Precoupled mono-succinimide lubricating oil dispersants and viton seal additives

• US 4,713,189 A
• Filed: 08/20/1986
• Issued: 12/15/1987
• Est. Priority Date: 08/20/1986
• Status: Expired due to Term

• Current Assignee: Ethyl Additives Corp. (Antwerp Distribution & Product Operations NV)
• Original Assignee: Texaco Incorporated (Chevron Corp.)
• Inventors: Nalesnik, Theodore E., Benfaremo, Nicholas
• Primary Examiner(s): Dixon, Jr., William R.
• Assistant Examiner(s): Prezlock, Cynthia A.
• Application Number:
  US06/898,275
• Time in Patent Office: 482 Days
• Field of Search: 252/51.5 A, 252/51.5 R
• US Class Current: 508/292
• CPC Class Codes: C10M 159/16 obtained by Mannich reactions
• CPC Class Codes: C10M 2215/04 having amino groups bound to acyclic or cycloaliphatic carbon atoms
• CPC Class Codes: C10M 2215/086 Imides
• CPC Class Codes: C10M 2215/26 Amines
• CPC Class Codes: C10M 2215/28 Amides; Imides
• 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 fueled engines
• CPC Class Codes: C10N 2040/255 Gasoline engines
• CPC Class Codes: C10N 2040/28 Rotary engines

Abstract

A lubricating oil composition having improved dispersancy and viton seal compatibility. The dispersant being prepared by coupling two polyethyleneamines with an aldehyde and a phenol, followed by conversion to a succinimide. The resulting coupled succinimide is then acylated with glycolic acid to form a glycolated Mannich phenol coupled mono-alkenyl succinimide.

Claims

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

(a) reacting a polyethyleneamine with a phenolic compound in the presence of excess formaldehyde to form a Mannich phenol coupled polyethyleneamine;

(b) reacting said Mannich phenol coupled polyethyleneamine with an alkenyl succinic acid anhydride to form a Mannich phenol coupled mono-alkenyl succinimide;

(c) acylating said coupled mono-alkenyl succinide with glycolic acid to form a glycolated Mannich phenol coupled mono-alkenyl succinimide; and

(d) recovering said glycolated Mannich phenol coupled mono-alkenyl succinimide.

2. The lubricating oil composition of claim 1, wherein said polyethylene amine is represented by the formula ##STR5## where R'"'"' is H or a hydrocabon selected from the group consisting of alkyl, alkalyl, cycloalkyl, aryl, alkaryl, alkenyl and alkynyl group;

R" is a hydrocarbon selected from the same group as R'"'"' except that R" contains one less H;

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

n is 0 or 1.

3. The lubricating oil composition of claim 1, wherein said amine is selected from the group consisting of ethylenediamine, propylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine and pentaethylenehexamine.

4. The lubricating oil composition of claim 1, wherein said amine is tetraethylenepentamine.

5. The lubricating oil composition of claim 1, wherein said amine is pentaethylenehexamine.

6. The lubricating oil composition of claim 1, wherein said amine is triethylenetetramine.

7. The lubricating oil composition of claim 1, wherein oxalic acid is substituted for glycolic acid.

8. The lubricating oil composition of claim 1, wherein said acid aldehyde is selected from the group consisting of formaldehyde, paraformaldehyde, ethanal, propanal and butanal.

9. The lubricating oil composition of claim 8, wherein said aldehyde is paraformaldehyde.

10. The lubricating oil composition of claim 1, wherein said phenol is selected from the group consisting of phenol, bisphenol A, resorcinol, and beta-naphthol.

11. The lubricating oil composition of claim 1, wherein said phenol is phenol.

12. The lubricating oil composition of claim 11, wherein said phenol is 4-nonylphenol.

13. The lubricating oil composition of claim 1, wherein said reaction product is an acylated Mannich phenol coupled glycamide mono-alkenyl succinimide ##STR6## where R is polyisobutenyl and x is an integer of 1 to 6.

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

(a) reacting a polyethyleneamine with a phenolic compound in the presence of excess formaldehyde to form a Mannich phenol coupled polyethyleneamine ##STR7## wherein x is an integer of from 1 to 6;

(b) reacting said Mannich phenol coupled polyethyleneamine with enough alkenyl succinic acid anhydride (ASAA) to ensure complete imidization and give the Mannich coupled alkenyl succinimide ##STR8## wherein R is polyisobutenyl (c) acylating said mono-alkenyl succinimide with glycolic acid to form a glycolated Mannich phenol coupled mono-alkenyl succinimide ##STR9## and (d) recovering said glycolated Mannich phenol coupled mono-alkenyl succinimide.