Washing active compounds

Abstract

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

Description

[0001] The present invention relates to a detergent-active compound. The present application also relates to a detergent and a cleaning agent containing the detergent-active compound, a method for preparing the detergent-active compound, and a detergent and a cleaning method using the detergent-active compound.

[0002] Changing requirements are being placed on the forms in which detergents and cleaning agents are manufactured and supplied. A trend associated with the preparation of detergents and cleaning agents is towards their concentration. In addition to increased consumer acceptance due to simplified handling, the background to this development is particularly the sustainability aspect - for example in relation to transport volumes and costs and the amount of packaging material used.

[0003] The concentration of modern detergents and cleaners, in particular modern liquid detergents, often influences their optical and rheological properties, affects the storage stability of these agents and can influence their cleaning performance, in particular when high concentrations of active substances lead to incompatibilities.

[0004] In addition, concentrated detergents and cleaning agents usually involve the use of organic solvents. These solvents improve the physical stability of the detergents and cleaning agents, but are usually characterized by only low washing or cleaning activity, so they should be added in as little amount as possible, especially for sustainability reasons. However, the use of aqueous or aqueous-organic solvent systems in the production of concentrated liquid detergents still cannot avoid conventional washing or cleaning active ingredients.

[0005] European patent application EP 3670638 A1 describes the use of ionic liquids in combination with conventional aqueous or aqueous-organic solvent systems as components of detergents or cleaning agents.

[0006] US patent US 7,737,102 B2 describes cleaning active ionic liquids based on a combination of anionic surfactants and specific amine oxides.

[0007] Against this background, the present application is based on the object of providing washing and cleaning active substances which enable the preparation of visually attractive, concentrated, flowable detergent formulations. The active ingredients should be able to be produced in a simple and efficient manner, and they should have good storage capacity and be characterized in particular by a good cleaning effect.

[0008] This object is achieved by a new class of surfactant active ingredients.

[0009] The first subject of the present application is a compound of the general formula (1),

[0010] RX-SO3 - HN + (R a R b Rc )(1), where

[0011] i) R is selected from C6 to C 20 Alkyl functional group;

[0012] ii) X is selected from the following groups

[0013] a) C6H4

[0014] b)(OC2H4) n O, wherein n=2 to 8

[0015] c)C(O)-N(CH3)CH2CH2

[0016] d) R 1 O(O)CCH2(R 1 O(O)C)CH, where R 1 =C6 to C 20 alkyl

[0017] iii) Functional group R a , R b and R c At least two of which are independently selected from C3 to C 12 Alkyl and C3 to C 12 Hydroxyalkyl functional group.

[0018] Surprisingly, it has been found that surface-active ionic liquids can be obtained by neutralizing specific anionic surfactant acids containing sulfonic acid groups with dialkyl- or trialkyl- or hydroxyalkylamines. The amorphous transparent liquids are suitable, for example, for the production of solvent-free liquid detergents with an active ingredient content of up to 100 wt.%.

[0019] Particularly preferred compounds of the general formula (1) are based on anionic detergents selected from alkylbenzenesulfonic acids. Therefore, particularly preferred compounds of the general formula (1) are characterized in that

[0020] i) R is selected from C 10 To C 13 Alkyl functional group;

[0021] ii) X is selected from the group C6H4

[0022] iii) Functional group R a , R b and R c At least two of which are independently selected from C3 to C 12 Alkyl and C3 to C 12 Hydroxyalkyl functional group.

[0023] It has been shown that the straight chain C 10 To C 13 Alkyl, secondary C10 To C 13 Alkyl functional groups and especially straight-chain secondary C 10 To C 13 Alkyl functional groups are particularly advantageous. Very particular preference is given to linear C 12 H 25 Alkyl functional groups R, especially straight chain secondary C 12 H 25 Alkyl functional group.

[0024] In alternative embodiments, the sulfonic acid on which the compounds of formula (1) are based may vary.

[0025] A first alternative form of the compound of formula (1) wherein

[0026] i) R is selected from C 12 To C 20 Alkyl functional group;

[0027] ii) X is selected from the group (OC2H4) n O, wherein n=1 to 8

[0028] iii) Functional group R a , R b and R c At least two of which are independently selected from C3 to C 12 Alkyl and C3 to C 12 Hydroxyalkyl functional group.

