IP Library Granted Patent US 11,866,671
Granted Patent B2
US 11,866,671 · App. 18/058,635 · Granted Jan 9, 2024

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 11,866,671
App. No.
18/058,635
Granted
Jan 9, 2024
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 (36)

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

wherein

R 1 , R 2 , R 3 , and R 4 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 unsubstituted or substituted with —O—(C 6-20 )aryl, wherein the (C 6 -C 30 )hydrocarbyl is interrupted by 0, 1, 2, 3, 4, or 5 groups independently chosen from —O— and —S—.

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 , and R 4 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 the base oil or lubricant additive is a lubricant additive.

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

R 1 , R 2 , R 3 , and R 4 are independently chosen from —H and —R b ,

the base oil or lubricant additive comprises one R b and not more than one R b , and

R b is —C(O)—O—(C 8 )alkyl, —C(O)—O—(C 14 )alkyl, —C(O)—O—(C 22 )alkyl, —C(O)—O—(C 10 )alkyl, or —C(O)—O—(C 15 )alkyl.

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 is ocyl coumalate, tetradecyl coumalate, docosyl coumalate, or 4-tetradecyloxy-6-methyl-2-pyrone.

11. The base oil or lubricant additive of claim 1 , wherein the base oil or lubricant additive is 4-tetradecyloxy-6-methyl-2-pyrone.

12. The base oil or lubricant additive of claim 1 , wherein the base oil or lubricant additive is tetradecyl coumalate.

13. 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.

14. A lubricant composition comprising:

the base oil or lubricant additive of claim 1 .

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

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

17. The lubricant composition of claim 15 , wherein the base lubricant composition oil comprises a mineral oil, a synthetic oil, or a combination thereof.

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

19. A method of forming the lubricant composition of claim 15 , the method comprises:

combining the base oil or lubricant additive with one or more other components to form the lubricant composition of claim 15 .

20. 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

R 1 , R 2 , R 3 , and R 4 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 unsubstituted or substituted with —O—(C 6-20 )aryl, wherein the (C 6 -C 30 )hydrocarbyl is interrupted by 0, 1, 2, 3, 4, or 5 groups independently chosen from —O— and —S—.

Assignments (2)
CONFIRMATORY LICENSE Recorded Jan 29, 2025
From: IOWA STATE UNIVERSITY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 070054/0009 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 29, 2022
From: KRAUS, GEORGE A; PODOLAK, KYLE; WHITE, DEREK LEE; SUNDARARAJAN, SRIRAM
To: IOWA STATE UNIVERSITY RESEARCH FOUNDATION, INC.
Reel/Frame 061905/0679 →
Continuity (3)
Division 17380766 · Jul 20, 2021
Provisional Application 63059623 · Jul 31, 2020
Related Publication 20230167375A1 · Jun 1, 2023