Lubricating compositions comprising an anti-wear/friction modifying agent

Patent metadata

Field	Value
Publication number	US-10501702-B2
Application number	US-201615556927-A
Country	US
Kind code	B2
Filing date	Mar 2, 2016
Priority date	Mar 10, 2015
Publication date	Dec 10, 2019
Grant date	Dec 10, 2019

Abstract

A phosphate complex of a borate ester provides wear- and friction-reducing performance to an engine or driveline device. The complex may be a pyroborate-hydrocarbyl-substituted phosphate adduct. Boric acid may be reacted with a diol to form an ester, then reacting said ester with an ammonium salt of phosphoric acid or a hydrocarbyl-substituted phosphoric acid.

First claim

What is claimed is:

1. A composition comprising an oil of lubricating viscosity and a compound of formula (I):

wherein x+y=4, x is an integer from 1 to 4, y is 0 or an integer from 1 to 3, and each R 1 is independently a hydrocarbyl group having from about 4 to about 22 carbon atoms;
R 1 and R 2 are each independently hydrogen or a hydrocarbyl group containing from about 4 to about 22 carbon atoms, and
on each ring substituted with R 3 to R 6 independently,
(i) n is 0 or 1, one of R 3 and R 4 is CH 2 —O—C(O)—R 7 where R 7 is a hydrocarbyl group containing from about 8 to about 30 carbon atoms, and the other of R 3 and R 4 , and each of R 5 and R 6 is chosen from hydrogen or a methyl group; or
(ii) n is 0 or 1, one of R 3 and R 4 is a hydrocarbyl group containing from about 4 to about 22 carbon atoms and the other of R 3 and R 4 is independently a hydrocarbyl group containing from about 4 to about 22 carbon atoms or hydrogen, and each of R 5 and R 6 is hydrogen; or
(iii) n is 0, R 3 and R 4 are linked, together with the carbons to which they are attached, to form a benzene ring which is substituted with a hydrocarbyl group R 7 containing from about 12 to about 100 carbon atoms, and R 5 and R 6 are not present.

2. The composition of claim 1 , wherein at least one of R 1 and R 2 is a hydrocarbyl group containing from about 4 to about 22 carbon atoms.

3. The composition of claim 1 , wherein on each ring substituted with R 3 to R 6 independently, n is 0 or 1, and
(i) one of R 3 and R 4 is CH 2 —O—C(O)—R 7 where R 7 is a hydrocarbyl group containing from about 8 to about 30 carbon atoms, and the other of R 3 and R 4 , and each of R 5 and R 6 is chosen from hydrogen or a methyl group; or
(ii) one of R 3 and R 4 is a hydrocarbyl group containing from about 4 to about 22 carbon atoms and the other of R 3 and R 4 is independently a hydrocarbyl group containing from about 4 to about 22 carbon atoms or hydrogen, and each of R 5 and R 6 is hydrogen.

4. The composition of claim 1 , wherein, on each ring substituted with R 3 to R 6 independently, n is 0 or 1, one of R 3 and R 4 is —CH 2 —O—C(O)—R 7 where R 7 is a hydrocarbyl group containing from about 8 to about 30 carbon atoms, and the other of R 3 and R 4 , and each of R 5 and R 6 is chosen from hydrogen or a methyl group.

5. The composition of claim 4 , wherein the on each ring substituted with R 3 to R 6 independently, n is 0 or 1, and either R 3 is —CH 2 —O—C(O)—R 7 where R 7 is a hydrocarbyl group containing from about 8 to about 30 carbon atoms, R 6 is a methyl group and R 5 is hydrogen, or R 4 is —CH 2 —O—C(O)—R 7 where R 7 is a hydrocarbyl group containing from about 8 to about 30 carbon atoms, R 5 is a methyl group and R 6 is hydrogen.

