MXPA00004323A - Diester amine adducts - Google Patents

Abstract

Described are diester amine adducts of formula (1) wherein R1, R2, R3, R4 are each independently of one another C4-C22alkyl;C2-C22alkenyl;or C5-C7cycloalkyl;X1 and X2 are each independently of the other hydrogen, C1-C4alkyl;C2-C4hydroxyalkyl or C2-C4hydroxyhaloalkyl;Y is a radical of formula (1b);A1 is C2-C3alkylene or 2-hydroxy-n-propylene;X3 is hydrogen;C1-C4alkyl, C2-C4hydroxyalkyl;or C2-C4hydroxyhaloalkyl;(A) is an asymmetrical carbon atom in the R- or S-configuration, wherein, if C1=R, C2=R;C1=S, C2=S;and C1=R;C2=S;m1 is 1 or 2;and n is an integer from 1 to 4;p is 0 or 1;which adducts may be in the form of free bases or ammonium salts. Said compounds are precursors of compounds having good complex-forming properties and are thus able to effectively bind heavy metal ions such as iron, zinc, magnesium or copper ions and to prevent metal-initiated oxidations after enzymatic or chemical cleavage. They have a plurality of uses, for example in foods, beverages, derusting and decalcification baths, as additives in liquids for cooling-water circuits, in personal-care products,as bleaching stabilizers, in cleaning agents and detergents, in the textile industry and also as soft handle agents for organic fibre materials.

