Farnesene interpolymers
View Patent ↗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.
1. A farnesene interpolymer comprising one or more polymer molecules having formula (X′):
X n — Y m (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 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, hydrocarbyl, substituted hydrocarbyl, heterocyclyl, substituted heterocyclyl or a functional group containing O, N, S, P or a combination thereof, wherein the farnesene is α-farnesene or β-farnesene or a combination thereof, wherein an amount of the farnesene is greater than 20 mole %, based on the total amount of the farnesene interpolymer, wherein none of R 5 , R 6 , R 7 and R 8 of formula (IX′) is or comprises alkenyl, cycloalkenyl or alkynyl, and wherein an amount of formula (I′) is at most about 80 wt.%, based on a total weight of the farnesene interpolymer.
2. A farnesene interpolymer comprising one or more polymer molecules having formula (X′):
X n — Y m (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 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, hydrocarbyl, substituted hydrocarbyl, heterocyclyl, substituted heterocyclyl or a functional group containing O, N, S, P or a combination thereof, wherein the farnesene is α-farnesene or β-farnesene or a combination thereof, wherein an amount of the farnesene is greater than 20 mole %, based on the total amount of the farnesene interpolymer, wherein none of R 5 , R 6 , R 7 and R 8 of formula (IX′) is or comprises alkenyl, cycloalkenyl or alkynyl, and wherein an amount of formula (II′) is from about 15 wt. % to about 99 wt. %, based on a total weight of the farnesene interpolymer.
3. A farnesene interpolymer comprising one or more polymer molecules having formula (X′):
X n — Y m (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 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, hydrocarbyl, substituted hydrocarbyl, heterocyclyl, substituted heterocyclyl or a functional group containing O, N, S, P or a combination thereof, wherein the farnesene is α-farnesene or β-farnesene or a combination thereof, wherein an amount of the farnesene is greater than 20 mole %, based on the total amount of the farnesene interpolymer, wherein none of R 5 , R 6 , R 7 and R 8 of formula (IX′) is or comprises alkenyl, cycloalkenyl or alkynyl and wherein the farnesene interpolymer is a block interpolymer
4. A farnesene interpolymer prepared by a method of making a farnesene interpolymer comprising copolymerizing a farnesene and at least one vinyl monomer in the presence of a catalyst, wherein an amount of the farnesene is greater than 20 mole %, based on the total amount of the farnesene interpolymer, wherein the farnesene is α-farnesene or β-farneseneor a combination thereof, wherein the at least one vinyl monomer does not comprise a terpene, and wherein the at least one vinyl monomer is styrene.
5. A farnesene interpolymer prepared by a method of making a farnesene interpolymer comprising:
(a) making a farnesene from a simple sugar by a microorganism; and
(b) copolymerizing the farnesene and at least one vinyl monomer in the presence of a catalyst, wherein an amount of the farnesene is greater than 20 mole %, based on the total amount of the farnesene interpolymer, wherein the farnesene is α-farnesene or β-farnesene or a combination thereof, wherein the at least one vinyl monomer does not comprise a terpene, and wherein the at least one vinyl monomer is styrene.