EP2654687A1 - Dihydroxyacetone monoether - Google Patents

Abstract

The invention relates to the use of dihydroxyacetone monoethers as self-tanning substances, to preparations containing dihydroxyacetone monoethers as well as to specific dihydroxyacetone monoethers and to a method for producing same.

Description

 Dihydroxyacetonmonoether

The present invention relates to the use of

Dihydroxyacetone monoethers as self-tanning substance, preparations containing dihydroxyacetone monoethers, as well as certain

 Dihydroxyacetone monoethers and a process for their preparation.

The trend away from sophisticated paleness to "healthy, sporty brown skin" has been unbroken for years, and people are exposing their skin to sunshine for a tanned complexion that causes pigmentation through melanin formation However, in addition to the acute injury (sunburn), long-term damage due to excessive exposure to light from the UVB range (wavelength 280-320 nm), such as an increased risk of developing skin cancer Excessive exposure to UVB and UVA radiation (wavelength: 320-400 nm) produces highly reactive radical species that continue to multiply upon completion of irradiation, resulting in wrinkling and skin aging.

Natural protection against the negative effects of solar radiation is provided by the tanning (pigmentation) of the skin. The epidermis contains in its lowest layer, the basal layer, in addition to the basal cells, individual pigment-forming cells, the melanocytes. UV light in these cells stimulates the production of melanin, which is transported to the keratinocytes (horny cells) where it becomes visible as a brown skin color. Melanin protects the cell nuclei from further irradiation and the resulting negative effects on the cell DNA.

Depending on the chemical composition of the biochemically formed pigments is between the brownish-black eumelanin and the reddish-yellow pheomelanin distinguished. The observed skin tone is determined by the ratio of these two types of melanin.

Produced by the amino acid tyrosine, this pigmentation is primarily initiated by UVB radiation and is termed "indirect pigmentation." Its development proceeds over several days, resulting in a few weeks of suntan is used, predominantly colorless melanin precursors are oxidized by UVA radiation to dark colored melanin. Since this oxidation is reversible, it leads to a short-lasting tanning of the skin.

An artificial tanning of the skin can be produced externally with the help of make-up and orally by taking carotenoids. Far more popular, however, is the artificial tanning of the skin, which can be achieved by applying so-called self-tanner.

The most commonly used substance worldwide for this purpose is 1,3-dihydroxyacetone (DHA), which is used in an amount of 700 t / a. Self-tanning agents can be reacted with the proteins and amino acids of the horny layer of the skin in the sense of a Maillard reaction or via a Michael addition, whereby polymers which give the skin a brownish hue emerge via a not yet fully elucidated reaction pathway. This reaction is completed in about 24 hours. The tan thus obtained is not washable and is removed only with the normal Hautabschuppung.

There are already known various substances which are used as self-tanner and which are described below.

DHA is a water-soluble crystalline solid that is not stable under neutral to basic conditions. These Instability is also associated with the development of cosmetically undesirable off-odors.

A problem which can frequently occur when using self-tanning substances, in particular with 1,3-dihydroxyacetone, is that the natural tanning of the skin is discolored to orange by the predominance of the yellow component. This is often perceived by many users as a disadvantage and perceived as unnatural.

There is therefore still a need for dermatologically acceptable skin-coloring substances which are suitable for use in cosmetic and / or dermatological preparations or medical products.

The object underlying the present invention was therefore to provide self-tanning substances having improved properties, in particular a more natural skin color.

Surprisingly, it has now been found that certain dihydroxyacetone monoethers are self-tanning substances which are able to develop a more natural hue on the skin and accelerate the tanning reaction.

In the international application WO 2006/018104 compounds of the general formula

wherein X is O, S (O) _m or NR ¹ ; Y is H, -SiR ² R ³ R ⁴ or - [Si (R ² ) ₂ ] _q SiR ³ R ⁴ R ⁵ or -Sp-R; R ¹ is H, C _1-24 alkyl or R; R ² , R ³ , R ⁴ and R ⁵ are 1-30-alkyl; Sp is - (CH ₂ ) _n -, - (CH ₂ ) _n -C (= O) - (CH ₂ ) ₀ - or - (CH ₂ ) _n -C (= O) - (CH ₂ ) oX- (CH ₂ ) _p -; m is 0, 1 or 2; n, o, p stand for 0 to 24; R is a substituent of UV radiation absorbed. This document further discloses the cosmetic

Use of these compounds as sunscreen filters. That certain compounds covered by this formula are also known as

Selbstbräunungssubstanz can act, however, is not mentioned or suggested in this application.

WO 2006/024361 A1 describes the use of dimeric dihydroxyacetone monoester derivatives as precursors for self-tanning compounds. EP 0709081 A1 and EP 0796838 A1 disclose preparations containing dihydroxyacetone ester derivatives which are precursors for dihydroxyacetone. None of these documents discloses the use of dihydroxyacetone monoether derivatives as a self-tanning substance. A first object of the present invention is therefore the

Use of a compound of the formula (I)

as a self-tanning substance, wherein R 1 is a branched or unbranched alkyl radical having 1 to 20 C atoms, a branched or unbranched alkenyl radical having 2 to 20 C atoms or a branched or unbranched alkynyl radical having 2 to 20 C atoms,

wherein one or more non-adjacent and not directly to the O atom of formula (I) adjacent CH ₂ groups may be replaced by C = O or -O-,

where the radicals can be substituted by one or more OH groups, by one or more cyclic alkyl radicals having from 3 to 8 carbon atoms and / or by one or more aromatic ring systems having from 5 to 6 carbon atoms, where the one or more aromatic radicals Ring systems with one or more groups selected from -OH, -OR, -NR2, -CN, -COOR and -COOR 'may be substituted; where R stands independently for each occurrence

branched or unbranched alkyl radical having 1 to 20 carbon atoms; and wherein R 'is an aromatic ring system having 5 or 6 C atoms.

The compounds of the formula (I) can also be used in the form of their dimeric derivatives of the formula (II)

in which R 2 is H or a branched or unbranched alkyl radical having 1 to 20 C atoms and R 1 is as defined for formula (I). Preferably, R2 is methyl or ethyl. The compounds of the formula (II) may be obtained, for example, by hydrolysis in the formulation, even after addition of an activating reagent (eg an acid), or by

Skin hydrolysis can be converted to the corresponding monomeric DHA ethers of formula (I) due to the natural acidic pH of the skin.

R 1 is preferably a branched or unbranched alkyl radical having 1 to 20 C atoms,

wherein one or more non-adjacent and not directly to the O atom of formula (I) adjacent CH ₂ groups may be replaced by C = O or -O-,

where the radicals can be substituted by one or more OH groups, by one or more cyclic alkyl radicals having from 3 to 8 carbon atoms and / or by one or more aromatic ring systems having from 5 to 6 carbon atoms, where the one or more aromatic radicals Ring systems with one or more groups selected from -OH and -OR may be substituted,

and wherein R is defined as previously described. R1 particularly preferably represents a branched or unbranched alkyl radical having 1 to 20 C atoms,

wherein one or more non-adjacent and not directly to the O atom of formula (I) adjacent CH ₂ groups may be replaced by C = O or -O-,

where the radicals can be substituted by one or more OH groups, by one or more cyclic alkyl radicals having from 5 to 6 carbon atoms and / or by one or more aromatic ring systems having from 5 to 6 carbon atoms, where the one or more aromatic radicals are substituted by one or more OH radicals Ring systems with one or more groups -OR may be substituted,

and wherein R is defined as previously described.

In the above-mentioned embodiments, the branched or unbranched alkyl group preferably has 1 to 17 carbon atoms.

The cyclic alkyl radical having 5 to 6 C atoms is preferably one

Cyclohexyl.

 The aromatic ring system having 5 to 6 C atoms is preferably a phenyl radical.

 R is preferably a branched or unbranched alkyl radical having 1 to 8 C atoms, particularly preferably methyl or ethyl.

Most preferably, R1 is selected from the following radicals: benzyl, 2-ethylhexyl, unbranched or branched hexyl,

unbranched or branched heptyl, unbranched or branched pentadecyl, unbranched or branched heptadecyl, cyclohexylmethyl, cyclohexylethyl, phenylethyl, methoxyphenylmethyl, 2,3-dihydroxypropyl, 2-oxy-3-hydroxypropyl , Hydroxyethyl, hydroxy methyl, 2-hydroxy-propyl and 2-hydroxy-ethoxy-ethyl. According to the invention, the compounds of the formula (I) are preferably selected from the compounds of the formulas (Ia) to (Ik)

Particular preference is given here to the compounds (Ia) to (If), very particular preference to the compounds (Ia) to (Id).

In another possible embodiment, R 1 preferably represents a branched or unbranched alkyl radical having 1 to 20 C atoms, the radicals having one or more OH groups, having one or more cyclic alkyl radicals having 5 to 6 C atoms and / or substituted with one or more aromatic ring systems having 5 to 6 carbon atoms wherein the one or more aromatic ring systems may be substituted with one or more groups selected from -OH and -OR,

and wherein R is defined as previously described.

In this embodiment, R.sup.1 particularly preferably represents a branched or unbranched alkyl radical having 1 to 20 C atoms, the radicals having one or more cyclic alkyl radicals having 5 to 6 C atoms and / or having one or more aromatic ring systems having 5 to 6 C atoms may be substituted, wherein the one or more aromatic ring systems having one or more groups selected from

May be substituted with -OH and -OR

and wherein R is defined as previously described. Preferred embodiments of the cyclic alkyl radicals, of

aromatic ring system, as well as the radical R are here defined as described above.

 Very particularly preferred compounds of the formula (I) are in this case the compounds of the formula (Ia), (Ib), (Ic), (Id), (Ie) and (If).

For the purposes of the present invention, a branched or unbranched (straight-chain) alkyl radical having 1 to 8 C atoms is, for example, methyl, ethyl, isopropyl, propyl, butyl, sec-butyl or tert-butyl, pentyl, isopentyl , 1-, 2- or 3-methylbutyl, 1, 1-, 1, 2- or 2,2-dimethylpropyl, 1-ethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 1, 1 , 2- or 1,2,2-trimethylpropyl, 1, 1-, 1, 2-, 1, 3-, 2,2-, 2,3- or 3,3-dimethylbutyl, 1- or 2-ethylbutyl, 1-, 2-, 3- or 4-methylpentyl, hexyl, heptyl, 1-ethyl-pentyl, octyl or 1-ethyl-hexyl.

In the case of an alkyl radical having 1 to 17 carbon atoms, the above-listed C1 to C8-alkyl radicals may, for example, also be nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl or heptadecyl. An alkyl radical having 1 to 20 C atoms is understood in addition to the above listed radicals also octadecyl, nonadecyl or eicosyl.

According to the invention, an alkenyl radical may contain one or more double bonds. A branched or unbranched Aikyl group having 2 to 20 C atoms is, for example, allyl, vinyl, propenyl, 2- or 3-butenyl, isobutenyl, sec-butenyl, 2-methyl-1 - or 2-butenyl, 3-methyl- 1 -butenyl, 1, 3-butadienyl, 2-methyl-1,3-butadienyl, 2,3-dimethyl-1,3-butadienyl, 1-, 2-, 3- or 4-pentenyl, iso-pentenyl, hexenyl , Heptenyl or Octenyl, -C ₉ Hi ₇ , -C ₁₀ H ₁₉ to -C20H39.

An alkynyl radical may contain one or more triple bonds.

Examples of a branched or unbranched alkynyl group having 2 to 20 C atoms are ethynyl, 1- or 2-propynyl, 2- or 3-butynyl, furthermore 4-pentynyl, 3-pentynyl, hexynyl, heptynyl, octynyl, -C9H15, -C10H17 to -C20H37.

A cyclic alkyl having 3 to 8 carbon atoms referred to in the sense of

Invention saturated and partially unsaturated non-aromatic cyclic hydrocarbon groups comprising 3 to 8 carbon atoms and

may be unsubstituted or substituted. The bond to the alkyl, alkenyl or alkynyl radical of the formula (I) can be via any ring member of the cycloalkyl group. Examples of suitable cycloalkyl radicals are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl and cyclooctadienyl.

A cyclic alkyl radical having 6 C atoms is preferably cyclohexyl.

