Washing or cleaning detergent containing wash-active ionic liquids

WO2026131222A1PCT designated stage Publication Date: 2026-06-25HENKEL KGAA

Patent Information

Authority / Receiving Office
WO · WO
Patent Type
Applications
Current Assignee / Owner
HENKEL KGAA
Filing Date
2025-12-08
Publication Date
2026-06-25

AI Technical Summary

Technical Problem

Conventional detergents and cleaning agents face challenges in achieving high washing performance with concentrated formulations, as alkali metal or ammonium ions do not contribute significantly to cleaning power, and there is a desire for further compaction while maintaining or improving cleaning efficacy, especially on greasy soils.

Method used

A neutralization product comprising linear alkylbenzenesulfonic acid (LAS) and ethoxylated fatty amine (EFA) in a molar ratio of 1:20 to 20:1, combined with surfactant polymers and/or complexing agents, enhances washing performance on greasy soils.

Benefits of technology

The LAS-EFA neutralization product, when used in washing agents, significantly improves cleaning efficacy on greasy soils, demonstrating enhanced performance in concentrated formulations.

✦ Generated by Eureka AI based on patent content.

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Abstract

A neutralization product consisting of at least one linear alkylbenzenesulfonic acid (LAS) and at least one ethoxylated fatty amine (EFA), in which LAS and EFA are present in a molar ratio of 1:20 to 20:1, and to a washing or cleaning detergent containing this neutralization product,
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Description

[0001] Henkel AG & Co. KGaA

[0002] Dr. Mundt

[0003] Washing or cleaning agents containing surfactant ionic liquids.

[0004] The present invention relates to a neutralization product consisting of at least one linear alkylbenzenesulfonic acid and at least one ethoxylated fatty amine in a molar ratio of 1:20 to 20:1, as well as washing or cleaning agents containing this neutralization product and a method for cleaning and / or caring for textiles using the washing and cleaning agents.

[0005] Concentrated detergents and cleaning agents are becoming increasingly important. Due to their smaller volume and the avoidance of ingredients that do not contribute to cleaning performance, such concentrates result in lower manufacturing, packaging, and transport costs, and therefore also have a smaller CO2 footprint than conventional detergents and cleaning agents.

[0006] The anionic surfactants conventionally used in detergents and cleaning agents are usually obtained by neutralizing the underlying acids with alkali metal hydroxides or organic alkanolamines such as monoethanolamine (MEA), monoisopropanolamine (MIPA), or triethanolamine (TEA). However, the alkali metal or ammonium ions do not contribute to the cleaning power. Therefore, to further increase the concentration, it is desirable to find surfactant counterions to the acid anions.

[0007] The international patent application WO 2024 / 012732 A1 describes washing-active compounds that are produced by the neutralization of anionic surfactant acids with fatty amine ethoxylates and can be used in concentrated washing and cleaning agents.

[0008] However, it is desirable to further compact washing and cleaning agents in order to achieve the same or improved washing performance with lower dosage.

[0009] Surprisingly, it was found that neutralization products consisting of at least one linear alkylbenzenesulfonic acid (LAS) and at least one ethoxylated fatty amine (EFA), in which LAS and EFA are present in a molar ratio of 1:20 to 20:1, exhibit particularly high washing performance, especially on greasy soils. In washing or cleaning agents that contain at least one surfactant polymer and / or at least one complexing agent in addition to these neutralization products, a further increase in performance against greasy and bleachable soils could be achieved.

[0010] A first subject matter of the application is therefore a neutralization product consisting of at least one linear alkylbenzenesulfonic acid (LAS) and at least one ethoxylated fatty amine (EFA), characterized in that LAS and EFA are present in a molar ratio of 1:20 to 20:1. 2024PF00317

[0011] 2

[0012] Another subject of this application is a washing or cleaning agent containing this neutralizing product.

[0013] In a preferred embodiment, the washing or cleaning agent contains at least one washing-active polymer.