Description

ADUCTS D? AMINA DE DIESTER The present invention relates to diester amine adducts, with a process for the preparation of those compounds and their use. The diester amine adducts of this invention correspond to the formula where R x, R 2, R 3, R 4 are each independently of the other C-C 22 alkyl; C2-C22 alkenyl; or C5-C7 cycloalkyl; Xi and X2 are each independently of the other hydrogen, C1-C4 alkyl; C2-C4 hydroxyalkyl or C2-C4 hydroxyhaloalkyl; Y is a radical of formula (Ib) Ai is C2-C3 alkylene or 2-hydroxy-n-propylene; X3 is hydrogen; C 1 -C 4 alkyl, C 2 -C 4 hydroxyalkyl; or C2-C4 hydroxyhaloalkyl; is an asymmetric carbon atom in the R or S configuration, where, if J = R, C2 = R; CX = S, C2 = S; and C ^ R; C2 = S; i is 1 or 2; and n is a term of 1 to 4; p is 0 or 1; adduct which may be in the form of a free base, acid, acid salt or quaternary ammonium salt. The diester amine adducts are stereochemically uniform compounds in the (SS) -, (RR) - or (RS) - configuration, ie compounds which may be represented by the formulas (the) configuration (SS))) (lb) (configuration (RR)); or : ic) [configuration (RS)) The C?-C22 alkyl is a straight or branched chain alkyl radical, for example methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, amyl, isoamyl or tert-amyl, heptyl , octyl, isooctyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl or octadecyl or eicosyl. The C2-C22 alkenyl is, for example, allyl, methallyl, isopropenyl, 2-butenyl, 3-butenyl, isobutenyl, n-penta-2,4-dienyl, 3-methyl-but-2-enyl, n-oct -2-enyl, n-dodec-2-enyl, iso-dodecenyl, n-dodec-2-enyl or n-octadec-4-enyl. The C5-C7 cycloalkyl is typically cyclopentyl, cycloheptyl or, preferably, cyclohexyl. The hydroxy alkyl of C2-C is, for example, 2-hydroxyethyl or 4-hydroxy-n-butyl. The C2-C4 hydroxyhaloalkyl is typically 1-chloro-2-hydroxyethyl. Preferred diester amine adducts of formula (1) are those, wherein Ai is C2-C3 alkylene; m is 2; and p is 0. Particularly preferred diester amine adducts of formula (1) are those, wherein Xi and X2 are hydrogen and particularly preferably those, wherein Ri, R2, R3 and R are C4-C22 alkyl. The examples of diester diamine adducts of this invention are the compounds of formulas The novel diester amine adducts, which are stereochemically uniform with respect to the C1 and C2 atoms (see formula (1)), are prepared by methods known per se by reacting an amino-dicarboxylic acid of the formula OH (ld) C ???? NH I HO with an excess of the relevant alcohol under the action of gaseous HCl or thionyl chloride in a reaction in a container. Such a process is described, inter alia, in C.A. 62, 11911g (1965). The corresponding diester amine adducts can be converted to the corresponding diester amine adducts of formula (1) by reacting the resulting aminodicarboxylates of formula O-R, 0 = 5 (le) C-WS? NH I X, R20 with a dihalogen compound of formula The total course of the reaction can be represented as follows: 0-RO (1d) C- ~ N + R-QH (1e) C- ^ NX, * 1 or RO + 1/2 Hal- (A,) m., - Hal The tetraesters which are stereochemically uniform with respect to the structural amino carboxylic acid can also be obtained by reacting, for example, the diaminotetracarboxylic acid of formula (lg) or the salts of this acid with thionyl chloride and an alcohol to the corresponding ester compound of formula (I): + ti'onyl chloride Thionyl chloride is usually added by dripping at a temperature in the range of -70 to 80 °, preferably -10 to 30 ° C. In the additional course of the reaction the temperature rises to 200 ° C, the preferred temperature range is 40 to 80 ° C. Thionyl chloride is usually used in excess. At first, the thionyl chloride can also be replaced with hydrogen chloride gas. After completing the reaction, the chlorohydrides of the tetraesters can, if required, be isolated in the form of crystalline compounds and then recrystallized. The alcohol component is used as a solvent for the reaction (in large excess). The starting compound may be a tetracarboxylic acid containing water, for example EDDS having a water co-entry of about 20%. The monoesters of aminodicarboxylic acid can be obtained in good yields by commonly known processes by reacting carboxylic acid with the relevant alcohol. Mixtures of compounds of formulas (la), (lb) and (le) are obtained by first esterifying maleic anhydride with an alcohol to the corresponding diester and then reacting 2 moles of respective diester with diamine. For many applications it is also possible to replace stereochemically uniform products with mixtures of the stereoisomers of formulas (la), (lb) and (le) which are also obtained in the above manner. The stereochemically uniform compounds of formula (1) and their diester amine adducts of formula they are precursors of compounds that have pronounced complexing properties. Under physiological conditions, ester groups can be divided by esterases. The chemical hydrolysis is carried out in an aqueous medium in the presence of OH "or H + ions. The compounds are obtained, where R? = R2 = R3 = R4: = H, for example N, W-ethylenediamine disuccinic acid (EDDS). Such compounds are thus capable of effectively binding to heavy metal ions such as iron, zinc, magnesium or copper ions and preventing oxidation initiated by metals, in contrast to free acids or salts of the acids (R? = R2 = R3 = R = H), the compounds of formula (1) are easily soluble in organic solvents, fats or oils, thus obtaining new fields of application Such compounds are therefore suitable as additives in foodstuffs and beverages which are susceptible to oxidation and which are inclined to mold or rancidity Foods susceptible to oxidation are, in particular, compounds or compositions containing olefinic double bonds Due to their complex formation properties s, the novel diester amine adducts can also be used to remove undesirable calcium deposits, boiler scale and rust. They are usually used for this purpose in alkaline anti-rust and decalcification baths. The novel compounds are also used as additives in liquids for cooling water circuits to prevent and dissolve calcium deposits. The novel adducts are also used in personal care products, for example in creams, lotions, body care products, such as deodorants, soaps or shampoos and ointments, to prevent oxidation, rancidity, turbidity and the like. It is also possible to achieve, in particular, a soft touch effect on the hair.

In addition, the novel diamine adducts are used as bleacher stabilizers, for example, sodium perborate, in detergents or in the bleaching of textiles or paper. Traces of heavy metals, for example iron, copper or magnesium, are present in detergent formulations, in water and in textile or paper materials and catalyze the degradation of sodium perborate as well as other bleaches present in the detergent. The novel compounds bind to these metal ions and prevent the undesirable degradation of the bleaching system during storage of the corresponding detergent as well as in the wash liquor. The effectiveness of the bleaching system is improved and the damage of the fiber is prevented. In addition, other sensitive detergent components, such as enzymes, fluorescent whitening agents and fragrances are advantageously protected against oxidative degradation. The novel adducts can also be used in cleaning agents and detergents to remove metal ions and as preservatives. In liquid cleaning formulations, the novel compounds can be advantageously used in a concentration of 0.05 to 15% by weight, based on the total weight of the formulation.

