EP1066305A2

EP1066305A2 - Sucrose-n-alkyl-asparaginates, production and use thereof

Info

Publication number: EP1066305A2
Application number: EP99915582A
Authority: EP
Inventors: Gerhard Kretzschmar; Hans-Ulrich Hoppe; Tilmann Brandstetter
Original assignee: Aventis Research and Technologies GmbH and Co KG
Current assignee: Aventis Research and Technologies GmbH and Co KG
Priority date: 1998-03-23
Filing date: 1999-03-12
Publication date: 2001-01-10
Also published as: JP2002507621A; DE19812661A1; AU3411399A; AU746197B2; CA2325396A1; WO1999048901A2; WO1999048901A3

Abstract

The invention relates to suchrose-N-alkyl-asparaginates of formula (I) and to the production and use thereof.

Description

description

Sucrose-N-alkyl asparaginates, their preparation and use

The invention relates to sucrose-N-alkylasparaginates of the formula (I) according to FIG. 1, their preparation and use.

Sucrose, as a hydrophilic component, is converted with fatty acid derivatives according to common processes to the known sucrose fatty acid esters (FIG. 2), which can be used as industrial auxiliaries and additives due to their amphiphilic properties. The known compounds according to FIG. 2 are described as non-toxic, non-irritating to the skin and readily biodegradable. Sucrose acetates with R ¹ = OAc are used, for example, in detergents as bleach activators and with longer-chain fatty acid residues as surface-active compounds. Due to the very favorable physiological properties, there are further areas of application in the food industry as emulsifiers, for example in baked goods and chocolate, and in cosmetic formulations. Despite these advantages and although the compounds according to FIG. 2, in which up to 8 fatty acid residues can be bonded directly to the OH groups of sucrose via ester bonds, have long been known, they are only used to a small extent as surface-active substances. They are preferably only used in the cosmetics, food and pharmaceutical sectors, where special dermatological and toxicological requirements are made. The reason for this is, in particular, their complex and expensive production, which prevent wider commercial use. On the other hand, for example, the sorbitan fatty acid esters, which are accessible from the structurally simpler glucose in a technically simpler way, have conquered a market as emulsifiers for many years. For the wider commercial use of products which are available from the particularly inexpensive and available in large quantities of sucrose, for example as cleaning agents or cosmetics for the consumer goods sector, an inexpensive manufacturing process thereof is above all necessary. The known esters of sucrose according to FIG. 2 are mainly produced on an industrial scale by means of transesterification processes: In the solvent process, sucrose is reacted with fatty acid methyl ester R ^ COMe in the presence of a basic catalyst in a solvent such as dimethylformamide or dimethyl sulfoxide (JP 04,247,095). In the microemulsion process, the fatty acid ester is dispersed in a solution of the carbohydrate using an emulsifier. The solvent is removed before the actual esterification takes place (EP 0254376). In the solvent-free process, the so-called direct process, the fatty acid methyl ester is reacted in the melt with sucrose and a basic catalyst (GB 1399053). Lipases are used in other processes (DE 3430944). Finally, the esterification of sucrose can also be carried out with carboxylic acid chlorides or anhydrides. In processes which are unsuitable for large-scale industrial productions, expensive auxiliary bases such as pyridine or N, N-dimethylaminopyridine are required (DE 19542303). In the latter publication, mixtures of oxidized sucrose, in particular sucrose monocarboxylic acids, are used, which in turn can be produced in a complex process in a low yield in a high yield, for example according to DE 4307388.

The known transesterification processes are very expensive both in terms of their process control and product isolation. The reaction parameters pressure and temperature have to be carefully checked and to obtain the sucrose esters it has to be extracted and distilled several times. In addition, the high reaction temperatures in combination with the long reaction times lead to discoloration of the products, which can only be reversed using complex cleaning processes. A further disadvantage of the compounds according to FIG. 2 is that they are used as monoesters. as diesters show surface-active properties, but because of their limited solubility in water they can only be used to a limited extent as surfactants. The monoesters dissolve poorly in cold water, while the diesters are only emulsifiable in water. The above-mentioned multi-stage process according to DE 19542303 therefore tries to circumvent this problem by oxidatively introducing the additional carboxylate group in the sucrose molecule. EP 0324595 describes “amino-functional compounds as builders / dispersants in cleaning agents” which are obtained by adding amino acids to maleate half-esters of polyols. The latter are obtained by reacting maleic anhydride, in particular with polyvinyl alcohol, also including sucrose. Although the reaction of maleic anhydride with alcohols has been known for a long time, the subsequent reaction with amino acids is problematic since this requires a balanced system of buffers and bases which suppresses the alkaline back-reaction of the maleate half-ester, preferably NaOH / Na2CO3. The excess bases have to be neutralized and the salts separated off as by-products. In addition, complex cleaning steps are required and the yields are not quantitative, since the maleate half-ester is naturally split off again by hydrolysis with aqueous alkali metal hydroxide solution.

The maleate half ester of sucrose according to Fig. 3 is e.g. as a builder (CO / builder) in detergents (DE 2148279).

DE 2739343 describes “basic” surface-active esters of aliphatic polyols, it also being possible to use sucrose as the polyhydroxy compound. Compounds of the general formula Rβ-

N (Rg) -CH (R- | o) -CH (R- | i) -COOH, where R _{8 is} a C ₈ -C ₂₂ -alkyl or alkenyl radical, R ₉ and Rn, inter alia, also hydrogen and Rio can also mean a carboxyl group. However, such “acidic esters” cannot be produced by the multi-stage process described in DE 2739343, because only “basic esters” of sucrose are accessible thereafter, ie completely esterified carboxylates in which the carboxyl group (radical R- | rj) in esterified, but not in protonated or anionic form.

The object of the present invention was therefore to provide new derivatives of sucrose which are easy to prepare and can be used as surface-active compounds. Surprisingly, "acid esters" of sucrose have the required properties.

The present invention therefore relates to sucrose-N-alkylasparaginates of the formula (I)

(l)

in which R1, independently of one another, identically or differently, a group selected from hydrogen, a compound of the formula (II)

(ll)

where R is CnH ₂ n + ι or C _n H2n, where n is an integer from 2-28, preferably from 6-22, especially from 12-18, a compound of the formula (III)

(III) and / or a radical of formula (IV)

ff. .

0 = S— O M (IV)

and M ⁺ is hydrogen, an alkali metal ion and / or an alkaline earth metal ion, preferably a sodium, potassium, lithium, magnesium, calcium and / or ammonium ion, with the requirement that at least one radical R ^{1 is} a compound of the formula (II) is.

