Wash-active compounds

Abstract

The invention relates to a compound of the general formula (1) R-X-SO3 - HN+(RaRbRc) (1), where i) R is selected from the group of C6- to C20-alkyl groups; ii) X is selected from the group a) C6H4, b) (OC2H4)nO, in which n = 2 to 8, c) C(O)-N(CH3)CH2CH2, and d) R1O(O)CCH2(R1O(O)C)CH, in which R1 = C6- to C20-alkyl iii) at least two of the groups Ra, Rb, and Rc are selected independently of each other from the group consisting of C3- to C12-alkyl- and C3- to C12-hydroxyalkyl groups. The invention also relates to detergents containing said compound, to washing and cleaning methods used said compound, and to methods for producing same.

Description

[0001] "Wash-active compounds" The present invention relates to a wash-active compound. Furthermore, the application relates to washing and cleaning agents containing this wash-active compound, processes for producing the wash-active compound, and washing and cleaning processes using the wash-active compound. Continuously changing requirements are placed on the packaging and presentation of washing and cleaning agents. A relevant trend for the production of washing 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.The concentration of modern detergents and cleaning agents, especially modern liquid detergents, generally influences their optical and rheological properties, impacts their storage stability, and can impair their cleaning performance, especially if the high concentration of active ingredients leads to incompatibilities. Furthermore, the concentration of detergents and cleaning agents is usually associated with the use of organic solvents. These solvents improve the physical stability of detergents and cleaning agents, but are often characterized by only low washing or cleaning activity, which is why their addition should be made in the smallest possible quantities, not least for sustainability reasons.However, the use of aqueous or aqueous-organic solvent systems in the production of concentrated liquid detergents has so far been unavoidable with conventional detergent or cleaning agents. European patent application EP 3670638 A1 describes the use of ionic liquids in combination with conventional aqueous or aqueous-organic solvent systems as a component of detergents or cleaning agents. US patent US 7,737,102 B2 describes detergent-active ionic liquids based on a combination of anionic surfactants and specific amine oxides. The objective of the application was to provide detergent and cleaning agents that enable the production of visually appealing, concentrated, flowable detergent preparations.The active ingredients should be simple and efficient to produce, exhibit good storage stability, and, in particular, be characterized by good cleaning results. This task was solved by a new class of surfactant active ingredients. The first subject of the application is a compound of the general formula (1) RX-SO3-HN. + (R a R b R c ) (1), 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) R 1 O(O)CCH2(R 1 O(O)C)CH with R 1 = C6- to C 20 -Alkyl iii) at least two of the radicals R a , R b and R c are independently selected from the group of C3 to C 12 -alkyl and C3- to C 12-hydroxyalkyl radicals. Surprisingly, it has been found that surface-active ionic liquids can be obtained by neutralizing specific anionic surfactant acids containing sulfonic acid groups with di- or tri-alkyl or -hydroxyalkylamines. The amorphous, transparent liquids are suitable, for example, for the production of solvent-free liquid detergents with active ingredient contents of up to 100% by weight. A particularly preferred compound of the 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 13 -alkyl radicals; ii) X is selected from the group C6H4iii) at least two of the radicals R a , R b and R c are independently selected from the group of C3 to C 12 -alkyl and C3- to C 12-hydroxyalkyl radicals. R radicals selected from the group of linear C 10 - to C 13 - Alkyl radicals of the secondary C 10 - to C 13 -alkyl radicals and in particular the linear secondary C 10 - to C 13 -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 (OC2H4)nO with n = 1 to 8 iii) at least two of the radicals R a , R b and R care independently selected from the group of C3 to C 12 -alkyl and C3- to C 12 -hydroxyalkyl radicals. A further alternative comprises compounds of the general formula (1), wherein i) R is selected from the group of C7 to C 17 -alkyl radicals; ii) X is selected from the group C(O)-N(CH3)CH2CH2; iii) at least two of the radicals R a , R b and R c are independently selected from the group of C3 to C 12 -alkyl and C3- to C 12 -hydroxyalkyl radicals. 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 C 17 -alkyl; iii) at least two of the radicals R a , R b and R c are independently selected from the group of C3 to C 12 -alkyl and C3- to C 12-hydroxyalkyl radicals. In addition to the sulfonic acid group-containing anionic surfactant acids, the compounds of the general formula (1) further comprise specific di- or tri-alkyl or -hydroxyalkylamines. In a first embodiment, at least two of the radicals R a , R b and R c are independently selected from the group of C3 to C 12 -Alkyl radicals, preferably from the group of C3 to C6 alkyl radicals. Particularly preferred are those compounds of the general formula (1) in which the three radicals R a , R b and R c are independently selected from the group of C3 to C 12 -Alkyl radicals, preferably from the group of C3- to C6-alkyl radicals. Some preferred compounds of the general formula RX-SO3- HN + ( R a R b R c ) with X selected from the group a) C6H4b) (OC2H4) nO with n = 1 to 8 c) C(O)-N(CH3)CH2CH2d) O(O)CCH2(R 1 O(O)C)CH with R 1 = C6- to C 20 -Alkyl can be found in the following table: In a second embodiment, at least two of the radicals R a , R b and R c are independently selected from the group of C3 to C 12 -Hydroxyalkyl radicals, preferably from the group of C3- to C6-hydroxyalkyl radicals. Particularly preferred are compounds of the general formula (1) in which the three radicals R a , R b and R c are independently selected from the group of C3 to C 12 -hydroxyalkyl radicals, preferably from the group of C3- to C6-hydroxyalkyl radicals. Compounds of the general formula (1) in which the three radicals R a , R b and R ceach represents a (CH2CH(OH)CH3)-hydroxyalkyl radical. Very particular preference is given to a compound of the general formula (1) in which i) R represents a linear C 12 H 25 -alkyl radical, preferably a linear secondary C 12 H 25 - alkyl radical; ii) X is selected from the group C6H4iii) R a , R b and R c each represent a (CH2CH(OH)CH3)-hydroxyalkyl radical. Some particularly preferred compounds of the general formula RX-SO3- HN + (R a R b R c ) with X selected from the group a) C6H4b) (OC2H4) n O with n = 1 to 8 c) C(O)-N(CH3)CH2CH2d) O(O)CCH2(R 1 O(O)C)CH with R 1 = C6- to C 20 -Alkyl can be found in the following table:

[0002] Most preferred is a compound of formula C 12 H 25 -C6H4-SO3-HN +(CH2CH(OH)CH3)3. 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, - dyes, in particular textile dyes. The detergents are preferably free of 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 of 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 liquid 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. A process for cleaning surfaces, in the course of which a compound of the general formula (1) or a cleaning agent containing a compound of the general formula (1) is introduced into a cleaning liquor, is an additional subject of this application. The preparation of compounds of the general formula (1) can be carried out by neutralizing a corresponding sulfonic acid with the respective amine. A process for preparing a compound of the general formula (1), comprising the steps of 1) providing a sulfonic acid of the general formula RX-SO3H (2), 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) R 1 O(O)CCH2(R 1 O(O)C)CH with R 1 = C7- to C20-alkyl 2) Providing an amine of the general formula N(R a R b R c) (3), where at least two of the radicals R a , R b and R c are selected from the group of C3 to C 12 -alkyl and C3- to C 12-hydroxyalkyl radicals; 3) Mixing the sulfonic acid (2) and the amine (3) to form a 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 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 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. 1X is selected from the group a) C6H4b) (OC2H4)nO with n = 2 to 8 c) C(O)-N(CH3)CH2CH2d) R 1 O(O)CCH2(R 1 O(O)C)CH with R 1 = C7- 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 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. 2 X is selected from the group a) C6H4 b) (OC2H4) n O with n = 2 to 8 c) C(O)-N(CH3)CH2CH2d) R 1 O(O)CCH2(R 1 O(O)C)CH with R 1 = C7- 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: 1. Compound of the general formula (1) RX-SO3- HN + (R a R b R c ) (1), 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) R 1 O(O)CCH2(R 1 O(O)C)CH with R 1 = C6- to C 20 -Alkyl iii) at least two of the radicals R a , R b and R c are independently selected from the group of C3 to C 12-alkyl and C3- to C 12 -hydroxyalkyl radicals. 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 13 -alkyl radicals; ii) X is selected from the group C6H4iii) at least two of the radicals R a , R b and R c are independently selected from the group of C3 to C 12 -alkyl and C3- to C 12 -hydroxyalkyl radicals. 3. A compound of general formula (1) according to point 2, wherein i) R is selected from the group of linear C 10 - to C 13 -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 13 -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 13-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 H 25 -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 selected from the group (OC2H4) n O with n = 1 to 8 iii) at least two of the radicals R a , R b and R c are independently selected from the group of C3 to C 12 -alkyl and C3- to C 12 -hydroxyalkyl radicals. 9. A compound of the general formula (1) according to point 1, wherein i) R is selected from the group of C7 to C 17-alkyl radicals; ii) X is selected from the group C(O)-N(CH3)CH2CH2; iii) at least two of the radicals R a , R b and R c are independently selected from the group of C3 to C 12 -alkyl and C3- to C 12 -hydroxyalkyl radicals. 10. A compound of the general formula (1) according to point 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 C 17 -alkyl; iii) at least two of the radicals R a , R b and R c are independently selected from the group of C3 to C 12 -alkyl and C3- to C 12 -hydroxyalkyl radicals. 11. A compound of general formula (1) according to any one of the previous points, wherein i) at least two of the radicals R a , R b and R c are independently selected from the group of C3 to C 12-Alkyl radicals, preferably from the group of C3- to C6-alkyl radicals. 12. A compound of the general formula (1) according to any one of the preceding points, wherein iii) the three radicals R a , R b and R c are independently selected from the group of C3 to C 12 -Alkyl radicals, preferably from the group of C3- to C6-alkyl radicals. 13. A compound of the general formula (1) according to any one of items 1 to 10, wherein iii) at least two of the radicals R a , R b and R c are independently selected from the group of C3 to C 12 -hydroxyalkyl radicals, preferably from the group of C3- to C6-hydroxyalkyl radicals. 