Oxazoline modified dispersants

Patent metadata

Field	Value
Publication number	US-11046908-B2
Application number	US-201916246030-A
Country	US
Kind code	B2
Filing date	Jan 11, 2019
Priority date	Jan 11, 2019
Publication date	Jun 29, 2021
Grant date	Jun 29, 2021

Abstract

The present disclosure relates to oxazoline modified lubricant additives that have dispersant properties and lubricating oil compositions including such dispersant lubricant additives. The disclosure also relates to the use of lubricant compositions comprising the additives of the disclosure for improving the soot or sludge handling characteristics of an engine lubricant composition while providing robust and consistent frictional performance at the same time.

First claim

What is claimed is:

1. A lubricant dispersant comprising:
a reaction product of a hydrocarbyl substituted succinamide or succinimide dispersant with an oxazoline or an oxazoline derivative to form the lubricant dispersant having one or more imide groups and one or more pendant hydrocarbyl amide groups;
wherein the hydrocarbyl substituted succinamide or succinimide dispersant is derived from a hydrocarbyl substituted acylating agent reacted with a polyalkylene polyamine; and
wherein the hydrocarbyl substituent of the succinamide or the succinimide dispersant is a linear or branched hydrocarbyl group having a number average molecular weight of about 250 to about 5,000 as measured by GPC using polystyrene as a calibration reference.

2. The lubricant dispersant of claim 1 , wherein the oxazoline or the oxazoline derivative includes hydrocarbyl pendant groups in one of oxazoline ring positions 2, 4, 5, or combinations thereof.

3. The lubricant dispersant of claim 2 , wherein the hydrocarbyl pendant groups are selected from C1 to C32 hydrocarbyl, substituted or unsubstituted aromatic, substituted or unsubstituted hetrocyclic aromatic, hydroxyalkyl, and mixtures thereof.

4. The lubricant dispersant of claim 1 , wherein the oxazoline or the oxazoline derivative is selected from the group consisting of 2-ethyl-2-oxazoline; 2-methyl-2-oxazoline; 2-benzyl-4,4-dimethyl-2-oxazoline; 2-ethyl-4,4-dimethyl-2-oxazoline; 2,4,4-trimethyl-2-oxazoline; 4,4-dimethyl-2-oxazoline; 2-(2,6-dimethoxyphenyl)-4,4-dimethyl-2-oxazoline; 2-phenyl-2-oxazoline; 2-[1-(hydroxymethyl) ethyl]oxazoline; mixtures thereof, and derivatives thereof.

5. The lubricant dispersant of claim 1 , wherein the acylating agent is selected from maleic anhydride, maleic acid, malic acid, tartaric acid, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, mesaconic acid, ethylmaleic anhydride, dimethylmaleic anhydride, methylmaleic acid, dimethylmaleic acid, hexylmaleic acid, and combinations thereof.

6. The lubricant dispersant of claim 1 , wherein the one or more pendant hydrocarbyl amide groups extend from amine moieties provided by the polyalkylene polyamine.

7. The lubricant dispersant of claim 6 , wherein the amine moieties are primary amine moieties, secondary amines moieties, or combinations thereof.

8. The lubricant dispersant of claim 6 , further comprising a molar ratio of the oxazoline or the oxazoline derivative to the amine moieties provided from the polyalkylene polyamine reactant of about 0.33:1 to about 6:1 molar equivalents.

9. The lubricant dispersant of claim 1 , wherein the hydrocarbyl substituent is derived from one or more of ethylene, propylene, isopropylene, butylene, isobutylene, octane, hexane, decene, pentylene, isopentylene, neopentylene, or combinations thereof.

10. The lubricant dispersant of claim 1 , wherein the hydrocarbyl substituent is derived from an olefin copolymer.

11. The lubricant dispersant of claim 10 , wherein the olefin copolymer is obtained from ethylene and one or more C3 to C10 alpha olefins.

12. The lubricant dispersant of claim 1 , wherein the hydrocarbyl substituent of the succinamide or the succinimide is the linear or branched hydrocarbyl group having a number average molecular weight of about 250 to about 3,000 as measured by GPC using polystyrene as a calibration reference.

