Lubricant composition

Patent metadata

Field	Value
Publication number	US-9574156-B2
Application number	US-201314101917-A
Country	US
Kind code	B2
Filing date	Dec 10, 2013
Priority date	Dec 28, 2012
Publication date	Feb 21, 2017
Grant date	Feb 21, 2017

Abstract

A lubricant composition comprising lubricating oil and a compound containing phosphorus and an amine of formula I:

wherein R 1 is a hydrocarbon group and at least one of R 1 is selected from: —(C 1 -C 20 )alkyl, —(C 1 -C 20 )alkenyl, —(C 5 -C 20 )cycloalkyl; R is selected from: —(C 4 -C 20 )alkyl, —(C 4 -C 20 )alkenyl, —(C 5 -C 20 )cycloalkyl; and wherein R 2 , R 3 and R 4 are independently selected from: —H, —(C 6 -C 36 )alkyl, —(C 6 -C 36 )alkenyl, —(C 6 -C 36 )cycloalkyl, wherein at least one of R 2 , R 3 and R 4 is not H; X is O or S; Y 1 and Y 2 are selected from S and O; m is 1 or 2, n is 0 or 1, p is 1 or 2, provided that m+n+p=3 and q=0.8 to 1.2*p, wherein the compound provides at least 48 ppm of phosphorus and a molar ratio phosphorus to nitrogen (P/N) in the range of about 0.40 to about 1.50.

First claim

The invention claimed is:

1. A transmission fluid comprising a lubricant composition which is a mixture of:
(a) a major amount of lubricating oil; and
(b) a compound having a phosphorus containing species and an amine having the formula I:

or a solvate, hydrate, or proadditive thereof,
wherein moietie(s) R 1 is/are hydrocarbon groups and at least one of R 1 is selected from the group consisting of: —(C 1 -C 20 )alkyl and —(C 1 -C 20 )alkenyl; R is selected from the group consisting of: —(C 4 -C 20 )alkyl and —(C 4 -C 20 )alkenyl; and wherein R 2 , R 3 and R 4 are independently selected from the group consisting of: —H, linear —(C 10 -C 19 ) alkyl, branched —(C 6 -C 15 ) alkyl, —(C 6 -C 20 ) alkenyl, —(C 6 -C 20 ) cycloalkyl, wherein at least one of R 2 , R 3 and R 4 is not H and contains 8 to 18 carbon atoms; X is O; Y 1 and Y 2 are independently selected from S and O provided that Y 1 and Y 2 are not both S; m is 1 or 2, n is 0 or 1, p is 1 or 2, with the proviso that m+n+p=3 and q=0.8 to 1.2*p,
wherein the compound of formula I provides at least 50 ppm of phosphorus based on the total weight of the lubricant composition and wherein the compound of formula I provides a molar ratio phosphorus to nitrogen (P/N) in the range of from about 0.50 to less than 1.0.

2. The transmission fluid according to claim 1 , wherein the compound having a phosphorus containing species and an amine has the formula II:

or a solvate, hydrate, or proadditive thereof,
wherein moietie(s) R 1 is/are hydrocarbon group(s) and at least one of R 1 is selected from the group consisting of: linear —(C 6 -C 20 )alkyl and —(C 6 -C 20 )alkenyl; and wherein R 2 , R 3 and R 4 are independently selected from the group consisting of: —H, linear —(C 10 -C 19 ) alkyl, branched —(C 6 -C 15 ) alkyl, —(C 6 -C 20 ) alkenyl, —(C 6 -C 20 ) cycloalkyl, wherein at least one of R 2 , R 3 and R 4 is not H and contains 8 to 18 carbon atoms; X is O; m is 1 or 2; p is 1 or 2, with the proviso that m+p=3 and q=0.8 to 1.2*p.

3. The transmission fluid according to claim 2 wherein at least one of R 2 , R 3 and R 4 is a branched —(C 11 -C 14 ) alkyl group.

4. The transmission fluid according to claim 3 wherein at least one of moietie(s) R 1 is not a branched hydrocarbyl group.

5. The transmission fluid of claim 4 , wherein the compound of formula II provides a molar ratio of phosphorus to nitrogen (P/N) of from about 0.50 to about 0.90.