6. The composition of claim 1 , wherein, on each ring substituted with R 3 to R 6 independently, n is 0 or 1, one of R 3 and R 4 is a hydrocarbyl group containing from about 4 to about 22 carbon atoms and the other of R 3 and R 4 is independently hydrogen or a hydrocarbyl group containing from about 4 to about 22 carbon atoms, and each of R 5 and R 6 is hydrogen.

7. The composition of claim 6 , wherein the sum of the carbon atoms in the R 3 and the R 4 groups on each ring substituted with R 3 to R 6 is 22 or less.

8. The composition of claim 5 wherein at least one of R 1 or R 2 is a hydrocarbyl group containing at least 8 carbon atoms.

9. The composition of claim 1 , wherein n is 0.

10. The composition of claim 1 , wherein n is 0, R 3 and R 4 are linked, together with the carbons to which they are attached, to form a benzene ring which is substituted with a hydrocarbyl group R 7 containing from about 12 to about 100 carbon atoms, and R 5 and R 6 are absent.

11. The composition of claim 1 , wherein R′ is a hydrocarbyl group containing 8 carbon atoms.

12. The composition according to claim 10 , wherein x=y=2 and R′ is a 2-ethylhexyl group.

13. The composition of claim 1 , wherein the amount of the compound of formula (I) present in the composition is from about 0.5 to about 15 weight percent.

14. The composition of claim 1 , wherein the compound of formula (I) is present in an amount so as to contribute 300 to 1200 ppm phosphorus to the composition.

15. A composition comprising an oil of lubricating viscosity and a compound obtainable by reacting boric acid with a diol to form an ester and reacting said ester with an ammonium salt of phosphoric acid or a hydrocarbyl-substituted phosphoric acid, wherein said diol:
(i) is a partial ester diol having the formula R 3 (OH)CR 6 —(CH 2 ) n —CR 5 R 4 (OH) where n is 0 or 1, one of R 3 and R 4 is —CH 2 —O—C(O)—R 7 , R 7 is a hydrocarbyl group containing from about 8 to about 30 carbon atoms, and the other of R 3 and R 4 and each of R 5 and R 6 is hydrogen or a methyl group, or
(ii) is a hydrocarbyl-containing diol having the formula R 3 (OH)CR 6 —(CH 2 ) n —CR 5 R 4 (OH) where n is 0 or 1, one of R 3 and R 4 is a hydrocarbyl group containing from about 4 to about 22 carbon atoms and the other of R 3 and R 4 is independently a hydrocarbyl group containing from about 4 to about 22 carbon atoms or hydrogen, and each of R 5 and R 6 is hydrogen or a methyl group, or
(iii) is an aromatic diol substituted with a hydrocarbyl group, wherein the hydrocarbyl group contains from about 12 to about 100 carbon atoms.

16. A composition according to claim 15 , wherein said ammonium salt of a phosphoric acid or a hydrocarbyl-substituted phosphoric acid has the formula [NR x R′ y ] + [R 1 R 2 PO 4 ] − , where x+y=4, x is an integer from 1 to 4, y is 0 or an integer from 1 to 3 and each R′ is independently a hydrocarbyl group having from about 4 to about 22 carbon atoms, and R 1 and R 2 are each independently hydrogen or a hydrocarbyl group containing from about 4 to about 22 carbon atoms.

17. A method of lubricating a mechanical device, wherein said method comprises supplying a composition according to claim 1 to said mechanical device.

18. The method of claim 17 , wherein the said mechanical device is an internal combustion engine or a driveline device.

Assignees

• Lubrizol Corp

Inventors

• Sampler Edward P
• Mcguiness Mark J
• Barton William R S
• Kays Deborah
• Nouvel Nicolas I
• Walker Gary M
• Shaw Katherine M

Classifications

• C10N2060/12

  by phosphorus or a compound containing phosphorus, e.g. PxSy · CPC title

• C10N2060/14

  by boron or a compound containing boron · CPC title

• C10N2040/25

  Internal-combustion engines · CPC title

• C10N2030/42

  Phosphor free or low phosphor content compositions · CPC title

• C10N2010/10

  Groups 5 or 15 · CPC title