An aromatic ring system having 5 to 6 carbon atoms in the context of the present invention may be substituted or unsubstituted. Binding to the alkyl, alkenyl or alkynyl moiety of formula (I) can be via any ring member of the aromatic ring system. Examples of such aromatic ring systems having 5 to 6 C atoms are phenyl, Methoxyphenyl, 2,6-dimethoxyphenyl, 3,5-dimethoxyphenyl, 2,4-dimethoxyphenyl, 2,4,6-trimethoxyphenyl or 2,3,4-trimethoxyphenyl. Preferred are aromatic ring systems which may be substituted with one or more -OR groups. Particularly preferred are phenyl and methoxyphenyl.

The compounds of the formulas (Ia), (Ie) and (If) may have the advantage that they can release odors by cleavage of the ether radical as the corresponding alcohol during the browning reaction.

Phenethyl alcohol (obtainable by cleavage of Etherrestes of

 Compound of formula (le)) is perceived, for example, as a rose hyacinth-like fragrance. These released odors are advantageous because the perceived in the tanning reaction odor is usually perceived as negative.

The compounds of formula (I) can be derived from dimeric

The synthesis of 2,5-di-ethoxy-2,5-bis (hydroxymethyl) - [1 -4] dioxane is as disclosed in Jung et al., Journal of Organic Chemistry, 1994, 7182. The free OH groups of the ethoxylated dimer can then be replaced by an ordinary

 Veretherungsreaktion be modified with an alkyl halide or an alkyl tosylate or mesylate.

 In a last step, the monomer compounds of formula (I) can then be obtained by acid hydrolysis, for example with 95% sulfuric acid.

The synthesis is illustrated in the following reaction scheme:

It does not give the skilled person any difficulty in selecting the appropriate reaction conditions for this reaction.

Dimer dihydroxyacetone as well as the other reactants in the synthesis are commercially available or accessible by syntheses known to those skilled in the literature.

Alternatively, the preparation can also be carried out biotechnologically starting from the corresponding glycerol ether derivatives.

The compounds of the formula (I) can be used in self-tanning products, for example as an alternative to DHA and / or erythrulose.

An advantage of using the compounds of formula (I) over DHA as a self-tanning substance is, for example, that they allow the achievement of a more natural or other skin hue.

For example, compounds of formula (Ic) promote a darker coloration of the skin. With the aid of compounds of the formula (Ia), the shift to a redder hue allows a more natural skin tone

produce. Another advantage is the accelerated by the compounds of formula (I) tanning reaction.

Furthermore, the compounds of the formula (I) can also be used in combination with DHA and / or erythrulose. Another object of the present invention is therefore also the use of a compound of formula (I) as a self-tanning substance, characterized in that the use takes place together with DHA and / or erythrulose.

The combination preferably takes place with DHA.

For example, such a combination can have a positive influence on the shade of shade achieved in the browning reaction. Thus, the resulting skin tone by the specific selection of one or more particular compounds of formula (I) and by setting a certain ratio of the compounds of formula (I) to DHA and / or erythrulose to the specific needs of

Customize user.

 Another advantage of the combination may be that the

Compounds of formula (I) can accelerate the tanning reaction by dihydroxyacetone or by a mixture of self-tanning substances containing dihydroxyacetone. This allows a shortening of the application time. Throughout the document, the term self-tanner or

 Self tanning substance or self tanning substance synonymous

used. These terms refer to a substance which dyes the skin and can react in the sense of a Maillard reaction or via a Michael addition with the amino acids of the protein-containing matrix and thus form melanoids. The melanoids are yellow-brown to almost black-colored, organic compounds, which are mainly due to the

Reaction of carbonyl groups with amino or thiofunktionen can arise. The principle of staining to form melanoid is the basic staining principle of self-tanning substances.

The use according to the invention is preferably non-therapeutic. Another object of the present invention is a preparation containing at least one compound of formula (I)

where R 1 is a branched or unbranched alkyl radical having 1 to 20 C atoms, a branched or unbranched alkenyl radical having 2 to 20 C atoms or a branched or unbranched alkynyl radical having 2 to 20 C atoms,

wherein one or more non-adjacent and not directly to the O atom of formula (I) adjacent CH ₂ groups may be replaced by C = O or -O-,

which radicals can be substituted by one or more OH groups, one or more cyclic alkyl radicals having 3 to 8 C atoms and / or by one or more aromatic ring systems having 5 to 6 C atoms, wherein the one or more aromatic ring systems may be substituted with one or more groups selected from -OH, -OR, -NR ₂ , -CN, -COOR and -COOR '; where R stands independently for each occurrence

branched or unbranched alkyl radical having 1 to 20 carbon atoms; and wherein R 'is an aromatic ring system having 5 or 6 C atoms.

The compounds of the formula (I) can also be used in the form of their dimeric derivatives of the formula (II)

be included in the preparation, wherein R2 is H or a branched or non-branched alkyl having 1 to 20 carbon atoms and R1 is as defined for formula (I). Preferably, R2 is methyl or ethyl.

The preparations may continue to have a certain percentage of

correspondingly substituted DHA diethers.

The preparations are usually topically applicable preparations, for example cosmetic or cosmetic preparations

dermatological formulations or medical devices. The preparations in this case contain a cosmetically or dermatologically suitable carrier and, depending on the desired property profile, optionally further suitable ingredients. Is it pharmaceutical

Preparations, the preparations in this case contain a pharmaceutically acceptable carrier and optionally further pharmaceutical active ingredients.

For the purposes of the present invention, the term agent or formulation is used synonymously in addition to the term preparation.

Topically applicable means for the purposes of the invention that the preparation is applied externally and locally, i. that the preparation must be suitable, for example, to be applied to the skin can.

The preparations may comprise or contain, consist essentially of or consist of said necessary or optional ingredients. Any compounds or components which may be used in the compositions are either known and commercially available or may be synthesized by known methods.

It is preferably a cosmetic or pharmaceutical preparation; most preferably it is a cosmetic preparation. The at least one compound of the formula (I) is used in the preparations according to the invention in amounts of from 0.01 to 20% by weight, preferably in amounts of from 0.05 to 10% by weight, more preferably in amounts of 0.1% by weight .-% to 5 wt .-% and most preferably in amounts of 0.5 to 2 wt .-%, based on the total amount of

Preparation, used. It prepares the expert no

Difficult to select the quantities according to the intended effect of the preparation. Furthermore, the preparations according to the invention may contain at least one further self-tanning substance as further ingredient.

Advantageous self-tanning substances which may be used include:

 1, 3-dihydroxyacetone, glycerol aldehyde, hydroxymethylglyoxal, γ-dialdehyde, erythrulose, 6-aldo-D-fructose, ninhydrin, 5-hydroxy-1,4-naphthoquinone (juglone) or 2-hydroxy-1,4-naphthoquinone (Lawson ). Very particular preference is the 1, 3-dihydroxyacetone, erythrulose or their

Combination. Preferably, the further self-tanning substance is selected from DHA and erythrulose.

Preferably, the at least one further self-tanning substance in the preparation in an amount of 0.01 to 20 wt .-%, particularly preferably in an amount of 0.5 to 15 wt .-% and most preferably in an amount of 1 to 5 Wt .-%, based on the total amount of the preparation.

Preparations with self-tanning properties, especially those containing dihydroxyacetone, tend to be used on the

human skin to malodors, presumably by degradation products of dihydroxyacetone itself or by products of side reactions caused by the users and sometimes perceived as unpleasant. It has been found that these off-odors are avoided when using formaldehyde scavengers and / or flavonoids. Therefore, the preparation according to the invention can also

Formaldehydfänger and possibly flavonoids to improve the odor. However, the compounds of the formula (I) which are claimed for preparations according to the invention can also in their turn contribute to improving the odor. Preferably, the formaldehyde scavenger is selected from the group alkali metal, alkaline earth metal or ammonium disulfite.

The preparations according to the invention may particularly preferably contain flavonoids for improving odor and for

Tanning scrubber included.

The flavonoid additionally acts as a stabilizer for the self-tanner or the self-tanning substances and / or reduces or avoids or improves storage-dependent off-odors, which can also be caused by additives or auxiliaries contained.

Preferably, it is a flavonoid in which one or more phenolic hydroxy groups are blocked by etherification or esterification. For example, have hydroxyethyl-substituted

Flavonoids, such as preferably troxerutin, troxequercetin,

 Troxeisoquercetin or troxeluteolin, and flavonoid sulfate or

Flavonoid phosphates, such as preferably rutin sulfates, proved to be particularly suitable flavonoids. Particularly preferred in the context of the use according to the invention are rutin sulfate and troxerutin. Very particularly preferred is the use of troxerutin. The preferred flavonoids have a non-positively charged Flavangrundkörper. It is believed that by these flavonoids

Metal ions such as Fe ²⁺ / Cu ^{2+ be} complexed and so autooxidation processes in fragrances or compounds whose degradation to

Bad odors leads, prevented or reduced.

In addition to the compounds of the formula (I), preferred preparations additionally contain at least one UV filter. Organic UV filters, called hydrophilic or lipophilic

 Sunscreen filters are effective in the UVA range and / or UVB range and / or IR and / or VI S range (absorbers). These substances can be obtained, in particular, from cinnamic acid derivatives, salicylic acid derivatives,

Camphor derivatives, triazine derivatives, β, β-diphenylacrylate derivatives, p-aminobenzoic acid derivatives and polymeric filters and silicone filters described in application WO-93/04665.

Further examples of organic filters are given in patent application EP-A 0 487 404. In the following, the named UV filters are usually named according to the INCI nomenclature.

In particular suitable for a combination are:

para-aminobenzoic acid and its derivatives: PABA, ethyl PABA, ethyl dihydroxypropyl PABA, ethylhexyl dimethyl PABA, e.g. B. under the name "Escalol 507" from the company. ISP, glyceryl PABA, PEG-25 PABA, z. B. sold under the name "Uvinul P25" from the company. BASF.

Salicylates: Homosalates sold under the name "Eusolex HMS" by Merck; Ethyl hexyl salicylates, e.g. B. sold under the name "Neo Heliopan OS" from the Fa. Symrise, Dipropylene glycol salicylate, z. B. under the name "Dipsal" from the company. Scher, TEA salicylate, z. B. marketed under the name "Neo Heliopan TS" of the Fa. Symrise. β, β-diphenylacrylate derivatives: octocrylenes, e.g. B. under the name "Eusolex® OCR" from Merck "," Uvinul N539 "from BASF, Etocrylene, z. B. sold under the name "Uvinul N35" from BASF.

Benzophenone Derivatives: Benzophenone-1, e.g. Sold under the name "Uvinul 400"; Benzophenone-2, e.g. Sold under the name "Uvinul D50"; Benzophenone-3 or oxybenzone, e.g. B. sold under the name "Uvinul M40" Benzophenone-4, z. Sold under the name "Uvinul MS40"; Benzophenone-9, e.g. B. sold under the

Name "Uvinul DS-49" from BASF, Benzophenone-5,

Benzophenone-6, e.g. B. marketed under the name "Helisorb 11" by the company Norquay, Benzophenone-8, z. B. sold under the name

"Spectra-Sorb UV-24" from American Cyanamid, benzophenone-12 n-hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate or 2-hydroxy-4-methoxybenzophenone, sold by Merck, Darmstadt under the name Eusolex® 4360.

Benzylidene camphor derivatives: 3-benzylidenecamphor, e.g. B. sold under the name "Mexoryl SD" from the company. Chimex, 4-

Methylbenzylidenecamphor, z. B. sold under the name "Eusolex 6300" from the company Merck, Benzylidenecamphorsulfonsäure, z. B. under the name "Mexoryl SL" from the company Chimex, Camphor

benzalkonium methosulfates, e.g. Sold under the name "Mexoryl SO" from the company. Chimex, Terephthalylidenedicamphorsulfonsäure, z. Sold under the name "Mexoryl SX" by Chimex,

Polyacrylamidomethylbenzylidenecamphor sold under the name "Mexoryl SW" from Chimex. Phenylbenzimidazole derivatives: phenylbenzimidazolesulfonic acid, e.g. B.

sold under the name "Eusolex 232" by Merck, disodium phenyl dibenzimidazole tetrasulfonate, e.g. B. marketed under the name "Neo Heliopan AP" by Fa. Symrise.

Phenylbenzotriazole derivatives: Drometrizole trisiloxanes, e.g. B. marketed under the name "Silatrizole" by the company. Rhodia Chimie,

 Methylenebis (benzotriazolyl) tetramethylbutylphenol in solid form, e.g. B. sold under the name "MIXXIM BB / 00" from the company. Fairmount Chemical, or in micronized form as an aqueous dispersion, eg. B.

sold under the name "Tinosorb M" from BASF.

