Grease compositions comprising estolide base oils

• US 9,605,231 B2
• Filed: 06/06/2016
• Issued: 03/28/2017
• Est. Priority Date: 06/17/2011
• Status: Active Grant

• Current Assignee: Biosynthesic Technologies LLC
• Original Assignee: Biosynthesic Technologies LLC
• Inventors: Forest, Jeremy, Bredsguard, Jakob
• Primary Examiner(s): MC GINTY, DOUGLAS J
• Application Number:
  US15/174,666
• Publication Number:
  US 20160281023A1
• Time in Patent Office: 295 Days
• Field of Search: 508/465, 508/459, 508/463, 524/311, 524/306, 549/90
• US Class Current: 1/1
• CPC Class Codes: C08K 5/10 Esters; Ether-esters
• CPC Class Codes: C10M 105/36 of polycarboxylic acids
• CPC Class Codes: C10M 117/04 containing hydroxy groups
• CPC Class Codes: C10M 129/10 having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C10M 133/46 Imidazoles
• CPC Class Codes: C10M 135/06 Esters, e.g. fats
• CPC Class Codes: C10M 137/10 Thio derivatives
• CPC Class Codes: C10M 169/02 Mixtures of base-materials and thickeners
• CPC Class Codes: C10M 169/06 Mixtures of thickeners and additives
• CPC Class Codes: C10M 2203/1025 used as base material
• CPC Class Codes: C10M 2207/023 having hydroxy groups bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C10M 2207/026 with tertiary alkyl groups
• CPC Class Codes: C10M 2207/1256 used as thickening agent
• CPC Class Codes: C10M 2207/1265 used as thickening agent
• CPC Class Codes: C10M 2207/1285 used as thickening agents
• CPC Class Codes: C10M 2207/2825 used as base material
• CPC Class Codes: C10M 2207/301 used as base material
• CPC Class Codes: C10M 2207/402 Castor oils
• CPC Class Codes: C10M 2215/064 Di- and triaryl amines
• CPC Class Codes: C10M 2215/224 Imidazoles
• CPC Class Codes: C10M 2219/024 : of esters, e.g. fats
• CPC Class Codes: C10M 2219/068 : Thiocarbamate metal salts
• CPC Class Codes: C10M 2223/043 : Ammonium or amine salts thereof
• CPC Class Codes: C10M 2223/045 : Metal containing thio derivatives
• CPC Class Codes: C10N 2010/02 : Groups 1 or 11
• CPC Class Codes: C10N 2010/04 : Groups 2 or 12
• CPC Class Codes: C10N 2010/10 : Groups 5 or 15
• CPC Class Codes: C10N 2020/02 : Viscosity; Viscosity index
• CPC Class Codes: C10N 2020/065 : Saturated Compounds
• CPC Class Codes: C10N 2020/081 : Biodegradable compounds
• CPC Class Codes: C10N 2030/02 : Pour-point; Viscosity index
• CPC Class Codes: C10N 2030/06 : Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
• CPC Class Codes: C10N 2030/10 : Inhibition of oxidation, e.g. anti-oxidants
• CPC Class Codes: C10N 2030/12 : Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
• CPC Class Codes: C10N 2030/14 : Metal deactivation
• CPC Class Codes: C10N 2030/20 : Colour, e.g. dyes
• CPC Class Codes: C10N 2030/64 : Environmental friendly compositions
• CPC Class Codes: C10N 2050/10 : Semi-solids; greasy
• CPC Class Codes: C10N 2060/04 : Oxidation, e.g. ozonisation

Abstract

Provided herein are grease compositions comprising at least one estolide compound of formula:

in which n is an integer equal to or greater than 0; m is an integer equal to or greater than 2; R₁, independently for each occurrence, is selected from optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; R₂ is selected from hydrogen and optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; and R₃ and R₄, independently for each occurrence, are selected from optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched. Also provided are methods of making estolide-based grease products.

Claims

1. A grease composition comprising

an estolide base oil;

a polyisobutylene; and

at least one thickener,

wherein said estolide base oil comprises at least one estolide compound selected from compounds of Formula I;

2. The grease composition according to claim 1, wherein

x is, independently for each occurrence, an integer selected from 0 to 14;

y is, independently for each occurrence, an integer selected from 0 to 14;

n is an integer selected from 0 to 8;

R₁ is an optionally substituted C₁ to C₂₂ alkyl that is saturated or unsaturated, and branched or unbranched; and

R₂ is an optionally substituted C₁ to C₂₂ alkyl that is saturated or unsaturated, and branched or unbranched,

wherein each fatty acid chain residue is unsubstituted.

3. The grease composition according to claim 2, wherein

x+y is, independently for each fatty acid chain residue, an integer selected from 13 to 15;

and

n is an integer selected from 0 to 6.

4. The grease composition according to claim 2, wherein R₂ is a branched or unbranched C₁ to C₂₀ alkyl that is saturated or unsaturated.

5. The grease composition according to claim 4, wherein R₂ is branched and saturated.

6. The grease composition according to claim 5, wherein R₂ is selected from C₆ to C₁₂ alkyl.

7. The grease composition according to claim 6, wherein R₂ is 2-ethylhexyl.

8. The grease composition according to claim 2, wherein R₁ is a branched or unbranched C₁ to C₂₀ alkyl that is saturated or unsaturated.

9. The grease composition according to claim 8, wherein R₁ is unbranched and saturated.

10. The grease composition according to claim 9, wherein R₁ is selected from unsubstituted C₇ to C₁₇ alkyl that is unbranched and saturated.

11. The grease composition according to claim 1, wherein said estolide base oil has an EN selected from an integer or fraction of an integer that is equal to or greater than 3.

12. The grease composition according to claim 1, wherein the at least one thickener is one or more of a simple lithium soap, a complex lithium soap, a simple calcium soap, or a complex calcium soap.

13. The grease composition according to claim 1, wherein said composition further comprises at least one additive.

14. The grease composition according to claim 13, wherein the at least one additive is one or more of a preservative, an antioxidant, a colorant, an anti-weld agent, an extreme pressure agent, a flame retardant, a rust inhibitor, a corrosion inhibitor, an oil bleed inhibitor, a metal deactivator, a viscosity modifier, a tackifier, or a pour point depressant.

15. The grease composition according to claim 13, wherein the at least one additive is one or more of a sulfurized fat, a sulfurized glyceridic oil, a sulfurized vegetable oil, a sulfurized fatty acid, or a sulfurized fatty acid ester.

16. The grease composition according to claim 13, wherein the at least one additive is an anti-wear agent.

17. The grease composition according to claim 16, wherein the anti-wear agent is selected from one or more of ZDDP, an ADDC, or an amine neutralized alkyl phosphate.

18. The grease composition according to claim 13, wherein the at least one additive is an antioxidant.

19. The grease composition according to claim 18, wherein the antioxidant is one or more of an ADPA, ZDDC, or BHT.

20. The grease composition according to claim 1, wherein the estolide base oil comprises about 30% to about 95% by weight of the grease composition.

21. The grease composition according to claim 20, wherein said composition comprisesto 30% by weight of the at least one thickener;

0% to 15% by weight of at least one anti-wear agent; and

0% to 5% by weight of at least one antioxidant.

22. The grease composition according to claim 1, further comprising at least one trimellitate.

23. A method comprising contacting a marine vessel with the grease composition according to claim 1.