The novel diester amine adducts can also be used advantageously in the textile industry to remove traces of heavy metals during production and when staining natural and synthetic fibers. They prevent staining and streaking on the textile material, poor wettability and lack of uniformity. The novel diester amine adducts of formula (1) are also very suitable as softening agents for organic fiber materials such as paper or in particular, textile fiber materials. Particularly good softness effects are achieved in the case of loose fibers, yarns, in particular knitted fabrics or natural cellulose fabrics, for example cotton, or polyacrylonitrile. These adducts can also be used to impart softness to the touch to fibrous materials of synthetic polyamides or regenerated cellulose. Good softness effects are obtained in fabric coatings of 0.1 to 1%, preferably 0.2 to 0.6%. The treatment of fibers is effected by the treatment of fibrous materials, preferably with an aqueous formulation, for example with an aqueous solution or emulsion of these adducts, by applying the adducts to the fibers and then drying them. It is convenient to use an emulsion or solution of 0.5 to 5%, preferably 1 to 3%, of a c. 20%, based on the weight of the fibrous materials to be finished. Aqueous formulations can be applied to the fibers by impregnation processes currently used in the industry (eg, filler or exhaust processes). The solutions in organic solvents are also used via spray. In the same way it is possible to treat paper networks with the novel adducts by means of a dew or dip process, which also results in a soft and flexible soft touch. The adducts. of novel diester amine of formula (1) can also be used as antistatic agents for textiles, in particular for polyester fabrics. In the paper industry, novel compounds can be used for the removal of hard metal ions / iron. The depositions of iron on the resulting paper are called hot marks as soon as the catalytic, oxidative degradation of the cellulose raw materials. The novel diester amine adducts are also suitable as catalysts for organic synthesis, such as for the aerial oxidation of paraffins or the hydroformylation of olefins to alcohols. The novel diester amine adducts can also be used in any desired form, for example as a powder, granulate, paste, liquid formulation, tablet, capsule, pill, suspension or gel.

If the novel adducts are used for example as body care products, then such a product comprises 0.01 to 15, preferably 0.5 to 10% by weight, based on the total weight of the composition of the diester amine adducts of formula (1) or (2) as well as cosmetically compatible adjuvants. Depending on the presentation of the shape of the body care products, this comprises other components in addition to the diester amine adduct, for example sequestrants, colorants, perfumed oils, thickeners or consistency regulators, emollients, UV absorbers, protectants. the skin, antioxidants, additives that provide the mechanical properties, such as dicarboxylic acid and / or the salts of Al, Zn, Ca, Mg fatty acid of C? 4-C22- Due to its good solubility in oil and alcohol, the Novel diester amine adducts can be incorporated into the corresponding formulations without any difficulty. A soap has, for example, the following composition: 0.01 to 5% by weight of the compound of formula (1) or (2), 0.3 to 1% by weight of titanium dioxide, 10% by weight of stearic acid, add soap base up to 100%, for example the sodium salts of fatty acid of bait and of coconut fatty acid or glycerols. A shampoo has, for example, the following composition: 0.01 to 5% by weight of the compound of formula (1) or (2), 12.0% by weight of sodium lauryl-2-sulfate, 4.0% by weight of cocamidopropyl betaine, 3.0 % by weight of NaCl, and add water up to 100%. A deodorant has, for example, the following composition: 0.01 to 5% by weight of the compound of formula (1) or (2), 60% by weight of ethanol, 0.3% by weight of perfumed oil, and adding water up to 100. %. The following non-limiting Examples illustrate the invention in more detail. The SS-DDS used has a water content of approximately 20%.

