Novel additives for lubricants and fuels

• US 20050202980A1
• Filed: 03/10/2004
• Published: 09/15/2005
• Est. Priority Date: 03/10/2004
• Status: Active Grant

• Current Assignee: Afton Chemical Corporation (Newmarket Corporation)
• Original Assignee: Afton Chemical Corporation (Newmarket Corporation)
• Inventors: Loper, John T., Dittmeier, Robert T., Hutchison, David A., Griffin, Paul G.
• Granted Patent: US 7,361,629 B2
• Time in Patent Office: Days
• US Class Current: 508/232
• CPC Class Codes: C10L 1/221 compounds of uncertain formula; reaction products where mixtures of compounds are obtained
• CPC Class Codes: C10M 133/26 containing a nitrogen-to-nitrogen double bond
• CPC Class Codes: C10M 2215/28 Amides; Imides

Abstract

A multi-functional composition for use as an additive for fuels and lubricants. The composition includes an amination product of a hydrocarbyl substituted succinic acylating agent and a mixture containing an aliphatic polyamine and an aromatic polyamine. The molar ratio of aliphatic polyamine to aromatic polyamine in the mixture ranges from about 10:0.1 to about 0.1:10. The amination product contains at least about 0.1 molar equivalent of the polyamine mixture to 1 molar equivalent of the hydrocarbyl substituted succinic acylating agent.

Claims

1. A multi-functional composition for use as an additive for fuels and lubricants comprising an amination product of a hydrocarbyl substituted succinic acylating agent and a mixture comprising an aliphatic polyamine and an aromatic polyamine, wherein the molar ratio of aliphatic polyamine to aromatic polyamine in the mixture ranges from about 10:

0.1 to about 0.1;

10, and wherein the amination product contains at least about 0.1 molar equivalent of the polyamine mixture to 1 molar equivalent of the hydrocarbyl substituted succinic acylating agent.

2. The composition of claim 1, wherein the aliphatic polyamine comprises a substantially linear aliphatic polyamine.

3. The composition of claim 1, wherein the hydrocarbyl substituted succinic acylating agent comprises a compound of the structure:

4. The composition of claim 3, wherein R comprises polyisobutylene (PIB).

5. The composition of claim 1, wherein a molar ratio of acylating agent to amino groups in the mixture ranges from about 1:

1 to about 6;

1.

6. The composition of claim 1, wherein the aromatic polyamine comprises a compound selected from the group consisting of N-phenyl-phenylenediamine, N-naphthyl-phenylene diamine, and substituted aromatic polyamines of the structure:

7. A lubricant composition comprising an oil of lubricating viscosity and from about 0.1 to 10 wt. %, based on the total weight of the lubricant composition, of the amination product of claim 1.

8. A vehicle having moving parts and containing a lubricant for lubricating the moving parts, the lubricant comprising an oil of lubricating viscosity and from about 0.1 to 10 wt. %, based on the total weight of the lubricant composition, of the amination product of claim 1.

55. The composition of claim 4, wherein the polyisobutylene has a methyl vinylidene isomer content of at least about 70% methylvinylidene.

9. A method for making a novel amination product for use as an additive for fuels and lubricants, the amination product having combined dispersant and antioxidant functionality, the method comprising the steps of:

providing a hydrocarbyl substituted succinic acylating agent to a reaction vessel;

heating the acylating agent to an elevated temperature above room temperature;

contacting an aromatic polyamine with an aliphatic polyamine to provide a polyamine mixture, wherein the molar ratio of aliphatic polyamine to aromatic polyamine in the mixture ranges from about 10;

0.1 to about 0.1;

10; and

reacting the amine mixture with the heated acylating agent under an inert atmosphere to provide the novel amination product, wherein the amination product contains at least about 0.1 molar equivalent of the polyamine mixture to 1 molar equivalent of the hydrocarbyl substituted succinic acylating agent.

10. The method of claim 9, wherein the polyamine mixture and acylating agent are reacted in the substantial absence of a surfactant.

