2-aryl-3-(aminoaryl)-3-(hydroxyaryl)phthalimidine compounds and methods for making them

Abstract

Compounds and methods for preparing 2-aryl-3-(aminoaryl)-3-(hydroxyaryl)phthalimidines having a formula of: wherein R 1 is independently selected from a group consisting of a hydrocarbyl radical, a nitro radical, and a halogen atom; “a” is an integer from 0-4; and Ar 1 and Ar 2 are each independently an aromatic radical, are disclosed. The 2-aryl-3-(aminoaryl)-3-(hydroxyaryl)phthalimidine compounds are useful for preparing other useful monomers and polymers.

1 . A method for preparing a 2-aryl-3-(aminoaryl)-3-(hydroxyaryl)phthalimidine, the method comprising: reacting a precursor compound with an aromatic primary amine in the presence of an acidic catalyst, wherein the aromatic primary amine as a formula of Ar 1 —NH 2 , wherein Ar 1  is an aromatic radical; and the precursor compound is at least one member selected from the group consisting of a phenolphthalein compound and a 2-aryl-3,3-bis(hydroxyaryl)phthalimidine.  
     
     
         2 . The method of  claim 1 , wherein the acidic catalyst comprises a salt of an organic amine and an acid.  
     
     
         3 . The method of  claim 2 , wherein the acid is selected from the group consisting of an inorganic acid, an organic acid, and combinations of the foregoing acids.  
     
     
         4 . The method of  claim 1 , wherein the aromatic primary amine comprises aniline or a substituted aniline.  
     
     
         5 . The method of  claim 1 , wherein the precursor compound is a phenolphthalein compound having a formula:  
       
         
           
           
               
               
           
         
       
       wherein R 1  is independently selected from a group consisting of a hydrogen atom, a hydrocarbyl radical, a nitro radical, and a halogen atom; “a” is an integer from 1-4; and Ar 1  is an aromatic radical.  
     
     
         6 . The method of  claim 1 , wherein the precursor compound is phenolphthalein.  
     
     
         7 . The method of  claim 1 , wherein the precursor is a 2-aryl-3,3-bis(hydroxyaryl)phthalimidine having a formula:  
       
         
           
           
               
               
           
         
       
       wherein R 1  is independently selected from a group consisting of a hydrocarbyl radical, a nitro radical, and a halogen atom; “a” is an integer from 0-4; and Ar 1  and Ar 2  are each independently an aromatic radical.  
     
     
         8 . The method of  claim 7 , wherein the 2-aryl-3,3-bis(hydroxyaryl)phthalimidine is 2-phenyl-3,3-bis (4-hydroxyphenyl)phthalimidine.  
     
     
         9 . The method of  claim 1 , wherein the aromatic primary amine is aniline.  
     
     
         10 . The method of  claim 1 , further comprising removing a by-product having a formula [Ar 1 ]—OH, wherein Ar 1  is an aromatic radical.  
     
     
         11 . A method for preparing 2-phenyl-3-(4-aminophenyl)-3-(4-hydroxyphenyl)phthalimidine, the method comprising reacting a precursor compound with aniline in the presence of an acidic catalyst to form the 2-phenyl-3-(4-aminophenyl)-3-(4-hydroxyphenyl)phthalimidine; wherein the precursor compound is selected from a group consisting of phenolphthalein and 2-phenyl-3,3-bis(4-hydroxyphenyl)phthalimidine.  
     
     
         12 . The method of  claim 11 , wherein the acidic catalyst is formed in-situ by contacting aniline with an acid.  
     
     
         13 . The method of  claim 11 , wherein the acidic catalyst is aniline hydrochloride.  
     
     
         14 . The method of  claim 11 , wherein the precursor compound is 2-phenyl-3-(4-hydroxyphenyl) -3-(2-hydroxyphenyl)phthalimidine.  
     
     
         15 . A polymer comprising structural units derived from at least one 2-aryl-3-(aminoaryl)-3-hydroxyaryl)phthalimidine having a formula:  
       
         
           
           
               
               
           
         
       
       wherein R 1  is independently selected from a group consisting of a hydrogen atom, a hydrocarbyl radical, a nitro radical, and a halogen atom: “a” is an integer from 0-4; and Ar 1  and Ar 2  are each independently an aromatic radical.