The compounds of the formula (I) according to the invention cannot be prepared by the process described in DE 2739343, because a chemoselective cleavage of the ester group denoted by RI _Q would have to be carried out in an additional synthesis step. However, this is not possible with known methods, since the other carboxyl group in Rg-

N (Rg) -CH (R- | o) -CH (R ^« | i) -COOH would just split back the ester bond. This saponification occurs even at mild pH values below pH = 10. In addition, the “basic esters” in DE 2739343 are described as clearly water-soluble, resinous and little or practically non-foaming. In contrast, the “acid esters” of the formula (I) according to the invention are partially crystalline but amorphous solids with only limited water solubility, with very stable, good foam-forming emulsions are formed. This is particularly surprising because aliphatic esters of carboxylic acids are generally less water-soluble than their salts.

In addition, one can from the stoichiometry of the in the examples of DE

The reactions described in 2739343 conclude that the “basic esters” described are mixtures of sucrose with the reaction components of the formula R8-N (Rg) -CH (R <| o) -CH (R <| i) -Cθ2CH3. For example, 137 parts of sucrose were reacted with 66 parts of a compound of the formula C <i2H25NH-CH (COOCH3) (CH2COOCH3) in Example 6 of DE 2739343. However, this implementation could only have resulted in 128 parts of the product. In fact, 189 parts of product were obtained. The difference can only be unreacted sucrose, which is clearly water-soluble and does not form a foam in water. In fact, only a basic nitrogen content of 1.4% was found, which would be expected even if the substances were only mixed (calculated 1.4%). However, the predicted reaction product would theoretically have a nitrogen content of 2.2%. Also, the value of 123 specified as the saponification does not allow a conclusion on the formation of a reaction product, because no change in the saponification value can be expected from the stoichiometry forth, and because of the used 66 parts of the compound C ^'] 2H25NH-CH (COOCH3) (CH2COOCH3) with the theoretical saponification number

122 in any case practically the same saponification number must be found again. It can be concluded from this that the reactions in DE 2739343 cannot lead to the “acidic esters” according to the invention, do not describe a preparation and therefore do not represent prior art in this regard.

The present invention therefore provides novel sucrose-N-alkylasparaginates of the formula (I) which can be prepared surprisingly smoothly in high yields by a two-stage one-pot process and which are widely biodegradable, physiologically compatible and surface-active substances can be used. The compounds according to the invention are notable for the fact that at least one and up to eight Ri radicals represent a 3-alkylamino-substituted half-ester radical of 1,4-butanedicarboxylic acid or its salts according to formula (II).

To regulate the solubility properties, the compounds according to the invention can, in a preferred embodiment, also contain one or more maleat residues of the formula (III), in particular according to the definition of the degree of substitution DS given in FIG. 1, which also includes non-integer intermediate values, where the sum of the residues A and B does not exceed the value DS = 8.

In metal-free form (M ^® = H ^Θ ), the compounds according to the invention - as is typical for amino acids - can also be used as internal salts (betaines) with protonation of the Amino function are present. M ^® is preferably an ion of the alkali and alkaline earth metals such as Na ^® , K ^® , Li ^® , Mg ²⁺ , Ca ²⁺ and NH ₄ ^® , particularly preferably sodium or potassium ions or mixtures thereof.

Suitable alkylamino radicals NHR ² come from primary amines (monoalkylamines

R ² NH2) of chain lengths C2 to C28 _> preferably of commercially available fatty amines with chain lengths of CQ to C22, in particular of C12 to Cis, which are also hydrogenated from more or less wide production cuts, for example from coconut, from palm, Soybean or tallow oil fats are obtained, especially from decyl, dodecyl, tetradecyl, hexadecyl or octadecylamines or from residues derived from coconut, palm, soybean or tallow oil fats. Accordingly, the compounds according to the invention can also carry different radicals.

Coconut fat generally contains a mixture of hexane, octane, decane, lauric, myristic, palmitic, stearic, behen, oil and linoleic acid residues. Palm oil generally contains a mixture of myristic, palmitic, stearic, oil and linoleic acid residues. Soybean oil contains, inter alia, residues with a carbon chain length of 14, 16, 18, 20 and 22 carbon atoms, usually C ₁₄ unsaturated, C ₁₆ monounsaturated and saturated, Cιβ monosaturated, triple and triple unsaturated and saturated, C20 monounsaturated and saturated and C _{22 is} saturated. Taigfett generally contains residues with 14, 16 and 18 carbon atoms.

In a further preferred embodiment, one or more, preferably up to 2, radicals R ^{1 can} also be present in sulfated form, the sum of the radicals A, B and C naturally not being able to exceed the number 8.

Another object of the present invention is a process for the preparation of a sucrose-N-alkylasparaginate of formula (I), wherein in a first step sucrose is acylated with maleic acid or a derivative of maleic acid, and in a second step one to eight molar equivalents of amine of the formula R ² NH ₂ with R ² equal to C _n H ₂ n + ι, where n is an integer from 2-28, preferably 6-22, especially 12-18 the maleate sucrose formed in the first step is added.

The process according to the invention consists in the acylation of the sucrose with preferably maleic anhydride (MSA) and the subsequent addition of fatty amines to the CC double bond of the intermediate maleat sucrose, preferably without isolation or purification of the intermediate. Another suitable acylating agent is maleic acid chloride. The fatty acid residue is not introduced directly by acylation of the OH groups of the sucrose, but indirectly via the addition of the fatty amines to the preferably non-isolated intermediate. This creates an N-alkylated aspartic acid, which acts as a linker group for the lipophilic alkyl radical. Both substeps are largely stoichiometric in terms of additions without the formation of stoichiometric amounts of salt as by-products.

In a preferred embodiment, the acylation is carried out in the presence of a catalyst, preferably in the presence of a basic metal salt, in particular a carbonate, bicarbonate, acetate and / or formate. Usually one equivalent of a basic metal salt is used, which acts as a catalyst in the acylation with MSA and for the neutralization of the carboxylate formed. By-products are, depending on the metal salt, the easily separable acetic acid or carbon dioxide. At the same time, the formation of the carboxylate salt advantageously prevents the consumption of a salt-bound fatty amine equivalent, which would then no longer be available for the subsequent addition to the CC double bond. The carboxylate group formed in the first step additionally improves the hydrophilic properties and the water solubility of the surface-active substances. Surprisingly, the process manages completely without addition of aqueous bases and buffer systems, for example as described in the application EP 0324595, which is therefore particularly advantageous.

In a further embodiment of the process according to the invention, the sucrose-N-alkylaspartate is sulfonated in a further step, preferably up to two radicals R ¹ using one of the methods familiar to the person skilled in the art Functionalization of hydroxyl and amino groups can be sulfonated. For this purpose, following the reactions described above, the reaction products are reacted in the same reaction vessel or after separating off the intermediates with the calculated amount of a sulfonating reagent, if appropriate after adding an inert solvent such as dichloromethane, tetrahydrofuran or dioxane. Suitable sulfonating reagents are e.g. B. Sθ3 ₎ CISO3H, DMF-SO3 and / or pyridine-Sθ3.

