Anionic surfactants and detergents comprising them

Patent metadata

Field	Value
Publication number	US-10988710-B2
Application number	US-201815887611-A
Country	US
Kind code	B2
Filing date	Feb 2, 2018
Priority date	Aug 3, 2015
Publication date	Apr 27, 2021
Grant date	Apr 27, 2021

Abstract

Surfactants of the general formula (I) in which R 1 is a linear or branched akyl radical having 6 to 20, especially 10 to 16 C atoms, R 2 and R 3 independently of one another are H or H 3 CO, and M is hydrogen, an alkali metal or a moiety N + R 4 R 5 R 6 , in which R 4 , R 5 and R 6 independently of one another are hydrogen, an alkyl group having 1 to 6 C atoms or a hydroxyalkyl group having 2 to 6 C atoms, are readily incorporated into laundry detergents or cleaning products, possess outstanding performance qualities and can be prepared on the basis of renewable raw materials.

First claim

What is claimed is:

1. An anionic surfactant of general formula (I),

in which R′ denotes a linear or branched alkyl functional group having 6 to 20 carbon atoms, R 2 and R 3 , independently of one another, denote H or H 3 CO, and M denotes hydrogen, an alkali metal or an N + R 4 R 5 R 6 grouping, in which R 4 , R 5 and R 6 , independently of one another, denote hydrogen, an alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group having 2 to 6 carbon atoms.

2. A method for producing an anionic surfactant of general formula (I),

in which R 1 denotes a linear or branched alkyl functional group having 6 to 20 carbon atoms, R 2 and R 3 , independently of one another, denote H or H 3 CO, and M denotes hydrogen, an alkali metal or an N + R 4 R 5 R 6 grouping, in which R 4 , R 5 and R 6 , independently of one another, denote hydrogen, an alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group having 2 to 6 carbon atoms,
comprising the step of sulfonating a compound of general formula (II),

in which R 1 denotes a linear or branched alkyl functional group having 6 to 20 carbon atoms, R 2 and R 3 , independently of one another, denote H or H 3 CO, with a sulfating agent,
and neutralization by way of subsequent reaction with MOH, wherein M denotes an alkali metal or an N + R 4 R 5 R 6 grouping, in which R 4 , R 5 and R 6 , independently of one another, denote hydrogen, an alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group having 2 to 6 carbon atoms.

3. A method for producing a compound of general formula (II),

in which R 1 denotes a linear or branched alkyl functional group having 6 to 20 carbon atoms, le and R 3 , independently of one another, denote H or H 3 CO,
comprising the step of reacting a compound of general formula (III),

in which R 2 and R 3 , independently of one another, are H or H 3 CO,
with a compound R 1 -Hal, in which R 1 denotes a linear or branched alkyl functional group having 6 to 20 carbon atoms, and Hal denotes chlorine, bromine, iodine or mixtures thereof, under alkaline conditions.

4. A washing or cleaning agent, comprising an anionic surfactant of general formula (I),

in which R 1 denotes a linear or branched alkyl functional group having 6 to 20 carbon atoms, R 2 and R 3 , independently of one another, denote H or H 3 CO, and M denotes hydrogen, an alkali metal or an N + R 4 R 5 R 6 grouping, in which R 4 , R 5 and R 6 , independently of one another, denote hydrogen, an alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group having 2 to 6 carbon atoms.

5. The washing or cleaning agent according to claim 4 , characterized by comprising 1 wt. % to 99 wt. % of the surfactant of general formula (I).

6. The washing or cleaning agent according to claim 4 , characterized by additionally comprising up to 99 wt. %, of a further surfactant.

7. The washing or cleaning agent according to claim 4 , characterized by being particulate and comprising builders.

8. The washing or cleaning agent according to claim 4 , characterized by being liquid and comprising 1 wt. % to 90 wt. % water, water-miscible solvent or a mixture of water and water-miscible solvent.

9. The washing or cleaning agent according to claim 4 , characterized by being present portioned and ready-for-use in individual doses in a chamber formed of water-soluble material.

10. The anionic surfactant, according to claim 1 , of general formula (I),

in which R 1 denotes a linear or branched alkyl functional group having 10 to 16 carbon atoms, R 2 and R 3 , independently of one another, denote H or H 3 CO, and M denotes hydrogen, an alkali metal or an N + R 4 R 5 R 6 grouping, in which R 4 , R 5 and R 6 , independently of one another, denote hydrogen, an alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group having 2 to 6 carbon atoms.

11. The method according to claim 2 , for producing an anionic surfactant of general formula (I),

in which R 1 denotes a linear or branched alkyl functional group having 10 to 16 carbon atoms, R 2 and R 3 , independently of one another, denote H or H 3 CO, and M denotes hydrogen, an alkali metal or an N + R 4 R 5 R 6 grouping, in which R 4 , R 5 and R 6 , independently of one another, denote hydrogen, an alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group having 2 to 6 carbon atoms,
comprising the step of sulfonating a compound of general formula (II),

in which R 1 denotes a linear or branched alkyl functional group having 10 to 16 carbon atoms, R 2 and R 3 , independently of one another, denote H or H 3 CO, with a sulfating agent,
and neutralization by way of subsequent reaction with MOH, wherein M denotes an alkali metal or an N + R 4 R 5 R 6 grouping, in which R 4 , R 5 and R 6 , independently of one another, denote hydrogen, an alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group having 2 to 6 carbon atoms.

12. The method according to claim 3 , for producing a compound of general formula (II),

in which R 1 denotes a linear or branched alkyl functional group having 10 to 16 carbon atoms, R 2 and R 3 , independently of one another, denote H or H 3 CO,
comprising the step of reacting a compound of general formula (III),

in which R 2 and R 3 , independently of one another, are H or H 3 CO,
with a compound R 1 -Hal, in which R 1 denotes a linear or branched alkyl functional group having 10 to 16 carbon atoms, and Hal denotes chlorine, bromine, iodine or mixtures thereof under alkaline conditions.

13. The method according to claim 3 , for producing a compound of general formula (II),

in which R 1 denotes a linear or branched alkyl functional group having 6 to 20 carbon atoms, R 2 and R 3 , independently of one another, denote H or H 3 CO,
comprising the step of reacting a compound of general formula (III),

in which R 2 and R 3 , independently of one another, are H or H 3 CO,
with a compound R 1 -Hal, in which R 1 denotes a linear or branched alkyl functional group having 6 to 20 carbon atoms, and Hal denotes bromine under alkaline conditions.

14. The washing or cleaning agent according to claim 4 , comprising an anionic surfactant of general formula (I),

Assignees

• Henkel Ag & Co Kgaa
• Studiengesellschaft Kohlm mbH
• Studiengesellschaft Kohle Mbh

Inventors

• Kropf Christian
• Schulz Alexander
• Hellmuth Hendrik
• Rinaldi Roberto
• Estevez Rivera Hebert Jesus

Classifications

• C11D1/22 Primary

  derived from aromatic compounds · CPC title

• C11D17/042

  Water soluble or water disintegrable containers or substrates containing cleaning compositions or additives for cleaning compositions · CPC title

• C07C305/18 Primary

  containing six-membered aromatic rings · CPC title

• C07C41/09

  by dehydration of compounds containing hydroxy groups · CPC title

• C07C303/24

  of esters of sulfuric acids · CPC title