Wash-Active Compounds

Abstract

Disclosed is a compound of the general formula (1) RXSO.sub.3HN+(R.sub.aR.sub.bR.sub.c) (1), wherein i) R is selected from the group of C.sub.6 to C.sub.20 alkyl groups; ii) X is selected from the group a) C.sub.6H.sub.4, b) (OC2H4)nO, in which n=2 to 8, c) C(O)N(CH.sub.3)CH.sub.2CH.sub.2, and d) R1O(O)CCH2(R1O(O)C)CH, in which R.sup.1C.sub.6 to C.sub.20 alkyl; iii) at least two of the groups R.sub.a, R.sub.b, and R.sub.c are selected independently of each other from the group consisting of C.sub.3 to C.sub.12 alkyl and C.sub.3 to C.sub.12 hydroxyalkyl groups. Also disclosed are detergents containing the compound, and washing and cleaning methods using the compound, and methods for producing same.

Claims

1. A compound of general formula (1)
RXSO.sub.3.sup.HN.sup.+(R.sub.aR.sub.bR.sub.c)(1), wherein i.) R is selected from the group of C.sub.6 to C.sub.20 alkyl functional groups; ii) X is selected from the group a) C.sub.6H.sub.4 b) (OC.sub.2H.sub.4).sub.nO where n=2 to 8 c) C(O)N(CH.sub.3)CH.sub.2CH.sub.2 d) R.sup.1O(O)CCH.sub.2(R.sup.1O(O)C)CH, in which R.sup.1C.sub.6 to C.sub.20 alkyl iii) at least two of the functional groups R.sub.a, R.sub.b, and R.sub.c are selected independently of each other from the group consisting of C.sub.3 to C.sub.12 alkyl and C.sub.3 to C.sub.12 hydroxyalkyl functional groups.

2. The compound of general formula (1) according to claim 1, wherein i) R is selected from the group of C.sub.10 to C.sub.13 alkyl functional groups; ii) X is selected from group C.sub.6H.sub.4 iii) at least two of the functional groups R.sub.a, R.sub.b, and R.sub.c are selected independently of each other from the group consisting of C.sub.3 to C.sub.12 alkyl and C.sub.3 to C.sub.12 hydroxyalkyl functional groups.

3. The compound of general formula (1) according to claim 1, wherein i) R represents a linear secondary C.sub.12H.sub.25 alkyl functional group.

4. The compound of general formula (1) according to claim 1, wherein i) the three functional groups R.sub.a, R.sub.b, and R.sub.c are selected independently of each other from the group consisting of C.sub.3 to C.sub.12 hydroxyalkyl functional groups.

5. The compound of general formula (1) according to claim 1, wherein i) R represents a linear C.sub.12H.sub.25 alkyl functional group; ii) X is selected from group C.sub.6H.sub.4 iii) R.sub.a, R.sub.b, and R.sub.c each represent a (CH.sub.2CH(OH)CH.sub.3) hydroxyalkyl functional group.

6. The compound of general formula (1) according to claim 1, wherein i) R represents a linear secondary C.sub.12H.sub.25 alkyl functional group; ii) X is selected from the group C.sub.6H.sub.4 iii) R.sub.a, R.sub.b, and R.sub.c each represent a (CH.sub.2CH(OH)CH.sub.3) hydroxyalkyl functional group.

7. A detergent or cleaning agent containing a compound of general formula (1) according to claim 1.

8. A process for washing textiles, over the course of which a compound of general formula (1) according to claim 1 is introduced into a washing liquor or is applied to a textile surface.

9. A process for cleaning hard surfaces, over the course of which a compound of general formula (1) according to claim 1 is introduced into a cleaning liquor or is applied to a hard surface.

10. A process for preparing a compound of the general formula (1) according to claim 1, comprising the steps of 1) providing a sulfonic acid of general formula RXSO.sub.3H (2), wherein i) R is selected from the group of C.sub.6 to C.sub.20 alkyl functional groups; ii) X is selected from the group a) C.sub.6H.sub.4 b) (OC.sub.2H.sub.4).sub.nO where n=2 to 8 c) C(O)N(CH.sub.3)CH.sub.2CH.sub.2 d) R.sup.1O(O)CCH.sub.2(R.sup.1O(O)C)CH, in which RC.sub.6 to C.sub.20 alkyl 2) providing an amine of general formula N(R.sub.aR.sub.bR.sub.c) (3), in which at least two of the functional groups R.sub.a, R.sub.b, and R.sub.c are selected from the group consisting of C.sub.3 to C.sub.12 alkyl and C.sub.3 to C.sub.12 hydroxyalkyl functional groups; 3) mixing the sulfonic acid (2) and the amine (3) to form a compound of general formula (1).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0018] A first subject matter of the application is a compound of general formula (1) RXSO.sub.3.sup.HN.sup.+(R.sub.aR.sub.bR.sub.c) (1), wherein [0019] i) R is selected from the group of C.sub.6 to C.sub.20 alkyl functional groups; [0020] ii) X is selected from the group [0021] a) C.sub.6H.sub.4 [0022] b) (OC.sub.2H.sub.4).sub.nO where n=2 to 8 [0023] c) C(O)N(CH.sub.3)CH.sub.2CH.sub.2 [0024] d) R.sup.1O(O)CCH.sub.2(R.sup.1O(O)C)CH, in which R.sup.1C.sub.6 to C.sub.20 alkyl iii) at least two of the functional groups R.sub.a, R.sub.b, and R.sub.c are selected independently of each other from the group consisting of C.sub.3 to C.sub.12 alkyl and C.sub.3 to C.sub.12 hydroxyalkyl functional groups.

[0025] Surprisingly, it was found that surface-active ionic liquids can be obtained by neutralizing specific anionic surfactant acids containing sulfonic acid groups using dialkyl- or trialkyl- 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 wt. %.

