Container and composition for enhanced gas barrier properties

Abstract

A container comprising a polyester composition with enhanced carbon dioxide and oxygen barrier properties is provided. The polyester composition comprises a polyester and a gas barrier enhancing additive. In a particular embodiment, the gas barrier enhancing additive comprises a compound having the chemical formula: X—(X 1 ) s —COO—(X 2 ) t —X 3 —(X 4 ) u —OOC—(X 5 ) v —X 6 or X—(X 1 ) s —OOC—(X 2 ) t —X 3 —(X 4 ) u —COO—(X 5 ) v —X 6

1 . A container comprising a polyester composition comprising a polyester and a gas barrier enhancing additive, wherein the gas barrier enhancing additive comprises a compound having the chemical structure of Formula I or Formula II: 
     
       
         
         
             
             
         
       
       wherein X and X 6 , independent of one another, comprise hydrogen, halide, heteroatom, hydroxyl, amino, amido, alkylamino, arylamino, alkoxy, aryloxy, nitro, acyl, cyano, sulfo, sulfato, mercapto, imino, sulfonyl, sulfenyl, sulfinyl, sulfamoyl, phosphonyl, phosphinyl, phosphoryl, phosphino, thioester, thioether, anhydride, oximno, hydrazino, carbamyl, phosphonic acid, phosphonato, or a C 1 -C 10  monovalent hydrocarbon which is unsubstituted or substituted with one or more functional moieties; 
       wherein X 1 , X 2 , X 3 , X 4 , and X 5 , independent of one another, comprise a heteroatom or a C 1 -C 10  divalent hydrocarbon, wherein each heteroatom or C 1 -C 10  divalent hydrocarbon is unsubstituted or substituted with one or more functional moieties or one or more C 1 -C 10  hydrocarbyls that are unsubstituted or substituted with one or more functional moieties; and 
       wherein s, t, u, and v, independent of one another, is a number from 0 to 10; 
       wherein when X 3  comprises a C 6  or C 10  divalent aromatic hydrocarbon, X and X 6 , independent of one another, comprise a hydrogen, halide, heteroatom, hydroxyl, amino, amido, alkylamino, arylamino, alkoxy, aryloxy, nitro, acyl, cyano, sulfo, sulfato, mercapto, imino, sulfonyl, sulfenyl, sulfinyl, sulfamoyl, phosphonyl, phosphinyl, phosphoryl, phosphino, thioester, thioether, anhydride, oximno, hydrazino, carbamyl, phosphonic acid, phosphonato, or a C 3 -C 10  monovalent cyclic or heterocyclic non-aryl hydrocarbon that are unsubstituted or substituted with one or more functional moieties. 
     
   
   
       2 . The container of  claim 1 , wherein the gas barrier additive comprises a compound having the chemical structure of Formula I, wherein X and X 6  each comprise a phenyl group. 
   
   
       3 . The container of  claim 1 , wherein the gas barrier additive comprises a compound having the chemical structure of Formula I, wherein X and X 6  each comprise a phenyl group and s, t, u and v are 0. 
   
   
       4 . The container of  claim 1 , wherein the gas barrier additive comprises a compound having the chemical structure of Formula I, wherein X and X 6  each comprise a phenyl group, s, t, u and v are 0, and X 3  comprises a divalent hydro bi-furan, the gas barrier additive comprising a compound having the chemical structure: 
     
       
         
         
             
             
         
       
     
   
   
       5 . The container of  claim 1 , wherein the gas barrier additive comprises a compound having the chemical structure of Formula I, wherein X and X 6  each comprise a phenyl group, s and v are 0, t and u are 1, X 2  and X 4  each comprise a divalent C 1  hydrocarbon, and X 3  comprises a divalent cyclohexane, the gas barrier additive comprising a compound having the chemical structure: 
     
       
         
         
             
             
         
       
     
   
   
       6 . The container of  claim 1 , wherein the gas barrier additive comprises a compound having the chemical structure of Formula I, wherein X and X 6  each comprise a naphthyl group. 
   
   
       7 . The container of  claim 1 , wherein the gas barrier additive comprises a compound having the chemical structure of Formula I, wherein X and X 6  each comprise a naphthyl group and s and v are 0. 
   
   
       8 . The container of  claim 1 , wherein the gas barrier additive comprises a compound having the chemical structure of Formula I, wherein X and X 6  each comprise a naphthyl group, s and v are 0, t and u are 1, and X 2  and X 4  each comprise a divalent C 1  hydrocarbon. 
   