Triazine derivatives: ethylhexyltriazone, e.g. B. sold under the name "Uvinul T150" from the company. BASF, Diethylhexylbutamidotriazone, z. B.

sold under the name "Uvasorb HEB" from the company Sigma 3V, 2,4,6-tris (diisobutyl 4'-aminobenzalmalonate) -s-triazines or 2,4,6-tris (biphenyl) -1,3, 5-triazines sold as Tinosorb A2B by BASF, 2,2 '- [6- (4-methoxyphenyl) -1, 3,5-triazine-2,4-diyl] bis [5- (2-ethylhexyl) oxy] - phenol, sold as Tinosorb S by BASF, N2, N4-bis [4- [5- (1, 1-dimethylpropyl) -2-benzoxazolyl] phenyl] -N6- (2-ethylhexyl) -1, 3,5-triazine -2,4,6-triamine sold as Uvasorb K 2A from Sigma 3V.

Anthraniline derivatives: menthyl anthranilate, e.g. B. sold under the

Name "Neo Heliopan MA" from the company Symrise.

Imidazole derivatives: Ethylhexyldimethoxybenzylidenedioxoimidazoline propionate.

Benzalmalonate Derivatives: Polyorganosiloxanes containing functional benzalmalonate groups, e.g. Polysilicone-15, e.g. Sold under the name "Parsol SLX" by Hoffmann LaRoche.

4,4-Diarylbutadiene derivatives: 1,1-dicarboxy (2,2'-dimethylpropyl) -4,4-diphenylbutadiene. Benzoxazole Derivatives: 2,4-bis [5- (1-dimethylpropyl) benzoxazol-2-yl (4-phenyl) imino] -6- (2-ethylhexyl) imino-1,3,5-triazines, e.g. B. sold under the name Uvasorb K2A from the company. Sigma 3V and mixtures containing this.

Piperazine derivatives such as the compound

 or the UV filters of the following structures

It is also possible to use UV filters based on polysiloxane copolymers with a random distribution according to the following formula, where, for example, a = 1 2; b = 58 and c = 2.8 are:

The compounds listed are only examples

specific. Of course, other UV filters can be used.

Suitable organic UV-protective substances are preferably to be selected from the following list: ethylhexyl salicylate,

Phenylbenzimidazolesulfonic acid, benzophenone-3, benzophenone-4, benzophenone-5, n-hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate, 4-methylbenzylidenecamphor, terephthalylidenedicamphorsulfonic acid, disodium phenyldibenzimidazoletetrasulfonate,

Methylenebis (benzotriazolyl) tetramethylbutylphenol, ethylhexyl triazone, diethylhexyl butamido triazone, drometrizole trisiloxane, polysilicone-15,1,1-dicarboxy (2,2'-dimethylpropyl) -4,4-diphenylbutadiene, 2,4-bis [5-1 ( dimethylpropyl) benzoxazol-2-yl (4-phenyl) imino] -6- (2-ethylhexyl) imino-1,3,5-triazines and mixtures thereof. These organic UV filters are usually incorporated in formulations in an amount of from 0.01% to 20% by weight, preferably 1% to 10% by weight. The preparations may contain, in addition to the compounds of the formula (I) and the optionally organic UV filters, as described above, further inorganic UV filters, so-called particulate UV filters.

These combinations with particulate UV filters are possible both as a powder and as a dispersion or paste of the following types.

In this case, both those from the group of titanium dioxides such.

coated titanium dioxide (e.g., Eusolex® T-2000, Eusolex® T-AQUA,

Eusolex® T-AVO, Eusolex® T-OLEO), zinc oxides (e.g., Sachtotec®),

Iron oxides or else cerium oxides and / or zirconium oxides are preferred.

Furthermore, combinations with pigmentary titanium dioxide or

Zinc oxide is possible, the particle size of these pigments being greater than or equal to 200 nm, for example Hombitan® FG or Hombitan® FF-Pharma.

It may further be preferred if the preparations contain inorganic UV filters which are prepared by customary methods, such as, for example, in US Pat

Cosmetics & Toiletries, February 1990, Vol. 105, pp. 53 64 described, were treated. In this case, one or more of the following aftertreatment components may be selected: amino acids,

Beeswax, fatty acids, fatty acid alcohols, anionic surfactants, lecithin, phospholipids, sodium, potassium, zinc, iron or aluminum salts of fatty acids, polyethylenes, silicones, proteins (especially collagen or elastin), alkanolamines, silica, alumina, other metal oxides, Phosphates, such as sodium hexametaphosphate or glycerin. Preferably used particulate UV filters are:

untreated titanium dioxides, e.g. the products Microtitanium Dioxide MT 500 B from Tayca; Titanium Dioxide P25 from Degussa,

Post-treated micronized titanium dioxides with alumina and

 Silica post-treatment such as e.g. the product "Microtitanium Dioxide MT 100 SA of Tayca; or the product "Tioveil Fin" from Uniqema,

 Aftertreated micronised titanium dioxides with alumina and / or aluminum stearates / laurate aftertreatment such as e.g. Micro Titanium

Dioxide MT 100 T from Tayca, Eusolex T-2000 from Merck,

Aftertreated micronised titanium dioxides with iron oxide and / or iron stearates aftertreatment such as e.g. the product "Microtitanium Dioxide MT 100 F" from Tayca,

Aftertreated micronised titanium dioxides with silicas,

 Alumina and silicone aftertreatment such as e.g. the product "Microtitanium Dioxide MT 100 SAS", the company Tayca,

 - Post-treated micronized titanium dioxides with

 Natrumhexameta- phosphates, such as e.g. the product "Microtitanium Dioxide MT 150 W" from Tayca.

The treated micronised titanium dioxides used for combination may also be post-treated with: octyltrimethoxysilanes; such as. the product Tego Sun T 805 of the Fa.

 Degussa,

 - silica; such as. the product Parsol T-X from DSM,

 Alumina and stearic acid; such as. the product UV-Titan M160 of the company Sachtleben,

- aluminum and glycerin; such as. the product UV titanium of the Fa.

Sachtleben Aluminum and silicone oils, such as, for example, the product UV titanium M262 from Sachtleben,

 Sodium hexamethaphosphate and polyvinylpyrrolidone,

 Polydimethylsiloxanes, e.g. the product 70250 Cardre UF TiO2SI3 "from the company Cardre,

 Polydimethylhydrogensiloxanes, e.g. the product Microtitanium

 Dioxide USP Grade Hydrophobia "from Color Techniques.

Furthermore, the combination with the following products may also be advantageous:

- Untreated zinc oxides such. B. the product Z-Cote Fa. BASF

 (Sunsmart), Nanox of the company Elementis

 Aftertreated zinc oxides such as the following products:

 • "Zinc Oxide CS-5" from Toshibi (ZnO aftertreated with

 polymethylhydrogenosiloxane)

 • Nanogard Zinc Oxide FN from Nanophase Technologies

• "SPD-Z1" from Shin-Etsu (ZnO aftertreated with a

 Silicone-grafted acrylic polymer dispersed in cyclodimethylsiloxanes

 "Escalol Z100" from ISP (alumina aftertreated ZnO dispersed in an ethylhexyl methoxycinnamate / PVP-hexadecenes / methicone copolymer blend)

 Fuji ZNO-SMS-10 from Fuji Pigment (ZnO aftertreated with silica and polymethylsilsquioxane);

 Untreated cerium oxide micropigment e.g. with the name "Colloidal Cerium Oxide" from Rhone Poulenc

 • Untreated and / or post-treated iron oxides with the

 Name Nanogar of the Fa. Arnaud.

By way of example, it is also possible to use mixtures of different metal oxides, such as, for example, titanium dioxide and cerium oxide with and without secondary treatment be such as the product Sunveil A Fa. Ikeda. In addition, mixtures of alumina, silica and

Silicon aftertreated titanium dioxide, zinc oxide mixtures such. the product UV titanium M261 from Sachtleben be used.

These inorganic UV filters are incorporated usually in an amount of 0.1 weight percent to 25 weight percent, preferably 2 wt .-% - 10 wt .-%, in the preparations. By combining one or more of the compounds mentioned with UV filter action, the protective effect against harmful

Effects of UV radiation can be optimized.

All mentioned UV filters can also be used in encapsulated form. In particular, it is beneficial to use organic UV filters in

to use encapsulated form.

The capsules in preparations to be used according to the invention are preferably present in amounts which ensure that the encapsulated UV filters in the abovementioned

 Weight percent ratios are present in the preparation.

In the described preparations, which contain according to the invention at least one compound of formula (I) may also continue

Color pigments may be included, wherein the layer structure of the pigments is not limited.

Preferably, the color pigment when used from 0.5 to 5 wt .-% should be skin-colored or brownish. The selection of a corresponding pigment is familiar to the person skilled in the art. Preferred preparations may also contain at least one further cosmetic active ingredient, for example selected from

Antioxidants, anti-aging, anti-wrinkle, anti-dandruff, anti-acne, anti-cellulite, deodorants, skin lighteners or vitamins.

The protective effect of preparations against oxidative stress or against the action of radicals can be improved if the preparations contain one or more antioxidants, wherein the skilled person has no difficulty in selecting suitable fast or delayed-acting antioxidants.

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

Glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles, (eg urocaninic acid) and their derivatives, peptides such as D, L-carnosine, D-carnosine, L-carnosine and their derivatives (eg anserine), carotenoids, carotenes (eg a-carotene, β-carotene, lycopene) and their derivatives, chlorogenic acid and its derivatives, lipoic acid and derivatives thereof (eg dihydrolipoic acid),

Aurothioglucose, propylthiouracil and other thiols (eg 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) and their salts,

Dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and its derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (for example buthionine sulfoximines,

Homocysteine sulfoximine, buthionine sulfone, penta-, hexa-,

Heptathionine sulfoximine) in very low tolerated dosages (e.g., pmol to pmol / kg), further (metal) chelators (e.g., α-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), α-hydroxy acids (e.g.

 Citric acid, lactic acid, malic acid), humic acid, bile acid,

Bile extracts, bilirubin, biliverdin, EDTA, EGTA, pentasodium ethylenediamin tetramethylene phosphonate and its derivatives, unsaturated fatty acids and their derivatives, vitamin C and derivatives (eg

Ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl acetate),

Tocopherols and derivatives (e.g., vitamin E acetate), vitamin A and derivatives (e.g., vitamin A palmitate), benzoic acid coniferyl benzoate, rutinic acid and derivatives thereof, α-glycosyl rutin, ferulic acid,

Furfurylidenglucitol, carnosine, butylhydroxytoluene, butylhydroxyanisole, nordohydroguajaretic acid, trihydroxybutyrophenone, quercitin, uric acid and its derivatives, mannose and its derivatives, zinc and its derivatives (eg ZnO, ZnS0 ₄ ), selenium and its derivatives (eg

Selenium rriethionine), silibens and their derivatives (e.g., stilbene oxide, trans-stilbene oxide).

Suitable antioxidants are also compounds of the formulas A or B.

wherein

R ^{1 can be selected} from the group -C (O) CH ₃ , -CO ₂ R ³ , -C (O) NH ₂ and -C (O) N (R) ₂

X is O or NH, linear or branched alkyl having 1 to 30 C atoms,

R ^{3 is} linear or branched alkyl having 1 to 20 C atoms, R ^{4 are} each independently H or linear or branched alkyl having 1 to 8 C atoms, R ^{5 is} H, linear or branched alkyl having 1 to 8 C atoms or linear or branched alkoxy having 1 to 8 C atoms and R ^{6 is} linear or branched alkyl having 1 to 8 C atoms, preferably derivatives of 2- (4 Hydroxy-3,5-dimethoxybenzylidene) malonic acid and / or 2- (4-hydroxy-3,5-dimethoxybenzyl) -malonic acid, more preferably 2- (4-hydroxy-3,5-dimethoxybenzylidene) -malonic acid bis- (2-ethylhexyl) ester (eg Oxynex® ST Liquid) and / or 2- (4-hydroxy-3,5-dimethoxybenzyl) -malonic acid bis (2-ethylhexyl) ester (eg RonaCare® AP).

