Phenolic dimers, the process of preparing same and the use thereof

• US 7,732,390 B2
• Filed: 11/24/2004
• Issued: 06/08/2010
• Est. Priority Date: 11/24/2004
• Status: Active Grant

• Current Assignee: Afton Chemical Corporation
• Original Assignee: Afton Chemical Corporation
• Inventors: Passut, Charles A., Bradley, Joe S., Shiau, Ju-Fu, Devlin, Cathy C., Kadkhodayan, Abbas
• Primary Examiner(s): Caldarola; Glenn A
• Assistant Examiner(s): Oladapo; Taiwo
• Application Number:
  US10/995,097
• Publication Number:
  US 20060111257A1
• Time in Patent Office: 2,022 Days
• Field of Search: 508/287
• US Class Current: 508/542
• CPC Class Codes: C07C 37/20 using aldehydes or ketones
• CPC Class Codes: C07C 37/66 by conversion of hydroxy groups to O-metal groups
• CPC Class Codes: C07C 39/16 Bis-(hydroxyphenyl) alkanes; Tris-(hydroxyphenyl)alkanes
• CPC Class Codes: C07C 39/21 with at least one hydroxy group on a non-condensed ring
• CPC Class Codes: C07C 39/235 Metal derivatives of a hydroxy group bound to a six-membered aromatic ring
• CPC Class Codes: C10M 159/22 containing phenol radicals
• CPC Class Codes: C10M 169/048 the additives being a mixture of compounds of unknown or incompletely defined constitution, non-macromolecular and macromolecular compounds
• CPC Class Codes: C10M 2207/023 having hydroxy groups bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C10M 2207/027 Neutral salts thereof
• CPC Class Codes: C10M 2207/028 Overbased salts thereof
• CPC Class Codes: C10M 2207/289 containing free hydroxy groups
• CPC Class Codes: C10M 2215/064 Di- and triaryl amines
• CPC Class Codes: C10M 2215/28 Amides; Imides
• CPC Class Codes: C10M 2219/044 Sulfonic acids, Derivatives thereof, e.g. neutral salts
• CPC Class Codes: C10M 2219/046 Overbasedsulfonic acid salts
• CPC Class Codes: C10M 2223/045 Metal containing thio derivatives
• CPC Class Codes: C10N 2030/04 Detergent property or dispersant property
• CPC Class Codes: C10N 2040/04 Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
• CPC Class Codes: C10N 2040/25 Internal-combustion engines
• CPC Class Codes: C10N 2060/02 Reduction, e.g. hydrogenation
• CPC Class Codes: C10N 2060/06 : by epoxydes or oxyalkylation reactions
• CPC Class Codes: C10N 2060/14 : by boron or a compound containing boron

Abstract

This invention relates to detergents, lubricating oil additives and compositions, and methods of preparing detergents, lubricating oil additives and compositions. More specifically, this invention relates to novel phenolic dimers.

Claims

1. A compound comprising Formula I:

2. The compound of claim 1, wherein each R² and R⁴ is polyisobutyl containing 10 to 100 carbon atoms.

3. The compound of claim 1, wherein each R² and R⁴ is polyisobutyl containing 55 to 75 carbon atoms.

4. The compound of claim 1, wherein n is 1.

5. The compound of claim 1, wherein R¹ and R³ are each methyl;

R² and R⁴ are each polyisobutyl; and

n is 1.

6. The compound of claim 5, wherein each R¹ and R³ is methyl;

R² and R⁴ are each polyisobutyl containing 10 to 100 carbon atoms; and

n is 1.

18. A process for preparing a compound of claim 7, said process comprising:

(a) contacting an alkaline earth metal source, a saturated or unsaturated carboxylic acid, a C₁-C₂₀ monohydric alcohol, and a C₂-C₄ polyhydric alcohol with a compound of Formula I

19. The process of claim 18, wherein the alkaline earth metal source is calcium hydroxide.

20. The process of claim 18, wherein the saturated or unsaturated carboxylic acid comprises oleic acid.

21. The process of claim 18, wherein the C₁-C₂₀ monohydric alcohol comprises 2-ethylhexanol.

22. The process of claim 18, wherein the C₂-C₄ polyhydric alcohol comprises ethylene glycol.

27. A lubricating oil composition prepared by a process comprising:

(a) combining the compound of claim 1, a base oil, an alkaline earth metal source, a saturated or unsaturated carboxylic acid, a C₁-C₂₀ monohydric alcohol, and a C₂-C₄ polyhydric alcohol; and

(b) adding carbon dioxide.

