IP Library › Granted Patent US 11,041,137
Granted Patent B2
US 11,041,137 · App. 15/031,898 · Granted Jun 22, 2021

Lubricant composition comprising hydroxycarboxylic acid derived friction modifier

Inventors: Xin Chen (Hockessin, DE); Alexei Nikolaevich Kurchan (Wallingford, PA)
Assignee: Croda, Inc.
C10M169/042C10M129/76C10M145/38C10M159/12C10M2203/1025C10M2207/283C10M2207/289C10M2209/102C10M2209/109C10N2030/06C10N2040/04C10N2040/22C10N2040/25
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 11,041,137
App. No.
15/031,898
Granted
Jun 22, 2021
Kind
B2
Abstract

The present invention relates to a lubricant composition containing a base stock and at least 0.01 wt % of a friction reducing additive which is a compound of the Formula (I): R 1 [(AO) n —R 2 ] m   (I) wherein R 1 is the residue of a group having at least 2 active hydrogen atoms; m is at least 2; AO is an alkylene oxide residue; each n is independently from 0 to 100; and each R 2 is independently H or R 3 , where each R 3 is independently a residue of a polyhydroxyalkyl or polyhydroxyalkenyl carboxylic acid, a residue of a hydroxyalkyl or hydroxyalkenyl carboxylic acid and/or a residue of an oligomer of the hydroxyalkyl or hydroxyalkenyl carboxylic acid; and on average at least 0.5 of R 2 groups are R 3 . The lubricant composition is suitable for use in an engine oil, a hydraulic oil or fluid, a gear oil and/or a metal-working fluid.

Claims (42)

1. A lubricant composition comprising a base stock and at least 0.10 wt % of a friction reducing additive which comprises a compound of Formula (I):

R 1 [(AO) n —R 2 ] m   (I)

wherein:

R 1 is a residue of a monosaccharide or a disaccharide;

m is 4 to 10;

AO is an alkylene oxide residue, where A is —(C r H 2r O)— and r is 2, 3 or 4;

each n is independently from 2 to 20;

each R 2 is independently H or R 3 , where each R 3 is independently a residue of a polyhydroxyalkyl or polyhydroxyalkenyl carboxylic acid, a residue of a hydroxyalkyl or hydroxyalkenyl carboxylic acid and/or a residue of an oligomer of the hydroxyalkyl or hydroxyalkenyl carboxylic acid; and

on average at least 0.5 of R 2 groups are R 3 ,

wherein the lubricant composition is non-aqueous,

wherein the product of indices n×m is 10 to 100, and

wherein the friction reducing additive has a molecular weight (Mn) between 3,000 to 10,000, and is capable of reducing a coefficient of friction of the lubricant composition by at least 20% when measured using a mini-traction machine (MTM).

2. The lubricant composition according to claim 1 wherein R 1 is a residue of a monosaccharide selected from the group consisting of glucose, fructose and sorbitol or a residue of a disaccharide selected from the group consisting of maltose, palitose, lactitol and lactose.

3. The lubricant composition according to claim 1 wherein m is 5 to 6.

4. The lubricant composition according to claim 1 wherein n×m is 25 to 100.

5. The lubricant composition according to claim 1 wherein at least 2.0 of the R 2 groups are R 3 .

6. The lubricant composition according to claim 1 wherein R 3 is a residue of a polyhydroxyalkyl carboxylic acid.

7. The lubricant composition according to claim 6 wherein the number of hydroxyalkyl monomers in the polyhydroxyalkyl carboxylic acid residue is 3 to 10.

8. The lubricant composition according to claim 1 wherein at least 2.0 of the R 2 groups are H.

9. The lubricant composition according to claim 1 wherein the friction reducing additive is an ethoxylated sorbitol ester of a polyhydroxyalkyl carboxylic acid.

10. The lubricant composition according to claim 1 wherein the base stock is selected from the group consisting of an API Group I, II, III, IV, V base oil or mixtures thereof.

11. The lubricant composition according to claim 1 wherein the lubricant composition is a gear oil.

12. The lubricant composition according to claim 1 wherein the lubricant composition is an engine oil.

13. An engine comprising the lubricant composition according to claim 12 .

14. A method of reducing friction in an automotive engine which comprises using an engine oil comprising a base stock and at least 0.01 wt % of a friction reducing additive which comprises a compound of the Formula (I):

R 1 [(AO) n —R 2 ] m   (I)

wherein:

R 1 is a residue of a monosaccharide or a disaccharide;

m is 4 to 10;

AO is an alkylene oxide residue, where A is —(C r H 2r O)— and r is 2, 3 or 4;

each n is independently from 2 to 20; and

each R 2 is independently H or R 3 , where each R 3 is independently a residue of a polyhydroxyalkyl or polyhydroxyalkenyl carboxylic acid, a residue of a hydroxyalkyl or hydroxyalkenyl carboxylic acid and/or a residue of an oligomer of the hydroxyalkyl or hydroxyalkenyl carboxylic acid; and

on average at least 0.5 of R 2 groups are R 3 ,

wherein the engine oil is non-aqueous,

wherein the product of indices n×m, is 10 to 100, and

wherein the friction reducing additive has a molecular weight (Mn) between 3,000 to 10,000, and is capable of reducing a coefficient of friction of the lubricant composition by at least 20% when measured using a mini-traction machine (MTM).

15. The lubricant composition according to claim 1 wherein the residue of a polyhydroxyalkyl or polyhydroxyalkenyl carboxylic acid, the residue of a hydroxyalkyl or hydroxyalkenyl carboxylic acid and/or the residue of an oligomer of the hydroxyalkyl or hydroxyalkenyl carboxylic acid is derived from a hydroxyalkyl or hydroxyalkenyl carboxylic acid of formula HO—X—COOH where X is a divalent saturated or unsaturated aliphatic radical containing 8 to 20 carbon atoms.

16. The method according to claim 14 wherein the residue of a polyhydroxyalkyl or polyhydroxyalkenyl carboxylic acid, the residue of a hydroxyalkyl or hydroxyalkenyl carboxylic acid and/or the residue of an oligomer of the hydroxyalkyl or hydroxyalkenyl carboxylic acid is derived from a hydroxyalkyl or hydroxyalkenyl carboxylic acid of formula HO—X—COOH where X is a divalent saturated or unsaturated aliphatic radical containing 8 to 20 carbon atoms.

17. The lubricant composition according to claim 1 , where R 1 is a residue of a monosaccharide selected from the group consisting of glucose, fructose and sorbitol.

18. The method according to claim 14 , where R 1 is a residue of a monosaccharide selected from the group consisting of glucose, fructose and sorbitol.

19. The lubricant composition according to claim 1 , where r is 2.

20. The method according to claim 14 , where r is 2.

Assignments (2)
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE ADDRESS PREVIOUSLY RECORDED AT REEL: 038486 FRAME: 0614. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT . Recorded Apr 16, 2021
From: CHEN, XIN; KURCHAN, ALEXEI NIKOLAEVICH
To: CRODA, INC.
Reel/Frame 055953/0098 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 6, 2016
From: CHEN, XIN; KURCHAN, ALEXEI NIKOLAEVICH
To: CRODA, INC.
Reel/Frame 038486/0614 →
Continuity (2)
Provisional Application 61896990 · Oct 29, 2013
Related Publication 20160264907A1 · Sep 15, 2016