[0014] In another preferred embodiment, the washing or cleaning agent contains at least one complexing agent.

[0015] These and other aspects, features, and advantages of the invention will become apparent to the person skilled in the art upon studying the following detailed description and claims. Each feature from one aspect of the invention can be incorporated into any other aspect of the invention. Furthermore, it is understood that the examples contained herein are intended to describe and illustrate the invention, but do not limit it, and in particular, the invention is not limited to these examples.

[0016] Unless otherwise stated, all percentages are weight percentages based on the total weight of the agent / composition.

[0017] Numeric ranges specified in the format "from x to y" include the stated values. If multiple preferred numeric ranges are specified in this format, it is understood that all ranges resulting from the combination of the different endpoints are also included.

[0018] “At least one,” as used herein, refers to 1, 2, 3, 4, 5, 6, 7, 8, 9, or more. In the context of components of the compositions described herein, this term refers not to the absolute quantity of molecules but to the type of component. “At least one anionic surfactant,” for example, means one or more different anionic surfactants, i.e., one or more different types of anionic surfactants. When used in conjunction with quantity specifications, the quantities refer to the total amount of the appropriately designated type of component.

[0019] The neutralization product according to the invention is formed by the neutralization reaction between at least one linear alkylbenzenesulfonic acid (LAS) and at least one ethoxylated fatty amine (EFA). 2024PF00317

[0020] 3

[0021] Linear alkylbenzenesulfonic acids are common anionic surfactant acids that typically have a Cs-22 alkyl chain, preferably a Ci2-20 alkyl chain, and particularly preferably a Ci2-18 alkyl chain.

[0022] Ethoxylated fatty amines (fatty amine ethoxylates) are amines comprising a long-chain saturated or unsaturated, straight-chain or branched alkyl group and two oligo- or polyethoxylate chains. Preferably used ethoxylated fatty amines conform to the general formula (I). where R 1for a linear or branched, preferably linear Cs-20 alkyl chain, preferably a linear C10-14 alkyl chain, particularly preferably a C12 alkyl chain, m and n each independently represent integers from 1 to 11, preferably 1 to 7, particularly preferably 1 to 4, and the sum of m + n is 2 to 12, preferably 3 to 8, particularly preferably 4 to 6, particularly 5. Suitable ethoxylated fatty amines are commercially available, for example, under the trade name Ethomeen.

[0023] The resulting neutralization product is a so-called ionic liquid. In the neutralization product, LAS and EFA are present in a molar ratio of 1:20 to 20:1, preferably in a molar ratio of 1:8 to 8:1.

[0024] Another object of the invention is a washing or cleaning agent containing the described neutralization product.

[0025] In a preferred embodiment, the washing or cleaning agent according to the invention may contain a non-ionic surfactant. Suitable non-ionic surfactants include, for example, fatty alcohol alkoxylates, alkoxylated fatty acid alkyl esters, fatty acid amides, alkoxylated fatty acid amides, polyhydroxy fatty acid amides, alkylphenol polyglycol ethers, amine oxides, alkyl polyglycosides, sophorolipids, mannosyl erythritol lipids, and mixtures thereof.

[0026] The non-ionic surfactants used are preferably alkoxylated, advantageously ethoxylated and / or propoxylated, preferably ethoxylated, in particular primary alcohols with preferably 8 to 22 carbon atoms and an average of 1 to 12 moles of ethylene oxide (EO) per mole of alcohol, in which the alcohol residue may be linear or preferably methyl-branched at the 2-position, or may contain linear and methyl-branched residues in the mixture, as shown in 2024PF00317

