Polyfarnesenes
View Patent ↗Provided herein are polyfarnesenes such as farnesene homopolymers derived from a farnesene and farnesene interpolymers derived from a farnesene and at least a vinyl monomer; and the processes of making and using the polyfarnesenes. The farnesene homopolymer can be prepared by polymerizing the farnesene in the presence of a catalyst. In some embodiments, the farnesene is prepared from a sugar by using a microorganism.
1. A hydrogenated polyfarnesene prepared by:
(a) polymerizing a farnesene in the presence of a catalyst to form a polyfarnesene; and
(b) hydrogenating at least a portion of double bonds in the polyfarnesene in the presence of a hydrogenation reagent to form the hydrogenated polyfarnesene,
wherein the polyfarnesene prepared by step (a) 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′):
Y has formula (IX′):
wherein R′ has formula (XI):
R 2 has formula (XII):
R 3 has formula (XIII):
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, and
wherein formula (I′) is in an amount of at most about 80 wt. % and formula (II′) is in an amount from about 5 wt. % to about 99 wt. %, based on a total weight of the polyfarnesene.
2. The hydrogenated polyfarnesene of claim 1 , wherein a portion of the double bonds in the polyfarnesene is hydrogenated.
3. The hydrogenated polyfarnesene of claim 1 , wherein the polyfarnesene is completely hydrogenated.
4. The hydrogenated polyfarnesene of claim 1 , wherein the farnesene is copolymerized with a vinyl monomer to form a farnesene copolymer.
5. The hydrogenated polyfarnesene of claim 4 , wherein the vinyl monomer is styrene.
6. The hydrogenated polyfarnesene of claim 5 , wherein the polyfarnesene is a block copolymer.
7. The hydrogenated polyfarnesene of claim 1 , wherein the farnesene is α-farnesene or β-farnesene or a combination thereof.
8. The hydrogenated polyfarnesene of claim 1 , wherein the farnesene is prepared by a microorganism.
9. The hydrogenated polyfarnesene of claim 1 , wherein the farnesene is derived from a monosaccharide, disaccharide, polysaccharide or a combination thereof.
10. The hydrogenated polyfarnesene of claim 1 , wherein the farnesene is derived from glucose, galactose, mannose, fructose, ribose, sucrose, lactose, maltose, trehalose, cellobiose, starch, glycogen, cellulose, chitin or a combination thereof.
11. The hydrogenated polyfarnesene of claim 1 , wherein the catalyst comprises an organolithium reagent, a Ziegler-Natta catalyst, a Kaminsky catalyst, or a metallocene catalyst.
12. The hydrogenated polyfarnesene of claim 11 , wherein the catalyst comprises an organolithium reagent and 1,2-bis(dimethylamino)ethane.
13. The hydrogenated polyfarnesene of claim 12 , wherein the organolithium reagent is n-butyl lithium or sec-butyl lithium.
14. The hydrogenated polyfarnesene of claim 1 , wherein the hydrogenation reagent is hydrogen in the presence of a hydrogenation catalyst.
15. The hydrogenated polyfarnesene of claim 14 , wherein the hydrogenation catalyst is 10% Pd/C.
16. The hydrogenated polyfarnesene of claim 1 , wherein m is from 1 to about 100,000; and a mole percent ratio of X to Y is from about 1:4 to about 100:1.
17. The hydrogenated polyfarnesene of claim 1 , wherein m is 0 and the polyfarnesene is a farnesene homopolymer.
18. The hydrogenated polyfarnesene of claim 1 , wherein m is from 1 to about 100,000 and the polyfarnesene is a random farnesene interpolymer.
19. The hydrogenated polyfarnesene of claim 1 , wherein m is from 1 to about 100,000 and the polyfarnesene is a block farnesene interpolymer.
20. The hydrogenated polyfarnesene of claim 19 , wherein the block farnesene interpolymer according to formula X′ comprises one block of one or more X and two blocks each of one or more Y and wherein the one block of one or more X is between the two blocks each of one or more Y.