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 as active ingredients lecithin, L - (+) - ascorbyl palmitate and citric acid, 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-a-tocopherol, L (+) -

Ascorbyl palmitate, citric acid and lecithin (e.g., Oxynex® LM) or butylhydroxytoluene (BHT), L - (+) - ascorbyl palmitate and citric acid (e.g., Oxynex® 2004). Such antioxidants are with the

Compounds of the invention in such compositions usually in weight percent ratios ranging from 1000: 1 to 1: 1000, preferably used in weight percent ratios of 100: 1 to 1: 100.

Among the phenols which can be used according to the invention, the polyphenols, which occur in part as natural substances, are of particular interest for applications in the pharmaceutical, cosmetic or nutritional field. For example, the mainly as plant dyes Flavonoids or bioflavonoids often have an antioxidant potential. With effects of the substitution pattern of mono- and

Dihydroxy flavones deal with K. Lemanska, H. Szymusiak, B.

Tyrakowska, R. Zielinski, I.M.C.M. Rietjens; Current Topics in Biophysics 2000, 24 (2), 101-108. It is observed there that dihydroxyflavones having an OH group adjacent to the keto function or OH groups in the 3'4 'or 6,7 or 7,8 position have antioxidant properties, while other mono- and dihydroxyflavones are partially non-antioxidant

Have properties.

Quercetin (cyanidanol, cyanidolone 1522, meietin,

Sophoretine, ericin, 3,3 ', 4', 5,7-pentahydroxyflavone) as particular

effective antioxidant (e.g., CA Rice-Evans, N.J. Miller, G.A.

Paganga, Trends in Plant Science 1997, 2 (4), 152-159). K. Lemanska, H. Szymusiak, B. Tyrakowska, R. Zielinski, A.E.M.F. Soffers and I.M.C.M.

Rietjens (Free Radical BioIogy & Medicine 2001, 31 (7), 869-881 investigate the pH dependence of the antioxidant activity of hydroxyflavones, and quercetin shows the highest activity of the structures studied over the entire pH range.

Suitable anti-aging agents, especially for skin care

Preparations are preferably so-called compatible solutes. These are substances that are involved in the osmoregulation of

Plants or microorganisms are involved and can be isolated from these organisms. Under the generic term compatible solutes also the described in the German patent application DE-A-10133202 osmolytes are taken. Suitable osmolytes are, for example, the polyols, methylamine compounds and amino acids and in each case their precursors. As osmolytes are in the sense of the Germans

Patent application DE-A-10133202, in particular substances from the

Group of polyols, such as myo-inositol, mannitol or sorbitol and / or one or more of the following osmolytically effective substances: taurine, choline, betaine, phosphorylcholine, glycerophosphorylcholine, 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 z. B.

Compounds that are converted into osmolytes by metabolic steps.

Preferably according to the invention as compatible solute substances selected from the group consisting of Pyrimidincarbonsäuren (such as ectoine and hydroxyectoine), 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), β-mannosylglycerate (Firoin) , β-Mannosylglyceramide (Firoin-A) or / and di-mannosyl-di-inositol phosphate (DMIP) or an optical isomer, derivative, eg an acid, a salt or ester of these compounds or combinations thereof.

In particular, ectoine ((S) - 1, 4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid) and hydroxyectoine are among the pyrimidinecarboxylic acids

((S, S) -1, 4,5,6-tetrahydro-5-hydroxy-2-methyl-4-pyrimidinecarboxylic acid) and their derivatives.

Additional can be used as anti-aging agents Merck products such. 5,7-dihydroxy-2-methyl-chromone, marketed under the

 Tradenames RonaCare®Luremine, Ronacare®lsoquercetin,

Ronacare® tiliroside or Ronacare® cyclopeptide 5 can be used.

The preparations may also have one or more skin lightening

Active ingredients or synonym depigmentation agents or

Contain melanogenesis inhibitors. In principle, skin-lightening active ingredients can be all active ingredients known to the person skilled in the art. Examples of Compounds with skin-lightening activity are hydroquinone, kojic acid, arbutin, aloesin, niacinamide, azelaic acid, elagic acid,

Mulberry extract, magnesium ascorbyl phosphate,

Licorice root extract, Emblica, ascorbic acid or rucinol.

Preparations containing a combination of the compounds of the formula (I) with skin-lightening active ingredients can be, for example

act as a contrast reducing agent. According to the term the term

Contrast reduction that reduces uneven skin coloration and thus the contrast between stronger and less stained

 Skin is reduced. In this case, such an uneven skin coloration can be caused by an uneven pigmentation and / or a different distribution of the cornea. The combination of tanning substances whose mode of action is based on the Maillard reaction or Michael addition with melanogenesis-inhibiting substances has the effect that already hyperpigmented skin areas lose their high melanin concentration and the hue produced by the colorant on the skin surface permeates over a large area.

The preparations to be used may be further ingredients

Contain vitamins. Preference is given to vitamins and vitamin derivatives selected from vitamin A, vitamin A propionate, vitamin A palmitate, vitamin A acetate, retinol, vitamin B, thiamine hydrochloride hydrochloride (vitamin B, riboflavin (vitamin B ₂ ), nicotinamide, vitamin C (ascorbic acid), vitamin D, ergocalciferol (vitamin D ₂ ), vitamin E, DL-a-tocopherol, tocopherol-E-acetate, tocopherol hydrogen succinate, vitamin Ki, esculin (vitamin P active ingredient), thiamine (vitamin B ^, nicotinic acid (Niacin),

Pyridoxine, pyridoxal, pyridoxamine, (vitamin B ₆ ), pantothenic acid, biotin, folic acid and cobalamin (vitamin B ₁₂ ), 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 added to the flavonoid-containing premixes or preparations when applied cosmetically in the range of 0.01% to 5.0% by weight, based on the total weight. nutritional

Applications are based on the recommended vitamin requirement.

The described retinoids are also effective anti-cellulite agents. Another well-known anti-cellulite drug is caffeine. The present invention also provides a process for

Preparation of a preparation as described above, characterized

in that at least one compound of the formula (I) is mixed with a carrier suitable for topical preparations and optionally with excipients and / or fillers. Suitable excipients and auxiliaries or fillers are described in detail in the following part.

The said constituents of the preparation can be incorporated in the usual way, by means of techniques which are well known to the person skilled in the art.

The cosmetic and dermatological preparations can be in various forms. So they can z. For example, a solution, an anhydrous preparation, an emulsion or microemulsion of the water-in-oil (W / O) type or of the oil-in-water (O / W) type, a multiple emulsion, for example of the water-in-water type. Oil-in-water (W / OW) or O / W / O, a gel, a solid stick, an ointment or even an aerosol. Preference is given to emulsions. O / W emulsins are especially preferred. Emulsions, W / O emulsions and O / W emulsions are available in the usual way.

As an application form of the preparations to be used, e.g.

called: solutions, suspensions, emulsions, PIT emulsions, pastes, Ointments, gels, creams, lotions, powders, soaps, surfactant-containing

Cleaning preparations, oils, aerosols, plasters, envelopes, dressings and sprays. Preferred excipients come from the group of preservatives, stabilizers, solubilizers, colorants, odor improvers.

Ointments, pastes, creams and gels may contain the usual excipients suitable for topical administration, e.g. animal and vegetable fats, waxes, paraffins, starch, tragacanth,

 Cellulose derivatives, polyethylene glycols, silicones, bentonites, silicic acid, talc and zinc oxide or mixtures of these substances.

Powders and sprays may contain the usual carriers, e.g.

Lactose, talc, silicic acid, aluminum hydroxide, calcium silicate and polyamide powder or mixtures of these substances. Sprays may additionally contain the usual volatilized, liquefied propellants, e.g.

Chlorofluorocarbons, propane / butane or dimethyl ether. Also, compressed air is advantageous to use.

Solutions and emulsions may be 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-butylglycol, oils, especially cottonseed oil, peanut oil, corn oil, olive oil, castor oil and sesame oil,

 Glycerin fatty acid esters, polyethylene glycols and fatty acid esters of

Sorbitans or mixtures of these substances.

A preferred solubilizer in general is 2-isopropyl-5-methylcyclohexanecarbonyl-D-alanine methyl ester. Suspensions may be the usual carriers such as liquid

Diluent, e.g. Water, ethanol or propylene glycol,

Suspending agent, 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 may contain the usual excipients such as alkali metal salts of fatty acids, salts of fatty acid halides, fatty acid protein hydrolysates, isothionates, lanolin, fatty alcohol, vegetable oils, plant extracts, glycerol, sugars or mixtures of these substances.

Surfactant-containing cleaning products, the usual carriers such as salts of fatty alcohol sulfates, fatty alcohol ether sulfates,

Sulfosuccinic monoesters, fatty acid protein hydrolysates, isothionates, imidazolinium derivatives, methyl taurates, sarcosinates,

Fatty acid amide ether sulfates, alkylamido betaines, fatty alcohols,

Fatty acid diethanolamides, vegetable and synthetic oils, lanolin derivatives, ethoxylated glycerol fatty acid esters or mixtures of these substances.

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

Vegetable oils and oily vegetable extracts, paraffin oils, lanolin oils or mixtures of these substances.

Other typical cosmetic applications include lipsticks, lip balms, powder, emulsion and wax make-up as well

Sunscreen, pre-sun and after-sun preparations.

The preferred preparation forms include, in particular, emulsions. Emulsions are advantageous and contain z. As mentioned fats, oils, waxes and other fatty substances, and water and an emulsifier, as it is commonly used for such a type of preparation.

The lipid phase can be selected advantageously from the following

Group of substances:

 - mineral oils, mineral waxes

 - Oils such as triglycerides of capric or caprylic acid, also natural oils such. Castor oil;

 Fats, waxes and other natural and synthetic fats, preferably esters of fatty acids with lower C number alcohols, e.g. with isopropanol, propylene glycol or glycerol, or esters of

 Fatty alcohols with lower 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 in the context of the present invention is advantageously selected from the group of esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids having a chain length of 3 to 30 C atoms and saturated and / or unsaturated,

branched and / or unbranched alcohols of 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 of a chain length of 3 to 30 C atoms. Such ester oils can then be advantageously selected from the group

Isopropyl myristate, isopropyl palmitate, isopropyl stearate, isopropyl oleate, n-butyl stearate, n-hexyl laurate, n-decyl oleate, isooctyl stearate, isononyl stearate, isononyl isononanoate, 2-ethylhexyl palmitate, 2-ethylhexyl laurate, 2

Hexadecyl stearate, 2-octyl dodecyl palmitate, oleyl oleate, oleyl erucate, Erucyl oleate, erucyl erucate and synthetic, semi-synthetic and natural mixtures of such esters, eg. B. jojoba oil.

Furthermore, the oil phase can be advantageously selected from the group of branched and unbranched hydrocarbons and waxes, the

Silicone oils, the dialkyl ethers, the group of saturated or unsaturated, branched or unbranched alcohols, and the fatty acid triglycerides, namely the triglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids having a chain length of 8 to 24, in particular 12-18 C atoms. The fatty acid triglycerides can be selected, for example, advantageously from the group of synthetic, semi-synthetic and natural oils, for. As olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palm oil, coconut oil, palm kernel oil and the like.

Any mixtures of such oil and wax components are also advantageous to use in the context of the present invention. It may also be advantageous, if appropriate, to use waxes, for example cetyl palmitate, as the sole lipid component of the oil phase.

The aqueous phase of the preparations to be used contains

optionally advantageous alcohols, diols or polyols of low C number, and their ethers, preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, -monoethyl or -monobutylether,

 Diethylene glycol monomethyl or monoethyl ether and analogous products, furthermore low e number alcohols, e.g. For example, ethanol, isopropanol, 1, 2 propanediol, glycerol, and in particular one or more thickeners, which or which can be advantageously selected from the group

Silica, aluminum silicates, polysaccharides or their derivatives, for example hyaluronic acid, xanthan gum, hydroxypropylmethylcellulose, particularly advantageously from the group of polyacrylates, preferably a polyacrylate the group of so-called carbopols, for example Carbopols of types 980, 981, 1382, 2984, 5984, in each case individually or in combination.

In particular, mixtures of the abovementioned solvents are used. For alcoholic solvents, water can be another

Be part of it.

In a preferred embodiment, the preparations to be used contain hydrophilic surfactants. The hydrophilic surfactants are preferably selected from the group of alkylglucosides, acyl lactylates, betaines and cocoamphoacetates.

As emulsifiers, for example, the known W / O and O / W emulsifiers can be used. It is advantageous to use other conventional co-emulsifiers in the preferred O / W emulsions.

