# US 11,111,451 B2 · Mercaptoazole derivatives as lubricating additives

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- Number: US 11,111,451 B2
- Document ID: US11111451B2
- Status: Granted
- Kind: B2
- Application number: 16/091,705
- Filed: 2017-03-30
- Published: 2019-05-23
- Granted: 2021-09-07
- Earliest claimed: 2016-04-07
- Assignees: The Lubrizol Corporation
- Applicants: The Lubrizol Corporation
- Inventors: Yanshi Zhang; Nga H. Nguyen
- Web page: https://patentgrep.com/patent/US11111451B2

## CPC

- C10M 135/36: the ring containing sulfur and carbon with nitrogen or oxygen
- C10M 135/32: Heterocyclic sulfur, selenium or tellurium compounds
- C10M 141/08: at least one of them being an organic sulfur-, selenium- or tellurium-containing compound
- C10M 2201/087: Boron oxides, acids or salts
- C10M 2203/1025: used as base material
- C10M 2207/026: with tertiary alkyl groups
- C10M 2215/00: Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M 2215/064: Di- and triaryl amines
- C10M 2215/28: Amides; Imides
- C10M 2219/022: of hydrocarbons, e.g. olefines
- C10M 2219/046: Overbased sulfonic acid salts
- C10M 2219/089: Overbased salts
- C10M 2219/104: containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M 2223/00: Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M 2223/045: Metal containing thio derivatives
- C10M 2227/061: Esters derived from boron
- C10M 2227/062: Cyclic esters
- C10N 2010/04: Groups 2 or 12
- C10N 2020/04: Molecular weight; Molecular weight distribution
- 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 2030/12: Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
- C10N 2030/36: {Seal compatibility, e.g. with rubber}
- C10N 2040/25: Internal-combustion engines
- C10N 2060/14: by boron or a compound containing boron
- 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

Lubricating compositions comprising a mercaptoazole-acrylic adduct formed by contacting a mercaptoazole compound with an acrylic. The adduct formed has at least one sulfur-alkyl group comprising at least one acyl, or compounds having at least one nitrogen-alkyl group comprising at least one acyl, or mixtures thereof. The lubricating composition also comprises an antiwear agent and an antioxidant. Methods of lubricating an internal combustion engine comprising contacting the internal combustion engine with the lubricating composition comprising a mercaptoazole-acrylic adduct formed by contacting a mercaptoazole compound with an acrylic. Methods of reducing corrosion and/or seal deterioration in an internal combustion engine. The use of a mercaptoazole-acrylic adduct in a lubricating composition to reduce corrosion and/or seal deterioration in an internal combustion engine.

## Claims

### Claim 1

A method of reducing copper corrosion in an internal combustion engine comprising contacting the internal combustion engine with a lubricating composition comprising:
a. an oil of a lubricating viscosity;
b. 0.01 wt % to 5 wt % of a mercaptoazole-acrylic adduct having the formula (IV) or (V):
wherein R6 is hydrogen or a C1-C20 hydrocarbyl group; R7 is a linear or branched hydrocarbyl group having at least two carbon atoms; and R8 is a C1-C20 hydrocarbyl group and is linear, branched, homocyclic, heterocyclic, or a combination thereof and wherein the hydrocarbyl groups have no non-hydrocarbon substituents;
c. an antiwear agent containing phosphorus and present in an amount such that said lubricating composition has at least 300 ppm phosphorus based on a total weight of said lubricating composition; and
d. an antioxidant.

### Claim 2 (depends on 1)

The method of claim 1, wherein said mercaptoazole-acrylic adduct has the formula (VI) or (VII):
wherein R6 is hydrogen or a C1-C20 hydrocarbyl group, and R8 is a C1-C20 hydrocarbyl group and is linear, branched, homocyclic, heterocyclic, or a combination thereof.

### Claim 3 (depends on 1)

The method of claim 1, wherein said mercaptoazole-acrylic adduct has the formula (VIII):
wherein R6 is hydrogen or a C1-C20 hydrocarbyl group.

### Claim 4 (depends on 1)

The method of claim 1, further comprising at least one boron-containing compound.

### Claim 5 (depends on 1)

The method of claim 1, further comprising at least one overbased detergent.

### Claim 6 (depends on 1)

A method of claim 1, wherein lead corrosion and/or seal deterioration is also reduced.