# US 11,028,333 B2 · Lubricating oil additives

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- Number: US 11,028,333 B2
- Document ID: US11028333B2
- Status: Granted
- Kind: B2
- Application number: 16/745,522
- Filed: 2020-01-17
- Published: 2020-05-14
- Granted: 2021-06-08
- Earliest claimed: 2017-11-13
- Assignees: Infineum International Limited
- Applicants: Infineum International Limited
- Inventors: Peter J. Dowding; Elin J. Eis
- Web page: https://patentgrep.com/patent/US11028333B2

## CPC

- C10M 129/42: polycarboxylic
- C10M 133/16: Amides; Imides
- C10M 135/10: Sulfonic acids or derivatives thereof
- C10M 159/20: Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
- C10M 2207/26: Overbased carboxylic acid salts
- C10M 2215/08: Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
- C10M 2215/28: Amides; Imides
- C10M 2219/044: Sulfonic acids, Derivatives thereof, e.g. neutral salts
- C10M 2219/046: Overbased sulfonic acid salts
- C10N 2010/02: Groups 1 or 11
- C10N 2010/04: Groups 2 or 12
- C10N 2030/04: Detergent property or dispersant property
- C10N 2030/06: Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
- C10N 2030/10: Inhibition of oxidation, e.g. anti-oxidants
- C10N 2030/52: {Base number [TBN]}
- 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

A metal-containing detergent, suitable for use as a lubricant additive, in the form of a concentrate in oil in which a basic metal-containing material is maintained in dispersion or solution in the oil by a gemini surfactant system comprising, or being derivable or derived from, a double bond-unsaturated carboxylic acid having 8 to 30 carbon atoms, the double bond or bonds of which being functionalized to carry polar groups across or on the double bond or bonds and the carboxylic acid group or groups thereof being functionalized to become an amide or ester group carrying at least one alkyl group having 4 to 20 carbon atoms.

## Claims

### Claim 1

A crankcase lubricating oil composition comprising:
a major amount of an oil of lubricating viscosity; and
a minor amount of a metal-containing detergent, in the form of a concentrate in oil as a dispersion or a solution, comprising a gemini surfactant system derived from a C8-C30 double bond-unsaturated carboxylic acid, which double bond has been functionalized to form at least one polar group and which carboxylic acid has been functionalized to form an amide or ester group having at least one C4-C20 alkyl group.

### Claim 2 (depends on 1)

The composition of claim 1, further comprising minor amounts of one or more other additives, different from said detergent, which additives are ashless dispersants, metal detergents, corrosion inhibitors, antioxidants, pour point depressants, antiwear agents, friction modifiers, demulsifiers, antifoamants, viscosity modifiers, and combinations thereof.

### Claim 3

A method of improved friction reduction performance of a crankcase lubricating oil composition, which method comprises formulating the composition to contain a minor amount of a metal-containing detergent, in the form of a concentrate in oil as a dispersion or a solution, comprising a gemini surfactant system derived from a C8-C30 double bond-unsaturated carboxylic acid, which double bond has been functionalized to form at least one polar group and which carboxylic acid has been functionalized to form an amide or ester group having at least one C4-C20 alkyl group.

### Claim 4 (depends on 1)

A method of lubricating surfaces in the crankcase of an internal combustion engine during its operation, the method comprising:
(i) providing a crankcase lubricating oil composition according to claim 1;
(ii) providing the composition to the crankcase of an internal combustion engine;
(iii) providing a hydrocarbon fuel in a combustion chamber of the engine; and
(iv) combusting the fuel in the combustion chamber.

### Claim 5 (depends on 1)

The composition of claim 1, wherein the C8-C30 unsaturated carboxylic acid of the gemini surfactant system had only one double bond.

### Claim 6 (depends on 1)

The composition of claim 1, wherein the at least one polar group of the gemini surfactant system is a sulfonate and/or a hydroxyl group.

### Claim 7 (depends on 5)

The composition of claim 5, wherein the at least one polar group of the gemini surfactant system is a sulfonate and/or a hydroxyl group.

### Claim 8 (depends on 1)

The composition of claim 1, wherein the gemini surfactant system is sulfur-free or substantially sulfur-free.

### Claim 9 (depends on 1)

The composition of claim 1, wherein the detergent metal is a Group 1 or Group 2 metal.

### Claim 10 (depends on 9)

The composition of claim 9, wherein the metal comprises calcium.

### Claim 11 (depends on 1)

The composition of claim 1, wherein the detergent comprises an overbased detergent.

### Claim 12 (depends on 1)

The composition of claim 1, wherein the detergent comprises a neutral detergent.

### Claim 13 (depends on 1)

The composition of claim 1, wherein the gemini surfactant system comprises a 4,4′-(1-(dialkylamino)-1-oxooctadecane-9,10-diyl)bis(oxy)-(4-oxobutanoate)) anion, and wherein each alkyl group in the dialkylamino moiety comprises from 4 to 20 carbon atoms.

### Claim 14 (depends on 1)

The composition of claim 1, where the double bond-unsaturated carboxylic acid of the gemini surfactant system was a C12-C30 acid.

### Claim 15 (depends on 5)

The composition of claim 5, wherein the double bond-unsaturated carboxylic acid of the gemini surfactant system was derived from oleic acid.