Sulfurized estolides and methods of making and using the same
Provided herein are compounds of the formula: in which n is an integer equal to or greater than 1; m is an integer equal to or greater than 1; R 2 is selected from hydrogen and optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; and R 1 , R 3 , and R 4 , independently for each occurrence, are selected from optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched, wherein at least one of R 1 , R 2 , R 3 , or R 4 is sulfurized or epoxidized. Also provided are compositions containing the compounds and methods of making both the compounds and compositions thereof.
1. At least one compound of Formula I:
wherein
W 1 , W 2 , W 3 , W 4 , W 5 , W 6 , and W 7 , independently for each occurrence, are selected from —CH 2 —, —CH═CH—, —CHR 5 —, and
provided that at least one of W 1 , W 2 , W 3 , W 4 , W 5 , W 6 , or W 7 is —CHR 5 — or
R 5 is selected from —S v R 6 , wherein v is an integer selected from 1 to 8 and R 6 is selected from hydrogen and an estolide residue;
T is S;
z is an integer selected from 0 to 15;
p is an integer selected from 0 to 15;
q is an integer selected from 0 to 15;
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 equal to or greater than 0; and
R 2 is selected from hydrogen and 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.
2. The at least one compound according to claim 1 , wherein at least one of
W 1 , W 2 , or W 3 is —CHR 5 — or
3. The at least one compound according to claim 1 , wherein W 3 is —CH 2 —.
4. The at least one compound according to claim 1 , wherein W 1 is —CH 2 —.
5. The at least one compound according to claim 1 , wherein W 2 is selected from —CHR 5 — and
6. The at least one compound according to claim 5 , wherein W 2 is selected from —CHR 5 —, and R 5 is selected from —S v R 6 .
7. The at least one compound according to claim 1 , wherein R 6 is an estolide residue.
8. The at least one compound according to claim 1 , wherein v is an integer selected from 1 and 2.
9. The at least one compound according to claim 5 , wherein W 2 is selected from
10. The at least one compound according to claim 1 , wherein z is an integer selected from 2 to 8.
11. The at least one compound according to claim 10 , wherein z is 6.
12. The at least one compound according to claim 1 , wherein p is an integer selected from 1 to 5.
13. The at least one compound according to claim 12 , wherein p is 1.
14. The at least one compound according to claim 1 , wherein q is an integer selected from 1 to 8.
15. The at least one compound according to claim 1 , wherein q is selected from 0 and 1.
16. The at least one compound according to claim 1 , wherein q is an integer selected from 5 and 6.
17. The at least one compound according to claim 1 , wherein W 2 is selected from —CHR 5 —, R 5 is selected from —S v R 6 , and p is an integer selected from 1 and 2.
18. The at least one compound according to claim 17 , wherein v, independently for each occurrence, is an integer selected from 1 and 2.
19. The at least one compound according to claim 1 , wherein W 2 is selected from
and p is 1.
20. The at least one compound according to claim 1 , wherein the compound is selected from at least one compound according to Formula III:
21. The at least one compound according to claim 1 , wherein n is an integer selected from 0 to 12.
22. The at least one compound according to claim 21 , wherein n is an integer selected from 0 to 8.
23. The at least one compound according to claim 22 , wherein n is an integer selected from 0 to 6.
24. The at least one compound according to claim 1 , wherein n is equal to or greater than 1.
25. The at least one compound according to claim 1 , wherein x+y is, independently for each chain, an integer selected from 13 to 19.
26. The at least one compound according to claim 25 , wherein x+y is, independently for each chain, an integer selected from 13 to 15.
27. The at least one compound according to claim 1 , wherein x+y is 15 for at least one chain.
28. The at least one compound according to claim 1 , wherein R 2 is a branched or unbranched C 1 to C 20 alkyl that is saturated or unsaturated.
29. The at least one compound according to claim 1 , wherein R 2 is selected from methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decanyl, undecanyl, dodecanyl, tridecanyl, tetradecanyl, pentadecanyl, hexadecanyl, heptadecanyl, octadecanyl, nonadecanyl, and icosanyl, which are saturated or unsaturated and branched or unbranched.
30. The at least one compound according to claim 28 , wherein R 2 is selected from C 6 to C 12 alkyl.
31. The at least one compound according to claim 30 , wherein R 2 is 2-ethylhexyl.
32. The at least one compound according to claim 1 , wherein R 2 is hydrogen.
33. The at least one compound according to claim 1 , wherein R 2 is an unsubstituted alkyl that is saturated or unsaturated, and branched or unbranched.
34. The at least one compound according to claim 20 , wherein z is 6 and q is an integer selected from 0 to 6.