The advantages of the process according to the invention compared to the known production processes are the high reactivity of the maleic anhydride and the nucleophilic attack of the fatty amine on the electrophilic CC double bond, as a result of which further purification steps, expensive auxiliary bases or auxiliary reagents, such as catalysts, can be dispensed with for this reaction step . By selecting the radicals R ¹ and the degree of substitution DS, the process also makes it possible to provide a large number of differently substituted compounds of the formula (I) with tailored application properties and areas of use. In addition, the yields in the two-stage one-pot process are over 90%.

The process according to the invention for the preparation of compounds of the formula (I) with a defined DS can be carried out, for example, as follows:

Sucrose and the correspondingly calculated amount of, for example, maleic anhydride and, for example, an equivalent amount of a basic metal salt (MX), such as, for example, sodium hydrogen carbonate, sodium carbonate, sodium acetate, sodium formate, lithium acetate or potassium acetate, preferably sodium hydrogen carbonate, sodium carbonate or sodium acetate, are in bulk or in a suitable solvent, for example in N, N-dimethylformamide (DMF), N, N-dimethylacetamide (DMA), dioxane, N-methylpyrrolidone (NMP), DMSO, tetrahydrofuran (THF) or in mixtures of these solvents, preferably in N , N-dimethylformamide, N-methylpyrrolidone, DMSO, dioxane or in mixtures of these solvents, at temperatures from 20 ° C to the boiling point of the solvent or solvent mixture in question, preferably at temperatures in the range from approximately 20 to approximately 140 ° C., in particular at temperatures from approximately 40 to approximately 120 ° C.

The reaction is complete after the sucrose has been completely consumed, which is easily detectable by thin layer chromatography. Then the amount of the relevant alkylamine R ² NH2 or the alkylamine mixture calculated in accordance with the desired DS is added and in the same reaction vessel at temperatures from about 0 ° C. to the boiling point of the solvent or the solvent mixture in question, preferably at temperatures of about 20 to about 60 ° C. until the reaction is complete after analysis by thin layer chromatography.

The end product partially precipitated as a colorless solid during the reaction, which can be filtered off, washed and dried. The main amount of the solvents used is preferably distilled off and the product is isolated by stirring in a low-boiling solvent. Alternatively, the product can also be precipitated from the reaction solution by adding the appropriate amount of solvent. Suitable solvents for the stirring and precipitation processes are ethyl acetate, hexane, methyl isobutyl ketone, acetone and the like. After thorough vacuum drying, the solid end product is obtained as a colorless, odorless powder.

Depending on the nature of the metal salt MX used, the process provides the corresponding carboxylate salt as the end product; the sodium or potassium salts or mixtures thereof are preferred. These can also be converted with equivalent amounts of protonic acids into the free carboxylic acids (M ^® = H ^® ), which are in equilibrium with the betaine form due to the secondary amine function present. By carefully adding a maximum of another acid equivalent, the secondary amino group in the aspartic acid part can be protonated, for example halogen carboxylic acids, aliphatic and aromatic carboxylic acids and sulfonic acids can be used. The negative counter ion used has an effect, for example, on the surfactant properties of the compound according to the invention. By the appropriate selection of the counter ion, for example a paraffin sulfonates, tailor-made thickeners can be produced in formulations for shampoos and other cosmetic cleaning agents as well as for liquid surfactant systems.

In a further embodiment, following the reaction described above, the products obtained are in the same reaction vessel or after separation of the intermediates with the appropriate amount of the sulfonating reagent, preferably up to 2 molar equivalents of the sulfonating reagent, if appropriate after adding an inert solvent such as, for example Dichloromethane, tetrahydrofuran or dioxane. Preferred sulfonating reagents are e.g. B. SO3 CISO3H, DMF-SO3 or pyridine-Sθ3.

The compounds of the formula (I) obtained by the process according to the invention are characterized by means of analytical and spectroscopic methods such as TLC, H NMR and mass spectroscopy and elemental analysis. The DS of the products can be determined by means of the proton ratio (integration of the ^' Η NMR signals) and by means of elemental analysis.

The compounds according to the invention have excellent surface-active properties and can therefore be used in many different ways as industrial auxiliaries and additives, for example as surfactants, emulsifiers, stabilizers, plasticizers or solubilizers. These compounds with DS = 4-8 are also suitable as low-calorie fat substitutes in foods.

At degrees of substitution (DS) from 1 to 7, substance mixtures are obtained by reaction with, for example, MSA, the 3 primary OH groups reacting predominantly. Under special conditions, the 2-OH group of glucose can also be selectively acylated (FR 2670493), the yields being generally low, for example about 42% in the selective enzymatic acylation of the 1 ^' OH group with methacrylic acid vinyl ester and Subtilisin in DMF (Chan, AWY & Ganem, B., Biocatalysis, 1993, 8, 163-169). Generally there is a decreasing reactivity in the rice order HO-6 approx. = HO-6 ^' > HO-1 ^' > HO-2 approx. = HO-3 ^' . Connections with DS = 2 and DS = 3 therefore predominantly have the constitution shown in FIG. 4.

The addition of the alkylamine R ² NH2 to the sucrose maleates or to mixtures of intermediates, which can contain up to 8 residues R ¹ , generally takes place stoichiometrically until the maleate-CC double bond is completely reacted with a certain amine RI NH2. The amine R ^ NH2 can also be used substoichiometrically while maintaining unsaturated maleate substructures, for example in order to achieve a certain water solubility of the products. A mixture of several different alkylamines can also be used. Accordingly, the compounds according to the invention can also carry different radicals. The ratio of hydrophilicity to hydrophobicity, which determines the surface-active properties of the compounds according to the invention, is adjusted via the structure of the alkyl substituents R ² and their degree of substitution (DS). The DS can be adjusted via the molar ratio of alkylamine R ² NH2 to sucrose.

The water solubility of the compounds according to the invention can optionally also be adjusted via additional sulfonate groups, in that a higher number of N-alkyl aspartate residues can be compensated for by preferably up to two sulfonate groups.

The compounds according to the invention have a total of up to eight radicals R ¹ , the DS being between 1 and 8. As the DS increases, the lipophilicity of the compounds increases and their water solubility decreases accordingly. At the same time, this effect can be compensated for by the carboxylate or sulfonate groups introduced. As already explained, the amphoteric character and the water solubility of the surface-active substances can be modulated in a simple manner, which is important for the intended areas of use. For cosmetic applications, for example in shampoos or bath additives, but also in household cleaning agents, such as in dishwashing detergents, good foaming power and good foam stability are important. The ampho- tere character of the compounds can be expected a special skin tolerance and skin protection effect, since a favorable interaction with the collagen of the skin can occur. The formation of a protective layer, the excessive attack of surfactants on upper skin layers and their strong degreasing and irritation can be reduced by other anionic surfactants contained in a formulation. In addition, the hydrophilic carboxylate groups of the asparagine substructure or, if appropriate, additional sulfonate groups ensure good washability from the skin, which is particularly important for body cleansing.

