EP1725520A2 - Formulation auxiliary agents (aminopropanoic acid derivative) in cosmetic or dermatoligical preparations - Google Patents

Abstract

The invention relates to compounds of formula (I) wherein R<1>, R<2> and R<3> can be the same or different and are selected from linear or branched C1-C24 alkyl groups, linear or branched C3-C24 alkenyl groups, linear or branched C1-C24 hydroxyalkyl groups - the hydroxy groups can be bound to a primary or secondary carbon atom of the chain, and the alkyl chain can also be interrupted by oxygen - and/or C3-C10 cycloalkyl groups, and/or C3-C12 cycloalkenyl groups. The rings can also be respectively bridged by CH2)n groups where n = 1 to 3. The invention also relates to the use of said compounds as formulation auxiliary agents for producing cosmetic or dermatological preparations, to the corresponding novel compounds, and to the production thereof.

Description

 formulation aid

The present invention relates to the use of certain substances as formulation auxiliaries for the production of cosmetic or dermatological preparations, corresponding new compounds and their production.

One area of use of the formulation auxiliaries according to the invention is, for example, cosmetics. The aim of cosmetic care is to give the impression of youthful skin if possible. In principle, there are various ways to achieve this. Existing damage to the skin, such as irregular pigmentation or wrinkles, can be compensated for by covering powders or creams. Another starting point is to protect the skin from environmental influences that lead to permanent damage and thus aging of the skin. So the idea is to intervene preventively and thereby delay the aging process. An example of this are the UV filters already mentioned, which prevent or at least reduce damage to the skin by absorbing certain wavelength ranges. While with UV filters the damaging one

Another way to support the natural defense or repair mechanisms of the skin against the damaging event is to try to prevent the event that UV radiation is shielded from the skin. Finally, another starting point is to compensate for the weakening of the defense functions of the skin against damaging influences with increasing age by adding substances from outside which can replace this weakening defense or repair function. For example, the skin has the ability to trap radicals that are generated by external or internal stress factors. This ability weakens with increasing

Age decreases, which accelerates the aging process with increasing age.

Skin damage is not only caused by sunlight, but also by other external influences, such as cold or heat. The skin is also subject to natural aging, which creates wrinkles and reduces the elasticity of the skin.

There are various active ingredients, e.g. Classical like UV filters and antioxidants or modern active ingredients that go directly into the biochemical

Intervening processes in the skin are known which are suitable for the prophylaxis, treatment or relief of the symptoms of the skin stress symptoms described above.

However, a further difficulty in the production of cosmetics is that many of these active ingredients, which are to be incorporated into cosmetic preparations, are often not or only sparingly soluble, are not stable and can be damaged in the preparation or have to be used in large amounts or reduce the stability of the resulting formulations.

The damage can be caused, for example, by a reaction with atmospheric oxygen or by the absorption of UV rays. The molecules damaged in this way can e.g. change color and / or lose effectiveness.

There is therefore a need for auxiliaries which, in combination with the respective active ingredients, are suitable for solving one or more of the problems mentioned.

The object of the invention is therefore to provide a formulation aid which can be incorporated into cosmetic preparations and which, in combination with suitable active ingredients, facilitates their incorporation and / or their effectiveness and / or their

Stability improved and / or the stability of the resulting formulation increased.

This object is surprisingly achieved by the use of certain β-alanine derivatives as formulation auxiliaries for the production of cosmetic or dermatological preparations. A first object of the present invention is therefore the use of a compound of formula I.

where R ¹ , R ² and R ^{3 may be the} same or different and are selected from straight-chain or branched C to C ₂₄ alkyl groups, straight-chain or branched C ₃ to C ₂ alkenyl groups, straight-chain or branched C to C ₂₄ hydroxyalkyl groups wherein the hydroxyl group may be bonded to a primary or secondary carbon atom of the chain and furthermore the alkyl chain may also be interrupted by oxygen, and / or C ₃ - to C _t o-cycloalkyl and / or C ₃ - to C ₁₂ - cycloalkenyl , where the rings can also be bridged by - (CH ₂ ) _n - groups with n = 1 to 3, as formulation aids in the production of cosmetic or dermatological preparations.

Thus, in preferred embodiments of the present

Invention, the compounds mentioned serve as solubilizers, penetration enhancers and / or effect enhancers.

Some of the compounds of formula I with radicals as defined above or structurally similar compounds are known from the literature:

- 3- (Acetyl-butyl-amino) -propionic acid ethyl ester is a known insect repellent which is sold under the trade name IR3535 ^® by Merck.

- The suitability of other ß-alanine derivatives as insect repellents is in M. Klier, F. Kuhlow, J. Soc. Cos. Chem., 27, pp. 141-153 (1976). It may be preferred according to the invention if the compound 3- (acetyl-butylamino) propionic acid ethyl ester known as insect repellent is excluded from the compounds of the formula I.

It has been shown that there are such for use according to the invention

Compounds are particularly suitable in which R ¹ and R ^{3 may be the} same or different and are selected from ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl , n-heptyl, n-octyl, 2-ethyl-hexyl, n-decyl, n-dodecyl, n-tetradecane, n-hecadecane, n-octadecane, n-eicosane, n-docosane and n-tetracosane, where R ¹ preferably represents 2-ethyl-hexyl and / or R ³ preferably represents n-octyl, 2-ethyl-hexyl, n-decyl or n-dodecyl.

According to the invention, preference is also given to using compounds in which R ^{2 is} selected from the group consisting of

Contains elements methyl, n-propyl, isopropyl, n-pentyl, n-heptyl, 1-ethyl-pentyl, n-nonyl, n-undecyl, where R ^{2 is} preferably selected from the group consisting of the elements methyl, 1 -Ethyl-pentyl, n-nonyl and n-undecyl contains.

In detail, the compounds listed below have proven to be particularly suitable for the use according to the invention:

- N-acetyl-N- (2-ethylhexyl) -3-aminopropanoic acid, - N-acetyl-N- (dodecyl) -3-aminopropanoic acid,

- N- (2-ethylhexoyl) -N- (butyl) -3-aminopropanoic acid ethyl ester,

Butyl N-acetyl-N- (butyl) -3-aminopropanoate,

- N- (2-ethylhexoyl) -N- (2-ethylhexyl) -3-aminopropanoic acid ethyl ester, N- (2-ethylhexoyl) -N- (dodecyl) -3-aminopropanoic acid ethyl ester, - N-acetyl-N- (2-ethylhexyl ) -3-aminopropansäurebutylester,

Butyl N-acetyl-N- (dodecyl) -3-aminopropanoate,

- butyl N- (2-ethylhexoyl) -N- (butyl) -3-aminopropanoate,

Butyl N- (2-ethylhexoyl-N- (2-ethylhexyl) -3-aminopropanoate,

- butyl N- (2-ethylhexoyl) -N- (dodecyl) -3-aminopropane, - 2-ethylhexyl N-acetyl-N- (butyl) -3-aminopropanoate,

N-acetyl-N- (2-ethylhexyl) -3-aminopropanoic acid 2-ethylhexyl ester, - N-Acetyl-N- (dodecyl) -3-aminopropanoic acid 2-ethylhexyl ester, N- (2-ethylhexoyl) -N- (butyl) -3-aminopropanoic acid 2-ethylhexyl ester, N- (2-ethylhexoyl) -N - (2-ethylhexyl) -3-aminopropanoic acid 2-ethylhexyl ester, N- (2-ethylhexoyl) -N-dodecyl) -3-aminopropanoic acid 2-ethylhexyl ester, the compound of formula I being particularly preferred N-acetyl-N- (2-ethylhexyl) -3-aminopropanoic acid ethyl ester. The new compounds with the suitability according to the invention are a further subject of the present application. Compounds according to formula I are therefore claimed

where R ¹ , R ² and R ^{3 may be the} same or different and are selected from - straight-chain or branched Ci to C ₂₄ alkyl groups, - straight-chain or branched C ₃ - to C ₂₄ alkenyl groups, - straight-chain or branched d- bis C ₂₄ -hydroxyalkyl groups, where the hydroxy group can be bound to a primary or secondary carbon atom of the chain and the alkyl chain can also be interrupted by oxygen, and / or - C ₃ - to Cio-cycloalkyl groups and / or C ₃ - to Cι ₂ - Cycloalkenyl groups, where the rings can also be bridged by - (CH ₂ ) _n - groups with n = 1 to 3, with the proviso that either R ^{1 is} 2-ethylhexyl or R ^{2 is} 1 -ethyl- pentyl and R ^{3 are} n-octyl, 2-ethyl-hexyl, n-decyl or n-dodecyl or R ^{2 is} methyl and R ¹ and R ^{3 are} different or the compound of formula I is N- ( 2-Ethylhexoyl) -N- (butyl) -3-aminopropanoic acid butyl ester. Preferred new compounds are characterized in that R ¹ preferably represents 2-ethyl-hexyl and / or R ³ preferably represents n-octyl, 2-ethyl-hexyl, n-decyl or n-dodecyl.

Particularly preferred new compounds are listed below:

- N- (2-ethylhexoyl) -N- (2-ethylhexyl) -3-aminopropanoic acid ethyl ester,

- N- (2-ethylhexoyl) -N- (dodecyl) -3-aminopropanoic acid, ethyl ester, N-acetyl-N- (2-ethylhexyl) -3-aminopropanoic acid butyl ester, - N-acetyl-N- (dodecyl) -3-aminopropanoic acid butyl ester,

- butyl N- (2-ethylhexoyl) -N- (butyl) -3-aminopropanoate,

Butyl N- (2-ethylhexoyl-N- (2-ethylhexyl) -3-aminopropanoate,

Butyl N- (2-ethylhexoyl) -N- (dodecyl) -3-aminopropane,

- 2-ethylhexyl N-acetyl-N- (butyl) -3-aminopropanoate, - 2-ethylhexyl N-acetyl-N- (2-ethylhexyl) -3-aminopropanoate,

2-ethylhexyl N-acetyl-N- (dodecyl) -3-aminopropanoate,

- N- (2-ethylhexoyl) -N- (butyl) -3-aminopropanoic acid 2-ethylhexyl ester, N- (2-ethylhexoyl) -N- (2-ethylhexyl) -3-aminopropanoic acid 2-ethylhexyl ester, N- (2-Ethylhexoyl) -N-dodecyl) -3-aminopropanoic acid 2-ethylhexyl ester.

The compounds which are suitable for the use according to the invention can be prepared by methods known per se: A compound of the formula II is preferably used in the preparation

is reacted with an acid derivative R, 2 -C (= O) -X, where X is -CI, -OC (= O) -R ⁴ or -OR ⁴ , where -R ⁴ is a straight-chain or branched C to C 1-4 alkyl group, which is preferably identical to R ² . In a particularly preferred variant of the production process, the acid derivative is an acid anhydride R ² -C (= O) -OC (= O) -R ² . The reaction can be carried out in bulk or in customary aprotic solvents. An ethereal solvent such as diethyl ether, tetrahydrofuran (THF), tert-butyl methyl ether (MTBE) or dibutyl ether can preferably be used as the solvent. However, other polar solvents such as methylethyiketone and the like can also be used, but also apolar solvents such as n-hexane, heptane, toluene, etc.

The compound of the formula II is preferably prepared by reacting a compound of the formula III

with an amine R ³ -NH ₂ . Reaction conditions for these reactions are also familiar to the person skilled in the art and can be adapted to the respective radicals R ¹ or R ³ without difficulty.

The reaction can be carried out in bulk or in customary aprotic solvents. An ethereal solvent such as diethyl ether, tetrahydrofuran (THF), tert-butyl methyl ether (MTBE) or dibutyl ether can preferably be used as the solvent. However, other polar solvents can also be used, but also non-polar solvents such as e.g. n-hexane, heptane, toluene, etc.

This preferred manufacturing process for the new compounds according to

Formula I is a further object of the present invention.

The present invention further provides preparations comprising at least one formulation aid of the formula I.

wherein R, R ² and R ^{3 may be the} same or different and are selected from

straight-chain or branched C 1 to C ₂₄ alkyl groups, straight-chain or branched C ₃ to C ₂₄ alkenyl groups,

- Straight-chain or branched d- to C ₂₄ -hydroxyalkyl groups, where the hydroxy group can be bound to a primary or secondary carbon atom of the chain and the alkyl chain can also be interrupted by oxygen, and / or - C ₃ - to C-io-cycloalkyl groups and / or C ₃ to C- ₂ cycloalkenyl groups, where the rings can also be bridged by - (CH ₂ ) _n groups with n = 1 to 3, and at least one active substance, the processing and / or application thereof the formulation aid is facilitated, ethyl 3- (acetyl-butylamino) propionate being excluded from the compounds of the formula I.

The preparations are usually topically applicable preparations, for example cosmetic or dermatological formulations. The preparations contained in this

Case a cosmetically or dermatologically suitable carrier and, depending on the desired property profile, optionally further suitable ingredients.

