# US 2014/0194330 A1 · Lubricating Composition Containing an Ester of an Aromatic Carboxylic Acid

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- Number: US 2014/0194330 A1
- Document ID: US20140194330A1
- Status: Published application
- Kind: A1
- Application number: 14/117,462
- Filed: 2012-06-13
- Published: 2014-07-10
- Earliest claimed: 2011-06-15
- Assignees: The Lubrizol Corporation
- Applicants: The Lubrizol Corporation
- Inventors: Scott Capitosti; Seth L. Crawley; Ewan E. Delbridge; Patrick E. Mosier
- Web page: https://patentgrep.com/patent/US20140194330A1

## CPC

- C10M 141/10: at least one of them being an organic phosphorus-containing compound
- C10M 129/76: containing free hydroxy or carboxyl groups
- C10M 2203/1025: used as base material
- C10M 2205/022: Ethene
- C10M 2207/284: of aromatic monocarboxylic acids
- C10M 2207/289: containing free hydroxy groups
- C10M 2215/064: Di- and triaryl amines
- C10M 2215/086: Imides [having hydrocarbon substituents containing less than thirty carbon atoms]
- C10M 2219/046: Overbased sulfonic acid salts
- C10M 2223/045: Metal containing thio derivatives
- C10N 2030/06: Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
- C10N 2030/10: Inhibition of oxidation, e.g. anti-oxidants
- C10N 2030/42: {Phosphor free or low phosphor content compositions}
- C10N 2030/43: {Sulfur free or low sulfur content compositions}
- C10N 2030/45: {Ash-less or low ash content}
- C10N 2040/25: Internal-combustion engines
- 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)
- C10N: INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS

## Abstract

The invention provides a lubricating composition containing an oil of lubricating viscosity and an ester, thioester, amide or imide of a carboxylic acid compound where said carboxylic acid is characterized in that it is functionalized with a hydroxy-substituted aromatic moiety. The invention further relates to methods of lubricating an internal combustion engine by supplying the described lubricating composition to the internal combustion engine. The invention further relates to the use of the salt of the carboxylic acid compound as an antiwear agent or an antioxidant.

## Claims

### Claim 1

A lubricating composition comprising an oil of lubricating viscosity and an additive comprising an ester, thioester, amide, or imide of a carboxylic acid or any combination thereof wherein the carbonyl carbon of the acid is attached directly or through a divalent hydrocarbyl linkage to an aromatic moiety wherein said aromatic moiety includes two or more hydroxy-groups, alkoxy-groups, or mixtures thereof, with the proviso that if said aromatic moiety consists of a single ring, then no two hydroxy-groups, alkoxy-groups, or mixtures thereof are located on adjacent carbon atoms of said aromatic ring.

### Claim 2 (depends on 1)

The lubricating composition of claim 1 wherein the additive comprises an ester, thioester, amide, or imide of a carboxylic acid, or any combination thereof, wherein the carbonyl carbon of the acid is attached directly to or through a hydrocarbyl linkage to an aromatic moiety wherein said aromatic moiety consists of a single aromatic ring and includes two or more hydroxy-groups, alkoxy-groups, or mixtures thereof;
wherein no two of said hydroxy-groups, alkoxy-groups, or mixtures thereof are located on adjacent carbon atoms of said aromatic ring.

### Claim 3 (depends on 1)

The lubricating composition of claim 1 wherein the additive comprises an ester, thioester, amide, or imide of a carboxylic acid, or any combination thereof, wherein the carbonyl carbon of the acid is attached directly to or through a divalent hydrocarbyl linkage to an aromatic moiety wherein said aromatic moiety consists of at least two aromatic rings and includes two or more hydroxy-groups, alkoxy-groups, or mixtures thereof.

