Surfactants with tetrahydrofuranyl system

Patent metadata

Field	Value
Publication number	US-11535816-B2
Application number	US-202016804901-A
Country	US
Kind code	B2
Filing date	Feb 28, 2020
Priority date	Aug 28, 2017
Publication date	Dec 27, 2022
Grant date	Dec 27, 2022

Abstract

The invention relates to surfactants of general formula (I) in which R1 and R2 represent independently of one another represent H and SO3−X+ with the proviso that at least one of R1 and R2 is not H, n and m represent independently from each other numbers from 0-21 under the proviso that 4<n+m<26, and X+ represents a charge-balancing anion. The surfactants can be incorporated into detergents or cleaning agents, have excellent technological application properties and can be produced based on renewable raw materials.

First claim

What is claimed is:

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

in which R 1 and R 2 represent, independently of one another, H and SO 3 − X + , with the proviso that at least one of R 1 and R 2 is not H, n and m represent, independently of one another, numbers from 0 to 21, with the proviso that 4<n+m<26, and X + represents a charge-balancing cation.

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

in which R 1 and R 2 represent, independently of one another, H and SO 3 − X + , with the proviso that at least one of R 1 and R 2 is not H, n and m represent, independently of one another, numbers from 0 to 21, with the proviso that 4<n+m<26, and X + represents a charge-balancing cation, by a) acid-induced separation of water from ribitol, arabitol, xylitol, or mixtures thereof, optionally b) introducing protective groups for the two vicinal alcohol functions in the tetrahydrofuran ring, c) reaction of the primary alcohol function in the side chain of the substituted tetrahydrofuran with an alkyl halide, c) removing the protective groups from the two vicinal alcohol functions in the tetrahydrofuran ring, if these were introduced in step b), and d) subsequent sulfation using a sulfating agent and optionally neutralization by subsequent reaction with X + OH − , X + HCO − 3 or X + 2 CO 2− 3 , in which X + represents an alkali metal cation or a grouping N + R 3 R 4 R 5 , in which R 3 , R 4 and R 5 represent, independently of one another, hydrogen, an alkyl group having 1 to 6 carbon atoms, or a hydroxyalkyl group having 2 to 6 carbon atoms.

3. A washing or cleaning agent containing an anionic surfactant of the general formula (I),

in which R 1 and R 2 represent, independently of one another, H and SO 3 − X + , with the proviso that at least one of R 1 and R 2 is not H, n and m represent, independently of one another, numbers from 0 to 21, with the proviso that 4<n+m<26, and X + represents a charge-balancing cation.

4. The agent according to claim 3 , wherein the agent comprises 1 wt. % to 99 wt. % of the surfactant of general formula (I).

5. The agent according to claim 3 , wherein the agent further comprises up to 99 wt. % of additional surfactant.

6. The agent according to claim 3 , wherein the agent is particulate and comprises builders, or in that the agent is liquid and comprises 1 wt. % to 90 wt. % of water, water-miscible solvent or a mixture of water and water-miscible solvent.

7. The agent according to claim 3 , wherein the agent is portioned ready for individual dosing in a chamber made of water-soluble material and comprises less than 15 wt. % of water.

8. The surfactant according to claim 1 wherein the compounds of general formula (I), n and m represent, independently of one another, numbers from 0 to 17, the sum of n and m satisfies the inequality 4<n+m<20 and/or n represents a number from 0 to 4 and m represents a number from 5 to 14.

9. The agent according to claim 4 , wherein the agent comprises 3 wt. % to 65 wt. % of the surfactant of general formula (I).

10. The agent according to claim 5 , wherein the agent further comprises 3 wt. % to 65 wt. % of additional surfactant.

11. The agent according to claim 6 , wherein the agent comprises builders in an amount in the range of 1 wt. % to 60 wt. %, or in that the agent is liquid and comprises 10 wt. % to 85 wt. % of water, water-miscible solvent or a mixture of water and water-miscible solvent.

12. The agent according to claim 7 , wherein the water-soluble chamber comprises a range of 1 wt. % to 12 wt. %, of water.

13. The surfactant according to claim 8 , wherein the sum of n and m satisfies the inequality 6<n+m<18.

14. The method according to claim 2 , wherein the compounds of general formula (I), n and m represent, independently of one another, numbers from 0 to 17, the sum of n and m satisfies the inequality 4<n+m<20, and/or n represents a number from 0 to 4 and m represents a number from 5 to 14.

15. The agent according to claim 3 , wherein the compounds of general formula (I), n and m represent, independently of one another, numbers from 0 to 17, the sum of n and m satisfies the inequality 4<n+m<20, and/or n represents a number from 0 to 4 and m represents a number from 5 to 14.

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Kropf Christian
• Klemmer Anna
• Bedrunka Danuta
• Palkovits Regina
• Hausoul Peter
• Kipshagen Lukas
• Stobbe Carsten

Classifications

• C11D1/26 Primary

  derived from heterocyclic compounds · CPC title

• C11D17/043

  Liquid or thixotropic (gel) compositions · CPC title

• C11D3/2096 Primary

  Heterocyclic compounds · CPC title

• C11D1/29

  Sulfates of polyoxyalkylene ethers · CPC title

• C07D307/10 Primary

  with substituted hydrocarbon radicals attached to ring carbon atoms · CPC title