For example, O / W emulsifiers are selected as co-emulsifiers, principally from the group of substances with HLB values of 11-16, very particularly advantageously with HLB values of 14.5-15.5, provided that 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 may be those of

Emulsifiers also lower or above. It is advantageous to include the fatty alcohol ethoxylates from the group of

ethoxylated stearyl alcohols, cetyl alcohols, cetylstearyl alcohols

(Cetearyl alcohols).

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 glycol (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 (9) oleate,

Polyethylene glycol (20) oleate. As the ethoxylated alkyl ether carboxylic acid or its salt, the sodium laureth-11-carboxylate can be advantageously used. As the alkyl ether sulfate, sodium laureth-4 sulfate can be advantageously used. As the ethoxylated cholesterol derivative, polyethylene glycol (30) cholesteryl ether can be advantageously used. Also polyethylene glycol (25) soybean oil has been proven. As ethoxylated triglycerides, the polyethylene glycol (60) Evening Primrose Glycerides can advantageously be used (Evening Primrose = evening primrose).

It is furthermore advantageous to use the polyethylene glycol glycerol fatty acid esters from the group consisting of polyethylene glycol (20) glyceryl laurate,

 Polyethylene glycol (21) glyceryl laurate, polyethylene glycol (22) glyceryl laurate,

Polyethylene glycol (23) glyceryl laurate,

 Polyethylene glycol (6) glycerylcaprat / cprinat,

Polyethylene glycol (20) glyceryl oleate, polyethylene glycol (20) glyceryl isostearate, polyethylene glycol (18) glyceryl oleate (cocoate). It is also beneficial to have the sorbitan esters from the group

Polyethylene glycol (20) sorbitan monolaurate,

Polyethylene glycol (20) sorbitan monostearate,

Polyethylene glycol (20) sorbitan monoisostearate,

Polyethylene glycol (20) sorbitan monopalmitate,

 Polyethylene glycol (20) to choose sorbitan monooleate.

As optional, but according to the invention optionally advantageous W / O emulsifiers can be used:

Fatty alcohols having 8 to 30 carbon atoms, monoglycerol esters of saturated and / or unsaturated, branched and / or unbranched

Alkanecarboxylic acids having a chain length of 8 to 24, in particular 12-18 C atoms, diglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids of a chain length of 8 to 24, in particular 12-18 C ^-1 atoms, monoglycerol ethers saturated and / or unsaturated , branched and / or unbranched alcohols of a

Chain length of 8 to 24, in particular 12- 8 C-atoms, diglycerol ethers of saturated and / or unsaturated, branched and / or unbranched alcohols of a chain length of 8 to 24, in particular 12-18 C atoms, propylene glycol esters of saturated and / or unsaturated, branched and or unbranched alkanecarboxylic acids having a chain length of 8 to 24, in particular 12-18 carbon atoms and sorbitan esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids having a chain length of 8 to 24, in particular 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, polyethylene glycol (2) stearyl ether (steareth-2),

Glyceryl monolaurate, glyceryl monocaprinate, glyceryl monocaprylate or PEG-30 dipolyhydroxystearate.

The preparation may contain cosmetic adjuvants which are commonly used in this type of preparation, e.g.

Thickeners, emollients, moisturizers,

surfactants, emulsifiers, preservatives, antifoaming agents, perfumes, waxes, lanolin, propellants, dyes and / or pigments, and other ingredients commonly used in cosmetics.

As dispersion or solubilizing agent, an oil, wax or other fatty substance, a low monoalcohol or a low

Use polyol or mixtures thereof. Particularly preferred monoalcohols or polyols include ethanol, i-propanol, propylene glycol, glycerine and sorbitol. A preferred embodiment of the invention is an emulsion which is present as a protective cream or milk and contains, for example, fatty alcohols, fatty acids, fatty acid esters, in particular triglycerides of fatty acids, lanolin, natural and synthetic oils or waxes and emulsifiers in the presence of water.

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

Fatty acid esters, in particular triglycerides of fatty acids, or oily 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 may also be in the form of an alcoholic gel comprising one or more lower alcohols or polyols, such as ethanol, propylene glycol or glycerin, 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 formulated as an aerosol, the usual blowing agents are generally used, such as alkanes, fluoroalkanes and chlorofluoroalkanes, preferably alkanes.

Another object of the present invention are compounds of the formula (I)

where R 1 is a branched or unbranched alkyl radical having 1 to 20 C atoms, a branched or unbranched alkenyl radical having 2 to 20 C atoms or a branched or unbranched alkynyl radical having 2 to 20 C atoms,

wherein one or more non-adjacent and not directly to the O atom of formula (I) adjacent CH ₂ groups may be replaced by C = O or -O-,

where these radicals may be substituted by one or more OH groups, one or more cyclic alkyl radicals having from 3 to 8 carbon atoms and / or by one or more aromatic ring systems having from 5 to 6 carbon atoms, where the. or more aromatic ring systems having one or more groups selected from -OH, -OR, -NR ₂ , -CN, -COOR and -COOR 'may be substituted; where R stands independently for each occurrence

branched or unbranched Aikylrest having 1 to 20 carbon atoms; and wherein R 'is an aromatic ring system having 5 or 6 C atoms; and wherein the following compounds are excluded:

 O O

The preferred embodiments of the radicals R1 and R of the compounds according to the invention are defined here as described above.

Particular preference is given to compounds of the formula (I), which are characterized in that the compounds are selected from the compounds of the formulas (Ib) to (Ik)

Another object of the present invention is also a process for preparing a compound of formula (I) as defined above, characterized in that 2,5-diethoxy-2,5-bis (hydroxymethyl) -1, 4-dioxane with a compound of the formula R 1 -X and then acid-hydrolyzed, wherein R ₁ is as defined above and X is Cl, Br, I, OSO ₂ CH ₃ (O-mesyl) or OSO ₂ C ₆ H ₄ CH ₃ (O-tosyl).

Even without further statements, it is assumed that a person skilled in the art can make the most of the above description. The preferred embodiments and examples are therefore merely illustrative and in no way limiting in any way

To understand the revelation. The complete disclosure of all applications and publications cited above and below are incorporated by reference into this application.

Other important features and advantages of the invention will become apparent from the dependent claims and from the examples.

Preferred embodiments of the invention are illustrated in the examples and will be explained in more detail in the following description, without limiting the scope of the present invention.

Examples:

Example 1a: Synthesis of compound (Ia):

 Synthesis of 2,5-di-ethoxy-2,5-bis (hydroxymethyl) -1,4-dioxane:

The synthesis of 2,5-diethoxy-2,5-bis (hydroxymethyl) [1,4] dioxane is as disclosed in Jung et al., Journal of Organic Chemistry, 1994, 7182: In an inerted 1 liter three-necked flask in 500 ml of anhydrous ethanol 3 ml conc. Sulfuric acid (56 mmol) and 105 ml

Triethyl orthoformate (631 mmol). The solution is allowed to stand for 30 min Heated to reflux, then cooled to 0-4 ° C and every 12 hours dimer dihydroxyacetone in a total of 6 portions (6 x 4.23 g = 25.4 g, 141 mmol) was added. After a further 24 h at 0-4 ° C, 19 g of anhydrous sodium bicarbonate (226 mmol) are added and stirred for a further 30 min. The reaction solution is then filtered through Celite / silica gel at room temperature and the filter cake is washed with 100 ml of ethyl acetate. After removal of the solvent in vacuo, the residue is taken up in 100 ml of ethyl acetate and distilled again in vacuo. By adding 400 ml of hexane, a white solid is formed which is filtered and washed with 100 ml of hexane. This gives 32.3 g of product (97%) as a white solid.

Synthesis of 2,5-bis (benzyloxymethyl) -2,5-diethoxy-1,4-dioxane:

20 g of 2,5-di-ethoxy-2,5-bis (hydroxymethyl) -1,4-dioxane (85 mmol) are dissolved in 106 ml of toluene and heated to 45 ° C. Then 16.8 g

Potassium hydroxide (255 mmol, 3 eq.) Was added and 20, 1 ml of benzylbromide (16 mmol, 2 eq.) Was added slowly dropwise. Subsequently, it is refluxed for 4 hours. After cooling to 80 ° C, 100 ml of water are added and heated again for 16 h under reflux. After cooling to room temperature, the organic phase is separated and the

Solvent removed in vacuo. It is then recrystallized from 31 g of ethanol in the cold. This gives 18.4 g (52%) of product as colorless crystals.

¹ H-NMR (CDCl ₃ ): δ = 1, 21 (t, 2x CH ₃ ), 3.39 (d, CAY ₂ -OBn, J = 10.9 Hz), 3.53 (d, CH ₂ - OBn, J = 10.9 Hz), 3.59 (d, 2xCH ₂ -CH ₃ ), 3.64 (d, C-CH ₂ -0, J = 11, 7), 3.84 (d, C -CH ₂ -O, J = 1 1, 7), 4.53 (d, CH ₂ -Ph, J = 12.1 Hz), 4.59 (d, CH ₂ -Ph, J = 12.1 Hz ), 7.27-7.45 (m, 5xAr-H) ppm.

Synthesis of 1-benzyloxy-3-hydroxy-propan-2-one (Ia):

13 g of 2,5-bis (benzyloxymethyl) -2,5-diethoxy-1,4-dioxane (31 mmol) are dissolved in 62 ml of THF and a mixture of 8.7 ml of 95% sulfuric acid slowly added dropwise with 31 ml of water, keeping the internal temperature at 40 ° C. After 4 hours of reaction time, the biphasic

Reaction solution with 100 ml MTBE and the organic phase separated. The solvent is removed in vacuo and the residue recrystallized from 50 ml of toluene / heptane 2/1. This gives 7.2 g (64%) of product (Ia) as a solidifying oil. H-NMR (DMSO-de): δ = 3.39 (t, OH), 4.17 (d, CH ₂ -OH, J = 5.9 Hz), 4.30 (s, CH ₂ -OCH ₂ Ph), 4.54 (s, Ph-CH ₂ O), 7.27-7.45 (m, 5xAr-H) ppm.

Example 1b: Synthesis of compound (Ic), n = 7:

 Synthesis of 2, 5-Diethoxy-2,5-bis-heptyloxymethyl- [1,4] dioxane:

20 g of 2,5-di-ethoxy-2,5-bis (hydroxymethyl) -1,4-dioxane (85 mmol) are dissolved in 170 ml of toluene and heated to 45 ° C. Then 16.8 g

Potassium hydroxide (255 mmol, 3 eq.) Was added and 40 ml of 1-bromoheptane (255 mmol, 3 eq.) Were slowly added dropwise. Subsequently, it is refluxed for 4 hours. After cooling to 80 ° C, 300 ml of water are added. After cooling to room temperature, the organic phase is separated and the solvent removed in vacuo.

It is then purified by column chromatography (heptane / MTBE 1/1). This gives 27.11 g (74%) of product as a light yellow oil.

¹ H-NMR (500 MHz, CDCl ₃ ): δ = 0.88 (t, 2x CH ₃ ), 1.18 (t, CH), 1.21-1.36 (m, 14xCH), 1.42 (m, 2x CH) , 1.56 (m, 2xCH), 1.85 (q, 2xCH), 3.32-3.71 (m, 7xCH), 3.77 (d, C-CH ₂ -O, J = 13.86), 3.85 (d, C-CH ₂ -O, J = 13.86) ppm.

¹³ C-NMR (75 MHz, CDCl ₃ ): δ = 14.03, 15.50, 22.62, 26.02, 26.08, 28.17, 28.45, 29.03, 29.1 1, 29.46, 29.53, 31.66, 31.83, 31.90, 32.88, 33.99, 55.64, 56.40 , 56.60, 61.47, 63.92, 68.01, 68.74, 70.64, 71.52, 71.69, 71.91, 94.93, 98.00 ppm. Synthesis of 1-heptyloxy-3-hydroxy-propan-2-one (Ic n = 7):

19 g of 2,5-diethoxy-2,5-bis-heptyloxymethyl [1, 4] dioxane (43 mmol) are dissolved in 120 ml of THF and slowly added dropwise a mixture of 13 ml of 95% sulfuric acid with 61 ml of water, wherein the internal temperature is kept at 40 ° C. After a reaction time of 48 hours, the biphasic reaction solution is admixed with 122 ml of MTBE and the organic phase is separated off. The solvent is removed in vacuo and the residue is purified by column chromatography (heptane / MTBE 1/1). This gives 3.82 g (23%) of product (Ic n = 7) as an oil.

