Amphoterically-modified oligopropyleneimine ethoxylates for improved stain removal of laundry detergents

Patent metadata

Field	Value
Publication number	US-12163110-B2
Application number	US-202117999967-A
Country	US
Kind code	B2
Filing date	May 19, 2021
Priority date	May 29, 2020
Publication date	Dec 10, 2024
Grant date	Dec 10, 2024

Abstract

Disclosed herein are amphoterically-modified ethoxylated oligoamines, their manufacture, and methods of using them.

First claim

The invention claimed is:

1. An amphoterically-modified oligopropyleneimine ethoxylates (A) of general formula (I)

wherein
R 1 are the same or different and selected from C 1 -C 4 -alkyl, H and a free electron pair, wherein at least 50% of all R 1 are C 1 -C 4 -alkyl,
EO means —CH 2 —CH 2 —O,
Y are the same or different and selected from the group consisting of SO 3 − and H, wherein at least 30% of all Y are SO 3 − ,
x are the same or different and selected in a range of from 5 to 50, and n is 1, 2 or 3.

2. The amphoterically-modified oligopropyleneimine ethoxylates (A) according to claim 1 , wherein n=1, 2 or 3, at least 80% of R 1 are C 1 -C 4 -alkyl and the ratio of R 1 ═C 1 -C 4 -alkyl to Y═SO 3 − is on average from 1.0:1.0 to 1.0:0.8.

3. The amphoterically-modified oligopropyleneimine ethoxylates (A) according to claim 1 , wherein n=2 or 3 and at least 90% of all R 1 are methyl.

4. The amphoterically-modified oligopropyleneimine ethoxylates (A) according to claim 1 , wherein n=2, at least 90% of all R 1 are methyl and x=15-30.

5. A mixture of compounds comprising at least one amphoterically-modified oligopropyleneimine ethoxylate (A) according to claim 1 wherein n=2, and at least one isomeric compound according to formula (II)

wherein
R 1 are the same or different and selected from the group consisting of C 1 -C 4 -alkyl, H and a free electron pair, wherein at least 50%, of all R 1 are C 1 -C 4 -alkyl,
EO means —CH 2 —CH 2 —O,
Y are the same or different and selected from the group consisting of SO 3 − and H, wherein at least 30% of all Y are SO 3 − ,
x are the same or different and selected in a range of from 5 to 50.

6. The mixture according to claim 5 comprising an amphoterically-modified oligopropyleneimine ethoxylate (A) according to formula (I) and compounds according to formula (II) in a total molar ratio in the range of from 10:1 or higher.

7. The mixture comprising a compound according to claim 5 , wherein said mixture additionally comprises the sulfate of an alkali metal and/or an amine.

8. The mixture according to claim 7 , wherein said mixture additionally comprises the sulfate salt of an alkanolamine.

9. A process for making amphoterically-modified oligopropyleneimine ethoxylates (A) according to claim 1 , said process comprising the steps of
(a) providing an amine selected from the group consisting of ammonia, 1,3-propylenediamine, bis-(3,3′-aminopropyl)amine, and bis-(3,3′-aminopropyl)-1,3-propylenediamine, and mixtures thereof
(b) optionally performing cyanoethylation of said amine with acrylonitrile in a ratio from 100:1 to 1:2.5, followed by hydrogenation, to obtain oligopropyleneimines with 2, 3 and 4 repeating units
(c) optionally performing purification of the oligopropyleneimines from step (b)
(d) performing ethoxylation of said amine and/or oligopropyleneimine from step a, b or c, and
(e) performing at least partial quaternization and transsulfation with a di-C 1 -C 4 -alkyl sulfate.

10. The process according to claim 9 , wherein the purification step (c) is performed to obtain oligopropyleneimines with 2, 3 and 4 repeating units, or mixtures thereof, with a purity of at least 80 wt %.

11. The process according to claim 9 , wherein the at least partial quaternization in step (e) is performed with dimethyl sulfate.

12. The process according to claim 9 , wherein the transsulfation in step (e) is performed with sulfuric acid as a catalyst.

13. The process according to claim 9 , wherein the transsulfation in step (e) is performed more than or equal to 80% and a slightly cationic or net neutral polymer is obtained.

14. The process according to claim 12 , wherein said process includes the subsequent step of neutralization of the sulfuric acid with a base selected from the group consisting of alkali metal hydroxides and amines.

15. The process according to claim 14 , wherein the base for neutralization of the sulfuric acid is selected from the group consisting of alkanolamines.

16. The process according to claim 9 , wherein the ethoxylation in step (d) is performed in two sub-steps:
(i) conversion with up to one mole of ethylene oxide per N—H function followed by
(ii) conversion with more ethylene oxide under alkaline catalysis.

17. The amphoterically-modified oligopropyleneimine ethoxylates (A) obtainable by a process according to claim 9 .

18. A laundry formulation, comprising at least one of the amphoterically-modified oligopropyleneimine ethoxylates (A) according to claim 1 .

19. A laundry formulation according to claim 18 , further comprising 2-phenoxyethanol and/or 4,4′-dichloro-2-hydroxydiphenylether.

Assignees

• Basf Se

Inventors

• Tuerk Holger
• Engert Susanne Carina
• Haydl Alexander Michael
• Carswell Robert John
• Bennett Julie

Classifications

• C11D2111/12

  Soft surfaces, e.g. textile · CPC title

• C08G73/0226

  Quaternisation of polyalkylene(poly)amines · CPC title

• C08G73/0206

  Polyalkylene(poly)amines · CPC title

• C08G73/024

  Polyamines containing oxygen in the form of ether bonds in the main chain · CPC title

• C11D3/3723 Primary

  Polyamines or polyalkyleneimines · CPC title