### Claim 4 (depends on 1)

The lubricating composition of claim 1 wherein the (thio)ester, amide, or imide of a carboxylic acid, or any combination thereof, comprises a compound of Formula (1):
wherein a is an integer from 2 to 4;
R1 is —C(O)XR5, or —R4—C(O) XR5, where X is —O—, —S—, —NR6—, or combinations thereof, R4 is a divalent hydrocarbyl group of 1 to 10 carbon atoms, R5 is a linear or branched hydrocarbyl group containing 1 to 30 carbon atoms, R6 is hydrogen or a hydrocarbyl group of 1 to 30 carbon atoms;
each R2 is independently hydrogen, linear or branched hydrocarbyl groups containing 1 to 10 carbon atoms, or mixtures thereof; and
R3 is hydrogen or a hydrocarbyl group containing 1 to 30 carbon atoms;
With the proviso that no two —(OR2) groups are attached to adjacent carbon atoms of the aromatic ring.

### Claim 5 (depends on 1)

The lubricating composition of claim 1, wherein the (thio)ester, amide, or imide of a carboxylic acid has the Formula (3):
Where X is —O—, —S—, or —NR8, or combinations thereof; R3 is hydrogen or a hydrocarbyl group containing 1 to 30 carbon atoms, R7 is a linear or branched hydrocarbyl group containing 1 to 30 carbon atoms, and R8 is hydrogen or a hydrocarbyl group of 1 to 30 carbon atoms.

### Claim 6 (depends on 1)

The lubricating composition of claim 1, wherein the (thio)ester, amide, or imide of a carboxylic acid has the Formula (4):
where a is 0 to 2, b is 0 to 2, and a+b is 2 to 4; each R2 is independently hydrogen, linear or branched hydrocarbyl groups containing 1 to 10 carbon atoms, or mixtures thereof X is —O—, —S—, or —NR8, or combinations thereof; R3 is hydrogen or a hydrocarbyl group containing 1 to 30 carbon atoms, R7 is a linear or branched hydrocarbyl group containing 1 to 30 carbon atoms, and R8 is hydrogen or a hydrocarbyl group of 1 to 30 carbon atoms.

### Claim 7 (depends on 1)

The lubricating composition of claim 1 wherein each R2 is hydrogen.

### Claim 8 (depends on 1)

The lubricating composition of claim 1 wherein said ester, amide, or imide of a carboxylic acid, or any combination thereof, is derived from 2,5-dihydroxybenzoic acid, 1,4-dihydroxy-2-naphthoic acid, 3,5-dihydroxynaphthoic acid, 3,7-dihydroxynaphthoic acid, reactive equivalents, or mixtures thereof.

### Claim 9 (depends on 1)

The lubricating composition of claim 1 wherein said ester, amide, or imide of a carboxylic acid, or any combination thereof, is present in a range of 0.01 wt % to 10 wt % of the lubricating composition.

### Claim 10 (depends on 1)

The lubricating composition of claim 1 wherein the lubricating composition is characterized as having (i) a sulfur content of 0.5 wt % or less, (ii) a phosphorus content of 0.1 wt % or less, (iii) a sulfated ash content of 1.5 wt % or less, or any combination thereof.

### Claim 11 (depends on 1)

The lubricating composition of claim 1 further comprising an antiwear agent, a dispersant viscosity modifier, a friction modifier, a viscosity modifier, an antioxidant, an overbased detergent, or mixtures thereof.

### Claim 12 (depends on 1)

The lubricating composition of claim 1 further comprising a metal dihydrocarbyl dithiophosphate that contributes at least 100 ppm of phosphorus to the overall composition.

### Claim 13 (depends on 12)

The lubricating composition of claim 12, wherein the friction modifier is selected from the group consisting of long chain fatty acid derivatives of amines, long chain fatty esters, long chain fatty epoxides, fatty imidazolines, amine salts of alkylphosphoric acids, fatty alkyl tartrates, fatty alkyl tartrimides, fatty alkyl tartramides, and combinations thereof.

### Claim 14 (depends on 1)

The lubricating composition of claim 1 further comprising a dispersant viscosity modifier.

### Claim 15

(canceled)

### Claim 16 (depends on 1)

A method of lubricating an internal combustion engine comprising the step of: (I) supplying to the internal combustion engine the lubricating composition of claim 1.

### Claim 17

(canceled)