[0029] Another alternative includes compounds of formula (1) wherein

[0030] i) R is selected from C7 to C 17 Alkyl functional group;

[0031] ii) X is selected from the group C(O)-N(CH3)CH2CH2;

[0032] iii) Functional group R a , R b and R c At least two of which are independently selected from C3 to C 12 Alkyl and C3 to C 12 Hydroxyalkyl functional group.

[0033] A third alternative form represents compounds of formula (1) wherein

[0034] i) R is selected from C7 to C 17 Alkyl functional group;

[0035] ii) X is selected from the group O(O)CCH2(RO(O)C)CH, wherein R=C6 to C 17 alkyl;

[0036] iii) Functional group R a , R b and R c At least two of which are independently selected from C3 to C 12 Alkyl and C3 to C 12 Hydroxyalkyl functional group.

[0037] Besides the anionic surfactant acids containing sulfonic acid groups, the compounds of the general formula (1) also include specific dialkyl- or trialkyl- or hydroxyalkylamines.

[0038] In a first embodiment, the functional group R a , R b and R c At least two of which are independently selected from C3 to C 12 The alkyl functional group is preferably selected from C3 to C6 alkyl functional groups. In particular, compounds of the general formula (1) are particularly preferred, wherein the three functional groups R a , R b and R c independently selected from C3 to C 12 The alkyl functional group is preferably selected from C3 to C6 alkyl functional groups.

[0039] General formula RX-SO3 - HN + (R a R b R c ) of some preferred compounds, wherein

[0040] X is selected from the following groups

[0041] a) C6H4

[0042] b)(OC2H4) n O, wherein n=1 to 8

[0043] c)C(O)-N(CH3)CH2CH2

[0044] d)O(O)CCH2(R 1 O(O)C)CH, where R 1 =C6 to C 20 alkyl,

[0045] This can be found in the table below:

[0046]

[0047]

[0048] In a second embodiment, the functional group R a, R b and R c At least two of which are independently selected from C3 to C 12 The hydroxyalkyl functional group is preferably selected from C3 to C6 hydroxyalkyl functional groups. In particular, compounds of the general formula (1) are particularly preferred, wherein the three functional groups R a , R b and R c independently selected from C3 to C 12 The hydroxyalkyl functional group is preferably selected from C3 to C6 hydroxyalkyl functional groups.

[0049] Compounds of the general formula (1) exhibit particularly advantageous properties, wherein the three functional groups R a , R b and R c Each represents a (CH2CH(OH)CH3)hydroxyalkyl functional group.

[0050] Very particular preference is given to compounds of the general formula (1) in which

[0051] i) R represents a straight chain C 12 H 25 Alkyl functional group, preferably a straight chain secondary C 12 H 25 Alkyl functional group;

[0052] ii) X is selected from the group C6H4

[0053] iii) R a , R b and R c Each represents a (CH2CH(OH)CH3)hydroxyalkyl functional group.

[0054] Some particularly preferred general formulas are RX-SO3 - HN + (R a R b R c ), wherein

[0055] X is selected from the following groups

[0056] a) C6H4

[0057] b)(OC2H4) n O, wherein n=1 to 8

[0058] c)C(O)-N(CH3)CH2CH2

[0059] d)O(O)CCH2(R 1 O(O)C)CH, where R 1 =C6 to C 20 alkyl,

[0060] This can be found in the table below:

[0061]

[0062]

[0063] Very particular preference is given to compounds of the formula

[0064] C 12 H 25 -C6H4-SO3 - HN + (CH2CH(OH)CH3)3.

[0065] As mentioned at the outset, the compounds of the general formula (1) are particularly suitable as components of washing or cleaning agents, in particular liquid washing or cleaning agents, due to their physical properties. Accordingly, corresponding washing or cleaning agents containing compounds of the general formula (1) are a further subject of the present application.

[0066] A detergent is a composition which is suitable for cleaning or caring for textiles and which contains at least one textile cleaning or textile care active substance.

[0067] Examples of textile cleaning actives are

[0068] - surfactants, in particular nonionic or anionic surfactants,

[0069] - builders, for example phosphonates or water-softening polymers,

[0070] Examples of textile care actives are

[0071] - spices, especially packaged spices,

[0072] - fabric softeners, in particular cationic surfactants and cationic polymers,

[0073] - Dyes, especially textile colorants.

