Wash-active compounds based on a combination of anions and cationic detergent

Abstract

The invention relates to a compound of the general formula (1) wherein i) R is selected from the group of the C6 to C20 alkyl groups; ii) X is selected from the group a) C6H4, b) (OC2H4)nO with n = 1 to 8, c) C(O)-N(CH3)CH2CH2, d) O(O)CCH2(RO(O)C)CH with R = C6 to C20 alkyl, iii) R2 selected from the group of the C6 to C20 alkyl groups, iv) with m + n = 5 to 12, to detergents or cleaning agents that contain this compound, and to processes for preparing the compound.

Description

[0001] "Detergent compounds based on a combination of anions and cationic surfactants." The present invention relates to a detergent compound with enhanced washing performance on greasy stains. Furthermore, the application relates to detergents and cleaning agents containing this detergent compound, processes for producing the detergent compound, and washing and cleaning processes using the detergent compound. Continuously changing demands are placed on the packaging and presentation of detergents and cleaning agents. A relevant trend in the production of detergents and cleaning agents is their concentration. The background to this development is not only greater consumer acceptance due to simplified handling, but also, in particular, sustainability aspects, for example with regard to transport volumes and costs and the amount of packaging used.In concentrated detergents and cleaning agents, the anionic surfactant acids are usually present in a form neutralized by organic alkanolamines such as monoethanolamine (MEA), monoisopropanolamine (MIPA), or triethanolamine (TEA). However, the ammonium ions resulting from the neutralization reaction do not contribute to the washing performance. Against this background, the application was based on the objective of providing washing and cleaning active ingredients that enable the production of visually appealing, concentrated, flowable detergent formulations. The active ingredients should be simple and efficient to produce, exhibit good storage stability, and be characterized, in particular, by good cleaning results, for example, on greasy soils.It was surprisingly found that the neutralization products of anionic surfactant acids with fatty amine ethoxylates of suitable ethylene oxide chain length exhibit detergent compounds with outstandingly high washing performance on greasy soils. Furthermore, it was found that the washing performance of detergent compositions containing these neutralization products does not necessarily require the addition of further surfactants, such as nonionic surfactants, due to their good washing performance. International patent application WO 2017 / 205915 A1 describes an aqueous cleaning composition containing silicates, ethoxylated alcohols, quaternary fatty amine ethoxylates, and a urea salt. European patent EP 0231886 B1 describes fatty amine ethoxylates as solubilizers in cleaning concentrates for cleaning solutions for bottle cleaning.A first subject matter of this application is a compound of the general formula (1) RX-SO3-. i) R is selected from the group of C6 to C 20 -alkyl radicals; ii) X is selected from the group a) C6H4b) (OC2H4) n O with n = 1 to 8 c) C(O)-N(CH3)CH2CH2d) O(O)CCH2(RO(O)C)CH with R = C6- to C 20 -Alkyl iii) R2is selected from the group of C6 to C 20-Alkyl radicals iv) with m + n = 5 to 12. Surprisingly, it has been found that by neutralizing specific anionic surfactant acids containing sulfonic acid groups with the above-mentioned fatty amine ethoxylates, surface-active substances can be obtained which are suitable, for example, for the production of solvent-free liquid detergents with active ingredient contents of up to 100% by weight. Furthermore, it has been found that the neutralization products of anionic surfactant acids containing sulfonic acid groups with the above-mentioned