Farnesene interpolymers

Abstract

Farnesene interpolymer comprises units derived from a farnesene (e.g., α-farnesene or β-farnesene) and units derived from at least one vinyl monomer. The farnesene interpolymer can be prepared by copolymerizing the farnesene and at least one vinyl monomer in the presence of a catalyst. In some embodiments, the farnesene is prepared from a sugar by using a microorganism. In other embodiments, the at least one vinyl monomer is ethylene, an α-olefin, or a substituted or unsubstituted vinyl halide, vinyl ether, acrylonitrile, acrylic ester, methacrylic ester, acrylamide or methacrylamide, or a combination thereof.

What is claimed is: 
     
         1 . A farnesene interpolymer comprising one or more polymer molecules having formula (X′): 
       
         
           
           
               
               
           
         
       
       wherein each of n and m is independently an integer from 1 to about 100,000; X has one or more of formulae (I′)-(VIII′): 
       
         
           
           
               
               
           
         
       
       and 
       Y has formula (IX′): 
       
         
           
           
               
               
           
         
       
       wherein R 1  has formula (XI): 
       
         
           
           
               
               
           
         
       
       R 2  has formula (XII): 
       
         
           
           
               
               
           
         
       
       R 3  has formula (XIII): 
       
         
           
           
               
               
           
         
       
       and 
       R 4  has formula (XIV): 
       
         
           
           
               
               
           
         
       
       wherein each of R 5 , R 6 , R 7  and R 8  is independently H, alkyl, cycloalkyl, aryl, cycloalkenyl, alkynyl, heterocyclyl, alkoxy, aryloxy, carboxy, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, acyloxy, nitrile or halo, wherein a mole percent ratio of X to Y is from about 1:4 to about 100:1, and wherein the farnesene interpolymer has a weight-average molecular weight less than about 500,000 daltons. 
     
     
         2 . The farnesene interpolymer of  claim 1 , wherein one of R 5 , R 6 , R 7  and R 8  is aryl; and each of the other three of R 5 , R 6 , R 7  and R 8  is H. 
     
     
         3 . The farnesene interpolymer of  claim 2 , wherein the aryl is phenyl. 
     
     
         4 . The farnesene interpolymer of  claim 1 , wherein at least one of R 5 , R 6 , R 7  and R 8  is alkoxy, aryloxy, carboxy, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, acyloxy, nitrile, or halo. 
     
     
         5 . The farnesene interpolymer of  claim 1 , wherein formula (I′) is in an amount of at most about 80 wt. %, based on the total weight of the farnesene interpolymer. 
     
     
         6 . The farnesene interpolymer of  claim 1 , wherein formula (II′) is in an amount from about 15 wt. % to about 99 wt. %, based on the total weight of the farnesene interpolymer. 
     
     
         7 . A farnesene interpolymer comprising one or more polymer molecules having formula (X′): 
       
         
           
           
               
               
           
         
       
       wherein each of n and m is independently an integer from 1 to about 100,000; X is derived from a farnesene and has one or more of formulae (I′)-(VIII′): 
       
         
           
           
               
               
           
         
       
       and 
       Y is derived from at least one vinyl monomer and has formula (IX′): 
       
         
           
           
               
               
           
         
       
       wherein R 1  has formula (XI): 
       
         
           
           
               
               
           
         
       
       R 2  has formula (XII): 
       
         
           
           
               
               
           
         
       
       R 3  has formula (XIII): 
       
         
           
           
               
               
           
         
       
       and 
       R 4  has formula (XIV): 
       
         
           
           
               
               
           
         
       
       wherein each of R 5 , R 6 , R 7  and R 8  is independently H, alkyl, cycloalkyl, aryl, cycloalkenyl, alkynyl, heterocyclyl, alkoxy, aryloxy, carboxy, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, acyloxy, nitrile or halo, wherein a mole percent ratio of X to Y is from about 1:4 to about 100:1, and wherein the farnesene is in an amount of less than about 30 mole %, based on the total amount of the farnesene interpolymer. 
     
