Adducts of levulinic derivatives with epoxidized fatty acid esters and uses thereof
The present disclosure relates to methods of preparation of compounds resulting from the reaction of levulinic esters and epoxidized unsaturated fatty acid esters. The compounds are useful as renewable biomass-based plasticizers for a variety of polymers. Mono-, di- and tri-ketal adducts formed in a reaction between alkyl esters of levulinate and epoxidized unsaturated fatty acid esters derived from vegetable oils are also disclosed.
1. A compound having the formula:
wherein:
X is
wherein:
R 3 is a C 1 -C 10 linear or branched alkyl or alkoxyalkyl;
one of A or B is hydrogen and the other is an esterified carboxy group; and
m and n are independently integers from 0 to 20, wherein the sum of m+n is in the range from 8 to 21.
2. A compound having the formula:
wherein X is selected from the following:
wherein:
R 3 is a C 1 -C 10 linear or branched alkyl or alkoxyalkyl;
one of A or B is hydrogen and the other is an esterified carboxy group; and
m and n are independently integers from 0 to 20, wherein the sum of m+n is in the range from 8 to 21.
3. A method for preparing a compound of claim 1 , the method comprising:
a) providing an epoxidized fatty acid ester derivative and one or more of levulinate ester, levulinic acid and angelicalactone;
b) effecting the reaction between the compounds of a) in the presence of an acid catalyst, wherein the reaction results in the formation of a compound of claim 1 - 8 , or mixtures thereof.
4. A method for preparing a compound of claim 2 , the method comprising:
a) providing an epoxidized fatty acid ester derivative and one or more of levulinate ester, levulinic acid and angelicalactone;
b) effecting the reaction between the compounds of a) in the presence of an acid catalyst, wherein the reaction results in the formation of a compound of claim 1 - 8 , or mixtures thereof.
5. A plasticized polymer composition comprising:
a) a base polymer; and
b) a compound of claim 1 .
6. The plasticized polymer composition of claim 5 , wherein the base polymer is selected from the group consisting of a vinyl chloride polymer, a poly(3-hydroxylalkanoate)polymer, and a polysaccharide polymer.
7. The plasticized polymer composition of claim 6 , wherein the base polymer is vinyl chloride polymer.
8. A plasticized polymer composition comprising:
a) a base polymer; and
b) a compound of claim 2 .
9. The plasticized polymer composition of claim 8 , wherein the base polymer is selected from the group consisting of a vinyl chloride polymer, a poly(3-hydroxylalkanoate)polymer, and a polysaccharide polymer.
10. The plasticized polymer composition of claim 9 , wherein the base polymer is vinyl chloride polymer.