Example 1: R, S] -ethylenediamine disuccinic acid tetraethyl ester. Ethanol (300 g, 6.5 mol) and [S, S] -ethylenediamine disuccinic acid (21.92 g, 0.075 mol) were added in a vessel and thionyl chloride was added dropwise. (53.0 g, 0.45 mol) at -5 to 5 ° C. The reaction mixture was slowly warmed to room temperature and stirred for 24 h at room temperature. Subsequently, it was heated for another 12 h at 60 ° C. The suspension first became a solution and after some time the tetraester was separated as a hydrochloride in the form of white crystals. The suspension was diluted with 100 ml of ethanol and concentrated on a rotary evaporator at 60 ° C. The white residue was suspended in 100 g of a 1: 1 ice / ammonia solution mixture (25%). The aqueous phase was extracted twice with methyl-tert-butyl ether (300 ml). The organic phases were combined and then washed with water until neutral and dried over Na 2 SO. Removal of the solvent under vacuum (60 ° C) gave the lightly contaminated tetraester of formula (101) as a colorless liquid. The mixture can be purified by column chromatography (silica gel G60, ethyl acetate / petroleum ether [40/60] 8: 2).

Yield: 20.4g, 67% of the theoretical XH NMR (200MHz, CDC13, TMS): d = 1.15-1.25 (m, CH3, 6H), 2.0 (s, NH, 1H), 2.52-2.85 (m, NCCH2COO and CH2N , 4H), 3.6 (t, NCH, 1H), 4.07-4.25- (m, CH2CH3, 4H). 13C NMR (200MHz, CDC13, TMS): d = 14.48 (CH3), 14.54 (CH3), 38.42 (CH2), 47.52 (CH2), 57.79 (CH), 60.98 (CH2), 61.31 (CH2), 171.19 (Cc) ), 173.88 (Cc). (101) configuration [S, S] Example 2: Hydrolysis of the tetraether ester of S, S] -ethylenediaminodisuccinic acid to EDDS The [S, S] -EDDS-tetraethyl ester (1.00 g, 0.00247 mol) was suspended in 50 ml of water and placed in a thermostat a 95 ° C. Using a pH controller, the pH remained constant at 9.5-10 (lN-NaOH). 24 H later, another 50 ml of water was added and the mixture was concentrated to approximately 40 ml in a rotary evaporator at 80 ° C. The residue was transferred to a 50 ml measuring flask, filled to the calibration mark with water and the pH adjusted = 9.5. The molar specific amount of the hydrolyzate is [a] 20D = -14.5. The specific amount of rotation for a solution of the trisodium [S, S] -EDDS salt prepared from the acid L-aspartic and dibromoethane is [] 20D = -15.9 (pH = 9.5) The specific amount of rotation for a solution of the salt of [S, S] -EDDS trisodium placed in a thermostat for 24 h at pH = 9.5-10 a 95 ° C is [a] 20D = -13.8 (pH = 9.5). These measurements show that the configuration of the asymmetric carbon atoms in the EDDS structure is strongly charged by the previous esterification method.

Example 3: [S, S] - / [R, R] - / [R, S] -ethylenediamine disuccinic acid (isomer mixture) tetraisooctylic ester Maleic anhydride (10.1 g), 2-ethyl-1-hexanol ( 28.7 g) and 2. ß-di (tert-butyl) -p-cresol (0.1 g) and heated to 90 ° C. 2h later, 50 ml of benzene and 0.6 g of concentrated sulfuric acid were added. The nitrogen passed through it and the benzene and water were distilled azeotropically. After cooling, the mixture was charged with 2.6 g of powdered sodium carbonate and stirred for 30 min. The undissolved component of the reaction mixture was removed by filtration and the filtrate was concentrated on a rotary evaporator under vacuum to give 38 g of the crude diester of formula (103). Distillation under high vacuum gave the diester of formula (103a) with a yield of 90% of the theoretical, Elementary analysis: % C > Calculated H: 70.55 10.66 found: 70.7 10.9 After loading 100 ml of toluene with the diester of formula (103) (27.24 g, 0.08 mol), ethylenediamine (2.4 g, 0.04 mol, dissolved in 5 ml of toluene) was added dropwise at 20-25 ° C and the mixture was heated for 4 h at 80 C. The solvent was removed on a rotary evaporator under vacuum. The residue was purified by column chromatography (silica gel 60 / toluene / ethyl acetate 7: 3).

