Composition comprising thermoassociative and exchangeable copolymers

Patent metadata

Field	Value
Publication number	US-11840593-B2
Application number	US-201916979133-A
Country	US
Kind code	B2
Filing date	Mar 7, 2019
Priority date	Mar 7, 2018
Publication date	Dec 12, 2023
Grant date	Dec 12, 2023

Abstract

Compositions resulting from the mixing of at least: a comb polydiol copolymer A1 and a compound A2 including at least two boronic ester functional groups, the comb polydiol copolymer A1 including a main chain and side chains, at least a portion of the side chains of the copolymer A1 being composed of oligomers. They exhibit very varied rheological properties depending on the proportion of the compounds A1 and A2 used. Composition resulting from the mixing of at least one lubricating oil with such a composition of associative and exchangeable polymers and use of this composition for lubricating a mechanical part.

First claim

The invention claimed is:

1. A composition resulting from the mixing of at least:
a comb polydiol copolymer A1
and
a compound A2 comprising at least two boronic ester functional groups,
the comb polydiol copolymer A1 comprising a main chain and side chains, at least a portion of the side chains of the copolymer A1 being composed of oligomers comprising more than 30 carbon atoms.

2. The composition as claimed in claim 1 , in which at least a portion of the side chains of the copolymer A1 are composed of oligomers comprising at least 50 carbon atoms.

3. The composition as claimed in claim 1 , in which at least a portion of the side chains of the copolymer A1 are composed of oligomers which exhibit a degree of polymerization ranging from 5 to 1000.

4. The composition as claimed in claim 1 , in which the side chains composed of oligomers represent from 3% to 95% by weight, with respect to the total weight of the copolymer A1.

5. The composition as claimed in claim 1 , in which at least a portion of the side chains of the copolymer A1 are composed of oligomers 01 comprising a polyolefin fragment.

6. The composition as claimed in claim 5 , in which the side chains of the copolymer A1 composed of oligomers O1 comprise a polyolefin fragment having from 30 to 500 carbon atoms.

7. The composition as claimed in claim 5 , in which the side chains comprising a polyolefin fragment represent from 3% to 85% by weight, with respect to the total weight of the copolymer A1.

8. The composition as claimed in claim 5 , in which the oligomers O1 are present in the copolymer A1 in the form of repeat units corresponding to one or more monomers M6 of general formula (IX):

in which:
Q 1 is chosen from the group consisting of —H, —CH 3 and —CH 2 —CH 3 ;
Q 2 is chosen from the group consisting of -Q′, —O-Q′, —C(O)—O-Q′, —O—C(O)-Q′, —S—(CH 2 ) 2 —C(O)—O-Q′, —S-Q′, —N(H)—C(O)-Q′ and —C(O)—N(H)-Q′ group, with Q′ is a polyolefin,
n represents an integer chosen from 0 and 1,
A represents a divalent group chosen from the group consisting of -A 1 -, —O-(-A 2 -O—) n -A 1 -, —C(O)—O-(-A 2 -O—) n -A 1 -, —O—C(O)-(-A 2 -O—) n ′-A 1 -, —S—(-A 2 -O—) n -A 1 -, —N(H)—C(O)-(-A 2 -O—) n -A 1 - and —C(O)—N(H)-(-A 2 -O—) n -A 1 - with:
A 1 is a divalent radical chosen from the group consisting of a C 1 -C 30 alkyl, a C 6 -C 30 aryl and a C 6 -C 30 aralkyl,
A 2 is a divalent radical chosen from C 2 -C 4 alkyls,
n′ is an integer, n′ represents 0 or 1.

9. The composition as claimed in claim 1 , in which at least a portion of the side chains of the copolymer A1 are composed of oligomers O2 comprising repeat units corresponding to monomers M2 of general formula (II):

in which:
R 2 is chosen from the group consisting of —H, —CH 3 and —CH 2 —CH 3 ,
R 3 is chosen from the group consisting of —C(O)—O—R′ 3 , —O—R′ 3 , —S—R′ 3 and —C(O)—N(H)—R′ 3 , with R′ 3 is a C 1 -C 30 alkyl group.

