Plasticized compositions containing estolide compounds
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. A plasticized composition comprising at least one polymeric material and at least one estolide compound, wherein said at least one estolide compound is selected from compounds of Formula II:
wherein
m is an integer greater than or equal to 1;
n is an integer greater than or equal to 0;
R 1 is a saturated or unsaturated alkyl that is branched or unbranched, and substituted with one or more epoxy groups and/or hydroxyl groups;
R 2 is selected from hydrogen and optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; and
R 3 and R 4 , independently for each occurrence, are selected from optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched, and
wherein the at least one polymeric material is selected from one or more of a polyvinyl polymer, a polyolefin, an acrylate polymer, a methacrylate polymer, a styrene polymer, a polyester, a polyamide, a polycarbonate, a polyurethane, a polysulfide, a silicone, an elastomer, or a rubber.
2. The plasticized composition according to claim 1 , wherein
R 3 and R 4 , independently for each occurrence, are selected from optionally substituted C 1 to C 20 alkyl that is saturated or unsaturated, and branched or unbranched.
3. The plasticized composition according to claim 2 , wherein R 3 and R 4 are unsubstituted and unbranched.
4. The plasticized composition according to claim 3 , wherein R 3 and R 4 are saturated.
5. The plasticized composition according to claim 1 , wherein m is 1.
6. The plasticized composition according to claim 1 , wherein n is an integer selected from 0 to 6.
7. The plasticized composition according to claim 1 , wherein R 1 is, independently for each occurrence, selected from a branched or unbranched C 1 to C 20 alkyl that is saturated and substituted with one or more epoxy groups and/or hydroxyl groups.
8. The plasticized composition according to claim 7 , wherein R 1 is, independently for each occurrence, selected from C 9 alkyl and C 10 alkyl which are saturated, unbranched, and substituted with one or more epoxy groups and/or hydroxyl groups.
9. The plasticized composition according to claim 1 , wherein R 2 is hydrogen.
10. The plasticized composition according to claim 1 , wherein R 2 is a branched or unbranched C 1 to C 20 alkyl that is saturated or unsaturated.
11. The plasticized composition according to claim 1 , wherein R 3 , independently for each occurrence, is selected from unsubstituted C 1 -C 18 alkyl that is saturated and unbranched.
12. The plasticized composition according to claim 1 , wherein R 4 , independently for each occurrence, is selected from unsubstituted C 1 -C 18 alkyl that is saturated and unbranched.
13. The plasticized composition according to claim 1 , wherein the at least one polymeric material is selected from one or more of a copolymer or a homopolymer.
14. The plasticized composition according to claim 1 , wherein the at least one polymeric material is biodegradable.
15. The plasticized composition according to claim 1 , wherein the at least one polymeric material is a polyester.
16. The plasticized composition according to claim 15 , wherein the at least one polymeric material is selected from one or more of polyglycolic acid, polylactic acid, polycaprolactone, polyhydroxybutyrate, polyhydroxyvalerate, or polyhydroxyvaleric acid.
17. The plasticized composition according to claim 1 , wherein the at least one polymeric material is a polyethylene.
18. The plasticized composition according to claim 17 , wherein the at least one polymeric material is selected from one or more of polyvinylacetate, poly(butylene succinate), polyvinyl alcohol, or poly-p-dioxanone.
19. The plasticized composition according to claim 4 , wherein R 3 and R 4 , independently for each occurrence, are selected from C 9 alkyl and C 10 alkyl.
20. The plasticized composition according to claim 19 , wherein R 1 is, independently for each occurrence, selected from C 9 alkyl and C 10 alkyl, which are saturated, unbranched, and substituted with one or more epoxy groups and/or hydroxyl groups.