Borated polyol ester of hindered phenol antioxidant/friction modifier with enhanced performance

Patent metadata

Field	Value
Publication number	US-9752093-B2
Application number	US-201514730587-A
Country	US
Kind code	B2
Filing date	Jun 4, 2015
Priority date	Jun 4, 2015
Publication date	Sep 5, 2017
Grant date	Sep 5, 2017

Abstract

The present invention is directed to compounds comprising the reaction products of a phenolic ester polyol, a boron containing compound, and optionally, an alcohol. Also disclosed are compounds comprising the reaction products of a polyol, a boron containing compound, and a phenolic acid or ester.
Lubricating oil compositions and additive concentrates comprising above compounds, and methods for operating an internal combustion engine using said lubricating oil compositions are also disclosed.

First claim

What is claimed is:

1. A compound comprising the reaction product of:
a. a phenolic ester polyol, wherein the phenolic ester polyol has the following formula (I):

wherein Q is an alkylene group of 2 to 6 carbon atoms; each m is independently 1, 2, or 3; each p is independently 0, 1, 2, or 3; each q is independently 0, 1, 2, or 3; x is 0, 1, or 2; R 1 and R 2 are each independently a C 1 -C 12 alkyl group; R 5 is H, a C 1 -C 12 alkyl group, or a C 1 -C 3 alkanol; and R 6 is H, a C 1 -C 12 alkyl group, or a C 1 -C 3 alkanol;
b. a boron containing compound; and
c. optionally, an alcohol.

2. The compound of claim 1 , wherein the phenolic ester polyol is selected from the group consisting of a glycerol ester of a propionate phenol, diglycerol ester of a propionate phenol, pentaerythritol ester of a propionate phenol, and a trimethylolethane ester of a propionate phenol.

3. The compound of claim 1 , wherein the alcohol is a linear or branched aliphatic alcohol.

4. The compound of claim 1 , wherein the alcohol is a monool or polyol.

5. A compound having the following formula (IV):

wherein Q is an alkylene group of 2 to 6 carbon atoms; each m is independently 1, 2, or 3; each p is independently 0, 1, 2, or 3; each q is independently 0, 1, 2, or 3; x is 0, 1, or 2; R 1 and R 2 are each independently a C 1 -C 12 alkyl group; R 3 is absent or a C 1 -C 12 alkoxy group; R 4 is absent or a C 1 -C 12 alkoxy group; R 5 is H, a C 1 -C 12 alkyl group, or a C 1 -C 3 alkanol; and R 6 is H, a C 1 -C 12 alkyl group, or a C 1 -C 3 alkanol.

6. A compound having the following formula (V):

wherein Q is an alkylene group of 2 to 6 carbon atoms; each m is independently 1, 2, or 3; each p is independently 0, 1, 2, or 3; each q is independently 0, 1, 2, or 3; x is 0, 1, or 2; R 1 and R 2 are each independently a C 1 -C 12 alkyl group; R 5 is H, a C 1 -C 12 alkyl group, or a C 1 -C 3 alkanol; and R 6 is H, a C 1 -C 12 alkyl group, or a C 1 -C 3 alkanol.

7. The compound of claim 5 , wherein the compound has the following formula (VI):

wherein R 1 , R 2 , R 3 , R 4 , R 5 , m, p, and q are as defined in claim 5 .

8. The compound of claim 5 , wherein the compound has the following formula (VII):

wherein R 1 , R 2 , R 3 , R 4 , and R 5 are as defined in claim 5 .

9. The compound of claim 5 , wherein the compound has the following structure (VIII):

wherein R 1 , R 2 , R 3 , and R 5 are as defined in claim 5 .

10. The compound of claim 6 , wherein the compound has the structure of formula (IX):

wherein R 1 , R 2 , and R 5 are as defined in claim 6 .

11. The compound of claim 5 , wherein R 1 and R 2 are both t-butyl groups.

12. The compound of claim 6 , wherein R 1 and R 2 are both t-butyl groups.

13. A compound comprising the reaction product of:
a. a polyol,
b. a boron containing compound, and
c. a phenolic acid or ester, wherein the polyol has the following formula (III):

wherein each m is independently 1, 2, or 3; each p is independently 0, 1, 2, or 3; each q is independently 0, 1, 2, or 3; x is 0, 1, or 2; R 5 is H, a C 1 -C 12 alkyl group, or a C 1 -C 3 alkanol; and R 6 is H, a C 1 -C 12 alkyl group, or a C 1 -C 3 alkanol; and the phenolic acid or ester has the following formula (II):

wherein Q is an alkylene group of 2 to 6 carbon atoms; R is H or a moiety suitable to undergo transesterification; R 1 and R 2 are each independently a C 1 -C 12 alkyl group.

14. The compound of claim 13 , wherein the molar ratio of boron containing compound:polyol:phenolic acid or ester is about 1:2:2.

15. The compound of claim 13 , wherein the molar ratio of boron containing compound:polyol:phenolic acid or ester is about 1:2:1.

Assignees

• Suen Yat Fan
• Mclain Julian H
• Miller John Robert
• Newell Jennifer Elizabeth
• Li Shengua
• Palekar Vivek
• Chevron Oronite Co

Inventors

• Suen Yat Fan
• Mclain Julian H
• Miller John Robert
• Newell Jennifer Elizabeth
• Li Shengua
• Palekar Vivek

Classifications

• C10M159/12

  Reaction products · CPC title

• C10M2227/062

  Cyclic esters · CPC title

• C10M2207/289

  containing free hydroxy groups · CPC title

• C10N2030/52

  Base number [TBN] · CPC title

• C10M139/00 Primary

  Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00 · CPC title