IP Library › Granted Patent US 11,560,532
Granted Patent B2
US 11,560,532 · App. 17/228,524 · Granted Jan 24, 2023

Detergent composition with catechol metal complex compound

Inventors: Frank Meier (Duesseldorf, DE); Mareile Job (Leverkusen, DE); Christian Kropf (Hilden, DE); Ulrich Pegelow (Duesseldorf, DE)
Assignee: Henkel AG & Co. KGaA
C11D3/168C07F11/005C07F13/005C07F15/025C09B57/10C11D1/83C11D3/40C11D11/0017C11D17/045C11D1/22C11D1/29C11D1/72C11D1/721
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Quick Facts
Patent No.
US 11,560,532
App. No.
17/228,524
Granted
Jan 24, 2023
Kind
B2
Abstract

Catechol metal complex compounds of formula (I) are colored and can be used to give color to surfactant compositions. Detergents containing these catechol metal complex compounds do not stain the textile even after repeated use.

Claims (34)

1. A detergent containing, in each case based on the total weight of the detergent

in a total amount from 0.001 to 10.0 wt. % at least one catechol metal complex compound of formula (I)

where

R 1 and R 2 independently represent a hydrocarbon group having 1 to 20 carbon atoms, which is optionally substituted by at least one group selected from hydroxy, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkoxy(CH 2 CH 2 O) n —, —NR′R″ or —N + R′R″R′″X − , where n=1 to 10, R′, R″ and R′″ independently represent H or a linear or branched aliphatic hydrocarbon group having 1 to 3 carbon atoms and X − represents an anion,

Z 1 and Z 2 independently represent OH or O − ,

M represents a metal cation of a transition metal or lanthanoid,

q as the charge number of the metal cation M represents a number 2, 3 or 4,

as the charge number of the catechol ligand represents a number 0, 1 or 2,

r represents a number 1, 2, 3 or 4,

and

at least one surfactant in a total amount from 2 to 70 wt. %.

2. The detergent according to claim 1 wherein, in formula (I) the groups R 1 and R 2 independently represent an alkyl group, an alkoxyalkyl group, a hydroxyalkyl group, a hydroxyalkyloxyalkyl group, (N-hydroxyethyl)-aminoethyl, (N-methoxyethyl)-aminoethyl or (N-ethoxyethyl)-aminoethyl, or an aromatic group.

3. The detergent according to claim 2 wherein, in formula (I) the groups R 1 and R 2 independently represent an alkyl group, an alkoxyalkyl group, a hydroxyalkyl group, a hydroxyalkyloxyalkyl group, (N-hydroxyethyl)-aminoethyl, (N-methoxyethyl)-aminoethyl, (N-ethoxyethyl)-aminoethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, iso-butyl, n-pentyl, iso-pentyl, neopentyl, hexyl, 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 2-methoxyethyl, 2-ethoxyethyl, 3-methoxypropyl, 3-ethoxypropyl, (N-hydroxyethyl)-aminoethyl, or phenyl.

4. The detergent according to claim 1 wherein, in formula (I) the groups R 1 and R 2 are the same.

5. The detergent according to claim 1 wherein, in formula (I) M is selected from Fe, Mn, Cr, Ni, Co, Ce, Cu or hydrates of these metal ions.

6. The detergent according to claim 1 wherein, in formula (I) M represents a metal cation of a transition metal or a metal cation from Ti, Zr, Hf, V, Nb, Ta, Cr, Mo, W, Mn, Fe, Ru, Co, Ni, Cu, Zn, Ce or Sm.

7. The detergent according to claim 1 , wherein the detergent has a pH at 20° C. from 6 to 11.5.

8. The detergent according to claim 1 , wherein the at least one surfactant comprises anionic surfactant and/or nonionic surfactant.

9. The detergent according to claim 1 , wherein the catechol metal complex compound of formula (I) absorbs light in a wavelength from 400 to 800 nm, measured by means of a two-beam spectrophotometer at a concentration of the complex of 10 −5 mol/L in water at 20° C., a pH of 8 and a layer thickness of 1 cm.

10. The detergent according to claim 1 , wherein the detergent additionally contains at least one free catechol compound of formula (II) or the salt thereof

where

R 3 and R 4 independently represent a hydrocarbon group having 1 to 20 carbon atoms, which is optionally substituted by at least one group selected from hydroxy, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkoxy(CH 2 CH 2 O) n —, —NR′R″ or —N + R′R″R′″X − , where n=1 to 10,

R′, R″ and R′″ independently represent H or a linear or branched aliphatic hydrocarbon group having 1 to 3 carbon atoms and X − represents an anion,

with the proviso that the catechol compound of formula (II) and the salt thereof are different from compounds of formula (I).

11. The detergent according to claim 10 , wherein the detergent contains the at least one free catechol compound of formula (II) in a total amount from 0.01 to 10.0 wt. %.

12. The detergent, according to claim 1 , wherein the detergent is a liquid detergent.

13. A multi-component detergent, wherein at least one component is a detergent according to claim 1 and at least one further additional component is selected from at least one composition selected from a liquid composition or a powder composition or granules.

14. The multi-component detergent according to claim 13 , wherein the multi-component detergent is in the form of a multi-chamber pouch.

15. The multi-component detergent according to claim 14 , wherein the multi-component detergent is in the form of a multi-chamber pouch made of a water-soluble film.

16. The multi-component detergent according to claim 13 , wherein the multi-component detergent contains a bittering agents, and the bittering agents is contained in the detergent and/or in the container of the multi-component detergent.

17. The multi-component detergent according to claim 13 , wherein the detergent is a liquid detergent.

18. A method for washing textiles, comprising the steps of

adding a detergent, according to claim 1 , to a fabric or textile; and

carrying out a washing procedure.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 22, 2021
From: MEIER, FRANK; JOB, MAREILE; KROPF, CHRISTIAN; PEGELOW, ULRICH
To: HENKEL AG & CO. KGAA
Reel/Frame 057564/0743 →
Priority Claims (1)
DE 10 2018 217 393.1 · Oct 11, 2018 · national
Continuity (2)
Continuation PCTEP2019065984 · Jun 18, 2019
Related Publication 20210230513A1 · Jul 29, 2021