Lauric ester compositions

• US 9,796,949 B2
• Filed: 06/16/2016
• Issued: 10/24/2017
• Est. Priority Date: 03/28/2014
• Status: Expired due to Fees

• Current Assignee: Corbion Biotech, Inc. (Corbion NV)
• Original Assignee: Terravia Holdings, Inc. (Corbion NV)
• Inventors: Dummer, Timothy, Bond, Risha
• Primary Examiner(s): Cutliff, Yate K
• Application Number:
  US15/184,992
• Publication Number:
  US 20160362638A1
• Time in Patent Office: 495 Days
• Field of Search: None
• CPC Class Codes: A61K 8/37 Esters of carboxylic acids
• CPC Class Codes: A61Q 19/10 Washing or bathing preparations
• CPC Class Codes: C07C 67/03 by reacting an ester group with a hydroxy group
• CPC Class Codes: C09D 9/005 containing organic solvents
• CPC Class Codes: C09K 3/00 Materials not provided for elsewhere
• CPC Class Codes: C09K 8/52 Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning
• CPC Class Codes: C11C 3/00 Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom sulfonated fats or oils C07C309/62; factice C08H; drying oils C09F
• CPC Class Codes: C11C 3/08 with fatty acids
• CPC Class Codes: C11D 3/188 Terpenes
• CPC Class Codes: C11D 3/2093 Esters; Carbonates
• CPC Class Codes: C11D 7/248 Terpenes
• CPC Class Codes: C11D 7/266 Esters or carbonates
• CPC Class Codes: C12P 7/625 Polyesters of hydroxy carboxylic acids
• CPC Class Codes: C12P 7/6436 Fatty acid esters

Abstract

Provided are compositions containing alkyl esters derived from triglyceride oils produced from genetically engineered microalgae. Specific embodiments relate to esters derived from oils with high C10-C12 fatty acid profile. Compositions comprising the esters include cleaning products, completion fluids, work-over fluids, drilling fluids, metal working fluids, lubricants, paints, and inks.

Claims

1. A cleaner comprising C1-C4 ester of fatty acids derived from triglyceride oil and at least one additional ingredient, the triglyceride oil produced by a microalga that is a recombinant oleaginous cell of the genus Prototheca, the oil having an altered fatty acid profile relative to an oil produced by a non-recombinant microalga of the genus Prototheca, the altered fatty acid profile having at least 10% C10:

0 and 40% C12;

0 fatty acids, the cleaner having a reduced odor compared to a cleaner where all the fatty acids are derived from vegetable or animal triglyceride oil having a fatty acid profile of at least 40% C12;

0 fatty acids.

2. The cleaner of claim 1, wherein the odor is an unpleasant odor characteristic of a C6 or C8 fatty acid or ester thereof.

3. The cleaner of claim 1, wherein the ester is a methyl, ethyl, propyl, iso-propyl, butyl, or a tert-butyl ester.

4. The cleaner of claim 1, having an altered fatty acid profile wherein C12:

0>

C10;

0>

C14;

0.

5. The cleaner of claim 1, wherein at least 50% of the fatty acids are C12:

0 fatty acids or the combined total amount of C;

10 and C;

12 fatty acids is at least 60%.

6. The cleaner of claim 1, wherein at least 15% of the fatty acids are C10:

0 fatty acids.

7. The cleaner of claim 1, wherein 15-25% of the fatty acids are C10:

0 fatty acids.

8. The cleaner of claim 1, wherein 10-15% of the fatty acids are C14:

0 fatty acids.

9. The cleaner of claim 1, wherein less than 8%, 7%, or 6% of the fatty acids are C16:

0 fatty acids.

10. The cleaner of claim 1, wherein less than 0.5% of the fatty acids are C8:

0 fatty acids.

11. The cleaner of claim 1, wherein less than 0.1%, 0.01%, or 0.001% of the fatty acids are C6:

0 fatty acids.

12. The cleaner of claim 1, comprising a terpene.

13. The cleaner of claim 1, wherein the terpene is limonene.

14. The cleaner of claim 1 wherein the cleaner is an adhesive remover, a driveway cleaner, a degreaser, a graffiti remover, hand cleaner, a waterless hand cleaner, a paint brush cleaner, a paint stripper, a varnish remover, a rubber tire remover, a wipe, a bug remover, a tar remover, a car wash cleaner, a parts cleaner, an engine cleaner, a fuel system additive, a rig wash, a heavy residue cleaner, a down-hole cleaner, a concrete down-hole cleaner, an ink roller cleaner, a screen printing ink wash, or a cleaner for paints, inks, coatings, sealants, elastomers, or polymers.

22. The cleaner of claim 1, wherein the recombinant oleaginous cell is a Prototheca moriformis cell.

15. A method for preparing a cleaner, the cleaner comprising C1-C4 esters of fatty acids derived from triglyceride oil, the triglyceride oil produced by a microalga that is a recombinant oleaginous cell of the genus Prototheca, the oil having an altered fatty acid profile relative to an oil produced by a non-recombinant microalga of the genus Prototheca, the altered fatty acid profile having at least 10% C10:

0 and 40% C12;

0 fatty acids, the cleaner having a reduced odor compared to a cleaner where all the fatty acids are derived from vegetable or animal triglyceride oil having a fatty acid profile of at least 40% C12;

0 fatty acids, the method comprising the steps of;

a) providing the C1-C4 esters of fatty acids derived from the triglyceride oil;

b) admixing at least one additional ingredient with the C1-C4 ester of fatty acids derived from the triglyceride oil to prepare the cleaner.

16. The method of claim 15, wherein the odor is an unpleasant odor characteristic of a C6 or C8 fatty acid or ester thereof.

17. The method of claim 15, wherein the ester is a methyl, ethyl, propyl, iso-propyl, butyl, or a tert-butyl ester.

18. The method of claim 15, wherein at least 50% of the fatty acids are C12:

0 fatty acids or the combined total amount of C;

10 and C;

12 fatty acids is at least 60%.

19. The method of claim 15, wherein at least 15% of the fatty acids are C10:

0 fatty acids.

20. The method of claim 15, comprising a terpene.

21. The method of claim 15, wherein the terpene is limonene.

23. The method of claim 15, wherein the recombinant oleaginous cell is a Prototheca moriformis cell.