[0026] A particularly preferred compound of general formula (1) is based upon anionic detergents from the group of alkylbenzene sulfonic acids. Particularly preferred compounds of general formula (1) are therefore characterized in that [0027] i) R is selected from the group of C.sub.10 to C.sub.13 alkyl functional groups; [0028] ii) X is selected from group C.sub.6H.sub.4 [0029] iii) at least two of the functional groups R.sub.a, R.sub.b, and R.sub.c are selected independently of each other from the group consisting of C.sub.3 to C.sub.12 alkyl and C.sub.3 to C.sub.12 hydroxyalkyl functional groups.

[0030] Functional groups R selected from the group of linear C.sub.10 to C.sub.13 alkyl groups, secondary C.sub.10 to C.sub.13 alkyl functional groups and in particular linear secondary C.sub.10 to C.sub.13 alkyl functional groups have proven to be particularly advantageous. Very particular preference is given to functional groups R from the group of linear C.sub.12H.sub.25 alkyl functional groups, in particular the linear secondary C.sub.12H.sub.25 alkyl functional groups.

[0031] In alternative embodiments, the sulfonic acid on which the compound of general formula (1) is based can be varied.

[0032] A first alternative forms compounds of general formula (1), wherein [0033] i) R is selected from the group of C.sub.12 to C.sub.20 alkyl functional groups; [0034] ii) X is selected from the group selected from the group (OC.sub.2H.sub.4).sub.nO where n=1 to 8 [0035] iii) at least two of the functional groups R.sub.a, R.sub.b, and R.sub.c are selected independently of each other from the group consisting of C.sub.3 to C.sub.12 alkyl and C.sub.3 to C.sub.12 hydroxyalkyl functional groups.

[0036] A further alternative comprises compounds of general formula (1), wherein [0037] i) R is selected from the group of C.sub.7 to C.sub.17 alkyl functional groups; [0038] ii) X is selected from the group C(O)N(CH.sub.3)CH.sub.2CH.sub.2; [0039] iii) at least two of the functional groups R.sub.a, R.sub.b, and R.sub.c are selected independently of each other from the group consisting of C.sub.3 to C.sub.12 alkyl and C.sub.3 to C.sub.12 hydroxyalkyl functional groups.

[0040] The third alternative represents compounds of general formula (1), wherein [0041] i) R is selected from the group of C.sub.7 to C.sub.17 alkyl functional groups; [0042] ii) X is selected from the group O(O)CCH.sub.2(RO(O)C)CH where RC.sub.6 to C.sub.17 alkyl; [0043] iii) at least two of the functional groups R.sub.a, R.sub.b, and R.sub.c are selected independently of each other from the group consisting of C.sub.3 to C.sub.12 alkyl and C.sub.3 to C.sub.12 hydroxyalkyl functional groups.

[0044] In addition to the sulfonic acid group-containing anionic surfactant acids, the compounds of general formula (1) furthermore comprise specific dialkyl- or trialkyl- or -hydroxyalkylamines.

[0045] In a first embodiment, at least two of the functional groups R.sub.a, R.sub.b, and R.sub.c are selected independently of each other from the group consisting of C.sub.3 to C.sub.12 alkyl functional groups, preferably from the group consisting of C.sub.3 to C.sub.6 alkyl functional groups. In particular, compounds of general formula (1) in which the three functional groups R.sub.a, R.sub.b, and R.sub.c are selected independently of each other from the group consisting of C.sub.3 to C.sub.12 alkyl functional groups, preferably from the group consisting of C.sub.3 to C.sub.6 alkyl functional groups, are particularly preferred.

[0046] Some preferred compounds of general formula RXSO.sub.3.sup.HN.sup.+(R.sub.aR.sub.bR.sub.c), in which [0047] X is selected from the group [0048] a) C.sub.6H.sub.4 [0049] b) (OC.sub.2H.sub.4).sub.nO where n=1 to 8 [0050] c) C(O)N(CH.sub.3)CH.sub.2CH.sub.2 [0051] d) O(O)CCH.sub.2(R.sup.1O(O)CH, in which R.sup.1C.sub.6 to C.sub.20 alkyl, [0052] can be found in the following table:

TABLE-US-00001 R R.sub.a/R.sub.b R.sub.c 1a C.sub.6 to C.sub.20 alkyl C.sub.3 to C.sub.12 alkyl H 2a C.sub.6 to C.sub.20 alkyl C.sub.3 to C.sub.6 alkyl H 3a C.sub.6 to C.sub.20 alkyl C.sub.3 alkyl H 4a C.sub.6 to C.sub.20 alkyl n-C.sub.3 alkyl H 5a C.sub.6 to C.sub.20 alkyl iso-C.sub.3 alkyl H 6a C.sub.6 to C.sub.20 alkyl C.sub.4 alkyl H 7a C.sub.6 to C.sub.20 alkyl n-C.sub.4 alkyl H 8a C.sub.6 to C.sub.20 alkyl iso-C.sub.4 alkyl H 9a C.sub.6 to C.sub.20 alkyl sec-C.sub.4 alkyl H 10a C.sub.12 alkyl C.sub.3 to C.sub.12 alkyl H 11a C.sub.12 alkyl C.sub.3 to C.sub.6 alkyl H 12a C.sub.12 alkyl C.sub.3 alkyl H 13a C.sub.12 alkyl n-C.sub.3 alkyl H 14a C.sub.12 alkyl iso-C.sub.3 alkyl H 15a C.sub.12 alkyl C.sub.4 alkyl H 16a C.sub.12 alkyl n-C.sub.4 alkyl H 17a C.sub.12 alkyl iso-C.sub.4 alkyl H 18a C.sub.12 alkyl sec-C4 alkyl H 19a C.sub.6 to C.sub.20 alkyl C.sub.3 to C.sub.12 alkyl C.sub.3 to C.sub.12 alkyl 20a C.sub.6 to C.sub.20 alkyl C.sub.3 to C.sub.6 alkyl C.sub.3 to C.sub.6 alkyl 21a C.sub.6 to C.sub.20 alkyl C.sub.3 alkyl C.sub.3 alkyl 22a C.sub.6 to C.sub.20 alkyl n-C.sub.3 alkyl n-C.sub.3 alkyl 23a C.sub.6 to C.sub.20 alkyl iso-C.sub.3 alkyl iso-C.sub.3 alkyl 24a C.sub.6 to C.sub.20 alkyl C.sub.4 alkyl C.sub.4 alkyl 25a C.sub.6 to C.sub.20 alkyl n-C.sub.4 alkyl n-C.sub.4 alkyl 26a C.sub.6 to C.sub.20 alkyl iso-C.sub.4 alkyl iso-C.sub.4 alkyl 27a C.sub.6 to C.sub.20 alkyl sec-C.sub.4 alkyl sec-C.sub.4 alkyl 28a C.sub.12 alkyl C.sub.3 to C.sub.12 alkyl C.sub.3 to C.sub.12 alkyl 29a C.sub.12 alkyl C.sub.3 to C.sub.6 alkyl C.sub.3 to C.sub.6 alkyl 30a C.sub.12 alkyl C.sub.3 alkyl C.sub.3 alkyl 31a C.sub.12 alkyl n-C.sub.3 alkyl n-C.sub.3 alkyl 32a C.sub.12 alkyl iso-C.sub.3 alkyl iso-C.sub.3 alkyl 33a C.sub.12 alkyl C.sub.4 alkyl C.sub.4 alkyl 34a C.sub.12 alkyl n-C.sub.4 alkyl n-C.sub.4 alkyl 35a C.sub.12 alkyl iso-C.sub.4 alkyl iso-C.sub.4 alkyl 36a C.sub.12 alkyl sec-C.sub.4 alkyl sec-C.sub.4 alkyl