13. The lubricant dispersant of claim 12 , wherein the polyalkylene polyamine has the formula

wherein
each R and R′, independently, is a divalent C1 to C6 alkylene linker;
each R 1 and R 2 , independently, is hydrogen, a C1 to C6 alkyl group, or together with the nitrogen atom to which they are attached form a 5- or 6-membered ring optionally fused with one or more aromatic or non-aromatic rings; and
n is an integer from 0 to 8.

14. The lubricant dispersant of claim 1 , wherein the polyalkylene polyamine is selected from the group consisting of a mixture of polyethylene polyamines having an average of 5 to 7 nitrogen atoms, triethylenetetramine, tetraethylenepentaamine, and combinations thereof.

15. The lubricant dispersant of claim 1 , wherein the reaction product is the hydrocarbyl-substituted succinimide and has a ratio of pendant amide groups to imide groups of about 0.5:1 to about 5:1.

16. A lubricant composition comprising:
a base oil of lubricating viscosity;
a dispersant derived from a hydrocarbyl substituted succinamide or succinimide reacted with an oxazoline or an oxazoline derivative, the dispersant having one or more imide groups and one or more pendant hydrocarbyl amide groups extending from amine moieties thereof;
wherein the hydrocarbyl substituted succinamide or succinimide is derived from a hydrocarbyl substituted succinic anhydride or acid reacted with a polyalkylene polyamine providing the one or more amine moieties; and
wherein the hydrocarbyl substituent of the succinamide or succinimide is a linear or branched hydrocarbyl group having a number average molecular weight of about 250 to about 5,000 as measured by GPC using polystyrene as a calibration reference.

17. The lubricant composition of claim 16 , wherein the oxazoline or the oxazoline derivative includes hydrocarbyl pendant groups in one of oxazoline ring positions 2, 4, 5 or combinations thereof.

18. The lubricant composition of claim 17 , wherein the hydrocarbyl pendant groups are selected from C1 to C32 hydrocarbyl, substituted or unsubstituted aromatic, substituted or unsubstituted hetrocyclic aromatic, hydroxyalkyl, and mixtures thereof.

19. The lubricant composition of claim 16 , wherein the oxazoline or the oxazoline derivative is selected from the group consisting of 2-ethyl-2-oxazoline; 2-methyl-2-oxazoline; 2-benzyl-4,4-dimethyl-2-oxazoline; 2-ethyl-4,4-dimethyl-2-oxazoline; 2,4,4-trimethyl-2-oxazoline; 4,4-dimethyl-2-oxazoline; 2-(2,6-dimethoxyphenyl)-4,4-dimethyl-2-oxazoline; 2-phenyl-2-oxazoline; 2-[1-(hydroxymethyl) ethyl]oxazoline; mixtures thereof, and derivatives thereof.

20. The lubricant composition of claim 16 , wherein the hydrocarbyl substituted succinic anhydride or acid is a hydrocarbyl-substituted maleic anhydride, maleic acid, malic acid, tartaric acid, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, mesaconic acid, ethylmaleic anhydride, dimethylmaleic anhydride, methylmaleic acid, dimethylmaleic acid, hexylmaleic acid, or combinations thereof.

21. The lubricant composition of claim 16 , wherein the amine moieties provided by the polyalkylene polyamine are selected from one of primary amines, secondary amines, or combinations thereof.

22. The lubricant composition of claim 21 , further comprising a molar ratio of the oxazoline or the oxazoline derivative to the amine moieties provided by the polyalkylene polyamine reactant of about 0.33:1 to about 6:1 molar equivalents.

23. The lubricant composition of claim 16 , wherein the hydrocarbyl substituent is a linear or branched hydrocarbyl group having a number average molecular weight of about 250 to about 3,000 as measured by GPC using polystyrene as a calibration reference.

24. The lubricant composition of claim 23 , wherein the polyalkylene polyamine has the formula

wherein
each R and R′, independently, is a divalent C1 to C6 alkylene linker;
each R 1

Assignees

• Afton Chemical Corp

Inventors

• Carranza Arturo
• Jiang Sheng
• Loper John

Classifications

• C10N2020/04

  Molecular weight; Molecular weight distribution · CPC title

• C10M2215/225

  the rings containing both nitrogen and oxygen · CPC title

• C10N2040/25

  Internal-combustion engines · CPC title

• C10M2207/24

  Epoxidised acids; Ester derivatives thereof · CPC title

• C10M2215/28

  Amides; Imides · CPC title