14. A compound of the general formula (1) according to any one of items 1 to 10 or 13, wherein iii) the three radicals R a , R b and R c are independently selected from the group of C3 to C 12-hydroxyalkyl radicals, preferably from the group of C3- to C6-hydroxyalkyl radicals. 15. A compound of the general formula (1) according to any one of items 1 to 10, 13 or 14, wherein iii) the three radicals R a , R b and R c each represents a (CH2CH(OH)CH3)-hydroxyalkyl radical. 16. A compound of general formula (1) according to point 1, where i) R represents a linear C 12 H 25 -alkyl radical; ii) X is selected from the group C6H4 iii) R a , R b and R c each represents a (CH2CH(OH)CH3)-hydroxyalkyl radical. 17. A compound of general formula (1) according to point 1, where i) R represents a linear secondary C 12 H 25 -alkyl radical; ii) X is selected from the group C6H4iii) R a , R b and R ceach represent a (CH2CH(OH)CH3)-hydroxyalkyl radical. 18. Washing or cleaning agent containing a compound of the general formula (1) according to any one of the preceding points. 19. Liquid washing or cleaning agent containing a compound of the general formula (1) according to any one of the preceding points. 20. Washing or cleaning agent according to any one of points 18 or 19, wherein the washing or cleaning agent is free of fluorinated hydrocarbon solvents. 21. 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 17 or a washing or cleaning agent according to point 18 is introduced into a washing liquor or applied to a textile surface. 22. A process according to point 21, wherein the washing liquor is free of fluorinated hydrocarbon solvents. 23. A process according to any one of points 21 or 22, wherein the washing liquor is aqueous. 24.A process for cleaning hard surfaces, in the course of which a compound of the general formula (1) according to any one of the preceding points 1 to 17 or a washing or cleaning agent according to point 18 is introduced into a cleaning liquor or applied to a hard surface. 25. A process according to point 24, wherein the cleaning liquor is free of fluorine-containing hydrocarbon solvents. 26. A process according to any one of points 24 or 25, wherein the cleaning liquor is aqueous. 27. A process for preparing a compound of the general formula (1) according to any one of points 1 to 17, comprising the steps of 1) providing a sulfonic acid of the general formula RX-SO3H (2), 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) R 1 O(O)CCH2(R 1 O(O)C)CH with R = C7- to C 20-Alkyl 2) Providing an amine of the general formula N(R a R b R c ) (3), where at least two of the radicals R a , R b and R c are selected from the group of C3 to C 12 -alkyl and C3- to C 12 -hydroxyalkyl radicals; 3) Mixing the sulfonic acid (2) and the amine (3) to form a compound of general formula (1). Examples: Equimolar amounts of dodecylbenzenesulfonic acid and triisopropanolamine are reacted in a reaction vessel. A transparent, viscous, surface-active ionic liquid of formula C is formed. 12 H 25 -C6H4-SO3-HN + (CH2CH(OH)CH3)3. The neutralization products of dodecylbenzenesulfonic acid with triisopropanolamine (according to the invention) and monoisopropanamine (not according to the invention) were investigated with regard to their optical properties using polarization microscopy: The rheological investigation of the neutralization products of dodecylbenzenesulfonic acid with triisopropanolamine (according to the invention) and monoisopropanamine (not according to the invention) gave the following results: Thermal analysis by differential scanning calorimetry (DSC) of the neutralization products of dodecylbenzenesulfonic acid with triisopropanolamine (according to the invention) and monoisopropanamine (not according to the invention) gave the following result: An exemplary detergent composition containing a compound of the general formula 1) polyalkoxylated amine with a weight-average molecular weight M w in the range from 600 g / mol to 10000 g / mol, which is obtainable by reacting ammonia or primary alkyl or hydroxyalkylamines having a molecular weight below 200 g / mol with alkylene oxides 2)polyalkoxylated polyalkyleneimine, which is obtainable by reacting polyalkyleneimines with alkylene oxides

