Multifunctional lubricant additive with Viton seal capability

• US 4,973,412 A
• Filed: 05/07/1990
• Issued: 11/27/1990
• Est. Priority Date: 05/07/1990
• Status: Expired due to Fees

• Current Assignee: Ethyl Additives Corp. (Antwerp Distribution & Product Operations NV)
• Original Assignee: Texaco Incorporated (Chevron Corp.)
• Inventors: Migdal, Cyril A., Nalesnik, Theodore E.
• Primary Examiner(s): Chaudhuri, Olik
• Assistant Examiner(s): MCAVOY, ELLEN M
• Application Number:
  US07/519,970
• Time in Patent Office: 204 Days
• Field of Search: 252/49.6, 252/51.5 A, 548/546, 548/547
• US Class Current: 508/192
• CPC Class Codes: C08F 110/10 Isobutene
• CPC Class Codes: C08F 8/32 by reaction with amines
• CPC Class Codes: C10M 133/56 Amides; Imides
• CPC Class Codes: C10M 2215/04 having amino groups bound to acyclic or cycloaliphatic carbon atoms
• CPC Class Codes: C10M 2215/26 Amines
• CPC Class Codes: C10M 2217/046 Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
• CPC Class Codes: C10M 2217/06 Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
• CPC Class Codes: C10N 2040/25 Internal-combustion engines
• CPC Class Codes: C10N 2040/251 Alcohol-fuelled engines
• CPC Class Codes: C10N 2040/252 Diesel engines
• CPC Class Codes: C10N 2040/253 Small diesel engines
• CPC Class Codes: C10N 2040/255 Gasoline engines
• CPC Class Codes: C10N 2040/28 Rotary engines

Abstract

A lubricating oil composition having improved antioxidancy, dispersancy and Viton seal compatibility. The antioxidant-dispersant being prepared by coupling partially acylated succinimides with an organic diacid, followed by further treatment with an unsaturated fatty acid, and then reaction of the nitroso group of an antioxidant aromatic amine with the unsaturated fatty acid to provide the lubricant product.

Claims

1. A lubricating oil composition comprising a major portion of a lubricating oil and a minor antioxidant--dispersant amount of a reaction product prepared by the process which comprises:

(a) reacting a polyethylene amine with an alkenyl succinic acid anhydride to form a mono- and/or bis-alkenyl succinimide;

(b) adding an organic diacid to the mono- and/or bis-alkenyl succinimide, forming a coupled mono- and/or bis-alkenyl succinimide;

(c) acylating the coupled mono- and/or bis-alkenyl succinimide with an unsaturated fatty acid or ester to form an acylated coupled mono- and/or bis-alkenyl succinimide; and

(d) adding a nitroso-aromatic amine to said acylated coupled mono- and/or bis-alkenyl succinimide to form an enamine diphenylamine acylated coupled mono- and/or bis-alkenyl succinimide.

2. The lubricating composition of claim 1, wherein triethylenetetramine is the polyethylene amine and about 0.5-1.0 moles of an unsaturated acid are added per mole of said triethylenetetramine.

3. The lubricating composition of claim 1, wherein tetraethylenepentamine is the polyethylene amine and about 0.5 to 2.0 moles of an unsaturated fatty acid are added per mole of said tetraethylenepentamine.

4. The lubricating composition of claim 1, wherein pentaethylenehexamine is the polyethylene amine and about 0.5-3.0 moles of an unsaturated fatty acid are added per mole of said pentaethylenehexamine.

5. The lubricating oil composition of claim 1, wherein the mole ratio of said alkenyl succinic acid anhydride to said polyethylene amine is about 0.4 to 0.6.

6. The lubricating oil composition of claim 1, wherein said polyethylene amine is represented by the formula ##STR5## where R¹ is H or a hydrocarbon selected from the group consisting of alkyl, alalkyl, cycloalkyl aryl, alkaryl, alkenyl and alkynyl group;

R² is a hydrocarbon selected from the same group as R¹ except that R² contains one less H;

a is an interger of about 1 to about 6; and

n is 0 or 1.

7. The lubricating oil composition of claim 6, wherein said amine is selected from the group consisting of diethylenetriamine, triethylenetetramine, tetraethylenepentamine and pentaethylenehexamine.

8. The lubricating oil composition of claim 7, wherein the mole ratio of said triethylenetetramine to said diacid is about 0.5 to about 0.75.

9. The lubricating oil composition of claim 7, wherein the mole ratio of said tetraethylenepentamine to said diacid is about 0.5 to about 1.0.