[0053] In a second embodiment, at least two of the functional groups R.sub.a, R.sub.b, and R.sub.c are selected independently of each other from the group consisting of C.sub.3 to C.sub.12 hydroxyalkyl functional groups, preferably from the group consisting of C.sub.3 to C.sub.6 hydroxyalkyl functional groups. In particular, compounds of general formula (1) in which the three functional groups R.sub.a, R.sub.b, and R.sub.c are selected independently of each other from the group consisting of C.sub.3 to C.sub.12 hydroxyalkyl functional groups, preferably from the group consisting of C.sub.3 to C.sub.6 hydroxyalkyl functional groups, are particularly preferred.

[0054] Particularly advantageous properties are exhibited by compounds of the general formula (1) in which the three functional groups R.sub.a, R.sub.b, and R.sub.c each represent a (CH.sub.2CH(OH)CH.sub.3) hydroxyalkyl functional group.

[0055] Very particularly preference is given to a compound of general formula (1) in which [0056] i) R represents a linear C.sub.12H.sub.25 alkyl functional group, preferably a linear secondary C.sub.12H.sub.25 alkyl functional group; [0057] ii) X is selected from group C.sub.6H.sub.4 [0058] iii) R.sub.a, R.sub.b, and R.sub.c each represent a (CH.sub.2CH(OH)CH.sub.3) hydroxyalkyl functional group.

[0059] Some particularly preferred compounds of general formula RXSO.sub.3.sup.HN.sup.+(R.sub.aR.sub.bR.sub.c), in which [0060] X is selected from the group [0061] a) C.sub.6H.sub.4 [0062] b) (OC.sub.2H.sub.4).sub.nO where n=1 to 8 [0063] c) C(O)N(CH.sub.3)CH.sub.2CH.sub.2 [0064] d) O(O)CCH.sub.2(R.sup.1O(O)C)CH, in which R.sup.1C.sub.6 to C.sub.20 alkyl, [0065] can be found in the following table:

TABLE-US-00002 R R.sub.a/R.sub.b R.sub.c 1b C.sub.6 to C.sub.20 alkyl C.sub.3 to C.sub.12 hydroxyalkyl H 2b C.sub.6 to C.sub.20 alkyl C.sub.3 to C.sub.6 hydroxyalkyl H 3b C.sub.6 to C.sub.20 alkyl C.sub.3 hydroxyalkyl H 4b C.sub.6 to C.sub.20 alkyl n-C.sub.3 hydroxyalkyl H 5b C.sub.6 to C.sub.20 alkyl iso-C.sub.3 hydroxyalkyl H 6b C.sub.6 to C.sub.20 alkyl C.sub.4 hydroxyalkyl H 7b C.sub.6 to C.sub.20 alkyl n-C.sub.4 hydroxyalkyl H 8b C.sub.6 to C.sub.20 alkyl iso-C.sub.4 hydroxyalkyl H 9b C.sub.6 to C.sub.20 alkyl sec-C.sub.4 hydroxyalkyl H 10b C.sub.12 alkyl C.sub.3 to C.sub.12 hydroxyalkyl H 11b C.sub.12 alkyl C.sub.3 to C.sub.6 hydroxyalkyl H 12b C.sub.12 alkyl C.sub.3 hydroxyalkyl H 13b C.sub.12 alkyl n-C.sub.3 hydroxyalkyl H 14b C.sub.12 alkyl iso-C.sub.3 hydroxyalkyl H 15b C.sub.12 alkyl C.sub.4 hydroxyalkyl H 16b C.sub.12 alkyl n-C.sub.4 hydroxyalkyl H 17b C.sub.12 alkyl iso-C.sub.4 hydroxyalkyl H 18b C.sub.12 alkyl sec-C.sub.4 hydroxyalkyl H 19b C.sub.6 to C.sub.20 alkyl C.sub.3 to C.sub.12 hydroxyalkyl C.sub.3 to C.sub.12 hydroxyalkyl 20b C.sub.6 to C.sub.20 alkyl C.sub.3 to C.sub.6 hydroxyalkyl C.sub.3 to C.sub.6 hydroxyalkyl 21b C.sub.6 to C.sub.20 alkyl C.sub.3 hydroxyalkyl C.sub.3 hydroxyalkyl 22b C.sub.6 to C.sub.20 alkyl n-C.sub.3 hydroxyalkyl n-C.sub.3 hydroxyalkyl 23b C.sub.6 to C.sub.20 alkyl iso-C.sub.3 hydroxyalkyl iso-C.sub.3 hydroxyalkyl 24b C.sub.6 to C.sub.20 alkyl C.sub.4 hydroxyalkyl C.sub.4 hydroxyalkyl 25b C.sub.6 to C.sub.20 alkyl n-C.sub.4 hydroxyalkyl n-C.sub.4 hydroxyalkyl 26b C.sub.6 to C.sub.20 alkyl iso-C.sub.4 hydroxyalkyl iso-C.sub.4 hydroxyalkyl 27b C.sub.6 to C.sub.20 alkyl sec-C.sub.4 hydroxyalkyl sec-C.sub.4 hydroxyalkyl 28b C.sub.12 alkyl C.sub.3 to C.sub.12 hydroxyalkyl C.sub.3 to C.sub.12 hydroxyalkyl 29b C.sub.12 alkyl C.sub.3 to C.sub.6 hydroxyalkyl C.sub.3 to C.sub.6 hydroxyalkyl 30b C.sub.12 alkyl C.sub.3 hydroxyalkyl C.sub.3 hydroxyalkyl 31b C.sub.12 alkyl n-C.sub.3 hydroxyalkyl n-C.sub.3 hydroxyalkyl 32b C.sub.12 alkyl iso-C.sub.3 hydroxyalkyl iso-C.sub.3 hydroxyalkyl 33b C.sub.12 alkyl C.sub.4 hydroxyalkyl C.sub.4 hydroxyalkyl 34b C.sub.12 alkyl n-C.sub.4 hydroxyalkyl n-C.sub.4 hydroxyalkyl 35b C.sub.12 alkyl iso-C.sub.4 hydroxyalkyl iso-C.sub.4 hydroxyalkyl 36b C.sub.12 alkyl sec-C.sub.4 hydroxyalkyl sec-C.sub.4 hydroxyalkyl

