Thermocleavable friction modifiers and methods thereof

Patent metadata

Field	Value
Publication number	US-10640725-B2
Application number	US-201715670891-A
Country	US
Kind code	B2
Filing date	Aug 7, 2017
Priority date	Aug 5, 2016
Publication date	May 5, 2020
Grant date	May 5, 2020

Abstract

Certain embodiments of the invention provide a lubricating oil composition comprising a lubricating oil base stock and a compound of formula (I):

or a salt thereof, wherein R 1 , R 2 , R 3 and R 4 have any of the values defined in the specification, as well as methods of use thereof.

First claim

What is claimed is:

1. A lubricating oil composition comprising a lubricating oil base stock and a compound of formula (I):

wherein, R 1 and R 2 are each independently tertiary (C 4 -C 12 )alkyl, benzyl or phenethyl; R 3 is OR a , wherein R a is (C 1 -C 20 )alkyl, (C 1 -C 20 )alkanoyl, (C 2 -C 20 )alkenyl or (C 3 -C 20 )alkenoyl; and R 4 is (C 1 -C 20 )alkyl, (C 1 -C 20 )alkanoyl, (C 2 -C 20 )alkenyl or (C 3 -C 20 )alkenoyl; or a salt thereof.

2. A lubricating oil composition comprising a lubricating oil base stock and a compound of formula (I):

wherein, R 1 and R 2 are each H or wherein R 1 and R 2 are each tert-butyl; R 3 is H or OR a , wherein R a is (C 1 -C 20 )alkyl, (C 1 -C 20 )alkanoyl, (C 2 -C 20 )alkenyl or (C 3 -C 20 )alkenoyl; and R 4 is (C 1 -C 20 )alkyl, (C 1 -C 20 )alkanoyl, (C 2 -C 20 )alkenyl or (C 3 -C 20 )alkenoyl;

or a salt thereof.

3. The lubricating oil composition of claim 1 , wherein R 3 is OR a , wherein R a is (C 1 -C 20 )alkyl.

4. The lubricating oil composition of claim 1 , wherein R 3 is OR a , wherein R a is (C 1 -C 20 )alkanoyl.

5. A lubricating oil composition comprising a lubricating oil base stock and a compound of formula (I):

wherein, R 1 and R 2 are each independently H, (C 1 -C 12 )alkyl, benzyl or phenethyl; R 3 is H or OR a , wherein R a is (C 1 -C 20 )alkyl, (C 1 -C 20 )alkanoyl, (C 2 -C 20 )alkenyl or (C 3 -C 20 )alkenoyl; R 4 is (C 1 -C 20 )alkyl; or a salt thereof.

6. The lubricating oil composition of claim 1 , wherein R 4 is (C 1 -C 20 )alkanoyl.

7. A lubricating oil composition comprising, a lubricating oil base stock and a compound of formula (I) selected from the group consisting of:

or a salt thereof.

8. The lubricating oil composition of claim 2 , wherein the compound of formula (I) is:

or a salt thereof.

9. The lubricating oil composition of claim 2 , wherein the compound of formula (I) is:

10. The lubricating oil composition of claim 1 , wherein the lubricating oil base stock comprises a Group I, Group II, Group III, Group IV or Group V base oil.

11. The lubricating oil composition of claim 1 , comprising a mixture of two or more compounds of formula (I), or salts thereof, wherein the two or more compounds of formula (I), or salts thereof, have different thermal release temperatures.

12. The lubricating oil composition of claim 1 , further comprising one or more lubricating oil performance additives selected from the group consisting of an anti-wear additive, viscosity modifier, antioxidant, detergent, dispersant, pour point depressant, corrosion inhibitor, metal deactivator, seal compatibility additive, anti-foam agent, other friction modifier and anti-rust additive/inhibitor.

13. A compound of formula (I):

wherein, R 1 and R 2 are each independently tertiary (C 4 -C 12 ) alkyl; R 3 is OR a , wherein R a is (C 3 -C 20 )alkanoyl or (C 3 -C 20 )alkenoyl; and R 4 is (C 1 -C 20 )alkanoyl or (C 3 -C 20 )alkenoyl; or a salt thereof.