¹ H-NMR (DMSO-de): δ = 0.89 (t, 2xCH _3), 1.28 (m, 8xCH), 1.60 (m, 2xCH), 3:45 (m, 3xCH) ppm.

Example 2: Browning Experiment (Liquid Skin Model):

 1 mmol of the self-tanning substance to be tested are mixed with 146 mg of DL-lysine (1 mmol) in 94 ml of ethylene glycol and 6 ml of water

(Potassium hydrogen phthalate-buffered to pH = 7) and dissolved for 24 hrs.

stirred (= Liquid Skin Model). The documentation of the kinetics is done via photos. After 24 h, the color values (L * a * b * system) of the solution are measured by UV-Vis spectrometer (Varian Cary-50) in order to be able to assess the effect on the skin tone.

Test substances:

Kinetics: Both MHDE and MBDE show a faster tanning reaction than DHA. An optical evaluation resulted in a doubling of the speed.

Lab values after 24 hours:

The Lab values show that MHDE (Ic) shows a darker coloration (lower L * value) compared to DHA and has more neutral color values (a ^* and b ^* values close to 0). MBDE (la) shows a strong shift to a redder hue (higher a * than DHA), creating a more natural skin tone. The combination of MBDE (Ia) with DHA also shows the positive effect on hue even at low levels of MBDE. Furthermore, the expression of the red clay is linear to the amount of MBDE used, which allows a precise adaptation of the desired skin tone to the specific needs of the user.

MEHDE (Ib) shows lighter color (greater L ^* value) and more neutral color values (a * near 0 and b * smaller) compared to DHA.

MCHMDE (Id) shows a strong shift to a yellower hue (higher b ^* than DHA) and a slightly reduced red tint. solubilities:

 In contrast to DHA, the DHA ethers show good solubility in cosmetic oils (Finsolv TN as an example):

DHA: «0.1%

MBDE: 0.24%

MEHDE: 2.25%

MEASURE: 0.97%. Example 3a: O / W tanning cream

 Production method:

First, phase A is heated to 75 ° C and phase B to 80 ° C. Thereafter, phase B is slowly added with stirring to phase A and stirred until a homogeneous mixture is formed. After Homogenization is the formulation until it cools down

Room temperature stirred. The pH is adjusted with sodium hydroxide solution or

Citric acid adjusted to pH = 6.5.

Sources:

 (1) Sasol Germany GmbH (2) Cognis GmbH (3) BASF AG

(4) Degussa-Goldschmidt AG (5) Merck KGaA / Rona®

Example 3b: O / W Tanning Cream

 Production method:

First, phase A is heated to 75 ° C and phase B to 80 ° C. Thereafter, phase B is slowly added with stirring to phase A and stirred until a homogeneous mixture is formed. After Homogenization and cooling of the emulsion, the phase C is added at 40 ° C. Subsequently, the formulation is stirred until it cools to room temperature. The pH is adjusted with sodium hydroxide solution or

Citric acid adjusted to pH = 5.5.

Sources:

 (1) Sasol Germany GmbH (2) Cognis GmbH (3) BASF AG

(4) Degussa-Goldschmidt AG (5) Merck KGaA / Rona®

Example 4a: O / W tanning cream

 Ingredients / Reference INCI [trade name source%]

A

 Tego Care 50 (1) GLYCERYL STEARATE, 8.00

 STEARETH-25 CETETH-20,

 STEARYL ALCOHOL

 Miglyol 812 N (2) CAPRYLIC / CAPRIC 3.00

 TRIGLYCERIDES

 Isopropyl myristate (3) ISOPROPYL MYRISTATE 2.00

Paraffin liquid (4) PARAFFINUM LIQUIDUM 12.00

 (MINERAL OIL)

 Paraffin (4) PARAFFIN 2.00

Propyl 4- (4) propyl paraben 0.15 hydroxybenzoate

 MBDE (5) MONOBENZYL- 5.00

 DIHYDROXYACETONETHER

B

 1, 2-propanediol (4) PROPYLENE GLYCOL 4.00

Sorbitol F liquid (4) SORBITOL 2.00

Methyl 4- (4) METHYLPARABENE 0.05 hydroxybenzoate

 Water, AQUA (WATER) 61.30 demineralized

C

 Fragrance (q.s.) PERFUME 0.50

Total 100.00 Production method:

 First, phases A and B are heated separately to 75 ° C. Thereafter, phase A is slowly added to phase B with gentle stirring. It is homogenized at 65 ° C for one minute. The mixture is then cooled with stirring to 35 ° C and the phase C added with stirring, and further cooled. The pH is adjusted with sodium hydroxide solution or

Citric acid adjusted to pH = 5.5.

Sources:

 (1) Degussa-Goldschmidt AG (2) Sasol Germany GmbH

(3) Cognis GmbH (4) Merck KGaA / Rona®

Example 4b: O / W tanning cream

 Ingredients / Reference INCI [trade name source%]

A

 Tego Care 150 (1) GLYCERYL STEARATE, 8.00

 STEARETH-25 CETETH-20,

 STEARYL ALCOHOL

 Miglyol 812 N (2) CAPRYLIC / CAPRIC 3.00

 TRIGLYCERIDES

 Isopropyl myristate (3) ISOPROPYL MYRISTATE 2.00

Paraffin liquid (4) PARAFFINUM LIQUIDUM 12.00

 (MINERAL OIL)

 Paraffin (4) PARAFFIN 2.00

Propyl 4- (4) propyl paraben 0.15 hydroxybenzoate

 MBDE (5) MONOBENZYL- 2.00

 DIHYDROXYACETONETHER

B

 1, 2-propanediol (4) PROPYLENE GLYCOL 4.00

Sorbitol F liquid (4) SORBITOL 2.00

Methyl 4- (4) METHYLPARABENE 0.05 hydroxybenzoate

 Water, AQUA (WATER) 47.50 demineralized

C Water, AQUA (WATER) 11.80 demineralized

 Dihydroxyacetone (4) DIHYDROXYACETONE 5.00

D

 Fragrance (q.s.) PERFUME 0.50

Total 100.00

Production method:

 First, phases A and B are heated separately to 75 ° C. Thereafter, phase A is slowly added to phase B with gentle stirring. It is homogenized at 65 ° C for one minute. The mixture is then cooled with stirring to 40 ° C and the phase C is added. It is then cooled to 35 ° C and the phase D added with stirring, and further cooled. The pH is adjusted to pH = 6.0 using sodium hydroxide solution or citric acid.

Sources:

 (1) Degussa-Goldschmidt AG (2) Sasol Germany GmbH

 (3) Cognis GmbH (4) Merck KGaA / Rona®

Example 5a: O / W Tanning Cream

 Ingredients / Reference INCI [Trade name source%]

A

 Tego Care 50 0) GLYCERYL STEARATE, 8.00

 STEARETH-25, CETETH-20,

 STEARYL ALCOHOL

 La Nice O (2) CETEARYL ALCOHOL 1.50

Luvitol EHO (3) CETEARYL OCTANOATE 5.00

Miglyol 812 N (4) CAPRYLIC / CAPRIC 5.00

 TRIGLYCERIDES

 Paraffin liquid (5) PARAFFINUM LIQUIDUM 3.00

 (MINERAL OIL)

 AbilWax 2434 (1) STEAROXY DIMETICONE 1.60

Dow Corning 200 (6) DIMETICONE 0.50 Fluid (350 es)

Propyl-4- (5) PROPYLL PARKS 0.05 hydroxybenzoate

B

 1, 2-Propanediol (5) PROPYLENE GLYCOL 3.00

Methyl 4- (5) METHYLPARABENES 0.15 hydroxybenzoate

 Water, AQUA (WATER) 52.20 demineralized

C

MEHDE (5) MONOETHYLHEXYL- 5.00

 DIHYDROXYACETONETHER

 Probiol L 05018 (7) AQUA, ALCOHOL DENATE, 5:00 (empty liposomes) LELCITHIN, GLYCERINE,

 DISODIUM PHOSPHATES

 Water, AQUA (WATER) demineralized 10.00

Total 100.00 Production process:

 First, phases A and B are heated to 80 ° C. Thereafter, phase B is slowly added with stirring to phase A and homogenized. It is then cooled and the phase C at 40 ° C was added. Sources:

 (1) Degussa-Goldschmidt AG (2) Cognis GmbH (3) BASF AG (4) Sasol Germany GmbH (5) Merck KGaA / Rona® (6) Dow Corning (7) Kuhs GmbH & Co. KG

Example 5b: O / W Tanning Cream

 Ingredients / Reference INCI [trade name source%]

A

 Tego Care 150 (1) GLYCERYL STEARATE, 8.00

 STEARETH-25, CETETH-20,

 STEARYL ALCOHOL

 Lanette O (2) CETEARYL ALCOHOL 1.50

Luvitol EHO (3) CETEARYL OCTANOATE 5.00

Miglyol 812 N (4) CAPRYLIC / CAPRIC 5.00 TRIGLYCERIDES

 Paraffin liquid (5) PARAFFINUM LIQUIDUM 3.00

 (MINERAL OIL)

 AbilWax 2434 (1) STEAROXY DIMETHICONE 1.60

Dow Corning 200 (6) DIMETICONE 0.50 Fluid (350 es)

 Propyl 4- (5) PROPYLL PARTS 0.05 hydroxybenzoate

 MBDE (5) MONOBENZYL- 1.00

 DIHYDROXYACETONETHER

B

 1, 2-Propanediol (5) PROPYLENE GLYCOL 3.00

Methyl 4- (5) METHYLPARABENES 0.15 hydroxybenzoate

 Water, AQUA (WATER) 51.20 demineralized

C

 Dihydroxyacetone (5) DIHYDROXYACETONE 5.00

Probiol L 05018 (7) AQUA, ALCOHOL DENATE, 5.00 (empty LELCITHIN, GLYCERINE,

 Liposomes) DISODIUM PHOSPHATES

 Water, AQUA (WATER) demineralized 10.00

Total 100.00

Production method:

 First, phases A and B are heated to 80 ° C. Thereafter, phase B is slowly added with stirring to phase A and homogenized. It is then cooled and the phase C at 40 ° C was added.

Sources:

(1) Degussa-Goldschmidt AG (2) Cognis GmbH (3) BASF AG (4) Sasol Germany GmbH (5) Merck KGaA / Rona® (6) Dow Corning (7) Kuhs GmbH & Co. KG Example 6a: O / W tanning lotion

 Ingredients / Reference INCI [trade name source%]

A

 Montanov 68 (1) CETEARYL ALCOHOL, 4.00

 CETEARYL GLUCOSIDE

 Span 60 (2) SORBITAN STEARATE 1.50

La Nice O (3) CETEARYL ALCOHOL 1.00

Cosmacol ELI (4) C12-13 ALIKYL LACTATE 2.00

Arimol HD (2) ISOHEXADECANE 1.50

Paraffin highly (5) PARAFFINUM LIQUIDUM 3.50 liquid (MINERAL OIL)

 Dow Corning (6) CYCLOMETHICONE, 2.00 9050 Silicone DIMETHICONE

 Elastomer Blend CROSSPOLYMER

RonaCare ^® (5) Tocopheryl Acetate 00:50 tocopherol

 Acetate

 Propyl 4- (5) PROPYLPARABENE 0.05 hydroxybenzoate

 MHDE (5) MONOHEPTYL- 2.50

 D Y H YDROXYAC ETO N ETH E R

B

RonaCare ^® (5) ECTOIN 00:50 ectoine

 Glycerin, (5) GLYCERINE 2.00 anhydrous

 Water, demineralized AQUA (WATER) 60.90

 Methyl 4- (5) METHYLPARABENES 0.15 hydroxybenzoate

C

 Rhodicare S (7) XANTHAN GUM 0.20

D

 Probiol L 050 8 (8) AQUA, ALCOHOL DENAT, 5.00

(Empty LECITHIN, GLYCERINE,

 Liposomes) DISODIUM PHOSPHATES

Water, AQUA (WATER) demineralized 10.00 e

 Fragrance (9) PERFUME 0.20 Cucumber

Total 100.00

Production method:

 First, phases A and B are mixed separately and heated to 75 ° C. Thereafter, phase C is added to phase B and added to phase A with stirring. It is homogenized. It is then cooled with stirring and the phases D and E at 40 ° C was added.