fatty amine ethoxylates are distinguished from conventional detergent compounds, for example the neutralization products of anionic surfactant acids containing sulfonic acid groups with alkanolamines, by an increased reduction in the interfacial tension of water and improved grease removal. A particularly preferred compound of general formula (1) is based on anionic surfactants from the group of alkylbenzenesulfonic acids.Particularly preferred compounds of the general formula (1) are therefore characterized in that i) R is selected from the group of C. 10 - to C 14 -alkyl radicals; ii) X is selected from the group C6H4iii) R2 is selected from the group of C6 to C 20 -alkyl radicals, preferably C 10 to C 16 -Alkyl radicals iv) with m + n = 5 to 12. R radicals selected from the group of linear C 10 - to C 14 - Alkyl radicals of the secondary C 10 - to C 14 -alkyl radicals and in particular the linear secondary C 10 - to C 14 -alkyl radicals. R radicals from the group of linear C 12 H 25 -alkyl radicals, especially the linear secondary C 12 H 25-alkyl radicals. In alternative embodiments, the sulfonic acid underlying the compound of general formula (1) can be varied. A first alternative is formed by compounds of general formula (1), wherein i) R is selected from the group of C 12 - to C 20 -alkyl radicals; ii) X is selected from the group selected from the group (OC2H4) n O with n = 1 to 8 iii) R2is selected from the group of C6 to C 20 -Alkyl radicals iv) with m + n = 5 to 12 A further alternative comprises compounds of the general formula (1), where i) R is selected from the group of C6 to C 20 -alkyl radicals; ii) X is selected from the group C(O)-N(CH3)CH2CH2; iii) R2 is selected from the group of C6 to C 20 -Alkyl radicals iv) with m + n = 5 to 12 The third alternative is represented by compounds of the general formula (1), where i) R is selected from the group of C7 to C 17-alkyl radicals; ii) X is selected from the group O(O)CCH2(RO(O)C)CH with R = C6- to C17-alkyl; iii) R2 is selected from the group of C6- to C 20-Alkyl radicals iv) with m + n = 5 to 12 In addition to the anionic surfactant acids containing sulfonic acid groups, the compounds of the general formula (1) also include specific fatty amine ethoxylates. The ethoxylated side chains characteristic of the fatty amine ethoxylates can have a degree of ethoxylation of m + n = 5 to 12. For example, the degree of ethoxylation can be m + n = 5 or m + n = 6 or m + n = 7 or m + n = 8 or m + n = 9 or m + n = 10 or m + n = 11 or m + n = 12. Particular preference is given to compounds of the general formula (1) with m + n = 5 or 6. The degree of ethoxylation of the two ethoxylated side chains can be the same or different. Due to their easier preparation, fatty amine ethoxylates with the same degree of ethoxylation of the side chains are preferred. In a particularly preferred compound of general formula (1), i) R represents a linear secondary C 12 H 25-alkyl radical; ii) X is selected from the group C6H4iii) R2is selected from the group C 12 H 25 -Alkyl radicals iv) m + n = 5 or 6 In particular, the neutralization products of alkylbenzenesulfonic acid-based anionic surfactant acids with the above-mentioned fatty amine ethoxylates are distinguished from conventional detergent compounds, for example the neutralization products of alkylbenzenesulfonic acid-based anionic surfactant acids with alkanolamines, by an increased reduction in the interfacial tension of water and improved grease cleaning. Some preferred compounds of the general formula (1) with i) R is selected from the group of C6 to C 20 -alkyl radicals; ii) X is selected from the group a) C6H4b) (OC2H4)nO with n = 1 to 8 c) C(O)-N(CH3)CH2CH2d) O(O)CCH2(RO(O)C)CH with R = C6- to C 20 -Alkyl iii) R2is selected from the group of C6 to C 20-Alkyl radicals iv) with m + n = 5 to 12. can be found in the following tables: Table a:

[0002] Table b:

[0003] Table c:

[0004] Table d:

[0005] As stated above, the compounds of general formula (1) are particularly suitable as components of detergents or cleaning agents, in particular liquid detergents or cleaning agents, due to their physical properties. Corresponding detergents or cleaning agents containing a compound of general formula (1) are therefore further subject matter of this application. A detergent is a composition suitable for cleaning or caring for textiles and containing at least one textile-cleaning or textile-care active ingredient.Examples of textile cleaning active ingredients are: - surfactants, in particular nonionic or anionic surfactants, - builders, such as phosphonates or water-softening polymers. Examples of textile care active ingredients are: - fragrances, in particular encapsulated fragrances, - fabric softeners, in particular cationic surfactants and cationic polymers, - enzymes, in particular proteases, amylases, lipases, and cellulases, - dyes, in particular textile dyes. The detergents are preferably free from fluorinated hydrocarbon solvents. The application further relates to a process for washing textiles, in the course of which a compound of general formula (1) or a detergent containing a compound of general formula (1) is introduced into a wash liquor. The wash liquor is preferably aqueous and free from fluorinated hydrocarbon solvents.A cleaning agent is a composition suitable for cleaning and caring for hard surfaces and containing at least one surface-cleaning or surface-care active ingredient. Examples of surface-cleaning active ingredients are: - surfactants, especially nonionic or anionic surfactants; - builders, such as phosphonates or water-softening polymers; - corrosion inhibitors, especially zinc salts; - hydrophobicizing agents, especially polymeric hydrophobicizing agents. The cleaning agents are preferably free of fluorine-containing hydrocarbon solvents. A process for cleaning surfaces, in the course of which a compound of general formula (1) or a cleaning agent containing a compound of general formula (1) is introduced into a cleaning liquor, is an additional subject matter of this application.The cleaning solution is preferably aqueous and free of fluorinated hydrocarbon solvents. The composition of some preferred detergents or cleaning agents can be found in the following tables (data in wt. % based on the total weight of the preparation unless otherwise stated). The detergents or cleaning agents listed are free of fluorinated hydrocarbon solvents.

[0006] The preparation of compounds of general formula (1) can be carried out by neutralizing a corresponding sulfonic acid with the respective amine. A process for preparing a compound of general formula (1) according to any one of items 1 to 12, comprising the steps of 1) providing a sulfonic acid (2) of general formula RX-SO3H, where i) R is selected from the group of C6 to C 20 -alkyl radicals; ii) X is selected from the group a) C6H4b) (OC2H4)n O with n = 2 to 8 c) C(O)-N(CH3)CH2CH2d) O(O)CCH2(RO(O)C)CH with R = C6- to C 20 -Alkyl 2) Providing an amine (3) of the general formula with i) R2selected from the group of C6 to C 20-Alkyl radicals ii) m + n = 5 to 12. 3) Mixing the anionic surfactant (2) and the amine (3) to form an ionic compound of the general formula (1). is a further subject of this application. Compounds of the general formula (1) can, as described above, be prepared by reacting a sulfonic acid (2) with a corresponding tertiary amine (3). In other words, preferred detergents based on compounds of the general formula (1) can be described by their content of sulfonic acid (2) and tertiary amine (3). The composition of some preferred detergents or cleaning agents can be found in the following tables (data in wt. % based on the total weight of the preparation unless otherwise stated). The detergents or cleaning agents mentioned are free from fluorine-containing hydrocarbon solvents.

[0007] 1 X is selected from the group a) C6H4b) (OC2H4) n O with n = 1 to 8 c) C(O)-N(CH3)CH2CH2d) O(O)CCH2(RO(O)C)CH with R = C6- to C 20 -Alkyl; preferably from C6H4. The compounds of general formula (1) are particularly suitable for the production of detergent compositions with a high surfactant content. In addition to their high content of sulfonic acid (2) neutralized with tertiary amine (3), these compositions are also characterized in particular by a low solvent content. The composition of some preferred highly concentrated detergents or cleaning agents can be found in the following tables (data in wt. % based on the total weight of the preparation unless otherwise stated). The detergents or cleaning agents listed are free of fluorinated hydrocarbon solvents.

