# US 8,569,217 B2 · Lubricating composition containing a carboxylic functionalised polymer and dispersant

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- Number: US 8,569,217 B2
- Document ID: US8569217B2
- Status: Granted
- Kind: B2
- Application number: 13/202,647
- Filed: 2010-02-24
- Published: 2012-02-23
- Granted: 2013-10-29
- Earliest claimed: 2009-02-26
- Assignees: The Lubrizol Corporation
- Applicants: Matthew D. Gieselman; John K. Pudeiski; Mary Galic Raguz; Thomas Derevjanik
- Inventors: Matthew D. Gieselman; John K. Pudeiski; Mary Galic Raguz; Thomas Derevjanik
- Web page: https://patentgrep.com/patent/US8569217B2

## CPC

- C10M 161/00: Lubricating compositions characterised by the additive being a mixture of a macromolecular compound and a non-macromolecular compound, each of these compounds being essential
- C10M 133/12: having amino groups bound to a carbon atom of a six-membered aromatic ring
- C10M 133/44: Five-membered ring containing nitrogen and carbon only
- C10M 149/12: Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M 129/26: Carboxylic acids; Salts thereof
- C10M 133/16: Amides; Imides
- C10M 133/38: Heterocyclic nitrogen compounds
- C10M 149/02: Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M 159/12: Reaction products
- C10M 2205/022: Ethene
- C10M 2205/04: containing aromatic monomers, e.g. styrene
- C10M 2205/06: containing conjugated dienes
- C10M 2207/026: with tertiary alkyl groups
- C10M 2207/028: Overbased salts thereof
- C10M 2207/24: Epoxidised acids; Ester derivatives thereof
- C10M 2207/26: Overbased carboxylic acid salts
- C10M 2207/262: derived from hydroxy substituted aromatic acids, e.g. salicylates
- C10M 2207/281: of (cyclo)aliphatic monocarboxylic acids
- C10M 2207/283: of polyhydroxy compounds
- C10M 2215/064: Di- and triaryl amines
- C10M 2215/066: Arylene diamines
- C10M 2215/067: Polyaryl amine alkanes
- C10M 2215/08: Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
- C10M 2215/086: Imides [having hydrocarbon substituents containing less than thirty carbon atoms]
- C10M 2215/28: Amides; Imides
- C10M 2217/06: Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
- C10M 2219/022: of hydrocarbons, e.g. olefines
- C10M 2219/046: Overbased sulfonic acid salts
- C10M 2223/045: Metal containing thio derivatives
- C10M 2223/049: Phosphite
- C10N 2030/02: Pour-point; Viscosity index
- C10N 2030/041: {Soot induced viscosity control}
- C10N 2030/10: Inhibition of oxidation, e.g. anti-oxidants
- C10N 2030/36: {Seal compatibility, e.g. with rubber}
- 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 an oil of lubricating viscosity, a dispersant and an amine-functionalised additive, wherein the amine-functionalised additive is derived from an amine having at least 3 or 4 aromatic groups. The invention further relates to the use of the lubricating composition in an internal combustion engine.

## Claims

### Claim 1

A lubricating composition comprising an oil of lubricating viscosity, a dispersant and an amine-functionalised additive, wherein the amine-functionalised additive is derived from an amine having at least 4 aromatic groups,
wherein the amine-functionalised additive is a product obtained by reacting the amine having at least 4 aromatic groups with a carboxylic functionalised polymer,
wherein the amine having at least 4 aromatic groups is represented by the formula:
wherein independently each variable
R1 is hydrogen or a C1-5 alkyl group;
R2 is hydrogen or a C1-5 alkyl group;
U is an aliphatic, alicyclic or aromatic group, with the proviso that when U is aliphatic, the aliphatic group may be a linear or branched alkylene group containing 1 to 5 carbon atoms; and
w is 1 to 10.

### Claim 2 (depends on 1)

The lubricating composition of claim 1, wherein the amine having at least 4 aromatic groups is bis[p-(p-aminoanilino)phenyl]-methane, 2-(7-amino-acridin-3-ylmethyl)-N-4-{4-[4-(4-amino-phenylamino)-benzyl]-phenyl}-benzene-1,4-diamine, or mixtures thereof.