10. The composition as claimed in claim 9 , in which at least a portion of the oligomers O2 comprise repeat units corresponding to monomers M1 of general formula (I):

in which:
R 1 is chosen from the group consisting of —H, —CH 3 and —CH 2 —CH 3 ;
y is an integer equal to 0 or 1;
Y represents a divalent linking group chosen from C 1 -C 20 alkyl chains, optionally comprising one or more ether —O— bridges;
X 1 and X 2 , which are identical or different, are chosen from the group consisting of hydrogen, tetrahydropyranyl, methyloxymethyl, tert-butyl, benzyl, trimethylsilyl and t-butyldimethylsilyl;

or else
X 1 and X 2 form, with the oxygen atoms, a bridge of formula:

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

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

in which:
the stars (*) symbolize the bonds to the oxygen atoms,
R″′ 2 is chosen from the group consisting of a C 6 -C 30 aryl, a C 7 -C 30 aralkyl and a C 2 -C 30 alkyl.

11. The composition as claimed in claim 1 , in which the copolymer A1 comprises repeat units corresponding to at least one monomer M3 of general formula (X):

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

12. The composition as claimed in claim 11 , in which the monomer M3 is styrene.

13. The composition as claimed in claim 11 , in which the repeat units corresponding to monomers of formula (X) represent from 2 mol % to 50 mol %, with respect to the total number of moles of the repeat units of which the copolymer A1 is composed.

14. The composition as claimed in claim 1 , in which the copolymer A1 exhibits a degree of branching ranging from 0.1 mol % to 10 mol %.

15. The composition as claimed in claim 1 , in which the comb copolymer A1 comprises nonoligomeric pendant chains which have a mean length ranging from 1 to 10 carbon atoms.

16. The composition as claimed in claim 1 , in which the main chain of the comb copolymer A1 has a number-average degree of polymerization ranging from 40 to 2000.

17. The composition as claimed in claim 1 , in which the oligomeric pendant chains of the comb copolymer A1 have a number-average degree of polymerization ranging from 8 to 1000.

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

in which:
w 1 and w 2 , which are identical or different, are integers chosen between 0 and 1;
R 4 , R 5 , R 6 and R 7 , which are identical or different, represent a group chosen from the group consisting of a hydrogen atom and a hydrocarbon group comprising from 1 to 30 carbon atoms, optionally substituted by one or more groups chosen from the group consisting of a hydroxyl and an —OJ or —C(O)—O-J group, with J a hydrocarbon group comprising from 1 to 24 carbon atoms;
L is a divalent linking group chosen from the group consisting of a C 6 -C 18 aryl, a C 6 -C 15 aralkyl and a C 2 -C 24 hydrocarbon chain;

a copolymer comprising at least
repeat units corresponding to 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 s are divalent linking groups, which are identical or different, chosen from the group consisting of a C 6 -C 18 aryl, a C 7 -C 24 aralkyl and a C 2 -C 24 alkyl;

X is a functional group chosen from the group consisting of —O—C(O)—, —C(O)—O—, —C(O)—N(H)—, —N(H)—C

Assignees

• Total Marketing Services
• Centre Nat Rech Scient
• Ecole Superieure Physique & Chimie Ind Ville De Paris
• Centre Nat De La Cherche Scentifique

Inventors

• Descroix Grégory
• Briand Fanny
• Nicolay Renaud
• Derouineau Thibault

Classifications

• C08F293/005 Primary

  using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent · CPC title

• C08F8/42

  Introducing metal atoms or metal-containing groups · CPC title

• C08F212/02

  Monomers containing only one unsaturated aliphatic radical · CPC title

• C08F220/1804

  C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate · CPC title

• C08F220/1812

  C12-(meth)acrylate, e.g. lauryl (meth)acrylate · CPC title