   
       9 . The container of  claim 1 , wherein the gas barrier additive comprises a compound having the chemical structure of Formula I, wherein X and X 6  each comprise a naphthyl group, s and v are 0, t and u are 1, X 2  and X 4  each comprise a divalent C 1  hydrocarbon, and X 3  comprises a divalent cyclohexane, the gas barrier additive comprising a compound having the chemical structure: 
     
       
         
         
             
             
         
       
     
   
   
       10 . The container of  claim 1 , wherein the gas barrier additive comprises a compound having the chemical structure of Formula I, wherein X and X 6  each comprise a cyclohexyl group. 
   
   
       11 . The container of  claim 1 , wherein the gas barrier additive comprises a compound having the chemical structure of Formula II, wherein X and X 6  each comprise a cyclohexyl group and s and v are 0. 
   
   
       12 . The container of  claim 1 , wherein the gas barrier additive comprises a compound having the chemical structure of Formula II, wherein X and X 6  each comprise a cyclohexyl group and s, t, u, and v are 0. 
   
   
       13 . The container of  claim 1 , wherein the gas barrier additive comprises a compound having the chemical structure of Formula II, wherein X and X 6  each comprise a cyclohexyl group, s, t, u, and v are 0, and X 3  comprises a divalent benzene, the gas barrier additive comprising a compound having the chemical structure: 
     
       
         
         
             
             
         
       
     
   
   
       14 . The container of  claim 13 , wherein the divalent benzene is meta-substituted, the gas barrier additive comprising a compound having the chemical structure: 
     
       
         
         
             
             
         
       
     
   
   
       15 . The container of  claim 13 , wherein the divalent benzene is para-substituted, the gas barrier additive comprising a compound having the chemical structure: 
     
       
         
         
             
             
         
       
     
   
   
       16 . The container of  claim 1 , wherein the gas barrier additive comprises a compound having the chemical structure of Formula II, wherein X and X 6  each comprise a cyclohexyl group, s, t, u, and v are 0, and X 3  comprises a divalent naphthalene, the gas barrier additive comprises a compound having the chemical structure: 
     
       
         
         
             
             
         
       
     
   
   
       17 . The container of  claim 16 , wherein the divalent naphthalene is substituted at the 2 and 6 positions, the gas barrier additive comprising a compound having the chemical structure: 
     
       
         
         
             
             
         
       
     
   
   
       18 . The container of  claim 1 , wherein the gas barrier additive comprises a compound having the chemical structure of Formula II, wherein X and X 6  each comprise a benzoate group. 
   
   
       19 . The container of  claim 1 , wherein the gas barrier additive comprises a compound having the chemical structure of Formula II, wherein X and X 6  each comprise a benzoate group and t and u are 0. 
   
   
       20 . The container of  claim 1 , wherein the gas barrier additive comprises a compound having the chemical structure of Formula II, wherein X and X 6  each comprise a benzoate group, t and u are 0, s and v are 1, and X 1  and X 5  each comprise a divalent C 1  hydrocarbon. 
   
   
       21 . The container of  claim 1 , wherein the gas barrier additive comprises a compound having the chemical structure of Formula II, wherein X and X 6  each comprise a benzoate group, t and u are 0, s and v are 1, and X 1  and X 5  each comprise a divalent C 1  hydrocarbon, and X 3  is a divalent benzene, the gas barrier additive comprising a compound having the chemical structure: 
     
       
         
         
             
             
         
       
     
   
   
       22 . The container of  claim 21 , wherein the divalent benzene is para-substituted, the gas barrier additive comprising a compound having the chemical structure: 
     
       
         
         
             
             
         
       
     
   
   
       23 . The container of  claim 1 , wherein the gas barrier additive comprises a compound having the chemical structure of Formula II, wherein X and X 6  each comprise a benzoate group. 
   
   
       24 . The container of  claim 1 , wherein the gas barrier additive comprises a compound having the chemical structure of Formula II, wherein X and X 6  each comprise a benzoate group, s and v are 2, and X 1  and X 5  each comprise a divalent C 1  hydrocarbon. 
   
   
       25 . The container of  claim 1 , wherein the gas barrier additive comprises a compound having the chemical structure of Formula II, wherein X and X 6  each comprise a benzoate group, s and v are 2, X 1  and X 5  each comprise a divalent C 1  hydrocarbon, t and u are 1, and X 2  and X 4  each comprise a divalent benzoate. 
   
