IP Library Granted Patent US 12,173,247
Granted Patent B2
US 12,173,247 · App. 18/039,500 · Granted Dec 24, 2024

Reaction product of an organic amine and glycidol and its use as a friction modifier

Inventor: Haibo Zhao (The Woodlands, TX)
C10M133/08C10M169/04C10M2215/042C10N2030/06C10N2030/54C10N2040/25
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Quick Facts
Patent No.
US 12,173,247
App. No.
18/039,500
Granted
Dec 24, 2024
Kind
B2
Abstract

The present disclosure generally relates to a friction modifier comprising the reaction product of an organic amine and glycidol and its use in a non-aqueous lubricant composition. There is also provided a method for reducing the friction between sliding parts of an engine by contacting the engine with the non-aqueous lubricant composition.

Claims (18)

1. A non-aqueous lubricant composition comprising a base oil and a friction modifier comprising a reaction product of: (i) an alkyl alkoxylated amine having the formula

where Z is a C 1 -C 30 alkyl group or an alicyclic group or an aryl group, each Z′ is independently hydrogen, methyl or ethyl and e is an integer from about 1 to about 100; (ii) glycidol; and optionally a second organic amine selected from an alkyl amine, an alicyclic amine, an aryl amine, an alkyl alkoxylated monoamine.

2. The non-aqueous lubricant composition of claim 1 , wherein the second organic amine is an alkyl amine having the formula N(R 1 ) 3 where each R 1 is hydrogen or a C 1 -C 50 alkyl group with the proviso that at least one R 1 is hydrogen.

3. The non-aqueous lubricant composition of claim 2 , wherein the second organic amine is an alicyclic amine selected from cyclopentylamine, cyclohexylamine; cycloheptylamine; cyclododecylamine; 4-methylcyclohexylamine, N,N-dimethylcyclohexylamine; hexamethyleneimine, piperidine and isophorone diamine.

4. The non-aqueous lubricant composition of claim 1 , wherein the second organic amine is an aryl amine substituted with a C 1 -C 20 alkyl group.

5. The non-aqueous lubricant composition of claim 1 , wherein Z is a C 1 -C 30 alkyl group.

6. The non-aqueous lubricant composition of claim 1 , wherein the friction modifier is present in an amount in the range of about 0.1% by weight to about 1.5% by weight, based on the total weight of the non-aqueous lubricant composition.

7. The non-aqueous lubricant composition of claim 1 , wherein the base oil is a synthetic oil.

8. The non-aqueous lubricant composition of claim 1 , wherein the base oil is a mineral oil.

9. A method for reducing friction between sliding parts of an engine by contacting the engine with the non-aqueous lubricant composition of claim 1 .

10. A friction reducing additive package comprising the friction modifier of claim 1 and one or more additives selected from an anti-oxidant, an anti-wear additive, a detergent, a dispersant, a second friction modifier, a viscosity index improver, a pour point depressant, a corrosion inhibitor, a defoaming agent, a seal fix, a seal compatibility agent and mixtures thereof.

11. A non-aqueous lubricant composition comprising a base oil and a friction modifier comprising a compound having a formula:

wherein R is an alkyl alkoxylate group having the formula

where Z is an alkyl group, an alicyclic group, an aryl group, each Z′ is independently hydrogen, methyl or ethyl and e is an integer from about 1 to about 100.

12. The non-aqueous lubricant composition of claim 11 , further comprising a second friction modifier compound wherein R is a C 1 -C 25 alkyl group.

13. The non-aqueous lubricant composition of claim 11 , further comprising a second friction modifier compound wherein R is a phenyl group or a phenyl group substituted with a C 1 -C 20 alkyl group.

14. The non-aqueous lubricant composition of claim 11 , wherein R is an alkyl alkoxylate group where Z is a C 1 -C 20 alkyl group, each Z′ is independently hydrogen or methyl and e is an integer from about 1 to about 25.

15. The non-aqueous composition of claim 11 , wherein the second friction modifier comprises at least one of 2,3-dihydroxypropylamine, 1,3-dihydroxypropylamine, Bis(2,3-dihydroxypropyl)amine, Bis(1,3-dihydroxypropyl)amine or (2,3-dihydroxypropyl) (1,3-dihydroxypropyl)amine.

Assignments (3)
SECURITY INTEREST Recorded May 4, 2026
From: HUNTSMAN INTERNATIONAL LLC; HUNTSMAN ADVANCED MATERIALS AMERICAS LLC; HUNTSMAN NANOCOMP LLC; HUNTSMAN PETROCHEMICAL LLC
To: CITIBANK N.A.
Reel/Frame 075498/0663 →
PATENT SECURITY AGREEMENT Recorded Mar 10, 2026
From: HUNTSMAN INTERNATIONAL LLC; HUNTSMAN ADVANCED MATERIALS AMERICAS LLC; HUNTSMAN NANOCAMP LLC; HUNTSMAN PETROCHEMICAL LLC
To: CITIBANK, N.A.
Reel/Frame 075106/0238 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 5, 2023
From: ZHAO, HAIBO
To: HUNTSMAN PETROCHEMICAL LLC
Reel/Frame 064795/0520 →
Continuity (2)
Provisional Application 63126112 · Dec 16, 2020
Related Publication 20240018440A1 · Jan 18, 2024