Associative and exchangeable oligomers, and composition comprising them

Patent metadata

Field	Value
Publication number	US-11312801-B2
Application number	US-201917058188-A
Country	US
Kind code	B2
Filing date	May 23, 2019
Priority date	May 24, 2018
Publication date	Apr 26, 2022
Grant date	Apr 26, 2022

Abstract

Compositions obtained by mixing at least one oligomer A1 which is obtained by the copolymerization of at least two monomers functionalized by diol functions with at least one second monomer, and at least one compound A2 comprising at least two boronic ester functions. They have rheological properties which vary significantly depending on the proportion of the compounds A1 and A2 used. Composition obtained by mixing at least one lubricating oil with such a composition of associative and exchangeable polymers, and use of this composition to lubricate a mechanical part.

First claim

The invention claimed is:

1. A composition resulting from the mixing of at least
a polydiol oligomer A1 with a number-average molar mass of greater than or equal to 600 g/mol and less than 10 000 g/mol, comprising repeating units corresponding to:
at least two monomers M1,
and
at least one monomer M2, or
at least one monomer M3, or
at least one monomer M2 and at least one monomer M3,
and the oligomer A1 comprises less than 2 mol % of repeating units corresponding to one or more monomers M3,

and
a compound A2 comprising at least two boronic ester functions,
the monomer M1 corresponding to the general formula (I):

in which:
R 1 is chosen from the group formed by —H, —CH 3 and —CH 2 —CH 3 ;
x is an integer ranging from 1 to 18
y is an integer equal to 0 or 1;
X 1 and X 2 , which may be identical or different, are chosen from the group formed by hydrogen, tetrahydropyranyl, methyloxymethyl, tert-butyl, benzyl, trimethylsilyl and t-butyldimethylsilyl;

or
X 1 and X 2 form, with the oxygen atoms, a bridge having the following formula

in which:
the asterisks (*) symbolize the bonds to oxygen atoms,
R′ 2 and R″ 2 , which may be identical or different, are chosen from the group formed by hydrogen and a C 1 -C 11 alkyl;

or
X 1 and X 2 form, with the oxygen atoms, a boronic ester having the following formula:

in which:
the asterisks (*) symbolize the bonds to oxygen atoms,
R′″ 2 is chosen from the group formed by a C 6 -C 30 aryl, a C 7 -C 30 aralkyl and a C 2 -C 30 alkyl;
the monomer M2 corresponding to the general formula (II):

in which:
R 2 is chosen from the group formed by —H, —CH 3 and —CH 2 —CH 3 ;
R 3 is chosen from the group formed by: —C(O)—O—R′ 3 ; —O—R′ 3 ; —S—R′ 3 and —C(O)—N(H)—R′ 3 with R′ 3 a C 1 -C 30 alkyl group,
the monomer M3 corresponding to the general formula (X):

in which:
Z 1 , Z 2 and Z 3 , which may be identical or different, represent groups chosen from a hydrogen atom, a C 1 -C 12 alkyl, and a group —OZ′ or —C(O)—O—Z′ with Z′ being a C 1 -C 12 alkyl.

2. The composition as claimed in claim 1 , in which the oligomer A1 has a number-average molar mass ranging from 600 g/mol to 9500 g/mol.

3. The composition as claimed in claim 1 , in which the oligomer A1 comprises less than 1.5 mol % of repeating units corresponding to one or more monomers M3 of general formula (X).

4. The composition as claimed in claim 1 , in which the monomer M3 is styrene.

5. The composition as claimed in claim 1 , in which the side chains of the oligomer A1 have a mean length ranging from 8 to 20 carbon atoms.

6. The composition as claimed in claim 1 , in which the oligomer A1 has a molar percentage of repeating units corresponding to the monomer M1 of formula (I) ranging from 2% to 70%.

7. The composition as claimed in claim 1 , in which the oligomer A1 has a number-average degree of polymerization ranging from 3 to 100.

8. The composition as claimed in claim 1 , in which the oligomer A1 has a polydispersity index (Ip) ranging from 1.05 to 4.0.