   
       26 . The container of  claim 1 , wherein the gas barrier additive comprises a compound having the chemical structure of Formula II, wherein X and X 6  each comprise a benzoate group, s and v are 2, X 1  and X 5  each comprise a divalent C 1  hydrocarbon, t and u are 1, X 2  and X 4  each comprise a divalent benzoate, and X 3  comprises a divalent C 2  hydrocarbon, the gas barrier additive comprising a compound having the chemical structure: 
     
       
         
         
             
             
         
       
     
   
   
       27 . The container of  claim 26 , wherein the divalent benzoates are meta-substituted, the gas barrier additive comprising a compound having the chemical structure: 
     
       
         
         
             
             
         
       
     
   
   
       28 . The container of  claim 1 , wherein the gas barrier additive comprises a compound having the chemical structure of Formula II, wherein X and X 6  each comprise an aryloxy group. 
   
   
       29 . The container of  claim 1 , wherein the gas barrier additive comprises a compound having the chemical structure of Formula II, wherein X and X 6  each comprise an aryloxy group, t and u are 0, and X 3  comprises a divalent benzene. 
   
   
       30 . The container of  claim 1 , wherein the gas barrier additive comprises a compound having the chemical structure of Formula II, wherein X and X 6  each comprise a phenoxy group, t and u are 0, s and v are 1, X 1  and X 5  each comprise a straight-chain divalent C 2  hydrocarbon, and X 3  comprises a divalent benzene, the gas barrier additive comprising a compound having the chemical structure: 
     
       
         
         
             
             
         
       
     
   
   
       31 . The container of  claim 30 , wherein the divalent benzene is para-substituted, the gas barrier additive comprising a compound having the chemical structure: 
     
       
         
         
             
             
         
       
     
   
   
       32 . The container of  claim 1 , wherein the gas barrier additive is present in the polyester composition in an amount in the range of about 0.1 to about 10 weight percent of the polyester composition. 
   
   
       33 . The container of  claim 1 , wherein the polyester comprises polyethylene terephthalate. 
   
   
       34 . The container of  claim 1 , wherein the polyester composition comprises a poly(ethylene terephthalate) based copolymer having less than 20 percent diacid, less than 10 percent glycol modification, or both, based on 100 mole percent diacid component and 100 mole percent diol component. 
   
   
       35 . The container of  claim 1 , wherein the polyester composition comprises a polyester made using at least one first polycondensation catalyst selected from the group consisting of metals in groups 3, 4, 13, and 14 of the Periodic Table and comprising a catalyst residue remaining in the polyester from formation of the polyester, the catalyst residue comprising at least a portion of the at least one first polycondensation catalyst. 
   
   
       36 . The container of  claim 1 , wherein the polyester composition has an I.V. from about 0.65 dL/g to about 1.0 dL/g. 
   
   
       37 . A packaged beverage comprising a beverage disposed in the container of  claim 1  and a seal for sealing the beverage in the package. 
   
   
       38 . A polyester composition comprising a polyester and a gas barrier additive, wherein the gas barrier enhancing additive comprises a compound having the chemical structure of Formula I or Formula II: 
     
       
         
         
             
             
         
       
       wherein X and X 6 , independent of one another, comprise hydrogen, halide, heteroatom, hydroxyl, amino, amido, alkylamino, arylamino, alkoxy, aryloxy, nitro, acyl, cyano, sulfo, sulfato, mercapto, imino, sulfonyl, sulfenyl, sulfinyl, sulfamoyl, phosphonyl, phosphinyl, phosphoryl, phosphino, thioester, thioether, anhydride, oximno, hydrazino, carbamyl, phosphonic acid, phosphonato, or a C 1 -C 10  monovalent hydrocarbon which is unsubstituted or substituted with one or more functional moieties; 
       wherein X 1 , X 2 , X 3 , X 4 , and X 5 , independent of one another, comprise a heteroatom or a C 1 -C 10  divalent hydrocarbon, wherein each heteroatom or C 1 -C 10  divalent hydrocarbon is unsubstituted or substituted with one or more functional moieties or one or more C 1 -C 10  hydrocarbyls that are unsubstituted or substituted with one or more functional moieties; and 
       wherein s, t, u, and v, independent of one another, is a number from 0 to 10; 
       wherein when X 3  comprises a C 6  or C 10  divalent aromatic hydrocarbon, X and X 6 , independent of one another, comprise a hydrogen, halide, heteroatom, hydroxyl, amino, amido, alkylamino, arylamino, alkoxy, aryloxy, nitro, acyl, cyano, sulfo, sulfato, mercapto, imino, sulfonyl, sulfenyl, sulfinyl, sulfamoyl, phosphonyl, phosphinyl, phosphoryl, phosphino, thioester, thioether, anhydride, oximno, hydrazino, carbamyl, phosphonic acid, phosphonato, or a C 3 -C 10  monovalent cyclic or heterocyclic non-aryl hydrocarbon that are unsubstituted or substituted with one or more functional moieties.