IP Library Granted Patent US 7,868,115
Granted Patent B1
US 7,868,115 · App. 12/825,364 · Granted Jan 11, 2011

Farnesene interpolymer

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Quick Facts
Patent No.
US 7,868,115
App. No.
12/825,364
Granted
Jan 11, 2011
Kind
B1
Abstract

Provided herein are farnesene interpolymers derived from a farnesene and at least one vinyl monomer. In certain embodiments, the farnesene is α-farnesene, β-farnesene or a combination thereof. In some embodiments, the at least one vinyl monomer is ethylene, an α-olefin such as styrene, or a substituted or unsubstituted vinyl halide, vinyl ether, acrylonitrile, acrylic ester, methacrylic ester, acrylamide or methacrylamide, or a combination thereof.

Claims (30)

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′):

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, and wherein a mole percent ratio of X to Y is from about 1:4 to about 100:1.

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 3 , wherein the farnesene interpolymer is a block farnesene interpolymer.

5. The farnesene interpolymer of claim 4 , 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.

6. 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.

7. The farnesene interpolymer of claim 1 , wherein formula (I′) is in an amount of at most about 80 wt. %, based on a total weight of the farnesene interpolymer.

8. The farnesene interpolymer of claim 1 , wherein formula (II′) is in an amount from about 15 wt. % to about 99 wt. %, based on a total weight of the farnesene interpolymer.

9. A method of making the farnesene interpolymer according to claim 1 comprising copolymerizing a farnesene and at least one vinyl monomer in the presence of a catalyst, wherein a mole percent ratio of the farnesene to the at least one vinyl monomer is from about 1:4 to about 100:1, and wherein the vinyl monomer does not comprise an isoprene.

10. The method of claim 9 , wherein the farnesene is α-farnesene, β-farnesene or a combination thereof.

11. The method of claim 9 , wherein the at least one vinyl monomer is ethylene, an α-olefin, a substituted or unsubstituted vinyl halide, vinyl ether, acrylonitrile, acrylic ester, methacrylic ester, acrylamide or methacrylamide or a combination thereof.

12. The method of claim 9 , wherein the at least one vinyl monomer is styrene.

13. The method of claim 9 , wherein the farnesene is prepared by a microorganism.

14. The method of claim 9 , wherein the farnesene is derived from a simple sugar.

15. A farnesene interpolymer prepared by the method of claim 9 .

16. A method of making the farnesene interpolymer according to claim 1 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.

17. The method of claim 16 , wherein a mole percent ratio of the farnesene to the vinyl monomer is from about 1:4 to about 100:1.

18. The method of claim 16 , wherein 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.

19. The method of claim 16 , wherein the at least one vinyl monomer is styrene.

20. A farnesene interpolymer prepared by the method of claim 16 .

Assignments (18)
RELEASE OF SECURITY INTEREST Recorded Feb 14, 2023
From: NAXYRIS S.A.
To: AMYRIS, INC.
Reel/Frame 062760/0753 →
RELEASE OF SECURITY INTEREST Recorded Feb 14, 2023
From: SCHOTTENFELD OPPORTUNITIES FUND II, L.P.
To: AMYRIS, INC.
Reel/Frame 062760/0818 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 6, 2023
From: MCPHEE, DEREK JAMES
To: AMYRIS, INC.
Reel/Frame 062303/0327 →
SECURITY INTEREST Recorded Oct 18, 2022
From: AMYRIS, INC.
To: FORIS VENTURES, LLC
Reel/Frame 061703/0499 →
SECURITY INTEREST Recorded Nov 21, 2019
From: AMYRIS, INC.
To: NAXYRIS S.A.
Reel/Frame 051081/0729 →
GRANT OF PATENT SECURITY INTEREST Recorded Nov 20, 2019
From: AMYRIS, INC.
To: SCHOTTENFELD OPPORTUNITIES FUND II, L.P.
Reel/Frame 051072/0310 →
RELEASE OF SECURITY INTEREST Recorded Aug 28, 2019
From: STEGODON CORPORATION
To: AMYRIS, INC.
Reel/Frame 050206/0606 →
SECURITY INTEREST Recorded Aug 16, 2019
From: AMYRIS, INC.
To: NAXYRIS S.A.
Reel/Frame 050081/0106 →
SECURITY INTEREST Recorded Jun 16, 2016
From: HERCULES CAPITAL INC.
To: STEGODON CORPORATION
Reel/Frame 039048/0251 →
SECURITY INTEREST Recorded Jun 3, 2016
From: AMYRIS, INC.
To: HERCULES TECHNOLOGY GROWTH CAPITAL, INC.
Reel/Frame 038878/0381 →
RELEASE OF SECURITY INTEREST Recorded Mar 31, 2014
From: MAXWELL (MAURITIUS) PTE LTD
To: AMYRIS, INC.
Reel/Frame 032578/0357 →
RELEASE OF SECURITY INTEREST Recorded Mar 28, 2014
From: TOTAL ENERGIES NOUVELLES ACTIVITES USA, SAS (F/K/A TOTAL GAS & POWER USA, SAS)
To: AMYRIS, INC.
Reel/Frame 032554/0001 →
RELEASE OF SECURITY INTEREST Recorded Mar 27, 2014
From: TOTAL ENERGIES NOUVELLES ACTIVITIES USA, SAS (F/K/A TOTAL GAS & POWER USA, SAS)
To: AMYRIS, INC.
Reel/Frame 032551/0828 →
SECURITY AGREEMENT Recorded Nov 8, 2013
From: AMYRIS, INC.
To: TOTAL ENERGIES NOUVELLES ACTIVITES USA
Reel/Frame 031607/0314 →
SECURITY AGREEMENT Recorded Oct 23, 2013
From: AMYRIS, INC.
To: MAXWELL (MAURITIUS) PTE LTD
Reel/Frame 031478/0933 →
SECURITY AGREEMENT Recorded May 8, 2013
From: AMYRIS, INC.
To: TOTAL GAS & POWER USA, SAS
Reel/Frame 030378/0447 →
CHANGE OF NAME Recorded Jun 27, 2011
From: AMYRIS BIOTECHNOLOGIES, INC.
To: AMYRIS, INC.
Reel/Frame 026509/0742 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 3, 2010
From: MCPHEE, DEREK JAMES
To: AMYRIS BIOTECHNOLOGIES, INC.
Reel/Frame 024783/0171 →