For surface-active substances, surfactants and emulsifiers, the DS is therefore preferably approximately 1-3, in particular <3, and for low-calorie fat substitutes for foods, preferably approximately> 3, in particular approximately 4-8. In the case of low-calorie fat substitutes, melting points and taste sensations can be controlled via the composition of the R ² residues and the DS value: Only those fatty substances with a melting point above body temperature and which are not liquid at room temperature give a pleasant taste sensation. A coordinated taste sensation, for example for a substitute for cocoa butter, can be achieved by a corresponding mixture of fatty amines of different chain lengths, by C-12 (lauryl-), C-16 (palmityl-), C-10 (caprinyl-), C-14 (Myristyl) and C-18 (stearyl) amines can be used in coordinated proportions.

Another object of the present invention is therefore the use of a sucrose-N-alkyl aspartate according to the invention as surface-active compounds, in particular the use of one or more sucrose-N-alkyl asparaginates according to the invention as an additive in hygiene, cleaning, cosmetic, food and / or medicinal products in pesticides or for the prevention and / or control of water pollution by chemicals and / or oil, for example as an additive in soaps, abrasives, all-purpose cleaners, dishwashing detergents, detergents, shampoos, heavy duty detergents and / or bath additives, the degree of substitution DS of at least one sucrose N-alkyl aspartate is preferably between 1 to about 4. In a particular embodiment, the sucrose-N-alkylasparaginate is used together with at least one other surface-active substance (co-surfactant), the co-surfactant preferably being selected from alkyl polyglycosides, 6-0-monoesteralkyl glycosides, alcohol ether sulfates or alkyl glucamides.

Another object of the present invention is the use of a sucrose-N-alkyl aspartate according to the invention as a low-calorie fat substitute, the degree of substitution DS of at least one sucrose N-alkyl aspartate preferably being between about 4 and 8.

In another object of the present invention, the sucrose-N-alkyl aspartate according to the invention is in the form of an aqueous solution, an emulsion, a suspension, a jelly, a cream, a paste or a powder.

The surface-active properties of the compounds according to the invention thus open up a multitude of possible uses. The following application examples serve to illustrate the various possible areas of application and do not limit these examples.

When washing and cleaning, the lowering of the surface tension results in easier dirt detachment from the fibers and a stabilization of the dirt components in the wash liquor. In the textile industry, washing, dyeing and finishing processes are improved and accelerated with the help of surfactants. In wool dyeing, for example, the wool damage caused by the dyeing process is reduced, in hydrogen peroxide bleach baths the surfactants have a stabilizing effect and the dispersing effect for textile dyes facilitates the dyeing process. In the leather industry, in fur preparation and in the paper industry, surfactants are important aids. They are added to car and machine oils to form uniform, non-tearing lubricating films. They improve wetting in paints and coatings and, due to their dispersing effect, also delay the settling of the color pigments when the paint is standing. In cosmetics, in the food industry, in medicine, in disinfectants and in pest control, the distribution of the active ingredients in a liquid phase or its Adhesion achieved on a surface. They can also be used as emulsifiers for baked goods and ice cream. Floor care products, furniture and car polishes as well as paint strippers typically also contain surfactants. When ores, coal and potash are extracted, the solid substances float by the surfactant coupling them to air bubbles (flotation). On the other hand, other surfactants can be influenced by the action of these surface-active substances in their foaming ability by promoting the rising and bursting of the gas bubbles (defoaming). Such foam control agents are used in particular in dishwashing detergents and in many technical processes such as paper and sugar production. The low toxicity and biocompatibility known from other sugar residues and from biosurfactants means that the compounds according to the invention also have similarly favorable properties. These advantages can also be used, for example, to combat tanker gaps at sea and, in general, to combat oil pollution in the water by distributing the oil more quickly without the disadvantages of an additional water pollution caused by the auxiliary.

In the pharmaceutical sector, biocompatible surfactants are used, for example, as auxiliaries in vaccine production, specifically for the isolation and purification of bacterial polysaccharides as vaccines (see, for example, WO97 / 30171).

In detergents, tensides make up approx. 10-40% of the total amount depending on the intended use. The typical composition of a universal detergent can be, for example, 5-15% of a compound according to the invention, 3-5% of another foam regulator (soap or silicone oil), 30-40% of a builder (e.g. zeolite, polycarboxylate), 20-30% of a bleaching agent ( e.g. sodium perborate), 0-10% of an adjusting agent (e.g. sodium sulfate), 1.5-4% of a bleach activator (e.g. tetraacetylethylene diamine), 0.2-2% of a stabilizer for perborate (e.g. EDTA, Mg silicate), 0.3-1 % of an enzyme (e.g. a protease), 0.5-1% of a graying inhibitor (e.g. carboxymethyl cellulose), 0.1-0.3% of an optical brightener (e.g. a stilbene or pyrazoline derivative) and 0.1-0, Contain 2% of a fragrance. The invention relates in particular to aqueous solutions, soaps, cleaning agents such as abrasives, all-purpose cleaners, dishwashing detergents or detergents, shampoos, heavy-duty detergents, bath additives, foods, cosmetics, emulsions, suspensions, jellies, facial cleaners, cold wave and fixatives, surfactant preparations for babies, creams, pastes and Powder, at least one of the compounds according to the invention or mixtures thereof with other surface-active substances (co-surfactants), for example alkyl polyglycosides (APGs), 6-O-monoesteralkyl glycosides (Biosurf® types from Novo Nordisk), alcohol ether sulfates (AEs), or alkyl glucamides included.

The betaine structure of the N-alkyl aspartate specified in the compounds according to the invention is structurally very close to the aspartic acid naturally occurring in proteins. It can therefore be assumed that the tendency towards the formation of carcinogenic N-nitrosamines, as discussed, for example, with purely nonionic amphiphiles, such as the N-alkylglucamines, does not exist.

In the pharmaceutical industry, surface-active compounds are used in formulations for active substances with which an improved absorption of active substances is to be achieved (drug delivery systems). Cyclosporin, for example, is formulated as a "microemulsion preconcentrate". Even with vitamins, such as vitamins A and K, there are solubilizing formulations in micellar form. However, there are very few suitable surface-active substances which, on the one hand, have a good ability to include sufficiently stable Active ingredients and on the other hand have zwitterionic properties at low critical micelle concentration and low toxicity. Particularly desirable is the ability to form stable vesicles. This requires surface-active substances with short hydrophilic head groups and with long hydrophobic chains, such as those present in the phosphatidylcholines As with these substances, the compounds according to the invention also have structural prerequisites for the formation of stable vesicles, for example with 2 long alkane chains (DS approx. 2) Combined with DS = 2 and R ² = dodecyl in one liter of water, a homogeneous, opaque, milky phase is obtained which remains stable and unchanged for 8 weeks at pH 5-7. The light scattering observed is presumably caused by microvesicles, for which a minimal structural detail is shown in FIG. 5, for example.

