Bio-based plasticizer
View Patent ↗A plasticizer composition comprising vicinally diacylated fatty acid esters derived from renewable feedstocks, and a process for the preparation thereof, are disclosed. A composition comprising a halogen-containing polymer and a plasticizer composition comprising the vicinally diacylated fatty acid esters is also described. A method for plasticizing halogen-containing polymers, such as polyvinyl chloride (PVC) resins is provided. The plasticizer compositions may be added to PVC resins in amounts ranging between 1 and 200 phr.
1. A plasticizer composition for plasticizing halogen-containing polymers comprising at least one vicinally diacylated fatty acid ester selected from the group consisting of:
wherein R 1 and R 2 are independently selected from
m is 0, 1, 2, 3 or 4;
R 3 and R 4 are independently selected from C 1 -C 8 alkyl, phenyl, or phenyl substituted by C 1 -C 4 alkyl;
n is 0;
R 5 is defined as in R 1 ; and
R 6 is defined as in R 1 .
2. The composition of claim 1 , wherein at least one vicinally diacylated fatty acid ester is derived from diol.
3. The composition of claim 2 , wherein the diol is selected from the group consisting of ethylene glycol, 1,3-propanediol, propylene glycol, 1,4-butanediol, and 1,6-hexanediol.
4. The composition of claim 1 , wherein at least one vicinally diacylated fatty acid ester is or comprises vicinally diacetylated stearic acid diester.
5. The composition of claim 1 , wherein said at least one vicinally diacylated fatty acid ester is derived from glycerol acetates selected from the group consisting of glycerol monoacetates and glycerol diacetates.
6. The composition of claim 1 , wherein said at least one vicinally diacylated fatty acid ester is or comprises vicinally diacetylated stearic acid monoglyceride diacetate or vicinally diacetylated stearic acid diglyceride monoacetate.
7. The composition of claim 1 , wherein at least one vicinally diacylated fatty acid ester is derived from vegetable oil.
8. The composition of claim 7 , wherein the vegetable oil is selected from the group consisting of soybean oil, palm oil, olive oil, cotton seed oil, linseed oil, safflower oil, sunflower oil, canola oil, rapeseed oil, jatropha oil, algae oil, tall oil, corn oil, tung oil, and mixtures of any two or more thereof.
9. The composition of claim 1 , wherein at least one vicinally diacylated fatty acid ester comprises fatty acid derived from vegetable oil.
10. The composition of claim 9 , wherein the fatty acid derived from vegetable oil is selected from the group consisting of oleic acid, linoleic acid, and linolenic acid.
11. The composition of claim 1 , wherein at least one vicinally diacylated fatty acid ester comprises stearic acid.
12. A lubricant comprising at least one vicinally diacylated fatty acid ester of claim 1 .
13. The lubricant of claim 12 , further comprising lubrication oil.
14. The lubricant of claim 12 wherein the vicinally diacylated fatty acid ester is diacylated with acylated agents selected from acetic anhydride, maleic anhydride, phthalic anhydride and mixtures thereof.
15. The lubricant of claim 14 wherein the acylated agent is acetic anhydride.
16. A process for preparing vicinally diacylated fatty acid ester of general formula (I):
wherein R 1 and R 2 are independently selected from
m is 0, 1, 2, 3 or 4; and
R 3 is C 1 -C 8 alkyl, phenyl, or phenyl substituted by C 1 -C 4 alkyl;
the process comprising the steps of:
(i) transesterifying epoxidized monoester of fatty acid with diol to provide a composition comprising epoxidized fatty acid diester;
(ii) acylating the epoxidized fatty acid diester or the composition containing the same with anhydride.
17. A product made by the process according to claim 16 .
18. A plasticizer composition for plasticizing halogen-containing polymers comprising at least one vicinally diacylated fatty acid ester selected from esters of formula (I):
wherein R 1 and R 2 are independently selected from
m is 0, 1, 2, 3 or 4; and
R 3 is independently selected from C 1 -C 8 alkyl, phenyl, or phenyl substituted by C 1 -C 4 alkyl.
19. A plasticizer composition for plasticizing halogen-containing polymers comprising at least one vicinally diacylated fatty acid ester selected from the group consisting of:
wherein R 1 and R 2 are independently selected from
m is 0, 1, 2, 3 or 4;
R 3 and R 4 are independently selected from C 1 -C 8 alkyl, phenyl, or phenyl substituted by C 1 -C 4 alkyl;
n is 0 or 1;
if n is 1,
R 5 is defined as in R 4 ; or,
if n is 0,
R 5 is defined as in R 1 ; and
R 6 is defined as in R 1 .
20. A plasticizer composition for plasticizing halogen-containing polymers comprising at least one vicinally diacylated fatty acid ester selected from the group consisting of:
wherein R 1 and R 2 are independently selected from
m is 0, 1, 2, 3 or 4;
R 3 and R 4 are independently selected from C 1 -C 8 alkyl, phenyl, or phenyl substituted by C 1 -C 4 alkyl;
n is 0;
R 5 is defined as in R 1 ; and
R 6 is defined as in R 1 .