IP Library Granted Patent US 11,091,718
Granted Patent B2
US 11,091,718 · App. 16/934,239 · Granted Aug 17, 2021

Ionic liquid containing divalent cation and monovalent anion and lubricant composition comprising same

Inventors: Sang Hye Shin (Daejeon, KR); Ha Na Song (Daejeon, KR); Yu Na Shim (Daejeon, KR); Sun Ae Hwang (Daejeon, KR)
Assignees: SK INNOVATION CO., LTD.; SK LUBRICANTS CO., LTD.
C10M135/10C07C211/63C07C317/44C07F9/11C07F9/5449C10M169/04C10M2203/003C10M2219/044C10N2020/077C10N2030/06
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Quick Facts
Patent No.
US 11,091,718
App. No.
16/934,239
Granted
Aug 17, 2021
Kind
B2
Abstract

Disclosed are an ionic liquid, having wear resistance maintained at low temperatures and containing a divalent cation including at least one of bis(ammonium) and bis(phosphonium) and a monovalent anion including at least one of sulfonate and phosphate, and a lubricant composition including the ionic liquid.

Claims (23)

1. An ionic liquid, comprising:

a divalent cation comprising at least one of bis(ammonium) and bis(phosphonium); and

a monovalent anion comprising sulfonate

wherein the sulfonate has a structure of Chemical Formula 6 below:

wherein in Chemical Formula 6, R 1 and R 2 are each independently hydrogen, (C1-C20)hydrocarbyl, substituted (C1-C20)hydrocarbyl, (C1-C20)heterohydrocarbyl, or substituted (C1-C20)heterohydrocarbyl.

2. The ionic liquid of claim 1 , wherein the bis(ammonium) has a structure of Chemical Formula 1 below:

in Chemical Formula 1, R 1 and R 2 are each independently hydrogen, (C1-C20)hydrocarbyl, substituted (C1-C20)hydrocarbyl, (C1-C20)heterohydrocarbyl, or substituted (C1-C20)heterohydrocarbyl, and

R 3 is (CH 2 ) n , where 1≤n≤20.

3. The ionic liquid of claim 2 , wherein in Chemical Formula 1, R 1 and R 2 are each independently (C1-C20)alkyl, (C2-C20)alkenyl, (C2-C20)alkynyl, (C3-C7)cycloalkyl, (C5-C20)heteroalkyl, (C6-C20)aryl, (C6-C20)ar(C1-C10)alkyl, (C1-C10)alkoxy, (C6-C20)aryloxy, (C1-C10)alkoxycarbonyl(C1-C20)alkyl, or (C1-C20)alkylcarbonyl.

4. The ionic liquid of claim 2 , wherein in Chemical Formula 1, R 1 and R 2 are each independently (C1-C8)alkyl, and R 3 is (CH 2 ) n , where 1≤n≤12.

5. The ionic liquid of claim 1 , wherein the bis(phosphonium) has a structure of Chemical Formula 2 below:

in Chemical Formula 2, R 1 and R 2 are each independently hydrogen, (C1-C20)hydrocarbyl, substituted (C1-C20)hydrocarbyl, (C1-C20)heterohydrocarbyl, or substituted (C1-C20)heterohydrocarbyl, and

R 3 is (CH 2 ) n , where 1≤n≤20.

6. The ionic liquid of claim 5 , wherein in Chemical Formula 2, R 1 and R 2 are each independently (C1-C20)alkyl, (C2-C20)alkenyl, (C2-C20)alkynyl, (C3-C7)cycloalkyl, (C5-C20)heteroalkyl, (C6-C20)aryl, (C6-C20)ar(C1-C10)alkyl, (C1-C10)alkoxy, (C6-C20)aryloxy, (C1-C10)alkoxycarbonyl(C1-C20)alkyl, or (C1-C20)alkylcarbonyl.

7. The ionic liquid of claim 5 , wherein in Chemical Formula 2, R 1 and R 2 are each independently (C1-C8)alkyl, and R 3 is (CH 2 ) n , where 1≤n≤12.

8. The ionic liquid of claim 1 , wherein in Chemical Formula 6, R 1 and R 2 are each independently (C1-C20)alkyl, (C2-C20)alkenyl, (C2-C20)alkynyl, (C3-C7)cycloalkyl, (C5-C20)heteroalkyl, (C6-C20)aryl, (C6-C20)ar(C1-C10)alkyl, (C1-C10)alkoxy, (C6-C20)aryloxy, (C1-C10)alkoxycarbonyl(C1-C20)alkyl, or (C1-C20)alkylcarbonyl.

9. The ionic liquid of claim 1 , wherein in Chemical Formula 6, R 1 and R 2 are each independently (C3-C10)alkyl.

10. A lubricant composition, comprising:

the ionic liquid of claim 1 ;

at least one additive; and

a base oil.

11. The lubricant composition of claim 10 , comprising 0.05 to 20 wt % of the ionic liquid and 0.1 to 50 wt % of the at least one additive.

12. The lubricant composition of claim 11 , wherein the at least one additive is at least one selected from the group consisting of an antioxidant, a metal cleaner, an anticorrosive agent, a foam inhibitor, a pour point depressant, a viscosity modifier, a dispersant and an antiwear agent.

Assignments (3)
MERGER Recorded Jan 21, 2026
From: SK ENMOVE CO., LTD.
To: SK ON CO., LTD.
Reel/Frame 074882/0131 →
CHANGE OF NAME Recorded Jan 23, 2023
From: SK LUBRICANTS CO., LTD.
To: SK ENMOVE CO., LTD.
Reel/Frame 062454/0293 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 22, 2020
From: SHIN, SANG HYE; SONG, HA NA; SHIM, YU NA; HWANG, SUN AE
To: SK INNOVATION CO., LTD.; SK LUBRICANTS CO., LTD.
Reel/Frame 053279/0345 →
Priority Claims (1)
KR 10-2019-0116063 · Sep 20, 2019 · national
Continuity (1)
Related Publication 20210087490A1 · Mar 25, 2021