Associative and exchangeable oligomers, and composition comprising same

Patent metadata

Field	Value
Publication number	US-11377618-B2
Application number	US-201917058392-A
Country	US
Kind code	B2
Filing date	May 23, 2019
Priority date	May 24, 2018
Publication date	Jul 5, 2022
Grant date	Jul 5, 2022

Abstract

Compositions resulting from the mixing of at least one oligomer A1, resulting from the copolymerization of at least one monomer functionalized by diol functions with at least a second monomer, and at least one compound A2 including at least two boronic ester functions. The compositions exhibit very varied rheological properties, depending on the proportion of the compounds A1 and A2 used. A composition also results from mixing at least one lubricating oil with such a composition of associative and exchangeable polymers, and to the 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 5000 g/mol, comprising repeating units corresponding to:
at least two monomers M1, and
from 2 mol % to 50 mol % of repeating units corresponding to one or more monomers M3, and
optionally at least one monomer M2, 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 4900 g/mol.

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

4. 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.

5. 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%.

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

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

8. 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, optionally 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.

9. 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, optionally 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
optionally 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,
optionally 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.

10. The composition as claimed in claim 9 , in which the oligomer A2 has a number-average molar mass ranging from 600 g/mol to less than 10 000 g/mol.

11. The composition as claimed in claim 9 , in which the oligomer A2 has a molar percentage of monomer M4 of formula (IV) in said oligomer ranging from 4% to 50%.

12. The composition as claimed in claim 9 , in which, the chain formed by the sequence of groups R 10 , M, X and (R 8 ) u with u equal to 0 or 1 of the monomer of formula (IV) has a total number of carbon atoms ranging from 8 to 38.

13. The composition as claimed in claim 9 , 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 9 , in which the oligomer A2 has a number-average degree of polymerization ranging from 2 to 100.

15. The composition as claimed in claim 9 , 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 the mixing of at least:
a lubricant oil; and
a compos

Assignees

• Total Marketing Services

Inventors

• Descroix Gregory
• Briand Fanny

Classifications

• C10N2040/25

  Internal-combustion engines · CPC title

• C08F275/00

  Macromolecular compounds obtained by polymerising monomers on to polymers of monomers containing phosphorus, selenium, tellurium or a metal as defined in group C08F30/00 · CPC title

• C10M139/00

  Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00 · CPC title

• C10M169/044

  the additives being a mixture of non-macromolecular and macromolecular compounds · CPC title

• C10M2209/084

  Acrylate; Methacrylate · CPC title