6. The transmission fluid according to claim 1 , wherein the compound having a phosphorus containing species and an amine has the formula III:

or a solvate, hydrate, or proadditive thereof,
wherein moietie(s) R 1 is/are hydrocarbon group(s) and at least one of R 1 is selected from the group consisting of: —(C 4 -C 20 )alkyl and —(C 4 -C 20 )alkenyl; and wherein R 2 , R 3 and R 4 are independently selected from the group consisting of: —H, linear —(C 10 -C 19 ) alkyl, branched —(C 6 -C 15 ) alkyl, —(C 6 -C 20 ) alkenyl, —(C 6 -C 20 ) cycloalkyl, wherein at least one of R 2 , R 3 and R 4 has 8 to 18 carbon atoms; X is O, Y 1 and Y 2 are independently selected from S and O provided that Y 1 and Y 2 are not both S; m is 1 or 2, p is 1 or 2, with the proviso that m+p=3 and q=0.8 to 1.2*p.

7. The transmission fluid according to claim 6 , wherein the compound of formula III provides a molar ratio of phosphorus to nitrogen (P/N) of from about 0.80 to about 0.90.

8. The transmission fluid according to claim 7 , wherein R 3 and R 4 are —H, and R 2 is selected from the group consisting —(C 6 -C 9 ) alkyl, —(C 15 -C 20 ) alkyl, and a mixture of both.

9. The transmission fluid according to claim 8 , wherein the compound of formula III provides at least about 100 ppm of phosphorus based on the total weight of the lubricant composition.

10. The transmission fluid according to claim 1 , wherein the compound having a phosphorus containing species and an amine has the formula V:

wherein R 1 is selected from the group consisting of: —(C 1 -C 20 )alkyl and —(C 1 -C 20 )alkenyl; R is selected from the group consisting of: —(C 4 -C 20 )alkyl, and —(C 4 -C 20 )alkenyl; and wherein R 2 , R 3 and R 4 are independently selected from the group consisting of: —H, linear —(C 10 -C 19 ) alkyl, branched —(C 6 -C 15 ) alkyl, —(C 6 -C 20 ) alkenyl, —(C 6 -C 20 ) cycloalkyl, wherein at least one of R 2 , R 3 and R 4 is not H and contains 8 to 18 carbon atoms; X is O; m is 1, p is 1 and q=0.8 to 1.2*p.

11. The transmission fluid according to claim 1 , wherein said one or more of R 2 , R 3 and R 4 is made by a process of oligomerizing a C 2 -C 6 olefin, in particular wherein the amine

N
⊕

⁢

HR
2

⁢

R
3

⁢

R
4

is made by a process comprising oligomerizing a C 2 -C 6 olefin to provide at least one of R 2 , R 3 and R 4 by amination using HCN and water under acidic conditions or alternatively the amine is made by oligomerizing a C 2 -C 6 olefin to provide at least one of R 2 , R 3 and R 4 , followed by reacting CO and H 2 to generate an alcohol and reacting the alcohol with NH 3 to generate the amine.

12. The transmission fluid of claim 1 , wherein the ratio of molar equivalents of amine to phosphorus containing species is from about 0.8 to about 1.2.

13. The transmission fluid of claim 1 , wherein the lubricant composition has a friction durability greater than about 8,500 cycles using an amended JASO M348:2002 test method, where the μ0/μd value is maintained at less than about 1.1, and a minimum static friction of about 0.1 is maintained.

14. A Process for preparing a transmission fluid comprising a lubricant composition, said process comprising mixing
(a) a major amount of lubricating oil; and
(b) a reaction product prepared by a process comprising the steps of:
(i) providing at least one phosphorus containing species having the formula VII:

or a solvate, hydrate, or proadditive thereof,
wherein moietie(s) R 1 is/are hydrocarbon groups and at least one of R 1 is selected from the group consisting of: —(C 1 -C 20 )alkyl, —(C 1 -C 20 )alkenyl, —(C 5 -C 20 )cycloalkyl; R is selected from the group consisting of: —(C 4 -C 20 )alkyl, —(C 4 -C 20 )alkenyl, —(C 5 -C 20 )cycloalkyl; X is O; Y 1 and Y 2 are independently selected from S and O provided that Y 1 and Y 2 are not both S; m is 1 or 2, n is 0 or 1, p is 1 or 2, with the proviso that m n p=3, and
(ii) contacting the at least one phosphorus containing species with at least one amine having the formula VIII:
NR 2 R 3 R 4   VIII

wherein R 2 , R 3 and R 4 are independently selected from the group consisting of: —H, linear —(C 10 -C 19 ) alkyl, branched —(C 6 -C 15 ) alkyl, —(C 6 -C 20 ) alkenyl, —(C 6 -C 20 )

Assignees

• Afton Chemical Corp

Inventors

• Tang Hong-Zhi
• Saathoff Lee D

Classifications

• C10M2223/065

  containing sulfur · CPC title

• F16D13/74

  Features relating to lubrication · CPC title

• C10M137/12

  having a phosphorus-to-carbon bond · CPC title

• C10M2223/047

  Thioderivatives not containing metallic elements · CPC title

• C10N2030/06

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