Compound comprising polyamine, acidic and boron functionalities and its use as a lubricant additive

Patent metadata

Field	Value
Publication number	US-11111452-B2
Application number	US-201816613531-A
Country	US
Kind code	B2
Filing date	May 30, 2018
Priority date	May 31, 2017
Publication date	Sep 7, 2021
Grant date	Sep 7, 2021

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.

First claim

The invention claimed is:

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.

2. 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.

3. 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.

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

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

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

7. 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 C 1 -C 12 alkyl boronic acid, a C 1 -C 12 dialkyl boric acid, a C 6 -C 12 aryl boric acid, a C 6 -C 12 diaryl boric acid, a C 7 -C 12 aralkyl boric acid, a C 7 -C 12 diaralkyl boric acid, and products deriving from these by substitution of an alkyl group by one or more alkoxy unit.

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

9. 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.

10. 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).

11. 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.

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

13. 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.

14. 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.

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

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

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

18. 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.

19. 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 .

20. 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 .

Assignees

• Total Marketing Services

Inventors

• Rogues De Fursac Isabelle
• Doyen Valérie

Classifications

• C10N2030/52

  Base number [TBN] · CPC title

• C10M159/12 Primary

  Reaction products · CPC title

• C10M2207/144

  containing hydroxy groups · CPC title

• C10M169/041

  the additives being macromolecular compounds only · CPC title

• C10N2040/252

  Diesel engines · CPC title