Epoxidized fatty acid alkyl ester plasticizers and methods for making epoxidized fatty acid alkyl ester plasticizers

Patent metadata

Field	Value
Publication number	US-9499681-B2
Application number	US-201214429112-A
Country	US
Kind code	B2
Filing date	Nov 12, 2012
Priority date	Nov 12, 2012
Publication date	Nov 22, 2016
Grant date	Nov 22, 2016

Abstract

Epoxidized fatty acid alkyl esters and methods for making epoxidized fatty acid alkyl esters. Such epoxidized fatty acid alkyl esters can be prepared by epoxidizing fatty acid alkyl esters with an acid and a peroxide. Epoxidation can be performed under controlled reaction conditions to provide epoxidized fatty acid alkyl esters having an iodine value in the range of from 4 to 15 g I 2 /100 g of epoxidized fatty acid alkyl esters. Epoxidized fatty acid alkyl esters can be employed in plasticizer compositions, either alone or in combination with other plasticizers, such as epoxidized natural oils. Such plasticizers in turn may be used in the formation of polymeric compositions.

First claim

The invention claimed is:

1. A plasticizer composition comprising:
epoxidized fatty acid alkyl esters,
wherein said epoxidized fatty acid alkyl esters have an iodine value in the range of from 7 to 10 g I 2 /100 g of epoxidized fatty acid alkyl esters,
wherein said epoxidized fatty acid alkyl esters have an oxirane oxygen content of at least 6 weight percent based on the entire weight of the epoxidized fatty acid alkyl esters,
wherein said epoxidized fatty acid alkyl esters are prepared from esterified soybean oil,
wherein said epoxidized fatty acid alkyl esters have a hydrophilic impurities content of less than 0.8 weight percent based on the entire weight of said epoxidized fatty acid alkyl esters.

2. A polymeric composition comprising a polymeric resin and the plasticizer composition of claim 1 .

3. The polymeric composition of claim 2 , wherein said polymeric resin is a vinyl chloride resin, wherein said polymeric composition is an article of manufacture selected from the group consisting of blood bags, intravenous bags, saline solution bags, syringes, intravenous tubing, nasogastric tubing, catheter tubing, drainage tubing, examination gloves, oxygen masks, orthodontic retainers, artificial skin, and food packaging.

4. A process for producing epoxidized fatty acid alkyl esters, said process comprising:
epoxidizing fatty acid alkyl esters via controlled epoxidation by contact with an acid and an aqueous peroxide solution to form epoxidized fatty acid alkyl esters,
wherein said controlled epoxidation comprises selecting a reaction temperature, a reaction time, an aqueous peroxide solution concentration, and a peroxide solution feed rate to cause said epoxidized fatty acid alkyl esters to retain sufficient unsaturation to present an iodine value in the range of from 7 to 10 g I 2 /100 g of epoxidized fatty acid alkyl esters,
wherein said epoxidized fatty acid alkyl esters have an oxirane oxygen content of at least 6 weight percent based on the entire weight of the epoxidized fatty acid alkyl esters,
wherein said fatty acid alkyl esters are prepared by transesterifying a soybean oil,
wherein said epoxidized fatty acid alkyl esters have a hydrophilic impurities content of less than 0.8 weight percent based on the entire weight of said epoxidized fatty acid alkyl esters.

5. The process of claim 4 , wherein said reaction temperature is in the range of from 30 to 50° C., wherein said aqueous peroxide solution has a concentration of less than 40%, wherein said reaction time is greater than 6 hours, wherein said peroxide solution feed rate is in the range of from 0.3 to 4 moles of peroxide solution per molar equivalent of carbon-carbon double bonds in the fatty acid alkyl esters per hour.

6. The process of claim 4 , wherein said epoxidized fatty acid alkyl esters have the structure: R 1 —C(═O)O—R 2 , wherein R 1 is a linear or branched C 1 to C 8 alkyl group, and R 2 represents saturated, mono-unsaturated, and/or polyunsaturated C 12 to C 22 epoxidized fatty acid chains.

Assignees

• Dow Global Technologies Llc

Inventors

• Ghosh-Dastidar Abhijit
• Kaujalgikar Saurabh
• Chaudhary Bharat I

Classifications

• C07D303/04 Primary

  containing only hydrogen and carbon atoms in addition to the ring oxygen atoms · CPC title

• C07C53/126

  Acids containing more than four carbon atoms · CPC title

• C08K5/0016 Primary

  Plasticisers · CPC title

• C08K5/1515

  Three-membered rings · CPC title

• C08K5/101

  of monocarboxylic acids · CPC title