Friction modifiers for lubricating oils

Patent metadata

Field	Value
Publication number	US-9296971-B2
Application number	US-201414308301-A
Country	US
Kind code	B2
Filing date	Jun 18, 2014
Priority date	Jul 18, 2013
Publication date	Mar 29, 2016
Grant date	Mar 29, 2016

Abstract

A lubricating oil comprising a major amount of a base oil and a minor amount of an additive package, and the additive package comprises at least one friction modifier selected from compounds of the formulae II, III and IV, and carboxylate salts thereof:

wherein R is a linear or branched, saturated, unsaturated, or partially saturated hydrocarbyl having about 8 to about 28 carbon atoms, n is 0 or 1; and the carboxylate salts have a cation that is an alkali metal, alkaline earth metal, group IIB metal, or ammonium cation; and a dispersant and/or a detergent wherein said lubricating oil comprises at total of at least 5 wt. % of the dispersant and/or the detergent. Methods of using the engine oil to improve thin film and/or boundary layer friction in an engine are also provided.

First claim

What is claimed:

1. An internal combustion engine lubricating oil comprising
a major amount of a base oil selected from the group consisting of base oils in Groups II, III, and IV and mixtures thereof, and
a minor amount of an additive package, wherein the additive package comprises one or more friction modifiers selected from compounds of the formulae II, III and IV, and carboxylate salts thereof:

wherein R is a linear or branched, saturated, unsaturated, or partially saturated hydrocarbyl having about 8 to about 28 carbon atoms and n is 0 or 1; and the carboxylate salts have a cation that is an alkali metal, alkaline earth metal, group IIB metal, or ammonium cation,
a dispersant and/or a metal-containing detergent, wherein said lubricating oil comprises a total of at least 5 wt. % of the dispersant and/or the metal-containing detergent; said lubricating oil comprises 0.01 to 5.0 wt. % of said one or more friction modifiers; and wherein said internal combustion engine oil is formulated as a lubricating oil for lubricating an internal combustion engine, and
at least one metal dialkyldithio phosphate salt in an amount sufficient to provide from 200 to 1000 ppm phosphorus to the lubricating oil.

2. The internal combustion engine lubricating oil of claim 1 , wherein the additive package comprises at least two friction modifiers.

3. The internal combustion engine lubricating oil of claim 1 , wherein R has from about 10 to about 25 carbon atoms.

4. The internal combustion engine lubricating oil of claim 1 , wherein R has from about 10 to about 20 carbon atoms.

5. The internal combustion engine lubricating oil of claim 1 , wherein R has from about 10 to about 18 carbon atoms.

6. The internal combustion engine lubricating oil of claim 1 , wherein the at least one metal dialkyldithio phosphate salt comprises at least one zinc dialkyldithio phosphate represented by the formula:

wherein R′ and R″ may be the same or different hydrocarbyl moieties containing from 1 to 18 carbon atoms and the total number of carbon atoms in the zinc dialkyldithio phosphate is at least 5.

7. The internal combustion engine lubricating oil of claim 6 , wherein the R′ and R″ groups are independently selected from ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, 4-methyl-2-pentanyl, amyl, n-hexyl, i-hexyl, n-octyl, decyl, dodecyl, octadecyl, 2-ethylhexyl, phenyl, butylphenyl, cyclohexyl, methylcyclopentyl, propenyl, and butenyl.

8. The internal combustion engine lubricating oil of claim 6 , wherein 100 mole percent of the alkyl groups of the at least one zinc dialkyldithio phosphate are derived from primary alcohol groups.

9. The internal combustion engine lubricating oil of claim 6 , wherein at least 75 mole percent of the alkyl groups of the at least one zinc dialkyldithio phosphate are derived from 4-methyl-2-pentanol.

10. The internal combustion engine lubricating oil of claim 6 , wherein more than 80 mole percent of the alkyl groups of the at least one zinc dialkyldithio phosphate are derived from 4-methyl-2-pentanol.

