Organosilicon compounds, production processes thereof, pressure-sensitive adhesive compositions containing the organosilicon compounds, self-adhesive polarizers and liquid crystal displays

Abstract

Organosilicon compounds are represented by the following formula: wherein R is a hydrolyzable group, R′ is an alkyl having 1 to 4 carbon atoms, A is an alkylene having 1 to 6 carbon atoms, X is O or S, Y is —NH— or S, L 1 and L 2 are C or N, Z and M are —NH—, O or S, R 1 to R 11 are H, alkyl having 1 to 6 carbon atoms, alkoxy or fluoroalkyl, or amino, m is 1 to 3, and n is 0 to 3. R 1 and R 2 or R 2 and R 3 may bonded together. R 5 and R 6 or R 9 and R 10 may directly bond together. R 4 and R 7 or R 8 and R 11 may form a ring skeleton. Their production processes, pressure-sensitive adhesive compositions, self-adhesive polarizers and LCDs are also disclosed.

1 . An organosilicon compound represented by the following formula (1): 
       
         
           
           
               
               
           
         
       
       wherein R is a hydrolyzable group, R′ is an alkyl group having 1 to 4 carbon atoms, A is a linear or branched alkylene group having 1 to 6 carbon atoms, X is an oxygen atom or sulfur atom, Y is —NH— or a sulfur atom, L 1  and L 2  are each independently a carbon atom or nitrogen atom, R 1  to R 3  are each independently a hydrogen atom, an alkyl, alkoxy or fluoroalkyl group having 1 to 6 carbon atoms, or an amino group, R 1  and R 2  or R 2  and R 3  may bond together to form a ring skeleton with the carbon atoms to which they are bonded and L 2 , m is an integer of 1 to 3, and n is an integer of 0 to 3. 
     
     
         2 . An organosilicon compound represented by the following formula (2): 
       
         
           
           
               
               
           
         
       
       wherein R is a hydrolyzable group, R′ is an alkyl group having 1 to 4 carbon atoms, A is a linear or branched alkylene group having 1 to 6 carbon atoms, X is an oxygen atom or sulfur atom, Z is —NH—, an oxygen atom or a sulfur atom, M is —NH—, an oxygen atom or a sulfur atom, R 4  to R 7  are each independently a hydrogen atom, an alkyl, alkoxy or fluoroalkyl group having 1 to 6 carbon atoms, or an amino group, R 5  and R 6  may directly bond together to form a double bond between the carbon atoms to which they are bonded, R 4  and R 7  may bond together to form an aliphatic or aromatic ring skeleton together with the carbon atoms to which they are bonded, m is an integer of 1 to 3, and n is an integer of 0 to 3. 
     
     
         3 . An organosilicon compound represented by the following formula (3): 
       
         
           
           
               
               
           
         
       
       wherein R is a hydrolyzable group, R′ is an alkyl group having 1 to 4 carbon atoms, A is a linear or branched alkylene group having 1 to 6 carbon atoms, X is an oxygen atom or sulfur atom, Z is —NH—, an oxygen atom or a sulfur atom, R 8  to R 11  are each independently a hydrogen atom, an alkyl, alkoxy or fluoroalkyl group having 1 to 6 carbon atoms, or an amino group, R 9  and R 10  may directly bond together to form a double bond between the carbon atoms to which they are bonded, R 8  and R 11  may bond together to form an aliphatic or aromatic ring skeleton together with the carbon atoms to which they are bonded, m is an integer of 1 to 3, and n is an integer of 0 to 3. 
     
     
         4 . A process for producing the organosilicon compound according to  claim 1 , which comprises reacting an iso(thio)cyanatosilane, which is represented by the following formula (4): 
       
         
           
           
               
               
           
         
       
       wherein R is a hydrolyzable group, R′ is an alkyl group having 1 to 4 carbon atoms, A is a linear or branched alkylene group having 1 to 6 carbon atoms, X is an oxygen atom or sulfur atom, and m is an integer of 1 to 3, with a heterocyclic compound represented by the following formula (5): 
       
         
           
           
               
               
           
         
       
       wherein Y is —NH— or a sulfur atom, L 1  and L 2  are each independently a carbon atom or nitrogen atom, R 1  to R 3  are each independently a hydrogen atom, an alkyl, alkoxy or fluoroalkyl group having 1 to 6 carbon atoms, or an amino group, R 1  and R 2  or R 2  and R 3  may bond together to form a ring skeleton with the carbon atoms to which they are bonded and L 2 , and n is an integer of 0 to 3. 
     
