Copolymer that can be used as detergent additive for fuel

Patent metadata

Field	Value
Publication number	US-10752853-B2
Application number	US-201615761400-A
Country	US
Kind code	B2
Filing date	Sep 15, 2016
Priority date	Sep 18, 2015
Publication date	Aug 25, 2020
Grant date	Aug 25, 2020

Abstract

A block copolymer including: at least one block A of following formula (I):

in which p is an integer ranging from 2 to 100, R1′ is selected from hydrogen and the methyl group, R2′ is chosen from C1 to C34 hydrocarbon-based chains, at least one block B of following formula (II):

in which n is an integer ranging from 2 to 40, R1 is chosen from hydrogen and the methyl group, Z is chosen from the oxygen atom and the group —NR′— with R′ being chosen from a hydrogen atom and C1 to C12 hydrocarbon-based chains, G is a C1 to C34 hydrocarbon-based chain substituted by at least one quaternary ammonium group and optionally one or more hydroxyl groups. Also, the use of such a block copolymer as detergent additive in an internal combustion engine liquid fuel.

First claim

The invention claimed is:

1. A fuel composition comprising:
(1) a liquid fuel derived from one or more sources chosen from the group consisting of mineral, animal, plant and synthetic sources, and
(2) from 5 to 5000 ppm of one or more block copolymers comprising:
at least one block A of formula (I) below, which consists of a chain of structural units derived from an alkyl (meth)acrylate monomer (m a ):

in which
p is an integer ranging from 2 to 100,
R 1 ′ is chosen from hydrogen and a methyl group,
R′ 2 is chosen from C 1 to C 34 hydrocarbon-based chains,
at least one block B of formula (II) below, which consists of a chain of structural units derived from an alkyl (meth)acrylate or alkyl(meth)acrylamide monomer (m b ):

in which
n is an integer ranging from 2 to 40,
R 1 is chosen from hydrogen and a methyl group,
Z is chosen from an oxygen atom and a group —NR′— with R′ being chosen from a hydrogen atom and C 1 to C 12 hydrocarbon-based chains,

G is a C i to C 34 hydrocarbon-based chain substituted with at least one quaternary ammonium group and optionally one or more hydroxyl groups.

2. The fuel composition as claimed in claim 1 , comprising at least 10 ppm of block copolymer(s) (2).

3. The fuel composition as claimed in claim 1 , in which the fuel (1) is chosen from hydrocarbon-based fuels, fuels that are not essentially hydrocarbon-based, and mixtures thereof.

4. The fuel composition as claimed in claim 1 , in which the monomer (m a ) is chosen from C 4 to C 30 alkyl acrylates and C 4 to C 30 alkyl methacrylates.

5. The fuel composition as claimed in claim 1 , in which the quaternary ammonium group is chosen from pyrrolinium, pyridinium, imidazolium, triazolium, triazinium, oxazolium and isoxazolium quaternary salts.

6. The fuel composition as claimed in claim 1 , in which the quaternary ammonium group is chosen from trialkylammonium, guanidinium and iminium quaternary salts.

7. The fuel composition as claimed in claim 1 , in which block B is represented by one of the formulae (III) and (IV) below:

in which
X − is chosen from hydroxide and halide ions and organic anions,
R 2 is chosen from C 1 to C 34 hydrocarbon-based chains, substituted with at least one hydroxyl group,
R 3 , R 4 and R 5 are identical or different and chosen independently from C 1 to C 18 hydrocarbon-based chains, it being understood that the alkyl groups R 3 , R 4 and R 5 may contain one or more groups chosen from: a nitrogen atom, an oxygen atom and a carbonyl group and that the groups R 3 , R 4 and R 5 may be connected together in pairs to form one or more rings,
R 6 and R 7 are identical or different and chosen independently from C i to C 18 hydrocarbon-based chains, it being understood that the groups R 6 and R 7 may contain one or more groups chosen from: a nitrogen atom, an oxygen atom and a carbonyl group and that the groups R 6 and R 7 may be connected together to form a ring.

8. The fuel composition as claimed in claim 1 , in which the block copolymer is obtained by sequenced polymerization, optionally followed by one or more post-functionalizations.

9. The fuel composition as claimed in claim 1 , in which the copolymer is a copolymer comprising at least one sequence of blocks AB, ABA or BAB in which said blocks A and B form a sequence without the presence of an intermediate block of different chemical nature.

10. The fuel composition as claimed in claim 1 , in which p is an integer ranging from 2 to 40.

11. The fuel composition as claimed in claim 1 , in which p is an integer greater than 40 and less than or equal to 100.

12. The fuel composition as claimed in claim 7 , in which the group R 2 is represented by one of the formulae (V) and (VI) below:

in which
R 8 is chosen from C 1 to C 32 hydrocarbon-based chains,
R 9 is chosen from hydrogen and C 1 to C 6 alkyl groups.

13. The fuel composition as claimed in claim 12 , in which block B of formula (III), (IV), (V) or (VI) is derived from a monomer (m b ) obtained by the reaction:
of a tertiary amine of formula NR 3 R 4 R 5 or R 6 N═R 7 , and
of a (meth)acrylate or (meth)acrylamide intermediate monomer (m i ) of formula (VII) below:

14. The fuel composition as claimed in claim 12 , in which block B is obtained by post-functionalization of an intermediate polymer Pi comprising at least one block P of formula (VIII) below:

in which
said post-functionalization corresponds to the reaction of said intermediate polymer Pi with a tertiary amine NR 3 R 4 R 5 or R 6 N═R 7 .

15. The fuel composition as claimed in claim 14 , in which the intermediate polymer Pi also comprises at least one block A of formula (I).

Assignees

• Total Marketing Services

Inventors

• Prevost Julie

Classifications

• C08F2/38

  Polymerisation using regulators, e.g. chain terminating agents {, e.g. telomerisation} · CPC title

• C10L1/1963 Primary

  mono-carboxylic · CPC title

• C10L10/06

  for facilitating soot removal · CPC title

• C08F8/32

  by reaction with amines · CPC title

• C08F8/44

  Preparation of metal salts or ammonium salts · CPC title