Elastomer derived from epoxidized vegetable oil

Patent metadata

Field	Value
Publication number	US-9765182-B2
Application number	US-201414478185-A
Country	US
Kind code	B2
Filing date	Sep 5, 2014
Priority date	Sep 20, 2013
Publication date	Sep 19, 2017
Grant date	Sep 19, 2017

Abstract

Disclosed is an elastomer synthesized by a reacting epoxidized vegetable oil with carboxylic acid to form the elastomer compound. More specifically, disclosed herein is an elastomer compound having a polyester component. The method for making the elastomer comprises mixing a polybasic acid with an alcohol solvent to form a solution, reacting said solution having carboxylic groups with epoxidized vegetable oil, and heating the solution at a range of approximately 50° C. to 80° C., wherein an amorphous polyester elastomer is formed. Also disclosed is an elastomer foam product formed by a reacting epoxidized vegetable oil with carboxylic acid.

First claim

The invention claimed is:

1. A method for making an elastomer compound having an amorphous polyester component, the method comprising:
a) mixing a dicarboxylic acid or tricarhoxylic acid with an alcohol solvent to form a solution,
b) reacting said solution having carboxylic groups with epoxidized vegetable oil wherein the epoxy group present in the epoxidized vegetable oil to the carboxylic group present in the solution is at a molar ratio of approximately 1:0.8 to approximately 1:1.5,
c) heating the solution at a range of approximately 50°C to 80° C., wherein an amorphous polyester is synthesized; and
d) extracting the alcohol solvent to leave an elastomer compound having an amorphous polyester component, wherein the elastomer compound has a glass transition temperature of between −21° C. and −13° C.; wherein said extracting is vacuum extraction, membrane extraction, or centrifugation extraction.

2. The method of claim 1 wherein the elastomer compound has an amorphous polyester component is synthesized without a catalyst.

3. The method of claim 1 wherein the epoxidized vegetable oil is epoxidized soybean oil.

4. The method of claim 3 wherein the epoxidized soybean oil has 6%-7% oxirane moieties by weight.

5. The method of claim 1 wherein the epoxidized vegetable oil is epoxidized linseed oil.

6. The method of claim 1 wherein the tricarboxylic acid is citric acid.

7. The method of claim 6 wherein the citric acid is in monohydrate form.

8. The method of claim 6 wherein the citric acid is in an anhydrous form.

9. The method of claim 1 wherein the dicarboxylic acid or tricarboxylic acid is selected from the group consisting of fumaric acid, adipic acid, malic acid, succinic acid, suberic acid, sebacic acid, dodecanedioic acid, glucaric acid, glutamic acid, glutaric acid, azelaic acid, and tartaric acid.

10. The method of claim 1 wherein the alcohol solvent is ethanol, butanol, or isopropanol.

11. An elastomer having an amorphous polyester component produced by the method described in claim 1 .

12. A method for producing a foam elastomer material having a polyester component, the method comprising:
a) mixing a dicarboxylic acid or tricarboxylic acid with an alcohol solvent to form a solution,
b) reacting said solution having carboxylic groups with epoxidized vegetable oil wherein the epoxy group present in the epoxidized vegetable oil to the carboxylic group present in the solution is at a molar ratio of approximately 1:0.8 to, approximately 1:1.5,
c) heating the solution at a range of approximately 50° C. to 80° C. and
d) extracting the alcohol solvent and adding salt to the solution wherein a foam elastomer material having an amorphous polyester component formed; wherein said extracting is vacuum extraction, membrane extraction, or centrifugation extraction.

13. The method of claim 12 wherein the foam elastomer material having an amorphous polyester component is synthesized without a catalyst.

14. The method of claim 12 wherein the epoxidized vegetable oil is epoxidized soybean oil.

15. The method of claim 14 wherein the epoxidized soybean oil has 6%-7% oxirane moieties by weight.

16. The method of claim 12 wherein the epoxidized vegetable oil is epoxidized linseed oil.

17. The method of claim 13 wherein the tricarboxylic acid is citric acid.

18. The method of claim 17 wherein the citric acid is in monohydrate form.

19. The method of claim 17 wherein the citric acid is in an anhydrous form.

20. The method of claim 12 wherein the dicarboxylic acid or tricarboxylic acid is selected from the group consisting of fumaric acid, adipic acid, malic acid, succinic acid, suberic acid, sebacic acid, dodecanedioic acid, glucaric acid, glutamic acid, glutaric acid, azelaic acid, and tartaric acid.

21. The method of claim 12 wherein the alcohol solvent is ethanol, butanol, or isopropanol.

22. A foam elastomer having a polyester component produced by the method described in claim 12 .

23. The method of claim 1 wherein the epoxidized vegetable oil is epoxidized safflower oil, epoxidized corn oil, epoxidized sunflower oil, epoxidized olive oil, epoxidized canola oil, epoxidized sesame oil, epoxidized cottonseed oil, epoxidized palm oil, epoxidized rapeseed oil, epoxidized tung oil, epoxidized peanut oil, epoxidized cuphea oil, epoxidized milkweed oil, or epoxidized salicornia oil.

24. The method of claim 23 wherein the epoxidized vegetable oil is epoxidized corn oil.

25. A method for making an elastomer compound having an amorphous polyester component, the method consisting of:
a) mixing a dicarboxylic acid or tricarboxylic acid with an alcohol solvent to form a solution,
b) reacting said solution having carboxylic groups with epoxidized vegetable oil wherein the epoxy group present in the epoxidized vegetable oil to the carboxylic group present in the solution is at a molar ratio of approximately 1:0.8 to approximately 1:1.5,
c) heating the solution at a range of approximately 50° C. to 80° C., wherein an amorphous polyester is synthesized; and
d) extracting the alcohol solvent to leave an elastomer compound having an amorphous polyester component, wherein the elastomer compound has a glass transition temperature of between −21 20 C. and −13° C.; wherein said extracting is vacuum extraction, membrane extraction, or centrifugation extraction.

26. A method for producing a foam elastomer material having a polyester component, the method consisting of:
a) mixing a dicarboxylic acid or tricarboxylic acid with an alcohol solvent to form a solution,
b) reacting said solution having carboxylic groups with epoxidized vegetable oil wherein the epoxy group present in the epoxidized vegetable oil to the carboxylic group present in the solution is at a molar ratio of approximately 1:0.8 to approximately 1:1.5,
c) heating the solution at a range of approximately 50° C. to 80° C.; and
d) extracting the alcohol solvent and adding salt to the solution wherein a foam elastomer material having an amorphous polyester component formed; wherein said extracting is vacuum extraction, membrane extraction, or centrifugation extraction.

Assignees

• Us Agriculture

Inventors

• Liu Zengshe

Classifications

• C08G63/42

  Cyclic ethers (C08G59/00 takes precedence); Cyclic carbonates; Cyclic sulfites; Cyclic orthoesters · CPC title

• C08J2367/00

  Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers · CPC title

• C08J2201/0502

  the liquid phase being organic · CPC title

• C08J9/286

  the liquid phase being a solvent for the monomers but not for the resulting macromolecular composition, i.e. macroporous or macroreticular polymers · CPC title

• C08G63/81 Primary

  using solvents (C08G63/79 takes precedence) · CPC title