Hydrocarbyl-substituted mono- and bis-succinimide having polyamine chain linked hydroxyacyl radicals and mineral oil compositions containing same

• US 4,482,464 A
• Filed: 02/14/1983
• Issued: 11/13/1984
• Est. Priority Date: 02/14/1983
• Status: Expired due to Term

• Current Assignee: Ethyl Additives Corp. (Antwerp Distribution & Product Operations NV)
• Original Assignee: Texaco Incorporated (Chevron Corp.)
• Inventors: Karol, Thomas J., Schlicht, Raymond C., Magaha, Harold S.
• Primary Examiner(s): Howard, Jacqueline V.
• Application Number:
  US06/465,941
• Time in Patent Office: 638 Days
• Field of Search: 252/51.5 A, 252/51.5 R
• US Class Current: 508/291
• CPC Class Codes: C07D 207/412 Acyclic radicals containing more than six carbon atoms
• CPC Class Codes: C10M 133/16 Amides; Imides
• 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 2215/042 containing hydroxy groups; Alkoxylated derivatives thereof
• 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

Abstract

A hydrocarbyl-substituted mono- and bis-succinimide having polyamine chain linked hydroxyacyl radicals represented by the formula: ##STR1## in which R is a hydrocarbyl radical having from about 8 to 400 carbon atoms, X is a divalent alkylene or secondary hydroxy-substituted alkylene radical having from 2 to 3 carbon atoms, A is hydrogen or a hydroxyacyl radical from the group consisting of glycolyl, lactyl, 2-hydroxymethyl propionyl and 2,2'"'"'-bis-hydroxymethyl propionyl radicals and in which at least 30 percent of said radicals represented by A are said hydroxyacyl radicals, x is a number from 1 to 6, and R'"'"' is a radical selected from the group consisting of --NH₂, --NHA, or a hydrocarbyl substituted succinyl radical having the formula: ##STR2## in which R and A have the values noted above, and a hydrocarbon oil composition containing same are provided.

Claims

1. A hydrocarbyl-substituted mono- and bis-succinimide having polyamine chain linked hydroxyacyl radicals represented by the formula:

##STR9## in which R is a hydrocarbyl radical having from about 8 to 400 carbon atoms, X is a divalent alkylene or secondary hydroxy substituted alkylene radical having from 2 to 3 carbon atoms, A is hydrogen or a hydroxyacyl radical selected from the group consisting of glycolyl, lactyl, 2-hydroxy-methyl propionyl and 2,2'"'"'-bis-hydroxymethyl propionyl radicals and in which at least 30 percent of said radicals represented by A are said hydroxyacyl radicals, x is a number from 1 to 6, and R'"'"' is a radical selected from the group consisting of --NH₂,--NHA, or a hydrocarbyl substituted succinyl radical having the formula;

##STR10## in which R and A have the values noted above.

2. A hydrocarbyl-substituted mono- and bis-succinimide according to claim 1 in which at least 50 percent of said radicals represented by A are hydroxyacyl radicals.

3. A hydrocarbyl-substituted mono- and bis-succinimide according to claim 1 in which substantially all of said radicals represented by A are hydroxyacyl radicals.

4. A hydrocarbyl-substituted mono- and bis-succinimide according to claim 1 in which at least 30 percent of said radicals represented by A are glycolyl radicals.

5. A hydrocarbyl substituted mono- and bis-succinimide according to claim 1 in which at least 30 percent of said radicals represented by A are lactyl radicals.

17. A mineral oil composition containing from about 0.001 to 80 weight percent of said mineral oil composition of the succinimide of claim 1.

6. An alkenyl succinimide represented by the formula:

##STR11## in which R is an alkenyl radical having from about 50 to 200 carbon atoms, X is a divalent --CH₂ --CH₂ --, or --CH₂ --CHOH--CH₂ --radical, A is hydrogen or a glycolyl radical in which 50 to 100 percent of said radicals represented by A is said glycolyl radical, x is a number from 2 to 4, and R'"'"' is a radical selected form the group consisting of --NH₂ and --NHA in which A has the value noted above.

7. An alkenyl succinimide represented by the formula:

##STR12## in which R is an alkenyl radical having from about 50 to 200 carbon atoms, X is a divalent --CH₂ --CH₂ --, or a divalent --CH₂ --CHOH--CH₂ --radical,

A is hydrogen or a glycolyl radical in which at least 70 percent of said radicals represented by A are said glycolyl radical, x is a number from 2 to 4 and R'"'"' is a radical selected from the group consisting of --NH₂ and --NHA in which A has the value noted above.

8. An alkenyl succinimide according to claim 7 in which 85 to 100 percent of said radicals represented by A are glycolyl radicals.

9. A lubricant composition comprising a major proportion of an oil of lubricating viscosity and a minor dispersant amount of a hydrocarbyl-substituted mono- and bis-succinimide compound having branched hydroxyacyl radicals represented by the formula:

##STR13## in which R is a hydrocarbyl radical having from about 8 to 400 carbon atoms, X is a divalent alkylene or secondary hydroxy substituted alkylene radical having from 2 to 3 carbon atoms, A is hydrogen or a hydroxyacyl radical selected from the group consisting of glycolyl, lactyl, 2-hydroxymethyl propionyl and 2,2'"'"'-bis-hydroxymethyl propionyl radicals and in which at least 30 percent of said radicals represented by A are said hydroxyacyl radicals, x is a number from 1 to 6, and R'"'"' is a radical selected from the group consisting of --NH₂, --NHA or a hydrocarbyl substituted succinyl radical having the formula;

##STR14## in which R and A have the values noted above.

10. A lubricant composition according to claim 9 in which at least 50 percent of said radicals represented by A in said succinimide are hydroxyacyl radicals.

11. A lubricant composition according to claim 9 in which substantially all of said radicals represented by A in said succinimide are hydroxyacyl radicals.

12. A lubricant composition according to claim 9 in which 50 to 100 percent of said radicals represented by A in said succinimide are glycolyl radicals.

13. A lubricant composition according to claim 9 in which at least 70 percent of said radicals represented by A in said succinimide are glycolyl radicals.

14. A lubricant composition according to claim 9 in which 50 to 100 percent of said radicals represented by A in said succinimide are lactyl radicals.

15. A lubricant composition according to claim 9 containing from about 0.01 to 10 weight percent of said compound.

16. A lubricant composition according to claim 9 containing from about 0.5 to 5 weight percent of said compound.