According to the invention, the compounds of the formula I are typically used in amounts of 0.01 to 20% by weight, preferably in amounts of 0.1% by weight.

% to 10 wt .-% and particularly preferably used in amounts of 1 to 8 wt .-%. It is no problem for the person skilled in the art to select the amounts appropriately depending on the intended action of the preparation.

The active substances to be used according to the invention include so-called repellents, in particular insect repellents.

A variety of mosquitoes, fleas, fleas, lice, bugs, ticks and mites, in the further course under the collective terms

Insects and spiders - or simplifying even under the im biological meaning improperly used generic term insects - in summary, feed on the blood of the warm-blooded animals, which also include humans. They pierce their victims' skin with their piercing and suction tools until they encounter blood vessels. During food intake, they secrete vasodilators and anticoagulants, which can lead to itching, wheals and allergic reactions in the host. In the tropics and subtropics in particular, there is also a risk of infection with pathogens. For example, malaria is caused by the Anopheles mosquito or yellow fever by the

Yellow fever mosquito transmitted. Even in temperate regions, there is a risk of infection with insect-borne pathogens, such as tick-borne tick-borne encephalitis.

So-called repellents offer protection against the annoyance of insects and spiders. This is a series of active substances that, through their smell, have a repellent effect on insects and spiders. These are usually low-volatility compounds that slowly evaporate on the skin and thus one

Form a scent bell over the skin that drives the insects away.

The most common repellents include N, N-diethyl-3-methylbenzamide ("DEET"), which is active against mosquitoes, mosquito and sand flies, brakes, fleas, bugs, ticks and mites.

Dimethyl phthalate (trade name: Palatinol M, DMP) is also used against mosquitoes, lice, ticks and mites. Ethyl 3- (N-n-butyl-N-acetylamino) propionate (available under the trade name IR3535 ^® from Merck) is particularly effective and can be used, for example, against mosquitoes, tsetse flies and brakes.

Most repellent agents belong to the classes of amides,

Alcohols, esters and ethers. Repellent active ingredients should usually meet the following conditions: They must not evaporate too quickly and must not penetrate the skin. You may go to the Skin is neither primarily irritating nor sensitizing and should also not be toxic. Their effectiveness must also be maintained when exposed to skin fluid and / or UV radiation.

Accordingly, the invention as

Compounds of the formula I employed in formulation auxiliaries have a supporting effect here by

- extend the duration of action of the repellents on the skin,

- Stabilize the repellents against UV radiation and / or skin fluids and / or

- Enhance the effect of the repellents and thus enable the use of smaller amounts of repellants in the formulation.

It is therefore preferred if the preparation according to the invention contains at least one repellent, the repellent preferably being selected from N, N-diethyl-3-methylbenzamide, 3- (acetyl-butylamino) propionic acid, ethyl ester, dimethylphthalate, butopyronoxyl, 2,3 , 4, 5-bis- (2-

Butylene) tetrahydro-2-furaldehyde, N, N-caprylic acid diethylamide, N, N-

Diethylbenzamide, o-chloro-N, N-diethylbenzamide, N- (2-ethylhexyl) -8,9,10-trinorborn-5-en-2,3-dicarboximide, dimethyl carbate, di-n-propylisocinchomeronate, (R. ) -p-Mentha-l, 8-diol, 2-ethylhexane-1,3-diol, N-octyl-bi-cyclo-hepetenediecarboximide, piperonyl butoxide, 1 - (2-methylpropyloxycarbonyl) -

2- (hydroxyethyl) -piperidine (Bayrepel ^®; Fa. Bayer) or mixtures thereof, and it is particularly preferably selected from NN-diethyl-3-methylbenzamide, 3- (acetyl-butyl-amino) -propionic acid ethyl ester 1- ( 2

Methylpropyloxycarbonyl) -2- (hydroxyethyl) piperidine or mixtures thereof.

The preparations according to the invention which contain repellents are preferably insect repellants.

Insect repellents are offered in the form of solutions, gels, pens, rollers, pump sprays and aerosol sprays, with solutions and sprays forming the main part of the commercially available products. These two product forms are usually based on alcoholic or aqueous-alcoholic solutions with the addition of fatty substances and light perfuming. Other forms of preparation, such as in particular In principle, emulsions, creams, ointments and the like are conceivable and desirable, but have so far been difficult to formulate in a stable manner. The formulation auxiliaries according to the invention can also be used advantageously here.

In a further preferred embodiment of the present invention, which can also be combined with the one just described, the at least one active substance is an insoluble or poorly soluble active substance.

It has been shown that the use of the compounds of the formula I here can lead to an advantageous improvement in the dispersing properties of active substances which are insoluble or poorly soluble per se.

Such insoluble or poorly soluble active substances are preferably selected from the group of organic UV filters, flavone derivatives, chromone derivatives, aryloximes or parabens.

Parabens are 4-hydroxybenzoic acid esters, which in free form or as sodium salts for the preservation of preparations in the field

Food, cosmetics and pharmaceuticals are used. The effect of the esters is directly proportional to the chain length of the alkyl radical, but conversely the solubility decreases with increasing chain length. As non-dissociating compounds, the esters are largely independent of pH and act in a pH range of 3.0-8.0. The antimicrobial mechanism of action is based on damage to the microbe membranes by the surface activity of the PHB esters and on protein denaturation. Interactions with coenzymes also occur. The effect is directed against fungi, yeasts and bacteria. The most important parabens as preservatives are 4-

Methyl hydroxybenzoate, ethyl 4-hydroxybenzoate, propyl 4-hydroxybenzoate, butyl 4-hydroxybenzoate. These compounds, which are often only called methyl, ethyl, propyl, butyl paraben, are only poorly soluble in common carriers for the preparations to be preserved. Therefore, the use of the compounds may vary

Formula I the incorporation of parabens, especially 4- Methyl hydroxybenzoic acid, ethyl 4-hydroxybenzoate, propyl 4-hydroxybenzoate, butyl 4-hydroxybenzoate in preparations. Among the aryl oximes, which are also difficult to dissolve in conventional carriers for cosmetic and dermatological preparations, 2-hydroxy-5-methyllaurophenone oxime, which is also referred to as HMLO, LPO or F5, is preferably used. Its suitability for use in cosmetic products is known, for example, from German Offenlegungsschrift DE-A-41 16 123. Preparations containing 2-

Hydroxy-5-methyllaurophenone oxime are therefore suitable for the treatment of skin diseases which are associated with inflammation. It is known that such preparations e.g. can be used to treat psioriasis, various forms of eczema, irritative and toxic dermatitis, UV dermatitis and other allergic and / or inflammatory diseases of the skin and the appendages of the skin. Preparations according to the invention which, in addition to the compound of the formula I, additionally contain an aryl oxime, preferably 2-hydroxy-5-methyllaurophenone oxime, show surprising anti-inflammatory suitability. The preparations preferably contain 0.01 to 10% by weight of the aryloxime, it being particularly preferred if the preparation contains 0.05 to 5% by weight aryloxime.

According to the invention, flavonoids and coumaranones are understood as flavone derivatives. According to the invention, the flavonoids are

Glycosides of flavanones, flavones, 3-hydroxyflavones (= flavonols), aurones, isoflavones and Rotenoiden [Römpp Chemie Lexikon, Volume 9, 1993]. Within the scope of the present invention, however, the agycones, i.e. understood the sugar-free ingredients, and the derivatives of the flavonoids and agiycones. Furthermore, in

Within the scope of the present invention, the term flavonoid is also understood to mean anthocyanidin (cyanidin). In the context of the present invention, coumaranones are also understood to mean their derivatives. Preferred flavonoids are derived from flavanones, flavones, 3-hydroxyflavones, aurones and isoflavones, in particular from flavanones, flavones, 3-hydroxyflavones and aurones.

The flavonoids are preferably selected from the following

Compounds: 4,6,3 ^' , 4 ^' -Tetrahydroxyauron, Quercetin, Rutin, Iso-quercetin, Eriodictyol, Taxifolin, Luteolin, Trishydroxyethylquercetin (Troxequercetin), Trishydroxyethylrutin (Troxerutin), Trishydroxyethyliso- quercetin (Troxeisuteolinol), α-glycosyl rutin, tiliroside and their sulfates and phosphates. Among the

Flavonoids are preferred as active substances according to the invention, in particular rutin, tiliroside, α-glycosylrutin and troxerutin.

Among the coumaranones, 4,6,3 ', 4'-tetrahydroxybenzylcoumaranone-3 is preferred.

Chromone derivatives are preferably understood to mean certain chromene-2-one derivatives which are suitable as active ingredients for the preventive treatment of human skin and hair against aging processes and damaging environmental influences. At the same time, they show a low irritation potential for the skin, have a positive effect on the water binding in the skin, maintain or increase the elasticity of the skin and thus promote smoothing of the skin. These compounds preferably correspond to formula IV

in which

R ¹ and R ^{2 may be the} same or different and are selected from

H, -C (= O) -R ⁷ , -C (= O) -OR ⁷ , straight-chain or branched d to C ₂₀ alkyl groups,

straight-chain or branched C ₃ to C ₂ o-alkenyl groups, straight-chain or branched d to C ₂₀ hydroxyalkyl groups, it being possible for the hydroxy group to be bound to a primary or secondary carbon atom of the chain and furthermore the alkyl chain can also be interrupted by oxygen, and / or C ₃ - to C-io-cycloalkyl groups and / or C ₃ - to C ₁₂ - cycloalkenyl groups, where the rings can also be bridged by - (CH ₂ ) _n groups with n = 1 to 3, R ³ stands for H or straight-chain or branched Ci to C ₂ o -alkyl groups, R ⁴ stands for H or OR ⁸ , R ⁵ and R ^{6 may be the} same or different and are selected from - -H, -OH, straight-chain or branched C. to C ₂ o -alkyl groups, - straight-chain or branched C ₃ - to C ₂ o-alkenyl groups, straight-chain or branched Cr to C ₂ o-hydroxyalkyl groups, where the hydroxy group can be bonded to a primary or secondary carbon atom of the chain and further the alkyl chain can also be interrupted by oxygen and R ⁷ stands for H, straight-chain or branched d- to C ₂ o -alkyl groups, a polyhydroxy compound, such as preferably an ascorbic acid residue or glycosidic residues and R ⁸ stands for H or straight-chain or branched d- bis C ₂ o -alkyl groups, where at least 2 of the substituents R ¹ , R ² , R ⁴ -R ^{6 are} different from H or at least one substituent from R ¹ and R ² for -C (= O) -R ⁷ or - C ( = O) -OR ⁷ stands.

The proportion of one or more compounds selected from flavonoids, Cromon derivatives and coumaranones in the preparation according to the invention is preferably from 0.001 to 5% by weight, particularly preferably from 0.01 to 2% by weight, based on the overall preparation.

When the dibenzoylmethane derivatives, which are particularly preferred as UV-A filters, are used in combination with the compounds of the formula I, there is an additional advantage: the UV-sensitive ones Dibenzoylmethane derivatives are additionally stabilized by the presence of the compounds of the formula I. The present invention therefore furthermore relates to the use of the compounds of the formula I for stabilizing dibenzoylmethane derivatives in preparations.

Preferred preparations with light protection properties contain at least one dibenzoylmethane derivative. As already shown, the dibenzoylmethane derivatives used in the context of the present invention are, in themselves, already well-known products, which are described in particular in the above-mentioned documents FR-A-2 326 405, FR-A-2 440 933 and EP-A-0 114 607 are described.

The dibenzoylmethane derivatives which can be used according to the invention can be selected in particular from the dibenzoylmethane derivatives of the following formula:

wherein R ¹ , R ² , R ³ and R ⁴ , which are identical or different from each other, signify hydrogen, a straight-chain or branched ds-alkyl group or a straight-chain or branched C _-8 alkoxy group. According to the present invention, one or more dibenzoylmethane derivatives can of course be used. Of the dibenzoylmethane derivatives to which the present invention relates more particularly, in particular:

- 2-methyldibenzoylmethane,

4-methyldibenzoylmethane,

4-isopropyldigenzoylmethane,

- 4-tert-butyldibenzoylmethane, - 2,4-dimethyldibenzoylmethane,

- 2,5-dimethyldibenzoylmethane, - 4,4'-diisopropyldibenzoylmethane, - 4,4'-methoxy-tert-butyldibenzoylmethane, - 2-methyl-5-isopropyl-4'-methoxydibenzoylmethane, - 2-methyl-5-tert-butyl-4'-methoxydibenzoylmethane, - 2,4-dimethyl -4'-methoxydibenzoylmethane and

- 2,6-Dimethyl-4-tert-butyl-4'-methoxydibenzoylmethane may be mentioned, but this list is not restrictive.

