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 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 30 mole % and an amount of the at least one vinyl monomer is less than about 70 mole %, based on the total amount of the farnesene interpolymer, wherein the farnesene is α-farnesene or β-farnesene or a combination thereof, and wherein the-at least one vinyl monomer is a substituted or unsubstituted vinyl halide, vinyl ether, acrylonitrile, acrylic ester, methacrylic ester, acrylamide, methacrylamide, or a combination thereof.
2. The method of claim 1 , wherein the farnesene is prepared by a microorganism.
3. The method of claim 1 , wherein the farnesene is derived from a simple sugar.
4. The method of claim 1 , wherein the catalyst is a Ziegler-Natta catalyst, a Kaminsky catalyst, a metallocene catalyst, an organolithium reagent or a combination thereof.
5. The method of claim 1 , wherein the catalyst is a Ziegler-Natta catalyst.
6. The method of claim 1 , wherein the catalyst is a metallocene catalyst.
7. The method of claim 1 , wherein the catalyst is a Kaminsky catalyst.
8. The method of claim 1 , wherein the catalyst is an organolithium reagent.
9. 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 30 mole % and an amount of the at least one vinyl monomer is less than about 70 mole %, based on the total amount of the farnesene interpolymer, and wherein the at least one vinyl monomer is a substituted or unsubstituted vinyl halide, vinyl ether, acrylonitrile, acrylic ester, methacrylic ester, acrylamide, methacrylamide, or a combination thereof.
10. The method of claim 9 , wherein the catalyst is a Ziegler-Natta catalyst, a Kaminsky catalyst, a metallocene catalyst, an organolithium reagent or a combination thereof.
11. The method of claim 9 , wherein the catalyst is a Ziegler-Natta catalyst.
12. The method of claim 9 , wherein the catalyst is a metallocene catalyst.
13. The method of claim 9 , wherein the catalyst is a Kaminsky catalyst.
14. The method of claim 9 , wherein the catalyst is an organolithium reagent.
15. A farnesene interpolymer prepared by the method of claim 1 .
16. A farnesene interpolymer prepared by the method of claim 9 .
17. A polymer composition comprising the farnesene interpolymer of claim 15 .
18. The polymer composition of claim 17 further comprising at least one additive.
19. The polymer composition of claim 18 , wherein the at least one additive is a filler, grafting initiator, tackifier, slip agent, anti-blocking agent, plasticizer, antioxidant, blowing agent, blowing agent activator, UV stabilizer, acid scavenger, colorant or pigment, coagent, lubricant, antifogging agent, flow aid, processing aid, extrusion aid, coupling agent, cross-linking agent, stability control agent, nucleating agent, surfactant, flame retardant, antistatic agent, or a combination thereof.
20. The polymer composition of claim 17 further comprising a second polymer.
21. The polymer composition of claim 20 , wherein a weight ratio of the farnesene interpolymer to the second polymer is from about 1:99 to about 99:1.
22. The polymer composition of claim 20 , wherein the second polymer is a polyolefin, polyurethane, polyester, polyamide, styrenic polymer, phenolic resin, polyacrylate, polymethacrylate, or a combination thereof.
23. A polymer composition comprising the farnesene interpolymer of claim 16 .
24. The polymer composition of claim 23 further comprising at least one additive.
25. The polymer composition of claim 24 , wherein the at least one additive is a filler, grafting initiator, tackifier, slip agent, anti-blocking agent, plasticizer, antioxidant, blowing agent, blowing agent activator, UV stabilizer, acid scavenger, colorant or pigment, coagent, lubricant, antifogging agent, flow aid, processing aid, extrusion aid, coupling agent, cross-linking agent, stability control agent, nucleating agent, surfactant, flame retardant, antistatic agent, or a combination thereof.
26. An article comprising the farnesene interpolymer of claim 15 .
27. The article of claim 26 , wherein the article is a molded article, film, sheet or foam.
28. The article of claim 26 , wherein the article is a molded article selected from the group consisting of toys, grips, soft touch handles, bumper rub strips, floorings, auto floor mats, wheels, casters, furniture and appliance feet, tags, gaskets, automotive doors, bumper fascia, grill components, rocker panels, hoses, linings, office supplies, seals, liners, diaphragms, tubes, lids, stoppers, plunger tips, delivery systems, kitchen wares, shoes, shoe bladders, and shoe soles.
29. 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 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, hydrocarbyl, substituted hydrocarbyl, heterocyclyl, substituted heterocyclyl, 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 30 mole %, based on the total amount of the farnesene interpolymer, and 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.
30. The farnesene interpolymer of claim 29 , wherein the farnesene interpolymer is a random interpolymer.
31. The method of claim 1 , comprising copolymerizing the farnesene and the at least one vinyl monomer with at least one C 2-20 olefin.
32. The method of claim 31 , wherein the at least one C 2-20 olefin includes ethylene, propylene, isobutylene, 1-butene, 1-pentene, 1-hexene, 4-methyl-1-pentene, and 1-octene.
33. The method of claim 9 , comprising copolymerizing the farnesene and the at least one vinyl monomer with at least one C 2-20 olefin.
34. The method of claim 33 , wherein the at least one C 2-20 olefin includes ethylene, propylene, isobutylene, 1-butene, 1-pentene, 1-hexene, 4-methyl-1-pentene, and 1-octene.