Oil-soluble molybdenum derivatives derived from hydroxyethyl-substituted Mannich bases

• US 7,960,321 B2
• Filed: 05/15/2008
• Issued: 06/14/2011
• Est. Priority Date: 10/20/2004
• Status: Active Grant

• Current Assignee: Afton Chemical Corporation
• Original Assignee: Afton Chemical Corporation
• Inventors: Liesen, Gregory P., Loper, John T., Gatto, Vincent J.
• Primary Examiner(s): Caldarola; Glenn A
• Assistant Examiner(s): VASISTH, VISHAL V
• Application Number:
  US12/121,462
• Publication Number:
  US 20090075849A1
• Time in Patent Office: 1,125 Days
• Field of Search: 508/362, 508/108, 508/542, 508/572, 556/57
• US Class Current: 508/362
• CPC Class Codes: C07F 11/005 compounds without a metal-carbon linkage
• CPC Class Codes: C10M 159/16 obtained by Mannich reactions
• CPC Class Codes: C10M 159/18 Complexes with metals
• CPC Class Codes: C10M 163/00 Lubricating compositions characterised by the additive being a mixture of a compound of unknown or incompletely defined constitution and a non-macromolecular compound, each of these compounds being essential
• CPC Class Codes: C10M 177/00 Special methods of preparation of lubricating compositions; Chemical modification by after-treatment of components or of the whole of a lubricating composition, not covered by other classes
• CPC Class Codes: C10M 2207/023 having hydroxy groups bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C10M 2207/08 Aldehydes; Ketones
• CPC Class Codes: C10M 2215/042 containing hydroxy groups; Alkoxylated derivatives thereof
• CPC Class Codes: C10M 2215/064 Di- and triaryl amines
• CPC Class Codes: C10M 2219/089 Overbased salts
• CPC Class Codes: C10M 2223/045 Metal containing thio derivatives
• CPC Class Codes: C10N 2010/12 Groups 6 or 16
• CPC Class Codes: C10N 2030/06 Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
• CPC Class Codes: C10N 2030/54 Fuel economy
• CPC Class Codes: C10N 2040/25 Internal-combustion engines
• CPC Class Codes: C10N 2070/00 Specific manufacturing methods for lubricant compositions

Abstract

The present disclosure relates to organic molybdenum complexes prepared by reacting a Mannich base with a source of molybdenum. The complexes may be useful in lubricating oil compositions as at least one of an antioxidant, a deposit control additive, and a friction modifier. The organic molybdenum complexes may show a reduced tendency to color finished oils.

Claims

1. A lubricating oil composition comprising a major amount of an oil of lubricating viscosity and an organic molybdenum complex prepared by a process comprising:

(a) reacting an alkylphenol substituted with an alkyl group in the para-position with a formaldehyde source and an N-hydroxyethyl substituted diamine to yield a Mannich base; and

(b) reacting the Mannich base with molybdenum trioxide to form the organic molybdenum complex,

wherein the N-hydroxyethyl substituted diamine is selected from the group consisting of 2-(2-aminoethylamino)ethanol, aminopropyldiethanolamine, and aminoethyldiethanolamine.

2. The lubricating oil composition according to claim 1, wherein the organic molybdenum complex is oil-soluble.

19. A process for lubricating a crankcase, comprising adding a lubricating oil composition according to claim 1 to a crankcase.

20. A crankcase lubricated with a composition according to lubricating oil composition according to claim 1.

23. A process for improving the fuel economy of an internal combustion engine comprising using as a crankcase lubricating oil for the internal combustion engine the lubricating oil composition of claim 1, wherein the organic molybdenum complex is present in an amount sufficient to improve the fuel economy of the internal combustion engine using the crankcase lubricating oil composition, as compared to the engine operated in the same manner and using the same crankcase lubricating oil except that the oil is devoid of the organic molybdenum complex.

24. The process according to claim 23, wherein the organic molybdenum complex is present in the crankcase lubricating oil in an amount sufficient to provide at least 50 ppm of molybdenum to the finished lubricating oil.

25. A process for reducing deposits in an internal combustion engine comprising using as a crankcase lubricating oil for the internal combustion engine the lubricating oil composition of claim 1, wherein the organic molybdenum complex is present in an amount sufficient to reduce the weight of deposits in an internal combustion engine operated using the crankcase lubricating oil, as compared to the weight of deposits in the engine operated in the same manner and using the same crankcase lubricating oil except that the oil is devoid of the organic molybdenum complex.

26. The process according to claim 25, wherein the organic molybdenum complex is present in the crankcase lubricating oil in an amount sufficient to provide at least 50 ppm of molybdenum to the finished lubricating oil.

27. A process for reducing wear in an internal combustion engine comprising using as a crankcase lubricating oil for the internal combustion engine the lubricating oil composition of claim 1, wherein the organic molybdenum complex is present in an amount sufficient to reduce the wear in an internal combustion engine operated using the crankcase lubricating oil, as compared to the wear in the engine operated in the same manner and using the same crankcase lubricating oil except that the oil is devoid of the organic molybdenum complex.

28. The process according to claim 27, wherein the organic molybdenum complex is present in the crankcase lubricating oil in an amount sufficient to provide at least 50 ppm of molybdenum to the finished lubricating oil.