[0074] The detergent preferably does not contain a fluorine-containing hydrocarbon solvent.

[0075] Another subject of the present application is a method for washing textiles, in which a compound of the general formula (1) or a washing agent containing a compound of the general formula (1) is introduced into a washing liquid. The washing liquid is preferably aqueous and does not contain fluorine-containing hydrocarbon solvents.

[0076] A cleaner is a composition which is suitable for cleaning and caring for hard surfaces and which contains at least one surface cleaning or surface care active substance.

[0077] Examples of surface cleaning active substances are

[0078] - surfactants, in particular nonionic or anionic surfactants,

[0079] - builders, for example phosphonates or water-softening polymers,

[0080] Examples of surface care actives are

[0081] - corrosion inhibitors, especially zinc salts,

[0082] - Hydrophobing agents, in particular polymeric hydrophobing agents.

[0083] The cleaning agent preferably does not contain fluorinated hydrocarbon solvents.

[0084] Another subject of the present application is a method for cleaning surfaces, during 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 liquid. The cleaning liquid is preferably aqueous and free of fluorine-containing hydrocarbon solvents.

[0085] The composition of some preferred liquid detergents or cleaners can be found in the table below (unless otherwise stated, the amounts are given in wt. % based on the total weight of the formulation). The detergents or cleaners listed do not contain fluorinated hydrocarbon solvents.

[0086]

[0087]

[0088] Recipe 6 Recipe 7 Recipe 8 Recipe 9 Compounds of formula (1) 5 to 80 10 to 70 15 to 65 20 to 60 Nonionic surfactants 5 to 50 10 to 45 15 to 40 20 to 35 <![CDATA[Polyalkoxylated amine 1) > 0.5 to 10 1 to 8 1 to 8 3 to 6 other Up to 100 Up to 100 Up to 100 Up to 100

[0089] Recipe 11 Recipe 12 Recipe 13 Recipe 14 Compounds of formula (1) 5 to 80 10 to 70 15 to 65 20 to 60 Nonionic surfactants 5 to 50 10 to 45 15 to 40 20 to 35 <![CDATA[Polyalkoxylated polyalkenimine 2) > 0.5 to 10 1 to 8 1 to 8 3 to 6 other Up to 100 Up to 100 Up to 100 Up to 100

[0090] Recipe 16 Recipe 17 Recipe 18 Recipe 19 Compounds of formula (1) 5 to 80 10 to 70 15 to 65 20 to 60 Nonionic surfactants 5 to 50 10 to 45 15 to 40 20 to 35 Phosphonates 0.5 to 10 1 to 8 1 to 8 3 to 6 other Up to 100 Up to 100 Up to 100 Up to 100

[0091] Another subject matter of the present application is a method for cleaning surfaces, during which a compound of the formula (1) or a cleaning agent containing a compound of the formula (1) is introduced into a cleaning liquid.

[0092] The compound of general formula (1) can be prepared by neutralizing the corresponding sulfonic acid with the corresponding amine. Another subject of the present application is a method for preparing the compound of general formula (1), comprising the following steps:

[0093] 1) providing a sulfonic acid of the general formula RX-SO3H (2), wherein

[0094] i) R is selected from C6 to C 20 Alkyl functional group;

[0095] ii) X is selected from the following groups

[0096] a) C6H4

[0097] b)(OC2H4) n O, wherein n=2 to 8

[0098] c)C(O)-N(CH3)CH2CH2

[0099] d) R 1 O(O)CCH2(R 1 O(O)C)CH, where R 1 =C7 to C 20 alkyl

[0100] 2) Provide the general formula N(R a R b R c )(3) an amine, wherein the functional group R a , R b and R c At least two of which are selected from C3 to C 12 Alkyl and C3 to C 12 Hydroxyalkyl functional group;

[0101] 3) The sulfonic acid (2) and the amine (3) are mixed to form a compound of the general formula (1).

[0102] As mentioned above, the compound of general formula (1) can be prepared by reacting sulfonic acid (2) with the corresponding amine (3). Therefore, preferred detergents based on compounds of general formula (1) can be described in other words by the content of sulfonic acid (2) and amine (3). The composition of some preferred detergents or cleaning agents can be obtained from the following table (unless otherwise stated, the amount is given in wt.% based on the total weight of the formulation). The listed detergents or cleaning agents do not contain fluorinated hydrocarbon solvents.