### Claim 3 (depends on 1)

The lubricating composition of claim 1, wherein the carboxylic functionalised polymer is a polyisobutylene succinic anhydride.

### Claim 4 (depends on 3)

The lubricating composition of claim 3, wherein the polyisobutylene succinic anhydride is derived from a polyisobutylene with number average molecular weight of 350 to 5000.

### Claim 5 (depends on 1)

The lubricating composition of claim 1, wherein the carboxylic functionalised polymer is a hydrogenated copolymer of styrene-butadiene.

### Claim 6 (depends on 1)

The lubricating composition of claim 1, wherein the carboxylic functionalised polymer is ethylene-propylene copolymer grafted with maleic anhydride.

### Claim 7 (depends on 1)

The lubricating composition of claim 1, wherein the carboxylic functionalised polymer is a hydrogenated styrene-isoprene polymer.

### Claim 8 (depends on 1)

The lubricating composition of claim 1, wherein the dispersant is a succinimide dispersant.

### Claim 9 (depends on 8)

The lubricating composition of claim 8, wherein the succinimide dispersant is derived from an aliphatic polyamine, or mixtures thereof.

### Claim 10 (depends on 9)

The lubricating composition of claim 9, wherein the aliphatic polyamine is an ethylenepolyamine, a propylenepolyamine, a butylenepolyamine, or mixtures thereof.

### Claim 11 (depends on 9)

The lubricating composition of claim 9, wherein the aliphatic polyamine is selected from the group consisting of ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, polyamine still bottoms, and mixtures thereof.

### Claim 12 (depends on 1)

The lubricating composition of claim 1, wherein the lubricating composition is characterised as having (i) a sulphur content of 0.5 wt % or less, (ii) a phosphorus content of 0.1 wt % or less, and (iii) a sulphated ash content of 1.5 wt % or less.

### Claim 13 (depends on 1)

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

### Claim 14 (depends on 1)

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

### Claim 15 (depends on 14)

The lubricating composition of claim 14, wherein the dispersant viscosity modifier is prepared by grafting of an olefinic carboxylic acid acylating agent onto a polymer of 15 to 80 mole percent of ethylene, from 20 to 85 mole percent of C3-10 alpha monoolefin, and from 0 to 15 mole percent of non-conjugated diene or triene, said polymer having an average molecular weight ranging from 5000 to 500,000, and further reacting said grafted polymer with an amine.

### Claim 16 (depends on 14)

The lubricating composition of claim 14, wherein the dispersant viscosity modifier is a reaction product of: (a) a polymer comprising carboxylic acid functionality or a reactive equivalent thereof, said polymer having a number average molecular weight of greater than 5,000; and (b) an amine component comprising at least one aromatic amine containing at least one amino group capable of condensing with said carboxylic acid functionality to provide a pendant group and at least one additional group comprising at least one nitrogen, oxygen, or sulfur atom, wherein said aromatic amine is selected from the group consisting of (i) a nitro-substituted aniline, (ii) an amine comprising two aromatic moieties linked by a —C(O)NR— group, a —C(O)O— group, an —O— group, an —N═N— group, or an —SO2— group where R is hydrogen or hydrocarbyl, one of said aromatic moieties bearing said condensable amino group, (iii) an aminoquinoline, (iv) an aminobenzimidazole, (v) an N,N-dialkylphenylenediamine, and (vi) a ring-substituted benzylamine.

### Claim 17 (depends on 1)

A method of lubricating an internal combustion engine comprising supplying to the internal combustion engine the lubricating composition of claim 1.

### Claim 18

A lubricating composition comprising an oil of lubricating viscosity, a dispersant and an amine-functionalised additive, wherein the amine-functionalised additive is derived from an amine having at least 3 aromatic groups,
wherein the amine-functionalised additive is a product obtained/obtainable by reacting the amine having at least 3 aromatic groups with a carboxylic functionalised polymer, wherein the amine-functionalised additive is derived from an amine having at least 3 aromatic groups obtained/obtainable by a process comprising reacting: (1) isatoic anhydride or alkyl substituted isatoic anhydride and (2) an aromatic amine with at least two aromatic groups and a primary or a reactive secondary amino group.