11. The method of claim 9, wherein the aliphatic polyamine comprises a substantially linear aliphatic polyamine.

12. The method of claim 9, wherein the hydrocarbyl substituted succinic acylating agent comprises a compound of the structure:

13. The method of claim 12, wherein R comprises polyisobutylene (PIB).

14. The method of claim 9, wherein a molar ratio of acylating agent to amino groups in the mixture ranges from about 1:

1 to about 6;

1.

15. The method of claim 9, wherein the aromatic polyamine comprises a compound selected from the group consisting of N-phenyl-phenylenediamine, N-naphthyl-phenylene diamine, and substituted aromatic polyamines of the structure:

16. A multifunctional composition for use as an additive for fuels and lubricants comprising an amination product made by the method of claim 9.

17. A lubricant composition comprising an oil of lubricating viscosity and from about 0 to 10 wt. %, based on the total weight of the lubricant composition, of the multifunctional composition of claim 16.

18. A fuel composition comprising a hydrocarbyl fuel and from about 0.1 to about 15.0 weight percent based on the total weight of the fuel composition, of the multifunctional composition of claim 16.

19. A lubricant additive comprising an amination product of a hydrocarbyl substituted succinic acylating agent and a mixture comprising at least one aliphatic polyamine and at least one aromatic polyamine, wherein the molar ratio of aliphatic polyamine to aromatic polyamine in the mixture ranges from about 10:

0.1 to about 0.1;

10, and wherein the amination product contains at least about 0.1 molar equivalent of the aromatic polyamine to 1 molar equivalent of the hydrocarbyl substituted succinic acylating agent.

20. The lubricant additive of claim 19, wherein the aliphatic polyamine comprises a substantially linear aliphatic amine.

21. The lubricant additive of claim 19, wherein the hydrocarbyl substituted succinic acylating agent comprises a compound of the structure:

22. The lubricant additive of claim 21, wherein R comprises polyisobutylene (PIB).

23. The lubricant additive of claim 19, wherein a molar ratio of acylating agent to amino groups in the mixture ranges from about 1:

1 to about 6;

1.

24. The lubricant additive of claim 19, wherein the aromatic polyamine comprises a compound selected from the group consisting of N-phenyl-phenylenediamine, N-naphthyl-phenylene diamine, and substituted aromatic polyamines of the structure:

25. A lubricant composition comprising an oil of lubricating viscosity and from about 0.1 to 10 wt. %, based on the total weight of the lubricant composition, of the lubricant additive of claim 19.

26. A fuel additive comprising an amination product of a hydrocarbyl substituted succinic acylating agent and a mixture containing an aliphatic polyamine and an aromatic polyamine, wherein the molar ratio of aliphatic polyamine to aromatic polyamine in the mixture ranges from about 10:

0.1 to about 0.1;

10 and wherein the amination product contains at least about 0.1 molar equivalent of the polyamine mixture to 1 molar equivalent of the hydrocarbyl substituted succinic acylating agent.

27. The fuel additive of claim 26, wherein the aliphatic polyamine comprises a substantially linear aliphatic amine.

28. The fuel additive of claim 26, wherein the hydrocarbyl substituted succinic acylating agent comprises a compound of the structure:

29. The fuel additive of claim 28, wherein R comprises polyisobutylene (PIB).

30. The fuel additive of claim 26, wherein a molar ratio of acylating agent to amino groups in the mixture ranges from about 1:

1 to about 6;

1.

31. The fuel additive of claim 26, wherein the aromatic polyamine comprises a compound selected from the group consisting of N-phenyl-phenylenediamine, N-naphthyl-phenylene diamine, and substituted aromatic polyamines of the structure:

32. A fuel composition comprising a fuel and from about 0.1 to 15 wt. %, based on the total weight of the fuel composition, of the fuel additive of claim 26.

56. A method of fueling a vehicle'"'"'s engine comprising combusting in said engine a fuel comprising a minor amount of a fuel additive of claim 26.

