IP Library Granted Patent US 11,542,454
Granted Patent B2
US 11,542,454 · App. 17/380,766 · Granted Jan 3, 2023

Base oil or lubricant additive

Inventors: George A. Kraus (Ames, IA); Kyle Podolak (Ames, IA); Derek Lee White (Lakewood, CO); Sriram Sundararajan (Ames, IA)
Assignee: Iowa State University Research Foundation, Inc.
C10M129/70C10M169/04C10M2203/003C10M2207/281C10M2207/284C10N2030/06
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Quick Facts
Patent No.
US 11,542,454
App. No.
17/380,766
Granted
Jan 3, 2023
Kind
B2
Abstract

The present invention is toward a base oil or lubricant additives, methods of using the same, lubricant compositions including the same, and methods of forming the lubricant compositions. A base oil or lubricant additive has Structure I or Structure II as described herein.

Claims (34)

1. A base oil or lubricant additive having the structure:

wherein

X is —O— or —NH—,

R 1 , R 2 , R 3 , R 4 , R a1 , R a2 , R a3 , and R a4 are independently chosen from —H, —(C 1 -C 5 )hydrocarbyl and —R b , or the structure is structure II and R a1 and R a2 together form a fused phenyl ring and R 1 , R 2 , R a3 , and R a4 are independently chosen from —H, —(C 1 -C 5 )hydrocarbyl and —R b , or the structure is structure II and R a3 and R a4 together form a fused phenyl ring and R 1 , R 2 , R a1 , and R a2 are independently chosen from —H, —(C 1 -C 5 )hydrocarbyl and —R b ,

the base oil or lubricant additive comprises at least one R b ,

at each occurrence, R b is independently chosen from —C(O)—O—R c , —O—R c , —S—R c , and —NH—R c , and

at each occurrence, R c is independently (C 6 -C 30 )hydrocarbyl that is interrupted by 0, 1, 2, 3, or 5 groups independently chosen from —O— and —S— and that is unsubstituted or substituted with —O—(C 6-20 )aryl.

2. The base oil or lubricant additive of claim 1 , wherein the base oil or lubricant comprises one and not more than one —R b .

3. The base oil or lubricant additive of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R a1 , R a2 , R a3 , and R a4 are independently chosen from —H, methyl, and R b .

4. The base oil or lubricant additive of claim 1 , wherein each occurrence, R b is independently chosen from —C(O)—O—R c .

5. The base oil or lubricant additive of claim 1 , wherein at each occurrence, R c is independently (C 13 -C 15 )alkyl.

6. The base oil or lubricant additive of claim 1 , wherein at each occurrence, R c is independently —((CH 2 —CH 2 )—O) n —CH 3 , wherein n is 1 to 10; —(C 6 -C 30 )alkyl-O-phenyl, or —(C 6 -C 30 )alkyl-O-naphthyl.

7. The base oil or lubricant additive of claim 1 , wherein X is —O—.

8. The base oil or lubricant additive of claim 1 , wherein the base oil or lubricant additive is a lubricant additive.

9. The base oil or lubricant additive of claim 1 , wherein the base oil or lubricant additive has one of the following structures:

10. The base oil or lubricant additive of claim 1 , wherein the base oil or lubricant additive has one of the following structures:

11. The base oil or lubricant additive of claim 1 , wherein the base oil or lubricant additive is 4-tetradecyloxy coumarin.

12. The base oil or lubricant additive of claim 1 , wherein the base oil or lubricant additive exhibits anti-wear properties, friction-reducing properties, or a combination thereof.

13. A lubricant composition comprising:

the base oil or lubricant additive of claim 1 .

14. The lubricant composition of claim 13 , wherein the base oil or lubricant additive is a lubricant additive, wherein the lubricant composition further comprises a base lubricant composition oil.

15. The lubricant composition of claim 14 , wherein the lubricant additive is 0.1 wt % to 20 wt % of the lubricant composition.

16. The lubricant composition of claim 14 , wherein the base lubricant composition oil comprises a mineral oil, a synthetic oil, or a combination thereof.

17. The lubricant composition of claim 16 , wherein the mineral oil is an API Group III mineral oil.

18. A method of forming the lubricant composition of claim 14 , the method comprises:

combining the base oil or lubricant additive with one or more other components to form the lubricant composition of claim 14 .

19. A method of lubricating comprising:

applying a base oil or lubricant additive, or a lubricant composition comprising the same, to an apparatus to lubricate the apparatus, wherein the base oil or lubricant additive has the structure:

wherein

X is —O— or —NH—,

R 1 , R 2 , R 3 , R 4 , R a1 , R a2 , R a3 , and R a4 are independently chosen from —H, —(C 1 -C 5 )hydrocarbyl and —R b , or the structure is structure II and R a1 and R a2 together form a fused phenyl ring and R 1 , R 2 , R a3 , and R a4 are independently chosen from —H, —(C 1 -C 5 )hydrocarbyl and —R b , or the structure is structure II and R a3 and R a4 together form a fused phenyl ring and R 1 , R 2 , R a1 , and R a2 are independently chosen from —H, —(C 1 -C 5 )hydrocarbyl and —R b ,

the base oil or lubricant additive comprises at least one R b ,

at each occurrence, R b is independently chosen from —C(O)—O—R c , —O—R c , —S—R c , and —NH—R c , and

at each occurrence, R c is independently (C 6 -C 30 )hydrocarbyl that is interrupted by 0, 1, 2, 3, or 5 groups independently chosen from —O— and —S— and that is unsubstituted or substituted with —O—(C 6-20 )aryl.

Assignments (3)
CONFIRMATORY LICENSE Recorded May 21, 2024
From: IOWA STATE UNIVERSITY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 067472/0588 →
CONFIRMATORY LICENSE Recorded Jan 23, 2024
From: IOWA STATE UNIVERSITY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 066361/0963 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 26, 2021
From: KRAUS, GEORGE A; PODOLAK, KYLE; WHITE, DEREK LEE; SUNDARARAJAN, SRIRAM
To: IOWA STATE UNIVERSITY RESEARCH FOUNDATION, INC.
Reel/Frame 057296/0069 →
Continuity (2)
Provisional Application 63059623 · Jul 31, 2020
Related Publication 20220033729A1 · Feb 3, 2022