Polyesteramines and polyesterquats

Patent metadata

Field	Value
Publication number	US-11802179-B2
Application number	US-201816638369-A
Country	US
Kind code	B2
Filing date	Aug 8, 2018
Priority date	Aug 16, 2017
Publication date	Oct 31, 2023
Grant date	Oct 31, 2023

Abstract

Provided is a compound which may be obtained by esterification condensation of components as described herein. The compound may be used as a collector for ore enrichment (flotation), as a corrosion inhibitor, as a viscosity enhancer, emulsifier or stabilizer that is useful for the oil and gas industry, as a clay modifier, as an adhesion promoter, as an antiagglomerant additive, as an additive in haircare products, as a fabric softener, as an antistatic agent in polymers, as a bitumen emulsion additive, as a detergency cationic agent, as a fertilizer additive, as an antiagglomerant for hydrates, as a lubrication or adhesion-promoting additive, for example.

First claim

The invention claimed is:

1. A compound which may be obtained by esterification condensation of:
A/ an alkoxylated fatty amine of formula (I), or the product of partial or total quaternization of said alkoxylated fatty amine of formula (I):

in which:
R 1 is chosen from a hydrocarbyl group containing 8 to 24 carbon atoms, and a group of formula R 4 —O-(A′O) w -T-, in which R 4 is a hydrocarbyl group containing 8 to 24 carbon atoms, w represents an integer in the range from 0 to 20, A′O is an alkylenoxy group containing 2 to 4 carbon atoms, T is alkylene with 1 to 6 carbon atoms,
AO is an alkylenoxy group containing 2 to 4 carbon atoms,
B is chosen from a C 1 -C 4 alkyl, an aryl and an arylalkyl group,
m represents an integer between 1 and 20, limits inclusive,
n represents an integer between 1 and 20, limits inclusive,
s is 1, 2 or 3, and
y is an integer from 0 to 5,

B/ with a dicarboxylic acid, or a derivative thereof, of formula (II):

in which
D is chosen from —F, —Cl, Br and —OR 3 , in which R 3 is hydrogen or a C 1 -C 4 alkyl group,
R 2 is chosen from the group constituted by:
a direct bond,
a linear or branched, saturated or unsaturated C 1 -C 20 hydrocarbon-based chain optionally substituted with one or more —OH groups, a substituted alkylene radical, said alkylene radical being substituted with 1 or 2 —OH groups, an alkenylene radical containing from 1 to 20 carbon atoms, a substituted alkenylene radical, said alkenylene radical being substituted with 1 or 2 methyl and/or methylene groups,
a cycloalkylene group,
cycloalkenylene and
arylene

C/ with an (alkyl)alkanolamine of formula (III) derivative or product of partial or total quaternization of said (alkyl)alkanolamine derivative of formula (III):

in which:
A″O represents an alkylenoxy group containing from 2 to 4 carbon atoms,
u represents an integer between 1 and 20, limits inclusive,
u′ represents an integer between 1 and 20, limits inclusive,
R 7 is chosen from a hydrocarbyl group containing 1 to 7, an aryl or arylalkyl group, a group of formula H—(OA″) v - (in which v represents an integer between 1 and 20, limits inclusive), HO(CH 2 ) q —, and a group of formula (IV):

in which R 8 and R 9 , which may be identical or different, are chosen from a hydrocarbyl group containing 1 to 6 carbon atoms, and q is an integer from 1 to 10, limits inclusive, or R 8 and R 9 , together with the nitrogen atom to which they are attached, form a 5-, 6- or 7-membered ring, optionally including one or more heteroatoms chosen from oxygen, nitrogen and sulfur.

2. The compound as claimed in claim 1 , in which the radical R 1 of the fatty amine of formula (I) includes 8 or more than 8 carbon atoms, limits inclusive, and the radical R 7 of the (alkyl)alkanolamine derivative of formula (III) includes 6 carbon atoms or less, limits inclusive.

3. The compound as claimed in claim 1 , in which the radical R 1 and the radical R 7 of the fatty amine of formula (I) and of the (alkyl)alkanolamine derivative of formula (III), respectively, are such that the difference in the number of carbon atoms they include is greater than 2, limits inclusive.

