Methods for the preparation of polyesters, poly(ester amide)s and poly(ester imide)s and uses of the materials obtained therefrom

Abstract

The present invention relates to methods for the preparation of polyesters, poly(ester amide)s and poly(ester imide)s. The materials obtained by the methods of present invention are useful as fluid separation membranes and as high performance materials.

What is claimed is:  
     
         1 . A process for separating one or more gases from a mixture of gases comprising the steps of bringing said gaseous mixture into contact with a first side of a gas separation membrane such that a portion of said gas mixture permeates to a second side of said membrane and a portion of said gas mixture is collected as a nonpermeate, the resulting gas mixture on said second side of said membrane being enriched in one or more components over that of the mixture on the first side of said membrane, wherein said gas separation membrane is formed from a polymer containing a main-chain ester linkage, wherein said polymer is formed by a polycondensation reaction between an acetyl chloride and a phenol in presence of a catalyst.  
     
     
         2 . The process of  claim 1  wherein said polycondensation reaction is catalyzed independently by toluenesulfonyl chloride, benzenesulfonylchloride, trimethylsilane chloride, and triphenyl phosphite or a mixture thereof.  
     
     
         3 . The process of  claim 1  wherein said polymer is a polyester, a poly(ester amide), or a poly(etser imide).  
     
     
         4 . The process of  claim 3  wherein said polymer is a poly(ester imide) of the following general formula:  
       
         
           
           
               
               
           
         
       
       Where x is an integer larger than 10 and Ar is independently  
       
         
           
           
               
               
           
         
       
       mixture thereof; 
 —Ar 1 — is independently  
                     
 mixture thereof;  
 —R′— is  
                     
 Z and Z′ are:  
 —H, —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 ,iso-propyl, iso-butyl, tert-butyl, —Br, —Cl, —F, —NO 2 , —CN  
                     
 n  32  0-4;  
 —Ar 2 — is independently  
                     
 or a mixture thereof;  
 Where Ar 3  is independently  
                     
 or a mixture thereof;  
                     
 
     
     
         5 . The process of  claim 4  wherein said Ar is  
       
         
           
           
               
               
           
         
       
     
     
         6 . The process of  claim 4  wherein said —Ar 1 — is:  
       
         
           
           
               
               
           
         
       
     
     
         7 . The process of  claim 4  wherein said —Ar 2 — is:  
       
         
           
           
               
               
           
         
       
     
     
         8 . The process of  claim 4  wherein said poly(ester imide) is formed by reacting tetrabromobisphenol A with one of the following dianilines: 4,4′-oxy-dianiline, 1,3-phenylenediamine, 1,4-phenylenediamine, 1,5-naphthalenediamine, 4,4′-hexafluoroisopropylidene dianiline, 2,4,6-trimethyl-1,3-phenylene diamine, or a mixture thereof.  
     
     
         9 . The process of  claim 4  wherein said poly(ester imide) is formed by reacting 4,4′-hexafluoroisopropylidene bisphenol with one of the following dianilines: 4,4′-oxy-dianiline, 1,3-phenylenediamine, 1,4-phenylenediamine, 1,5-naphthalenediamine, 4,4′-hexafluoroisopropylidene dianiline, 2,4,6-trimethyl-1,3-phenylene diamine, or a mixture thereof.  
     
     
         10 . The process of  claim 3  wherein said polymer is a poly(ester amide) of the following general formula:  
       
         
           
           
               
               
           
         
       
       Where y is between 0.01 and 0.99 and —Ar 1 — is independently  
       
         
           
           
               
               
           
         
       
       or a mixture thereof; 
 —R′— is  
                     
 Z and Z′ are:  
 —H, —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 ,iso-propyl, iso-butyl, tert-butyl, —Br, —Cl, —F, —NO 2 , —CN  
                     
 n=0-4;  
 —Ar 2 — is independently  
                     
 or a mixture thereof;  
 Where Ar 3  is independently  
                     
 or a mixture thereof;  
 —Ar 4 —is  
                     
 
     
     
         11 . The process of  claim 10  wherein said —Ar 1 — is:  
       
         
           
           
               
               
           
         
       
     
     
         12 . The process of  claim 10  wherein said —Ar 2 — is:  
       
         
           
           
               
               
           
         
       
     
     
         13 . The process of  claim 10  wherein said poly(ester amide) is formed by reacting tetrabromobisphenol A with one of the following dianilines: 4,4′-oxy-dianiline, 1,3-phenylenediamine, 1,4-phenylenediamine, 1,5-naphthalenediamine, 4,4′-hexafluoroisopropylidene dianiline, 2,4,6-trimethyl-1,3-phenylene diamine, or a mixture thereof.  
     