29. A process for providing friction modification in an internal combustion engine comprising using as a crankcase lubricating oil for the internal combustion engine the lubricating oil composition of claim 1, wherein the organic molybdenum complex is present in an amount sufficient to reduce the wear in an internal combustion engine operated using the crankcase lubricating oil, as compared to the wear in the engine operated in the same manner and using the same crankcase lubricating oil except that the oil is devoid of the organic molybdenum complex.

30. The process according to claim 29, wherein the organic molybdenum complex is present in the crankcase lubricating oil in an amount sufficient to provide at least 50 ppm of molybdenum to the finished lubricating oil.

3. A lubricating composition comprising an organic molybdenum complex comprising the reaction product of:

(i) an alkylphenol substituted with an alkyl group in the para-position;

(ii) an aldehyde source;

(iii) an N-hydroxyethyl substituted diamine selected from the group consisting of 2-(2-aminoethylamino)ethanol, aminopropyldiethanolamine, and aminoethyldiethanolamine; and

(iv) molybdenum trioxide.

4. An antioxidant composition comprising an organic molybdenum complex comprising the reaction product of:

(i) an alkylphenol substituted with an alkyl group in the para-position;

(ii) an aldehyde source;

(iii) an N-hydroxyethyl substituted diamine selected from the group consisting of 2-(2-aminoethylamino)ethanol, aminopropyldiethanolamine, and aminoethyldiethanolamine; and

(iv) molybdenum trioxide.

5. The antioxidant composition according to claim 4, wherein the organic molybdenum complex is present in the composition in an amount sufficient to provide molybdenum in an amount ranging from 75 to 250 ppm.

6. The antioxidant composition according to claim 4, further comprising at least one of diphenylamines, sulfur-containing additives, sulfurized phenate detergents, and ZDDP.

18. A process for reducing the oxidative environment in a lubricating oil composition, the process comprising combining with the lubricating oil composition an effective amount of the antioxidant composition according to claim 4.

7. An anti-wear composition comprising an organic molybdenum complex comprising the reaction product of:

(i) an alkylphenol substituted with an alkyl group in the para-position;

(ii) an aldehyde source;

(iii) an N-hydroxyethyl substituted diamine selected from the group consisting of 2-(2-aminoethylamino)ethanol, aminopropyldiethanolamine, and aminoethyldiethanolamine; and

(iv) molybdenum trioxide.

8. The anti-wear composition according to claim 7, wherein the organic molybdenum complex is present in the composition in an amount sufficient to provide molybdenum in an amount ranging from 50 to 100 ppm.

9. The anti-wear composition according to claim 7, further comprising at least one of sulfur-containing additives and ZDDP.

10. A deposit control composition comprising an organic molybdenum complex comprising the reaction product of:

(i) an alkylphenol substituted with an alkyl group in the para-position;

(ii) an aldehyde source;

(iii) an N-hydroxyethyl substituted diamine selected from the group consisting of 2-(2-aminoethylamino)ethanol, aminopropyldiethanolamine, and aminoethyldiethanolamine; and

(iv) molybdenum trioxide.

11. The deposit control composition according to claim 10, wherein the organic molybdenum complex is present in the composition in an amount sufficient to provide molybdenum in an amount ranging from 75 to 250 ppm.

12. The deposit control composition according to claim 10, further comprising at least one of diphenylamines and sulfurized phenate detergents.

13. A friction modifying composition comprising an organic molybdenum complex comprising the reaction product of:

(i) an alkylphenol substituted with an alkyl group in the para-position;

(ii) an aldehyde source;

(iii) an N-hydroxyethyl substituted diamine selected from the group consisting of 2-(2-aminoethylamino)ethanol, aminopropyldiethanolamine, and aminoethyldiethanolamine; and

(iv) molybdenum trioxide.

14. The friction modifying composition according to claim 13, wherein the organic molybdenum complex is present in the composition in an amount sufficient to provide molybdenum in an amount ranging from 250 to 1000 ppm.

15. The friction modifying composition according to claim 13, further comprising an antioxidant.

16. An additive concentrate composition comprising:

a) an organic molybdenum complex comprising the reaction product of;

(i) an alkylphenol substituted with an alkyl group in the para-position;

(ii) an aldehyde source;

(iii) an N-hydroxyethyl substituted diamine selected from the group consisting of 2-(2-aminoethylamino)ethanol, aminopropyldiethanolamine, and aminoethyldiethanolamine; and

(iv) molybdenum trioxide; and

b) a diluent process oil.

17. The additive concentrate composition according to claim 16, further comprising at least one additive chosen from dispersants, detergents, anti-wear agents, anti-oxidants, viscosity index improvers, pour point depressants, corrosion inhibitors, rust inhibitors, foam inhibitors, and friction modifiers.

21. A process for improving the oxidation stability of a lubricating oil comprising adding to the lubricating oil an oxidation stability improving amount of an organic molybdenum complex comprising the reaction product of:

(i) an alkylphenol substituted with an alkyl group in the para-position;

(ii) an aldehyde source;

(iii) an N-hydroxyethyl substituted diamine selected from the group consisting of 2-(2-aminoethylamino)ethanol, aminopropyldiethanolamine, and aminoethyldiethanolamine; and

(iv) molybdenum trioxide,

wherein the oxidation stability improving amount of the molybdenum complex is sufficient to improve the oxidative stability of the lubricating oil, as compared to the same lubricating oil except that it is devoid of the organic molybdenum complex.

22. The process according to claim 21, wherein the organic molybdenum complex is present in the lubricating oil in an amount sufficient to provide at least 50 ppm of molybdenum to the finished lubricating oil.