Compositions and methods for biodegradable, biomass-based polyesters

Abstract

The disclosure relates to biomass-based polyester materials; methods of making biomass-based polyester materials; polyester compositions comprising the disclosed biomass-based polyester materials; polymer compositions comprising the biomass-based polyester materials and one or more additional polymer, including a conventional or non-biomass-based polymer; and articles comprising the disclosed biomass-based polyester materials or disclosed polymer compositions comprising a disclosed biomass-based polyester materials.

What is claimed is: 
     
         1 . A method of making a biomass-based polyester material, the method comprising the step of polycondensation of a first monomer component comprising at least one diol and a second monomer component comprising at least one dicarboxylic acid component, thereby forming the biomass-based polyester material;
 wherein polycondensation is carried out in the presence of a catalyst; and   wherein the first monomer component, the second monomer component, or both comprise at least one biomass-based monomer component.   
     
     
         2 . The method of  claim 1 , wherein the first monomer component is present in about 10 parts to about 150 parts on a molar basis and wherein the second monomer component is present in about 10 parts to about 150 parts on a molar basis. 
     
     
         3 . The method of  claim 1 , wherein the first monomer component comprises a biomass-based monomer component, wherein the biomass-based monomer is selected from 1,5-pentanediol (1,5-PDO), tetrahydrofurandimethanol (THFDM), furandimethanol (FDM), and combinations thereof. 
     
     
         4 . The method of  claim 1 , wherein the first monomer component comprises a biomass-based monomer component, wherein the biomass-based monomer comprises 1,5-pentanediol (1,5-PDO). 
     
     
         5 . The method of  claim 1 , wherein the biomass-based polyester material has a molecular weight of from about 70 kDa to about 200 kDa. 
     
     
         6 . The method of  claim 1 , wherein the second monomer component is selected from adipic acid and one of terephthalic acid (TPA) and furandicarboxylic acid (FDCA). 
     
     
         7 . The method of  claim 1 , wherein the first monomer component comprises a first diol component and a second diol component, wherein the first diol component is present in an amount of about 10 to about 150 parts; wherein the second diol component is present in an amount of about 10 to about 150 parts; wherein the first diol component and the second diol component are present in an aggregate amount of not greater than about 150 parts; and
 wherein parts are given on a molar basis.   
     
     
         8 . The method of  claim 1 , wherein the second monomer component comprises a biomass-based monomer, wherein the second monomer component is selected from terephthalic acid (TPA), furandicarboxylic acid (FDCA), adipic acid, and combinations thereof. 
     
     
         9 . The method of  claim 1 , wherein the second monomer component comprises a first dicarboxylic acid component and a second dicarboxylic acid component, wherein the first dicarboxylic acid component is present in an amount of about 10 to about 150 parts; wherein the second dicarboxylic acid component is present in an amount of about 10 to about 150 parts; wherein the first dicarboxylic acid component and the second dicarboxylic acid component are present in an aggregate amount of not greater than about 150 parts; and wherein parts are given on a molar basis. 
     
     
         10 . The method of  claim 1 , wherein the biomass-based polyester material has a structure given by one of the following formulas: 
       
         
           
           
               
               
           
         
       
     
     
         11 . The method of  claim 1 , wherein the biomass-based polyester material has a structure given by the formula: 
       
         
           
           
               
               
           
         
         wherein R is a C5 aliphatic chain. 
       
     
     
         12 . A biomass-based polyester material comprising repeating units derived from a first monomer component comprising at least one diol and repeating units derived from a second monomer component comprising at least one dicarboxylic acid component;
 wherein the repeating units derived from the first monomer component are present in an amount of from about 25 mol % to about 75 mol %;   wherein the repeating units derived from the second monomer component are present in an amount of from about 25 mol % to about 75 mol %;   wherein the ratio of the first monomer to the second monomer, on a molar basis, is from about 1.5:1 to about 1:1.5;   wherein the mol % is based on the total of the repeating units derived from the first monomer component and the repeating units derived from the second monomer component;   wherein the repeating units are derived from at least one biomass-based monomer component; and   wherein the at least one biomass-based monomer component is the first monomer component, the second monomer component, and combinations thereof.   
     
     
         13 . The biomass-based polyester material of  claim 12 , wherein the repeating units derived from the first monomer component are present in an amount of from about 35 mol % to about 65 mol %. 
     
     
         14 . The biomass-based polyester material of  claim 12 , wherein the repeating units derived from the first monomer component comprise a biomass-based monomer component, wherein the biomass-based monomer is selected from 1,5-pentanediol (1,5-PDO), tetrahydrofurandimethanol (THFDM), furandimethanol (FDM), and combinations thereof. 
     
     
         15 . The biomass-based polyester material of  claim 12 , wherein the first monomer component comprises a biomass-based monomer component, wherein the biomass-based monomer comprises 1,5-pentanediol (1,5-PDO). 
     
     
         16 . The biomass-based polyester material of  claim 12 , wherein the biomass-based polyester material has a molecular weight of from about 70 kDa to about 200 kDa. 
     
     
         17 . The biomass-based polyester material of  claim 12 , wherein the second monomer component is selected from adipic acid and one of terephthalic acid (TPA) and furandicarboxylic acid (FDCA). 
     
     
         18 . The biomass-based polyester material of  claim 12 , wherein the second monomer component comprises a biomass-based monomer, wherein the second monomer component is selected from terephthalic acid (TPA), furandicarboxylic acid (FDCA), adipic acid, and combinations thereof. 
     
     
         19 . The biomass-based polyester material of  claim 12 , wherein the biomass-based polyester material has a structure given by one of the following formulas: 
       
         
           
           
               
               
           
         
       
     
     
         20 . The biomass-based polyester material of  claim 12 , wherein the biomass-based polyester material has a structure given by the formula: 
       
         
           
           
               
               
           
         
         wherein R is a C5 aliphatic chain.