[0103] Recipe 21 Recipe 22 Recipe 23 Recipe 24 <![CDATA[R-X-SO3H(2) 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 Nonionic surfactants 5 to 50 10 to 45 15 to 40 20 to 35 other Up to 100 Up to 100 Up to 100 Up to 100

[0104] Recipe 25 Recipe 26 Recipe 27 Recipe 28 <![CDATA[R-X-SO3H(2) 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 Nonionic surfactants 5 to 50 10 to 45 15 to 40 20 to 35 Enzyme preparations 0.2 to 12 0.5 to 10 0.5 to 10 1 to 8 other Up to 100 Up to 100 Up to 100 Up to 100

[0105] Recipe 31 Recipe 32 Recipe 33 Recipe 34 <![CDATA[R-X-SO3H(2) 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 Nonionic surfactants 5 to 50 10 to 45 15 to 40 20 to 35 Detergent or cleaning active polymers 0.1 to 14 0.2 to 12 0.5 to 10 0.5 to 10 other Up to 100 Up to 100 Up to 100 Up to 100

[0106]

[0107]

[0108] Recipe 41 Recipe 42 Recipe 43 Recipe 44 <![CDATA[R-X-SO3H(2) 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 Nonionic surfactants 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 other Up to 100 Up to 100 Up to 100 Up to 100

[0109] Recipe 45 Recipe 46 Recipe 47 Recipe 48 <![CDATA[R-X-SO3H(2) 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 Nonionic surfactants 5 to 50 10 to 45 15 to 40 20 to 35 Enzyme preparations 0.2 to 12 0.5 to 10 0.5 to 10 1 to 8 water <10 <10 <7 <5 other Up to 100 Up to 100 Up to 100 Up to 100

[0110] Recipe 51 Recipe 52 Recipe 53 Recipe 54 <![CDATA[R-X-SO3H(2) 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 Nonionic surfactants 5 to 50 10 to 45 15 to 40 20 to 35 Enzyme preparations 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 other Up to 100 Up to 100 Up to 100 Up to 100

[0111] Recipe 55 Recipe 56 Recipe 57 Recipe 58 <![CDATA[R-X-SO3H(2) 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 Nonionic surfactants 5 to 50 10 to 45 15 to 40 20 to 35 Enzyme preparations 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 solvents 3 to 24 6 to 22 6 to 22 10 to 20 water <10 <10 <7 <5 other Up to 100 Up to 100 Up to 100 Up to 100

[0112] Recipe 61 Recipe 62 Recipe 63 Recipe 64 <![CDATA[R-X-SO3H(2) 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 Nonionic surfactants 5 to 50 10 to 45 15 to 40 20 to 35 Enzyme preparations 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 Detergent or cleaning active polymers 0.1 to 14 0.2 to 12 0.5 to 10 0.5 to 10 Organic solvents 3 to 24 6 to 22 6 to 22 10 to 20 water <10 <10 <7 <5 other Up to 100 Up to 100 Up to 100 Up to 100

[0113] 1 X is selected from the following groups

[0114] a) C6H4

[0115] b)(OC2H4) n O, wherein n=2 to 8

[0116] c)C(O)-N(CH3)CH2CH2

[0117] d) R 1 O(O)CCH2(R 1 O(O)C)CH, where R 1 =C7 to C 20 alkyl

[0118] Preferably selected from C6H4

[0119] The compounds of the general formula (1) are particularly suitable for preparing detergent compositions with a high detergent content. In addition to the high content of sulfonic acid (2) neutralized with amine (3), these compositions are also characterized in particular by a low solvent content. Some preferred compositions in the form of highly concentrated detergent or cleaning agent products can be obtained from the following table (unless otherwise stated, the amounts are given in wt.% based on the total weight of the formulation).

[0120] The detergents or cleaning agents listed do not contain fluorinated hydrocarbon solvents.