[0027] 4 are usually present in oxo alcohol residues. However, alcohol ethoxylates with linear residues from native alcohols with 12 to 18 carbon atoms, for example, from coconut, palm, tallow, or oleyl alcohol, and an average of 2 to 8 moles of ethoxylation per mole of alcohol, are particularly preferred. Preferred ethoxylated alcohols include, for example, Ci2-14 alcohols with 3 or 4 ethoxylation molecules, Cs-n alcohols with 7 ethoxylation molecules, C-is alcohols with 3, 5, 7, or 8 ethoxylation molecules, C12-18 alcohols with 3, 5, or 7 ethoxylation molecules, and mixtures thereof, such as mixtures of C12-14 alcohols with 3 ethoxylation molecules and Ci2-is alcohols with 5 ethoxylation molecules. Mixtures of fatty alcohol ethoxylates with different alkyl chain lengths and degrees of ethoxylation can also be used. Particularly favored representatives are fatty alcohols with 10 to 18 carbon atoms and with 7 EO.Such fatty alcohol ethoxylates are available under the trade names Dehydol® LT7 (BASF), Lutensol® AO7 (BASF), Lutensol® M7 (BASF) and Neodol® 45-7 (Shell Chemicals).

[0028] Overall, the washing or cleaning agent according to the invention preferably contains 20 to 85 wt.%, preferably 40 to 82 wt.% surfactants.

[0029] In addition to the surfactants mentioned so far, the washing or cleaning agent according to the invention can also contain surfactants from the group consisting of anionic surfactants, amphoteric or zwitterionic surfactants and mixtures thereof.

[0030] Examples of anionic surfactants that can be used in accordance with this application include linear or branched alkylbenzenesulfonates, fatty alcohol sulfates, alkyl ether sulfates, ether carboxylates, secondary alkanesulfonates, sulfosuccinates, taurides, isethionates or rhamnolipids.

[0031] Suitable zwitterionic or amphoteric surfactants include, for example, betaines, sulfobetaines or amphoacetates.

[0032] In a preferred embodiment, the washing or cleaning agent according to the invention contains at least one washing-active polymer.

[0033] Suitable washing-active polymers include, in particular, anti-greying polymers, dirt-removing polymers, color transfer inhibitors or anti-reposition agents.

[0034] The function of anti-graying agents is to keep the dirt detached from textile fibers suspended in the cleaning solution. Water-soluble colloids, mostly of organic origin, are suitable for this purpose; examples include starch, glue, gelatin, salts of ether carboxylic acids or ether sulfonic acids (see 2024PF00317).

[0035] 5

[0036] Starch or cellulose, or salts of acidic sulfuric acid esters of cellulose or starch, are suitable. Water-soluble polyamides containing acidic groups are also suitable for this purpose. Furthermore, starch derivatives other than those mentioned above can be used, for example, aldehyde starches. Cellulose ethers, such as carboxymethylcellulose (sodium salt), methylcellulose, hydroxyalkylcellulose, and mixed ethers, such as methylhydroxyethylcellulose, methylhydroxypropylcellulose, methylcarboxymethylcellulose, and mixtures thereof, are preferred.

[0037] Furthermore, the product may contain dirt-removing polymers or soil release polymers (SRPs). Suitable dirt-removing polymers are generally already sufficiently known from the prior art. In particular, all polymers known from the prior art for this purpose can be used. SRPs that can be used include, in particular, oligoesters available from, preferably, terephthalic acid, isophthalic acid, sulfoisophthalic acid and / or their methyl esters, aliphatic dicarboxylic acids (saturated and / or unsaturated), for example, adipic acid, and / or their anhydrides, aliphatic substituted dicarboxylic acids, for example, nonyl succinic acid, alkylene glycols (ethylene, 1,2-propylene, 1,2-butylene glycol), polyethylene glycols, alkyl polyethylene glycols, polyethylene glycol sulfobenzoic acid esters, and optionally alkanolamines.Preferred polymers are those based on terephthalate-PEG, such as those commercially available under the trade name Texcare®. Alternatively, (co)polymers based on polyethyleneimine, polyvinyl acetate, and polyethylene glycol can also be used.

[0038] Preferably, the washing or cleaning agent may contain ethoxylated polyethyleneimine in an amount of up to 85% by weight, preferably up to 60% by weight, particularly preferably up to 40% by weight, and especially up to 20% by weight. A preferred ethoxylated polyethyleneimine is commercially available under the trade name Sokalan® HP20.