14. The compound of claim 13 , which is a compound of formula (Ib):

wherein, R 1 and R 2 are each independently tertiary (C 4 -C 12 ) alkyl; R 3 is OR a , wherein R a is (C 3 -C 8 )alkanoyl or (C 3 -C 8 )alkenoyl; and R 4 is (C 1 -C 20 )alkanoyl, or (C 3 -C 20 )alkenoyl; or a salt thereof.

15. A compound of formula (Ic):

wherein, R 1 and R 2 are each independently tertiary (C 4 -C 12 ) alkyl, R 3 is OR a , wherein R a is (C 1 -C 20 )alkanoyl or (C 3 -C 20 )alkenoyl; and R 4 is (C 14 -C 20 )alkanoyl or (C 14 -C 20 )alkenoyl; or a salt thereof.

16. The compound of claim 13 , which is

or a salt thereof.

17. A lubricating oil composition prepared by combining a lubricating oil base stock and a compound of formula (I):

wherein, R 1 and R 2 are each independently H, tertiary (C 4 -C 12 )alkyl, benzyl or phenethyl; R 3 is OR a , wherein R a is C 1 -C 20 )alkanoyl, or (C 3 -C 20 )alkenoyl; and R 4 is (C 1 -C 20 )alkanoyl or (C 3 -C 20 )alkenoyl;

or a salt thereof.

18. A method of reducing friction in an engine or other mechanical component lubricated with a lubricating oil, comprising providing a lubricating oil composition of claim 1 to the engine or other mechanical component.

19. A method of providing friction reducing properties in a lubricant system, comprising adding a lubricating oil composition of claim 1 to the lubricant system.

20. A method of reducing friction in an engine or other mechanical component lubricated with a lubricating oil, comprising providing a lubricating oil composition of claim 2 to the engine or other mechanical component.

21. A method of providing friction reducing properties in a lubricant system, comprising adding a lubricating oil composition of claim 2 to the lubricant system.

22. The lubricating oil composition of claim 2 , wherein, R 1 and R 2 are each H; R 3 is H or OR a , wherein R a is (C 1 -C 20 )alkanoyl or (C 3 - C 20 )alkenoyl; and R 4 is (C 1 -C 20 )alkanoyl or (C 3 -C 20 )alkenoyl; or a salt thereof.

23. The lubricating oil composition of claim 22 , wherein, R 1 and R 2 are each H; R 3 is OR a , wherein R a is (C 10 -C 20 )alkanoyl or (C 10 -C 20 )alkenoyl; and R 4 is (C 10 -C 20 )alkanoyl or (C 10 -C 20 )alkenoyl; or a salt thereof.

24. The lubricating oil composition of claim 2 , wherein, R 1 and R 2 are each tert-butyl; R 3 is H or OR a , wherein R a is (C 1 -C 20 )alkanoyl or (C 3 -C 20 )alkenoyl; and R 4 is (C 1 -C 20 )alkanoyl or (C 3 -C 20 )alkenoyl; or a salt thereof.

25. The lubricating oil composition of claim 24 , wherein, R 1 and R 2 are each tert-butyl; R 3 is OR a , wherein R a is (C 10 -C 20 )alkanoyl or (C 10 -C 20 )alkenoyl; and R 4 is (C 10 -C 20 )alkanoyl or (C 10 -C 20 )alkenoyl; or a salt thereof.

26. The lubricating oil composition of claim 1 , wherein, R 1 and R 2 are each independently tertiary alkyl selected from the group consisting of butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl; R 3 is OR a , wherein R a is (C 1 -C 20 )alkanoyl or (C 3 -C 20 )alkenoyl; and R 4 is (C 1 -C 20 )alkanoyl or (C 3 -C 20 )alkenoyl; or a salt thereof.

27. The lubricating oil compositi

Assignees

• Univ Rutgers
• Exxonmobil Res & Eng Co

Inventors

• Uhrich Kathryn
• Faig Jonathan
• Zhang Yingyue
• Luo Shuji
• Ng Man Kit
• Schilowitz Alan
• Shough Anne Marie

Classifications

• C10N2030/06

  Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure · CPC title

• C07C69/02

  Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen · CPC title

• C10N2030/54

  Fuel economy · CPC title

• C10M2207/124

  containing hydroxy groups; Ethers thereof · CPC title

• C10M129/42 Primary

  polycarboxylic · CPC title