Bio-based estolide compositions

Patent metadata

Field	Value
Publication number	US-10562840-B2
Application number	US-201816139723-A
Country	US
Kind code	B2
Filing date	Sep 24, 2018
Priority date	Sep 28, 2017
Publication date	Feb 18, 2020
Grant date	Feb 18, 2020

Abstract

Levulinic-capped estolides having improved physical properties that make them more desirable and suitable as bio-based industrial or commercial products are disclosed. The physical properties of the disclosed estolide compositions have surprisingly low pour points that are substantially lower than previously known estolide compounds and superior to petroleum-based compounds designed for similar applications.

First claim

The claimed invention is:

1. A composition comprising at least one compound having the formula:

wherein:
x is an integer from 1 to 11 and y is 14−(x+z), 16−(x+z), or 18−(x+z);
z is 0 or 2, and if z is 2 there is a C═C double bond between the respective carbons;
n is 0 or an integer from 1 to about 9;
R is selected from the group consisting of: CHR1R2, a residual fragment of lesquerella oil, a residual fragment of castor oil, a residual fragment of erucic oil, or combinations thereof;
R1 and R2 are independently selected from hydrogen and a saturated or unsaturated, branched or straight chain, and substituted or unsubstituted hydrocarbon chain of C-1 to C-36; and
wherein the predominant species of secondary ester linkage is at the 9 position if z=0, x=6, and y=8; 10 position if z=0, x=7, and y=7; 12 position if z=2, x=7, and y=5 or z=0, x=9, and y=5; 13 position if z=0, x=10, and y=8; 14 position if z=2, x=9, and y=5 or z=0, x=11 and y=5.

2. The composition of claim 1 , wherein n is from 1 to about 5.

3. The composition of claim 1 , wherein n is from 1 to about 3.

4. The composition of claim 1 , wherein n is from 1 to about 2.

5. The composition of claim 1 , wherein R is selected from the group consisting of: 2-methylhexyl, 2-ethylhexyl, and a backbone of a triglyceride.

6. The composition of claim 1 , wherein R is a 2-ethylhexyl unit.

7. The composition of claim 1 , wherein the predominant species of secondary ester linkage is at the 9 position.

8. The composition of claim 1 , wherein the predominant species of secondary ester linkage is at the 10 position.

9. The composition of claim 1 , wherein the predominant species of secondary ester linkage is at the 12 position.

10. The composition of claim 1 , wherein the predominant species of secondary ester linkage is at the 13 position.

11. The composition of claim 1 , wherein the predominant species of secondary ester linkage is at the 14 position.

12. The composition of claim 1 , wherein the formula is:

wherein n is 0 or an integer from 1 to about 9.

13. The composition of claim 1 , wherein the formula is:

wherein n is 0 or an integer from 1 to about 9.

14. The composition of claim 1 , wherein the formula is:

wherein n is 0 or an integer from 1 to about 9.

15. The composition of claim 1 , wherein the formula is:

wherein n is 0 or an integer from 1 to about 9.

16. The composition of claim 1 , wherein the formula is:

wherein n is 0 or an integer from 1 to about 9.

17. The composition of claim 1 , wherein the formula is:

wherein R 4 is the residual fragment of erucic (x=9 and y=8 or x=10 and y=7) oil, saturated lesquerella (x=10 and y=5) oil, saturated castor (x=8 and y=5) oil, or combinations thereof.

18. The composition of claim 1 wherein the formula is:

wherein R 4 is the residual fragment of saturated lesquerella (x=9) oil, saturated castor (x=7) oil, or combinations thereof.

19. The composition of claim 1 , further comprising an effective amount of at least one other lubricating agent selected from the group consisting of: mineral or vegetable oils, other estolides, poly alpha olefins, polyol esters, oleates, diesters, other natural or synthetic fluids, and combinations thereof.

20. The composition of claim 1 , further comprising at least one additive selected from the group consisting of: detergents, corrosion inhibitors, antioxidants, viscosity modifiers, friction modifiers, pour point depressants, dispersants, anti-foam agents, antimisting agents, wax crystal modifiers, dewaxing aids, colorants, and combinations thereof.

21. The composition of claim 1 , wherein the pour point is from about −20° C. to about −55° C.

Assignees

• Us Agriculture

Inventors

• Cermak Steven C
• Isbell Terry
• Durham Amber L

Classifications

• C10M2209/1026

  use as thickening agent · CPC title

• C10N2040/30

  Refrigerators lubricants {or compressors lubricants} · CPC title

• C10N2040/08

  Hydraulic fluids, e.g. brake-fluids · CPC title

• C10N2030/20

  Colour, e.g. dyes · CPC title

• C10M2207/301

  used as base material · CPC title