Estolide and lubricant compositions that contain ene and diels alder compounds
Provided herein are compositions containing at least one estolide compound and at least one ene and/or Diels Alder compound. In certain embodiments, the addition of at least one ene and/or Diels Alder compound to an estolide-containing composition may improve the cold temperature, viscometric, and/or anti-wear properties of the composition.
1. A lubricant composition comprising:
at least one estolide compound; and
at least one compound selected from compounds of Formula II:
wherein
Y 1 is an unsubstituted C 5 to C 10 alkyl that is saturated and unbranched;
Y 2 , Y 3 , and Y 4 , independently for each occurrence, are selected from unsubstituted C 4 to C 10 alkylene that is saturated and unbranched;
U 1 and U 2 , independently for each occurrence, are selected from hydrogen and —C(═O)OR 10 ;
R 9 and R 10 , independently for each occurrence, are selected from optionally substituted alkyl that is saturated and branched or unbranched; and
R 5 and R 6 are hydrogen, or R 5 and R 6 , taken together with the carbons to which they are attached, form an optionally substituted cycloalkyl,
wherein the dashed line represents a single bond, and wherein at least one of U 1 or U 2 is —C(═O)OR 10 , and
wherein the composition exhibits a kinematic viscosity that is greater than the kinematic viscosity of the at least one estolide compound, and wherein the composition exhibits a pour point that is lower than the pour point of the at least one estolide compound.
2. The lubricant composition according to claim 1 , wherein Y 1 is selected from C 5 alkyl and C 8 alkyl.
3. The lubricant composition according to claim 1 , wherein Y 2 is selected from C 7 alkylene and C 10 alkylene.
4. The lubricant composition according to claim 1 , wherein Y 3 is selected from C 5 alkylene and C 6 alkylene.
5. The lubricant composition according to claim 4 , wherein U 1 is hydrogen.
6. The lubricant composition according to claim 1 , wherein Y 3 is selected from C 7 alkylene and C 8 alkylene.
7. The lubricant composition according to claim 6 , wherein U 1 is —C(═O)OR 10 .
8. The lubricant composition according to claim 1 , wherein Y 4 is selected from C 5 alkylene and C 6 alkylene.
9. The lubricant composition according to claim 8 , wherein U 2 is hydrogen.
10. The lubricant composition according to claim 1 , wherein Y 4 is selected from C 7 alkylene and C 8 alkylene.
11. The lubricant composition according to claim 10 , wherein U 2 is —C(═O)OR 10 .
12. The lubricant composition according to claim 1 , wherein R 9 and R 10 , independently for each occurrence, are selected from unsubstituted C 1 to C 20 alkyl that is saturated and branched or unbranched.
13. The lubricant composition according to claim 12 , wherein R 9 and R 10 , independently for each occurrence, are selected from unsubstituted C 6 to C 12 alkyl that is saturated and branched.
14. The lubricant composition according to claim 13 , wherein R 9 and R 10 are 2-ethylhexyl.
15. The lubricant composition according to claim 1 , wherein R 5 and R 6 are hydrogen.
16. The lubricant composition according to claim 1 , wherein R 5 and R 6 , taken together with the carbons to which they are attached, form a substituted C 6 cycloalkyl.
17. The lubricant composition according to claim 1 , wherein the at least one estolide compound is selected from compounds of Formula V:
wherein
x is, independently for each occurrence, an integer selected from 1 to 10;
y is, independently for each occurrence, an integer selected from 1 to 10;
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 of said at least one estolide compound is unsubstituted.
18. The lubricant composition according to claim 17 , wherein R 2 is an unsubstituted C 6 to C 12 alkyl that is saturated or unsaturated, and branched.
19. The lubricant composition according to claim 18 , wherein R 2 is saturated.
20. The lubricant composition according to claim 19 , wherein R 2 is 2-ethylhexyl.
21. The lubricant composition according to claim 17 , wherein R 1 is an unbranched C 1 to C 20 alkyl that is unsubstituted, and saturated or unsaturated.
22. The lubricant composition according to claim 21 , wherein R 1 is saturated.
23. The lubricant composition according to claim 17 , wherein y is, independently for each occurrence, an integer selected from 7 and 8.
24. The lubricant composition according to claim 17 , wherein x is, independently for each occurrence, an integer selected from 7 and 8.