EP1960342A1

EP1960342A1 - Erythrulose esters as uv filters

Info

Publication number: EP1960342A1
Application number: EP06828978A
Authority: EP
Inventors: Thomas Rudolph; Herwig Buchholz; Frank Pfluecker
Original assignee: Merck Patent GmbH
Current assignee: Merck Patent GmbH
Priority date: 2005-12-08
Filing date: 2006-11-09
Publication date: 2008-08-27
Also published as: DE102005058542A1; WO2007065524A1

Abstract

The invention relates to compounds of formula (I) in which X, Y and Z stand for O, NH or N-alkyl, Sp, Sp' and Sp" can be alike or different and stand for -H, -(CH2)n-, -(CH2)n-C(=O)-(CH2)o- or -(CH2)n-C(=O)-(CH2)o-X-(CH2)p-, n, o, p and q stand for a whole number selected independently of one another from the range beginning with 0 and ending with 40, and A, A' and A" stand for a substituent which absorbs UV radiation and has a conjugated p electron system of at least 4p electrons, it being possible for A, A' and A" in turn to be substituted by one or more groups -Sp-X-CH2-C(=O)-CH2-OH and to be alike or different, and A, A' and A" being absent from the positions at which Sp, Sp' or Sp" is H; preparations which comprise such compounds; and their use.

Description

Erythrulose ester as UV filter

The invention relates to UV filters, preparations containing such UV filters, corresponding processes for the production of the UV filters or the preparations containing them and their use.

In particular, the invention relates to the use of erythrulose esters as light protection filters for cosmetic or pharmaceutical products as well as new erythrulose esters, processes for their preparation and their

Use in cosmetic preparations, in particular for protection against solar radiation and in pharmaceutical preparations.

Human skin is subject to certain aging processes, which are partly due to intrinsic processes (chronoaging) and partly to exogenous factors (environmental, e.g. photoaging). In addition, temporary or permanent changes in the skin appearance can occur, such as acne, oily or dry skin, keratoses, rosaceae, photosensitive, inflammatory, erythematous, allergic or autoimmune-reactive reactions such as dermatoses and photodermatoses. The exogenous factors include in particular sunlight or artificial radiation sources with a comparable spectrum as well

Compounds that can arise from the radiation, such as undefined reactive photo products, which can also be radical or ionic. These factors also include cigarette smoke and the reactive compounds it contains, such as ozone, free radicals, for example that

Hydroxyl radical, singlet oxygen and other reactive oxygen or nitrogen compounds that interfere with the natural physiology or morphology of the skin. The influence of these factors can, among other things, lead to direct damage to the DNA of the skin cells and to the collagen, elastin or glycosaminoglycan molecules of the extracellular matrix, which are responsible for the firmness of the skin. In addition, there may be an influence on the signal transduction chains on their The end of the activation of matrix-degrading enzymes. Important representatives of these enzymes are the matrix metalloproteinases (MMPs, e.g.

Collagenases, gelatinases, stromelysins), the activity of which is additionally regulated by TIMPs (tissue inhibitor of matrix metalloproteinases). The consequences of the above Aging processes include thinning of the skin, weaker interlocking of the epidermis and dermis, reduction in the number of cells and the supplying blood vessels. It comes to

Formation of fine lines and wrinkles, the skin becomes leathery and pigment disorders can occur.

The same factors also affect hair, where damage can also occur. The hair becomes brittle, less elastic and lackluster. The surface structure of the hair is damaged. There is therefore a need for further compounds which absorb UV radiation and are thus able to protect human skin.