28. The lubricating oil composition prepared by the process of claim 27, wherein the alkaline earth metal source comprises calcium hydroxide.

29. The lubricating oil composition prepared by the process of claim 27, wherein the saturated or unsaturated carboxylic acid comprises oleic acid.

30. The lubricating oil composition prepared by the process of claim 27, wherein the C₁-C₂₀ monohydric alcohol comprises 2-ethylhexanol.

31. The lubricating oil composition prepared by the process of claim 27, wherein the C₂-C₄ polyhydric alcohol comprises ethylene glycol.

7. A compound, or a salt form thereof, comprising Formula III:

8. The compound of claim 7, wherein each R⁸ and R¹⁰ is polyisobutyl.

9. The compound of claim 8, wherein each R⁸ and R¹⁰ is polyisobutyl containing 10 to 100 carbon atoms.

10. The compound of claim 8, wherein each R⁸ and R¹⁰ is polyisobutyl containing 55 to 75 carbon atoms.

11. The compound of claim 7, wherein each R⁸ and R¹⁰ is dodecyl.

12. The compound of claim 7, wherein M is selected from a group consisting of calcium, magnesium, and barium.

13. The compound of claim 12, wherein M comprises calcium.

14. The compound of claim 7, wherein n is 1.

15. The compound of claim 7, wherein each R⁷ and R⁹ is methyl;

each R⁸ and R¹⁰ is polyisobutyl;

M is calcium; and

n is 1.

16. The compound of claim 15, wherein each R⁷ and R⁹ is methyl;

each R⁸ and R¹⁰ is polyisobutyl containing 10 to 100 carbon atoms;

M is calcium; and

n is 1.

17. The compound of claim 7, wherein the compound comprises the calcium carbonate salt form.

23. A lubricating oil composition comprising the overbased compound of claim 7.

24. A lubricating oil composition of claim 23, wherein said lubricating composition comprises one or more additional additives selected from the group consisting of a polymeric viscosity modifier, a detergent, an antioxidant, a dispersant, a rust inhibitor, an antiwear agent, a boron-containing compound, a friction modifier, a pour-point depressant, and an antifoaming agent.

25. The lubricating oil composition of claim 24, wherein said lubricating oil composition comprises up to about 12% polymeric viscosity modifier, up to about 10% detergent, up to about 10% antioxidant, up to about 12% dispersant, up to about 5% rust inhibitor, up to about 5% antiwear agent, up to about 8% boron-containing compound, up to about 5% friction modifier, up to about 1% pour point depressant, and up to about 1% antifoaming agent, wherein the percentage of each component represents the weight percent of each component based upon the weight of the final lubricating oil composition.

26. The lubricating oil composition of claim 25, wherein said lubricating oil composition comprises about 4 to about 10% polymeric viscosity modifier, about 0.1 to about 2.5% detergent, about 0.2 to about 4% antioxidant, about 4 to about 10% dispersant, about 0.25 to about 5% antiwear agent, about 1 to about 7% boron-containing compound, about 0.1 to about 1% friction modifier, about 0.1 to about 0.5% pour point depressant, and about 0.001 to about 0.015% antifoaming agent, wherein the percentage of each component represents the weight percent of each component based upon the weight of the final lubricating oil composition.

32. A method for lubricating an internal combustion engine comprising adding the lubricating oil composition of claim 23 to said engine.

33. A method for lubricating transmissions comprising adding the lubricating oil composition of claim 23 to said transmission.

34. A method for lubricating a transmission according to claim 33 wherein said transmission is selected from a group consisting of a manual transmission, an automatic transmission, and a continuously variable transmission.

35. A lubricating oil concentrate comprising the overbased compound of claim 7.

36. A lubricating oil concentrate comprising the overbased compound of claim 7 in a substantially inert liquid organic diluent.

37. A lubricating oil concentrate of claim 35, wherein said lubricating concentrate comprises one or more additional additives selected from the group consisting of a polymeric viscosity modifier, a detergent, an antioxidant, a dispersant, a rust inhibitor, an antiwear agent, a boron-containing compound, a friction modifier, a pour-point depressant, and an antifoaming agent.