IP Library › Granted Patent US 12,391,898
Granted Patent B2
US 12,391,898 · App. 18/028,859 · Granted Aug 19, 2025

Friction modifier system

Inventors: Taiki Hattori (Shizuoka, JP); Koichi Kubo (Yokohama, JP); William Raymond Ruhe, Jr. (Solano, CA)
Assignees: CHEVRON JAPAN LIMITED; CHEVRON ORONITE COMPANY LLC
C10M169/04C10M133/44C10M135/18C10M141/08C10M2203/003C10M2215/30C10M2219/068C10N2040/25
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Quick Facts
Patent No.
US 12,391,898
App. No.
18/028,859
Granted
Aug 19, 2025
Kind
B2
Abstract

This disclosure describes a lubricant additive. The additive is a friction modifier that includes a molybdenum containing compound and a tertiary amine-containing composition having the following structure: wherein each R 1 and R 5 is independently a linear or branched-chain monovalent hydrocarbyl group having one to about twenty carbon atoms, wherein each R 2 , R 3 , and R 4 is independently a hydrogen, a linear or branched-chain monovalent hydrocarbyl group having one to about twenty carbon atoms, each m is independently from 0 and 4, each p is independently from 0 and 4, for each cyclic moiety m+p is from 2 and 4, and each n is independently from 1 and 6.

Claims (41)

1. A lubricating oil composition comprising:

a) major amount of a base oil; and

b) minor amount of a synergistic friction modifier composition comprising:

i) a molybdenum containing compound; and

ii) a tertiary amine-containing compound having the following structure:

wherein each R 1 and R 5 is independently a linear or branched-chain monovalent hydrocarbyl group having one to about twenty carbon atoms, wherein each R 2 , R 3 , and R 4 is independently a hydrogen, a linear or branched-chain monovalent hydrocarbyl group having one to about twenty carbon atoms, each m is independently from 0 to 4, each p is independently from 0 to 4, for each cyclic moiety m+p is from 2 to 4, and each n is independently from 1 to 6.

2. The lubricating oil composition of claim 1 , wherein the linear or branched-chain monovalent hydrocarbyl group is a branched C 12 to C 20 alkenyl group.

3. The lubricating oil composition of claim 1 , wherein the linear or branched-chain monovalent hydrocarbyl group is a branched C 18 to C 20 alkenyl group.

4. The lubricating oil composition of claim 1 , wherein the tertiary amine-containing additive is present in about 0.1 to 2 wt % by weight of the lubricating oil composition.

5. The lubricating oil composition of claim 1 , wherein the molybdenum containing compound is a molybdenum dithiocarbamate, molybdenum dithiophosphate, molybdenum carboxylate, molybdenum ester, molybdenum amine, or molybdenum amide.

6. The lubricating oil composition of claim 5 , wherein the molybdenum dithiocarbamate is given by the following structure:

wherein R 8 , R 9 , R 10 , and R 11 are each independently hydrogen or a hydrocarbon group including, by way of example, alkyl groups, alkenyl groups, aryl groups, cycloalkyl groups and cycloalkenyl groups, and X 1 , X 2 , X 3 and X 4 are each independently sulfur or oxygen.

7. The lubricating oil composition of claim 1 , wherein the molybdenum containing compound is present in the lubricating oil composition in concentration ranging from about 50 to about 1500 ppm.

8. A method of modifying friction comprising lubricating an engine with a lubricating oil comprising:

a) major amount of base oil; and

b) minor amount of a synergistic friction modifier composition comprising:

i) a molybdenum containing compound; and

ii) a tertiary amine-containing additive having the following structure:

wherein each R 1 and R 5 is independently a linear or branched-chain monovalent hydrocarbyl group having one to about twenty carbon atoms, wherein each R 2 , R 3 , and R 4 is independently a hydrogen, a linear or branched-chain monovalent hydrocarbyl group having one to about twenty carbon atoms, each m is independently from 0 to 4, each p is independently from 0 to 4, for each cyclic moiety m+p is from 2 to 4, and each n is independently from 1 to 6.

9. The method of claim 8 , wherein the linear or branched-chain monovalent hydrocarbyl group is a branched C 12 to C 20 alkenyl group.

10. The method of claim 8 , wherein the linear or branched-chain monovalent hydrocarbyl group is a branched C 18 to C 20 alkenyl group.

11. The method of claim 8 , wherein the tertiary amine-containing additive is present in about 0.1 to 2 wt % by weight of the lubricating oil composition.

12. The method of claim 8 , wherein the molybdenum containing compound is a molybdenum dithiocarbamate, molybdenum dithiophosphate, molybdenum carboxylate, molybdenum ester, molybdenum amine, or molybdenum amide.

13. The method of claim 12 , wherein the molybdenum dithiocarbamate is given by the following structure:

wherein R 8 , R 9 , R 10 , and R 11 are each independently hydrogen or a hydrocarbon group including, by way of example, alkyl groups, alkenyl groups, aryl groups, cycloalkyl groups and cycloalkenyl groups, and X 1 , X 2 , X 3 and X 4 are each independently sulfur or oxygen.

14. The method of claim 8 , wherein the molybdenum containing compound is present in the lubricating oil composition in concentration ranging from about 50 to about 1500 ppm.

15. A lubricating oil composition comprising:

a) major amount of a base oil;

b) a molybdenum containing compound; and

c) a product of a reaction comprising:

i) a hydrocarbyl-substituted succinic anhydride represented by the following structure:

wherein R 6 is a linear or branched-chain monovalent hydrocarbyl group having one to about twenty carbon atoms; and

ii) a cyclic polyamine represented by the following structure:

wherein R 7 is hydrogen or a linear or branched-chain monovalent hydrocarbyl group having one to about twenty carbon atoms, m is from 0 to 4, p is from 0 to 4, m+p is from 2 to 4, and n is from 1 to 6; and

wherein the hydrocarbyl-substituted succinic anhydride to cyclic polyamine ratio is from about 1.5:1 to about 1.6:1.

16. The lubricating oil composition of claim 15 , wherein the cyclic amine is aminoethyl piperazine, aminopropyl piperazine, aminobutyl piperazine, aminoethyl diazepane, or aminoethyl diazocane.

17. The lubricating oil composition of claim 15 , wherein the molybdenum containing compound is a molybdenum dithiocarbamate, molybdenum dithiophosphate, molybdenum carboxylate, molybdenum ester, molybdenum amine, or molybdenum amide.

18. The lubricating oil composition of claim 17 , wherein the molybdenum dithiocarbamate is given by the following structure:

wherein R 8 , R 9 , R 10 , and R 11 are each independently hydrogen or a hydrocarbon group including, by way of example, alkyl groups, alkenyl groups, aryl groups, cycloalkyl groups and cycloalkenyl groups, and X 1 , X 2 , X 3 and X 4 are each independently sulfur or oxygen.

19. The lubricating oil composition of claim 15 , wherein the molybdenum containing compound is present in the lubricating oil composition in concentration ranging from about 50 to about 1500 ppm.

20. The lubricating oil composition of claim 18 , wherein each R 8 , R 9 , R 10 and R 11 independently comprise 6 to 18 carbon atoms.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 12, 2025
From: HATTORI, TAIKI; KUBO, KOICHI
To: CHEVRON JAPAN LTD.
Reel/Frame 071085/0969 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 12, 2025
From: RUHE, JR., WILLIAM RAYMOND
To: CHEVRON ORONITE COMPANY LLC
Reel/Frame 071086/0001 →
Continuity (2)
Provisional Application 63087617 · Oct 5, 2020
Related Publication 20230287291A1 · Sep 14, 2023
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