[0066] Very particular preference is given to a compound of formula C.sub.12H.sub.25C.sub.6H.sub.4SO.sub.3.sup.HN.sup.+(CH.sub.2CH(OH)CH.sub.3).sub.3.

[0067] As stated at the outset, the compounds of general formula (1) are particularly suitable as components of detergent or cleaning agents, in particular liquid detergent or cleaning agents, due to their physical properties. Corresponding detergent or cleaning agents containing a compound of general formula (1) are therefore further subject matter of this application.

[0068] A washing agent is a composition which is suitable for cleaning or caring for textiles and contains at least one textile-cleaning or textile-care active substance.

[0069] Examples of textile-cleaning active substances are [0070] surfactants, in particular nonionic or anionic surfactants, [0071] builders, such as phosphonates or water-softening polymers,

[0072] Examples of textile-care active substances are [0073] fragrances, in particular encapsulated fragrances, [0074] fabric softeners, in particular cationic surfactants and cationic polymers, [0075] dyes, in particular textile coloring agents.

[0076] The detergents are preferably free of fluorine-containing hydrocarbon solvents.

[0077] A further subject matter of the application is a process for washing textiles, in the course of which a compound of the general formula (1) or a detergent containing a compound of the general formula (1) is introduced into a washing liquor. The washing liquor is preferably aqueous and free of fluorine-containing hydrocarbon solvents.

[0078] A cleaning agent is a composition which is suitable for cleaning and caring for hard surfaces and contains at least one surface-cleaning or surface-care active substance.

[0079] Examples of surface-cleaning active substances are [0080] surfactants, in particular nonionic or anionic surfactants, [0081] builders, such as phosphonates or water-softening polymers,

[0082] Examples of surface-care active substances are [0083] corrosion inhibitors, in particular zinc salts, [0084] hydrophobizing agents, in particular polymeric hydrophobizing agents.

[0085] The cleaning agents are preferably free of fluorine-containing hydrocarbon solvents.

[0086] 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 liquor is preferably aqueous and free of fluorine-containing hydrocarbon solvents.

[0087] The composition of some preferred liquid detergent or cleaning agents can be found in the following tables (amounts given in wt. % based upon the total weight of the preparation, unless otherwise indicated). The listed detergent or cleaning agents are free of fluorine-containing hydrocarbon solvents.

TABLE-US-00003 Formula 1 Formula 2 Formula 3 Formula 4 A compound of general 5 to 80 10 to 70 15 to 65 20 to 60 formula (1) Non-ionic surfactant 5 to 50 10 to 45 15 to 40 20 to 35 Misc. up to 100 up to 100 up to 100 up to 100 Formula 6 Formula 2 Formula 8 Formula 9 A compound of general 5 to 80 10 to 70 15 to 65 20 to 60 formula (1) Non-ionic surfactant 5 to 50 10 to 45 15 to 40 20 to 35 Polyalkoxylated amine .sup.1) 0.5 to 10 1 to 8 1 to 8 3 to 6 Misc. up to 100 up to 100 up to 100 up to 100 Formula 11 Formula 12 Formula 13 Formula 14 A compound of general 5 to 80 10 to 70 15 to 65 20 to 60 formula (1) Non-ionic surfactant 5 to 50 10 to 45 15 to 40 20 to 35 Polyalkoxylated 0.5 to 10 1 to 8 1 to 8 3 to 6 polyalkyleneimine .sup.2) Misc. up to 100 up to 100 up to 100 up to 100 Formula 16 Formula 17 Formula 18 Formula 19 A compound of general 5 to 80 10 to 70 15 to 65 20 to 60 formula (1) Non-ionic surfactant 5 to 50 10 to 45 15 to 40 20 to 35 Phosphonate 0.5 to 10 1 to 8 1 to 8 3 to 6 Misc. up to 100 up to 100 up to 100 up to 100

[0088] 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.

[0089] Compounds of general formula (1) can be prepared by neutralization of a corresponding sulfonic acid with the corresponding amine. A process for preparing a compound of general formula (1), comprising the steps of [0090] 1) providing a sulfonic acid of general formula RXSO.sub.3H (2), wherein [0091] i) R is selected from the group of C.sub.6 to C.sub.20 alkyl functional groups; [0092] ii) X is selected from the group [0093] a) C.sub.6H.sub.4 [0094] b) (OC.sub.2H.sub.4).sub.nO where n=2 to 8 [0095] c) C(O)N(H.sub.3)CH.sub.2H.sub.2 [0096] d) R.sup.1O(O)CCH.sub.2(R.sup.1O(O)C)CH, in which R.sup.1C.sub.7 to C.sub.20 alkyl [0097] 2) providing an amine of general formula N(R.sub.aR.sub.bR.sub.c) (3), in which at least two of the functional groups R.sub.a, R.sub.b, and R.sub.c are selected from the group consisting of C.sub.3 to C.sub.12 alkyl and C.sub.3 to C.sub.12 hydroxyalkyl functional groups; [0098] 3) mixing the sulfonic acid (2) and the amine (3) to form a compound of general formula (1) [0099] is another subject matter of this application.