Claims

Patent claims:

1. Compound of the general formula (1) RX-SO3-HN + (R a R b R c ) (1), where e) R is selected from the group of C6 to C 20 -Alkyl groups; ii) X is selected from group a) C6H4b) (OC2H4) n O with n = 2 to 8 c) C(O)-N(CH3)CH2CH2 d) R 1 O(O)CCH2(R 1 O(O)C)CH with R 1 = C6 to C 20 -Alkyl iii) at least two of the R groups a , R b and R c selected independently from the group of C3 to C 12 -Alkyl and C3 to C 12 -Hydroxyalkyl groups.

2. Compound of general formula (1) according to claim 1, wherein i) R is selected from the group of C 10 - to C 13 -Alkyl groups; ii) X is selected from the group C6H4 iii) at least two of the R groups a , R b and R c selected independently from the group of C3 to C 12 -Alkyl and C3 to C12 -Hydroxyalkyl groups.

3. Compound of general formula (1) according to any one of the preceding claims, wherein i) R represents a linear secondary C 12 H 25 -alkyl group.

4. Compound of general formula (1) according to one of the preceding claims, wherein iii) the three R groups a , R b and R c selected independently from the group of C3 to C 12 -Hydroxyalkyl groups, preferably from the group of C3 to C6 hydroxyalkyl groups.

5. Compound of general formula (1) according to one of the preceding claims, wherein i) R represents a linear C 12 H 25 -Alkyl group is present; ii) X is selected from the group C6H4 iii) R a , R b and R c each representing a (CH2CH(OH)CH3)-hydroxyalkyl group.

6. Compound of general formula (1) according to one of the preceding claims, wherein Oi) R represents a linear secondary C 12 H 25-Alkyl group is present; Oii) X is selected from the group C6H4iii) R a , R b and R c each representing a (CH2CH(OH)CH3)-hydroxyalkyl group.

7. Washing or cleaning agent comprising a compound of general formula (1) according to any one of the preceding claims.

8. A method for washing textiles, wherein a compound of general formula (1) according to any one of claims 1 to 6 or a washing or cleaning agent according to claim 7 is introduced into a washing liquor or applied to a textile surface.

9. A method for cleaning hard surfaces, wherein a compound of general formula (1) according to any one of claims 1 to 6 or a washing or cleaning agent according to claim 7 is introduced into a cleaning liquor or applied to a hard surface.

10. A method for producing a compound of general formula (1) according to any one of claims 1 to 7, comprising the steps 1) providing a sulfonic acid of general formula RX-SO3H (2), wherein i) R is selected from the group consisting of C6 to C 20 -Alkyl groups; ii) X is selected from group a) C6H4b) (OC2H4) n O with n = 2 to 8 c) C(O)-N(CH3)CH2CH2 d) R 1 O(O)CCH2(R 1O(O)C)CH with R = C6- to C 20 -Alkyl 2) Providing an amine of the general formula N(R a R b R c ) (3), wherein at least two of the remainders R a , R b and R c selected from the group of C3 to C 12 -Alkyl and C3 to C 12 -Hydroxyalkyl groups; 3) Mixing the sulfonic acid (2) and the amine (3) to form a compound of the general formula (1).

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