It has now been found that certain erythrulose derivatives are more suitable for this, since they are potentially able to act in the sense of a

Maillard reaction to eliminate water from the molecule. In contrast to DHA UV filter derivatives (see DE

102004039281.1) better bind to skin components on the skin. However, the elimination of the chromophoric group is difficult. A first subject of the present application are therefore

Compounds according to formula I.

wherein

X represents O, NH or N-alkyl,

Y stands for O, NH or N-alkyl

Z stands for O, NH or N-alkyl

Sp, Sp ^' , Sp ^" can be the same or different and stand for -H, - (CHz) _n -, - (CH ₂ ) nC (= O) - (CH ₂ ) ₀ - or - (CH ₂ ) _n - C (= O) -

(CH ₂ ) oX- (CH ₂ ) p-,

n, o, p, q stand for an integer independently selected from the range starting with O and ending with 40 and

A, A ^' and A ^" stand for a substituent which absorbs UV radiation and has a conjugated π-electron system of at least 4π-electrons, A, A ^' and A ^" again having one or more groups -Sp-X-CH ₂ -C (= O) -CH ₂ -OH substituted and may be the same or different and where

A, A ^' and A ^" are omitted at the positions at which Sp, Sp ^' or Sp ^{" are} equal to H.

The compounds of formula I or the derivatives of

Erythrulose is present in monomeric, dimeric or isomeric form (for example as D- or L-isomer or as tetrose (as threose or erythrose) or as a mixture of these forms. - A -

Preparations which contain at least one compound of the formula I are a further subject of the invention.

The use of at least one compound according to formula I or a preparation which contains at least one compound according to formula I for the care, preservation or improvement of the general condition of the

Skin or hair and preferably for prophylaxis against time and / or light-induced aging processes of human skin or

human hair, in particular for prophylaxis against dry skin, wrinkling and / or pigment disorders, and / or for reducing or preventing damaging effects of UV rays on the skin and for prophylaxis against or reducing skin imperfections, such as wrinkles, fine lines, rough skin or Large-pored skin are further objects of the present invention in accordance with the advantageous properties of the compounds according to the invention.

The conventional light protection filters usually have little or insufficient skin adhesion, which leads to a shorter duration of the protective effect of the filter and in particular to the almost complete removal of the filter when bathing.

It therefore appears further desirable to provide compounds that can protect human skin against UV rays for a long time. The present invention solves this problem with the compounds preferred according to the invention, in which X, Y and / or Z are O. These compounds according to the invention are able to chemically link to the skin. It is known that the α-hydroxyketone derivatives have excellent skin adhesion and, in some cases, a self-tanning effect, such as other hydroxyketone compounds (dihydroxyacetone). From EP 0 758 314 B1 maleimides and maleic acid derivatives are known which can react with SH groups present in the skin.

US Pat. No. 6,613,341 B2 discloses α, β-unsaturated ketones which are chemically linked to UV filters or antioxidants.

Α-Hydroxyketoalkyl derivatives are known from EP 0 581 954 B1.

DHA carbonates are known from EP 796838 A1, which can be used as self-tanning agents in cosmetic formulations.

EP 710478 A1 and EP 709081 A1 disclose DHA fatty acid esters which can be used together with lipase as a self-tanning agent in creams.

From DE 19720831 some DHA esters are known which can be used as self-tanning agents and sunscreens.

In preferred variants of the present invention, A, A ^' or A ^' stand for structures which are known from conventional UV filters. It is particularly preferred according to the invention if A, A ^' or A "stand for a radical selected from the group with the following elements:

where X, X ₁ , X ₂ . X ₃ and X ₄ each independently of one another H, OH,

CH ₃ COO, an alkyl radical with 1 to 8 C atoms, particularly preferably an alkoxy radical with 1 to 8 C atoms, particularly preferably -O- C (CH ₃ ) _3ι -O-CH (CH ₃ ) ₂ θ or -ethylhexyloxy, or a monoglycoside residue, n is 0, 1, 2 or 3, m 0 or 1, k 0, 1, 2, 3 or 4 and MH, Na or K.

Also preferred is a compound of the formula I ₁ in which Sp-A and / or Sp ^' -A ^' and / or Sp ^" -A" is C = O.

Even more preferred is a compound of formula I, which is a 1, 3,4-tri, 1, 3-di, 1, 4-di, 3,4-di, 1-mono, 3-mono - or 4-monoester of erythrulose. Even more preferred is a 1-mono, 3-mono, or 4-monoester of erythrulose, with a 4-monoester of erythrulose being the most preferred.