[0100] Compounds of general formula (1) can, as described above, be prepared by reacting a sulfonic acid (2) with a corresponding amine (3). Preferred detergents based upon compounds of general formula (1) can thus be described in other words by their content of sulfonic acid (2) and amine (3). The composition of some preferred detergents or cleaning agents can be derived from the following tables (amounts given in wt. % based on the total weight of the preparation, unless otherwise indicated). The listed detergent or cleaning agents are free of fluorine-containing hydrocarbon solvents.

TABLE-US-00004 Formula 21 Formula 22 Formula 23 Formula 24 RXSO.sub.3H (2) .sup.1 5 to 25 5 to 25 10 to 20 10 to 20 Amine (3) 5 to 25 5 to 25 10 to 20 10 to 20 Non-ionic surfactant 5 to 50 10 to 45 15 to 40 20 to 35 Misc. up to 100 up to 100 up to 100 up to 100 Formula 25 Formula 26 Formula 27 Formula 28 RXSO.sub.3H (2) .sup.1 5 to 25 5 to 25 10 to 20 10 to 20 Amine (3) 5 to 25 5 to 25 10 to 20 10 to 20 Non-ionic surfactant 5 to 50 10 to 45 15 to 40 20 to 35 Enzyme preparation 0.2 to 12 0.5 to 10 0.5 to 10 1 to 8 Misc. up to 100 up to 100 up to 100 up to 100 Formula 31 Formula 32 Formula 33 Formula 34 RXSO.sub.3H (2) .sup.1 5 to 25 5 to 25 10 to 20 10 to 20 Amine (3) 5 to 25 5 to 25 10 to 20 10 to 20 Non-ionic surfactant 5 to 50 10 to 45 15 to 40 20 to 35 Wash- or cleaning- 0.1 to 14 0.2 to 12 0.5 to 10 0.5 to 10 active polymer Misc. up to 100 up to 100 up to 100 up to 100 Formula 35 Formula 36 Formula 37 Formula 38 R-X-SO.sub.3H (2) .sup.1 5 to 25 5 to 25 10 to 20 10 to 20 Amine (3) 5 to 25 5 to 25 10 to 20 10 to 20 Non-ionic surfactant 5 to 50 10 to 45 15 to 40 20 to 35 Phosphonate 0.5 to 10 1 to 8 1 to 8 3 to 6 Misc. up to 100 up to 100 up to 100 up to 100 Formula 41 Formula 42 Formula 43 Formula 44 RXSO.sub.3H (2) .sup.1 5 to 25 5 to 25 10 to 20 10 to 20 Amine (3) 5 to 25 5 to 25 10 to 20 10 to 20 Non-ionic surfactant 5 to 50 10 to 45 15 to 40 20 to 35 Fatty acid 1 to 12 1 to 12 2 to 10 2 to 10 Misc. up to 100 up to 100 up to 100 up to 100 Formula 45 Formula 46 Formula 47 Formula 48 RXSO.sub.3H (2) .sup.1 5 to 25 5 to 25 10 to 20 10 to 20 Amine (3) 5 to 25 5 to 25 10 to 20 10 to 20 Non-ionic surfactant 5 to 50 10 to 45 15 to 40 20 to 35 Enzyme preparation 0.2 to 12 0.5 to 10 0.5 to 10 1 to 8 Water <10 <10 <7 <5 Misc. up to 100 up to 100 up to 100 up to 100 Formula 51 Formula 52 Formula 53 Formula 54 RXSO.sub.3H (2) .sup.1 5 to 25 5 to 25 10 to 20 10 to 20 Amine (3) 5 to 25 5 to 25 10 to 20 10 to 20 Non-ionic surfactant 5 to 50 10 to 45 15 to 40 20 to 35 Enzyme preparation 0.2 to 12 0.5 to 10 0.5 to 10 1 to 8 Fatty acid 1 to 12 1 to 12 2 to 10 2 to 10 Water <10 <10 <7 <5 Misc. up to 100 up to 100 up to 100 up to 100 Formula 55 Formula 56 Formula 57 Formula 58 RXSO.sub.3H (2) .sup.1 5 to 25 5 to 25 10 to 20 10 to 20 Amine (3) 5 to 25 5 to 25 10 to 20 10 to 20 Non-ionic surfactant 5 to 50 10 to 45 15 to 40 20 to 35 Enzyme preparation 0.2 to 12 0.5 to 10 0.5 to 10 1 to 8 Fatty acid 1 to 12 1 to 12 2 to 10 2 to 10 Organic solvent 3 to 24 6 to 22 6 to 22 10 to 20 Water <10 <10 <7 <5 Misc. up to 100 up to 100 up to 100 up to 100 Formula 61 Formula 62 Formula 63 Formula 64 RXSO.sub.3H (2) .sup.1 5 to 25 5 to 25 10 to 20 10 to 20 Amine (3) 5 to 25 5 to 25 10 to 20 10 to 20 Non-ionic surfactant 5 to 50 10 to 45 15 to 40 20 to 35 Enzyme preparation 0.2 to 12 0.5 to 10 0.5 to 10 1 to 8 Fatty acid 1 to 12 1 to 12 2 to 10 2 to 10 Wash- or cleaning- 0.1 to 14 0.2 to 12 0.5 to 10 0.5 to 10 active polymer Organic solvent 3 to 24 6 to 22 6 to 22 10 to 20 Water <10 <10 <7 <5 Misc. up to 100 up to 100 up to 100 up to 100 .sup.1 X is selected from the group [0101] a) C.sub.6H.sub.4 [0102] b) (OC.sub.2H.sub.4).sub.nO where n=2 to 8 [0103] c) C(O)N(H.sub.3)CH.sub.2CH.sub.2 [0104] d) R.sup.1O(O)CCH.sub.2(R.sup.1O(O)C)CH, in which R.sup.1C.sub.7 to C.sub.20 alkyl [0105] preferably from C.sub.6H.sub.4

[0106] The compounds of general formula (1) are particularly suitable for the preparation of detergent compositions with a high detergent 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 detergent or cleaning agent product forms can be derived from the following tables (amounts given in wt. % based on the total weight of the preparation, unless otherwise indicated). The listed detergent or cleaning agents are free of fluorine-containing hydrocarbon solvents.

