Borate esters of hydrocarbyl-substituted mono- and bis-succinimides containing polyamine chain linked hydroxyacyl groups and lubricating oil compositions containing same

• US 4,554,086 A
• Filed: 04/26/1984
• Issued: 11/19/1985
• Est. Priority Date: 04/26/1984
• Status: Expired due to Fees

• Current Assignee: Ethyl Additives Corp. (Antwerp Distribution & Product Operations NV)
• Original Assignee: Texaco Incorporated (Chevron Corp.)
• Inventors: Karol, Thomas J., Magaha, Harold S.
• Primary Examiner(s): Schofer, Joseph L.
• Assistant Examiner(s): Kulkosky, Peter F.
• Application Number:
  US06/604,188
• Time in Patent Office: 572 Days
• Field of Search: 548/110, 252/51.5 A, 252/49.6
• US Class Current: 508/192
• CPC Class Codes: C10M 133/16 Amides; Imides
• CPC Class Codes: C10M 133/56 Amides; Imides
• CPC Class Codes: C10M 2227/061 Esters derived from boron
• CPC Class Codes: C10N 2040/25 Internal-combustion engines
• CPC Class Codes: C10N 2040/251 Alcohol fueled engines
• CPC Class Codes: C10N 2040/255 Gasoline engines
• CPC Class Codes: C10N 2040/28 Rotary engines
• CPC Class Codes: C10N 2070/02 Concentrating of additives

Abstract

Lubricating oils of improved wear resistance and dispersancy are prepared containing borate esters of hydrocarbyl-substituted mono- and bis-succinimides containing polyamine chain linked hydroxyacyl groups.

Claims

1. A hydrocarbyl-substituted mono-or bis-succinimide containing polyamine chain-linked hydroxyacyl radicals characterized by the formula ##STR24## wherein R is a hydrocarbyl group containing about 8-400 carbon atoms;

R" is a divalent hydrocarbon group;

x is 1-6;

y is 0-3;

R'"'"'" is a divalent hydrocarbon group;

R* is --NH₂, --N(H)R"H ##STR25## or a hydrocarbyl-substituted succinyl group ##STR26##

2. A hydrocarbyl-substituted mono-or bis-succinimide as claimed in claim 1 wherein said R group contains about 80-150 carbon atoms.

3. A hydrocarbyl-substituted mono-or bis-succinimide as claimed in claim 1 wherein x is zero.

4. A hydrocarbyl-substituted mono-or bis-succinimide as claimed in claim 1 wherein x is 2-4.

5. A hydrocarbyl-substituted mono-or bis-succinimide as claimed in claim 1 wherein R" contains two carbon atoms.

6. A hydrocarbyl-substituted mono-or bis-succinimide as claimed in claim 1 wherein R" contains a pendant hydroxyl group.

7. A hydrocarbyl-substituted mono-or bis-succinimide as claimed in claim 1 wherein R* is --NH₂.

8. A hydrocarbyl-substituted mono -or bis-succinimide as claimed in claim 1 wherein R'"'"'"is --CH₂ --.

9. A hydrocarbyl-substituted mono-or bis-succinimide as claimed in claim 1 wherein y is zero.

19. A lubricant composition as claimed in claim 18 wherein a hydrocarbyl-substituted mono-or bis-succinimide as claimed in claim 1 wherein x is zero.

20. A lubricant composition as claimed in claim 18 wherein a hydrocarbyl-substituted mono-or bis-succinimide as claimed in claim 1 wherein x is 2-4.

10. A hydrocarbyl-substituted mono-or bis-succinimide containing polyamine chain-linked hydroxyacyl radicals characterized by the formula ##STR27## wherein x is 1-6.

11. The method of preparing a product hydrocarbyl-substituted mono-or bis-succinimide containing polyamine chain-linked hydroxyacyl radicals characterized by the formula ##STR28## wherein R is a hydrocarbyl group containing about 8-400 carbon atoms;

R" is a divalent hydrocarbon group;

x is 1-6;

y is 0-3;

R'"'"'" is a divalent hydrocarbon group;

R* is --NH₂, --N(H)R"H, ##STR29## or a hydrocarbyl-substituted succinyl group ##STR30## which comprises reacting;

(i) a hydrocarbyl-substituted mono-or bis-succinimide containing polyamine chain-linked radicals characterized by the formula ##STR31## (ii) a hydroxy acid

space="preserve" listing-type="equation">HOOC--R'"'"'"--OH

and

(iii) a boric acid ##STR32## thereby forming said product; and

recovering said product.

12. The method of claim 11 wherein said reaction is carried out in the presence of inert diluent.

13. The method of claim 11 wherein said reaction is carried out at 40°

C.-180°

C.

14. The method of claim 11 wherein said hydroxy acid and said boric acid are added to said succinimide.

15. The method of claim 11 wherein said hydroxy acid and said boric acid are added substantially simultaneously.

16. The method of claim 11 wherein said boric acid is added to the reaction after said hydroxy acid has reacted with said succinimide.

17. The method which comprises reacting

(i) a poly isobutenyl (M_n of 100-10,000) polyethylene imine succinimide ##STR33## (ii) a hydroxy acid HOOC--CH₂ OH and, (iii) a boric acid HOB(OH)₂

in inert diluent at 40°

C.-180°

C. thereby forming product; and

recovering said product.

18. A lubricant composition comprising a major portion of a lubricating oil and a minor effective amount of as additive a hydrocarbyl-substituted mono-or bis-succinimide containing polyamine chain-linked hydroxyacyl radicals characterized by the formula ##STR34## wherein R is a hydrocarbyl group containing about 8-400 carbon atoms;

R" is a divalent hydrocarbon group;

x is 1-6;

y is 0-3;

R'"'"'" is a divalent hydrocarbon group;

R* is --NH₂, --N(H)R"H, ##STR35## or a hydrocarbyl-substituted succinyl group ##STR36##

21. A lubricant composition as claimed in claim 18 wherein R" contains two carbon atoms.

22. A lubricant composition as claimed in claim 18 wherein R" contains a pendant hydroxyl group.

23. A lubricant composition as claimed in claim 18 wherein R* is --NH₂.

24. A lubricant composition as claimed in claim 18 wherein R'"'"'"is --CH₂ --.

25. A lubricant composition as claimed in claim 18 wherein y is zero.

26. A lubricant composition as claimed in claim 18 wherein said additive is present in amount of 1-5 w % of said lubricating oil.

27. A lubricant composition as claimed in claim 18 wherein said additive is ##STR37## wherein x is 1-6.