Of the above dibenzoylmethane derivatives erfindungsge- is measured, in particular the 4,4'-methoxy-t-butyldibenzoylmethane, and in particular the left under the trade name Eusolex ^® 9020 from Merck commercially 4,4'-methoxy-t-butyldibenzoylmethane preferred, this filter corresponding to the following structural formula:

Another preferred dibenzoylmethane derivative according to the invention is 4-isopropyldibenzoylmethane.

It has also been found that compounds of the formula I can have a stabilizing effect on the preparation. When used in corresponding products, they therefore remain stable for longer and do not change their appearance. In particular, even with prolonged use or storage, the effectiveness of

Ingredients, e.g. Vitamins. Among other things, this is particularly advantageous in the case of compositions for protecting the skin against the action of UV rays, since these cosmetics are exposed to particularly high levels of exposure to UV radiation.

Preparations which are particularly preferred according to the invention contain not only the compounds of the formula I but also UV filters. In principle, all UV filters can be used in combination with the compounds of the formula I according to the invention. Those UV filters whose physiological harmlessness has already been proven are particularly preferred. Both for UVA and UVB filters there are many well-known and proven substances from the specialist literature, e.g.

Benzylidene camphor derivatives such as 3- (4 ^' -methylbenzylidene) -dl-camphor (e.g. Eusolex® 6300), 3-benzylidene camphor (e.g. Mexoryl® SD), polymers of N - {(2 and 4) - [(2-oxobom-3- ylidene) methyl] benzyl} acrylamide (e.g. Mexoryl®

SW), N, N, N-Trimethyl-4- (2-oxobom-3-ylidenmethyl) anilinium methyl sulfate (e.g. Mexoryl® SK) or (2-Oxoborn-3-yliden) toluene-4-sulfonic acid (e.g. Mexoryl® SL )

Benzoyl- or dibenzoylmethanes such as 1- (4-tert-butylphenyl) -3- (4-methoxyphenyl) propane-1, 3-dione (e.g. Eusolex® 9020) or 4-isopropyldibenzoylmethane (e.g. Eusolex® 8020),

Benzophenones such as 2-hydroxy-4-methoxybenzophenone (e.g. Eusolex® 4360) or 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and the like

Sodium salt (e.g. Uvinul® MS-40),

Methoxycinnamic acid esters such as octyl methoxycinnamate (e.g. Eusolex® 2292), isopentyl 4-methoxycinnamate, e.g. as a mixture of the isomers (e.g. Neo Heliopan® E 1000),

Salicylate derivatives such as 2-ethylhexyl salicylate (e.g. Eusolex® OS), 4-isopropylbenzyl salicylate (e.g. Megasol®) or 3,3,5-

Trimethylcyclohexyl salicylate (e.g. Eusolex® HMS),

4-aminobenzoic acid and derivatives such as 4-aminobenzoic acid, 4- (dimethylamino) benzoic acid-2-ethylhexyl ester (e.g. Eusolex® 6007), ethoxylated 4-aminobenzoic acid ethyl ester (e.g. Uvinul® P25),

Phenylbenzimidazole sulfonic acids, such as 2-phenylbenzimidazole-5-sulfonic acid and their potassium, sodium and triethanolamine salts (e.g. Eusolex® 232), 2,2- (1,4-phenylene) bisbenzimidazole-4,6-disulfonic acid or its salts (e.g. Neoheliopan® AP) or 2,2- (1,4-phenylene) bisbenzimidazole-6-sulfonic acid ;

and other substances like

- 2-cyano-3,3-diphenylacrylic acid 2-ethylhexyl ester (e.g. Eusolex® OCR),

- 3,3 ^' - (1,4-phenylenedimethylene) -bis- (7,7-dimethyl-2-oxobicyclo- [2.2.1] hept-1-ylmethanesulfonic acid as well as their salts (e.g. Mexoryl® SX) and

- 2,4,6-trianilino- (p-carbo-2 ^{'-ethylhexyl-1'} -oxi) -1, 3,5-triazine (for example Uvinul T 150)

- 2- (4-Diethylamino-2-hydroxy-benzoyl) -benzoic acid hexyl ester (e.g. Uvinul®UVA Plus, from BASF).

The compounds in the list are only examples. Of course, other UV filters can also be used.

These organic UV filters are generally incorporated into cosmetic formulations in an amount of 0.5 to 10 percent by weight, preferably 1-8%.

Other suitable organic UV filters are e.g.

- 2- (2H-Benzotriazol-2-yl) -4-methyl-6- (2-methyl-3- (1, 3,3,3-tetramethyl-1 - (trimethylsilyloxy) disiloxanyl) propyl) phenol (e.g. silatrizole ^® ), - 4,4 '- [(6- [4 - ((1, 1-dimethylethyl) aminocarbonyl) phenylamino] -1, 3,5-triazine-2,4-diyl) diimino] bis (benzoic acid-2 -ethylhexyl ester) (e.g. Uvasorb ^® HEB),

- α- (Trimethylsilyl) -ω- [trimethylsilyloxy] poly [oxy (dimethyl) silylene] [and about 6% methyl [2- [p- [2,2-bis (ethoxycarbonyl] vinyl] phenoxy] -1-methyleneethyl ] and approx. 1.5% methyl [3- [p- [2,2-bis (ethoxycarbonyl) vinyl) phenoxy) propenyl) and 0.1 to 0.4% (methylhydrogen) silylene]] (n »60 ) (CAS No. 207 574-74-1)

- 2,2 ^' -methylene-bis- (6- (2H-benzotriazol-2-yl) -4- (1, 1, 3,3-tetramethylbutyl) phenol) (CAS No. 103 597-45- 1) - 2,2 '- (1,4-phenylene) bis- (1 H-benzimidazole-4,6-disulfonic acid, monosodium salt) (CAS No. 180 898-37-7) and - 2,4-bis - {[4- (2-ethylhexyloxy) -2-hydroxyl] phenyl} -6- (4-methoxyphenyl) - 1,3,5-triazine (CAS No. 103 597- 45-, 187 393-00-6).

- 4,4 ^' - [(6- [4 - ((1, 1-dimethylethyl) aminocarbonyl) phenylamino] -1, 3,5-triazine-2,4-diyl) diimino] bis (2-ethylhexyl benzoate) (e.g. Uvasorb ^® HEB),

Other suitable UV filters are also methoxy flavones according to the older German patent application DE 10232595.2.

Organic UV filters are generally incorporated into cosmetic formulations in an amount of 0.5 to 20 percent by weight, preferably 1-15%.

In particular when using the insoluble or poorly soluble UV filters from the above list or organic particulate UV filters, as described, for example, in patent application WO 99/66896, a better distribution of the UV filters can be achieved by using the formulation aids according to the invention the formulation and thus a more even distribution of the UV filters on the skin. The stability, in particular the storage stability, of the formulations, in particular of emulsions which contain these UV filters, can also be improved by

Use of the formulation auxiliaries according to the invention can be increased.

In order to ensure optimized UV protection, it is further preferred if preparations with light protection properties also contain inorganic UV filters. Conceivable inorganic UV filters are those are possible from the group of titanium dioxides, such as coated titanium dioxide (for example Eusolex® T-2000, Eusolex ^® T-AQUA), zinc oxides (eg Sachtotec.RTM), iron oxides and also cerium oxides. These inorganic UV filters are generally incorporated into cosmetic preparations in an amount of 0.5 to 20 percent by weight, preferably 2 to 10%.

Preferred compounds with UV-filtering properties are 3- (4 ^' - methylbenzylidene) -dl-camphor, 1- (4-tert-butylphenyl) -3- (4-methoxy-phenyl) - pro-pan-1, 3-dione , 4-Isopropyldibenzoylmethane, 2-Hydroxy-4-meth-oxy-ben-zo-phenone, Methoxycinnamic Acid Octyl Ester, 3,3,5-Trimethyl-cyclo-hexyl-salicylate, 4- (Dimethylamino) Benzoic Acid-2-ethyl hexyl ester, 2-cyano-3,3- 2-ethylhexyl di-phenyl-acrylic acid, 2-phenyl-benzimidazole-5-sulfonic acid and its potassium, sodium and triethanolamine salts.

The protective effect against harmful effects of UV radiation can be optimized by combining one or more compounds of the formula I with further UV filters.

Optimized compositions can, for example, combine the organic UV filter 4'-methoxy-6-hydroxyflavon with 1- (4-tert-butylphenyl) -3- (4-methoxyphenyl) propane-1, 3-dione and 3- (4 ^' -

Methylbenzylidene) dl camphor contain. This combination provides broadband protection, which can be supplemented by adding inorganic UV filters such as titanium dioxide microparticles.

All of the UV filters mentioned can also be used in encapsulated form. In particular, it is advantageous to use encapsulated organic UV filters. The individual advantages are as follows: - The hydrophilicity of the capsule wall can be set independently of the solubility of the UV filter. For example, hydrophobic UV filters can also be incorporated into purely aqueous preparations. In addition, the oily impression, which is often perceived as unpleasant, is prevented when the preparation containing the hydrophobic UV filter is applied. - Certain UV filters, especially dibenzoylmethane derivatives, show only a reduced photostability in cosmetic preparations. By encapsulating these filters or compounds that impair the photostability of these filters, such as cinnamic acid derivatives, the photostability of the entire preparation can be increased. - In the literature, skin penetration is repeatedly caused by organic

UV filters and the associated potential for irritation when applied directly to human skin are discussed. This effect is prevented by the encapsulation of the corresponding substances proposed here. - Generally, by encapsulating individual UV filters or others

Preparation problems caused by the interaction of individual Preparation components arise among one another, as crystallization processes, precipitations and agglomerate formation are avoided, since the interaction is prevented.

It is therefore preferred according to the invention if one or more of the above-mentioned UV filters are in encapsulated form. It is advantageous if the capsules are so small that they cannot be observed with the naked eye. To achieve the above Effects, it is also necessary that the capsules are sufficiently stable and do not release the encapsulated active ingredient (UV filter) into the environment or only to a small extent.

Suitable capsules can have walls made of inorganic or organic polymers. For example, US 6,242,099 B1 describes the production of suitable capsules with walls made of chitin, chitin derivatives or polyhydroxylated polyamines. Capsules to be used particularly preferably according to the invention have walls which can be obtained by a SolGel process, as described in the applications WO 00/09652, WO 00/72806 and WO 00/71084. Capsules, the walls of which are made of silica gel (silica;

Undefined silicon oxide hydroxide) are built up. The production of corresponding capsules is known to the person skilled in the art, for example from the cited patent applications, the content of which expressly belongs to the subject of the present application.

The capsules in the preparations according to the invention are preferably present in amounts which ensure that the encapsulated UV filters are present in the preparation in the amounts indicated above.

The protective effect of preparations according to the invention against oxidative stress or against the action of radicals can therefore be further improved if the preparations contain one or more antioxidants, the person skilled in the art having no difficulty with suitably acting quickly or with a delay

Select antioxidants. In a preferred embodiment of the present invention, the preparation is therefore a preparation for protecting body cells against oxidative stress, in particular for reducing skin aging, characterized in that it contains one or more antioxidants in addition to the one or more compounds of the formula I. ,

There are many well-known and proven substances known from the literature that can be used as antioxidants, e.g. Amino acids (e.g.

Glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (e.g. urocanic acid) and their derivatives, peptides such as D, L-carnosine, D-carnosine, L-carnosine and their derivatives (e.g. anserine), carotenoids, carotenes (e.g. α-carotene, ß-carotene, lycopene) and their derivatives, chlorogenic acid and their derivatives, lipoic acid and their derivatives (e.g.

Dihydrolipoic acid), aurothioglucose, propylthiouracil and other thiols (e.g. thioredoxin, glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, , Oleyl, γ-linoleyl, cholesteryl and glyceryl esters) as well as their salts, dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (e.g. buthioninsulfonine sulfoximine, homocystone sulfoximine, homocystone sulfonimine, homocystone sulfone imine, homocystone sulfone imine, homocystone sulfone imine, homocystone sulfone imine, homocystone sulfonimine sulfone, Penta-, hexa-, heptathionin-sulfoximine) in very low tolerable doses (e.g. pmol to μmol / kg), also (metal) chelators ((e.g. α-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), α-hydroxy acids ( eg citric acid, lactic acid, malic acid), humic acid, bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives, vitamin C and derivative ate (e.g. ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl acetate), tocopherols and derivatives

(e.g. vitamin E acetate), vitamin A and derivatives (e.g. vitamin A palmitate) as well as coniferyl benzoate of benzoin, rutinic acid and its derivatives, α-glycosylrutin, ferulic acid, furfurylidene glucitol, carnosine, butylated hydroxytoluene, butylated hydroxyanisole, nordohydrogonuarybutaric acid, trihydroxy hydroxybutaryl acid , Quercitin, uric acid and its derivatives, mannose and its derivatives, zinc and its derivatives (eg ZnO, ZnSθ ₄ ), selenium and its derivatives (eg selenium methionine), stilbenes and their derivatives (eg stilbene oxide, trans-stilbene oxide).