TABLE-US-00005 Formula 71 Formula 72 Formula 73 Formula 74 RXSO.sub.3H (2) .sup.2 20 to 40 20 to 40 25 to 35 25 to 35 Amine (3) 25 to 50 30 to 50 35 to 50 35 to 45 Non-ionic surfactant 0 to 15 0 to 15 2 to 12 4 to 10 Misc. up to 100 up to 100 up to 100 up to 100 Formula 75 Formula 76 Formula 77 Formula 78 RXSO.sub.3H (2) .sup.2 20 to 40 20 to 40 25 to 35 25 to 35 Amine (3) 25 to 50 30 to 50 35 to 50 35 to 45 Non-ionic surfactant 0 to 15 0 to 15 2 to 12 4 to 10 Enzyme preparation 0.2 to 12 0.5 to 10 0.5 to 10 1 to 8 Misc. up to 100 up to 100 up to 100 up to 100 Formula 81 Formula 82 Formula 83 Formula 84 RXSO.sub.3H (2) .sup.2 20 to 40 20 to 40 25 to 35 25 to 35 Amine (3) 25 to 50 30 to 50 35 to 50 35 to 45 Non-ionic surfactant 0 to 15 0 to 15 2 to 12 4 to 10 Wash- or cleaning- 0.1 to 14 0.2 to 12 0.5 to 10 0.5 to 10 active polymer Misc. up to 100 up to 100 up to 100 up to 100 Formula 85 Formula 86 Formula 87 Formula 88 RXSO.sub.3H (2) .sup.2 20 to 40 20 to 40 25 to 35 25 to 35 Amine (3) 25 to 50 30 to 50 35 to 50 35 to 45 Non-ionic surfactant 0 to 15 0 to 15 2 to 12 4 to 10 Phosphonate 0.5 to 10 1 to 8 1 to 8 3 to 6 Misc. up to 100 up to 100 up to 100 up to 100 Formula 91 Formula 92 Formula 93 Formula 94 RXSO.sub.3H (2) .sup.2 20 to 40 20 to 40 25 to 35 25 to 35 Amine (3) 25 to 50 30 to 50 35 to 50 35 to 45 Non-ionic surfactant 0 to 15 0 to 15 2 to 12 4 to 10 Fatty acid 1 to 12 1 to 12 2 to 10 2 to 10 Misc. up to 100 up to 100 up to 100 up to 100 Formula 95 Formula 96 Formula 97 Formula 98 RXSO.sub.3H (2) .sup.2 20 to 40 20 to 40 25 to 35 25 to 35 Amine (3) 25 to 50 30 to 50 35 to 50 35 to 45 Non-ionic surfactant 0 to 15 0 to 15 2 to 12 4 to 10 Enzyme preparation 0.2 to 12 0.5 to 10 0.5 to 10 1 to 8 Water <5 <5 <3 <3 Misc. up to 100 up to 100 up to 100 up to 100 Formula 101 Formula 102 Formula 103 Formula 104 RXSO.sub.3H (2) .sup.2 20 to 40 20 to 40 25 to 35 25 to 35 Amine (3) 25 to 50 30 to 50 35 to 50 35 to 45 Non-ionic surfactant 0 to 15 0 to 15 2 to 12 4 to 10 Enzyme preparation 0.2 to 12 0.5 to 10 0.5 to 10 1 to 8 Fatty acid 1 to 12 1 to 12 2 to 10 2 to 10 Water <5 <5 <3 <3 Misc. up to 100 up to 100 up to 100 up to 100 Formula 105 Formula 106 Formula 107 Formula 108 RXSO.sub.3H (2) .sup.2 20 to 40 20 to 40 25 to 35 25 to 35 Amine (3) 25 to 50 30 to 50 35 to 50 35 to 45 Non-ionic surfactant 0 to 15 0 to 15 2 to 12 4 to 10 Enzyme preparation 0.2 to 12 0.5 to 10 0.5 to 10 1 to 8 Fatty acid 1 to 12 1 to 12 2 to 10 2 to 10 Organic solvent <5 <5 <3 <3 Water <5 <5 <3 <3 Misc. up to 100 up to 100 up to 100 up to 100 Formula 111 Formula 112 Formula 113 Formula 114 RXSO.sub.3H (2) .sup.2 20 to 40 20 to 40 25 to 35 25 to 35 Amine (3) 25 to 50 30 to 50 35 to 50 35 to 45 Non-ionic surfactant 0 to 15 0 to 15 2 to 12 4 to 10 Enzyme preparation 0.2 to 12 0.5 to 10 0.5 to 10 1 to 8 Fatty acid 1 to 12 1 to 12 2 to 10 2 to 10 Wash- or cleaning- 0.1 to 14 0.2 to 12 0.5 to 10 0.5 to 10 active polymer Organic solvent <5 <5 <3 <3 Water <5 <5 <3 <3 Misc. up to 100 up to 100 up to 100 up to 100 .sup.2 X is selected from the group [0107] a) C.sub.6H.sub.4 [0108] b) (OC.sub.2H.sub.4).sub.nO where n=2 to 8 [0109] c) C(O)N(CH.sub.3)CH.sub.2CH.sub.2 [0110] d) R.sup.1O(O)CCH.sub.2(R.sup.1O(O)C)CH, in which R.sup.1C.sub.7 to C.sub.20 alkyl [0111] preferably from C.sub.6H.sub.4

[0112] The detergent or cleaning agents described above are preferably free of quaternary amines and organic pigments.