[0008] 2 X is selected from the group a) C6H4b) (OC2H4)nO with n = 1 to 8 c) C(O)-N(CH3)CH2CH2d) O(O)CCH2(RO(O)C)CH with R = C6- to C 20 -Alkyl; preferably from C6H4. The washing or cleaning agents described above are preferably free of quaternary amines and organic pigments. This application provides, among other things, the following objects: 1. A compound of the general formula (1) RX-SO3- i) R is selected from the group of C6 to C 20 -alkyl radicals; ii) X is selected from the group e) C6H4f) (OC2H4) n O with n = 1 to 8 g) C(O)-N(CH3)CH2CH2h) O(O)CCH2(RO(O)C)CH with R = C6- to C 20 -alkyl; iii) R2is selected from the group of C6 to C 20 -alkyl radicals; iv) with m + n = 5 to 12. 2. A compound of the general formula (1) according to point 1, wherein i) R is selected from the group of C 10 - to C 14-alkyl radicals; ii) X is selected from the group C6H4; iii) R2 is selected from the group of C6 to C 20 -alkyl radicals, preferably C 10 - to C16-alkyl radicals iv) with m + n = 5 to 12. 3. Compound of the general formula (1) according to point 2, where i) R is selected from the group of linear C 10 - to C 14 -alkyl radicals. 4. A compound of the general formula (1) according to any one of points 2 or 3, wherein i) R is selected from the group of secondary C 10 - to C 14 -alkyl radicals. 5. A compound of the general formula (1) according to any one of points 2 to 4, wherein i) R is selected from the group of linear secondary C 10 - to C 14 -alkyl radicals. 6. A compound of the general formula (1) according to any one of items 2 to 5, wherein i) R is a linear C 12 H 25 -alkyl radical. 7. A compound of general formula (1) according to any one of items 2 to 6, wherein i) R is a linear secondary C 12 H25 -alkyl radical. 8. A compound of general formula (1) according to point 1, wherein i) R is selected from the group of C 12 - to C 20 -alkyl radicals; ii) X is selected from the group (OC2H4)nO with n = 1 to 8; iii) R2 is selected from the group of C6 to C 20 -alkyl radicals; iv) with m + n = 5 to 12. 9. A compound of the general formula (1) according to point 1, wherein i) R is selected from the group of C6 to C 20 -alkyl radicals; ii) X is selected from the group C(O)-N(CH3)CH2CH2; iii) R2 is selected from the group of C6 to C 20 -alkyl radicals; iv) with m + n = 5 to 12. 10. A compound of the general formula (1) according to point 1, wherein i) R is selected from the group of C7- to C17-alkyl radicals; ii) X is selected from the group O(O)CCH2(RO(O)C)CH with R = C6- to C 17 -alkyl; iii) R2is selected from the group of C6 to C 20-alkyl radicals; iv) with m + n = 5 to 12 11. Compound of the general formula (1) according to any one of points 1 to 10, iv) with m + n = 5 or 6 12. Compound of the general formula (1) according to point 1, where i) R is a linear secondary C 12 H 25 -alkyl radical; ii) X is selected from the group C6H4iii) R2is selected from the group C 12 H 25-Alkyl radicals iv) m + n = 5 or 6 13. Washing or cleaning agent containing a compound of the general formula (1) according to any one of the preceding points. 14. Washing or cleaning agent according to point 13, wherein the washing or cleaning agent is free of fluorinated hydrocarbon solvents. 15. A process for washing textiles, in the course of which a compound of the general formula (1) according to any one of the preceding points 1 to 12 or a washing or cleaning agent according to point 13 is introduced into a washing liquor. 16. A process according to point 15, wherein the washing liquor is free of fluorinated hydrocarbon solvents. 17. A process according to any one of points 15 or 16, wherein the washing liquor is aqueous. 18. A process for cleaning surfaces, in the course of which a compound of the general formula (1) according to any one of the preceding points 1 to 12 is introduced into a cleaning liquor. 19.Process according to item 18, wherein the cleaning liquor is free of fluorine-containing hydrocarbon solvents. 20. Process according to either item 18 or 19, wherein the cleaning liquor is aqueous. 21. Process for preparing a compound of general formula (1) according to any one of items 1 to 12, comprising the steps of 1) providing a sulfonic acid (2) of general formula RX-SO3H, where i) R is selected from the group consisting of C6 to C12. 20 -alkyl radicals; ii) X is selected from the group a) C6H4b) (OC2H4) n O with n = 2 to 8 c) C(O)-N(CH3)CH2CH2d) O(O)CCH2(RO(O)C)CH with R = C6- to C 20 -Alkyl 2) Providing an amine (3) of the general formula with iii) R2 selected from the group of C6 to C 20-Alkyl radicals iv) m + n = 5 to 12. Mixing the anionic surfactant (2) and the amine (3) to form an ionic compound of the general formula (1). Examples The following detergents were provided: Table 1: Detergent compositions (wt%) 1 amine (3) with R2 selected from the group of C 12 - to C 18 -alkyl radicals and m + n = 5 The detergent compositions are characterized by above-average washing performance and a viscous-pasty consistency which is advantageous for processing and dosing.