[0039] In a further preferred embodiment, the washing or cleaning agent according to the invention contains soil-release polymers in an amount of 5 to 65 wt.%, preferably 5 to 40 wt.%, particularly preferably 5 to 20 wt.%.

[0040] To effectively suppress dye transfer and / or dye transfer to other textiles during washing and / or cleaning of dyed textiles, the composition according to the invention can contain a dye transfer inhibitor (DTI). It is preferred that the dye transfer inhibitor is a polymer or copolymer of cyclic amines such as vinylpyrrolidone and / or vinylimidazole. Suitable polymers include polyvinylpyrrolidone (PVP), polyvinylimidazole (PVI), copolymers of 2024PF00317

[0041] 6

[0042] Vinylpyrrolidone and vinylimidazole (PVP / PVI), polyvinylpyridine N-oxide, poly-N-carboxymethyl-4-vinyl ipyridium chloride, and mixtures thereof. Polyvinylpyrrolidone (PVP), polyvinylimidazole (PVI), or copolymers of vinylpyrrolidone and vinylimidazole (PVP / PVI) are particularly preferred as color transfer inhibitors.

[0043] Polycarboxylates are particularly suitable as anti-reposition agents. Appropriate materials can be prepared by the polymerization or copolymerization of unsaturated carboxylic acid monomers, such as acrylic acid, maleic acid (or anhydride), fumaric acid, itaconic acid, aconitic acid, mesaconic acid, citraconic acid, and methylmalonic acid. Acrylate polymers and acrylic / maleic acid copolymers are especially preferred.

[0044] In a further preferred embodiment, the washing or cleaning agent according to the invention contains at least one complexing agent. Any complexing agent known to the trade can be used as such. Preferred complexing agents include phosphonates, in particular diethylenetriaminepenta(methylenephosphonic acid) (DTPMP) or its sodium salts, which are commercially available under the trade name Dequest.

[0045] Preferably, the washing or cleaning agent according to the invention further contains at least one enzyme. In principle, all enzymes established in the prior art for this purpose can be used. Preferably, this includes one or more enzymes that can exhibit catalytic activity in a washing agent, in particular a protease, amylase, lipase, cellulase, hemicellulase, mannanase, pectin-splitting enzyme, tannase, xylanase, xanthanase, β-glucosidase, carrageenase, perhydrolase, oxidase, oxidoreductase, hexosaminidase, and mixtures thereof. Preferred hydrolytic enzymes include, in particular, proteases, amylases (especially α-amylases), cellulases, lipases, hemicellulases (especially pectinases), mannanases, β-glucanases, and mixtures thereof. Enzymes selected from the group comprising amylases, proteases, cellulases, mannanases and lipases, as well as mixtures thereof, are particularly preferred.These enzymes are essentially of natural origin; based on the natural molecules, improved versions are available for use in detergents and are therefore preferred. The enzymes can be adsorbed onto carrier substances and / or embedded in coating materials to protect them against premature inactivation. The enzymes used can also be combined with accompanying substances, such as those from fermentation, or with stabilizers.

[0046] Preferably, the at least one enzyme is present in an amount of 1 to 15 wt.%, particularly preferably 5 to 15 wt.%. 2024PF00317

[0047] 7

[0048] In addition, the washing or cleaning agent according to the invention can contain at least one further active ingredient, preferably selected from the group comprising builders, bleaching agents, bleach activators, electrolytes, pH adjusters, perfumes, perfume carriers, fluorescent agents, dyes, foam inhibitors, scrunching agents, anti-crease agents, antioxidants, corrosion inhibitors, antistatic agents, bittering agents, ironing aids, antiphobing and impregnating agents, skin conditioning agents, swelling and slip-resistant agents, plasticizing components and UV absorbers.