     
         14 . The process of  claim 10  wherein said poly(ester amide) is formed by reacting 4,4′-hexafluoroisopropylidene bisphenol with one of the following dianilines: 4,4′-oxy-dianiline, 1,3-phenylenediamine, 1,4-phenylenediamine, 1,5-naphthalenediamine, 4,4′-hexafluoroisopropylidene dianiline, 2,4,6-trimethyl-1,3-phenylene diamine, or a mixture thereof.  
     
     
         15 . The process of  claim 3  wherein said polymer is a polyester of the following general formula:  
       
         
           
           
               
               
           
         
       
       Where x is an integer larger than 10 and —Ar 1 — is independently  
       
         
           
           
               
               
           
         
       
       or a mixture thereof; 
 —R′— is  
                     
 Z and Z′ are:  
 —H, —C H 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 ,iso-propyl, iso-butyl, tert-butyl, —Br, —Cl, —F, ——NO 2 , —CN  
                     
 n=0-4.  
 
     
     
         16 . The process of  claim 15  wherein said —Ar 1 — is:  
       
         
           
           
               
               
           
         
       
     
     
         17 . A polymer containing a main-chain ester linkage which is formed by the solution polycondensation reaction between an acetyl chloride and a phenol in presence of a catalyst.  
     
     
         18 . The polymer of  claim 17  wherein the solution polycondensation reaction is catalyzed independently by toluenesulfonyl chloride, benzenesulfonylchloride, trimethylsilane chloride, and triphenyl phosphite or a mixture thereof.  
     
     
         19 . The process of  claim 17  wherein said polymer is a polyester, a poly(ester amide), or a poly(etser imide).  
     
     
         20 . The polymer of  claim 19  wherein said polymer is a poly(ester imide) of the following general formula:  
       
         
           
           
               
               
           
         
       
       Where x is an integer larger than 10 and Ar is independently  
       
         
           
           
               
               
           
         
       
       or a mixture thereof; 
 —Ar 1 — is independently  
                     
 or a mixture thereof;  
 —R′— is  
                     
 —R″— is  
                     
 Z and Z′ are:  
 —H, —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 ,iso-propyl, iso-butyl, tert-butyl, —Br, —Cl, —F, —NO 2 , —CN  
                     
 n=0-4;  
 —Ar 2 — is independently  
                     
 or a mixture thereof;  
 Where Ar 3  is independently  
                     
 or a mixture thereof;  
 —Ar 4 — is  
                     
 
     
     
         21 . The polymer of  claim 20  wherein said Ar is  
       
         
           
           
               
               
           
         
       
     
     
         22 . The polymer of  claim 20  wherein said —Ar 1 — is:  
       
         
           
           
               
               
           
         
       
     
     
         23 . The polymer of  claim 20  wherein said —Ar 2 — is:  
       
         
           
           
               
               
           
         
       
     
     
         24 . The polymer of  claim 20  wherein said poly(ester imide) is formed by reacting tetrabromobisphenol A with one of the following dianilines: 4,4′-oxy-dianiline, 1,3-phenylenediamine, 1,4-phenylenediamine, 1,5-naphthalenediamine, 4,4′-hexafluoroisopropylidene dianiline, 2,4,6-trimethyl-1,3-phenylene diamine, or a mixture thereof.  
     
     
         25 . The polymer of  claim 20  wherein said poly(ester imide) is formed by reacting 4,4′-hexafluoroisopropylidene bisphenol with one of the following dianilines: 4,4′-oxy-dianiline, 1,3-phenylenediamine, 1,4-phenylenediamine, 1,5-naphthalenediamine, 4,4′-hexafluoroisopropylidene dianiline, 2,4,6-trimethyl-1,3-phenylene diamine, or a mixture thereof.  
     
