# US 11,111,452 B2 · Compound comprising polyamine, acidic and boron functionalities and its use as a lubricant additive

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- Number: US 11,111,452 B2
- Document ID: US11111452B2
- Status: Granted
- Kind: B2
- Application number: 16/613,531
- Filed: 2018-05-30
- Published: 2020-03-05
- Granted: 2021-09-07
- Earliest claimed: 2017-05-31
- Assignees: Total Marketing Services
- Applicants: Total Marketing Services
- Inventors: Isabelle Rogues De Fursac; Valérie Doyen
- Web page: https://patentgrep.com/patent/US11111452B2

## CPC

- C10M 159/12: Reaction products
- C08G 73/0206: {Polyalkylene(poly)amines}
- C10M 169/041: {the additives being macromolecular compounds only}
- C10M 2203/003: used as base material
- C10M 2207/144: containing hydroxy groups
- C10M 2215/04: having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M 2215/042: containing hydroxy groups; Alkoxylated derivatives thereof
- C10M 2229/00: Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10N 2030/04: Detergent property or dispersant property
- C10N 2030/52: {Base number [TBN]}
- C10N 2040/252: {Diesel 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)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C10N: INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS

## Abstract

A product resulting from the reaction of at least: a hydroxybenzoic acid, optionally substituted by a hydrocarbyl group, a boron compound, an amine component selected from a di-fatty-alkyl(ene) polyalkylamine composition including one or more polyalkylamines of formulae (I) or (II). A lubricant composition includes this product. Use of this product as a lubricant for two-stroke marine engines and four-stroke marine engines, more preferably two-stroke marine engines.

## Claims

### Claim 1

A product resulting from the reaction of at least:
a hydroxybenzoic acid, optionally substituted by a hydrocarbyl group,
a boron compound,
an amine component selected from a di-fatty-alkyl(ene) polyalkylamine composition comprising one or more polyalkylamines of formulae (I) or (II):
wherein,
each R is, independent of the other R, an alkyl moiety or an alkylene moiety with 4 to 30 carbon atoms, which is linear or branched,
n and z are independent of each other either 0, 1, 2, or 3, and
when z is greater-than 0 then o and p are independent of each other either 0, 1, 2, or 3,
or derivatives thereof selected from products wherein one or more of the NH moieties of the dialkyl polyalkylamines are methylated, alkoxylated, or both,
whereby said polyalkylamine composition comprises at least 3% by weight of branched compounds of formula (I) or (II), with regards to the total weight of polyalkylamine compounds (I) and (II) in the composition, branched compound signifying that:
in formula (I) at least one of n and z are greater than or equal to 1,
in formula (II) n is greater than or equal to 1.

### Claim 2 (depends on 1)

The product according to claim 1, wherein the hydroxybenzoic acid, optionally substituted by a hydrocarbyl group, is selected from the group consisting of: mono-alk(en)yl substituted salicylic acids, di-alk(en)yl substituted salicylic acids, acid functionalized calixarenes and mixtures thereof.

### Claim 3 (depends on 1)

The product according to claim 1, wherein the hydroxybenzoic acid compound, optionally substituted by a hydrocarbyl group, corresponds to formula (III):
Wherein:
X represents a hydrocarbyl with 1 to 50 carbon atoms, and X can comprise one or more heteroatoms,
a is an integer, a represents 0, 1 or 2.

### Claim 4 (depends on 3)

The product according to claim 3, wherein X comprises from 12 to 40 carbon atoms.

### Claim 5 (depends on 3)

The product according to claim 3, wherein the hydroxybenzoic acid compound, optionally substituted by a hydrocarbyl group, corresponds to formula (IIIA):

### Claim 6 (depends on 5)

The product according to claim 5, wherein the hydroxybenzoic acid compound is salicylic acid.

### Claim 7 (depends on 1)

The product according to claim 1, wherein the boron compound is selected from the group consisting of: boric acid, boric acid complexes, boric oxide, a trialkyl borate in which the alkyl groups comprise independently from 1 to 4 carbon atoms, a C1-C12 alkyl boronic acid, a C1-C12 dialkyl boric acid, a C6-C12 aryl boric acid, a C6-C12 diaryl boric acid, a C7-C12 aralkyl boric acid, a C7-C12 diaralkyl boric acid, and products deriving from these by substitution of an alkyl group by one or more alkoxy unit.

### Claim 8 (depends on 7)

The product according to claim 7, wherein the boron compound is boric acid.

### Claim 9 (depends on 1)

The product according to claim 1, wherein the polyalkylamine composition comprises at least 4% w/w of branched compounds of formula (I) or (II), with regards to the total weight of polyalkylamine compounds (I) and (II) in the composition, branched compound signifying that:
in formula (I), at least one of n or z are greater than or equal to 1,
in formula (II), n is greater than or equal to 1.

### Claim 10 (depends on 1)

The product according to claim 1, wherein the polyalkylamine composition comprises at least 5% by weight, with regards to the total weight of compounds (I) and (II), of products of formulae (I) and (II) with a linear structure, linear meaning n is 0 in formulae (I) and (II) and z is 0 in formula (I).

### Claim 11 (depends on 1)

The product according to claim 1, wherein the polyalkylamine composition further comprises derivatives of polyalkylamines of formula (I) or (II), said derivatives are alkoxylates which are optionally methylated.

### Claim 12 (depends on 1)

The product according to claim 1, wherein the polyalkylamine composition further comprises derivatives of polyalkylamines of formula (I) or (II), said derivatives are methylated.

### Claim 13 (depends on 1)

The product according to claim 1, wherein each R is, independent of the other R, a linear or branched alkyl group or alkenyl group comprising 8 to 22 carbon atoms.

### Claim 14 (depends on 13)

The product according to claim 13, wherein each R is, independent of the other R, a linear or branched alkyl group or alkenyl group comprising 14 to 18 carbon atoms.

### Claim 15 (depends on 13)

The product according to claim 13, wherein R groups are derived from animal and vegetal oils and fats and mixtures thereof.

### Claim 16 (depends on 15)

The product according to claim 15, wherein R groups are derived from tallow oil.

### Claim 17 (depends on 1)

A lubricant composition comprising at least one product according to claim 1 and at least one base oil.

### Claim 18 (depends on 17)

A lubricant composition according to claim 17 comprising:
from 60 to 99.9% of the at least one base oil,
from 0.1 to 20% of the at least one product.

### Claim 19 (depends on 1)

Method for lubricating two-stroke marine engines and four-stroke marine engines comprising application to said marine engines of a product according to claim 1.

### Claim 20 (depends on 17)

Method for lubricating two-stroke marine engines and four-stroke marine engines comprising application to said marine engines of a lubricant composition according to claim 17.