11. The internal combustion engine lubricating oil of claim 1 , wherein the at least one metal dialkyldithio phosphate salt has two alkyl groups having a total number of carbon atoms of about 5 or greater.

12. The internal combustion engine lubricating oil of claim 1 , comprising at least two metal dialkyldithio phosphate salts wherein a first metal dialkyldithio phosphate salt comprises alkyl groups derived from a primary alcohol and a second metal dialkyldithio phosphate salt comprises alkyl groups derived from a secondary alcohol.

13. The internal combustion engine lubricating oil of claim 1 , wherein the additive package further comprises at least one component selected from the group consisting of antioxidants, antifoam agents, titanium-containing compounds, phosphorus-containing compounds, viscosity index improvers, pour point depressants, and diluent oils.

14. The internal combustion engine lubricating oil of claim 1 , comprising at least one dispersant.

15. The internal combustion engine lubricating oil of claim 1 , comprising at least one metal-containing detergent.

16. An internal combustion engine lubricating oil comprising
a major amount of a base oil selected from the group consisting of base oils in Groups II, III, and IV and mixtures thereof, and
a minor the amount of an additive package, wherein the additive package comprises one or more friction modifiers comprising the reaction product of glutamic acid, aspartic acid, or a mixture thereof and a primary amine represented by R—NH 2 , where R is a linear or branched, saturated, unsaturated, or partially saturated hydrocarbyl having about 8 to about 28 carbon atoms or a carboxylate salt thereof, wherein the carboxylate salt has a cation that is an alkali metal, alkaline earth metal, group JIB metal, or ammonium cation, and
a dispersant and/or a metal-containing detergent, wherein said lubricating oil comprises a total of at least 5 wt. % of the dispersant and/or the metal-containing detergent; said lubricating oil comprises 0.01 to 5.0 wt. % of said one or more friction modifiers; and wherein said internal combustion engine oil is formulated as a lubricating oil for lubricating an internal combustion engine, and
at least one metal dialkyldithio phosphate salt in an amount sufficient to provide from 200 to 1000 ppm phosphorus to the lubricating oil.

17. A method for improving thin film friction and/or boundary layer friction in an internal combustion engine comprising the step of lubricating the internal combustion engine with a lubricating oil comprising
a major amount of a base oil selected from the group consisting of base oils in Groups I, II, III, and IV and mixtures thereof, and
a minor amount of an additive package, wherein the additive package comprises one or more friction modifiers selected from compounds of the formulae II, III and IV, and carboxylate salts thereof:

wherein R is a linear or branched, saturated, unsaturated, or partially saturated hydrocarbyl having about 8 to about 28 carbon atoms and n is 0 or 1; and the carboxylate salts have a cation that is an alkali metal, alkaline earth metal, group IIB metal, or ammonium cation; or a lubricating oil comprising a major amount of a base oil and a minor amount of an additive package, wherein the additive package comprises one or more friction modifiers comprising the reaction product of lysine and a reactant selected from a hydrocarbyl succinic anhydride represented by the formula I:

and a carboxylic acid represented by R—COOH, wherein R is a linear or branched, saturated, unsaturated, or partially saturated hydrocarbyl having about 8 to about 28 carbon atoms, and carboxylate salts thereof, wherein the carboxylate salts have a cation that is an alkali metal, alkaline earth metal, group IIB metal, or ammonium cation, and
wherein said engine oil is formulated as a lubricating oil for lubricating an internal combustion engine.

18. The method of claim 17 , wherein the improved thin film friction and/or boundary layer friction is determined relative to an identical composition in the absence of the one or m

Assignees

• Afton Chemical Corp

Inventors

• Loper John T

Classifications

• C10N2020/071

  Branched chain compounds · CPC title

• C10N2030/06

  Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure · CPC title

• C10M2215/223

  Five-membered rings containing nitrogen and carbon only · CPC title

• C10M133/16 Primary

  Amides; Imides · CPC title

• C10M2219/046

  Overbased sulfonic acid salts · CPC title