[0049] Another object of the invention is a method for cleaning and / or caring for textiles comprising the process steps: a) providing a washing solution comprising a washing or cleaning agent according to the invention, b) bringing a textile into contact with the washing solution according to a).

[0050] 2024PF00317

[0051] 8

[0052] Examples

[0053] Six different formulations were produced, the compositions of which can be found in the following table. The quantities are given in wt.%.

[0054] Washing tests were conducted on 43 stains using each of these six formulations in a Miele W1714 washing machine, using the standard 40°C program and a 3.5 kg load. The whiteness levels, so-called Y-values, were then determined. The higher the Y-value, the better the washing performance. The results are also shown in the table.

[0055] 1 : Ethomeen C15

[0056] 2: Dehydol LT7

[0057] 3: Sokalan HP20

[0058] 4: Texcare SRN 170

[0059] 5: Dequest 2066C

[0060] 6: Plurafac LF 1430

[0061] Examples A and B demonstrate the influence of the surfactant ratio. Examples C and D show the improvement in washing performance when using complexing agents, and examples E and F document the effect of the surfactant polymers.

Claims

2024PF00317 9 Patent claims:

1. Neutralization product of at least one linear alkylbenzenesulfonic acid (LAS) and at least one ethoxylated fatty amine (EFA), characterized in that LAS and EFA are present in a molar ratio of 1:20 to 20:

1.

2. Neutralization product according to claim 1, characterized in that the ethoxylated fatty amine obeys the general formula (I), where R 1 for a linear or branched, preferably linear Cs-20 alkyl chain, preferably a linear C 10-14 alkyl chain, particularly preferably a C12 alkyl chain, m and n each independently of each other represent integers from 1 to 11, preferably 1 to 7, particularly preferably 1 to 4 and the sum of m + n is 2 to 12, preferably 3 to 8, particularly preferably 4 to 6, in particular 5.

3. Neutralization product according to one of claims 1 or 2, characterized in that the molar ratio of LAS and EFA is 1:8 to 8:

1.

4. Washing or cleaning agent containing the neutralizing product according to any one of claims 1 to 3.

5. Washing or cleaning agent according to claim 4, characterized in that it contains at least one non-ionic surfactant.

6. Washing or cleaning agent according to one of claims 4 or 5, characterized in that it contains a total of 20 to 85 wt.%, preferably 40 to 82 wt.% surfactants.

7. Washing or cleaning agent according to one of claims 4 to 6, characterized in that it contains at least one washing-active polymer.

8. Washing or cleaning agent according to claim 7, characterized in that it contains ethoxylated polyethyleneimine in an amount of up to 85 wt.%, preferably up to 60 wt.%, particularly preferably up to 40 wt.%, and in particular up to 20 wt.%. 2024PF00317 10 9. Washing or cleaning agent according to one of claims 7 or 8, characterized in that it contains soil-release polymers in an amount of 5 to 65 wt.%, preferably 5 to 40 wt.%, particularly preferably 5 to 20 wt.%.

10. Washing or cleaning agent according to any one of claims 4 to 9, characterized in that it contains at least one complexing agent.

11. Washing or cleaning agent according to any one of claims 4 to 10, characterized in that it contains at least one enzyme, preferably in an amount of 1 to 15 wt.%, particularly preferably 5 to 15 wt.%.

12. Washing or cleaning agent according to any one of claims 4 to 11, characterized in that it contains at least one further active ingredient, preferably selected from the group comprising builders, bleaching agents, bleach activators, electrolytes, pH adjusters, perfumes, perfume carriers, fluorescent agents, dyes, foam inhibitors, scrunching agents, anti-crease agents, antioxidants, corrosion inhibitors, antistatic agents, bittering agents, ironing aids, antiphobing and impregnating agents, skin conditioning agents, swelling and slip-resistant agents, plasticizing components and UV absorbers.

13. Method for cleaning and / or caring for textiles comprising the process steps: a) providing a washing solution comprising a washing or cleaning agent according to any one of claims 4 to 12, b) bringing a textile into contact with the washing solution according to a).