Mixtures of antioxidants are also suitable for use in the cosmetic preparations according to the invention. Known and commercially available mixtures are, for example, mixtures containing lecithin, L - (+) - ascorbyl palmitate and citric acid (for example (eg Oxynex ^® AP), natural tocopherols, L - (+) - ascorbyl palmitate, L - (+) - ascorbic acid and Citric acid (e.g. Oxynex ^® K LIQUID), tocopherol extracts from natural sources, L - (+) - ascorbyl palmitate, L - (+) - ascorbic acid and citric acid (e.g. Oxynex ^® L LIQUID), DL-α-tocopherol, L - (+) - Ascorbyl palmitate, citric acid and lecithin (eg Oxynex ^® LM) or butylated hydroxytoluene (BHT), L - (+) - ascorbyl palmitate and citric acid (eg Oxynex ^® 2004). Such antioxidants are usually used with compounds of formula I in such compositions in ratios in the range from 1000: 1 to 1: 1000, preferably in amounts from 100: 1 to 1: 100.

The preparations according to the invention can contain vitamins as further ingredients. Vitamins and vitamin derivatives are preferably selected from vitamin A, vitamin A propionate, vitamin A palmitate, vitamin A acetate, retinol, vitamin B, thiamin chloride hydrochloride (vitamin Bi), riboflavin (vitamin B ₂ ), nicotinic acid amide, Vitamin C (ascorbic acid), vitamin D, ergocalciferol (vitamin D ₂ ), vitamin E, DL-α-tocopherol, tocopherol E-acetate, tocopherol hydrogen succinate, vitamin K-ι, esculin

(Vitamin P active ingredient), thiamine (vitamin Bi), nicotinic acid (niacin), pyridoxin, pyridoxal, pyridoxamine, (vitamin BQ), pantothenic acid, biotin, folic acid and cobalamin (vitamin B ₁₂ ) in the cosmetic preparations according to the invention contain, particularly preferably vitamin A palmitate, vitamin C and its derivatives, DL-α-tocopherol,

Tocopherol E acetate, nicotinic acid, pantothenic acid and biotin. Vitamins are usually used with compounds of the formula I in ratios in the range from 1000: 1 to 1: 1000, preferably in amounts from 100: 1 to 1: 100. Among the phenols with an antioxidative effect, the polyphenols, some of which occur as natural substances, are particularly interesting for applications in the pharmaceutical, cosmetic or nutritional field. For example, the flavonoids or bioflavonoids, which are mainly known as plant dyes, often have an antioxidant potential. K. Lemanska, H. Szymusiak, B. Tyrakowska, R. Zielinski, IMCM Rietjens deal with effects of the substitution pattern of mono- and dihydoxyflavones; Current Topics in Biophysics 2000, 24 (2), 101-108. It is observed there that dihydroxyflavones with an OH group adjacent to the keto function or OH groups in the 3'4'- or 6.7- or 7.8-position have antioxidative properties, while other mono- and dihydroxyflavones sometimes have no antioxidative properties exhibit.

Quercetin (cyanidanol, cyanidenolone 1522, meletin, sophoretin, ericin, 3,3 ', 4', 5,7-pentahydroxyflavon) is frequently mentioned as a particularly effective antioxidant (e.g. CA. Rice-Evans, NJ Miller, G. Paganga, Trends in Plant Science 1997, 2 (4), 152-159). K. Lemanska, H. Szymusiak, B. Tyrakowska, R. Zielinski, A.E.M.F. Soffers, I.M.C.M. Rietjens; Free Radical Biology & Medicine 2001, 31 (7), 869-881 investigate the pH dependence of the antioxidant effect of hydroxyflavones. Quercetin shows the highest activity of the examined structures over the entire pH range.

Suitable antioxidants are also compounds of the formula V.

wherein R ¹ to R ^{10 may be the} same or different and are selected from - H - OR ¹¹ - straight-chain or branched d- to C ₂ o -alkyl groups, - straight-chain or branched C ₃ - to C ₂ o-alkenyl groups, - straight-chain or branched d- to C ₂ o-hydroxyalkyl groups, the hydroxy group being attached to a primary or secondary carbon atom of the chain can be bound and further the alkyl chain can also be interrupted by oxygen, and / or - C ₃ - to Cio-cycloalkyl groups and / or C ₃ - to d ₂ - cycloalkenyl groups, the rings also each by - (CH ₂ ) _n - groups with n = 1 to 3 can be bridged, where all OR ¹¹ independently of one another stand for - OH - straight-chain or branched d- to C ₂ o-alkyloxy groups, - straight-chain or branched C ₃ - to C ₂ o- alkenyloxy groups, - straight-chain or branched Cr to C ₂ o- hydroxyalkoxy groups, where the hydroxy group (s) can be bonded to a primary or secondary carbon atoms of the chain and the alkyl chain can also be interrupted by oxygen nn, and / or - C ₃ - to Cio-cycloalkyloxy groups and / or C ₃ - to d ₂ - cycloalkenyloxy groups, where the rings can also be bridged by - (CH ₂ ) _n groups with n = 1 to 3 and / or, - mono- and / or oligoglycosyl radicals, with the proviso that at least 4 radicals from R to R ⁷ stand for OH and that there are at least 2 pairs of adjacent groups -OH in the molecule, - or R ² , R ⁵ and R ⁶ for OH and the radicals R ¹ , R ³ , R ⁴ and R ^7-10 stand for H, as described in the older German patent application DE 10244282.7. Advantages of the compositions according to the invention containing at least one antioxidant are, in addition to the advantages mentioned above, in particular the antioxidant action and the good skin tolerance. In addition, preferred of the compounds described here are colorless or only slightly colored and thus do not lead to discoloration of the preparations or only to a minor extent. Of particular advantage is the particular action profile of the compounds of formula V, which in the DPPH assay in a high capacity radicals catch (EC ₅ o), a delayed action (TECSO 120 min) and thus a medium to high anti-radical efficiency (AE ) expresses. In addition, the compounds according to formula V combine antioxidative properties in the molecule with UV absorption in the UV-A and / or -B range. Preparations containing at least one compound of the formula V, which is characterized in that at least two adjacent radicals of the radicals R ¹ to R ⁴ are OH and at least two adjacent radicals of the radicals R ⁵ to R ⁷ are OH, are therefore also preferred. Particularly preferred preparations contain at least one compound of the formula V, which is characterized in that at least three adjacent radicals of the radicals R ¹ to R ⁴ are OH, the radicals R ¹ to R ³ preferably being OH.

The preparations according to the invention can also contain other customary skin-protecting or skin-care active ingredients. In principle, these can be all active ingredients known to the person skilled in the art.

Particularly preferred active ingredients are, for example, so-called compatible solutes. These are substances that are involved in the osmoregulation of plants or microorganisms and can be isolated from these organisms. Compatible solutes are also included in the German

Patent application DE-A-10133202 described described Osmolyte. Suitable osmolytes are, for example, the polyols, methylamine compounds and amino acids and their respective precursors. In the sense of German patent application DE-A-10133202, osmolytes are in particular substances from the group of the polyols, such as, for example, myo-inositol, mannitol or sorbitol and / or one or understood several of the osmolytically active substances mentioned below:

Taurine, choline, betaine, phosphorylcholine, glycerophosphorylcholines, glutamine, glycine, α-alanine, glutamate, aspartate, proline, and taurine. Precursors of these substances are, for example, glucose, glucose polymers,

Phosphatidylcholine, phosphatidylinositol, inorganic phosphates, proteins, peptides and polyamic acids. Precursors are e.g. B. Compounds that are converted to osmolytes by metabolic steps.

According to the invention, compatible solutes are preferably selected from the group consisting of pyrimidinecarboxylic acids (such as ectoin and hydroxyectoin), proline, betaine, glutamine, cyclic diphosphoglycerate, N.-acetylornithine, trimethylamine-N-oxide di-myo-inositol-phosphate (DIP) , cyclic 2,3-diphosphoglycerate (cDPG), 1,1-diglycerol phosphate (DGP), ß-mannosylglycerate (Firoin), ß-

Mannosylglyceramide (Firoin-A) or / and di-mannosyl-di-inositol phosphate (DMIP) or an optical isomer, derivative, e.g. an acid, a salt or ester of these compounds or combinations thereof.

Among the pyrimidinecarboxylic acids, ectoin ((S) -

1, 4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid) and hydroxyectoin ((S, S) -1, 4,5,6-tetrahydro-5-hydroxy-2-methyl-4-pyrimidinecarboxylic acid and their These compounds stabilize enzymes and other biomolecules in aqueous solutions and organic solvents, and in particular they stabilize enzymes against denaturing conditions such as salts, extreme pH values, surfactants, urea, guanidinium chloride and other compounds.

Ectoin and ectoin derivatives such as hydroxyectoin can advantageously be used in medicinal products. In particular, hydroxyectoin can be used for

Manufacturing a drug used to treat skin disorders. Other areas of application of hydroxyectoin and other ectoin derivatives are typically in areas such as Trehalose is used as an additive. Ectoin derivatives such as hydroxyectoin can be used as a protective substance in dried yeast and bacterial cells. Pharmaceutical products such as non-glycosylated, pharmaceutically active peptides and proteins, for example t-PA, can also be protected with ectoin or its derivatives.

Cosmetic applications include in particular the use of ectoin and ectoin derivatives for the care of aged, dry or irritated skin. For example, European patent application EP-A-0 671 161 describes in particular that ectoin and hydroxyectoin are used in cosmetic preparations such as powders, soaps, surfactant-containing cleaning products, lipsticks, blushes, make-ups, skin care creams and sunscreen preparations.

A pyrimidine carboxylic acid according to formula VI below is preferably used,

wherein R ^{1 is} H or CI-8 alkyl, R ^{2 is} H or C1 -4 alkyl and R ³ ,

R ⁴ , R ⁵ and R ^{6 are} each independently a radical from the group H, OH, NH ₂ and C1-4-alkyl. Pyrimidinecarboxylic acids in which R ^{2 is} a methyl or an ethyl group and R ¹ or R ⁵ and R ^{6 are} H are preferably used. The pyrimidinecarboxylic acids ectoin ((S) -1, 4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid) and hydroxyectoin ((S, S) -1, 4,5, 6-tetrahydro-5-hydroxy-2-methyl-4-pyrimidine-carboxylic acid) used. The preparations according to the invention preferably contain pyrimidinecarboxylic acids of this type in amounts of up to 15% by weight. Preferably the pyrimidine carboxylic acids are used in ratios of 100: 1 to 1: 100 to the compounds of formula I, ratios in the range 1:10 to 10: 1 being particularly preferred.

It is particularly preferred according to the invention if the compatible solutes are selected from di-myo-inositol phosphate (DIP), cyclic 2,3-diphosphoglycerate (cDPG), 1,1-diglycerol phosphate (DGP), β-mannosylglycerate ( Firoin), β-mannosylglyceramide (Firoin-A) and / or dimannosyl-di-inositol phosphate (DMIP), ectoin, hydroxyectoin or mixtures thereof.

All compounds or components that can be used in the preparations are either known and commercially available or can be synthesized by known methods.

The one or more compounds of the formula I can be incorporated into cosmetic or dermatological preparations in the customary manner. Preparations are suitable for external use, for example as a cream, lotion, gel, or as a solution which can be sprayed onto the skin. Dosage formulas such as capsules, coated tablets, powders, tablet solutions or solutions are suitable for internal use.

As a form of application of the preparations according to the invention, e.g. called: solutions, suspensions, emulsions, PIT emulsions, pastes,

Ointments, gels, creams, lotions, powders, soaps, tenside-containing cleaning preparations, oils, aerosols and sprays. Other forms of application are e.g. Sticks, shampoos and shower baths. Any customary carriers, auxiliaries and, if appropriate, further active ingredients can be added to the preparation.

Preferred auxiliaries come from the group of preservatives, antioxidants, stabilizers, solubilizers, vitamins, colorants, odor improvers. Ointments, pastes, creams and gels can contain the usual carriers, for example animal and vegetable fats, waxes, paraffins, starch, tragacanth, cellulose derivatives, polyethylene glycols, silicones, bentonites, silica, talc and zinc oxide or mixtures of these substances.

Powders and sprays can contain the usual carriers, e.g. Milk sugar, talc, silica, aluminum hydroxide, calcium silicate and polyamide powder or mixtures of these substances. Sprays can also contain the usual propellants, e.g. Chlorofluorocarbons, propane / butane or dimethyl ether.

Solutions and emulsions can contain the usual carriers such as solvents, solubilizers and emulsifiers, e.g. Water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1, 3-butyl glycol, oils, especially cottonseed oil,

Contain peanut oil, corn oil, olive oil, castor oil and sesame oil, glycerin fatty acid esters, polyethylene glycols and fatty acid esters of sorbitan or mixtures of these substances.