33. A method of lubricating moving parts of a vehicle, the method comprising using as a lubricating oil for one or more moving parts of the vehicle a lubricant composition containing a lubricant and a lubricant additive, the lubricant additive including an amination product of a hydrocarbyl substituted succinic acylating agent and a mixture containing an aliphatic polyamine and an aromatic polyamine, wherein the molar ratio of aliphatic polyamine to aromatic polyamine in the mixture ranges from about 10:

0.1 to about 0.1;

10, and wherein the amination product contains at least about 0.1 molar equivalent of the polyamine mixture to 1 molar equivalent of the hydrocarbyl substituted succinic acylating agent.

34. The method of claim 33, wherein the aliphatic polyamine comprises a substantially linear aliphatic amine.

35. The method of claim 33, wherein the hydrocarbyl substituted succinic acylating agent comprises a compound of the structure:

36. The method of claim 35, wherein R comprises polyisobutylene (PIB).

37. The method of claim 33, wherein a molar ratio of acylating agent to amino groups in the mixture ranges from about 1:

1 to about 6;

1.

38. The method of claim 33, wherein the aromatic polyamine comprises a compound selected from the group consisting of N-phenyl-phenylenediamine, N-naphthyl-phenylene diamine, and substituted aromatic polyamines of the structure:

39. The method of claim 33 wherein the vehicle includes an internal combustion engine having a crankcase and wherein the lubricant composition comprises a crankcase oil present in the crankcase of the vehicle.

40. The method of claim 33 wherein the lubricant composition comprises a drive train lubricant present in an automotive drive train of the vehicle.

41. A method for lubricating moving parts comprising contacting the moving parts with a lubricant composition containing a lubricant and a lubricant additive, the lubricant additive comprising an amination product of a hydrocarbyl substituted succinic acylating agent and a mixture containing an aliphatic polyamine and an aromatic polyamine, wherein the molar ratio of aliphatic polyamine to aromatic polyamine in the mixture ranges from about 10:

0.1 to about 0.1;

10, and wherein the amination product contains at least about 0.1 molar equivalent of the polyamine mixture to 1 molar equivalent of the hydrocarbyl substituted succinic acylating agent.

42. The method of claim 41 wherein the lubricant composition comprises a gear lubricant present in a gear box.

43. The method of claim 41, wherein the aliphatic polyamine comprises a substantially linear aliphatic amine.

44. The method of claim 41, wherein the hydrocarbyl substituted succinic acylating agent comprises a compound of the structure:

45. The method of claim 44, wherein R comprises polyisobutylene (PIB).

46. The method of claim 41, wherein a molar ratio of acylating agent to amino groups in the mixture ranges from about 1:

1 to about 6;

1.

47. The method of claim 41, wherein the aromatic polyamine comprises a compound selected from the group consisting of N-phenyl-phenylenediamine, N-naphthyl-phenylene diamine, and substituted aromatic polyamines of the structure:

48. An oil-soluble composition comprising a compound of the formula:

49. The composition of claim 48, wherein the compound is selected from the group consisting of bis-succinimide-di-amide-amines of the structure:

50. The composition of claim 48, wherein the compound comprises a bis-succinimide-amide containing an intramolecular-cyclized or intermolecular cross-linked amide-amine containing a structure represented by:

51. A lubricant additive containing the composition of claim 49.

52. A lubricant containing the lubricant additive of claim 50.

53. A fuel additive containing the composition of claim 49.

54. A fuel containing the fuel additive of claim 52.

57. An amination product of a hydrocarbyl substituted succinic acylating agent and a mixture comprising at least one aliphatic polyamine and at least one aromatic polyamine, wherein the molar ratio of aliphatic polyamine to aromatic polyamine in the mixture ranges from 10:

0.1 to 0.1;

10, and wherein the amination product contains at least 0.1 molar equivalent of the aromatic polyamine to 1 molar equivalent of the hydrocarbyl substituted succinic acylating agent.