In a group of compounds of formula I which are preferably to be used as UV filters, it is particularly preferably a

Compound from the following group:

35 The compounds according to the invention can, depending on the heteroatom X, Y and Z and chromophore "A, A 'and A"", according to different

Synthetic principles are presented.

So is a process for the preparation of compounds according to formula I wherein X ₁ Y or Z are O, characterized in that erythrulose or an erythrulose derivative in which a hydroxyl group is provided with a protective function with an acid chloride R- (CH ₂ ) _m - (C = O) CI is implemented, another object of the present invention.

The reaction of acid chlorides with erythrulose results in a mixture of the monosubstituted product and the disubstituted or trisubstituted product.

Preparative acylation takes place in solvents that are inert to acid chlorides (such as pyridine, dimethylformamide, acetonitrile and ionic liquids). It is also preferred to implement the perform aqueous alkaline solution. For this purpose, the so-called Schotten-Baumann method is preferably used, in which, for. B. the corresponding acid chlorides with erythrulose in the presence of sodium hydroxides.

The erythrulose molecule can also be coupled with other electrophilic reagents.

For example, the Ar-CH ₃ group in methylbenzylidene camphor can be converted to an alkyl bromide. The camphor derivative is brominated by N-bromosuccinimide in the presence of initiators (C. Bouillon, C. Vayssie, in Ger. Offen., (Oreal SA, Fr.). Appl: DE 19780314. 78-2811041, 1978, p. 71. C. Bouillon, C. Vayssie, in Fr. Demande, (Oreal SA, Fr.), Fr, Number 2421878, 1979, p. 31. C. Bouillon, C. Vayssie, (Oreal SA, Fr.). Ca, Number 1113480, 1981, p. 61).

The further coupling with 2,2-dimethoxy-1,3-propanediol provides an intermediate which can be further hydrolyzed to the compound of the formula I without any problems.

Accordingly, a method for the production of

Compounds according to formula I, where X is O _1, which is characterized in that 2,2-dimethoxy-1,3-propanediol with a compound A-Sp-HaI, where HaI is Cl, Br or I and the other radicals correspond to the definition given above, is implemented and the

Dimethoxy function is then hydrolyzed to the ketone, object of the present invention.

Another object of the present inventions are

Preparations containing a suitable carrier, thereby

characterized in that the preparation contains 0.001 to 99 wt .-% of at least one compound of formula I or its topically tolerable salts and / or derivatives. One or more compounds of the formula I are preferably in amounts of 0.01 to 20% by weight,

preferably 0.05 to 10 wt .-% and particularly preferably 0.1 to 5 wt .-% in the preparation.

In a preferred embodiment of the present invention, the preparation is a preparation for the protection of

Body cells against oxidative stress, in particular for reducing skin aging, characterized in that, in addition to one or more compounds according to formula I, one or more others

Contains antioxidants and / or one or more additional UV filters.

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

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

Chlorogenic acid and its derivatives, lipoic acid and its derivatives (e.g. dihydroliponic acid), aurothioglucose, propylthiouracil and other thiols (e.g. thioredoxin, glutathione, cysteine, 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 their derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (e.g. buthioninsulfoximines,

Homocysteine sulfoximine, buthionine sulfones, penta-, hexa-, heptathionine sulfoximine) in very low tolerable doses (e.g. pmol to μmol / kg), also (metal) chelators, (e.g. α-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), α-hydroxy acids (e.g. citric acid,

Lactic acid, malic acid), humic acid, bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives, vitamin C and derivatives (e.g. ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl acetate), tocopherols and derivatives (e.g. vitamin E-acetate), vitamin A and derivatives (e.g. vitamin A palmitate) and coniferyl benzoate of benzoin, rutinic acid and their

Derivatives, α-glycosyl rutin, ferulic acid, Furfurylidenglucitol, carnosine, butylhydroxytoluene, butylhydroxyanisole, Nordohydroguajaretsäure, tri- hydroxybutyrophenon, quercetin, uric acid and derivatives thereof, mannose and derivatives thereof, zinc and derivatives thereof (for example ZnO, _ZnSO4), selenium and derivatives thereof (e.g. selenium methionine), stilbenes and their derivatives (e.g. stilbene oxide, trans-stilbene oxide).

