Low polyunsaturated fatty acid oils and uses thereof

• US 9,249,252 B2
• Filed: 04/25/2014
• Issued: 02/02/2016
• Est. Priority Date: 04/26/2013
• Status: Active Grant

• Current Assignee: Corbion Biotech, Inc. (Corbion NV)
• Original Assignee: Solazyme Inc.
• Inventors: Ngantung, Frederyk, Braksmayer, Diza, Bond, Risha, Cafmeyer, Jeffrey T.
• Primary Examiner(s): Boyle, Robert C
• Assistant Examiner(s): RIETH, STEPHEN EDWARD
• Application Number:
  US14/262,070
• Publication Number:
  US 20140357746A1
• Time in Patent Office: 648 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: A23D 9/00 Other edible oils or fats, e.g. shortenings, cooking oils
• CPC Class Codes: A23K 20/158 Fatty acids; Fats; Products containing oils or fats
• CPC Class Codes: A23L 33/115 Fatty acids or derivatives thereof; Fats or oils
• CPC Class Codes: A23V 2002/00 Food compositions, function of food ingredients or processes for food or foodstuffs
• CPC Class Codes: C08G 18/14 Manufacture of cellular products
• CPC Class Codes: C08G 18/3203 Polyhydroxy compounds
• CPC Class Codes: C08G 18/36 Hydroxylated esters of higher fatty acids
• CPC Class Codes: C08G 18/7657 containing two or more aromatic rings
• CPC Class Codes: C08G 2110/0008 flexible
• CPC Class Codes: C10G 2300/1014 of vegetal origin
• CPC Class Codes: C10L 1/026 for compression ignition
• 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 3/003 by esterification of fatty acids with alcohols C11C3/02 takes precedence
• CPC Class Codes: C11D 1/66 Non-ionic compounds C11D1/002, C11D1/004, C11D1/008 take precedence
• CPC Class Codes: C11D 17/0017 Multi-phase liquid compositions
• CPC Class Codes: C11D 3/188 Terpenes
• CPC Class Codes: C11D 3/2024 cyclic; polycyclic
• CPC Class Codes: C11D 3/2079 Monocarboxylic acids-salts thereof
• CPC Class Codes: C12P 7/6463 obtained from glyceride producing microorganisms, e.g. single cell oil
• CPC Class Codes: C12P 7/6472 containing polyunsaturated fatty acid [PUFA] residues, i.e. having two or more double bonds in their backbone
• CPC Class Codes: Y02E 50/10 : Biofuels, e.g. bio-diesel
• CPC Class Codes: Y02T 50/678 : Aviation using fuels of non-fossil origin

Abstract

Provided are microalgal oils having a low polyunsaturated fatty acid profile and derivatives of the oils, including acids, esters, epoxides, hydroxylated acids and esters, urethanes, amides, and polymers thereof. Also provided are compositions comprising the oils and their derivatives and their uses in foodstuffs and in industrial and material applications. The compositions include flexible polyurethane foams prepared from the microalgal oils.

Claims

1. A method for preparing a polyurethane foam, the method comprising:

a) providing a microalgal oil comprising triacylglycerides having a fatty acid profile of at least 80% 18;

1 fatty acids and less than 4% 18;

2 fatty acids, the triglycerides further having an iodine value of 75 or less and/or is non-hydrogenated;

b) subjecting the triacylglycerides to an epoxidation reaction to form epoxides;

c) subjecting the epoxides to a ring opening reaction to form microalgal derived polyols, wherein the microalgal derived polyols are liquids at room temperature;

d) blending the microalgal derived polyols with petroleum derived polyols to form blended polyols; and

e) subjecting the blended polyols to an isocyanate condensation reaction to form the polyurethane foam.

2. The method of claim 1 wherein the polyurethane foam has less than 25% loss in thickness after being compressed to 75% thickness at 70°

C. and 5% relative humidity for 22 hours in accordance with American Society for Testing and Materials standard ASTM D-3574.

3. The method of claim 1, wherein the polyurethane foam maintains a yellowness index of 31 or less after being exposed to ambient light for 18 weeks in accordance with American Society for Testing and Materials standard ASTM D-E313.

4. The method of claim 1, wherein the triacylglycerides have an iodine value of 70-75.

5. The method of claim 4 wherein the triacylglycerides have an iodine value of 74 to 75.

6. The method of claim 1, wherein the triacylglycerides have a fatty acid profile of less than 1% trans fatty acids or wherein the triacylglyceride is non-hydrogenated.

7. The method of claim 6, wherein the triacylglycerides have a fatty acid profile of less than 0.1% trans fatty acids.

8. The method of claim 1, wherein the triacylglycerides have a fatty acid profile of less than 3% 18:

2 fatty acids.

9. The method of claim 8, wherein the triacylglycerides have a fatty acid profile of less than 2% 18:

2 fatty acids.

10. The method of claim 8, wherein the triacylglycerides have a fatty acid profile of less than 1% 18:

2 fatty acids.

11. The method of claim 8, wherein the triacylglycerides have a fatty acid profile of less than 0.1% 18:

2 fatty acids.

12. The method of claim 8, wherein the triacylglycerides have a fatty acid profile of less than 0.01% 18:

2 fatty acids.

13. The method of claim 1, wherein the triacylglycerides have a fatty acid profile of at least 85% 18:

1 fatty acids and 0.1% or less 18;

2 fatty acids.

14. The method of claim 1, wherein the microalgal oil further comprises C29 and C28 sterols, wherein the amount of C28 sterols is greater than C29 sterols.

15. The method of claim 1, wherein the microalgae is Parachlorella, Prototheca, or Chlorella.

16. The method of claim 15, wherein the microalgae is Prototheca or Prototheca moriformis.

17. The method of claim 1, wherein the blended polyols comprise at least 20% by weight of the microalgal derived polyols.

18. The method of claim 1, wherein the polyols are mixed with a catalyst prior to the isocyanate condensation reaction.

19. The method of claim 18 wherein the catalyst is an amine catalyst.

20. The method of claim 19 wherein the amine catalyst is a diethanolamine catalyst.

21. The method of claim 20, wherein the mole ratio of the amine catalyst to the microalgal derived polyol is greater than 3:

1.