Claims

Claims:

1. Compound of general formula (1) i) R is selected from the group of C6 to C 20 -alkyl radicals; ii) X is selected from the group a) C6H4b) (OC2H4)nO with n = 1 to 8 c) C(O)-N(CH3)CH2CH2d) O(O)CCH2(RO(O)C)CH with R = C6- to C 20 -Alkyl iii) R2is selected from the group of C6 to C 20 -Alkyl radicals iv) with m + n = 5 to 12.

2. A compound of the general formula (1) according to claim 1, wherein i) R is selected from the group of C 10 - to C 14 -alkyl radicals; ii) X is selected from the group C6H4iii) R2 is selected from the group of C6 to C 20 -alkyl radicals, preferably C 10 to C 16 -Alkyl radicals iv) with m + n = 5 to 12.

3. A compound of the general formula (1) according to any one of claims 1 or 2, wherein i) R is a linear secondary C 12 H 25-alkyl radical; ii) X is selected from the group C6H4iii) R2 is selected from the group C 12 H 25 -alkyl radicals iv) m + n = 5 or 6 4. A compound of the general formula (1) according to claim 1, wherein i) R is selected from the group of C 12 - to C 20 -alkyl radicals; ii) X is selected from the group selected from the group (OC2H4) n O with n = 1 to 8 iii) R2is selected from the group of C6 to C 20 -Alkyl radicals iv) with m + n = 5 to 12 5. A compound of general formula (1) according to claim 1, wherein i) R is selected from the group of C6 to C 20 -alkyl radicals; ii) X is selected from the group C(O)-N(CH3)CH2CH2; iii) R2 is selected from the group of C6 to C 20 -Alkyl radicals iv) with m + n = 5 to 12 6. Compound of the general formula (1) according to claim 1, wherein i) R is selected from the group of C7 to C 17-alkyl radicals; ii) X is selected from the group O(O)CCH2(RO(O)C)CH with R = C6- to C17-alkyl; iii) R2 is selected from the group of C6- to C 20 -Alkyl radicals iv) with m + n = 5 to 12 7. A compound of the general formula (1) according to any one of claims 1 to 6, iv) with m + n = 5 or 6 8. A washing or cleaning agent containing a compound of the general formula (1) according to any one of the preceding claims.

9. A process for washing textiles, in the course of which a compound of the general formula (1) according to any one of claims 1 to 7 or a washing or cleaning agent according to claim 8 is introduced into a wash liquor.

10. A process for preparing a compound of the general formula (1) according to any one of claims 1 to 7, comprising the steps of 1) providing a sulfonic acid (2) of the general formula RX-SO3H, where i) R is selected from the group of C6 to C 20-alkyl radicals; ii) X is selected from the group a) C6H4b) (OC2H4)nO with n = 2 to 8 c) C(O)-N(CH3)CH2CH2d) O(O)CCH2(RO(O)C)CH with R = C6- to C 20 -Alkyl 2) Providing an amine (3) of the general formula with iii) R2 selected from the group of C6 to C 20 -Alkyl radicals iv) m + n = 5 to 12. 3) Mixing the anionic surfactant (2) and the amine (3) to form an ionic compound of the general formula (1).

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