Sulfurized catecholate detergents for lubricating compositions

Patent metadata

Field	Value
Publication number	US-10975323-B2
Application number	US-201615781005-A
Country	US
Kind code	B2
Filing date	Dec 7, 2016
Priority date	Dec 15, 2015
Publication date	Apr 13, 2021
Grant date	Apr 13, 2021

Abstract

A lubricating composition includes a sulfurized oxy-substituted aromatic polyol compound and an oil of lubricating viscosity. The sulfurized oxy-substituted aromatic polyol compound includes at least one of a sulfurized oxy-substituted aromatic polyol and a salt of a sulfurized oxy-substituted aromatic polyol. The compound is suitable as a replacement for detergents that contain Cn alkyl phenols derived from oligomers of propylene.

First claim

What is claimed is:

1. A lubricating composition comprising:
at least 0.2 wt. % of a sulfurized oxy-substituted aromatic polyol compound, the compound comprising at least one of a sulfurized oxy-substituted aromatic polyol and a salt of a sulfurized oxy-substituted aromatic polyol; and
an oil of lubricating viscosity,
wherein the sulfurized oxy-substituted aromatic polyol or salt thereof is the reaction product of an oxy-substituted polyol, a sulfurizing agent, and optionally a metal base or a pnictogen base, the oxy-substituted polyol being represented by the formula:

wherein each R 1 is independently selected from hydrocarbyl groups of 1 to 24 carbon atoms, hydroxyl substituted hydrocarbyl groups of 2 to 24 carbon atoms, (poly)ether groups, acyl groups, and mixtures thereof;
each R 2 is selected from hydrocarbyl groups of 1 to 48 carbon atoms, hydroxyl substituted hydrocarbyl groups of 2 to 24 carbon atoms, (poly)ether groups, groups in which two R 2 groups together form a 5- or 6-membered ring, and mixtures thereof;
R 3 is selected from H and hydroxyl substituted hydrocarbyl groups of 2 to 24 carbon atoms, and mixtures thereof;
wherein the oxy-substituted aromatic polyol compound is an oxy-C 1 -C 30 alkyl-substituted catecholate;
n is at least 1; and
m is at least 0.

2. The composition of claim 1 , wherein the sulfurized oxy-substituted aromatic polyol is represented by the formula:

and salts thereof,
R 9 is selected from hydrogen, hydrocarbyl groups of 1 to 18 carbon atoms, phenol, alkylated phenols, catechol, alkylated catechols, oxy-substituted aromatic polyols, and combinations thereof;
R 10 is selected from hydrogen, sulfhydryl, hydroxyl, hydrocarbyl groups of 1 to 48 carbon atoms, hydroxyl substituted hydrocarbyl groups of 2 to 24 carbon atoms, (poly)ether groups, a 5- or 6-membered ring, and mixtures thereof;
n is at least 1;
k is at least 0;
x is at least 1; and
p is at least 1.

3. The composition of claim 2 , wherein R 9 is selected from:

where R 11 is selected from hydrogen, sulfhydryl, and alkyl groups of 1-24 carbon atoms;
R 17 is an aromatic linking group, which is sulfurized or unsulfurized; and
y is at least 1.

4. The composition of claim 1 , wherein the sulfurized oxy-substituted aromatic polyol is represented by the formula:

where R 10 is selected from hydrogen, sulfhydryl, hydroxyl, hydrocarbyl groups of 1 to 48 carbon atoms, hydroxyl substituted hydrocarbyl groups of 2 to 24 carbon atoms, (poly)ether groups, a 5- or 6-membered ring, and mixtures thereof; and
R 11 is selected from hydrogen, sulfhydryl, and alkyl groups of 1-24 carbon atoms.

5. The composition of claim 1 , wherein each R 1 is independently selected from alkyl groups including at least 8 carbon atoms.

6. The composition of claim 1 , wherein the oxy-substituted aromatic polyol compound is an oxy alkyl substituted catecholate.

7. The composition of claim 1 , wherein the oil of lubricating viscosity is at least 10 wt. % of the lubricating composition.

8. The composition of claim 1 , wherein the sulfur-coupled oxy-substituted aromatic polyol compound is at least 1 wt. % of the lubricating composition.

9. The composition of claim 1 , further comprising at least one of the group consisting of additional detergents, antioxidants, dispersants, antiwear agents, friction modifiers, and combinations thereof.

10. The composition of claim 1 , wherein the composition is free of branched para-C 10-20 -alkylphenols.

11. The composition of claim 1 , wherein the oxy-substituted aromatic polyol compound is one in which at least one of two or more hydroxyl groups directly bonded to an aromatic ring is substituted with a non-aromatic organic group, which is thereby bonded to the aromatic ring by the oxygen of what was an OH group.

12. A method of lubricating a mechanical device comprising supplying to the device the lubricating composition of claim 1 .

13. The method of claim 12 , wherein the mechanical device comprises an engine or driveline device.

14. The composition of claim 1 , wherein m is 0.

Assignees

• Lubrizol Corp

Inventors

• Salem Kamalakumari K
• Walker Gary M
• Delbridge Ewan E
• Moreton David J
• Cox Adam
• Barnes W Preston
• Roski James P
• Fahmy Mohamed G

Classifications

• C10N2040/252

  Diesel engines · CPC title

• C10M135/28 Primary

  containing sulfur atoms bound to a carbon atom of a six-membered aromatic ring · CPC title

• C10M2219/089

  Overbased salts · CPC title

• C10M2205/04

  containing aromatic monomers, e.g. styrene · CPC title

• C10M107/00

  Lubricating compositions characterised by the base-material being a macromolecular compound · CPC title