Grease compositions comprising estolide base oils

• US 10,150,931 B2
• Filed: 03/03/2017
• Issued: 12/11/2018
• Est. Priority Date: 06/17/2011
• Status: Active Grant

• Current Assignee: Biosynthesic Technologies LLC
• Original Assignee: Biosynthesic Technologies LLC
• Inventors: Bredsguard, Jakob, Forest, Jeremy
• Primary Examiner(s): McGinty, Douglas J
• Application Number:
  US15/449,768
• Publication Number:
  US 20170233676A1
• Time in Patent Office: 648 Days
• Field of Search: 508465, 508459, 508463, 524311, 524306, 549 90
• 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 composition comprising:

at least 25% by weight of an estolide base oil; and

at least one thickener selected from a metal soap, a polyurea, a fluorocarbon resin, or a silica.

2. The composition according to claim 1, wherein the estolide base oil comprises one or more compounds of Formula I:

3. The composition according to claim 2, 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 20;

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

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

wherein each fatty acid chain residue is unsubstituted.

4. The composition according to claim 3, wherein R₁ is unsubstituted and unbranched.

5. The composition according to claim 4, wherein R₁ is saturated.

6. The composition according to claim 3, wherein R₂ is saturated.

7. The composition according to claim 3, wherein x is, independently for each occurrence, an integer selected from 7 and 8.

8. The composition according to claim 7, wherein y is, independently for each occurrence, an integer selected from 7 and 8.

9. The composition according to claim 3, wherein x is 10 for each occurrence.

10. The composition according to claim 9, wherein y is 5 for each occurrence.

11. The composition according to claim 3, 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, wherein EN is the average number of estolide linkages in compounds according to Formula I.

12. The composition according to claim 3, wherein the at least one thickener comprises one or more of a simple lithium soap or a complex lithium soap.

13. The composition according to claim 12, wherein the at least one thickener comprises one or more of lithium stearate, lithium 12-hydroxy stearate, lithium 16-hydroxystearate, or lithium ricinoleate.

14. The composition according to claim 3, wherein the at least one thickener comprises a metal soap that is a reaction product of at least one metal-based material and at least one carboxylic acid or carboxylic acid ester.

15. The composition according to claim 14, wherein the at least one metal-based material comprises one or more of a metal hydroxide, a metal carbonate, a metal bicarbonate, or a metal oxide.

16. The composition according to claim 14, wherein the metal of the at least one metal-based material comprises one or more of an alkali metal or alkaline earth metal.

17. The composition according to claim 3, wherein said composition further comprises at least one additive.

18. The composition according to claim 17, wherein the at least one additive comprises 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.

19. The composition according to claim 3, wherein the estolide base oil comprises 30% to 95% by weight of the composition.

20. The composition according to claim 3, wherein the estolide base oil comprises 50% to 95% by weight of the composition.

21. The composition according to claim 3, wherein the at least one thickener comprises one or more of a simple metal soap or a complex metal soap.

22. The composition according to claim 3, further comprising at least one trimellitate.

23. The composition according to claim 3, wherein the at least one thickener comprises a polyurea.

24. The composition of claim 23, wherein the at least one thickener comprises a polyurea complex.

25. The composition of claim 3, wherein the at least one thickener comprises a silica.

26. The composition of claim 25, wherein the at least one thickener comprises a fumed silica.