[0121] Recipe 71 Recipe 72 Recipe 73 Recipe 74 <![CDATA[R-X-SO3H(2) 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 Nonionic surfactants 0 to 15 0 to 15 2 to 12 4 to 10 other Up to 100 Up to 100 Up to 100 Up to 100

[0122] Recipe 75 Recipe 76 Recipe 77 Recipe 78 <![CDATA[R-X-SO3H(2) 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 Nonionic surfactants 0 to 15 0 to 15 2 to 12 4 to 10 Enzyme preparations 0.2 to 12 0.5 to 10 0.5 to 10 1 to 8 other Up to 100 Up to 100 Up to 100 Up to 100

[0123] Recipe 81 Recipe 82 Recipe 83 Recipe 84 <![CDATA[R-X-SO3H(2) 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 Nonionic surfactants 0 to 15 0 to 15 2 to 12 4 to 10 Detergent or cleaning active polymers 0.1 to 14 0.2 to 12 0.5 to 10 0.5 to 10 other Up to 100 Up to 100 Up to 100 Up to 100

[0124] Recipe 85 Recipe 86 Recipe 87 Recipe 88 <![CDATA[R-X-SO3H(2) 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 Nonionic surfactants 0 to 15 0 to 15 2 to 12 4 to 10 Phosphonates 0.5 to 10 1 to 8 1 to 8 3 to 6 other Up to 100 Up to 100 Up to 100 Up to 100

[0125]

[0126]

[0127] Recipe 95 Recipe 96 Recipe 97 Recipe 98 <![CDATA[R-X-SO3H(2) 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 Nonionic surfactants 0 to 15 0 to 15 2 to 12 4 to 10 Enzyme preparations 0.2 to 12 0.5 to 10 0.5 to 10 1 to 8 water <5 <5 <3 <3 other Up to 100 Up to 100 Up to 100 Up to 100

[0128] Recipe 101 Recipe 102 Recipe 103 Recipe 104 <![CDATA[R-X-SO3H(2) 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 Nonionic surfactants 0 to 15 0 to 15 2 to 12 4 to 10 Enzyme preparations 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 other Up to 100 Up to 100 Up to 100 Up to 100

[0129]

[0130]

[0131] Recipe 111 Recipe 112 Recipe 113 Recipe 114 <![CDATA[R-X-SO3H(2) 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 Nonionic surfactants 0 to 15 0 to 15 2 to 12 4 to 10 Enzyme preparations 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 Detergent or cleaning active polymers 0.1 to 14 0.2 to 12 0.5 to 10 0.5 to 10 Organic solvents <5 <5 <3 <3 water <5 <5 <3 <3 other Up to 100 Up to 100 Up to 100 Up to 100

[0132] 2 X is selected from the following groups

[0133] a) C6H4

[0134] b)(OC2H4) n O, wherein n=2 to 8

[0135] c)C(O)-N(CH3)CH2CH2

[0136] d) R 1 O(O)CCH2(R 1 O(O)C)CH, where R 1 =C7 to C 20 alkyl

[0137] Preferably selected from C6H4

[0138] The above-mentioned detergents or cleaning agents are preferably free of quaternary amines and organic pigments.

[0139] This application provides, inter alia, the following topics:

[0140] 1. A compound of general formula (1)

[0141] RX-SO3 - HN + (R a R b R c )(1), where

[0142] i) R is selected from C6 to C 20 Alkyl functional group;

[0143] ii) X is selected from the following groups

[0144] a) C6H4

[0145] b)(OC2H4) n O, wherein n=2 to 8

[0146] c)C(O)-N(CH3)CH2CH2

[0147] d) R 1 O(O)CCH2(R 1 O(O)C)CH, where R 1 =C6 to C 20 Alkyl iii) Functional group R a , R b and R c At least two of which are independently selected from C3 to C 12 Alkyl and C3 to C 12 Hydroxyalkyl functional group.

[0148] 2. A compound of the general formula (1) according to point 1, wherein

[0149] i) R is selected from C 10 To C 13 Alkyl functional group;

[0150] ii) X is selected from the group C6H4

[0151] iii) Functional group R a , R b and R c At least two of which are independently selected from C3 to C 12 Alkyl and C3 to C 12 Hydroxyalkyl functional group.

[0152] 3. A compound of the general formula (1) according to point 2, wherein

[0153] i) R is selected from a linear C 10 To C 13 Alkyl functional group.

[0154] 4. A compound of formula (1) according to one of points 2 or 3, wherein

[0155] i) R is selected from secondary C 10 To C 13 Alkyl functional group.

[0156] 5. A compound of the general formula (1) according to any one of points 2 to 4, wherein

[0157] i) R is selected from the group consisting of linear secondary C 10 To C 13 Alkyl functional group.