     
         5 . A process for producing the organosilicon compound according to  claim 2 , which comprises reacting an iso(thio)cyanatosilane, which is represented by the following formula (4): 
       
         
           
           
               
               
           
         
       
       wherein R is a hydrolyzable group, R′ is an alkyl group having 1 to 4 carbon atoms, A is a linear or branched alkylene group having 1 to 6 carbon atoms, X is an oxygen atom or sulfur atom, and m is an integer of 1 to 3, with a heterocyclic compound represented by the following formula (6): 
       
         
           
           
               
               
           
         
       
       wherein Z is —NH—, an oxygen atom or a sulfur atom, M is —NH—, an oxygen atom or a sulfur atom, R 4  to R 7  are each independently a hydrogen atom, an alkyl, alkoxy or fluoroalkyl group having 1 to 6 carbon atoms, or an amino group, R 5  and R 6  may directly bond together to form a double bond between the carbon atoms to which they are bonded, R 4  and R 7  may bond together to form an aliphatic or aromatic ring skeleton together with the carbon atoms to which they are bonded, and n is an integer of 0 to 3. 
     
     
         6 . A process for producing the organosilicon compound according to  claim 3 , which comprises reacting an iso(thio)cyanatosilane represented by the following formula (4): 
       
         
           
           
               
               
           
         
       
       wherein R is a hydrolyzable group, R′ is an alkyl group having 1 to 4 carbon atoms, A is a linear or branched alkylene group having 1 to 6 carbon atoms, X is an oxygen atom or sulfur atom, and m is an integer of 1 to 3, with a heterocyclic compound represented by the following formula (7): 
       
         
           
           
               
               
           
         
       
       wherein Z is —NH—, an oxygen atom or a sulfur atom, R 8  to R 11  are each independently a hydrogen atom, an alkyl, alkoxy or fluoroalkyl group having 1 to 6 carbon atoms, or an amino group, R 9  and R 10  may directly bond together to form a double bond between the carbon atoms to which they are bonded, R 8  and R 11  may directly bond together to form an aliphatic or aromatic ring skeleton together with the carbon atoms to which they are bonded, and n is an integer of 0 to 3. 
     
     
         7 . A pressure-sensitive adhesive composition comprising the organosilicon compound according to  claim 1 . 
     
     
         8 . The pressure-sensitive adhesive composition according to  claim 7 , comprising:
 (A) 100 parts by weight of a (meth)acrylic copolymer obtainable by copolymerizing (a) 90 to 99.9 parts by weight of a (meth)acrylate ester monomer having an alkyl group having 1 to 12 carbon atoms and (b) 0.1 to 10 parts by weight of at least one of a vinyl monomer and (meth)acrylic monomer each of which contains a crosslinkable functional group,   (B) 0.01 to 10 parts by weight of a polyfunctional crosslinking agent, and   (C) 0.01 to 9 parts by weight of the organosilicon compound according to any one of  claims 1  to  3 .   
     
     
         9 . The pressure-sensitive adhesive composition according to  claim 8 , wherein at least one of the vinyl monomer and (meth)acrylic monomer (b) is selected from a group consisting of 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, diethylene glycol mono(meth)acrylate, dipropylene glycol mono(meth)acrylate, (meth) acryloxypropyltrimethoxysilane, (meth)acryloxypropyltriethoxysilane, (meth) acryloxypropylmethyldimethoxysilane, (meth) acryloxypropylmethyldiethoxysilane, (meth)acryloxymethyltrimethoxysilane, (meth)acryloxymethyltriethoxysilane, (meth)acryloxymethylmethyldimethoxysilane, (meth)acryloxymethylmethyldiethoxysilane, (meth)acrylic acid, (meth)acrylic acid dimmer, itaconic acid, maleic acid, and maleic acid anhydride. 
     
     
         10 . The pressure-sensitive adhesive composition according to  claim 8 , wherein the polyfunctional crosslinking agent (B) is at least one crosslinking agent selected from a group consisting of isocyanate compounds, epoxy compounds, aziridine compounds and metal chelate compounds. 
     
     
         11 . The pressure-sensitive adhesive composition according to  claim 7  which is cured into a product having a crosslink density of 5 to 95 wt %. 
     
     
         12 . A self-adhesive polarizer comprising a polarizing film and a pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition according to  claim 7  and applied on at least one of opposite sides of the polarizing film. 
     
     
         13 . The self-adhesive polarizer according to  claim 12 , further comprising at least one layer selected from a group consisting of a protective layer, a reflective layer, a retardation plate, an optical view-angle compensation film, and a luminance enhancement film. 
     
     
         14 . A liquid crystal display comprising a liquid crystal cell composed of a pair of glass substrates and a liquid crystal sealed between the glass substrates and the self-adhesive polarizer according to  claim 12  bonded on at least one of opposite sides of the liquid crystal cell.