IP Library Granted Patent US 9,546,336
Granted Patent B2
US 9,546,336 · App. 15/174,558 · Granted Jan 17, 2017

Compositions comprising estolide compounds and methods of making and using the same

Inventors: Travis Thompson (Anaheim, CA); Jakob Bredsguard (Lake Forest, CA); Jeremy Forest (Honolulu, HI)
Assignee: Biosynthetic Technologies, LLC.
C10M111/04B21J3/00C09K5/00C09K5/044C09K5/045C10M105/36C10M105/42C10M129/72C10M143/06C10M169/041C10M169/042C10M171/008C09K2205/12C10M2205/026C10M2207/02C10M2207/042C10M2207/10C10M2207/28C10M2207/2825C10M2207/301C10M2223/04C10M2223/043C10N2220/022C10N2220/30C10N2220/301C10N2220/302C10N2220/303C10N2220/305C10N2220/306C10N2240/30
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Quick Facts
Patent No.
US 9,546,336
App. No.
15/174,558
Granted
Jan 17, 2017
Kind
B2
Abstract

Provided herein are compositions comprising at least one estolide compound of formula: in which n is an integer equal to or greater than 0; m is an integer equal to or greater than 1; R 1 , independently for each occurrence, is selected from optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; R 2 is selected from hydrogen and optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; and R 3 and R 4 , independently for each occurrence, are selected from optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched. Also provided are uses of the compositions described herein.

Claims (53)

1. A composition comprising:

at least one polybutene; and

at least one estolide compound.

2. The composition according to claim 1 , wherein the at least one polybutene comprises a polyisobutylene.

3. The composition according to claim 1 , wherein the at least one polybutene has an average molecular weight of about 400 to about 1300.

4. The composition according to claim 2 , wherein the polyisobutylene has an average molecular weight of about 400 to about 1300.

5. The composition according to claim 4 , wherein the polyisobutylene has an average molecular weight of about 950.

6. The composition according to claim 2 , wherein the at least one estolide compound is selected from compounds of Formula I:

wherein

x is, independently for each occurrence, an integer selected from 0 to 20;

y is, independently for each occurrence, an integer selected from 0 to 20;

n is an integer selected from 0 to 12;

R 1 is selected from hydrogen and an optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; and

R 2 is an optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched;

wherein each fatty acid chain residue of said at least one compound is independently optionally substituted.

7. The composition according to claim 6 , wherein

x is, independently for each occurrence, an integer selected from 0 to 14;

y is, independently for each occurrence, an integer selected from 0 to 14;

n is an integer selected from 0 to 8;

R 1 is an optionally substituted C 1 to C 22 alkyl that is saturated or unsaturated, and branched or unbranched; and

R 2 is an optionally substituted C 1 to C 22 alkyl that is saturated or unsaturated, and branched or unbranched,

wherein each fatty acid chain residue is unsubstituted.

8. The composition according to claim 7 , wherein R 1 is unsubstituted and unbranched.

9. The composition according to claim 8 , wherein R 1 is saturated.

10. The composition according to claim 8 , wherein R 2 is unsubstituted, and branched or unbranched.

11. The composition according to claim 10 , wherein R 1 is saturated.

12. The composition according to claim 11 , wherein x is, independently for each occurrence, an integer selected from 7 and 8.

13. The composition according to claim 12 , wherein y is, independently for each occurrence, an integer selected from 7 and 8.

14. The composition according to claim 12 , wherein y is 0 for each occurrence.

15. A composition comprising:

at least one polyisobutylene; and

at least one estolide compound is selected from compounds of Formula I:

wherein

x is, independently for each occurrence, an integer selected from 0 to 14;

y is, independently for each occurrence, an integer selected from 0 to 14;

n is an integer selected from 0 to 8;

R 1 is an optionally substituted C 1 to C 22 alkyl that is saturated or unsaturated, and branched or unbranched; and

R 2 is an optionally substituted C 1 to C 22 alkyl that is saturated or unsaturated, and branched or unbranched,

wherein each fatty acid chain residue is unsubstituted.

16. The composition according to claim 15 , wherein the polyisobutylene has an average molecular weight of about 400 to about 1300.

17. The composition according to claim 16 , wherein the polyisobutylene has an average molecular weight of about 950.

18. The composition according to claim 15 , wherein R 1 is unsubstituted and unbranched.

19. The composition according to claim 18 , wherein R 1 is saturated.

20. The composition according to claim 15 , wherein R 2 is unsubstituted, and branched or unbranched.

21. The composition according to claim 20 , wherein R 1 is saturated.

22. The composition according to claim 21 , wherein x is, independently for each occurrence, an integer selected from 7 and 8.

23. The composition according to claim 22 , wherein y is, independently for each occurrence, an integer selected from 7 and 8.

24. The composition according to claim 22 , wherein y is 0 for each occurrence.

25. The composition according to claim 15 , further comprising at least one antioxidant.

26. The composition according to claim 25 , wherein the at least antioxidant is selected from one or more of an amine antioxidant, a phenolic antioxidant, or an organometallic antioxidant.

27. The composition according to claim 15 , further comprising at least one of a separation preventer, a stability enhancer, a surfactant, a biocide, a corrosion inhibitor, an abrasion inhibitor, a viscosity index improver, a pour point depressant, a dispersant, or an antifoaming agent.

28. The composition according to claim 15 , wherein the at least one estolide compounds comprises 25 to 95 wt. % of the composition.

29. The composition according to claim 28 , wherein the at least one polyisobutylene comprises 1 to 50 wt. % of the composition.

Assignments (2)
ASSIGNMENT OF SECURITY INTEREST Recorded Mar 23, 2018
From: BP TECHNOLOGY VENTURES INC.
To: BIOSYN HOLDINGS, LLC
Reel/Frame 045688/0600 →
SECURITY INTEREST Recorded Jan 30, 2018
From: BIOSYNTHETIC TECHNOLOGIES, LLC
To: BP TECHNOLOGY VENTURES INC.
Reel/Frame 045196/0587 →
Continuity (10)
Continuation 14829468 · Aug 18, 2015
Continuation 14676516 · Apr 1, 2015
Continuation 14100469 · Dec 9, 2013
Continuation 13754775 · Jan 30, 2013
Continuation 13587120 · Aug 16, 2012
Continuation 13531923 · Jun 25, 2012
Continuation 13404903 · Feb 24, 2012
Provisional Application 61498499 · Jun 17, 2011
Provisional Application 61569046 · Dec 9, 2011
Related Publication 20160281016A1 · Sep 29, 2016