Sources:

 (1) Seppic (2) Uniqema (3) Cognis GmbH

(4) Condea Chinica D.A.C.S.p.A. (5) Merck KGaA / Rona®

(6) Dow Coming (7) Rhodia GmbH (8) Kuhs GmbH & Co. KG (9) Drom

Example 6b: O / W tanning lotion

 Ingredients / Reference INCI [trade name source%]

A

 Montanov 68 (1) CETEARYL ALCOHOL, 4.00

 CETEARYL GLUCOSIDE

 Span 60 (2) SORBITAN STEARATE 1.50

Lanette 0 (3) CETEARYL ALCOHOL 1.00

Cosmacol ELI (4) C12-13 ALIKYL LACTATE 2.00

Arimol HD (2) ISOHEXADECANE 1.50

Paraffin highly (5) PARAFFINUM LIQUIDUM 3.50 liquid (MINERAL OIL)

 Dow Corning (6) CYCLOMETHICONE, 2.00 9050 Silicone DIMETICONE

 Elastomer Blend CROSSPOLYMER

RonaCare ^® (5) Tocopheryl Acetate 00:50 tocopherol

 Acetate

 Propyl 4- (5) PROPYLPARABENE 0.05 hydroxybenzoate

MEHDE (5) MONOETHYLHEXYL- 5.00 DIHYDROXYACETONETHER

B

RonaCare ^® (5) ECTOIN 00:50 ectoine

 Glycerin, (5) GLYCERINE 2.00 anhydrous

 Water, demineralized AQUA (WATER) 60.90

 Methyl 4- (5) METHYLPARABENES 0.15 hydroxybenzoate

C

 Rhodicare S (7) XANTHAN GUM 0.20

D

 Probiol L 05018 (8) AQUA, ALCOHOL DENAT, 5.00

(Empty LECITHIN, GLYCERINE,

 Liposomes) DISODIUM PHOSPHATES

 Water, AQUA (WATER) demineralized 10.00

e

 Fragrance (9) PERFUME 0.20 Cucumber

Total 100.00

Production method:

 First, phases A and B are mixed separately and heated to 75 ° C. Thereafter, phase C is added to phase B and added to phase A with stirring. It is homogenized. It is then cooled with stirring and the phases D and E at 40 ° C was added. The pH is adjusted to pH = 6.0 using sodium hydroxide solution or citric acid.

Sources:

 (1) Seppic (2) Uniqema (3) Cognis GmbH

 (4) Condea Chinica D.A.C.S.p.A. (5) Merck KGaA / Rona®

(6) Dow Corning (7) Rhodia GmbH (8) Kuhs GmbH & Co. KG (9) Drom Example 7a: mild transparent W / O tanning lotion

 Production method:

 First, phase B is dissolved and then it is given to phase A. The pH is adjusted to pH = 6.0 using sodium hydroxide solution or citric acid.

Sources:

 (1) Dow Coming (2) Merck KGaA / Rona®

Example 7b: mild transparent W / O tanning lotion

 Ingredients / Reference INCI [trade name source%]

A

 Dow Corning (1) CYCLOMETHICONE, 23.60 3225 C DIMETHICONE COPOLYOL

 Propyl 4- (2) PROPYLPARABENE 0.05 hydroxybenzoate

B MHDE (2) MONOHEPTYL- 5.00

 DIHYDROXYACETONETHER

 Methyl 4- (2) METHYLPARABENES 0.15 hydroxybenzoate

 1, 2-propanediol (2) PROPYLENE GLYCOL 35.90

Water, AQUA (WATER) 35.30 demineralized

Total 100.00

Production method:

 First, phase B is dissolved and then it is given to phase A.

Sources:

 (1) Dow Coming (2) Merck KGaA / Rona®

Example 8a: W / O tanning lotion

 Ingredients / Reference INCI [trade name source%]

A

 Abil EM 97 (1) BIS-PEG / PPG- 4/14 1.50

 dimeticones,

 Cyclopentasiloxane

 Abil EM 90 (1) CETYL PEG / PPG-10/1 1.30

 dimeticones

 Ceraphyl 368 (2) ETHYLHEXYL PALMITATE 2.00

Tegosoft DEC (1) DIETHYLHEXYL 5.00

 CARBONATE

 Dow Corning 345 (3) CYCLOMETHICONE 13.00

Dow Corning (3) DIMETICONE 3.00 9041 Silicone CROSSPOLYMER,

 Elastomer blend DIMETICONE

 Fragrance (4) PERFUME 0.30 Babylon

 MEHDE (5) MONOETHYLHEXYL- 2.00

 DIHYDROXYACETONETHER

B

 1, 2-Propanediol (5) PROPYLENE GLYCOL 20.00

Glycerine, (5) GLYCERINE 3.00 anhydrous

 Magnesium Sulph (5) MAGNESIUM SULPHATE 2.00 at heptahydrate

 Phenonip (6) PHENOXYETHANOL, 1.00

 butyl paraben,

 ethyl paraben,

 pROPYLPARABEN,

 METHYLPARABEN

 Ethanol 96% (5) ALCOHOL 8.00

Dihydroxyacetone (5) D I H Y D ROXYAC ETO N E 3.00

Water, AQUA (WATER) 34.90 demineralized

Total 100.00

Production method:

 First, the magnesium sulfate heptahydrate is dissolved in the water of phase B. Then the remaining components of phase B are added. Phase B is slowly added to Phase A with stirring. It is quickly stirred for a further 2 minutes and homogenized. The pH is adjusted to pH = 5.5 with sodium hydroxide solution or citric acid.

Sources:

 (1) Degussa-Goldschmidt AG (2) ISP Global Technologies

(3) Dow Coming (4) Drom (5) Merck KGaA / Rona®

(6) Nipa Laboratories GmbH

Example 8b: W / O tanning lotion

 Ingredients / Reference INCI [trade name source%]

A

 Abil EM 97 (1) BIS-PEG / PPG- 4/14 1.50

 dimeticones,

 Cyclopentasiloxane

 Abil EM 90 (1) CETYL PEG / PPG-10/1 1.30

 dimeticones

 Ceraphyl 368 (2) ETHYLHEXYL PALMITATE 2.00

Tegosoft DEC (1) DIETHYLHEXYL 5.00

CARBONATE Dow Corning 345 (3) CYCLOMETHICONE 13.00

Dow Corning (3) DIMETHICONE 3.00 9041 Silicone CROSSPOLYMER,

 Elastomer blend DIMETHICONE

 Fragrance (4) PERFUME 0.30 Babylon

 MHDE (5) MONOHEPTYL- 1.00

 DIHYDROXYACETONETHER

B

 1, 2-Propanediol (5) PROPYLENE GLYCOL 20.00

Glycerin, (5) GLYCERINE 3.00 anhydrous

 Magnesium (5) MAGNESIUM SULPHATE 2.00 sulphate

 heptahydrate

 Phenonip (6) PHENOXYETHANOL, 1.00

 butyl paraben,

 ethyl paraben,

 pROPYLPARABEN,

 METHYLPARABEN

 Ethanol 96% (5) ALCOHOL 8.00

Water, AQUA (WATER) 34.90 demineralized

 Dihydroxyacetone (5) DIHYDROXYACETONE 4.00

Total 100.00

Production method:

 First, the magnesium sulfate heptahydrate is dissolved in the water of phase B. Then the remaining components of phase B are added. Phase B is slowly added to Phase A with stirring. It is quickly stirred for a further 2 minutes and homogenized.

Sources:

(1) Degussa-Goldschmidt AG (2) ISP Global Technologies (3) Dow Coming (4) Drom (5) Merck KGaA / Rona® (6) Nipa Laboratories GmbH Example 10: Aqueous-alcoholic tanning lotion for pump sprays

 Production method:

 The MHDE is dissolved in the ethanol and the remaining ingredients are added with stirring. Then the dihydroxyacetone is added and homogenized.

Sources:

 (1) Merck KGaA / Rona® (2) Degussa Goldschmidt AG

Example 11a: W / Si Tanning Gel

DIHYDROXYACETONETHER

B

RonaCare ^® (4) ECTOIN 0.30 Ectoin

 1, 2-propanediol (4) PROPYLENE GLYCOL 30.00

Dipropylene glycol (5) DIPROPYLENE GLYCOL 10.00

Sodium chloride (4) SODIUM CHLORIDE 1.00

Ethanol 96% (4) ALCOHOL 5.00

1% caramel in (6) CARAMEL 2.50 water

 1% FD & C Yellow (5) AQUA (WATER), Cl 15985 0.25 no. 6 in water (FD & C YELLOW NO. 6)

 Water, AQUA (WATER) 19:25 demineralized

 Dihydroxyacetone (4) D I H YD ROXYAC ETO N E 3.00

C

 Fragrance (7) PERFUME 0.20 Melopeach

Total 100.00

Production method:

 Phase B is released and added to Phase A. Phases C and D are added successively with stirring. It is homogenized. The pH is adjusted to pH = 5.0 with sodium hydroxide solution or citric acid.

Sources:

 (1) Dow Coming (2) S. Black GmbH (3) Gustav Heess GmbG

(4) Merck KGaA / Rona® (5) BASF AG (6) D.D. Williamson

(7) drom Example 11b: W / Si Tanning Gel

 Production method:

 Phase B is released and added to Phase A. Phase C is added successively with stirring. It is homogenized.

Sources: (1) Dow Corning (2) S. Black GmbH (3) Gustav Heess GmbH (4) Merck KGaA / Rona® (5) BASF AG (6) DD Williamson (7) Drom

Example 12a: O / W tanning cream with UV A / B protection

Production method: First, phases A and B are mixed separately and heated to 80 ° C. Thereafter, phase B is slowly added with stirring to phase A. It is homogenized and cooled to room temperature. The pH is adjusted to pH = 5.0 with sodium hydroxide solution or citric acid.

Sources:

 (1) Merck KGaA / Rona® (2) Degussa-Goldschmidt AG (3) Cognis GmbH (4) BASF AG (5) Sasol Germany GmbH (6) Dow Corning

Example 12b: O / W tanning cream with UV A / B protection

 Ingredients / Reference INCI [trade name source%]

A

Eusolex ^® 2292 (1) ETHYLHEXYL 3:00

 M ETH OXYC I N AMATE, BHT

Eusolex ^® 4360 (1) Benzophenone-3 00:50

Tego Care 150 (2) GLYCERYL STEARATE, 8.00

 STEARETH-25, CETETH-20,

 STEARYL ALCOHOL

 Lanette O (3) CETEARYL ALCOHOL 1.50

Luvitol EHO (4) CETEARYL OCTANOATE 5.00

Miglyol 812 N (5) CAPRYLIC / CAPRIC 5.00

 TRIGLYCERIDES

 Paraffin liquid (1) PARAFFINUM LIQUIDUM 3.00

 (MINERAL OIL)

 Abil-Wax 2434 (2) STEAROXY DIMETICONE 1.60

Dow Corning 200 (6) DIMETICONE 0.50 Fluid (350 es)

 Propyl 4- (1) PROPYLPARABENE 0.05 hydroxybenzoate

 MBDE (1) MONOBENZYL- 3.00

 DIHYDROXYACETONETHER

B

 1, 2-Propanediol (1) PROPYLENE GLYCOL 3.00

Methyl 4- (1) SODIUM METHYLPARABENES 0.17 hydroxybenzoate

sodium salt Water, AQUA (WATER) 53.18 demineralized

C

 Dihydroxyacetone (1) DIHYDROXYACETONE 2.00

Water, AQUA (WATER) demineralized 10.00

Total 100.00

Production method:

 First, phases A and B are mixed separately and heated to 80 ° C. Thereafter, phase B is slowly added with stirring to phase A. It is homogenized. The mixture is then cooled with stirring and the phase C at 40 ° C was added.