Alternatively, larger structures can also be formulated according to the scheme K1-S1'-S2-K2-S2'-S3-K3-S3 'etc., K1 "head group molecule 1", S1 "tail group molecule 1", S1' "others Tail group of molecule 1 "etc. means. Pharmaceutical or cosmetic active ingredients can be incorporated into such vesicles, which can lead to an improved form of administration of the active ingredients. Therapeutic genes, antisense oligonucleotides or retroviral expression vectors can also be used as active ingredients for their application So-called transfection reagents are required, usually lipids such as DOTAP or DC cholesterol (SIGMA, Saint Louis, MO) or mixtures of neutral and cationic lipids are used for this purpose.The cationic structural element promotes the complexation of the DNA and the lipid part the integration into The cell membrane These structural requirements also apply to the compounds according to the invention, which as amino acids acids can be in the physiologically protonated form. In particular, the compounds according to the invention can therefore be used for in vitro or in vivo transfection of cells, in particular skin cells, in order, for example, to cure genetically caused skin diseases. The transfection of skin cells with retroviral expression vectors is e.g. in Deng., H. et al., Nature Biotechnology, 1997, Vol. 15, 1388-1391.

Another object of the present invention is therefore the use of the sucrose-N-alkylasparaginates according to the invention as a transfection reagent. The compounds according to the invention can be used in various application forms (formulations), for example in the food, pharmaceutical or hygiene sector. The form of application is adapted to the respective area of application.

The following figures and examples are intended to explain the invention in more detail without restricting it: Description of the figures

Fig. 1 shows schematically the production of the sucrose-N-alkyl asparaginates according to the invention and the calculation of the degree of substitution DS. Fig. 2 shows known sucrose fatty acid esters. Fig. 3 shows a male half-ester of sucrose.

4 shows examples of compounds with DS = 2 and DS = 3. Further maleate groups, of which up to 6 can be present at DS = 2 and up to 7 at DS = 3, as well as sulfonate groups, of which preferably up to 2 Groups may not be present in the formulas. The exact position of the substituents can vary and deviate from the illustration shown here. 5 shows a minimal structural section of a microvesicle. 6 graphically shows the results of comparative tests on foam stability. 7 graphically shows the results of comparative experiments on the dispersing effect.

EXAMPLES

Example 1: Synthesis with sodium acetate in DMF: DS = 2.0, R ² = dodecyl,

30.0 g (87.6 mmol) sucrose, 15.8 g (192.6 mmol, 2.2 equiv.) Sodium acetate and 18.9 g (192.8 mmol, 2.2 equiv.) Maleic anhydride were 3 hours at 50 ° C in 150 ml of dry N, N-dimethylformamide. After the thin layer chromatogram, the sucrose was then converted quantitatively. 35.7 g (193 mmol, 2.2 equiv.) Of 1-dodecylamine (laurylamine) were added and the mixture was stirred at 50 ° C. for a further 3 hours. During the reaction, some of the product precipitated out as a colorless solid. The solvent was largely distilled off in vacuo and replaced with ethyl acetate with stirring. The product was filtered off, washed with ethyl acetate and dried in vacuo at 70 ° C. Yield: 83.9 g. Based on a composition with DS = 2 of the empirical formula C44H7sNa2N2θi7

(953 g / mol) the yield was 100%. The H NMR assignment (in CDCI3 / CD3OD) gave DS approx. 2.0: δ = 1.85 (t, Me), 1.25 (m, CgH ₈ ), 2.6-3.3 (m, CH ₂ NCHCH ₂ ),

2.30-5.40 (sucrose-CHO). [Assignment compared to the N-dodecyl aspartate C "] 2H25NHCH (COONa) CH2COOCH ₃ ; through the formation of micelles or vesicles

Line broadening and deviating shifts, e.g. CH2COOSucrose can also be assigned to the broad multiplet at δ = 1.95. At the

N-dodecylasparaginate C <i2H25NHCH (COONa) CH2COOCH3 the corresponding CH2 signal is δ = 2.4 (CDCI3).] Elemental analysis: N (found) 2.7%, (N calculated for DS = 2.0: 2, 9%), Na (found) 4.2% (Na calculated for DS = 2.0: 4.8%). Mass spectrum (electrospray, ESI-MS): [M <| -H ⁺ ] ~ = 624 (M <| = C28H51 NO14;

625); [M ₂ ] ^" = 908 (M ₂ = C44H80N2O17; 908); [(M ₁ -2H ⁺ + Na +) ₂ ] - = 1272; In positive mode: [M + H ⁺ ] ⁺ = 626 (M <| = C2δH5i NO ₁ ; 625); [M ^ Na *] ^" = 648; [M ₂ + H ⁺ ] ⁺ = 907; [(M ₁ + H +) ₂ ] ⁺ = 1252.

Example 2: Synthesis with sodium carbonate in DMF: DS = 2.1, R ² = dodecyl

30.0 g (87.6 mmol) of sucrose, 10.2 g (96.2 mmol, 2.2 equiv. Na ^θ ) sodium carbonate and 18.9 g (192.8 mmol, 2.2 equiv.) Maleic anhydride 2 hours at 80 ° C and then 3 hours at 100 ° C in 150 ml of dry N, N-dimethylformamide with stirring. According to the thin layer chromatogram, the sucrose then reacted completely. 37.6 g (203 mmol, 2.32 equiv.) Of 1 -dodecylamine were added and the mixture was stirred for a further 3 hours at 50 ° C. and for a further 2 hours at 70 ° C. During the reaction, some of the product precipitated out as a colorless solid. The solvent was largely distilled off in vacuo and replaced with ethyl acetate with stirring. The product was filtered off as a colorless solid, washed with ethyl acetate and dried in vacuo at 70 ° C. Yield: 82.9 g (96% based on product with DS = 2.1

( ^c 45.6H80.8 ^Na 2.1 ^N 2, l Oi 7.3 = 983.6 g / mol). 1 H NMR (CDCI3 / CD3OD) gave DS =

1, 9-2.2 (assignment see example 1). Elemental analysis: N (found) 2.7%, N (calculated for DS = 2.1: 3.0%), Na (found) 4.8%, Na (calculated for DS = 2.0: 4.9%). Mass spectrum (electrospray, ESI-MS): [M «| -H ⁺ ] - = 624 (M- | = C ₂ 8H ₅ 1 N0 ₁₄ ; 625); [M ₂ -H ⁺ ] ^" = 907 (M ₂ = C44H8θN2θ ₁₇ ; 908); ^ Mi-H + j ^" = 1249; [2M-ι + Na ⁺ -2H ⁺ ] "= 1271. In positive mode: [M + H ⁺ ] ⁺ = 626 (M- | = C28H51 NO14;

625); [M ₁ + Na ⁺ ] ⁺ = 648; [M ₂ + H ⁺ ] + = 907; [(M ₁ + H ⁺ ) ₂ ] ⁺ = 1252.