     
         8 . The farnesene interpolymer of  claim 1 , wherein one of R 5 , R 6 , R 7  and R 8  is aryl; and each of the other three of R 5 , R 6 , R 7  and R 8  is H. 
     
     
         9 . The farnesene interpolymer of  claim 8 , wherein the aryl is phenyl. 
     
     
         10 . The farnesene interpolymer of  claim 1 , wherein at least one of R 5 , R 6 , R 7  and R 8  is alkoxy, aryloxy, carboxy, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, acyloxy, nitrile, or halo. 
     
     
         11 . A polyfarnesene, wherein the polyfarnesene has formula (X′): 
       
         
           
           
               
               
           
         
       
       wherein n is from 1 to about 100,000; m is from 0 to about 100,000; X has one or more of formulae (I′)-(VIII′): 
       
         
           
           
               
               
           
         
       
       and 
       Y has formula (IX′): 
       
         
           
           
               
               
           
         
       
       wherein R 1  has formula (XI): 
       
         
           
           
               
               
           
         
       
       and 
       R 2  has formula (XII): 
       
         
           
           
               
               
           
         
       
       R 3  has formula (XIII): 
       
         
           
           
               
               
           
         
       
       and 
       R 4  has formula (XIV): 
       
         
           
           
               
               
           
         
       
       wherein each of R 5 , R 6 , R 7  and R 8  is independently H, alkyl, cycloalkyl, aryl, cycloalkenyl, alkynyl, heterocyclyl, alkoxy, aryloxy, carboxy, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, acyloxy, nitrile or halo, with the proviso that when m is 0, formula (I′) is in an amount of at most about 80 wt. % and formula (II′) is in an amount of from about 5 wt. % to about 99 wt. %, based on a total weight of the polyfarnesene, and when m is 1 or greater, a mole percent ratio of X to Y is from about 1:4 to about 100:1. 
     
     
         12 . The polyfarnesene of  claim 11 , wherein the polyfarnesene has a weight-average molecular weight less than about 500,000 daltons. 
     
     
         13 . The polyfarnesene of  claim 12 , wherein m is 0 and the polyfarnesene is a farnesene homopolymer. 
     
     
         14 . The polyfarnesene of  claim 11 , wherein R 5  is aryl; and each of R 6 , R 7  and R 8  is H. 
     
     
         15 . The polyfarnesene of  claim 14 , wherein the aryl is phenyl. 
     
     
         16 . The polyfarnesene of  claim 11 , wherein at least one of R 5 , R 6 , R 7  and R 8  is alkoxy, aryloxy, carboxy, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, acyloxy, nitrile, or halo. 
     
     
         17 . A functionalized farnesene interpolymer prepared by functionalizing the polyfarnesene of  claim 11  by incorporating at least one functional group in the structure of the polyfarnesene, wherein the polyfarnesene is a farnesene interpolymer. 
     
     
         18 . The functionalized farnesene interpolymer of  claim 17 , wherein the at least one functional group comprises an ethylenically unsaturated mono- or di-functional carboxylic acid, an ethylenically unsaturated mono- or di-functional carboxylic acid anhydride, a salt thereof or an ester thereof. 
     
     
         19 . The functionalized farnesene interpolymer of  claim 17 , wherein the at least one functional group is in an amount of at least about 1 wt. % and less than about 40 wt. %, based on the total weight of the farnesene interpolymer. 
     
     
         20 . A polyfarnesene composition comprising the functionalized farnesene interpolymer of  claim 17  and at least one additive. 
     
     
         21 . The polyfarnesene composition of  claim 20 , wherein the at least one additive is selected from the group consisting of fillers, grafting initiators, tackifiers, slip agents, anti-blocking agents, plasticizers, antioxidants, blowing agents, blowing agent activators, UV stabilizers, acid scavengers, colorants or pigments, coagents, lubricants, antifogging agents, flow aids, processing aids, extrusion aids, coupling agents, cross-linking agents, stability control agents, nucleating agents, surfactants, solvents, flame retardants, antistatic agents, and combinations thereof. 
     
     
         22 . The polyfarnesene composition of  claim 20 , wherein the at least one additive is selected from the group consisting of fillers, colorants or pigments, coupling agents, and combinations thereof.