Novel bis(formylphenyl) compound and novel polynuclear polyphenol compound derived from the same

Abstract

A bis(formylphenyl) compound expressed by general formula (1) is manufactured by, for example, using a corresponding bis(hydroxy-formylphenyl) compound as the direct material and causing it to react with a halogenated alkoxycarbonyl hydrocarbon in the presence of a base according to a known phenylether manufacturing method.

1 . A bis(formylphenyl) compound expressed by general formula (1) below: 
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  each independently represent an alkyl group with 1 to 8 carbon atoms or alkoxyl group with 1 to 8 carbon atoms, R 3  is a single-ring or condensed-ring aromatic hydrocarbon group with 6 to 15 carbon atoms or aliphatic saturated hydrocarbon group with 1 to 8 carbon atoms that may have a single-ring or condensed-ring aromatic hydrocarbon group with 6 to 15 carbon atoms, R 4  is a hydrogen atom or alkyl group with 1 to 6 carbon atoms, R 5  and R 6  may be the same or different and each represent a bivalent aliphatic saturated hydrocarbon group with 1 to 8 carbon atoms, m is an integer of 0 or 1 to 3, n is an integer of 0 or 1 to 3, and k is an integer of 1 to 3, but if k is 2 or greater, then R 6 , R 1  and n in each phenyl group may all be the same or different. 
       
     
     
         2 . A polynuclear polyphenol compound expressed by general formula (2) below: 
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  each independently represent an alkyl group with 1 to 8 carbon atoms or alkoxyl group with 1 to 8 carbon atoms, R 3  is a single-ring or condensed-ring aromatic hydrocarbon group with 6 to 15 carbon atoms or aliphatic saturated hydrocarbon group with 1 to 8 carbon atoms that may have a single-ring or condensed-ring aromatic hydrocarbon group with 6 to 15 carbon atoms, R 4  is a hydrogen atom or primary alkyl group or secondary alkyl group with 1 to 6 carbon atoms R 5  and R 6  may be the same or different and each represent a bivalent aliphatic saturated hydrocarbon group with 1 to 8 carbon atoms, m is an integer of 0 or 1 to 3, n is an integer of 0 or 1 to 3, and k is an integer of 1 to 3, but if k is 2 or greater, then R 6 , R 1  and n in each phenyl group may all be the same or different, and X is a hydroxyphenyl group expressed by general formula (3) below: 
       
       
         
           
           
               
               
           
         
         wherein R 7  is an alkyl group with 1 to 8 carbon atoms or alkoxyl group with 1 to 8 carbon atoms, a is an integer of 1 to 3, b is an integer of 0 to 4, where 1≦a+b≦5, and if b is 2 or greater, then R 7 's may be the same or different. 
       
     
     
         3 . A polynuclear polyphenol compound according to  claim 2 , wherein the hydroxyphenyl group in general formula (3) above is expressed by general formula (4) below: 
       
         
           
           
               
               
           
         
         wherein R 8 , R 9  and R 10  each independently represent a hydrogen atom or alkyl group with 1 to 8 carbon atoms or alkoxyl group with 1 to 8 carbon atoms. 
       
     
     
         4 . A bis(formylphenyl) compound according to  claim 1 , which is expressed by formula (6) below: 
       
         
           
           
               
               
           
         
         wherein R 1  to R 6 , k, m and n are the same as the corresponding items in general formula (1), respectively. 
       
     
     
         5 . A bis(formylphenyl) compound according to  claim 1 , which is expressed by formula (7) below: 
       
         
           
           
               
               
           
         
         wherein R 1  to R 6 , k, m and n are the same as the corresponding items in general formula (1), respectively. 
       
     
     
         6 . A method of producing a bis(formylphenyl) compound according to  claim 1 , comprising:
 reacting a bis(hydroxy-formylphenyl) compound expressed by general formula (8) below as a direct material with a halogenated alkoxycarbonyl hydrocarbon expressed by general formula (9) below according to a phenylether manufacturing method in the presence of a base:   
       
         
           
           
               
               
           
         
         wherein R 1 , R 2 , n, m, k, R 5  and R 6  are the same as the corresponding items in general formula (1), respectively,
   Z—R 3 COOR 4   General formula (9)
 
 
         wherein Z is a halogen atom, R 3  is the same as the corresponding item in general formula (1), and R 4  is an alkyl group with 1 to 6 carbon atoms, and the halogen atom is a chlorine atom or bromine atom. 
       
     
     
         7 . A polynuclear polyphenol compound according to  claim 2 , which is expressed by formula (10) below: 
       
         
           
           
               
               
           
         
         wherein R 1  to R 6 , X, k, m and n are the same as the corresponding items in general formula (2), respectively. 
       
     
     
         8 . A polynuclear polyphenol compound according to  claim 2 , which is expressed by formula (11) below: 
       
         
           
           
               
               
           
         
         wherein R 1  to R 6 , X, k, m and n are the same as the corresponding items in general formula (2), respectively. 
       
     
     
         9 . A method of producing a polynuclear polyphenol compound according to  claim 2 , comprising:
 reacting a bis(formylphenyl) compound expressed by general formula (1) below as a direct material with a phenol in the presence of an acid catalyst:   
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  each independently represent an alkyl group with 1 to 8 carbon atoms or alkoxyl group with 1 to 8 carbon atoms, R 3  is a single-ring or condensed-ring aromatic hydrocarbon group with 6 to 15 carbon atoms or aliphatic saturated hydrocarbon group with 1 to 8 carbon atoms that may have a single-ring or condensed-ring aromatic hydrocarbon group with 6 to 15 carbon atoms, R 4  is a hydrogen atom or alkyl group with 1 to 6 carbon atoms, R 5  and R 6  may be the same or different and each represent a bivalent aliphatic saturated hydrocarbon group with 1 to 8 carbon atoms, m is an integer of 0 or 1 to 3, n is an integer of 0 or 1 to 3, and k is an integer of 1 to 3, but if k is 2 or greater, then R 6 , R 1  and n in each phenyl group may all be the same or different.