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

The preparations according to the invention can contain vitamins as further ingredients. Vitamins and vitamin derivatives are preferred. selected from vitamin A, vitamin A propionate, vitamin A palmitate, vitamin A acetate, retinol, vitamin B, thiamine chloride hydrochloride (vitamin Bi), riboflavin (vitamin B ₂ ), nicotinic acid amide, vitamin C (ascorbic acid), vitamin D, ergocalciferol (vitamin D ₂ ), vitamin E, DL-α-tocopherol, tocopherol E acetate, tocopherol hydrogen succinate, vitamin Ki, esculin (vitamin P active ingredient), thiamine (vitamin Bi), nicotinic acid (niacin), pyri- doxin, pyridoxal, pyridoxamine, (vitamin B ₆ ), pantothenic acid, biotin, folic acid and cobalamin (vitamin B ₁₂ ) in the invention

contain cosmetic preparations, particularly preferably vitamin A palmitate, vitamin C and its derivatives, DL-α-tocopherol,

Tocopherol E acetate, nicotinic acid, pantothenic acid and biotin. Vitamins are combined with compounds of formula I or formula II

usually used in ratios in the range from 1000: 1 to 1: 1000, preferably in amounts of 100: 1 to 1: 100. Among the phenols with an antioxidative effect are the polyphenols, some of which are natural substances, for applications in

pharmaceutical, cosmetic or nutritional area particularly interesting. For example, they mainly show as

Plant dyes often have an antioxidant potential for known flavonoids or bioflavonoids. K. Lemanska deals with effects of the substitution pattern of mono- and dihydoxyflavones,

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 with an OH group adjacent to the keto function or OH groups in the 3'4'- or 6.7- or 7.8-position are antioxidative

Have properties, while other mono- and dihydroxyflavones sometimes have no antioxidative properties.

Quercetin (cyanidanol, cyanidenolone 1522, meletin,

Sophoretin, Ericin, 3,3 ', 4', 5,7-Pentahydroxyflavon) mentioned as a particularly effective antioxidant (e.g. CA.Rice-Evans, NJ Miller, G. Paganga, Trends in Plant Science 1997, 2 (4), 152 -159). K. Lemanska, H. Szymusiak, B. Tyrakowska, R. Zielinski, A.E. M. F. Soffers,

IMCM Rietjens; Free Radical Biology & Medicine 2001, 31 (7), 869-881 investigate the pH dependence of the antioxidant effect of Hydroxyflavones. Quercetin shows the highest activity of the examined structures over the entire pH range.

Suitable antioxidants are also compounds of the formula

wherein R ¹ to R ^{10 may be the} same or different and are selected from

H

OR 11 straight-chain or branched Cr to C ₂ o -alkyl groups, straight-chain or branched C ₃ - to C ₂ o-alkenyl groups, straight-chain or branched Ci to C ₂ o-hydroxyalkyl groups, the hydroxyl group being attached to a primary or secondary

Carbon atom of the chain can be bound and the alkyl chain can also be interrupted by oxygen, and / or

C ₃ - to C-io-cycloalkyl groups and / or C ₃ - to Ci2-cycloalkenyl groups, where the rings can also be bridged by - (CH ₂ ) _n groups with n = 1 to 3, all OR ¹¹ stand independently for

OH straight-chain or branched C ₁ - to C ₂ o-alkyloxy groups, straight-chain or branched C ₃ - to C ₂ o-alkenyloxy groups, straight-chain or branched Cr to C ₂ o-hydroxyalkoxy groups, the hydroxy group (s) being attached to a primary or secondary Carbon atoms of the chain can be bound and the alkyl chain can also be interrupted by oxygen, and / or