Example 3: Synthesis with sodium carbonate in DMSO: DS = 1, 9, R ² = dodecyl

30.0 g (87.6 mmol) sucrose, 5.1 g (48.1 mmol, 1.1 equiv. Na ⁺ ) sodium carbonate and

9.5 g (96.9 mmol, 1.1 equiv.) Of maleic anhydride were reacted for 2 hours at 30 ° in 100 ml of dry DMSO with stirring. After adding another 5.1 g

(48.1 mmol, 1.1 equiv. Na ⁺ ) sodium carbonate and 9.5 g (96.9 mmol, 1.1 equiv.) Maleic anhydride were stirred for a further 8 hours at 30 ° and for a further 2 hours at 60 ° C. According to the thin layer chromatogram, the sucrose was then fully implemented. 35.7 g (193 mmol, 2.2 equiv.) Of 1 -dodecylamine were added and the mixture was stirred at 30 ° C. for 3 hours and at 40 ° C. for 2 hours. During the reaction, some of the product precipitated out as a colorless solid. The solvent was largely distilled off in vacuo and replaced with ethyl acetate with stirring. The product was filtered off as a colorless solid, washed with ethyl acetate and dried in vacuo at 70 ° C. Yield: 75.4 g (93% for DS = 1.9).

Example 4: Synthesis with sodium acetate in DMSO: DS = 2.2, R ² = dodecyl

30.0 g (87.6 mmol) sucrose, 15.8 g (192.6 mmol, 2.2 equiv.) Sodium acetate and 18.9 g (192.8 mmol, 2.2 equiv.) Maleic anhydride were 2 hours at 50 ° C in 100 ml of dry dimethyl sulfoxide with stirring. According to the thin layer chromatogram, the sucrose then reacted completely. 35.7 g (193 mmol, 2.2 equiv.) Of 1 -dodecylamine (laurylamine) were added and the mixture was stirred for a further 3 hours at 50 ° C. and for a further 2 hours at 70 ° C. During the reaction, some of the product precipitated out as a colorless solid. The solvent was largely distilled off in vacuo and replaced with ethyl acetate while stirring. The product was filtered off as a colorless solid, washed with ethyl acetate and in Vacuum dried at 70 ° C. Yield: 81.5 g (92% for DS = 2.2). The DS was determined by integrating the 1 H NMR spectrum from the ratio of the sucrose CHO signals and the N-dodecyl aspartate signals.

Example 5: Synthesis with sodium acetate in DMSO: DS = 1, 0, R ² = dodecyl

30.0 g (87.6 mmol) sucrose, 15.8 g (192.6 mmol, 2.2 equiv.) Sodium acetate and 18.9 g (192.8 mmol, 2.2 equiv.) Maleic anhydride were 2 hours at 50 ° C in 100 ml of dry dimethyl sulfoxide with stirring. According to the thin-layer chromatogram, the sucrose then reacted completely. 17.9 g (96.4 mmol, 1.1 equiv.) Of 1 -dodecylamine were added and the mixture was stirred at 20 ° C. for a further 6 hours. The solvent was largely distilled off in vacuo and replaced with ethyl acetate with stirring. The product was filtered off as a colorless solid, washed with ethyl acetate and dried in vacuo at 70 ° C. Yield: 66.3 g (98.6%). The DS was determined by integration of the H NMR spectrum, the ratio of CHO, maleate and N-dodecyl-signals at about 1, 0 ^(C 28 ^H 50 ^NaNO 14 = ^{^647-7} g / ol).

Example 6: Synthesis with sodium carbonate in DMSO and coconut fatty amine C ^< | 2 ^{: R2 =} dodecyl

30.0 g (87.6 mmol) of sucrose, 10.2 g (96.4 mmol) of sodium carbonate and 18.9 g (192.8 mmol, 2.2 equiv.) Of maleic anhydride were mixed in 100 at 50 ° C. for 3 hours ml of dry dimethyl sulfoxide reacted with stirring. According to the thin layer chromatogram, the sucrose then reacted completely. 40.0 g of genamine ^ 12R100D [from coconut fat, average molecular formula CH ₃ (CH ₂ ) i2.3 NH ₂ ] were added and the mixture was stirred at 40 ° C. for a further 3 hours. During the reaction, some of the product precipitated out as a colorless solid. The solvent was largely distilled off in vacuo and replaced with ethyl acetate with stirring. The product was filtered off as a colorless solid, washed with ethyl acetate and dried in vacuo at 70.degree. Yield: 78.0 g (89% for DS = 2.2). Example 7: Synthesis with sodium acetate in DMF: DS = 8, R ² = dodecyl

10.0 g (29.2 mmol) sucrose, 21, 6 g (263 mmol, 9 equiv.) Sodium acetate and 25.8 g (263 mmol) maleic anhydride were dissolved in 150 ml dry N, N- at 40 ° C for 3 hours. Dimethylformamide stirred. The ¹ H NMR analysis of a sample in D2O shows only small amounts of maleic anhydride (δ = 6.30 ppm) and the formation of the olefinic maleate protons at δ = 6.70 ppm and δ = 5.90 ppm in the expected integration ratio. 48.7 g (263 mmol, 9 equiv.) Of 1 -dodecylamine were added and the mixture was stirred at 20 ° C. for 14 h. The solvent was largely distilled off in vacuo and replaced with ethyl acetate while stirring. The product was filtered off, washed with ethyl acetate and dried in vacuo at 70 ° C. Yield: 73.0 g. (96%).

Example 8: Synthesis with sodium acetate in DMF: DS = 8, R ² = dodecyl / hexadecyl / octadecyl (35/60/5%)

10.0 g (29.2 mmol) sucrose, 21, 6 g (263 mmol, 9 equiv.) Sodium acetate and 25.8 g (263 mmol) maleic anhydride were dissolved in 150 ml dry N, N- at 40 ° C for 3 hours. Dimethylformamide stirred. A mixture of 17.1 g (92.0 mmol) of 1-dodecylamine, 38.1 g (157.8 mmol) of 1-hexadecylamine and 3.5 g (13.1 mmol) of 1-octadecylamine was added and the mixture was stirred Mix for 14 h at 20 ° C. The solvent was largely distilled off in vacuo and replaced with ethyl acetate with stirring. The product was filtered off, washed with ethyl acetate and dried in vacuo at 70 ° C. Yield: 90.0 g. (99%).