[0113] This application provides, inter alia, the following subject matter:

[0114] 1. A compound of general formula (1)

RXSO.sub.3.sup.HN.sup.+(R.sub.aR.sub.bR.sub.c)(1), where [0115] i) R is selected from the group of C.sub.6 to C.sub.20 alkyl functional groups; [0116] ii) X is selected from the group [0117] a) C.sub.6H.sub.4 [0118] b) b) (OC.sub.2H.sub.4).sub.nO where n=2 to 8 [0119] c) c) C(O)N(CH.sub.3)CH.sub.2CH.sub.2 [0120] d) d) R.sup.1O(O)CCH.sub.2(R.sup.1O(O)C)CH, in which R.sup.1C.sub.6 to C.sub.20 alkyl [0121] iii) at least two of the functional groups R.sub.a, R.sub.b, and R.sub.c are selected independently of each other from the group consisting of C.sub.3 to C.sub.12 alkyl and C.sub.3 to C.sub.12 hydroxyalkyl functional groups.

[0122] 2. The compound of general formula (1) according to point 1, wherein [0123] i) R is selected from the group of C.sub.10 to C.sub.13 alkyl functional groups; [0124] ii) X is selected from group C.sub.6H.sub.4 [0125] iii) at least two of the functional groups R.sub.a, R.sub.b, and R.sub.c are selected independently of each other from the group consisting of C.sub.3 to C.sub.12 alkyl and C.sub.3 to C.sub.12 hydroxyalkyl functional groups.

[0126] 3. The compound of general formula (1) according to point 2, wherein [0127] i) R is selected from the group of linear C.sub.10 to C.sub.13 alkyl functional groups.

[0128] 4. The compound of general formula (1) according to one of points 2 or 3, wherein [0129] i) R is selected from the group of secondary C.sub.10 to C.sub.13 alkyl functional groups.

[0130] 5. The compound of general formula (1) according to one of points 2 to 4, wherein [0131] i) R is selected from the group of linear secondary C.sub.10 to C.sub.13 alkyl functional groups.

[0132] 6. The compound of general formula (1) according to one of points 2 to 5, wherein [0133] i) R represents a linear C.sub.12H.sub.25 alkyl functional group.

[0134] 7. The compound of general formula (1) according to one of points 2 to 6, wherein [0135] i) R represents a linear secondary C.sub.12H.sub.25 alkyl functional group.

[0136] 8. The compound of general formula (1) according to point 1, wherein [0137] i) R is selected from the group of C.sub.12 to C.sub.20 alkyl functional groups; [0138] ii) X is selected from the group selected from the group (OC.sub.2H.sub.4).sub.nO where n=1 to 8 [0139] iii) at least two of the functional groups R.sub.a, R.sub.b, and R.sub.c are selected independently of each other from the group consisting of C.sub.3 to C.sub.12 alkyl and C.sub.3 to C.sub.12 hydroxyalkyl functional groups.

[0140] 9. The compound of general formula (1) according to point 1, wherein [0141] i) R is selected from the group of C.sub.7 to C.sub.17 alkyl functional groups; [0142] ii) X is selected from the group C(O)N(CH.sub.3)CH.sub.2CH.sub.2; [0143] iii) at least two of the functional groups R.sub.a, R.sub.b, and R.sub.c are selected independently of each other from the group consisting of C.sub.3 to C.sub.12 alkyl and C.sub.3 to C.sub.12 hydroxyalkyl functional groups.

[0144] 10. The compound of general formula (1) according to point 1, wherein [0145] i) R is selected from the group of C.sub.7 to C.sub.17 alkyl functional groups; [0146] ii) X is selected from the group O(O)CCH.sub.2(RO(O)C)CH where RC.sub.6 to C.sub.17 alkyl; [0147] iii) at least two of the functional groups R.sub.a, R.sub.b, and R.sub.c are selected independently of each other from the group consisting of C.sub.3 to C.sub.12 alkyl and C.sub.3 to C.sub.12 hydroxyalkyl functional groups.

[0148] 11. The compound of general formula (1) according to one of the preceding points, wherein [0149] i) at least two of the functional groups R.sub.a, R.sub.b, and R.sub.c are selected independently of each other from the group consisting of C.sub.3 to C.sub.12 alkyl functional groups, preferably from the group consisting of C.sub.3 to C.sub.6 alkyl functional groups.

[0150] 12. The compound of general formula (1) according to one of the preceding points, wherein [0151] iii) the three functional groups R.sub.a, R.sub.b, and R.sub.c are selected independently of each other from the group consisting of C.sub.3 to C.sub.12 alkyl functional groups, preferably from the group consisting of C.sub.3 to C.sub.6 alkyl functional groups.

[0152] 13. The compound of general formula (1) according to one of points 1 to 10, wherein [0153] iii) at least two of the functional groups R.sub.a, R.sub.b, and R.sub.c are selected independently of each other from the group consisting of C.sub.3 to C.sub.12 hydroxyalkyl functional groups, preferably from the group consisting of C.sub.3 to C.sub.6 hydroxyalkyl functional groups.

[0154] 14. The compound of general formula (1) according to one of points 1 to 10 or 13, wherein [0155] iii) the three functional groups R.sub.a, R.sub.b, and R.sub.c are selected independently of each other from the group consisting of C.sub.3 to C.sub.12 hydroxyalkyl functional groups, preferably from the group consisting of C.sub.3 to C.sub.6 hydroxyalkyl functional groups.

[0156] 15. The compound of general formula (1) according to one of points 1 to 10, 13, or 14, wherein [0157] iii) the three functional groups R.sub.a, R.sub.b, and R.sub.c each represent a (CH.sub.2CH(OH)CH.sub.3) hydroxyalkyl functional group.

[0158] 16. The compound of general formula (1) according to point 1, wherein [0159] i) R represents a linear C.sub.12H.sub.25 alkyl functional group; [0160] ii) X is selected from group C.sub.6H.sub.4 [0161] iii) R.sub.a, R.sub.b, and R.sub.c each represent a (CH.sub.2CH(OH)CH.sub.3) hydroxyalkyl functional group.