Suspensions can be the usual carriers such as liquid diluents, e.g. Water, ethanol or propylene glycol, suspending agents e.g. ethoxylated isostearyl alcohols, polyoxyethylene sorbitol esters and polyoxyethylene sorbitan esters, microcrystalline cellulose, aluminum metahydroxide, bentonite, agar agar and tragacanth or mixtures of these substances.

Soaps can contain the usual carriers such as alkali salts of fatty acids, salts of fatty acid half-esters, fatty acid protein hydrolyzates, isothionates, lanolin, fatty alcohol, vegetable oils, plant extracts, glycerol, sugar or mixtures of these substances.

Surfactant-containing cleaning products can contain the usual carriers such as salts of fatty alcohol sulfates, fatty alcohol ether sulfates, sulfobemstein acid half-esters, fatty acid protein hydrolyzates, isothionates, imidazolinium derivatives, methyl taurates, sarcosinates, fatty acid amide ether sulfates, alkyl amidobetaine, fatty acid fatty alcohols, fatty alcohol amides contain vegetable and synthetic oils, lanolin derivatives, ethoxylated glycerol fatty acid esters or mixtures of these substances.

Facial and body oils can contain the usual carriers such as synthetic oils such as fatty acid esters, fatty alcohols, silicone oils, natural

Contain oils such as vegetable oils and oily plant extracts, paraffin oils, lanolin oils or mixtures of these substances.

Other typical cosmetic forms of use are also lipsticks, lip care sticks, mascara, eyeliner, eye shadows, blush, powder,

Emulsion and wax make-up as well as sun protection, pre-sun and after-sun preparations.

The preferred preparation forms according to the invention include in particular emulsions.

Emulsions according to the invention are advantageous and contain z. B. said fats, oils, waxes and other fat bodies, as well as water and an emulsifier, as is usually used for such a type of preparation.

The lipid phase can advantageously be selected from the following group of substances:

- mineral oils, mineral waxes

- Oils, such as triglycerides of capric or caprylic acid, as well as natural oils such. B. castor oil;

Fats, waxes and other natural and synthetic fat bodies, preferably esters of fatty acids with alcohols of low C number, e.g. with isopropanol, propylene glycol or glycerin, or esters of fatty alcohols with low C number alkanoic acids or with fatty acids;

- Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiloxanes and mixed forms thereof.

The oil phase of the emulsions, oleogels or hydrodispersions or

Lipodispersions for the purposes of the present invention are advantageous selected from the group of esters of saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 3 to 30 C atoms and saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 3 to 30 C atoms , from the group of esters of aromatic carboxylic acid and saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 3 to 30 carbon atoms. Such ester oils can then advantageously be selected from the group of isopropyl myristate, isopropyl palmitate, isopropyl stearate, isopropyl oleate, n-butyl stearate, n-hexyl laurate, n-decyl oleate, isooctyl stearate, isononyl stearate, isononylisononanoate, 2-ethylhexyl stylate, 2-ethylhexyl stylate, 2-octyldodecyl palmitate, oleyl oleate, olerlerucate, erucyl oleate, erucylerucate and synthetic, semisynthetic and natural mixtures of such esters, e.g. B. Jojoba oil.

Furthermore, the oil phase can advantageously be chosen from the group of branched and unbranched hydrocarbons and waxes, silicone oils, dialkyl ethers, the group of saturated or unsaturated, branched or unbranched alcohols, and also fatty acid triglycerides, especially the triglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 8 to 24, in particular 12-18, carbon atoms. The fatty acid triglycerides can for example be advantageously selected from the group of synthetic, semi-synthetic and natural oils, e.g. B. olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palm oil, coconut oil,

Palm kem oil and the like.

Any mixtures of such oil and wax components can also be used advantageously for the purposes of the present invention. It may also be advantageous to use waxes, for example cetyl palmitate, as the sole lipid component of the oil phase.

The oil phase is advantageously selected from the group 2-ethylhexyl isostearate, octyldodecanol, isotridecyl isononanoate, isoeicosane, 2-ethylhexyl cocoate, C ₂ -i ₅ -alkyl benzoate, caprylic capric acid triglyceride, dicapryl ether. Particularly advantageous are mixtures of C ^ - _C15 alkyl benzoate and 2-ethylhexyl isostearate, mixtures of Cι ₂ -i ₅ alkyl benzoate and isotridecyl isononanoate and mixtures of C ₂ -i ₅ alkyl benzoate, 2-ethylhexyl isostearate and isotridecyl isononanoate.

Of the hydrocarbons, paraffin oil, squalane and squalene can be used advantageously for the purposes of the present invention.

The oil phase can also advantageously have a cyclic or linear silicone oil content or consist entirely of such oils, although it is preferred to use an additional content of other oil phase components in addition to the silicone oil or the silicone oils.

Cyclomethicone (octamethylcyclotetrasiloxane) is advantageously used as the silicone oil to be used according to the invention. However, other silicone oils can also be used advantageously for the purposes of the present invention, for example hexamethylcyclotrisiloxane, polydimethylsiloxane, poly (methylphenylsiloxane).

Mixtures of cyclomethicone and isotridecyl isononanoate, cyclomethicone and 2-ethylhexyl isostearate are also particularly advantageous.

The aqueous phase of the preparations according to the invention advantageously advantageously contains alcohols, diols or polyols of low C number, and also their ethers, preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether, diethylene - Glycol monomethyl or monoethyl ether and analog products, furthermore

Low C number alcohols, e.g. B. ethanol, isopropanol, 1, 2-propanediol, glycerol and in particular one or more thickeners, which or which can advantageously be selected from the group consisting of silicon dioxide, aluminum silicates, polysaccharides or their derivatives, for example hyaluronic acid, xanthan gum, hydroxypropylmethyl cellulose, particularly advantageously the group of polyacrylates, preferably a polyacrylate the group of so-called carbopoles, for example carbopoles of types 980, 981, 1382, 2984, 5984, each individually or in combination.

Mixtures of the abovementioned solvents are used in particular. Water can also be a component of alcoholic solvents.

Emulsions according to the invention are advantageous and contain z. B. said fats, oils, waxes and other fat bodies, as well as water and an emulsifier, as is usually used for such a type of formulation.

In a preferred embodiment, the preparations according to the invention contain hydrophilic surfactants.

The hydrophilic surfactants are preferably selected from the group of alkyl glucosides, acyl lactylates, betaines and cocoamphoacetate.

The alkyl glucosides are in turn advantageously selected from the group of alkyl glucosides, which are characterized by the structural formula

distinguish, where R is a branched or unbranched alkyl radical having 4 to 24 carbon atoms and where DP is an average degree of glucosylation of up to 2. The value DP represents the degree of glucosidation of the alkyl glucosides used according to the invention and is defined as DP = 1 + 2 + 3 + ... - ∑ / 100 100 100 100

Here, p-ι, p ₂ , p ₃ ... and pι represent the proportion of single, double, triple ... i-fold glucosylated products in weight percent. Products with degrees of glucosylation of 1-2, in particular, are advantageous according to the invention advantageously chosen from 1.1 to 1.5, very particularly advantageously from 1.2-1.4, in particular from 1.3.

The value DP takes account of the fact that alkylglucosides are generally mixtures of mono- and oligoglucosides due to their production. A relatively high content of monoglucosides, typically of the order of 40-70% by weight, is advantageous according to the invention.

Alkylglylcosides which are used particularly advantageously according to the invention are selected from the group consisting of octylglucopyranoside, nonylglucopyranoside, decylglucopyranoside, undecylglucopyranoside, dodecylglucopyranoside, tetrahedronylglucopyranoside and hexadecylglucopyranoside.

It is likewise advantageous to employ natural or synthetic raw materials and assistants or mixtures which are distinguished by an effective content of the active ingredients used according to the invention, for example Plantaren ^® 1200 (Henkel KGaA), Oramix NS ^® 10 (Seppic).

The acyl lactylates are in turn advantageously selected from the group of

Substances that are characterized by the structural formula

O O M *

distinguish, wherein R ^{1 is} a branched or unbranched alkyl radical having 1 to 30 carbon atoms and M ^{+ is selected} from the group of alkali ions and the group of ammonium ions substituted with one or more alkyl and / or with one or more hydroxyalkyl radicals or half Equivalent to an alkaline earth ion.

Sodium isostearyl lactylate, for example that, is advantageous

PPrroodduukktt F Pathionic ^® ISL from American Ingredients

Company.

The betaines are advantageously selected from the group of substances which are distinguished by the structural formula

distinguish, wherein R ^{2 is} a branched or undisclosed alkyl radical having 1 to 30 carbon atoms.

R ² particularly advantageously denotes a branched or unbranched alkyl radical having 6 to 12 carbon atoms.

Capramidopropylbetaine, for example the product Tego ^® Betaine is advantageous, for example 810 from Th. Goldschmidt AG. , Sodium, for example, selected as inventively advantageous cocoamphoacetate as under the name Miranol ^® Ultra C32 from Miranol Chemical Corp. is available.

The preparations according to the invention are advantageously characterized in that the hydrophilic surfactant or surfactants in concentrations of 0.01-20% by weight, preferably 0.05-10% by weight, particularly preferably 0.1-5% by weight, in each case based on the total weight of the composition, is or are present.

For use, the cosmetic and dermatological preparations according to the invention are applied to the skin and / or the hair in a sufficient amount in the manner customary for cosmetics.

Cosmetic and dermatological preparations according to the invention can be in various forms. So you can z. B. a solution, an anhydrous preparation, an emulsion or microemulsion of the water-in-oil (W / O) or oil-in-water (O / W) type, a multiple emulsion, for example of the Waser-in type Oil-in-water (W / O / W), a gel, a solid stick, an ointment or an aerosol. It is also advantageous to give ectoine in an encapsulated form, e.g. B. in collagen matrices and other common encapsulation materials, e.g. B. as cellulose encapsulations, encapsulated in gelatin, wax matrices or liposomal. In particular, wax matrices as described in DE-OS 43 08 282 have been found to be favorable. Emulsions are preferred. O / W emulsines are particularly preferred. Emulsions, W / O emulsions and O / W emulsions are available in the usual way.

The known W / O and O / W

Emulsifiers are used. It is advantageous to use other customary co-emulsifiers in the preferred O / W emulsions according to the invention.

According to the invention, they are advantageous as co-emulsifiers, for example

O / W emulsifiers selected, mainly from the group of substances with HLB values of 11-16, very particularly advantageously with HLB values of 14.5-15.5, provided the O / W emulsifiers have saturated radicals R and R '. If the O / W emulsifiers have unsaturated radicals R and / or R ', or if isoalkyl derivatives are present, the preferred HLB value of such emulsifiers can also be lower or higher.

It is advantageous to choose the fatty alcohol ethoxylates from the group of the ethoxylated stearyl alcohols, cetyl alcohols, cetylstearyl alcohols (cetearyl alcohols). Particularly preferred are: polyethylene glycol (13) stearyl ether (steareth-13), polyethylene glycol (14) stearyl ether

(Steareth-14), polyethylene glycol (15) stearyl ether (Steareth-15),

Polyethylene glycol (16) stearyl ether (Steareth-16), polyethylene glycol (17) - stearyl ether (Steareth-17), polyethylene glycol (18) stearyl ether (Steareth-18), polyethylene glycol (19) stearyl ether (Steareth-19), polyethylene glycol (20) - stearyl ether (Steareth-20), polyethylene glycol (12) isostearyl ether

(isosteareth-12), polyethylene glycol (13) isostearyl ether (isosteareth-13), polyethylene glycol (14) isostearyl ether (isosteareth-14), polyethylene glycol (15) isostearyl ether (isosteareth-15), polyethylene glycol (16) - isostearyl ether (isosteareth- 16), polyethylene glycol (17) isostearyl ether (isosteareth-17), polyethylene glycol (18) isostearyl ether (isosteareth-18),

Polyethylene glycol (19) isostearyl ether (isosteareth-19), polyethylene glycol (20) isostearyl ether (isosteareth-20), polyethylene glycol (13) cetyl ether (ceteth-13), polyethylene glycol (14) cetyl ether (ceteth-14), polyethylene glycol ( 15) cetyl ether (ceteth-15), polyethylene glycol (16) cetyl ether (ceteth-16), polyethylene glycol (17) cetyl ether (ceteth-17), polyethylene glycol (18) - cetyl ether (ceteth-18), polyethylene glycol (19) cetyl ether (ceteth -19), polyethylene glycol (20) cetyl ether (ceteth-20), polyethylene glycol (13) isocetyl ether (isoceteth-13), polyethylene glycol (14) isocetyl ether (isoceteth-14), polyethylene glycol (15) isocetyl ether (isoceteth-15 ), Polyethylene glycol (16) isocetyl ether (isoceteth-16), polyethylene glycol (17) - isocetyl ether (isoceteth-17), polyethylene glycol (18) isocetyl ether (isoceteth-18), polyethylene glycol (19) isocetyl ether (isoceteth-19), polyethylene glycol (20) isocetyl ether (isoceteth-20), polyethylene glycol (12) oleyl ether (oleth-12), polyethylene glycol (13) oleyl ether (oleth-13), polyethylene glycol (14) oleyl ether (Oleth-14), polyethylene glycol (15) oleyl ether (Oleth-15),

Polyethylene glycol (12) lauryl ether (Laureth-12), polyethylene glycol (12) - isolauryl ether (isolaureth-12), polyethylene glycol (13) cetyl stearyl ether (ceteareth-13), polyethylene glycol (14) cetyl stearyl ether (ceteareth-14), polyethylene glycol (15) cetyl stearyl ether (ceteareth-15), polyethylene glycol (16) cetyl stearyl ether 16), polyethylene glycol (17) - cetyl stearyl ether (ceteareth-17), polyethylene glycol (18) cetyl stearyl ether

(Ceteareth-18), polyethylene glycol (19) cetyl stearyl ether (Ceteareth-19), polyethylene glycol (20) cetyl stearyl ether (Ceteareth-20).