Example 9: Synthesis of (1) without using solvent

30.0 g (87.6 mmol) of sucrose, 15.8 g (192.6 mmol, 2.2 equiv.) Sodium acetate were stirred for 20 minutes at a bath temperature of 195 ° C. under vacuum (approx. 20 torr). The mixture was cooled to 175 ° C. (bath temperature) at normal pressure and 18.9 g (192.8 mmol, 2.2 equiv.) Of molten maleic anhydride were slowly added dropwise (5 minutes). The mixture turned brownish, started to foam and was grooves cooled to 125 ° C while stirring. The ¹ H NMR analysis of a sample in D ₂ 0 showed only small amounts of maleic anhydride (δ = 6.30 ppm) and the formation of the olefinic maleate protons at δ = 6.70 ppm and δ = 5.90 ppm in the expected integration ratio . 35.7 g (193 mmol, 2.2 equiv.) Of 1-dodecylamine (laurylamine) were added, the mixture was stirred at 125 ° C. for 20 minutes and then ethyl acetate was added with cooling under stirring and stirring. The product was filtered off, washed with ethyl acetate and dried in vacuo at 70 ° C.

Example 10: Monosulfonation with chlorosulfonic acid

5.0 g (6.0 mmol) of product from Example 1 (RS 786) were suspended in 50 ml of dichloromethane and 1 ml of dimethyl sulfoxide. 0.4 ml (6.0 mmol) of chlorosolonic acid in 25 ml of dichloromethane were added dropwise at room temperature over the course of 1 hour. The mixture was stirred for a further 3 hours at room temperature. Then a clear solution was obtained. The solvent was removed under vacuum. The mixture was then stirred with ethyl acetate, suction filtered and dried under vacuum at 60 °. 4.6 g of colorless solid (RS 814) were obtained.

Example 11: Monosulfonation with pyridine-Sθ3 complex

5.0 g (6.0 mmol) of product from Example 1 (RS 786) were stirred in 50 ml of dimethylformamide at 70 ° C. until the solid had almost completely dissolved. Then allowed to cool to 30 ° C and 1.0 g of sulfur trioxide-pyridine complex was added. The mixture was stirred at 30 ° C. for 3 hours and at 60 ° C. for 1 hour. The solvent was removed under vacuum. The mixture was then stirred with ethyl acetate, suction filtered and dried under vacuum at 60 ° C. 4.3 g of colorless solid (RS 825) were obtained.

Example 12: Determination of the surface tension

The compounds according to the invention, in particular those with a degree of acylation up to DS = 3, had excellent surface-active properties. Table 1 shows that the compounds according to the invention reduce the surface tension of water. The critical micelle concentration (CMC) and the Emiedrigung the surface tension (σ _m) of (double distilled Lauda, type TD1, water, σ _mi n = 71, 8 mN / m) with a tensiometer measured at 25 ° C. The concentration was increased to the minimum force to obtain the CMC and σ _m in values.

Product from Example 1: C44H7sNa2N2θi 7 = 953 g / mol (RS 786) Product from Example 5: C28H5fjNaNO- | 4 = 647.7 g / mol (RS 795) Product from Example 10 (RS 814): C44H78Na2N2θ2θS = 1033 g / mol

Table 1: CMC and σmin values

The results in Table 1 show the very good surfactant properties of the compounds (1) according to the invention, which, for example, exceed a commercially used standard surfactant (SDS).

Example 13: Measurement of foam height and foam stability

In special areas of application, for example for dishwashing detergents, well foaming surfactants are required. Data on the foam properties can be obtained, for example, using the Ross-M / es method (ASTM D1173-53, Oil & Soap 62, 1260, 1958). Then 200 ml of the surfactant solution are run into a measuring cylinder with 50 ml of the same surfactant solution using a pipette with an internal diameter of 2.9 mm and a height of 90 cm. The foam height was read off immediately (t = 0, IFH = initial foam height) and then at given times. With this experimental setup, the foam heights at 25 ° C and with a 0.1% concentration of the relevant invention Product from Example 1: RS 786; Product from Example 5: RS 795. The substance RS 795, which was still clearly soluble at up to 20 g / l, surprisingly showed practically no more waste within a period of up to 2 hours after the foam height had dropped slightly within the first 5 minutes. Even the less readily soluble substance RS 786, which could only be clearly dissolved in water up to 4 g / l, showed excellent foam stability after the initial drop. In contrast, the foam from SDS practically completely disappeared within about 100 minutes (see FIG. 6). The foam stability of the sulfonate produced according to Example 10 was also excellent: the foam height dropped here from 33 mm (product from Example 10) to 24 mm within 2 hours using the same test method.

Example 14: Dispersing effect

To determine the solubilization of Sudan Red B in water with the compounds according to the invention, solutions of various concentrations (0.075 g, 0.150 g and 0.300 g in 25 ml of water) were each mixed with 12.5 mg of Sudan Red B. The dye was dispersed by ultrasound. The suspension was then centrifuged at 7500 rpm for 70 min and membrane filtered. The absorbance of the clear solution above was measured photometrically at a wavelength of 516 nm (cuvette length 1 cm). A solution of Sudan Red B in water (12.5 mg in 25 ml) served as the zero sample. The compound referred to as "caprylate" is a capylate of the oxidized sucrose from example 10 in DE 19542303. This comparative compound is therefore significantly less effective than, for example, the compound from example 1. The same applies to low concentrations of up to 0.3% by weight the lower substituted compound from Example 5 (see Table 2, Fig. 7).

These measurement results show that the compounds according to the invention have excellent solubilization properties. The compounds are therefore suitable, for example, for detergents, dishwashing detergents and cleaning agents and as formulation auxiliaries in the pharmaceutical and agricultural sectors.

Example 15: Solubilization of an Active Ingredient

Active pharmaceutical ingredients and food additives for which no suitable dosage form is available can be better solubilized in water or incorporated into other formulations. Obvious examples of proof of efficacy include doxorubicin (tumor therapy), amphotericin (treatment of mycoses) and vitamins (additive). In the present example, 50 mg of vitamin E (tocopherol) was absorbed smoothly by only 150 mg of the compound from Example 1 without the addition of solvent (see Table 3). A dispersion test in water (25 ml) was carried out analogously to that described in Example 14: Tab. 3

Example 16: Preparation of active ingredient formulations for crop protection agents and for the treatment of seeds

Fungicides which are difficult to dissolve in water and insecticides in spray liquors (foliar sprays) or in seed dressings (seed treatment) can be better formulated with additions of the compounds according to the invention. A typical formulation is made up, for example, of 20-600 g of a fungicide or 10-500 g of an insecticide, 50-150 g of an antifreeze such as ethylene glycol or propylene glycol, 2-10 g of a defoamer, 2-100 g of a compound according to the invention and water (make up 1 liter of formulation).