C ₃ - to Cio-Cycloalkyloxygruppen and / or C ₃ - to Ci ₂ -cyclo-Ikenyloxygruppen, where the rings can also be bridged by - (CHb) _n - groups with n = 1 to 3 and / or,

Mono- and / or oligoglycosyl radicals, with the proviso that at least 4 radicals from R ¹ to R ⁷ stand for

OH and that in the molecule at least 2 pairs of neighboring groups

-OH are present, or R ² , R ⁵ and R ^{6 are} OH and the radicals R ¹ , R ³ , R ⁴ and R ^{7-10 are} H, as described in German patent application DE-A-10244282.

Preparations preferred according to the invention can in addition to the

Compounds of formula I also contain other UV filters.

When using the particularly preferred as UV-A filter

Dibenzoylmethane derivatives in combination with the compounds of formula I result in an additional advantage: the UV-sensitive

Dibenzoylmethane derivatives are caused by the presence of the

Compounds of formula I additionally stabilized. The present invention therefore furthermore relates to the use of the compounds of the formula I for stabilizing dibenzoylmethane derivatives in preparations. In principle, all UV filters can be used in combination with the compounds of the formula I according to the invention. Those UV filters whose physiological harmlessness has already been proven are particularly preferred. Both for UVA and UVB filters, there are many well-known and proven substances from the specialist literature, e.g.

Benzylidene camphor derivatives such as 3- (4 ^' -methylbenzylidene) dl-camphor (e.g. Eusolex® 6300), 3-benzylidene camphor (e.g. Mexoryl® SD), polymers of N - {(2 and 4) - [(2-oxoborn-3- yliden) methyl] benzyl} -acrylamide (e.g. Mexoryl® SW), N, N, N-trimethyl-4- (2-oxobom-3-ylidenmethyl) anilinium methyl sulfate (e.g. Mexoryl® SK) or (2-oxoborn-3- ylidene) toluene-4-sulfonic acid (e.g. Mexoryl® SL),

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

Benzophenones such as 2-hydroxy-4-methoxybenzophenone (e.g. Eusolex® 4360) or 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and its sodium salt (e.g. Uvinul® MS-40),

Methoxycinnamic acid esters such as octyl methoxycinnamate (e.g. Eusolex® 2292), isopentyl 4-methoxycinnamate, e.g. as a mixture of the isomers (e.g. Neo Heliopan® E 1000), salicylate derivatives such as 2-ethylhexylsalicylate (e.g. Eusolex® OS) ₁ 4-isopropylbenzyl (e.g. or 3,3,5-trimethylcyclohexyl salicylate (e.g. Eusolex® HMS),

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

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

and other substances like

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

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

- 2.4 _I 6-trianilino- (p-carbo-2 ^' -ethylhexyl-r-oxi) -1 _I 3,5-triazine (e.g.

Uvinul® T 150)

2- (4-Diethylamino-2-hydroxy-benzoyl) -benzoic acid hexyl ester (e.g. Uvinul®UVA Plus, from BASF). The compounds in the list are only examples. Of course, other UV filters can also be used.

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

Other suitable organic UV filters are, for example. 2- (2H-benzotriazole-2-yl) -4-methyl-6- (2-methyl-3- (1, 3,3,3-tetramethyl-1- (trimethylsilyloxy) disiloxanyl) propyl) phenol (for example Silatrizole ^® ),

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

Uvasorb ^® HEB),

α- (Trimethylsilyl) -ω- [trimethylsilyl) oxy] poly [oxy (dimethyl [and about 6% methyl [2- [p- [2,2-bis (ethoxycarbonyl] vinyl] phenoxy} -1-methyleneethyl] and approx. 1.5% methyl [3- [p- [2,2-bis (ethoxycarbonyl) vinyl) phenoxy) propenyl) and 0.1 to 0.4% (methylhydrogenjsilylene]] (n «60) (CAS- No. 207 574-74-1) 2,2 ^' -methylene-bis- (6- (2H-benzotriazol-2-yl) -4- (1,1,3,3-tetramethylbutyl) phenol) (CAS No. 103 597-45-1 )

2,2 ^' - (1,4-phenylene) bis- (1H-benzimidazole-4,6-disulfonic acid,

Monosodium salt) (CAS No. 180 898-37-7) and

- 2,4-bis - {[4- (2-ethylhexyloxy) -2-hydroxyl] phenyl} -6- (4-methoxyphenyl) -1, 3,5-triazine (CAS No. 103 597- 45-, 187 393-00-6).