[0162] 17. The compound of general formula (1) according to point 1, wherein [0163] i) R represents a linear secondary C.sub.12H.sub.25 alkyl functional group; [0164] ii) X is selected from group C.sub.6H.sub.4 [0165] iii) R.sub.a, R.sub.b, and R.sub.c each represent a (CH.sub.2CH(OH)CH.sub.3) hydroxyalkyl functional group.

[0166] 18. A detergent or cleaning agent containing a compound of general formula (1) according to one of the preceding points.

[0167] 19. A liquid detergent or cleaning agent containing a compound of general formula (1) according to one of the preceding points.

[0168] 20. The detergent or cleaning agent according to one of points 18 or 19, wherein the detergent or cleaning agent is free of fluorine-containing hydrocarbon solvents.

[0169] 21. A process for washing textiles, over the course of which a compound of general formula (1) according to one of points 1 to 17 or a detergent or cleaning agent according to point 18 is introduced into a washing liquor or is applied to a textile surface.

[0170] 22. The process according to point 21, wherein the washing liquor is free of fluorine-containing hydrocarbon solvents.

[0171] 23. The process according to one of points 21 or 22, wherein the washing liquor is aqueous.

[0172] 24. A process for cleaning hard surfaces, over the course of which a compound of general formula (1) according to one of the preceding points 1 to 17 or a detergent or cleaning agent according to point 18 is introduced into a cleaning liquor or is applied to a hard surface.

[0173] 25. The process according to point 24, wherein the cleaning liquor is free of fluorine-containing hydrocarbon solvents.

[0174] 26. The process according to one of points 24 or 25, wherein the cleaning liquor is aqueous.

[0175] 27. A process for preparing a compound of general formula (1) according to one of points 1 to 17, comprising the steps of [0176] 1) providing a sulfonic acid of general formula RXSO.sub.3H (2), wherein [0177] i) R is selected from the group of C.sub.6 to C.sub.20 alkyl functional groups; [0178] ii) X is selected from the group [0179] a) C.sub.6H.sub.4 [0180] b) (OC.sub.2H.sub.4).sub.nO where n=2 to 8 [0181] c) C(O)N(CH.sub.3)CH.sub.2CH.sub.2 [0182] d) R.sup.1O(O)CCH.sub.2(R.sup.1O(O)C)CH, in which RC.sub.7 to C.sub.20 alkyl [0183] 2) providing an amine of general formula N(R.sub.aR.sub.bR.sub.c) (3), in which at least two of the functional groups R.sub.a, R.sub.b, and R.sub.c are selected from the group consisting of C.sub.3 to C.sub.12 alkyl and C.sub.3 to C.sub.12 hydroxyalkyl functional groups; [0184] 3) mixing the sulfonic acid (2) and the amine (3) to form a compound of general formula (1).

Examples

[0185] Equimolar amounts of dodecylbenzene sulfonic acid and triisopropanolamine are reacted with each other in a reaction vessel. A transparent, viscous, surface-active ionic liquid of the formula C.sub.12H.sub.25C.sub.6H.sub.4SO.sub.3.sup.HN.sup.+(CH.sub.2CH(OH)CH.sub.3).sub.3 is formed.

[0186] The neutralization products of dodecylbenzene sulfonic acid with triisopropanolamine (according to the invention) and monoisopropanolamine (not according to the invention) were investigated with regard to their optical properties using

TABLE-US-00006 C.sub.12H.sub.25C.sub.6H.sub.4SO.sub.3.sup.HN.sup.+(CH.sub.2CH(OH)CH.sub.3).sub.3 C.sub.12H.sub.25C.sub.6H.sub.4SO.sub.3.sup.H.sub.3N.sup.+CH.sub.2CH(OH)CH.sub.3 amorphous, isotropic liquid crystalline, anisotropic

[0187] The rheological investigation of the neutralization products of dodecylbenzene sulfonic acid with triisopropanolamine (according to the invention) and monoisopropanolamine (not according to the invention) gave the following results:

TABLE-US-00007 C.sub.12H.sub.25C.sub.6H.sub.4SO.sub.3.sup.HN.sup.+(CH.sub.2CH(OH)CH.sub.3).sub.3 C.sub.12H.sub.25C.sub.6H.sub.4SO.sub.3.sup.H.sub.3N.sup.+CH.sub.2CH(OH)CH.sub.3 no pour point pour point viscosity independent of shear rate viscosity dependent upon shear rate

[0188] Thermal analysis by differential scanning calorimetry (DSC) of the neutralization products of dodecylbenzene sulfonic acid with triisopropanolamine (according to the invention) and monoisopropanolamine (not according to the invention) gave the following result:

TABLE-US-00008 C.sub.12H.sub.25C.sub.6H.sub.4SO.sub.3.sup.HN.sup.+(CH.sub.2CH(OH)CH.sub.3).sub.3 C.sub.12H.sub.25C.sub.6H.sub.4SO.sub.3.sup.H.sub.3N.sup.+CH.sub.2CH(OH)CH.sub.3 glass transition temperature glass transition temperature and melting point

[0189] An exemplary detergent composition containing a compound of the general formula

TABLE-US-00009 Ingredient Wt. % Ethoxylated C.sub.12-C.sub.18 fatty alcohol 30 (7EO) C.sub.12H.sub.25C.sub.6H.sub.4SO.sub.3.sup.HN.sup.+(CH.sub.2CH(OH)CH.sub.3).sub.3 48 Polyalkoxylated amine .sup.1) 6 Polyalkoxylated polyalkyleneimine .sup.2) 6 DTPMP 5 Misc. up to 100 .sup.1) polyalkoxylated amine having a weight-average molecular weight Mw in the range of 600 g/mol to 10,000 g/mol, which is obtained by reacting ammonia or primary alkyl or hydroxyalkylamines having a molecular weight of less than 200 g/mol with alkylene oxides .sup.2) polyalkoxylated polyalkyleneimine which is obtained by reacting polyalkyleneimines with alkylene oxides.