It is also advantageous to choose the fatty acid ethoxylates from the following group:

Polyethylene glycol (20) stearate, polyethylene glycol (21) stearate, polyethylene glycol (22) stearate, polyethylene glycol (23) stearate, polyethylene glycol (24) stearate, polyethylene glycol (25) stearate, polyethylene glycol (12) isostearate, polyethylene glycol (13) isostearate, polyethylene glycol ( 14) isostearate, polyethylene glycol (15) isostearate,

Polyethylene glycol (16) isostearate, polyethylene glycol (17) isostearate, polyethylene glycol (18) isostearate, polyethylene glycol (19) isostearate, polyethylene glycol (20) isostearate, polyethylene glycol (21) isostearate, polyethylene glycol (22) isostearate, polyethylene glycol (23) isostearate, polyethylene 24) isostearate, polyethylene glycol (25) isostearate,

Polyethylene glycol (12) oleate, Polyethylene glycol (13) oleate, Polyethylene glycol (14) oleate, Polyethylene glycol (15) oleate, Polyethylene glycol (16) oleate, Polyethylene glycol (17) oleate, Polyethylene glycol (18) oleate, Polyethylene glycol (19) oleate, Polyethylene glycol ( 20) oleate,

Sodium laureth-11 carboxylate can advantageously be used as the ethoxylated alkyl ether carboxylic acid or its salt. Sodium laureth 1-4 sulfate can advantageously be used as the alkyl ether sulfate. Polyethylene glycol (30) cholesteryl ether can advantageously be used as the ethoxylated cholesterol derivative. Polyethylene glycol (25) soyasterol has also proven itself. Polyethylene glycol (60) evening primrose glycerides can advantageously be used as ethoxylated triglycerides (evening primrose = evening primrose). It is also advantageous to use the polyethylene glycol glycerol fatty acid esters from the group polyethylene glycol (20) glyceryl laurate, polyethylene glycol (21) glyceryl laurate, polyethylene glycol (22) glyceryl laurate, polyethylene glycol (23) glyceryl laurate, polyethylene glycol (6) glyceryl caprate / cprinate (20) ) glyceryl oleate, polyethylene glycol (20) glyceryl isostearate, polyethylene glycol (18) glyceryl oleate (cocoat).

It is also advantageous to choose the sorbitan esters from the group consisting of polyethylene glycol (20) sorbitan monolaurate, polyethylene glycol (20) sorbitan monostearate, polyethylene glycol (20) sorbitan monoisostearate, polyethylene glycol (20) sorbitan monopalmitate, polyethylene glycol (20) sorbitan monooleate.

The following optional W / O emulsifiers can be used:

Fatty alcohols with 8 to 30 carbon atoms, monoglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 8 to 24, in particular 12-18 C atoms, diglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 8 to 24, in particular 12-18 C atoms, monoglycerol ethers of saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 8 to 24, in particular 12-18 C atoms, diglycerol ether of saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 8 to 24, in particular 12-18, carbon atoms,

Propylene glycol esters of saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 8 to 24, in particular 12-18 C atoms, and sorbitan esters of saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 8 to 24, especially 12-18 carbon atoms.

Particularly advantageous W / O emulsifiers are glyceryl monostearate, glyceryl monoisostearate, glyceryl monomyristate, glyceryl monooleate, diglyceryl monostearate, diglyceryl monoisostearate, propylene glycol monostearate, propylene glycol monoisostearate, propylene glycol monocaprylate,

Propylene glycol monolaurate, sorbitan monoisostearate, sorbitan monolaurate, Sorbitan monocaprylate, sorbitan monoisooleate, sucrose distearate, cetyl alcohol, stearyl alcohol, arachidyl alcohol, behenyl alcohol, isobehenyl alcohol, selachyl alcohol, chimyl alcohol, polyethyleneglycol (2) stearyl ether (steareth-2), glyceryl mono- glyceryl monylurate.

Preparations preferred according to the invention are particularly suitable for protecting human skin against aging processes and against oxidative stress, i.e. against damage by radicals, such as e.g. generated by solar radiation, heat or other influences. It is available in various dosage forms commonly used for this application. It can be used in particular as a lotion or emulsion, such as a cream or milk (O / W, W / O, O / W / O, W / O / W), in the form of oily-alcoholic, oily-aqueous or aqueous-alcoholic gels or solutions, as solid pins or as

Be made up aerosol.

The preparation may contain cosmetic adjuvants which are commonly used in this type of preparation, e.g. Thickeners, plasticizers, wetting agents, surfactants, emulsifiers, preservatives, anti-foaming agents, perfumes, waxes, lanolin, blowing agents, dyes and / or pigments which color the agent itself or the skin, and other ingredients commonly used in cosmetics.

An oil, wax or other fatty substance, a low monoalcohol or a low polyol or mixtures thereof can be used as the dispersing or solubilizing agent. The particularly preferred monoalcohols or polyols include ethanol, i-propanol, propylene glycol, glycerin and sorbitol.

A preferred embodiment of the invention is an emulsion which is present as a protective cream or milk and, in addition to the compound (s) of the formula I, for example fatty alcohols, fatty acids, fatty acid esters, in particular triglycerides of fatty acids, lanolin, natural and contains synthetic oils or waxes and emulsifiers in the presence of water.

Further preferred embodiments are oily lotions based on natural or synthetic oils and waxes, lanolin,

Fatty acid esters, in particular triglycerides of fatty acids, or oil-alcoholic lotions based on a lower alcohol, such as ethanol, or a glycerol, such as propylene glycol, and / or a polyol, such as glycerol, and oils, waxes and fatty acid esters, such as triglycerides of fatty acids.

The preparation according to the invention can also be in the form of an alcoholic gel which comprises one or more lower alcohols or polyols, such as ethanol, propylene glycol or glycerol, and a thickener, such as silica. The oily-alcoholic gels also contain natural or synthetic oil or wax.

The solid sticks consist of natural or synthetic waxes and oils, fatty alcohols, fatty acids, fatty acid esters, lanolin and other fatty substances.

If a preparation is packaged as an aerosol, the usual propellants, such as alkanes, fluoroalkanes and chlorofluoroalkanes, are generally used.

The cosmetic preparation can also be used to protect the hair against photochemical damage, to prevent changes in color shades, discoloration or damage of a mechanical nature. In this case, it is suitably packaged as a shampoo, lotion, gel or emulsion for rinsing, the respective

Preparation is applied before or after shampooing, before or after dyeing or decoloring or before or after the perm. A preparation can also be selected as a lotion or gel for styling and treatment, as a lotion or gel for brushing or laying a water wave, as a hair lacquer, permanent wave agent, dye or bleaching agent for the hair. The preparation with light protection properties In addition to the compound or compounds of the formula I, it may contain various adjuvants used in this type of agent, such as interfaces, active agents, thickeners, polymers, plasticizers, preservatives, foam stabilizers, electrolytes, organic solvents, silicone derivatives, oils, waxes, anti-greasing agents, dyes and / or pigments that color the composition itself or the hair or other ingredients commonly used for hair care.

The present invention furthermore relates to a process for the preparation of a preparation, which is characterized in that at least one compound of the formula I is mixed with residues as described above with a cosmetically or dermatologically or for food-compatible carrier, and the use of a compound of the formula I for the preparation of a preparation with antioxidant properties.

The preparations according to the invention can be produced using techniques which are well known to the person skilled in the art.

The mixing can be a dissolving, emulsifying or dispersing the

Result in compound of formula I in the carrier.

The invention is explained in more detail below with the aid of examples; the invention can be carried out in the entire claimed range and is not restricted to the examples mentioned here.

Examples

Example 1 Preparation of N-acetyl-N- (2-ethylhexyl) -3-aminopropanoic acid butyl ester

0.78 mol (100.2 g) of 2-ethyl-hexylamine are placed under nitrogen in a 1 L four-necked flask and cooled to ~ 0 ° C. in an ice bath. In about 30 minutes, 1.56 mol (202.1 g) of ethyl acrylate are added dropwise with stirring, the internal temperature not rising above 5 ° C. The clear, colorless reaction mixture is stirred for another hour. The reaction mixture is distilled in vacuo to separate unreacted ethyl acrylate and 2-ethylhexylamine. Yield: 191.6 g (88% content corrected) product (GC content ~ 93.0%)

0.69 mol (191 g) of 3- (2-ethyl-hexyl) aminopropanoic acid butyl ester are placed in a 500 ml four-necked flask under nitrogen and cooled to ~ 0 ° C. in an ice bath. 0.92 mol (93.9 g) of acetic anhydride are added dropwise in about 20 minutes. The reaction mixture warms to ~ 22 ° C until the addition is complete. To complete the reaction, the reaction mixture is heated to ~ 120 ° C. in an oil bath and stirred at this temperature for about 1 hour. The reaction solution is cooled, at ~ 75 ° C 0.22 mol (4 g) of water are added to hydrolyze the excess acetic anhydride. The mixture is stirred for a further hour with slow cooling. Then the standing acetic acid distilled off in vacuo. For further purification, the distillation residue is chromatographed neutral over 900 g of aluminum oxide using tert-butyl methyl ether. The product-containing fractions are combined and concentrated to the residue. The product is then degassed in a high vacuum. Yield: 148.0 g (72% content corrected) product (GC content ~ 99.9%)

The following compounds are prepared analogously from the correspondingly modified starting materials according to the principle described: N- (2-ethylhexoyl) -N- (2-ethylhexyl) -3-aminopropanoic acid ethyl ester,

- N- (2-ethylhexoyl) -N- (dodecyl) -3-aminopropanoic acid ethyl ester,

Butyl N-acetyl-N- (dodecyl) -3-aminopropanoate,

- butyl N- (2-ethylhexoyl) -N- (butyl) -3-aminopropanoate, - butyl N- (2-ethylhexoyl-N- (2-ethylhexyl) -3-aminopropanoate),

Butyl N- (2-ethylhexoyl) -N- (dodecyl) -3-aminopropane,

2-ethylhexyl N-acetyl-N- (butyl) -3-aminopropanoate,

N-acetyl-N- (2-ethylhexyl) -3-aminopropanoic acid 2-ethylhexyl ester,

- 2-ethylhexyl N-acetyl-N- (dodecyl) -3-aminopropanoate, - 2-ethylhexyl N- (2-ethylhexoyl) -N- (butyl) -3-aminopropanoate,

- N- (2-ethylhexoyl) -N- (2-ethylhexyl) -3-aminopropanoic acid 2-ethylhexyl ester,

- 2-ethylhexyl N- (2-ethylhexoyl) -N-dodecyl) -3-aminopropanoate.

Example 2: Liquid

Ingredient (INCI) [%]

A N-acetyl-N- (2-ethylhexyl) -3-aminopropanoic acid butyl ester 25

POLYSORBATE 80 0.20

ACRYLATES / C10-30 ALKYL ACRYLATE 0.20 CROSSPOLYMER

PERFUME q.s. B

Ethanol 96% 20.00

AQUA (WATER) ad 100

PROPYLENE GLYCOL 10.00 C SODIUM HYDROXIDE q.s.

production:

Phases A and B are mixed separately, phase A is added to phase B with stirring. The pH is adjusted and homogenized using phase C.