Sources:

 (1) Merck KGaA Rona® (2) Degussa-Goldschmidt AG (3) Cognis GmbH (4) BASF AG (5) Sasol Germany GmbH (6) Dow Coming

Example 12c: O / W tanning cream with UV A / B protection

 Ingredients / Reference INCI [trade name source%]

A

Eusolex ^® 2292 (1) ETHYLHEXYL 3:00

 METHOXYCINNAMATE, BHT

Eusolex ^® 4360 (1) Benzophenone-3 00:50

Tego Care 150 (2) GLYCERYL STEARATE, 8.00

 STEARETH-25, CETETH-20,

 STEARYL ALCOHOL

 Lanette O (3) CETEARYL ALCOHOL 1.50

Luvitol EHO (4) CETEARYL OCTANOATE 5.00

Miglyol 812 N (5) CAPRYLIC / CAPRIC 5.00

 TRIGLYCERIDES

 Paraffin liquid 0) PARAFFINUM LIQUIDUM 3.00

 (MINERAL OIL)

 Abil-Wax 2434 (2) STEAROXY DIMETICONE 1.60

Dow Corning 200 (6) DIMETICONE 0.50 Fluid (350 es) Propyl 4- (1) PROPYLPARABENE 0.05 hydroxybenzoate

 MEHDE (1) MONOETHYLHEXYL- 7.00

 DIHYDROXYACETONETHER

B

 1, 2-Propanediol (1) PROPYLENE GLYCOL 3.00

Methyl 4- (1) SODIUM METHYLPARABENES 0.17 hydroxybenzoate

 sodium salt

 Water, AQUA (WATER) 51.18 demineralized

C

 Water, AQUA (WATER) demineralized 10.00

Total 100.00

Production method:

 First, phases A and B are mixed separately and heated to 80 ° C. Thereafter, phase B is slowly added with stirring to phase A. It is homogenized. The mixture is then cooled with stirring and the phase C at 40 ° C was added.

Sources:

 (1) Merck KGaA / Rona® (2) Degussa-Goldschmidt AG (3) Cognis GmbH (4) BASF AG (5) Sasol Germany GmbH (6) Dow Corning

Example 12d: O / W tanning cream with UV A / B protection

Lanette 0 (3) CETEARYL ALCOHOL 1.50

Luvitol EHO (4) CETEARYL OCTANOATE 5.00

Miglyol 812 N (5) CAPRYLIC / CAPRIC 5.00

 TRIGLYCERIDES

 Paraffin liquid (1) PARAFFINUM LIQUIDUM 3.00

 (MINERAL OIL)

 Abil-Wax 2434 (2) STEAROXY DIMETICONE 1.60

Dow Corning 200 (6) DIMETHICONE 0.50 Fluid (350 es)

 Propyl 4- (1) PROPYLPARABENE 0.05 hydroxybenzoate

 MBDE (1) MONOBENZYL- 1.00

 DIHYDROXYACETONETHER

B

 1, 2-Propanediol (1) PROPYLENE GLYCOL 3.00

Methyl 4- (1) SODIUM METHYLPARABENES 0.17 hydroxybenzoate

 sodium salt

 Water, AQUA (WATER) demineralized 52.18

C

 Dihydroxyacetone (1) D I H Y D ROXYAC ETO N E 5.00

Water, AQUA (WATER) demineralized 10.00

Total 100.00

Production method:

 First, phases A and B are mixed separately and heated to 80 ° C. Thereafter, phase B is slowly added with stirring to phase A. It is homogenized. The mixture is then cooled with stirring and the phase C at 40 ° C was added. The pH is adjusted to pH = 5.0 with sodium hydroxide solution or citric acid.

Sources:

(1) Merck KGaA / Rona® (2) Degussa-Goldschmidt AG (3) Cognis GmbH (4) BASF AG (5) Sasol Germany GmbH (6) Dow Corning Example 12e: O / W tanning cream with UV A / B protection

 Production method:

First, phases A and B are mixed separately and heated to 80 ° C. Thereafter, phase B is slowly added with stirring to phase A. It is homogenized. Sources:

 (1) Merck KGaA / Rona® (2) Degussa-Goldschmidt AG (3) Cognis GmbH (4) BASF AG (5) Sasol Germany GmbH (6) Dow Corning Example 13: O / W Shimmering Tanning Lotion

 Ingredients / Reference INCI [trade name source%]

A

 Montanov 68 (1) CETEARYL ALCOHOL, 4.00

 CETEARYL GLUCOSIDE

 Span 60 (2) SORBITAN STEARATE 1.50

La Nice O (3) CETEARYL ALCOHOL 1.00

Cosmacol ELI (4) C 2-13 ALKYL LACTATE 3.00

Cosmacol EMI (4) DI-C12-13 ALKYL MALATE 1.50

Dow Corning (5) CYCLOMETHICONE, 1.00

9040 Silicone DIMETHICONE

 Elastomer Blend CROSSPOLYMER

 Arlamol HD (2) ISOHEXADECANE 3.00

RonaCare ^® (6) Tocopheryl Acetate 00:50

tocopherol

 acetate

 Propyl 4- (6) PROPYLPARABENE 0.05 hydroxybenzoate

 MBDE (6) MONOBENZYL- 2.00

 D I H YD ROXYAC ETO N ETH E R

 12:50

B

RonaCare ^® (6) ECTOIN 00:50

Ectoin

Colorona ^® Red (6) MICA, Cl 77891 (TITANIUM DIOXIDE 2:00 Gold), Cl 77491 (ION

 OXIDES)

 Glycerin, (6) GLYCERIN 2.00 anhydrous

 Caramel 250 (7) CARAMEL 1.00

FD & C Yellow (8) Cl 15985 0.01

No6 W082

 Water, AQUA (WATER) 73.09 demineralized

 Methyl 4- (6) METHYLPARABENES 0.15 hydroxybenzoate

DHA Plus (6) DIHYDROXYACETONE, 3.00 SODIUM METABISULFITE,

 MAGNESIUM STEARATE c

 Sepigel 305 (1) LAURETH-7, POLYACRYL0.50

 AMIDE, C13-14

 ISOPARAFFIN

D

 Fragrance (9) PERFUME 0.20 Babylon

Total 100.00

Production method:

 First, phases A and B are heated separately to 75 ° C. Thereafter, Phase A is slowly added to Phase B with stirring. At 60 ° C, phase C is added to A / B and it is homogenized. It is then cooled to 40 ° C and the phase D is added successively.

Sources:

 (1) Seppic (2) Uniqema (3) Cognis GmbH (4) Condea Chimica D.A.C.S.p.A. (5) Dow Corning (6) Merck KGaA / Rona® (7) D.D. Williamson (8) Les Colorants Wackherr SA (9) Drom

Example 14: Day Care Cream

Ingredients / Reference INCI [trade name source%]

A

 Tego Care 150 (1) GLYCERYL STEARATE, 8.00

 STEARETH-25, CETETH-20,

 STEARYL ALCOHOL

 Lanette O (2) CETEARYL ALCOHOL 1.50

Tegosoft liquid (1) CETEARYL 6.50

 ETHYLHEXANOATE

 Miglyol 812 N (3) CAPRYLIC / CAPRIC 6.50

TRIGLYCERIDES

 Production method:

 First, the phases A and B are heated separately to 80 ° C. Thereafter, phase B is slowly added with stirring to phase A. It is homogenized. The mixture is then cooled with stirring and the phases C at 40 ° C was added. Phase D is added.

Sources:

 (1) Degussa-Goldschmidt AG (2) Cognis GmbH (3) Sasol Germany GmbH (4) Dow Coming (5) Merck KGaA / Rona® (6) Bell Flavors & Fragrances

Claims

claims

1. Use of a compound of the formula (I)

 as a self-tanning substance, wherein R 1 is a branched or unbranched alkyl radical having 1 to 20 C atoms, a branched or unbranched alkenyl radical having 2 to 20 C atoms or a branched or unbranched alkynyl radical having 2 to 20 C atoms,

wherein one or more non-adjacent and not directly to the O atom of formula (I) adjacent CH ₂ groups may be replaced by C = O or -O-,

where the radicals can be substituted by one or more OH groups, by one or more cyclic alkyl radicals having from 3 to 8 carbon atoms and / or by one or more aromatic ring systems having from 5 to 6 carbon atoms, where the one or more aromatic radicals Ring systems with one or more groups selected from -OH, -OR, -NR ₂ , -CN, -COOR and -COOR 'may be substituted; wherein each occurrence of R independently represents a branched or unbranched alkyl radical having 1 to 20 C atoms; and wherein R 'is an aromatic ring system having 5 or 6 C atoms.

2. Use according to claim 1, characterized in that R 1 is a branched or unbranched alkyl radical having 1 to 20 C atoms, wherein one or more non-adjacent and not directly to the O atom of formula (I) adjacent CH ₂ groups may be replaced by C = 0 or -O-,

 where the radicals can be substituted by one or more OH groups, by one or more cyclic alkyl radicals having from 3 to 8 carbon atoms and / or by one or more aromatic ring systems having from 5 to 6 carbon atoms, where the one or more aromatic radicals Ring systems with one or more groups selected from -OH and -OR may be substituted,

 and wherein R is as defined in claim 1.

3. Use according to claim 1 or 2, characterized in that R1 is a branched or unbranched alkyl radical having 1 to 20 carbon atoms,

wherein one or more non-adjacent and not directly to the O atom of formula (I) adjacent CH ₂ groups may be replaced by C = O or -O-,

 where the radicals can be substituted by one or more OH groups, by one or more cyclic alkyl radicals having from 5 to 6 carbon atoms and / or by one or more aromatic ring systems having from 5 to 6 carbon atoms, where the one or more aromatic radicals are substituted by one or more OH radicals Ring systems with one or more groups -OR may be substituted,

 and wherein R is as defined in claim 1.

Use according to one or more of Claims 1 to 11, characterized in that the compound of the formula (I) is selected from the compounds of the formulas (Ia) to (Ik)

5. Use according to one or more of claims 1 to 4,

 characterized in that the use is carried out together with DHA and / or erythrulose.

6. Preparation comprising at least one compound of the formula (I)

 where R 1 is a branched or unbranched alkyl radical having 1 to 20 C atoms, a branched or unbranched alkenyl radical having 2 to 20 C atoms or a branched or unbranched alkynyl radical having 2 to 20 C atoms,

 one or more non-adjacent and not directly to the O-

Atom of formula (I) adjacent CH ₂ groups may be replaced by C = O or -O-, which radicals can be substituted by one or more OH groups, one or more cyclic alkyl radicals having 3 to 8 C atoms and / or by one or more aromatic ring systems having 5 to 6 C atoms, wherein the one or more aromatic ring systems may be substituted with one or more groups selected from -OH, -OR, -NR ₂ , -CN, -COOR and -COOR '; wherein each occurrence of R independently represents a branched or unbranched alkyl radical having 1 to 20 C atoms; and wherein R 'is an aromatic ring system having 5 or 6 C atoms.

7. Preparation according to claim 6, characterized in that the

 Preparation of at least one compound of formula (I) in an amount of 0.01 to 20 wt .-%, based on the total amount of

 Preparation containing.

8. Preparation according to claim 6 or 7, characterized in that the preparation contains at least one further self-tanning substance.

9. Preparation according to claim 8, characterized in that the

 Self-tanning substance is selected from DHA and erythrulose.

10. Preparation according to one or more of claims 6 to 9, characterized in that the preparation additionally contains at least one UV filter.

11.A method for preparing a preparation according to one or more of claims 6 to 10, characterized in that the at least one compound of formula (I) with at least one for topical Preparations suitable carrier and optionally mixed with excipients and / or fillers.

12. Compounds of the formula (I)

 where R 1 is a branched or unbranched alkyl radical having 1 to 20 C atoms, a branched or unbranched alkenyl radical having 2 to 20 C atoms or a branched or unbranched alkynyl radical having 2 to 20 C atoms,

wherein one or more non-adjacent and not directly to the O atom of formula (I) adjacent CH ₂ groups may be replaced by C = O or -O-,

which radicals can be substituted by one or more OH groups, one or more cyclic alkyl radicals having 3 to 8 C atoms and / or by one or more aromatic ring systems having 5 to 6 C atoms, wherein the one or more aromatic ring systems may be substituted with one or more groups selected from -OH, -OR, -NR ₂ , -CN, -COOR and -COOR '; wherein each occurrence of R independently represents a branched or unbranched alkyl radical having 1 to 20 C atoms; and wherein R 'is an aromatic ring system having 5 or 6 C atoms; and wherein the following compounds are excluded:

 O O

OO OO

O OH O OH

13. Compounds of formula (I) according to claim 12, characterized

in that the compounds are selected from the compounds of the formulas (Ib) to (Ik), 15, 17 (| ο) _

14. A process for the preparation of a compound of formula (I) according to

Claim 12 or 13, characterized in that 2,5-diethoxy-2,5-bis (hydroxymethyl) -1, 4-dioxane is reacted with a compound of formula R1-X and then acid hydrolyzed, wherein X is Cl, Br , I, OSO2CH3 (O-mesyl) or OSO2C6H ₄ CH3 (OTosyl) stands.