Process for the Preparation of Defined Functional Lactic Acid Oligomers

Abstract

A process for manufacturing defined functional lactic acid oligomers, can include contacting lactide with at least one compound that is a transfer agent. Oligomers can be prepared according to the process.

1 - 14 . (canceled) 
     
     
         15 . A block copolymer comprising:
 at least one compound, wherein the compound is a polymer selected from the group consisting of polypropylene, polyethylene, poly (L) lactic acid, poly (D) lactic acid, poly (D,L) lactic acid, polysiloxane, polybutylene succinate, polytrimethylene carbonate, polyester, poly ether, polystyrene, polyisoprene, polycarbonate, polyalkylenecarbonate, polyvinyl alcohol, polyurethane, and polyacrylate, wherein each polymer contains n number of OH and/or NH 2  group(s), wherein n is an integer greater than or equal to 1, wherein   
       
         
           
             
               
                 
                   
                     Moles 
                      
                     
                         
                     
                      
                     of 
                      
                     
                         
                     
                      
                     Lactide 
                   
                   
                     ( 
                     
                       Moles 
                        
                       
                           
                       
                        
                       of 
                        
                       
                           
                       
                        
                       Compound 
                       * 
                       n 
                     
                     ) 
                   
                 
                 ≤ 
                 70 
               
               ; 
             
           
         
       
       and
 one or more lactic acid chains, wherein each lactic acid chain is bonded to one of the polymers, wherein 
 
       
         
           
             
               
                 
                   
                     
                       Mn 
                        
                       
                         ( 
                         
                           lactic 
                            
                           
                               
                           
                            
                           acid 
                            
                           
                               
                           
                            
                           oligomer 
                         
                         ) 
                       
                     
                     - 
                     
                       Mw 
                        
                       
                         ( 
                         compound 
                         ) 
                       
                     
                   
                   n 
                 
                 ≤ 
                 
                   10 
                    
                   
                       
                   
                    
                   100 
                    
                   
                       
                   
                    
                   g 
                    
                   
                     / 
                   
                    
                   mol 
                 
               
               , 
             
           
         
       
       wherein Mn(lactic acid chain) is measured by size exclusion chromatography, and wherein n is the number of OH and NH2 groups present in the compound, wherein the block copolymer is made by a process comprising:
 contacting lactide monomers in the presence of a catalyst with the at least one compound to form the block copolymer comprising the lactic acid chain; 
 wherein reaction is performed at a temperature of at least 70° C.; 
 quenching the reaction so that the lactic acid chains formed by reaction consist of 70 or less of the lactide monomers, wherein the quenching agent is an acid chloride having a formula of Cl—CO—R 9 , wherein R 9  is 1-pentenyl or aminoethyl. 
 
     
     
         16 . The block copolymer according to  claim 15 , wherein said process is performed without solvent. 
     
     
         17 . The block copolymer according to  claim 16 , wherein said process is performed at a temperature of 110° C. to 190° C. 
     
     
         18 . The block copolymer according to  claim 15 , wherein the catalyst is an organometallic catalyst. 
     
     
         19 . The block copolymer according to  claim 15 , wherein said catalyst has general formula:
   M(Y 1 , Y 2 , . . . Y p ) q ,   wherein M is a metal selected from the elements of columns 3 to 12 of the periodic table of the elements, as well as the elements Al, Ga, In, Tl, Ge, Sn, Pb, Sb, Ca, Mg and Bi;   wherein Y 1 , Y 2 , . . . Y p  are each substituents selected from C 1-20  alkyls, C 6-30  aryls, C 1-20  alkoxys, C 6-30  aryloxys, other oxides, carboxylates, and halide groups as well as elements of group 15 and/or 16 of the periodic table;   wherein p and q are integers between 1 and 6.   
     
     
         20 . The block copolymer according to  claim 19 , wherein the reaction is performed at a temperature of at least 140° C. 
     
     
         21 . The block copolymer according to  claim 15 , wherein n is at least 2. 
     
     
         22 . The block copolymer according to  claim 15 , wherein said compound is a polymer that is selected from the group consisting of: polypropylene, polyethylene, poly (L) lactic acid, poly (D) lactic acid, poly (D,L) lactic acid, polysiloxane, polybutylene succinate, polytrimethylene carbonate, polystyrene, polycarbonate, polyalkylenecarbonate, polyvinyl alcohol, and polyurethane, wherein the polymer contains n number of OH and/or NH 2  group(s), and wherein n is an integer greater than or equal to 1. 
     
     
         23 . The block copolymer according to  claim 15 , wherein the compound is a polymer selected from the group consisting of: polypropylene, polyethylene, polysiloxane, polybutylene succinate, polytrimethylene carbonate, polycarbonate, polyalkylenecarbonate, polyvinyl alcohol, polyurethane, and polyaminoacid, wherein the polymer contains n number of OH group(s), and wherein n is an integer greater than or equal to 1.