Example 3: O / W After Sun Lotion

Ingredient (INCI) [%]

A

N- (2-ethylhexoyl) -N- (2-ethylhexyl) -3-amino propanoic acid ethyl ester 10.00

BISABOLOL 0.30 CETEARYL ALCOHOL, CETEARYL 4.00

GLUCOSIDE

CAPRYLIC / CAPRIC TRIGLYCERIDE 2.00

CYCLOPENTASILOXANE 2.00

DIMETHICONE 1.00 B

AQUA (WATER) ad 100

GLYCERINE 3.00 Preservative qs

CITRIC ACID 0.07 DISODIUM PHOSPHATE 0.59 C XANTHAN GUM 0.50

production:

Phases A and B are heated separately to 75 ° C, phase C is slowly added to B and homogenized. A is then added to B / C at 75 ° C. and homogenized.

Example 4: aqueous gel

Ingredient (INCI) [%]

A

PROPYLENE GLYCOL 5.00

ALLANTOIN 0.20

AQUA (WATER) ad 100 B

CARBOMER 33.30

C

Triethanolamine 3.00

D N- (2-ethylhexoyl) -N- (2-ethylhexyl) -3-amino propanoic acid ethyl ester 10.00

production:

Phase A is heated to 75 ° C and slowly added to B. Then C is added to A / B and homogenized. Then D is added. Example 5: Spray

Ingredient (INCI) [% 1

A

N- (2-ethylhexoyl) -N- (dodecyl) -3-aminopropanoic acid ethyl ester 20.00

PEG-8 5.00

PPG-15 STEARYL ETHER 3.00

PERFUME 0.30

B

ALCOHOL 35.00

PEG-32 4.00

POLYSORBATE 20 1.50

AQUA (WATER) ad 100

production:

Phase B is slowly added to A and homogenized.

Example 6: Roll on

Ingredient (INCI) [%]

A

2-ethylhexyl N-acetyl-N- (butyl) -3-aminopropanoate 20.00

PEG-8 5.00

PPG-15 STEARYL ETHER 3.00

PERFUME 0.30

B

ALCOHOL 35.00

PEG-32 4.00

POLYSORBATE 20 1.50 CARBOMER 10.00

AQUA (WATER) ad 100

C

TRIETHANOLAMINE 0.30

production:

Phases A and B are mixed separately, phase B is added to phase A with stirring. The pH is adjusted using phase C and then homogenized.

Example 7: Cream

Ingredient (INCI) [%]

A

N-acetyl-N- (butyl) -3-aminopropanoic acid -2-ethylhexyl ester 20.00

CETEARYL ALCOHOL, CETEARYL GLUCOSIDE 4.00

CARBOMER 0.25

B

Preservatives q.s.

GLYCERINE 3.00

XANTHAN GUM 0.50

AQUA (WATER) ad 100

C

TRIETHANOLAMINE q.s.

production:

Phases A and B are heated to 70 ° C, A is slowly added to B.

The pH is adjusted using phase C and then homogenized.

Example 8: Cream Ingredient (INCI) [%]

A

2-ethylhexyl N-acetyl-N- (butyl) -3-aminopropanoate 20.00

CETEARYL ALCOHOL, CETEARYL GLUCOSIDE 4.00

CARBOMER 0.40

OLEYL ERUCATE 1.00

CYCLOPENTASILOXANE 1.00

DIBUTYL ADIPATE 1.00

ISOPROPYL PALMITATE 1.00

B

GLYCERINE 3.00

XANTHAN GUM 0.20

Preservatives q.s.

AQUA (WATER) ad 100

C

TRIETHANOLAMINE q.s.

Preparation: Phases A and B are heated to 70 ° C, A is slowly added to B.

The pH is adjusted using phase C and then homogenized.

Example 9: Camouflage color

Ingredient (INCI) [%] A

CI 77499 (IRON OXIDES), MICA 15.00

TALC 15.00 B

C18-36 ACID TRIGLYCERIDE 12.00 TRIBEHEN IN 3.00

CAPRYLIC / CAPRIC TRIGLYCERIDE 7.00

STEARIC ACID 3.00

PEG-8, TOCOPHEROL, ASCORBYL 0.10 PALMITATE, ASCORBIC ACID, CITRIC ACID

Preservatives q.s.

PPG-2 MYRISTYL ETHER PROPIONATE ad 100

2-ethylhexyl N-acetyl-N- (butyl) -3-aminopropanoate 20.00

production:

Phase A is mixed slowly added to phase B heated to 80 ° C.

Example 10: Sunscreen (SPF: 32)

Ingredient (INCI) [%]

A

N- (2-ethylhexoyl) -N- (butyl) -3-aminopropanoic acid-2-ethylhexyl ester 7.50 ETHYLHEXYL METHOXYCINNAMATE, BHT 7.50

OCTOCRYLENE 10.00

BUTYL METHOXYDIBENZOYLMETHANE 0.90

BENZOPHENONE-3 1.10

GLYCERYL STEARATE, PEG-100 STEARATE 3.20 COCO-GLUCOSIDE, COCONUT ALCOHOL 1.30

DIBUTYL ADIPATE 5.50

TOCOPHERYL ACETATE 0.25 B

LAURETH-7, POLYACRYLAMIDE, C13-14-ISOPARAFFIN 1.20 C

GLYCERIN 7.00 XANTHAN GUM 0.15

MAGNESIUM ALUMINUM SILICATE 0.60

DISODIUM EDTA 0.10

AQUA (WATER) ad 100

D

Preservatives q.s.

PERFUME 0.20

e

TROMETHAMINE q.s.

production:

All phases are prepared separately. Phase C: Xanthan gum and magnesium aluminum silicate are heated to 75-80 ° C and mixed with the other ingredients. Phase A is added to Phase C at 75 ° C. After homogenization, phase B is added at 60 ° C. To

Homogenize phase D is added at 40 ° C. Phase E is then added (pH = 6.5).

Example 11: Sunscreen (SPF: 43.6)

Ingredient (INCI) [%]

A

N- (2-Ethylhexoyl) -N- (butyl) -3-aminopropanoic acid 2-ethylhexyl ester 10.00 TOCOPHERYL ACETATE 0.25

ETHYLHEXYL METHOXYCINNAMATE, BHT 7.50

OCTOCRYLENE 10.00

BUTYL METHOXYDIBENZOYLMETHANE 0.90

BENZOPHENONE-3 1.10 GLYCERYL STEARATE, PEG-100 STEARATE 3.20

COCO-GLUCOSIDE, COCONUT ALCOHOL 1.30 DIBUTYL ADIPATE 3.00 B

LAURETH-7, POLYACRYLAMIDE, C13-14-ISOPARAFFIN 1.20

Cyclopentasiloxanes 5.00

C

GLYCERIN 7.00

XANTHAN GUM 0.15

MAGNESIUM ALUMINUM SILICATE 0.60

DISODIUM EDTA 0.10

AQUA (WATER) ad 100

D

Preservatives q.s.

PERFUME 0.20

e

TROMETHAMINE q.s.

production:

All phases are prepared separately. Phase C: Xanthan gum and magnesium aluminum silicate are heated to 75-80 ° C and mixed with the other ingredients. Phase A is added to Phase C at 75 ° C. After homogenization, phase B is added at 60 ° C. After homogenization, phase D is added at 40 ° C. Phase E is then added (pH = 6.5).

Example 12: Sunscreen (SPF: 28.3)

Ingredient (INCI) [%] A PROPYLENE GLYCOL 2.00

AQUA (WATER) ad 100 CARBOMER 0.30

B

N- (2-ethylhexyl) -N- (butyl) -3-aminopropanoic acid 2-ethylhexyl ester 7.50

GLYCERYL STEARATE, PEG-100 STEARATE 2.00 BENZOPHENONE-3 5.00

ETHYLHEXYL SALICYLATE 5.00

ETHYLHEXYL METHOXYCINNAMATE, BHT 10.00

4-METHYLBENZYLIDENE CAMPHOR 2.00

ISOPROPYL PALMITATE 1.00 CETYL PEG / PPG-10/1 DIMETHICONE 2.00

CYCLOPENTASILOXANE 1.00

TRIMETHYLSILOXYSILICATE, DIMETHICONE 1.00

C

Preservatives q.s. PERFUME q.s.

TRIETHANOLAMINE 0.30

production:

Phases A and B are heated to 75 ° C, B is slowly added to A. Phase C is added at 40 ° C and then homogenized.

Example 13: Sunscreen (SPF: 28.3)

Ingredient (INCI) [%] A

PROPYLENE GLYCOL 2.00

AQUA (WATER) ad 100

CARBOMER 0.30 B N- (2-ethylhexyl) -N- (acetyl) -3-aminopropanoic acid 2-ethylhexyl ester 10.00

GLYCERYL STEARATE, PEG-100 STEARATE 2.00 BENZOPHENONE-3 5.00

ETHYLHEXYL SALICYLATE 5.00 ETHYLHEXYL METHOXYCINNAMATE, BHT 10.00

4-METHYLBENZYLIDENE CAMPHOR 2.00 ISOPROPYL PALMITATE 1.00

CETYL PEG / PPG-10/1 DIMETHICONE 2.00

CYCLOPENTASILOXANE 1.00

TRIMETHYLSILOXYSILICATE, DIMETHICONE 1.00 C preservative q.s.

PERFUME q.s.

TRIETHANOLAMINE 0.30

Preparation: Phases A and B are heated to 75 ° C, B is slowly added to A.

Phase C is added at 40 ° C and then homogenized.

Example 14: Spray

Ingredient (INCI) [%] A

N- (2-ethylhexyl) -N- (acetyl) -3-aminopropanoic acid 2-ethylhexyl ester 6.25

BENZOPHENONE-3 1.50 ETHYLHEXYL METHOXYCINNAMATE, BHT 3.50

DICAPRYLYL CARBONATE 0.50

DECYL OLEATE 0.25

POLYGLYCERYL-3 METHYLGLUCOSE DISTEARATE 1.00

ISOPROPYL PALMITATE 0.50 B

AQUA (WATER) ad 100 GLYCERINE 3.00

Preservatives q.s.

CARBOMER 0.10

SODIUM HYDROXIDE 0.25 C

PERFUME 0.20

production:

Phases A and B are heated to 80 ° C, A is slowly added to B. Phase C is added at 40 ° C and then homogenized.

Example 15: Spray

Ingredient (INCI) [%]

A

N- (2-ethylhexyl) -N- (2-ethylhexoyl) -3-aminopropanoic acid-2 ethylhexyl ester 7.50

BENZOPHENONE-3 1.50

ETHYLHEXYL METHOXYCINNAMATE, BHT 3.50

DICAPRYLYL CARBONATE 0.50

DECYL OLEATE 0.25

POLYGLYCERYL-3 METHYLGLUCOSE DISTEARATE 1.00

ISOPROPYL PALMITATE 0.50

DI ETHYLHEXYL CARBONATE 0.50

B

AQUA (WATER) ad 100

GLYCERINE 3.00

Preservatives q.s.

CARBOMER 0.10

SODIUM HYDROXIDE 0.25

C PERFUME 0.20

production:

Phases A and B are heated to 80 ° C, A is slowly added to B.

Phase C is added at 40 ° C and then homogenized.

Example 16: Spray

Ingredient (INCI) [%]

A

N- (2-ethylhexoyl) -N- (2-ethylhexyl) -3-amino propanoic acid ethyl ester 25.00

STEARETH-21 2.50 Arlatone 985 5.00

PARAFFINUM LIQUIDUM (MINERAL OIL) 5.00

DIMETHICONE 1.00

MYRISTYL ALCOHOL 4.00 B AQUA (WATER) ad 100

GLYCERINE 3.00

CARBOMER 1.00 C

Preservatives q.s. D

TROMETHAMINE 0.10

AQUA (WATER) 1.00

production: Phase A is heated to 75 ° C and slowly added to B. Then C is added to A / B and homogenized. Then D is added to adjust the pH.

Example 17: Spray

Ingredient (INCI) [%]

A N- (2-ethylhexoyl) -N- (2-ethylhexyl) -3-amino propanoic acid ethyl ester 22.50

STEARETH-21 2.00

Arlatone 985 4.00

PARAFFINUM LIQUIDUM (MINERAL OIL) 7.50 DIMETHICONE 1.00

MYRISTYL ALCOHOL 4.00

B

AQUA (WATER) ad 100

GLYCERIN 3.00 CARBOMER 0.10

C

Preservatives q.s.

D

TROMETHAMINE 0.15 AQUA (WATER) 1.50

production:

Phase A is heated to 75 ° C and slowly added to B. Then C is added to AB and homogenized. Then D is added to adjust the pH. Example 18: Emulsion

Ingredient (INCI) [%]

A

N- (2-ethylhexoyl) -N- (dodecyl) -3-amino propanoic acid ethyl ester 25.00

MYRISTYL ALCOHOL, MYRISTYL GLUCOSIDE 5.00

ISOSTEARYL ISOSTEARATE 2.00

CETYL ALCOHOL 2.00

B

AQUA (WATER) ad 100

CARBOMER 0.40

C

SODIUM HYDROXIDE q.s.

D

Preservatives q.s.

PERFUME q.s.

production:

Phase A is heated to 80 ° C and slowly added to B (75 ° C). Then C is added to A / B and homogenized. Then D is added.

