Composition and method for preventing or reducing low speed pre-ignition in direct injected spark-ignited engines

Patent metadata

Field	Value
Publication number	US-11802255-B2
Application number	US-202016808533-A
Country	US
Kind code	B2
Filing date	Mar 4, 2020
Priority date	Mar 8, 2019
Publication date	Oct 31, 2023
Grant date	Oct 31, 2023

Abstract

Disclosed herein are improved lubricating compositions effective to prevent or reduce low speed pre-ignition in an engine, as well as to prevent or reduce corrosion of engine components. The lubricating compositions include a base oil combined with a calcium chelate complex, optionally in further combination with additional additives.

First claim

What is claimed is:

1. A lubricating composition comprising a base oil and at least one cyclic calcium chelate complex, wherein the calcium chelate complex comprises a complex having the formula:

wherein:
independently represents a single or double bond, provided that valence is satisfied;
Y is selected from O, S, NR n1 ;
Z is selected from O, S, or NR n2 ; and

R 1 , R 2 , R 3 , R n1 , and R n2 are independently selected from R a , OR b , and N(R b ) 2 ;
wherein R a is in each case independently selected from hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl;
R b is in each case independently selected from C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclil; and
wherein any two or more of R 1 , R 2 , R 3 , R n1 , and R n2 can together form a ring.

2. The lubricating composition according to claim 1 , wherein the calcium chelate complex has the formula:

3. The lubricating composition according to claim 1 , wherein R 1 is selected from methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, iso-butoxy, tert-butoxy, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, and tert-butyl.

4. The lubricating composition according to claim 1 , wherein R 3 is selected from methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, iso-butoxy, tert-butoxy, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, and tert-butyl.

5. The lubricating composition according to claim 1 , wherein R 2 is selected from hydrogen, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, iso-butoxy, tert-butoxy, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, and tert-butyl.

6. The lubricating composition according to claim 1 , wherein R 1 and R 2 together form a ring.

7. The lubricating composition according to claim 1 , wherein R 2 and R 3 together form a ring.

8. The lubricating composition according to claim 1 , wherein R 1 , R 2 and R 3 together form a polycyclic ring system.

9. The lubricating composition according to claim 1 , wherein the calcium chelate complex comprises:

wherein R 2a , R 2b , R 2c , and R 2d are independently selected from hydrogen; hydroxy; C 1-22 alkyl; and O—C 1-22 alkyl wherein any two or more of R 1 , R 2a , R 2b , R 2c , and R 2d can together form a ring.

10. The lubricating composition according to claim 9 , wherein the calcium chelate complex comprises:

wherein R k is selected from hydroxyl, amino, C 1-22 alkyl, for instance, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, and tert-butyl pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl; and O—C 1-22 alkyl, for instance methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, iso-butoxy, or tert-butoxy.

11. The lubricating composition according to claim 1 , wherein the calcium chelate complex has the formula:

wherein n is 0, 1 or 2; and R 4a , R 4a′ , R 4b , R 4b′ , R 4c , R 4c′ , R 4d , R 4d′ , R 4e , and R 4e′ are independently selected from hydrogen; hydroxy; C 1-22 alkyl, for instance, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, and tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl; C 1-22 O-alkyl, for instance methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, iso-butoxy, or tert-butoxy; wherein any two or more of R 4a , R 4a′ , R 4b , R 4b′ , R 4c , R 4c′ , R 4d , R 4d′ , R 4e , and R 4e′ can together form a ring, preferably R 4c and R 4c′ are either hydroxyl or amino, preferably R 4b and R 4b′ are each methoxy.

12. The lubricating composition according to claim 1 , wherein Y is NR n1 , and R n1 is C 1-8 alkyl, for instance, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, and tert-butyl; C 1-8 O-alkyl, for instance methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, iso-butoxy, or tert-butoxy.

13. The lubricating composition according to claim 1 , wherein Z is NR n2 , and R n2 is C 1-8 alkyl, for instance, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, and tert-butyl; C 1-8 O-alkyl, for instance methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, iso-butoxy, or tert-butoxy.

14. The lubricating composition according to claim 1 , wherein Y is NR n1 , Z is NR n2 , and R n1 is C 1-8 alkyl, for instance, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, and tert-butyl, R n2 is C 1-8 alkyl, for instance, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, and tert-butyl, and R 2 is hydrogen or methyl.

15. The lubricating composition according to claim 1 , wherein the calcium complex has the formula:

wherein R 6a and R 6d are independently selected from hydrogen or C 1-8 alkyl, and R 6b and R 6c are each

in which R 7a , R 7b , R 7c , and R 7d are independently selected from hydrogen, hydroxyl, C 1-8 alkyl, and O—C 1-8 alkyl; wherein any two or more of R 7a , R 7b , R 7c , and R 7d can together form a ring.

16. The lubricating composition according to claim 1 , wherein the calcium chelate complex has the formula:

wherein R 5a , R 5b , R 5c , and R 5d are independently selected from hydrogen; hydroxy; C 1-22 alkyl, for instance, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, and tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl; C 1-22 O-alkyl, for instance methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, iso-butoxy, or tert-butoxy; wherein any two or more of R 2 , R 5a , R 5b , R 5c , and R 5d can together form a ring.

17. A lubricating composition, comprising a base oil and at least one cyclic chelate complex, wherein the cyclic calcium chelate complex is the reaction product a calcium compound and a ligand having the formula:

wherein
Y is selected from O, S, NR n1 ;
Z is selected from O, S, NR n2 ;
R 1 , R 2 , R 3 , R n1 , and R n2 are independently selected from R a , OR b , and N(R b ) 2 ;

wherein R a is in each case independently selected from hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl;
R b is in each case independently selected from C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl;
wherein R 2a , R 2b , R 2c , and R 2d are independently selected from hydrogen; hydroxy; C 1-22 alkyl; and O—C 1-22 alkyl; wherein any two or more R groups can together form a ring.

18. A lubricating composition comprising a base oil and at least one cyclic calcium chelate complex, wherein the calcium chelate complex is the reaction product of a calcium compound and a ligand compo

Assignees

• Chevron Oronite Co
• Chevron Usa Inc

Inventors

• Elliott Ian G
• Maria Amir Gamal
• Cherpeck Richard Eugene
• Gunawan Theresa Liang

Classifications

• C10M139/00 Primary

  Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00 · CPC title

• C10M139/06

  having a metal-to-carbon bond (metal complexes of unknown constitution C10M159/18) · CPC title

• C10M169/04

  Mixtures of base-materials and additives · CPC title

• C10M2227/09

  Complexes with metals · CPC title

• C10N2010/04

  Groups 2 or 12 · CPC title