Polyol estolides and methods of making and using the same
Provided herein are polyol estolide compounds. Polyol estolides may be prepared by contacting a polyol with an estolide compound. Also provided are compositions containing polyol estolides and methods of making the same.
1. At least one compound of Formula III:
wherein
z is selected from 1, 2, and 3;
q is, independently for each occurrence, an integer selected from 0 to 10;
q′ is selected from 1 and 2;
Y 1 is, independently for each occurrence, selected from —C(R 5 ) 2 —;
Y 2 is, independently for each occurrence, selected from —C(R 6 ) 2 —;
R 5 and R 6 , independently for each occurrence, are selected from hydrogen and optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched;
W 1 is, independently for each occurrence, selected from hydrogen, optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched, and —O-Q 3 ;
W 2 is, independently for each occurrence, selected from —O-Q 4 ; and
Q 1 , Q 2 , Q 3 , and Q 4 , independently for each occurrence, are selected from hydrogen and-residues represented by Formula II:
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 0 or greater than 0;
Q 5 and Q 6 , independently for each occurrence, are selected from hydrogen and —CH 3 ;
R 1 is, independently for each occurrence, selected from optionally substituted C 1 to C 20 alkyl that is saturated or unsaturated, and branched or unbranched; and
W 4 , W 5 , W 6 , and W 7 , independently for each occurrence, are selected from —CH 2 — and —CH═CH—,
wherein at least Q 1 , Q 2 and Q 4 are selected from residues of Formula II, and
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 Q 1 , Q 2 , Q 3 , and Q 4 independently for each occurrence are selected from residues of Formula II.
3. The at least one compound according to claim 1 , wherein n is an integer selected from 0 to 6.
4. The at least one compound according to claim 3 , wherein n is 0.
5. The at least one compound according to claim 3 , wherein W 5 and W 7 are —CH 2 — for each occurrence.
6. The at least one compound according to claim 5 , wherein R 1 is unsubstituted for each occurrence.
7. The at least one compound according to claim 6 , wherein R 1 is saturated for each occurrence.
8. The at least one compound according to claim 6 , wherein R 1 , independently for each occurrence, is selected from methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decanyl, which are saturated or unsaturated and branched or unbranched.
9. The at least one compound according to claim 5 , wherein
W 1 is, independently for each occurrence, selected from hydrogen and optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; and
W 2 is, independently for each occurrence, selected from —O-Q 4 .
10. The at least one compound according to claim 5 , wherein
W 1 is, independently for each occurrence, selected from —O-Q 3 ; and
W 2 is, independently for each occurrence, selected from —O-Q 4 .
11. The at least one compound according to claim 9 , wherein W 1 is hydrogen.
12. The at least one compound according to claim 1 , wherein
W 2 is —O-Q 4 ;
Q 1 , Q 2 , and Q 4 are selected from Formula II;
W 1 is hydrogen;
W 5 and W 7 are —CH 2 — for each occurrence;
x is, independently for each chain, an integer selected from 7 and 8;
y is 0 for each occurrence;
n=0.
13. The at least one compound according to claim 12 , wherein Q 5 and Q 6 are —CH 3 for each occurrence.
14. The at least one compound according to claim 9 , wherein q is an integer selected from 1 and 2.
15. The at least one compounds according to claim 9 , wherein Y 1 and Y 2 are —CH 2 — for each occurrence.
16. The at least one compound according to claim 9 , wherein q′ is 1.
17. The at least one compound according to claim 15 wherein z is 1.
18. The at least one compound according to claim 17 , wherein x is, independently for each chain, an integer selected from 7 and 8.
19. The at least one compound according to claim 18 , wherein y is, independently for each chain, an integer selected from 7 and 8.
20. The at least one compound according to claim 18 , wherein y is 0 for each occurrence.
21. At least one compound of Formula IV:
wherein
q is 0;
q′ is 0;
W 1 is hydrogen;
W 2 is —O-Q 4 , wherein Q 4 is hydrogen;
Q 2 is hydrogen; and
Q 1 is selected from a residue represented by Formula II:
wherein
x is, independently for each occurrence, an integer selected from 7 and 8;
y is, independently for each occurrence, an integer selected from 0 to 14;
n is selected from 0 to 8;
Q 5 and Q 6 , independently for each occurrence, are selected from hydrogen and —CH 3 ;
R 1 is selected from unsubstituted C 1 to C 20 alkyl that is saturated or unsaturated, and branched or unbranched; and
W 4 , W 5 , W 6 , and W 7 are —CH 2 — for each occurrence.
22. The compound according to claim 21 , wherein R 1 is selected from unsubstituted C 7 to C 17 alkyl that is saturated and unbranched.
23. The compound according to claim 21 , wherein n is selected from 0 to 4.
24. The compound according to claim 21 , wherein y is selected from 7 and 8.
25. The compound according to claim 21 , wherein y is 0.
26. The compound according to claim 25 , wherein Q 5 and Q 6 are —CH 3 .