Example 19: O / W After Sun Lotion

Ingredient (INCI) [%]

A N- (2-ethylhexoyl) -N- (2-ethylhexyl) -3-amino propanoic acid ethyl ester 10.00 BISABOLOL 0.30

CETEARYL ALCOHOL, CETEARYL 4.00 GLUCOSIDE

CAPRYLIC / CAPRIC TRIGLYCERIDE 2.00 CYCLOPENTASILOXANE 2.00

DIMETHICONE 1.00 B

AQUA (WATER) ad 100

GLYCERIN 3.00 preservative q.s.

C

XANTHAN GUM 0.50

Preparation: phases A and B are heated separately to 75 ° C., phase C is slowly added to B and homogenized. A is then added to B / C at 75 ° C. and homogenized.

Example 20: Preparations

The following are examples of formulations for cosmetic preparations which contain compounds of the formula I. For the rest, the INCI names of the commercially available compounds are given.

UV-Pearl, OMC stands for the preparation with the INCI name: Water (for EU: Aqua), ethylhexyl methoxycinnamate, silica, PVP, chlorphenesin, BHT; this preparation is commercially available under the name Eusolex DarmUV Pearl ™ OMC from Merck KGaA, Darmstadt. The other UV pearls listed in the tables are each composed analogously, with OMC being replaced by the specified UV filters.

Table 1 W / O emulsions (numbers in% by weight)

Table 1 (continued)

Table 1 (continued)

Table 2: O / W emulsions, numbers in% by weight

Table 2 (continued)

Table 2 (continued)

Table 3: Gels, numbers in% by weight

Claims

claims

1. Use of a compound of formula I.

where R ¹ , R ² and R ^{3 can be the} same or different and are selected from - straight-chain or branched d- to C ₂ 4 -alkyl groups, - straight-chain or branched C ₃ - to C ₂₄ -alkenyl groups, - straight-chain or branched Cr to C ₂₄ -hydroxyalkyl groups, where the hydroxyl group can be bound to a primary or secondary carbon atom of the chain and the alkyl chain can also be interrupted by oxygen, and / or C ₃ - to Cio-cycloalkyl groups and / or C ₃ - to Cι ₂ - Cycloalkenyl groups, where the rings can also each be bridged by - (CH ₂ ) _n - groups with n = 1 to 3 as formulation auxiliaries in the production of cosmetic or dermatological preparations.

2. Use according to claim 1 of a compound of formula I according to claim 1, wherein the formulation aid serves as a solubilizer.

3. Use according to claim 1 of a compound of formula I according to claim 1, wherein the formulation aid serves as a penetration enhancer.

4. Use according to claim 1 of a compound of formula I according to claim 1, wherein the formulation aid serves as an enhancer.

5. Use according to at least one of the preceding claims, characterized in that ethyl 3- (acetyl-butylamino) propionate is excluded from the compounds of the formula I.

6. Use according to at least one of the preceding claims, characterized in that R ¹ and R ^{3 can be the} same or different and are selected from ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethyl-hexyl, n-decyl, n-dodecyl, n-tetradecane, n-hecadecane, n-octadecane, n-eicosane, n-docosane and n-tetracosane, where R ^{1 is} preferably 2-ethyl-hexyl and / or R ^{3 is} preferably n-octyl, 2-ethyl-hexyl, n-decyl or n-dodecyl.

7. Use according to at least one of the preceding claims, characterized in that R ^{2 is} selected from the group consisting of the elements methyl, n-propyl, isopropyl, n-pentyl, n-heptyl, 1-ethyl-pentyl, n -Nonyl, n-undecyl, wherein R ^{2 is} preferably selected from the group containing the elements methyl, 1-ethyl-pentyl, n-nonyl and n-undecyl.

8. Use according to at least one of the preceding claims, characterized in that the compound according to formula I is selected from the compounds N-acetyl-N- (2-ethylhexyl) -3- aminopropanoic acid ethyl ester, N-acetyl-N- (dodecyl) - 3-aminopropanoic acid ethyl ester, N- (2-ethylhexoyl) -N- (butyl) -3-aminopropanoic acid ethyl ester, N-acetyl-N- (butyl) -3-aminopropanoic acid butyl ester, N- (2-ethylhexoyl) -N- (2-ethylhexyl) -3-aminopropanoic acid ethyl ester, N- (2-ethylhexoyl) -N- (dodecyl) -3-aminopropanoic acid ethyl ester, N-acetyl- N- (2-ethylhexyl) -3-aminopropanoic acid butyl ester, N-acetyl-N- (Do- decyl) -3-aminopropanoic acid butyl ester, N- (2-ethylhexoyl) -N- (butyl) -3- aminopropanoic acid butyl ester, N- (2-ethylhexoyl-N- (2-ethylhexyl) -3- aminopropanoic acid butyl ester, N- ( 2-ethylhexoyl) -N- (dodecyl) -3-aminopropanoic acid butyl ester, N-acetyl-N- (butyl) -3-aminopropanoic acid 2-ethylhexyl ester, N-acetyl-N- (2-ethylhexyl) -3 -aminopropanoic acid-2-ethylhexyl ester, N-acetyl-N- (dodecyl) -3-aminopropanoic acid-2-ethyl- hexyl ester, N- (2-ethylhexoyl) -N- (butyl) -3-aminopropanoic acid 2-ethylhexyl ester, N- (2-ethylhexoyl) -N- (2-ethylhexyl) -3-aminopropanoic acid 2-ethylhexyl ester, N- (2-ethylhexoyl) -N-dodecyl) -3-aminopropanoic acid 2-ethylhexyl ester, the compound of formula I being particularly preferably N-acetyl-N- (2-ethylhexyl) -3-aminopropanoic acid ethyl ester is.

Compound according to formula I.

where R ¹ , R ² and R ^{3 can be the} same or different and are selected from - straight-chain or branched d- to C ₂₄ -alkyl groups, - straight-chain or branched C ₃ - to C ₂₄ -alkenyl groups, - straight-chain or branched d- bis C ₂₄ -hydroxyalkyl groups, where the hydroxy group can be bonded to a primary or secondary carbon atom of the chain and the alkyl chain can also be interrupted by oxygen, and / or - C ₃ - to Cio-cycloalkyl groups and / or C ₃ - to C12- Cycloalkenyl groups, where the rings can also be bridged by - (CH ₂ ) _n - groups with n = 1 to 3, with the proviso that either R ^{1 is} 2-ethyl-hexyl or R ^{2 is} 1-ethyl-pentyl and R ^{3 is} n-octyl, 2-ethyl-hexyl, n-decyl or n-dodecyl or R ^{2 is} methyl and R ¹ and R ^{3 are} different or the compound of formula I is N- (2 -Ethylhexoyl) - N- (butyl) -3-aminopropanoic acid butyl ester.

10. A compound according to claim 9, characterized in that R ¹ vvoorrzzuuggsswweeiissee sstteehhtt fürr 22 - EEtthhyyll - hheexxyyll uundndd // ooddeerr RR ³³ preferably stands for n-octyl, 2-ethyl-hexyl, n-decyl or n-dodecyl.

11. A compound according to at least one of claims 9 or 10, characterized in that the compound according to formula I is selected from the compounds N- (2-ethylhexoyl) -N- (2-ethylhexyl) -3-aminopropanoic acid ethyl ester, N- (2nd -Ethylhexoyl) -N- (dodecyl) -3-aminopropanoic acid ethyl ester, N-acetyl-N- (2-ethylhexyl) - 3-aminopropanoic acid butyl ester, N-acetyl-N- (dodecyl) -3-amino propanoic acid butyl ester, N- (2 -Ethylhexoyl) -N- (butyl) -3-aminopropanoic acid butyl ester, N- (2-ethylhexoyl-N- (2-ethylhexyl) -3-amino propanoic acid butyl ester, N- (2-ethylhexoyl) -N- (dodecyl) -3-aminopropane acid butyl ester, N-acetyl-N- (butyl) -3-amino propanoic acid 2-ethylhexyl ester, N-acetyl-N- (2-ethylhexyl) -3-amino propanoic acid 2-ethylhexyl ester, N -Acetyl-N- (dodecyl) -3-aminopropanoic acid 2-ethylhexyl ester, N- (2-ethylhexoyl) -N- (butyl) -3-aminopropanoic acid 2-ethylhexyl ester, N- (2-ethylhexoyl) -N- (2-ethylhexyl) -3-aminopropanoic acid 2-ethylhexyl ester, N- (2-ethylhexoyl) -N-dodecyl) -3- aminopropanoic acid 2-ethylhexyl ester.

12. A process for the preparation of a compound of formula I according to at least one of claims 9 to 11, characterized in that a compound of formula II

is reacted with an acid derivative R ² -C (= 0) -X, where X is -CI, -0-C (= 0) -R ⁴ or -OR ⁴ , where -R ⁴ is a straight-chain or branched C to C ₂₄ alkyl group, which is preferably identical to R ² .

13. A process for the preparation of a compound of formula I according to claim 12, characterized in that the compound of formula II is obtained by reacting a compound of formula III is reacted with an amine R ³ -NH ₂ .

14. Preparation containing at least one formulation aid according to formula I.

wherein R ¹ , R ² and R ^{3 may be the} same or different and are selected from -. straight-chain or branched Cr to C ₂₄ -alkyl groups, - straight-chain or branched C ₃ - to C ₂₄ -alkenyl groups, - straight-chain or branched d- to C ₂₄ -hydroxyalkyl groups, where the hydroxyl group can be bound to a primary or secondary carbon atom of the chain and further the alkyl chain can also be interrupted by oxygen, and / or - C ₃ - to Cio-cycloalkyl groups and / or C ₃ - to C12-cycloalkenyl groups, the rings also each by - (CH2) _n - groups with n = 1 to 3 can be bridged, and at least one active substance, the processing and / or application of which is facilitated by the formulation aid, ethyl 3- (acetyl-butylamino) propionate being excluded from the compounds of the formula I.

15. Preparation according to claim 14, characterized in that the at least one active substance is at least one repellent, preferably selected from N, N-diethyl-3-methylbenzamide, 3- (acetyl-butylamino) propionic acid ethyl ester, Dimethyl phthalate, butopyronoxyl, 2,3,4,5-bis (2-butylene) tetrahydro-2-furaldehyde, N, N-caprylic acid diethylamide, N, N-diethylbenzamide, o-chloro-N, N-diethylbenzamide, dimethyl carbate, Di-n-propylisocinchomeronate, 2-ethylhexane-1,3-diol, N-octyl-bi- cyclohepene diecarboximide, piperonyl butoxide, 1- (2-methylpropyloxycarbonyl) -2- (hydroxyethyl) piperidine or mixtures thereof, at least one repellent being particularly preferably selected from N, N-diethyl-3-methylbenzamide, 3- (acetyl-butyl - Amino) propionic acid ethyl ester 1 - (2-methylpropyloxycarbonyl) -2- (hydroxyethyl) piperidine or mixtures thereof.

16. Preparation according to claim 14, characterized in that the at least one active substance is an insoluble or poorly soluble active substance selected from the group of organic UV filters, flavone derivatives, chromone derivatives, aryloximes or parabens.

17. Preparation according to at least one of the preceding claims containing at least one compound of the formula I, characterized in that the preparations contain one or more compounds of the formula I in an amount of 0.01 to 20% by weight, preferably in an amount of 0 , 1 to 10 wt .-% contains.

18. Preparation according to at least one of the preceding claims for protecting body cells against oxidative stress, in particular for reducing skin aging, characterized in that it preferably contains one or more further antioxidants and / or vitamins, preferably selected from vitamin A palmitate, vitamin C. and its derivatives, DL-α-tocopherol, tocopherol E-acetate, nicotinic acid, pantothenic acid and biotin.

19. Preparation according to at least one of the preceding claims, wherein the preparation contains, in addition to the at least one compound of the formula I, one or more UV filters, which are preferably selected from the group consisting of 3- (4 ^' -methylbenzylidene) dl camphor , 1 - (4-tert-Butylphenyl) -3- (4-methoxyphenyl) propane-1,3-dione, 4-isopropyldibenzoylmethane, 2-hydroxy-4-methoxybenzophenone, octyl methoxycinnamate, 3,3,5-trimethylcyclohexyl salicylate, 4- (Dimethylamino) benzoic acid 2-ethylhexyl ester, 2-cyano-3,3-di- phenyl-acrylic acid-2-ethylhexyl ester, 2-phenylbenzimidazole-5-sulfonic acid and their potassium, sodium and triethanolamine salts.

20. A method for producing a preparation, characterized in that a compound of formula I with residues according to claim 1 is mixed with a cosmetically or dermatologically suitable carrier.

21. Use of a compound of formula I, wherein the variables have the meaning given in claim 1, for the preparation of a preparation suitable for topical use.