Yield: 9.0 g, 30% of theory (yellowish liquid) Elementary analysis: % C H ^ N calculated: 68.07 10.88 3.7! found: 68.2 10.8 3.7 mixture of the isomers [S, S] -, '[S, R] - and [R, R] Example 4: [S, S] -ethylenediamine disuccinic acid tetraisooctyl ester. 2-Ethyl-1-hexanol (100 g, 0.77 mol) was placed in a vessel and thionyl chloride (28.4 g, 0.24 mol) was added dropwise to - 5 to 5 ° C. Portions of [S, S] -ethylenediamine disuccinic acid (11.68 g, 0.04 mol) were added to the reaction mixture. The reaction mixture was slowly warmed to room temperature and stirred for 12 h at room temperature. Subsequently, the mixture was heated for a further 24 h at 60 ° C and then stirred for 48 h at room temperature. The reaction mixture was then added, with stirring, to a mixture of an ice / ammonia solution and worked up as described in Example 1. To remove 2-ethyl-1-hexanol, the organic phase was concentrated under high empty. This gave a yellowish powder corresponding to formula (104) of the slightly contaminated tetraester (21 g, 73% of theory). The product can be purified by column chromatography (silica gel G60, ethyl acetate / petroleum ether [40/60] 1: 1). aH NMR (200MHz, CDC13, TMS): d = [0.72-0.90 (m), 1.11-1.27 (m), 1.40-1.59 (m) alkyl radical, 30H], 1.91 (s, NH, 1H), 2.49- 2.80 (m, NCCH2COO and CH2N, 4H), 3.57 (t, NCH, 1H), 3.88-4.10 (m, CH20, 4H). 13C NMR (200MHz, CDC13, TMS): d = 11.29, 11.47, 14.39, 2 .33, 23.74, 24.07, 24.10, 29.27, 29.51, 30.53, 30.71, 38.48, 39.06, 39.09, 47.67, 57.83 (CH), 67.53 (CH2), 67.72 (CH2), 171.40 (Cc), 174.08 (Cc) configuration [S, S] Example 5: [S, S] -ethylenediaminodisuccinic acid tetrisopropyl ester Isopropanol (150.0 g, 2.5 mol) was placed in a vessel and thionyl chloride (14.3 g, 0.12 mol) was added dropwise at -5 to 5 ° C. . Portions of [S, S] -ethylenediaminesuccinic acid (5.84 g, 0.02 mol) were added to the reaction mixture. The reaction mixture was heated slowly to room temperature and then for about 24 h at 60 ° C. The tetraester hydrochloride crystals of formula (105) formed after cooling, which were collected by filtration and washed with 50 ml of methyl tert-butyl ether. After stirring the filter cake in a mixture of the ice / ammonia solution, work was carried out as described in Example 1. The removal of the oil under vacuum (60 ° C) gave the lightly contaminated tetraester in the form of a yellowish oil (yield: 1.71 g (19% of theory) .The product can be purified by column chromatography (silica gel G60, ethyl acetate / petroleum ether [ 40/60] / ethanol (9: 1: 0.5). 1H NMR (200MHz, CDC13, TMS): d = 1.15-1.38 (m, CH3, 12H), 1.99 (s, NH, 1H), 2.54-2.85 NCCH2COO and CH2N, 4H), 3.58 (t, NCH, 1H), 4.93-5.12 (m, OCH, 2H). 13C NMR (200MHz, CDCI3, TMS): d = 22.11 (CH3), 22.15 (CH3), 22.21 ( CH3), 38.72 (CH2), 47.60 (CH2), 57.99 (CH), 68.41 (CH), 68.85 (CH), 170.72 (Cc), 173.41 (Cc) (ios; configuration [S, S] Example 6: [S, S] -ethylenediamine disuccinic acid tetrabutyl ester. N-Butanol (200 g, 2.7 mol) was placed in a vessel and thionyl chloride (14.3 g, 0.12 mol) was added dropwise to -5 to 5. ° C. [S, S] -ethylenediaminedisuccinic acid (5.84 g, 0.02 mol) was added portionwise to the reaction mixture. The reaction mixture was slowly heated to room temperature and then for a further 48 h at 60 ° C. The suspension first became a solution and after some time the tetraester was separated as a hydrochloride in the form of white crystals. The mixture was cooled to room temperature and, after the addition of 50 ml of methyl tert-butyl ether, was filtered. The filter cake was heated with 50 ml of methyl tert-butyl ether and dried briefly by suction. After stirring the filter cake in an ice / ammonia solution, the work was carried out as described in Example 1, giving the tetraester of formula (106) as a slightly yellowish liquid. Yield: 5.0 g (48.45% of theoretical) 1ti NMR (200MHz, CDC13, TMS): d = 0.80-0.95 (m, CH3, 6H), 1.22-1.41 (m, alkyl-CH2, 4H), 1.48-1.6. 