4. The compound as claimed in claim 1 , in which some or all of the nitrogen atoms also react with a reagent of formula R 5 X, in which R 5 is chosen from a C 1 -C 6 hydrocarbyl group, a phenyl and a phenylalkyl, group, and X is chosen from halogens, sulfates, carbonates, and the like.

5. The compound as claimed in claim 1 , in which the alkoxylated fatty amine of formula (I) is of formula (IA):

which is the alkoxylated fatty amine of formula (I) in which y represents 0 and R 1 , AO, m and n are as defined in claim 1 ,
and also the corresponding partially or totally quaternized derivatives thereof.

6. The compound as claimed in claim 1 , in which the (alkyl)alkanolamine derivative of formula (III) is of formula (IIIA):

which is the (alkyl)alkanolamine of formula (III) in which u and u′ each represent 1, A″O is ethylenoxy and R 7 is as defined in claim 1 ,
and also the corresponding partially or totally quaternized derivatives thereof.

7. The compound as claimed in claim 1 , in which the (alkyl)alkanolamine derivatives of formula (III) comprise, but are not limited to, triethanolamine, methyldiethanolamine, ethyldiethanolamine, propyldiethanolamine, butyldiethanolamine, isobutyldiethanolamine, pentyldiethanolamine, phenyldiethanolamine, hexyldiethanolamine, heptyldiethanolamine, and also the corresponding alkoxylation products thereof.

8. The compound as claimed in claim 1 , in which the dicarboxylic acid derivative of general formula (II) is chosen from a dicarboxylic acid, a dicarboxylic acid halide, a dicarboxylic acid diester or a cyclic anhydride of a dicarboxylic acid.

9. The compound as claimed in claim 1 , wherein the dicarboxylic acid derivatives of general formula (II) comprise oxalic acid, malonic acid, succinic acid, glutaric acid, glutaconic acid, adipic acid, muconic acid, pimelic acid, phthalic acid and isomers thereof, tetrahydrophthalic acid, malic acid, maleic acid, fumaric acid, suberic acid, mesaconic acid, sebacic acid, azelaic acid, tartaric acid, itaconic acid, glutinic acid, citraconic acid, brassylic acid, dodecanedioic acid, traumatic acid, thapsic acid, the corresponding acid chlorides thereof, the corresponding methyl or ethyl esters thereof, and the corresponding cyclic anhydrides thereof, and also mixtures thereof.

10. The compound as claimed in claim 1 , in which the mole ratio between the reagents [(I)+(III)] and (II) is from 2:1 to 1:2.

11. The compound as claimed in claim 1 , in which the mole ratio between the reagents [(I)+(III)] and (II) is from 2:1 to 1:1.

12. The compound as claimed in claim 1 , in which the mole ratio between (I) and (III) is from 15:1 to 1:15.

13. A compound of general formula (1):

in which:
R 2 is chosen from:
a direct bond,
a linear or branched, saturated or unsaturated C 1 -C 20 hydrocarbon-based chain optionally substituted with one or more —OH groups, a substituted alkylene radical, said alkylene radical being substituted with 1 or 2 —OH groups, an alkenylene radical containing from 1 to 20 carbon atoms, a substituted alkenylene radical, said alkenylene radical being substituted with 1 or 2 methyl and/or methylene groups,
a cycloalkylene group,
cycloalkenylene and
arylene

R 5 is chosen from a C 1 -C 6 hydrocarbyl group, a phenyl group and a phenylalkyl group,
X is chosen from halogens, sulfates, carbonates, and the like,
t is 0 or 1,
p is an integer in the range from 1 to 15,
QO represents an alkylenoxy group containing from 2 to 4 carbon atoms, given that all the Q groups present in the compound of formula (1) may be identical or different,
q 1 , q 2 , q 3 and q 4 , which may be identical to or different from each other, each represent an integer between

Assignees

• Arkema France

Inventors

• Jorda Eric
• Baloche Alain
• Barreto Gilles
• Gillet Jean-Phillippe

Classifications

• C08G63/6856 Primary

  Dicarboxylic acids and dihydroxy compounds · CPC title

• B03D1/011

  Quaternary ammonium compounds · CPC title

• C07C217/28

  having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines · CPC title

• D06M15/507

  Polyesters · CPC title

• B03D2201/02

  Collectors · CPC title