IP Library Granted Patent US 12680055
Granted Patent B2
US 12680055 · App. 18/560,997 · Granted Jul 14, 2026

Anthracene-9,10-dione derivatives as photoactivators in detergents

Inventors: Christian Kropf (Hilden, DE); Nadia Ledermann (Duisburg, DE)
Assignee: HENKEL AG & CO. KGAA
C11D3/3955C11D3/2072C11D2111/12
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Quick Facts
Patent No.
US 12680055
App. No.
18/560,997
Granted
Jul 14, 2026
Kind
B2
Abstract

Anthracene-9,10-dione derivatives are capable of producing bleach-active species under irradiation of visible light, which lead to an increase of the bleaching power during the washing of textiles.

Claims (21)

1 . A washing agent comprising alkyloxy-substituted anthracene-9,10-dione of the general formula (I),

in which R 1 and R 2 independently of one another is H, SO 3 − M + or an optionally substituted linear or branched alkyl radical having 1 to 20 C atoms, with the proviso that at least one of the radicals R 1 or R 2 is an optionally substituted linear or branched alkyl radical having 1 to 20 C atoms, X is H or SO 3 − M + and M + is a proton, an alkali metal ion or an ammonium ion or mixtures thereof; and

a nonionic, anionic, cationic, and/or amphoteric surfactant.

2 . The agent according to claim 1 , characterized in that it contains 0.00001 wt. % to 1 wt. % of alkyloxy-substituted anthracene-9,10-dione of the general formula (I).

3 . The agent according to claim 1 , characterized in that it is liquid.

4 . The agent according to claim 1 , characterized in that it does not contain any bleaching agents.

5 . The agent according to claim 1 , characterized in that it is present as a prefabricated dosage unit with a water-soluble coating.

6 . A method for removing stains from textile materials comprising

adding an Alkyloxy-substituted anthracene-9,10-diones of the general formula (I),

in which R 1 and R 2 independently of one another is H, SO 3 − M + or an optionally substituted linear or branched alkyl radical having 1 to 20 C atoms, with the proviso that at least one of the radicals R 1 or R 2 is an optionally substituted linear or branched alkyl radical having 1 to 20 C atoms, x is H or SO 3 − M + and M + is a proton, an alkali metal ion or an ammonium ion or mixtures thereof, in an aqueous washing liquid in which the washing in need of textile materials is located, and

irradiating the aqueous washing liquid with visible light.

7 . The method according to claim 6 , characterized in that light in the wavelength range from 400 nm to 600 nm is used.

8 . The method according to claim 6 , characterized in that the alkyloxy-substituted anthracene-9,10-dione of the general formula (I) is used in concentrations in the range from 0.0001 mmol/l to 0.1 mmol/l in aqueous washing liquor.

9 . The agent according to claim 1 , characterized in that, in formula (I), R 1 and R 2 is independently an optionally substituted linear or branched alkyl radical having 1 to 20 C atoms, and/or R 1 and R 2 is substituted and substituents selected from —OH, —COO − M, —SO 3 − M, —OSO 3 − M, —N(CH 2 CH 3 ) 3 Hal − , wherein M + for a proton, an alkali metal ion, an ammonium ion and mixtures thereof and Hal − for Cl − , Br − , J − , F − and mixtures thereof and M + and Hal − can also be missing if —COO − , —SO 3 − , and —OSO 3 − and —N(CH 2 CH 3 ) 3 are present in charge-balancing quantity.

10 . The method according to claim 6 , characterized in that, in formula (I), R 1 and R 2 is independently an optionally substituted linear or branched alkyl radical having 1 to 20 C atoms, and/or R 1 and R 2 is substituted and substituents selected from —OH, —COO − M, —SO 3 − M, —OSO 3 − M, —N(CH 2 CH 3 ) 3 Hal − , wherein M + for a proton, an alkali metal ion, an ammonium ion and mixtures thereof and Hal − for Cl − , Br − , J − , F − and mixtures thereof and M + and Hal − can also be missing if —COO − , —SO 3 − , and —OSO 3 − and —N(CH 2 CH 3 ) 3 are present in charge-balancing quantity.

11 . The agent according to claim 1 , characterized in that it contains 0.001 wt. % to 0.1 wt. % of alkyloxy-substituted anthracene-9,10-dione of the general formula (I).

12 . The method according to claim 6 , characterized in that light in the wavelength range from 450 nm to 525 nm is used.

13 . The method according to claim 6 , characterized in that the alkyloxy-substituted anthracene-9,10-dione of the general formula (I) is used in concentrations in the range from 0.001 mmol/l to 0.01 mmol/l in aqueous washing liquor.

14 . A washing agent comprising alkyloxy-substituted anthracene-9,10-dione of the general formula (I),

in which R 1 and R 2 independently of one another is H, SO 3 − M + or an optionally substituted linear or branched alkyl radical having 1 to 20 C atoms, with the proviso that at least one of the radicals R 1 or R 2 is an optionally substituted linear or branched alkyl radical having 1 to 20 C atoms, X is H or SO 3 − M + and M + is a proton, an alkali metal ion or an ammonium ion or mixtures thereof,

characterized in that the washing agent is present as a prefabricated dosage unit with a water-soluble coating.