5 (m, alkyl-CH2, 4H), 1.94 (s, NH, 1H), 2.59-2.81 (m, NCCH2C00 and CH2N, 4H), 3.57 (t, NH, 1H), 3.98-4.16 (m, OCH2) . 13C NMR (200MHz, CDC13, TMS): d = 13.99 (CH3), 19.42 (CH2), 19.61 (CH2), 30.94 (CH2), 30.95 (CH2), 38.44 (CH2), 47.56 (CH2), 57.79 (CH ), 64.88 (CH2), 65.17 (CH2), 171.26 (Cc), 173.94 (Cc). configuration [S, S] Example Tetra- (2-butyl) isis] ethylenediamine disuccinic acid 2-Butanol acid (200 g, 2.7 mol) was placed in a vessel and thionyl chloride (14.3 g, 0.12 mol) was added dropwise at -5 to 5 ° C. . Portions of [S, S] -ethylenediamine disuccinic acid (5.84 g, 0.02 mol) were added to the reaction mixture. The reaction mixture was heated slowly to room temperature and then stirred for another 48 h at 60 ° C. The mixture was then heated to 80 ° C and maintained for 16 h at this temperature. The clear, colorless solution was cooled to 2 ° C until the tetraester was separated as a hydrochloride in the form of white crystals. The mixture was filtered at 5 ° and the product was washed with 50 ml of methyl-tert-butyl ether. After stirring the filter cake in an ice / ammonia solution, the work was carried out as described in Example 1. The tetraester of formula (107) is obtained in the form of a slightly yellowish oil (yield: 0.9 g. , 9% of theory) and can be purified by column chromatography (silica gel G60, ethyl acetate / petroleum ether [40/60] 8: 2) to give a colorless oil. 1H NMR (200MHz, CDC13, TMS): d = 0.88-0.98 (m, CH2CH3, 6H), 1.10-1.28 (m, CHCH3, 6H), 1.42-1.68 (m, CH2CH3, 4H), 1.98 (s, NH , 1H), 2.52-2.88 (m, NCCH2COO and CH2N, 4H), 3.60 (t, NCH, 1H), 4.78-4.96 (m, CH2N, 2H). 13C NMR (200MHz, CDC13, TMS): d = 10.46 (CH3), 10.51 (CH3), 20.17 (CH3), 20.28 (CH3), 29.54 (CH2), 29.56 (CH2), 39.18 (CH2), 48.1 (CH2) ), 58.53 (CH), 73.39 (CH), 73.88 (CH), 171.30 (Cc) 174.01 (Cc). (107; configuration [H.H] Example 8: [S, S] -ethylenediaminodisuccinic acid tetra (isobutyl) ester Isobutanol (200 g, 2.7 mol) was placed in a vessel and then thionyl chloride (14.3 g, 0.12 mol) was added dropwise to -5 a 5 ° C. [S, S] -ethylenediamine disuccinic acid (5.84 g) portions were added, 0.02 mol) to the reaction mixture. The reaction mixture was slowly heated to room temperature and then stirred for a further 41 h at 60 ° C. The suspension first became a solution and after some time the tetraester was separated as a hydrochloride in the form of white crystals. The mixture was cooled to room temperature and filtered, and the filter cake was washed with 50 ml of methyl-tert-butyl ether. After stirring the filter cake in ice / ammonia solution, the mixture was worked up as in Example 1. The tetraester of formula (108) was obtained as a slightly yellow oil (yield: 6.8 g, 66% of theoretical ) and can be purified by column chromatography (silica gel G60, ethyl acetate / petroleum ether [40/60] 8: 2) to give a colorless oil. XH NMR (200MHz, CDC13, TMS): d = 0.84-1.01 (m, CH3, 12H), 1.84-2.08 (m, NH and CH3CH, 3H), 2.55-2.88 (m, NCCH2COO and CH2N, 4H), 3.65 (t, NCH, 1H), 3.84-3.96 (m, QCH2, 4H). 13C NMR (200MHz, CDC13, TMS): d '= 18.39 (CH3), 26.99, 27.03, 37.43 (CH2), 46.61 (CH2), 56.80 (CH), 70.15 (CH2), 70.41 (CH2), 170.24 (Cq ), 172.92 (CC) (108) configuration [H.H] Example 9: Microbiological test Medium: Casein agar, soybean meal and peptone (Merck) Casein broth, soybean meal and peptone (Merck) Test germs: Staphylococcus aureus ATCC 9144 Corynebacterium xerosis ATCC 373 t Escherichia coli NCTC 8196 Preparation of germ suspensions: Test germs were grown overnight (approximately 18 h) at 37 ° C in Broth Broth (5 ml test tubes). The germ count of the night culture was determined by the spiralometer method and was between 108 -109 KBE / ml ..

