Preparation and use of aminoalkylphosphonic acid dialkyl ester compounds in a lubricant for antiwear, friction reduction, and/or micropitting prevention

Patent metadata

Field	Value
Publication number	US-11149226-B2
Application number	US-202016793255-A
Country	US
Kind code	B2
Filing date	Feb 18, 2020
Priority date	Sep 15, 2011
Publication date	Oct 19, 2021
Grant date	Oct 19, 2021

Abstract

In accordance with the disclosure, one aspect of the present application is directed to a lubricant additive composition. The lubricant additive composition includes a component or mixture of components selected from (a) an aminoalkylphosphonic acid dialkyl ester; (b) a cyclized product of an aminoalkylphosphonic acid dialkyl ester; and a mixture of (a) and (b). Preparation and use of the additive composition in a lubricant for antiwear and/or friction reduction are also disclosed.

First claim

What is claimed is:

1. A lubricant additive composition comprising
a component or mixture of components selected from the group consisting of:
(a) an aminoalkylphosphonic acid dialkyl ester;
(b) a cyclized product of an aminoalkylphosphonic acid dialkyl ester; and
a mixture of (a) and (b); and
at least one diluent oil,

wherein the aminoalkylphosphonic acid dialkyl ester is a compound of formula (I):

wherein each X is independently selected from sulfur and oxygen;
wherein z is 1 to 30;
wherein R and R′ are independently selected from hydrocarbyl radicals containing 3 carbon atoms;
wherein Y is selected from an alkyl group having from about 1 to about 30 carbon atoms, an alcohol having from about 1 to about 30 carbon atoms, and the group R″O(R′″O) n —H, wherein R″ and R′″ are independently divalent aliphatic hydrocarbon radicals containing from about 1 to about 4 carbon atoms and n is an integer from 0 to 20; and
wherein R″″ is selected from hydrogen, an alkyl group having from about 1 to about 30 carbon atoms, an alcohol having from about 1 to about 30 carbon atoms, and the group R″O(R′″O) n —H, wherein R″ and R′″ are independently divalent aliphatic hydrocarbon radicals containing from about 1 to about 4 carbon atoms and n is an integer from 0 to 20.

2. The lubricant additive composition of claim 1 , wherein at least one of Y and R″″ is an alcohol having from about 1 to about 30 carbon atoms.

3. The lubricant additive composition of claim 1 , wherein the aminoalkylphosphonic acid dialkyl ester comprises one or more of
N,N-bis(2-ethyl) aminomethane phosphonic acid dibutyl ester having the formula (II):

N,N-bis(2-butyl) aminomethane phosphonic acid dibutyl ester (formula III); or

N,N-bis(2-hydroxyethyl) aminomethane phosphonic acid dibutyl ester (formula IV)

4. The lubricant additive composition of claim 1 , wherein the cyclized product of an aminoalkylphosphonic acid dialkyl ester comprises a cyclized product of N,N-bis(2-hydroxylethyl) aminomethylphosphonic acid diethyl ester having the formula (V):

5. The lubricant additive composition of claim 1 , wherein the mixture of components further comprises:
(c) a dialkyl (hydroxyalkyl)phosphonate.

6. The lubricant additive composition of claim 5 , wherein the dialkyl (hydroxyalkyl)phosphonate is present in an amount of less than about 20 wt %, but not 0 wt %, based on the total weight percent of the additive composition.

7. The lubricant additive composition of claim 1 , wherein the aminoalkylphosphonic acid dialkyl ester is present in an amount of greater than about 50 wt % based on the total weight percent of the additive composition.

8. The lubricant additive composition of claim 1 , wherein the cyclized product of the aminoalkylphosphonic acid dialkyl ester is present in an amount of greater than about 20 wt % based on the total weight percent of the additive composition.

9. A lubricant composition or a hydraulic fluid composition comprising a base oil and the additive composition as defined in claim 1 .

10. The lubricant composition of claim 9 , wherein the additive composition is present in an amount of greater than about 0.03 wt % in the lubricant composition, and preferably is present in an amount of greater than about 0.05 wt % in the lubricant composition.

11. A method for providing antiwear protection to a lubricated surface, comprising: lubricating a surface with a lubricant composition of claim 9 , wherein preferably the antiwear protection is improved relative to a lubricant composition free of the lubricant additive composition.

12. A method for reducing friction between lubricated surfaces, comprising: lubricating a surface with a lubricant composition of claim 9 , wherein preferably the antiwear protection is improved relative to a lubricant composition free of the lubricant additive composition.

13. A process for preparing an aminoalkylphosphonic acid dialkyl ester compound, comprising
reacting together a dialkyl phosphite, an aldehyde, and a dialkanolamine, wherein the aminoalkylphosphonic acid dialkyl ester comprises a compound of formula (I):

wherein each X is independently selected from sulfur and oxygen;
wherein z is 1 to 30;
wherein R and R′ are independently selected from hydrocarbyl radicals containing 3 carbon atoms;
wherein Y is selected from an alkyl group having from about 1 to about 30 carbon atoms, an alcohol having from about 1 to about 30 carbon atoms, and the group R″O(R′″O) n —H, wherein R″ and R′″ are independently divalent aliphatic hydrocarbon radicals containing from about 1 to about 4 carbon atoms and n is an integer from 0 to 20; and
wherein R″″ is selected from hydrogen, an alkyl group having from about 1 to about 30 carbon atoms, an alcohol having from about 1 to about 30 carbon atoms, and the group R″O(R′″O) n —H, wherein R″ and R′″ are independently divalent aliphatic hydrocarbon radicals containing from about 1 to about 4 carbon atoms and n is an integer from 0 to 20.

Assignees

• Afton Chemical Corp

Inventors

• Ryan Helen T
• Parks-Lee Bevin W
• Soden Jeffrey J
• Wickson Stuart

Classifications

• C10M2223/065

  containing sulfur · CPC title

• C10M2223/06

  having phosphorus-to-carbon bonds · CPC title

• C07F9/6584

  having one phosphorus atom as ring hetero atom · CPC title

• C10N2040/08

  Hydraulic fluids, e.g. brake-fluids · CPC title

• C07F9/4006

  Esters of acyclic acids which can have further substituents on alkyl · CPC title