[0158] 6. A compound of the general formula (1) according to any one of points 2 to 5, wherein

[0159] i) R represents a straight chain C 12 -H 25 Alkyl functional group.

[0160] 7. A compound of the general formula (1) according to any one of points 2 to 6, wherein

[0161] i) R represents a straight chain secondary C 12 H 25 Alkyl functional group.

[0162] 8. A compound of the general formula (1) according to point 1, wherein

[0163] i) R is selected from C 12 To C 20 Alkyl functional group;

[0164] ii) X is selected from the group (OC2H4)n O, wherein n=1 to 8

[0165] iii) Functional group R a , R b and R c At least two of which are independently selected from C3 to C 12 Alkyl and C3 to C 12 Hydroxyalkyl functional group.

[0166] 9. A compound of the general formula (1) according to point 1, wherein

[0167] i) R is selected from C7 to C 17 Alkyl functional group;

[0168] ii) X is selected from the group C(O)-N(CH3)CH2CH2;

[0169] iii) Functional group R a , R b and R c At least two of which are independently selected from C3 to C 12 Alkyl and C3 to C 12 Hydroxyalkyl functional group.

[0170] 10. The compound of general formula (1) according to point 1, wherein

[0171] i) R is selected from C7 to C 17 Alkyl functional group;

[0172] ii) X is selected from the group O(O)CCH2(RO(O)C)CH, wherein R=C6 to C 17 alkyl;

[0173] iii) Functional group R a , R b and R c At least two of which are independently selected from C3 to C 12 Alkyl and C3 to C 12 Hydroxyalkyl functional group.

[0174] 11. A compound of formula (1) according to any of the preceding points, wherein

[0175] i) Functional group R a , R b and R c At least two of which are independently selected from C3 to C 12 The alkyl functional group is preferably selected from C3 to C6 alkyl functional groups.

[0176] 12. A compound of formula (1) according to any of the preceding points, wherein

[0177] iii) Three functional groups R a , R b and R c independently selected from C3 to C 12 The alkyl functional group is preferably selected from C3 to C6 alkyl functional groups.

[0178] 13. A compound of the general formula (1) according to any one of points 1 to 10, wherein

[0179] iii) Functional group R a , R b and R c At least two of which are independently selected from C3 to C 12 The hydroxyalkyl functional group is preferably selected from C3 to C6 hydroxyalkyl functional groups.

[0180] 14. A compound of the general formula (1) according to any one of points 1 to 10 or 13, wherein

[0181] iii) Three functional groups R a , R b and R c independently selected from C3 to C 12 The hydroxyalkyl functional group is preferably selected from C3 to C6 hydroxyalkyl functional groups.

[0182] 15. A compound of the general formula (1) according to any one of points 1 to 10, 13 or 14, wherein

[0183] iii) Three functional groups R a , R b and R c Each represents a (CH2CH(OH)CH3)hydroxyalkyl functional group.

[0184] 16. The compound of general formula (1) according to point 1, wherein

[0185] i) R represents a straight chain C 12 H 25 Alkyl functional group;

[0186] ii) X is selected from the group C6H4

[0187] iii) R a , R b and R c Each represents a (CH2CH(OH)CH3)hydroxyalkyl functional group.

[0188] 17. The compound of general formula (1) according to point 1, wherein

[0189] i) R represents a straight chain secondary C 12 H 25 Alkyl functional group;

[0190] ii) X is selected from the group C6H4

[0191] iii) R a , R b and R c Each represents a (CH2CH(OH)CH3)hydroxyalkyl functional group.

[0192] 18. A detergent or cleaning agent containing a compound of the general formula (1) according to any one of the preceding points.

[0193] 19. A liquid detergent or cleaner containing a compound of the general formula (1) according to any one of the preceding points.

[0194] 20. The detergent or cleaning agent according to one of points 18 or 19, wherein the detergent or cleaning agent does not contain fluorine-containing hydrocarbon solvents.

[0195] 21. A method for washing textiles, during which a compound of the general formula (1) according to one of points 1 to 17 or a detergent or cleaning agent according to point 18 is introduced into the washing liquor or applied to the textile surface.

[0196] 22. The method according to point 21, wherein the washing liquid does not contain fluorine-containing hydrocarbon solvents.

[0197] 23. The method according to one of points 21 or 22, wherein the washing liquid is aqueous.

