# US 9,752,093 B2 · Borated polyol ester of hindered phenol antioxidant/friction modifier with enhanced performance

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- Number: US 9,752,093 B2
- Document ID: US9752093B2
- Status: Granted
- Kind: B2
- Application number: 14/730,587
- Filed: 2015-06-04
- Published: 2016-12-08
- Granted: 2017-09-05
- Earliest claimed: 2015-06-04
- Assignees: Chevron Oronite Company LLC
- Applicants: Yat Fan Suen; Julian H. McLain; John Robert Miller; Jennifer Elizabeth Newell; Shengua Li; Vivek Palekar
- Inventors: Yat Fan Suen; Julian H. McLain; John Robert Miller; Jennifer Elizabeth Newell; Shengua Li; Vivek Palekar
- Web page: https://patentgrep.com/patent/US9752093B2

## CPC

- C10M 139/00: 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
- C07F 5/025: {Boronic and borinic acid compounds}
- C10M 159/12: Reaction products
- C10M 2207/023: having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M 2207/026: with tertiary alkyl groups
- C10M 2207/281: of (cyclo)aliphatic monocarboxylic acids
- C10M 2207/283: of polyhydroxy compounds
- C10M 2207/289: containing free hydroxy groups
- C10M 2227/061: Esters derived from boron
- C10M 2227/062: Cyclic esters
- C10N 2030/06: Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
- C10N 2030/10: Inhibition of oxidation, e.g. anti-oxidants
- C10N 2030/12: Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
- C10N 2030/52: {Base number [TBN]}
- C10N 2030/54: {Fuel economy}
- C10N 2040/04: Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N 2040/08: Hydraulic fluids, e.g. brake-fluids
- C10N 2040/25: Internal-combustion engines
- C10N 2040/252: {Diesel engines}
- C10N 2070/00: Specific manufacturing methods for lubricant compositions
- C10N 2070/02: {Concentrating of additives}
- C10M: LUBRICATING COMPOSITIONS (well drilling compositions C09K8/02); USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION (mould release, i.e. separating, agents for metals B22C3/00, for plastics or substances in a plastic state, in general B29C33/56, for glass C03B40/02; textile lubricating compositions D06M11/00, D06M13/00, D06M15/00; immersion oils for microscopy G02B21/33)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C10N: INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS

## 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.

## Claims

### Claim 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; R1 and R2 are each independently a C1-C12 alkyl group; R5 is H, a C1-C12 alkyl group, or a C1-C3 alkanol; and R6 is H, a C1-C12 alkyl group, or a C1-C3 alkanol;
b. a boron containing compound; and
c. optionally, an alcohol.

### Claim 2 (depends on 1)

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.

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 1)

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

### Claim 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; R1 and R2 are each independently a C1-C12 alkyl group; R3 is absent or a C1-C12 alkoxy group; R4 is absent or a C1-C12 alkoxy group; R5 is H, a C1-C12 alkyl group, or a C1-C3 alkanol; and R6 is H, a C1-C12 alkyl group, or a C1-C3 alkanol.

### Claim 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; R1 and R2 are each independently a C1-C12 alkyl group; R5 is H, a C1-C12 alkyl group, or a C1-C3 alkanol; and R6 is H, a C1-C12 alkyl group, or a C1-C3 alkanol.

### Claim 7 (depends on 5)

The compound of claim 5, wherein the compound has the following formula (VI):
wherein R1, R2, R3, R4, R5, m, p, and q are as defined in claim 5.

### Claim 8 (depends on 5)

The compound of claim 5, wherein the compound has the following formula (VII):
wherein R1, R2, R3, R4, and R5 are as defined in claim 5.

### Claim 9 (depends on 5)

The compound of claim 5, wherein the compound has the following structure (VIII):
wherein R1, R2, R3, and R5 are as defined in claim 5.

### Claim 10 (depends on 6)

The compound of claim 6, wherein the compound has the structure of formula (IX):
wherein R1, R2, and R5 are as defined in claim 6.

### Claim 11 (depends on 5)

The compound of claim 5, wherein R1 and R2 are both t-butyl groups.

### Claim 12 (depends on 6)

The compound of claim 6, wherein R1 and R2 are both t-butyl groups.

### Claim 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; R5 is H, a C1-C12 alkyl group, or a C1-C3 alkanol; and R6 is H, a C1-C12 alkyl group, or a C1-C3 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; R1 and R2 are each independently a C1-C12 alkyl group.

### Claim 14 (depends on 13)

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

### Claim 15 (depends on 13)

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