Example 17: Hand washing test on healthy and sensitive / diseased skin

2 g of the product from Example 2 at 20 ° C. in 100 ml of water form a colorless, fine-pored foam-forming emulsion with a P | - | value of approximately 9. This emulsion was mixed with

Citric acid adjusted to the physiological pπ value of healthy skin, which is approximately 5.5. Hand washing tests with this solution resulted in a subjectively pleasant, irritation-free skin feeling as well as an excellent cleaning effect on healthy and also on stressed, sensitive skin, which is burdened by chronic dermatosis. A comparable treatment with ordinary soap caused the subject to develop severe itching in about 5 minutes, which was then treated with a corticosteroid ointment. had to. Formulations containing the compounds according to the invention are therefore particularly suitable for frequent washing, showering and bathing for sensitive or diseased skin, and also for cleaning, in particular, youthful skin. The subjectively mild character obviously gives the compounds a stabilizing effect on the protective acid mantle of the skin.

Example 18: Preparation of a shampoo

To produce 1 kg of a shampoo, 60 g of the compound according to the invention (for example from Example 1), 130 g of cocamido-propylbetaine, 15 g of NaCl, 1.5 g of preservative (for example potassium sorbate and / or sodium benzoate), 5 g allantoine, 2 g sodium formate, 7 g sodium citrate and 1 g perfume oil mixed and made up to 1 kg with water. This gives you a highly effective shampoo that is compatible with your skin and hair.

Example 19: Preparation of an abrasive

To produce 1 kg of an abrasive, 30 g of the compound according to the invention (e.g. from Example 2), 20 g of octadecyl polyethylene glycol ether, 45 g of pentasodium triphosphate and 2 g of fragrance are mixed and made up to 1 kg with quartz powder.

Example 20: Preparation of a detergent

To produce 1 kg of a detergent, 150 g of the compounds according to the invention (e.g. from Example 3), 200 g of complexing agents, e.g. Zeolite, 30 g detergent protease, 35 g sodium citrate, 80 ml ethanol and optionally fragrances and dyes mixed and made up to 1 kg with water.

Example 21: Preparation of a bath additive

To produce 1 kg of a bath additive, 20 g of the compound according to the invention (for example from Example 3), 45 g of coconut fatty acid ethanolamide, 50 g of man- del oil, 10 g sodium chloride, 3.5 g preservative, 10 g hexadecanol, and 10 g perfume mixed and made up to 1 kg with water.

Example 22: Testing biodegradability

According to OECD 301 B, substances can be classified as readily biodegradable if at least 60% of the carbon is mineralized to carbon dioxide after 28 days of contact with an activated sludge mixed population. In this test, a compound according to the invention (sample from Example 1) was metabolized to 60.3% after only 18 days. The substance is therefore very easily biodegradable.

Claims

claims

1. Sucrose-N-alkyl aspartate of the formula (I)

(l)

wherein R ^1, independently of one another, identically or differently, is a group selected from hydrogen, a compound of the formula (II):

(left)

with R ² equal to C _n H2n + ι or C _n H2n, where n is an integer from 2-28, preferably 6-22, especially 12-18, a compound of formula (IM)

(III)

and / or a radical of formula (IV) ff. ,

0 = S— O M (IV)

and M ⁺ is hydrogen, an alkali metal ion and / or an alkaline earth metal ion, preferably a sodium, potassium, lithium, magnesium, calcium and / or ammonium ion with the requirement that at least one radical R ^{1 is} a compound of the formula ( II) is.

2. Sucrose-N-alkyl aspartate according to claim 1, characterized in that the degree of substitution of the radical R ¹ (DS) is determined by the following formula: DS = nx [radical of the formula (II)] + [0 to (8-n) ] x [rest of formula (III)] + (0 to m) x [rest of formula (IV)], where m = 2 for n = 1-6 and m = 1 for n = 7 and n <8.

3. sucrose-N-alkyl aspartate according to claim 1 or 2, characterized in that R ² is a decyl, dodecyl, tetradecyl, hexadecyl or octadecyl radical or a radical derived from coconut, palm, soy or tallow oil fats, or mixtures thereof.

4. A process for the preparation of a sucrose-N-alkylaspartate of the formula (I), characterized in that sucrose is acylated with maleic acid or a derivative of maleic acid in a first step, and in a second step one to eight molar equivalents of amine of the formula R ² NH ₂ with R ² equal to C _n H _2n + ι or CnH _2n , where n is an integer from 2-28, preferably 6-22, especially 12-18, is added to the maleate sucrose formed in the first step.

5. The method according to claim 4, characterized in that the acylation reaction is carried out in the presence of a catalyst.

6. The method according to claim 5, characterized in that the catalyst is a basic metal salt, preferably a carbonate, hydrogen carbonate, acetate and / or formate.

7. The method according to any one of claims 4-6, characterized in that in a further step the sucrose-N-alkylaspartate obtained is sulfonated.

8. The method according to claim 7, characterized in that up to two radicals R ^{1 are} sulfonated.

9. The method according to claim 7 or 8, characterized in that the sulfonation is carried out with SO ₃ , CISO ₃ H, DMF-SO3 and / or pyridine-S0 ₃ .

10. Use of a sucrose-N-alkyl aspartate according to one of claims 1 -3 as a surface-active compound.

11. Use of one or more sucrose-N-alkylasparaginates according to any one of claims 1-3 as an additive in hygiene, cleaning, cosmetic, food and / or pharmaceuticals or in pesticides or for the prevention and / or control of pollution of the water through chemicals and / or oil.

12. Use according to claim 11 as an additive in soaps, abrasives, all-purpose cleaners, dishwashing detergents, detergents, shampoos, heavy-duty detergents and / or bath additives.

13. Use according to claim 11 or 12, characterized in that the degree of substitution DS of at least one sucrose-N-alkyl aspartate is between 1 to about 4.

14. Use according to any one of claims 10-13, characterized in that the sucrose-N-alkyl aspartate is used together with at least one other surface-active substance (co-surfactant).

15. Use according to claim 14, characterized in that the co-surfactant is selected from alkyl polyglycosides, 6-0-monoesteralkyl glycosides, alcohol ether sulfates or alkyl glucamides.

16. Use of a sucrose-N-alkylasparaginate according to any one of claims 1-3 as a low-calorie fat substitute.

17. Use according to claim 16, characterized in that the degree of substitution DS of at least one sucrose-N-alkyl aspartate is between about 4 and 8.

18. Use of a sucrose-N-alkylasparaginate according to any one of claims 1-3 as a transfection reagent.

19. Sucrose-N-alkyl aspartate according to one of claims 1-3 in the form of an aqueous solution, emulsion, suspension, jelly, cream, paste or powder.