[0198] 24. A method for cleaning hard surfaces, during which a compound of the 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 liquid or applied to the hard surface.

[0199] 25. The method according to point 24, wherein the cleaning liquid does not contain fluorine-containing hydrocarbon solvents.

[0200] 26. The method according to one of points 24 or 25, wherein the cleaning liquid is aqueous.

[0201] 27. A method for preparing a compound of general formula (1) according to any one of points 1 to 17, comprising the following steps

[0202] 1) providing a sulfonic acid of the general formula RX-SO3H (2), wherein

[0203] i) R is selected from C6 to C 20 Alkyl functional group;

[0204] ii) X is selected from the following groups

[0205] a) C6H4

[0206] b)(OC2H4) n O, wherein n=2 to 8

[0207] c)C(O)-N(CH3)CH2CH2

[0208] d) R 1 O(O)CCH2(R 1 O(O)C)CH, where R = C7 to C 20 alkyl

[0209] 2) Provide the general formula N(R a R b R c )(3) an amine, wherein the functional group R a , R b and R c At least two of which are selected from C3 to C 12 Alkyl and C3 to C 12 Hydroxyalkyl functional group;

[0210] 3) The sulfonic acid (2) and the amine (3) are mixed to form a compound of the general formula (1). Example

[0211] Dodecylbenzenesulfonic acid and triisopropanolamine in equal molar amounts are reacted with each other in a reaction vessel. The formation formula is C 12 H 25 -C6H4-SO3 - HN + A transparent, viscous, surface-active ionic liquid of (CH2CH(OH)CH3)3.

[0212] The optical properties of the neutralization products of dodecylbenzenesulfonic acid with triisopropanolamine (according to the invention) and monoisopropanolamine (not according to the invention) were investigated using polarizing microscopy:

[0213] <h2 style=";text-align:left;direction:ltr"><![CDATA[C <h2 style=";text-align:left;direction:ltr"> 12 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 25 <h2 style=";text-align:left;direction:ltr"> -C6H4-SO3<h2 style=";text-align:left;direction:ltr"> - <h2 style=";text-align:left;direction:ltr"> HN<h2 style=";text-align:left;direction:ltr"> + <h2 style=";text-align:left;direction:ltr"> (CH2CH(OH)CH3)3]]><h2 style=";text-align:left;direction:ltr"> <![CDATA[C 12 H 25 -C6H4-SO3 - H3N + CH2CH(OH)CH3]]> Amorphous, isotropic Liquid crystal, anisotropy

[0214] Rheological studies of the neutralization products of dodecylbenzenesulfonic acid with triisopropanolamine (according to the invention) and monoisopropanolamine (not according to the invention) gave the following results:

[0215] <h2 style=";text-align:left;direction:ltr"><![CDATA[C <h2 style=";text-align:left;direction:ltr"> 12 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 25 <h2 style=";text-align:left;direction:ltr"> -C6H4-SO3<h2 style=";text-align:left;direction:ltr"> - <h2 style=";text-align:left;direction:ltr"> HN<h2 style=";text-align:left;direction:ltr"> + <h2 style=";text-align:left;direction:ltr"> (CH2CH(OH)CH3)3]]><h2 style=";text-align:left;direction:ltr"> <![CDATA[C 12 H 25 -C6H4-SO3 - H3N + CH2CH(OH)CH3]]> No pour point Pour Point Viscosity is independent of shear rate Viscosity depends on shear rate

[0216] Thermal analysis of the neutralization products of dodecylbenzenesulfonic acid with triisopropanolamine (according to the present invention) and monoisopropanolamine (not according to the present invention) by differential scanning calorimetry (DSC) gave the following results:

[0217] <h2 style=";text-align:left;direction:ltr"><![CDATA[C <h2 style=";text-align:left;direction:ltr"> 12 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 25 <h2 style=";text-align:left;direction:ltr"> -C6H4-SO3<h2 style=";text-align:left;direction:ltr"> - <h2 style=";text-align:left;direction:ltr"> HN<h2 style=";text-align:left;direction:ltr"> + <h2 style=";text-align:left;direction:ltr"> (CH2CH(OH)CH3)3]]><h2 style=";text-align:left;direction:ltr"> <![CDATA[C 12 H 25 -C6H4-SO3 - H3N + CH2CH(OH)CH3]]> Glass transition temperature Glass transition temperature and melting point

