different epoxy resins. 
     
     
         27 . The composition according to  claim 23 , wherein component (A) is present in an amount of from 0.01 to 20% by weight, based on component (B). 
     
     
         28 . The composition according to  claim 27 , wherein component (A) is present in an amount of from 0.01 to 10% by weight, based on component (B). 
     
     
         29 . The composition according to  claim 23 , comprising in addition to components (A) and (B) a sensitizer (C). 
     
     
         30 . The composition according to  claim 29 , wherein the sensitizer (C) is selected from the group consisting of benzophenone and benzophenone derivatives.