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

Uvasorb ^® HEB),

Other suitable UV filters are also methoxy flavones according to the older German patent application DE-A-10232595.

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

Conceivable inorganic UV filters are those from the group of titanium dioxides, such as coated titanium dioxide (for example Eusolex® T-2000, Eusolex ^® T-AQUA, Eusolex® T-AVO), zinc oxides (eg Sachtotec.RTM), iron oxides and also

Cerium oxides conceivable. These inorganic UV filters are generally incorporated into cosmetic preparations in an amount of 0.5 to 20 percent by weight, preferably 2 to 10%. Preferred compounds with UV filtering properties are 3- (4 ^' -

Methylbenzylidene) dl-camphor, 1- (4-tert-butylphenyl) -3- (4-methoxyphenyl) - pro-pan-1, 3-dione, 4-isopropyldibenzoylmethane, 2-hydroxy-4-methoxybenzophenone , Octyl methoxycinnamate, 3,3,5-trimethyl-cyclo-hexyl salicylate, 2-ethyl-hexyl 4- (dimethylamino) benzoate, 2-ethylhexyl 2-cyano-3,3-di-phenyl-acrylate, 2-phenyl-benzimidazole-5-sulfonic acid and its potassium, sodium and triethanolamine salts.

By combining one or more compounds of the formula I with further UV filters, the protective action against harmful

Effects of UV radiation can be optimized. Optimized compositions can contain, for example, the combination of UVA with UV filters according to formula I. This combination provides broadband protection that can be supplemented by adding inorganic UV filters such as titanium dioxide microparticles.

All of the UV filters mentioned can also be used in encapsulated form. The compounds of the formulas I in

encapsulated form can be used. However, it is preferred to use the skin-adhering compounds of the formula I in unencapsulated form. It is particularly advantageous to use encapsulated organic UV filters. The individual advantages are as follows:

The hydrophilicity of the capsule wall can be adjusted independently of the solubility of the UV filter. For example, hydrophobic UV filters can also be incorporated into purely aqueous preparations. In addition, the oily impression that is often perceived as unpleasant is prevented when the preparation containing the hydrophobic UV filter is applied.

Certain UV filters, especially dibenzoylmethane derivatives, show only a reduced photostability in cosmetic preparations. By encapsulating these filters or compounds that impair the photostability of these filters, such as cinnamic acid derivatives, the photostability of the entire preparation can be increased.

Skin penetration through organic UV filters and the associated potential for irritation when applied directly to human skin are repeatedly discussed in the literature. This effect is prevented by the encapsulation of the corresponding substances proposed here.

In general, encapsulation of individual UV filters or other ingredients can cause preparation problems caused by changing The effect of individual preparation components on one another arises, as crystallization processes, precipitations and agglomerate formation are avoided, since the interaction is prevented.

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

Suitable capsules can have walls made of inorganic or organic polymers. For example, in US 6,242,099 B1

Production of suitable capsules with walls made of chitin, chitin derivatives or polyhydroxylated polyamines. Capsules to be used particularly preferably according to the invention have walls which can be obtained by a SolGel process, as described in the applications WO 00/09652, WO 00/72806 and WO 00/71084. Again, capsules are preferred, the walls of which are made of silica gel (silica; undefined silicon oxide hydroxide). The manufacture of corresponding capsules is known to the person skilled in the art, for example from the cited patent applications, the content of which expressly belongs to the subject of the present application. The capsules are in preparations according to the invention

preferably contained in amounts that ensure that the encapsulated UV filter in the amounts specified above in the