9. The composition as claimed in claim 1 , in which compound A2 is a compound of formula (III):

in which:
w 1 and w 2 , which may be identical or different, are integers chosen between 0 and 1;
R 4 , R 5 , R 6 and R 7 , which may be identical or different, represent a group chosen from a hydrogen atom, a hydrocarbon-based group comprising from 1 to 30 carbon atoms, substituted with one or more groups chosen from: a hydroxyl, a group —OJ or —C(O)—O-J with J being a hydrocarbon-based group comprising from 1 to 24 carbon atoms;
L is a divalent bonding group chosen from the group formed by a C 6 -C 18 aryl, a C 6 -C 18 aralkyl and a C 2 -C 24 hydrocarbon-based chain.

10. The composition as claimed in claim 1 , in which compound A2 is an oligomer comprising repeating units which correspond to
at least two monomers M4 of formula (IV):

in which:
t is an integer equal to 0 or 1;
u is an integer equal to 0 or 1;
M and R 8 are identical or different divalent bonding groups, chosen from the group formed by a C 6 -C 18 aryl, a C 7 -C 24 aralkyl and a C 2 -C 24 alkyl,
X is a function chosen from the group formed by —O—C(O)—, —C(O)—O—, —C(O)—N(H)—, —N(H)—C(O)—, —S—, —N(H)—, —N(R′ 4 )— and —O— with R′ 4 being a hydrocarbon-based chain comprising from 1 to 15 carbon atoms;
R 9 is chosen from the group formed by —H, —CH 3 and —CH 2 —CH 3 ;
R 10 and R 11 , which may be identical or different, represent a group chosen from a hydrogen atom, a hydrocarbon-based group comprising from 1 to 30 carbon atoms, substituted with one or more groups chosen from: a hydroxyl, a group —OJ or —C(O)—O-J with J being a hydrocarbon-based group comprising from 1 to 24 carbon atoms; and
at least one monomer M5 of general formula (V):

in which:
R 12 is chosen from the group formed by —H, —CH 3 and —CH 2 —CH 3 ,
R 13 is chosen from the group formed by —C(O)—O—R′ 13 ; —O—R′ 13 , —S—R′ 13 and —C(O)—N(H)—R′ 13 , with R′ 13 a C 1 -C 30 alkyl group,
at least one monomer M3 of general formula (X)

in which:
Z 1 , Z 2 and Z 3 , which may be identical or different, represent groups chosen from a hydrogen atom, a C 1 -C 12 alkyl, and a group —OZ′ or —C(O)—O—Z′ with Z′ being a C 1 -C 12 alkyl.

11. The composition as claimed in claim 10 , in which the oligomer A2 has a number-average molar mass ranging from 600 g/mol to less than 10 000 g/mol.

12. The composition as claimed in claim 10 , in which the oligomer A2 has a molar percentage of monomer M4 of formula (IV) in said oligomer ranging from 4% to 50%.

13. The composition as claimed in claim 10 , in which the side chains of the oligomer A2 have a mean length of greater than or equal to 8 carbon atoms.

14. The composition as claimed in claim 10 , in which the oligomer A2 has a number-average degree of polymerization ranging from 2 to 100.

15. The composition as claimed in claim 10 , in which the oligomer A2 has a polydispersity index (Ip) ranging from 1.04 to 3.54.

16. The composition as claimed in claim 1 , in which the content of oligomer A1 ranges from 0.1% to 50% by weight relative to the total weight of the composition.

17. The composition as claimed in claim 1 , in which the content of oligomer A2 ranges from 0.1% to 50% by weight relative to the total weight of the composition.

18. The composition as claimed in claim 1 , in which the mass ratio between the oligomer A1 and compound A2 (ratio A1/A2) ranges from 0.002 to 500.

19. A lubricant composition resulting from th

Assignees

• Total Marketing Services

Inventors

• Descroix Gregory
• Briand Fanny

Classifications

• C08F212/22 Primary

  Oxygen · CPC title

• C10M2205/04

  containing aromatic monomers, e.g. styrene · CPC title

• C08L43/00

  Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium or a metal; Compositions of derivatives of such polymers (of metal salts, e.g. phenolates, alcoholates, see the parent compounds) · CPC title

• C10M155/04

  Monomer containing boron · CPC title

• C10M2209/084

  Acrylate; Methacrylate · CPC title