10. The lubricating oil composition of claim 7, wherein the mole ratio of said pentaethylenehexamine to said diacid is about 0.5 to 0.5.

11. The lubricating oil composition of claim 7, wherein said amine is tetraethylenepentamine.

12. The lubricating oil composition of claim 7, wherein said amine is pentaethylenehexamine.

13. The lubricating oil composition of claim 7, wherein said amine is triethylenetertramine.

14. The lubricating oil composition of claim 1 wherein said unsaturated fatty acid is selected from group consisting of lauroleic, myristoleic, palmitoleic, oleic, linoleic, linolenic, ricinoleic, licanic, eleostearic, eicosenoic, eicosapolyenoic, erucic, docosapolyenoic, tetracosenoic and tetracosapolyenoic.

15. The lubricating oil composition of claim 1 wherein said diacid/dicarboxylic acid is represented by the following formula

16. The lubricating oil composition of claim 1 wherein the said nitroso aromatic amine is the antioxidant group.

17. The lubricating oil composition of claim 1 wherein said nitroso-aromatic amine is represented by the formula ##STR6## wherein R⁴ is H,--NH₂,--CH₂ --(CH₂)_n --NH CH₂ --aryl--NH₂ in which n has value of 1-10, R⁵ is a (C_4-C24) alkyl, alkenyl, alkoxyl, aralkyl or alkanyl group.

18. The lubricating oil composition of claim 1 wherein said nitroso-aromatic amine is N-(4-nitrosophenyl) naphthyl amine of the formula ##STR7##

19. The lubricating oil composition of claim 12 wherein said unsaturated fatty acid is oleic acid.

20. The lubricating oil composition of claim 13 wherein said diacid is dioleic.

21. The lubricating oil composition of claim 1 wherein the enamine diphenylamine acylated coupled bis-alkenyl succinimide is represented by the formula ##STR8## where R is polyisobutenyl group and R³ is a hydrocarbyl group selected from the group consisting of a (C₂ -C₄₆) alkyl, cycloalkyl, aryl, alkaryl, alkenyl and alkynyl group.

22. The lubricating oil composition of claim 14 wherein said antioxidant group is 4-nitrosodiphenylamine.

23. The lubricating oil composition of claim 1 wherein the number average molecular weight of said PIBSA ranges from about 500 to about 10,000.

24. The lubricating oil composition of claim 1 wherein the number average molecular weight of said PIBSA ranges from about 800 to about 2500.

25. The lubricating oil composition of claim 1 wherein at least a portion of the secondary amine groups of the polyalkenylamine moiety in said enamine diphenylamine acylated coupled mono- and/or bis-alkenyl succinimide are reacted with a second carboxylic acid acylating agent selected from the group consisting of hydroxyaliphatic acids.

26. The lubricating oil composition of claim 25 wherein said hydroxyaliphatic acid contains from to 1 to 4 carbon atoms exclusive of the carbonxyl group.

27. The lubricating oil composition of claim 26, wherein said hydroxyaliphatic acid is glycolic acid.

28. A lubricating oil composition comprising a major portion of a lubricating oil and a minor antioxidant--dispersant amount of a reaction product prepared by the process which comprises:

(a) reacting a polyethylene amine with an alkenyl succinic acid anhydride to form a mono- and/or bis-alkenyl succinimide;

(b) adding an organic diacid to the mono- and/or bis-alkenyl succinimide, forming a coupled mono- and/or bis-alkenyl succinimide;

(c) acylating the coupled mono- and/or bis-alkenyl succinimide with an unsaturated fatty acid or ester to form an acylated coupled mono- and/or bis-alkenyl succinimide;

(d) adding a nitroso-aromatic amine to said acylated coupled mono- and/or bis-alkenyl succinimide to form an enamine diphenylamine coupled mono- and/or bis-alkenyl succinimide; and

(e) adding a borating agent to said enamine diphenylamine acylated coupled mono- and/or bis-alkenyl succinimide to form a borated enamine diphenylamine acylated coupled mono- and/or bis-alkenyl succinimide.

29. The lubricating oil composition of claim 28 wherein said borating agent is selected from the group consisting of boric acid, boric oxide, boron halide and a boron acid ester.

30. The lubricating oil composition of claim 28 wherein instead of said borating agent, a glycolating agent is added to said enamine diphenylamine acylated coupled mono- and/or bis-alkenyl succinimide to form a glycolated enamine diphenyl-amine acylated coupled mono- and/or bis-alkenyl succinimide.

31. The lubricating oil composition of claim 30 wherein said glycolating agent is glycolic acid.