Process for manufacturing a hydroxyester derivative intermediate and epoxy resins prepared therefrom

Abstract

A process for manufacturing an α-halohydrin intermediate and an epoxy resin prepared therefrom including epoxidizing an α-halohydrin intermediate produced from an in situ halide substitution-deesterification of an α-hydroxy ester derivative which has been obtained by the coupling reaction of a phenol or a mixture of phenols and a glycidyl ester optionally in the presence of a catalyst.

1 . A process for producing an α-hydroxy ester derivative of at least one or more phenols having a structure represented by the following Formula VI: 
         (R 2 ) y Ar(OR 1′ ) z   Formula VI 
       wherein y is from 0 to 750; z is from 1 to 150; Ar is an aromatic-containing moiety; R 1′ is an α-hydroxy ester propyl-containing moiety; and R 2  is a group substituted for a hydrogen atom on the Ar moiety; the process comprising reacting (1) at least one or more phenols with (2) a glycidyl ester or a substituted glycidyl ester.  
     
     
         2 . The process of  claim 1  wherein Component (1), the one or more phenols, comprises a structure represented by the following Formula XI: 
         (R 2 ) y Ar(OH) z   Formula XI 
       wherein y is 0 to 750; z is 1 to 150; Ar is an aromatic-containing moiety; and R 2  is a group substituted for a hydrogen atom on the Ar moiety.  
     
     
         3 . The process of  claim 2  wherein Component (1), the one or more phenols, comprises a structure represented by any one or more of Formulas XII-XV as follows:  
       
         
           
           
               
               
           
         
       
       wherein y is 0 to 5, and each y can be the same or different; z is 1 to 4, and each z can be the same or different; and R 2  is a group substituted for a hydrogen atom on the aromatic ring;  
       
         
           
           
               
               
           
         
       
       wherein y is 0 to 4, and each y can be he same or different; z is 1 to 3, and each z can be the same or different; R 2  is a group substituted for a hydrogen atom on the aromatic ring; and Z is (i) nil, (ii) a heteroatom with or without substituents thereon to complete its necessary bonding valence, (iii) —C(O)—, (iv) —S(O 2 )—, (v) —C(O)NH—, (vi) —P(O)Ar—, (vii) an organic aliphatic or cycloaliphatic moiety, saturated or unsaturated, with or without heteroatoms, or (viii) a partially or fully fluorinated organic aliphatic or cycloaliphatic moiety;  
       
         
           
           
               
               
           
         
       
       wherein y is 0 to 4, and each y can be the same or different; z is 1 to 3, and each z can be the same or different; R 2  is a group substituted for a hydrogen atom on the aromatic ring; Z is (i) nil, (ii) a heteroatom with or without substituents thereon to complete its necessary bonding valence, (iii) —C(O)—, (iv) —S(O 2 )—, (v) —C(O)NH—, (vi) —P(O)Ar—, (vii) an organic aliphatic or cycloaliphatic moiety, saturated or unsaturated, with or without heteroatoms, or (viii) a partially or fully fluorinated organic aliphatic moiety; and m is from 0.001 to 10; or  
       
         
           
           
               
               
           
         
       
       wherein y is 0 to 4, and each y can be the same or different; z is 1 to 3, and each z can be the same or different; R 2  is a group substituted for a hydrogen atom on the aromatic ring; Z′ (i) is an organic aliphatic moiety, saturated or unsaturated, with or without heteroatoms, wherein the aliphatic moiety has from 1 to 20 carbon atoms, (ii) a cycloaliphatic moiety, saturated or unsaturated, with or without heteroatoms, having from 3 to carbon atoms, (iii) an aromatic moiety, with or without heteroatoms, having 6 to 20 carbon atoms, (iv) a partially or fully fluorinated organic aliphatic, cycloaliphatic or aromatic moiety, or (v) any combination thereof; and m′ is 3 or 4.  
     
     
         4 . The process of  claim 1  wherein Component (2), the glycidyl ester or substituted glycidyl ester, comprises a structure represented by the following Formula XVI:  
       
         
           
           
               
               
           
         
       
       wherein R 4  is hydrogen, an alkyl group having from 1 to 20 carbon atoms, an alkenyl group having from 2 to 20 carbon atoms, a cycloaliphatic group having from 3 to 20 carbon atoms, or an aromatic group having from 6 to 20 carbon atoms; and R 5  is a glycidyl moiety.  
     
     
         5 . The process of  claim 4  wherein R 5  is selected from:  
       
         
           
           
               
               
           
         
       
       wherein R 3  is hydrogen, an alkyl group having from 1 to 20 carbon atoms, a cycloaliphatic group having from 3 to 20 carbon atoms, an aromatic group having from 6 to 20 carbon atoms, or any combination thereof.  
     
     
         6 . The process of  claim 5  wherein R 5  is selected from:  
       
         
           
           
               
               
           
         
       
     
     
         7 . The process of  claim 6  wherein Component (2), the glycidyl ester or substituted glycidyl ester, is selected from glycidyl formate, glycidyl acetate, methylglycidyl formate and methylglycidyl acetate.  
     
     
         8 . The process of  claim 7  wherein Component (2), the glycidyl ester, is glycidyl acetate.  
     
     
         9 . The process of  claim 1  wherein the amount of glycidyl ester or substituted glycidyl ester reacted with at least one or more phenols is from about 0.5 equivalents to about 50 equivalents of glycidyl ester or substituted glycidyl ester per one equivalent of phenolic hydroxyl.  
     
     
         10 . The process of  claim 1  wherein the reaction of preparing the α-hydroxy ester derivative is carried out in the presence of a solvent.  
     
     
         11 . The process of  claim 1  wherein the reaction of preparing the α-hydroxy ester derivative is carried out in the presence of a catalyst.  
     
     
         12 . The process of  claim 11  wherein the catalyst is a phase transfer catalyst.  
     
     
         13 . The process of  claim 12  wherein the catalyst is an organopnicogen-containing catalyst.  
     
     
         14 . The process of  claim 13  wherein the catalyst is homogeneous or heterogeneous.  
     
     
         15 . The process of  claim 14  wherein the catalyst is from about 0.001 percent to about 1000 percent by weight based on the amount of the phenol or mixture of phenols used in the reaction.  
     
     
         16 . The process of  claim 1  wherein the reaction of preparing the α-hydroxy ester derivative is carried out at a temperature of from about 10° C. to about 160° C.