     
         26 . The polymer of  claim 19  wherein said polymer is a poly(ester amide) of the following general formula:  
       
         
           
           
               
               
           
         
         Where y is between 0.01 and 0.99 and —Ar 1 — is independently  
         
           
             
             
                 
                 
             
           
         
         or a mixture thereof;  
         —R′— is  
         
           
             
             
                 
                 
             
           
         
         Z and Z′ are:  
         —H, —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 ,iso-propyl, iso-butyl, tert-butyl, —Br, —Cl, —F, —NO 2 , —CN  
         
           
             
             
                 
                 
             
           
         
         n=0-4;  
         —Ar 2 — is independently  
         
           
             
             
                 
                 
             
           
         
         or a mixture thereof;  
         Where Ar 3  is independently  
         
           
             
             
                 
                 
             
           
         
         or a mixture thereof;  
         —Ar 4 — is  
         
           
             
             
                 
                 
             
           
         
       
     
     
         27 . The polymer of  claim 26  wherein said —Ar 1  — is:  
       
         
           
           
               
               
           
         
       
     
     
         28 . The polymer of  claim 26  wherein said —Ar 2 — is:  
       
         
           
           
               
               
           
         
       
     
     
         29 . The polymer of  claim 26  wherein said poly(ester amide) is formed by reacting tetrabromobisphenol A with one of the following dianilines: 4,4′-oxy-dianiline, 1,3-phenylenediamine, 1,4-phenylenediamine, 1,5-naphthalenediamine, 4,4′-hexafluoroisopropylidene dianiline, 2,4,6-trimethyl-1,3-phenylene diamine, or a mixture thereof.  
     
     
         30 . The polymer of  claim 26  wherein said poly(ester amide) is formed by reacting 4,4′-hexafluoroisopropylidene bisphenol with one of the following dianilines: 4,4′-oxy-dianiline, 1,3-phenylenediamine, 1,4-phenylenediamine, 1,5-naphthalenediamine, 4,4′-hexafluoroisopropylidene dianiline, 2,4,6-trimethyl-1,3-phenylene diamine, or a mixture thereof.  
     
     
         31 . The polymer of  claim 19  wherein said polymer is a polyester of the following general formula:  
       
         
           
           
               
               
           
         
       
       Where x is an integer larger than 10 and —Ar 1 — is independently  
       
         
           
           
               
               
           
         
       
       or a mixture thereof; 
 —R′— is  
                     
 Z and Z′ are:  
 —H, —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 ,iso-propyl, iso-butyl, tert-butyl, —Br, —Cl, —F, —NO 2 , —CN  
                     
 n=0-4.  
 
     
     
         32 . The polymer of  claim 31  wherein said —Ar 1 — is:  
       
         
           
           
               
               
           
         
       
     
     
         33 . A poly(ester imide) comprised of chemically combined aromatic units of the following general formula:  
       
         
           
           
               
               
           
         
       
       where —Ar 1 — is a divalent aromatic organic radical having the following structure  
       
         
           
           
               
               
           
         
       
       or a mixture thereof, and —Ar 2 — is independently a divalent aromatic radical having the following structure:  
       
         
           
           
               
               
           
         
       
       or a mixture thereof; 
 Where Ar 3  is independently  
                     
 or a mixture thereof.;  
 —Ar 4 — is  
                     
 or a mixture thereof.  
 
     
     
         34 . The poly(ester imide) of  claim 33  where said —Ar 2 — is  
       
         
           
           
               
               
           
         
       
     
     
         35 . The polymer of  claim 34  wherein said poly(ester imide) is formed by reacting tetrabromobisphenol A with one of the following dianilines: 4,4′-oxy-dianiline, 1,3-phenylenediamine, 1,4-phenylenediamine, 1,5-naphthalenediamine, 4,4′-hexafluoroisopropylidene dianiline, 2,4,6-trimethyl-1,3-phenylene diamine, or a mixture thereof.