Polyol estolides and methods of making and using the same

Patent metadata

Field	Value
Publication number	US-10065918-B2
Application number	US-201715460112-A
Country	US
Kind code	B2
Filing date	Mar 15, 2017
Priority date	Jul 9, 2013
Publication date	Sep 4, 2018
Grant date	Sep 4, 2018

Abstract

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.

First claim

The invention claimed is:

1. A composition comprising at least one saturated polyol estolide compound, wherein the at least one saturated polyol estolide compound exhibits a hydroxyl value of greater than or equal to 40 mg KOH/g, wherein the at least one saturated polyol estolide compound is selected from compounds of Formula I:

wherein
p is selected from 0 to 10;
p′ is selected from 0 to 10;
z is selected from 0 to 5;
q is, independently for each occurrence, selected from 0 to 10;
q′ is, independently for each occurrence, selected from 0 to 10;
U is, independently for each occurrence, selected from —C(R 3 ) 2 —;
U′ is, independently for each occurrence, selected from —C(R 4 ) 2 —;
Y 1 is, independently for each occurrence, selected from —C(R 5 ) 2 —, —NR 7 —, —O—, —S—, —C(O)O—, and —O(O)C—;
Y 2 is, independently for each occurrence, selected —C(R 6 ) 2 —, —NR 7 —, —O—, —S—, —C(O)O—, and —O(O)C—;
R 3 , R 4 , R 5 , R 6 , and R 7 , independently for each occurrence, are selected from hydrogen and optionally substituted alkyl that is saturated and branched or unbranched;
W 1 is, independently for each occurrence, selected from hydrogen, optionally substituted alkyl that is saturated and branched or unbranched, and —O-Q 3 ,
W 2 is, independently for each occurrence, selected from hydrogen, optionally substituted alkyl that is saturated and branched or unbranched, and —O-Q 4 ; and
Q 1 , Q 2 , Q 3 , and Q 4 , independently for each occurrence, are selected from 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 to 20;
Q 5 and Q 6 , independently for each occurrence, are selected from hydrogen and —CH 3 ;
R 1 is selected from saturated C 1 to C 20 alkyl that is branched or unbranched, and is optionally substituted; and
W 4 , W 5 , W 6 , and W 7 are —CH 2 — for each occurrence,
wherein each fatty acid chain residue of said at least one estolide compound is independently optionally substituted.

2. The composition of claim 1 , wherein the at least one saturated polyol estolide compound is selected from compounds 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 a residue selected from 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 to 20;
Q 5 and Q 6 , independently for each occurrence, are selected from hydrogen and —CH 3 ;
R 1 is selected from saturated C 1 to C 20 alkyl that is branched or unbranched, and is optionally substituted; and
W 4 , W 5 , W 6 , and W 7 are —CH 2 — for each occurrence,
wherein each fatty acid chain residue of said at least one estolide compound is independently optionally substituted.

3. The composition of claim 2 , wherein x is selected from 7 and 8 for each occurrence.

4. The composition of claim 2 , wherein y is selected from 7 and 8 for each occurrence.

5. The composition according to claim 4 , wherein Q 5 and Q 6 are —CH 3 .

6. The composition according to claim 5 , wherein n is selected from 0 to 8.

7. The composition according to claim 5 , wherein n is selected from 1 to 12.

8. The composition according to claim 5 , wherein R 1 is substituted with at least one hydroxyl group.

9. A compound is selected from 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 a residue selected from 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 to 20;
Q 5 and Q 6 , independently for each occurrence, are selected from hydrogen and —CH 3 ;
R 1 is selected from saturated C 1 to C 20 alkyl that is branched or unbranched, and is optionally substituted; and
W 4 , W 5 , W 6 , and W 7 are —CH 2 — for each occurrence,
wherein each fatty acid chain residue is independently optionally substituted with one or more hydroxyl groups.

10. The composition of claim 9 , wherein x is selected from 7 and 8 for each occurrence.

11. The composition of claim 10 , wherein y is selected from 7 and 8 for each occurrence.

12. The composition according to claim 11 , wherein Q 5 and Q 6 are —CH 3 .

13. The composition according to claim 12 , wherein n is selected from 0 to 8.

14. The composition according to claim 12 , wherein n is selected from 1 to 12.

15. The composition according to claim 12 , wherein R 1 is substituted with at least one hydroxyl group.

Assignees

• Biosynthetic Technologies Llc

Inventors

• Thompson Travis
• Forest Jeremy
• Lutz Marlon

Classifications

• C07C69/67 Primary

  of saturated acids · CPC title

• C10M105/36

  of polycarboxylic acids · CPC title

• C07C67/04

  by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds · CPC title

• A23D9/00

  Other edible oils or fats, e.g. shortenings or cooking oils (preservation of other edible oils A23B20/30) · CPC title

• C07C67/08

  by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title