### Claim 19 (depends on 18)

The lubricating composition of claim 18, wherein the carboxylic functionalised polymer is a polyisobutylene succinic anhydride.

### Claim 20 (depends on 18)

The lubricating composition of claim 18, wherein the polyisobutylene succinic anhydride is derived from a polyisobutylene with number average molecular weight of 350 to 5000.

### Claim 21 (depends on 18)

The lubricating composition of claim 18, wherein the carboxylic functionalised polymer is a hydrogenated copolymer of styrene-butadiene.

### Claim 22 (depends on 18)

The lubricating composition of claim 18, wherein the carboxylic functionalised polymer is ethylene-propylene copolymer grafted with maleic anhydride.

### Claim 23 (depends on 18)

The lubricating composition of claim 18, wherein the carboxylic functionalised polymer is a hydrogenated styrene-isoprene polymer.

### Claim 24 (depends on 18)

The lubricating composition of claim 18, wherein the dispersant is a succinimide dispersant.

### Claim 25 (depends on 24)

The lubricating composition of claim 24, wherein the succinimide dispersant is derived from an aliphatic polyamine, or mixtures thereof.

### Claim 26 (depends on 25)

The lubricating composition of claim 25, wherein the aliphatic polyamine is an ethylenepolyamine, a propylenepolyamine, a butylenepolyamine, or mixtures thereof.

### Claim 27 (depends on 25)

The lubricating composition of claim 25, wherein the aliphatic polyamine is selected from the group consisting of ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, polyamine still bottoms, and mixtures thereof.

### Claim 28 (depends on 18)

The lubricating composition of claim 18, wherein the lubricating composition is characterised as having (i) a sulphur content of 0.5 wt % or less, (ii) a phosphorus content of 0.1 wt % or less, and (iii) a sulphated ash content of 1.5 wt % or less.

### Claim 29 (depends on 18)

The lubricating composition of claim 18 further comprising at least one of an antiwear agent, a dispersant viscosity modifier, a friction modifier, a viscosity modifier, an antioxidant, an overbased detergent, or mixtures thereof.

### Claim 30 (depends on 18)

The lubricating composition of claim 18 further comprising a dispersant viscosity modifier.

### Claim 31 (depends on 30)

The lubricating composition of claim 30, wherein the dispersant viscosity modifier is prepared by grafting of an olefinic carboxylic acid acylating agent onto a polymer of 15 to 80 mole percent of ethylene, from 20 to 85 mole percent of C3-10 alpha monoolefin, and from 0 to 15 mole percent of non-conjugated diene or triene, said polymer having an average molecular weight ranging from 5000 to 500,000, and further reacting said grafted polymer with an amine.

### Claim 32 (depends on 30)

The lubricating composition of claim 30, wherein the dispersant viscosity modifier is a reaction product of: (a) a polymer comprising carboxylic acid functionality or a reactive equivalent thereof, said polymer having a number average molecular weight of greater than 5,000; and (b) an amine component comprising at least one aromatic amine containing at least one amino group capable of condensing with said carboxylic acid functionality to provide a pendant group and at least one additional group comprising at least one nitrogen, oxygen, or sulfur atom, wherein said aromatic amine is selected from the group consisting of (i) a nitro-substituted aniline, (ii) an amine comprising two aromatic moieties linked by a —C(O)NR— group, a —C(O)O— group, an —O— group, an —N═N— group, or an —SO2— group where R is hydrogen or hydrocarbyl, one of said aromatic moieties bearing said condensable amino group, (iii) an aminoquinoline, (iv) an aminobenzimidazole, (v) an N,N-dialkylphenylenediamine, and (vi) a ring-substituted benzylamine.

### Claim 33 (depends on 18)

A method of lubricating an internal combustion engine comprising supplying to the internal combustion engine the lubricating composition of claim 18.