[0218] An exemplary detergent composition containing a compound of the general formula

[0219] Element Wt.% <![CDATA[Ethoxylated C 12 -C 18 -fatty alcohol (7EO)]]> 30 <h2 style=";text-align:left;direction:ltr"><![CDATA[C <h2 style=";text-align:left;direction:ltr"> 12 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 25 <h2 style=";text-align:left;direction:ltr"> -C6H4-SO3<h2 style=";text-align:left;direction:ltr"> - <h2 style=";text-align:left;direction:ltr"> HN<h2 style=";text-align:left;direction:ltr"> + <h2 style=";text-align:left;direction:ltr"> (CH2CH(OH)CH3)3]]><h2 style=";text-align:left;direction:ltr"> 48 <![CDATA[Polyalkoxylated amine 1) > 6 <![CDATA[Polyalkoxylated polyalkenimine 2) > 6 DTPMP 5 other Up to 100

[0220] 1) Weight average molecular weight M w Polyalkoxylated amines in the range of 600 g / mol to 10000 g / mol, obtained by reacting ammonia or primary alkylamines or hydroxyalkylamines having a molecular weight of less than 200 g / mol with alkylene oxides.

[0221] 2) Polyalkoxylated polyalkylene imine obtained by reacting a polyalkylene imine with an alkylene oxide.

Claims

1. A compound of general formula (1) RX-SO3 - HN + (R a R b R c )(1), where e) R is selected from C6 to C 20 Alkyl functional group; ii) X is selected from the following groups a) C6H4 b)(OC2H4) n O, wherein n=2 to 8 c)C(O)-N(CH3)CH2CH2 d) R 1 O(O)CCH2(R 1 O(O)C)CH, where R 1 =C6 to C 20 alkyl iii) Functional group R a , R b and R c At least two of which are independently selected from C3 to C 12 Alkyl and C3 to C 12 Hydroxyalkyl functional group.

2. The compound of general formula (1) according to claim 1, wherein i) R is selected from C 10 To C 13 Alkyl functional group; ii) X is selected from the group C6H4 iii) Functional group R a , R b and R c At least two of which are independently selected from C3 to C 12 Alkyl and C3 to C 12 Hydroxyalkyl functional group.

3. A compound of the general formula (1) according to any one of the preceding claims, wherein i) R represents a straight chain secondary C 12 H 25 Alkyl functional group.

4. A compound of the general formula (1) according to any one of the preceding claims, wherein iii) Three functional groups R a , R b and R c independently selected from C3 to C 12 The hydroxyalkyl functional group is preferably selected from C3 to C6 hydroxyalkyl functional groups.

5. A compound of the general formula (1) according to any one of the preceding claims, wherein i) R represents a straight chain C 12 H 25 Alkyl functional group; ii) X is selected from the group C6H4 iii) R a , R b and R c Each represents a (CH2CH(OH)CH3)hydroxyalkyl functional group.

6. A compound of the general formula (1) according to any one of the preceding claims, wherein Oi)R represents a straight chain secondary C 12 H 25 Alkyl functional group; Oii) X is selected from the group C6H4 iii) R a , R b and R c Each represents a (CH2CH(OH)CH3)hydroxyalkyl functional group.

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

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

9. A method for cleaning hard surfaces, during which a compound of the general formula (1) according to one of claims 1 to 6 or a detergent or cleaning agent according to claim 7 is introduced into a cleaning liquid or applied to the hard surface.

10. A method for preparing a compound of the general formula (1) according to any one of claims 1 to 7, comprising the following steps: 1) providing a sulfonic acid of the general formula RX-SO3H (2), wherein i) R is selected from C6 to C 20 Alkyl functional group; ii) X is selected from the following groups a) C6H4 b)(OC2H4) n O, wherein n=2 to 8 c)C(O)-N(CH3)CH2CH2 d) R 1 O(O)CCH2(R 1 O(O)C)CH, where R = C6 to C 20 alkyl 2) Provide the general formula N(R a R b R c )(3) an amine, wherein the functional group R a , R b and R c At least two of which are selected from C3 to C 12 Alkyl and C3 to C 12 Hydroxyalkyl functional group; 3) The sulfonic acid (2) and the amine (3) are mixed to form a compound of the general formula (1).

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