Glycidol modified succinimides

• US 4,617,137 A
• Filed: 11/21/1984
• Issued: 10/14/1986
• Est. Priority Date: 11/21/1984
• Status: Expired due to Term

• Current Assignee: Chevron Research Company (Chevron Corp.)
• Original Assignee: Chevron Research Company (Chevron Corp.)
• Inventors: Plavac, Frank
• Primary Examiner(s): Howard, Jacqueline V.
• Application Number:
  US06/673,962
• Time in Patent Office: 692 Days
• Field of Search: 252/51.5 A, 252/49.6, 548/545
• US Class Current: 508/192
• CPC Class Codes: C08F 110/10 Isobutene
• CPC Class Codes: C08F 8/02 Alkylation
• CPC Class Codes: C08F 8/32 by reaction with amines
• CPC Class Codes: C08F 8/48 Isomerisation; Cyclisation
• CPC Class Codes: C10L 1/224 Amides; Imides carboxylic acid amides, imides C10L1/221, C10L1/2227 take precedence
• CPC Class Codes: C10L 1/2383 Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C) C10L1/221 takes precedence
• 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 2215/22 Heterocyclic nitrogen compounds
• CPC Class Codes: C10M 2215/221 Six-membered rings containing nitrogen and carbon only
• CPC Class Codes: C10M 2215/225 the rings containing both nitrogen and oxygen
• CPC Class Codes: C10M 2215/226 Morpholines
• CPC Class Codes: C10M 2215/26 Amines
• CPC Class Codes: C10M 2215/30 Heterocyclic compounds
• 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: C10M 2227/061 Esters derived from boron
• CPC Class Codes: C10N 2040/25 Internal-combustion engines
• CPC Class Codes: C10N 2040/251 : Alcohol-fuelled 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

Disclosed are additives which are useful as dispersants in lubricating oils, gasolines, marine crankcase oils and hydraulic oils. In particular, disclosed are alkenyl or alkyl succinimides which have been modified by treatment with glycidol.

Claims

1. A product produced by the process which comprises contacting at a temperature sufficient to cause reaction an alkenyl or alkyl succinimide containing at least one primary or secondary amine with glycidol wherein the charge mole ratio ranges from greater than 1 and up to 10 of glycidol to each of the basic nitrogens of the alkenyl or alkyl succinimide.

2. A product produced by the process of claim 1 wherein the alkenyl or alkyl group of the alkenyl or alkyl succinimide contains from 20 to 100 carbon atoms.

3. A product produced by the process of claim 2 wherein the process is conducted at from 0°

to 250°

C.

4. A product produced by the process of claim 3 wherein the charge mole ratio ranges from greater than 1 and up to 5 of glycidol to each of the basic nitrogens of the alkenyl or alkyl succinimide.

12. A lubricating oil composition comprising an oil of lubricating viscosity and a dispersant effective amount of a product produced by the process of claim 1.

14. A lubricating oil concentrate comprising from about 90 to 10 weight percent of an oil of lubricating viscosity and from about 10 to 90 weight percent of a product produced by the process of claim 1.

5. A product produced by the process which comprises contacting at a temperature sufficient to cause reaction glycidol with an alkenyl or alkyl succinimide of the formula ##STR6## wherein R is an alkenyl or alkyl group containing from about 10 to 300 carbon atoms;

R₁ is alkylene of 2 to 10 carbon atoms;

R₂ is hydrogen or lower alkyl;

a is an integer from 0 to 10; and

W is --NH₂ or ##STR7## wherein R is an alkenyl or alkyl group containing from about 10 to 300 carbon atoms;

with the proviso that if W is ##STR8## then a is not zero and at least one of R₂ is hydrogen and wherein the charge mole ratio ranges from greater than 1 and up to 10 of glycidol to each of the basic nitrogens of the alkenyl or alkyl succinimide.

6. A product produced by the process of claim 5 wherein R₂ is hydrogen.

7. A product produced by the process of claim 6 wherein R₁ is either ethylene or propylene and W is --NH₂.

8. A product produced by the process of claim 7 wherein a is either 2 or 3.

9. A product produced by the process of claim 8 wherein R is an alkenyl or alkyl group of from 20 to 100 carbon atoms.

10. A product produced by the process of claim 9 wherein the process is conducted at from 0°

to 250°

C.

11. A product produced by the process of claim 10 wherein the charge mole ratio ranges from greater than 1 and up to 5 of glycidol to each of the basic nitrogen of the nitrogens of the alkenyl or alkyl succinimide.

13. A lubricating oil composition comprising an oil of lubricating viscosity and a dispersant effective amount of a product produced by the process of claim 5.

15. A lubricating oil concentrate comprising from about 90 to 10 weight percent of an oil of lubricating viscosity and from about 10 to 90 weight percent of a product produced by the process of claim 5.

16. A product prepared by the process which comprises

(a) contacting at a temperature sufficient to cause reaction an alkenyl or alkyl succinimide containing at least one primary or secondary amine with glycidol wherein the charge mole ratio ranges from greater than 1 and up to 10 of glycidol to each of the basic nitrogens of the alkenyl or alkyl succinimide and

(b) reacting the adduct formed in (a) above with boric acid wherein from about 0.1 equivalents to 10 equivalents of boric acid are employed per equivalent of adduct produced in (a) above.

17. A lubricating oil composition comprising an oil of lubricating viscosity and a dispersant effective amount of a product produced by the process of claim 16.

18. A lubricating oil concentrate comprising from about 90 to 10 weight percent of an oil of lubricating viscosity and from about 10 to 90 weight percent of a product produced by the process of claim 16.