The culture was diluted to approximately 107 KBE / ml with 0.85% NaCl solution, pH 7.2.

Basal layer: The Petri dishes were filled with approximately 18 ml of sterile nutrient agar which solidified.

Top layer: 3.5 ml of the dilution of the germ in NaCl at 0.85% NaCl in 500 ml of fixed liquid agar was measured in a pipette which was cooled in a water bath at 47 ° C and homogenized. Eventually, 6 ml of germ-infested agar was distributed over the solidified basal layer. After a drying and storage time of approximately 24 hours at 4 ° C, the plates were ready for the test.

Dripped amount: 100 μl of a 1% solution of the tetraester solution of formula (104) in absolute ethanol was measured with a pipette in the center of the plate and dried for about 30 minutes at room temperature (the substances were run in about 20-30 mm).

Results of the agar diffusion test: After 48 h incubation of the agar plates at 37 ° C, the basal layer of the test substances was evaluated in the drip zone.

A selective inhibition of Corynebacterium xerosis ATCC 373 was found.

Claims (5)

1. An adduct of diester amine of formula where Ri R2 R3 / R4 are each independently of the other C4-C22 alkyl; C2-C22 alkenyl; or C5-C7 cycloalkyl; Xi and X2 are each independently of the other hydrogen, C? -C4 alkyl; C2-C hydroxyalkyl or C2-C4 hydroxyhaloalkyl; And it's a radical formula (lb) i is C2-C3 alkylene or 2-hydroxy-n-propylene; X3 is hydrogen; C 1 -C 4 alkyl, C 2 -C 4 hydroxyalkyl; or C2-C hydroxyhaloalkyl; C-W is an asymmetric carbon atom in the R or S configuration, where, if J = R, C2 = R; C ^ S, C2 = S; and C ^ R; C2 = S; my is 1 or 2; and n is an integer from 1 to 4; p is 0 or 1; adduct which may be in the form of a free base, acid, acid salt or quaternary ammonium salt.

2. The diester amine adduct according to claim 1, characterized in that in the formula (1) Ai is C2-C3 alkylene; m is 2; and P is 0.

3. The diester amine adduct according to any of claim 1 or claim 2, characterized in that Xi and X2 are hydrogen.

4. The diester amine adduct according to one of claims 1 to 3, characterized in that Ri, R2, R3 and 4 are C4-C22-5 alkyl. A process for the preparation of the compound of the formula, (1) , which comprises reacting the diaminotetracarboxylic acid of formula (lg) with thionyl chloride and an alcohol for the corresponding ester compound of formula (lf) according to the following scheme: + chloride The use of diester amine adduct of formula characterized in that Ri / R2 / R3 / 4 Xi and X2 Y and n have the meaning according to claim 1, as a complexing agent. The use according to claim 1, which comprises using the compound of formula (2) in food and beverages, in rust and decalcification baths, as additives in liquids for cooling water circuits, in personal care products , as stabilizers of bleaching, in cleaning agents and detergents and in the textile and paper industry. 8. The use according to claim 6, which comprises using the compound of formula (2) in personal care products. 9. The use according to claim 8, which comprises using the compound of formula (2) in deodorants. 10. A personal care product, characterized in that it comprises 0.01 to 15% by weight of the diester amine adduct of formula (1) or (2). 11. The use of the diester amine adduct of formula (1) as a hand softening agent for organic fiber materials.