Preparation. It can be preferred according to the invention if the preparations contain active substances that facilitate skin penetration, so-called “penetration enhancers”. These active substances that facilitate skin penetration can have the effect that the skin-adhering UV filters according to the invention penetrate into deeper skin layers, which are rejected only after a considerable time and thereby a particularly long-lasting UV Provide protection. Various substances are described in the literature as suitable enhancers, which are divided into three classes (Lambert WJ, Kudlar RJ, Hollard JM, Curry JT (1993) Int J Pharm, 45: 181): solvents with H-bond acceptors, simple fatty acids and Alcohols and weakly surfactants. A chemical classification differentiates between alcohols, sulfoxides,

Fatty acids, fatty acid esters, polyols, surfactants, terpenes and organic acids (Kalbitz J., Neubert R., Wohlrab W. (1996) Modulation of the active substance penetration into the skin. Pharmacy, 51: 619-637). Ethanol and 1,2-propanediol are among the active substances which are particularly preferred according to the invention and which facilitate skin penetration.

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

It may further be preferred if the preparation according to the invention contains at least one repellent, the repellent preferably being selected from N, N-diethyl-3-methylbenzamide, 3- (acetyl-butylamino) propionic acid, ethyl ester, dimethylphthalate, butopyronoxyl, 2 , 3,4,5-bis (2-butylene) -tetrahydro-2-furaldehyde, N, N-caprylic acid diethylamide, N ₁ N-diethylbenzamide, o-chloro-NN-diethylbenzamide, dimethyl carbate, di-n-propylisocinchomeronate, 2 -Ethylhexane-1, 3-diol, N-octyl-bi-cyclohepete-diecarboximid, piperonyl butoxide, 1- (2-methylpropyloxycarbonyl) -2- (hydroxyethyl) -piperidine or mixtures thereof, it being particularly preferably selected from N. , N-Diethyl-3-methylbenzamide, ethyl 3- (acetylbutylamino) propionate 1- (2-methylpropyloxycarbonyl) -2- (hydroxyethyl) piperidine or mixtures thereof.

The preparations according to the invention, which contain repellents, are preferably insect repellants. Insect repellents are offered in the form of solutions, gels, pens, rollers, pump sprays and aerosol sprays, with solutions and

Sprays form the main part of the commercially available products. The basis for these two product forms are mostly alcoholic or aqueous alcoholic solutions with the addition of greasy substances and light perfuming.

Particularly preferred active ingredients are, for example, so-called compatible solutes. These are substances that are involved in the osmoregulation of plants or microorganisms and can be isolated from these organisms. The generic term compatible solutes also includes the osmolytes described in German patent application DE-A-10133202. Suitable osmolytes are, for example, the polyols, methylamine compounds and amino acids and their respective precursors. In the sense of German patent application DE-A-10133202, osmolytes are understood in particular to be substances from the group of polyols, such as, for example, myo-inositol, mannitol or sorbitol and / or one or more of the osmolytically active substances mentioned below:

Taurine, choline, betaine, phosphorylcholine, glycerophosphorylcholines, glutamine, glycine, α-alanine, glutamate, aspartate, proline, and taurine.

Precursors of these substances are, for example, glucose, glucose polymers, phosphatidylcholine, phosphatidylinositol, inorganic phosphates, proteins, peptides and polyamic acids. Precursors are e.g. B. Compounds that are converted to osmolytes by metabolic steps.

According to the invention, compatible solutes are preferably selected from the group consisting of pyrimidinecarboxylic acids (such as ectoin and hydroxyectoin), proline, betaine, glutamine, cyclic diphosphoglycerate, N.-acetylornithine, trimethylamine-N-oxide di-myo-inositol-phosphate ( DIP), cyclic 2,3-diphosphoglycerate (cDPG), 1,1-diglycerol phosphate (DGP), ß-mannosylglycerate (Firoin), ß-mannosylglyceramide (Firoin-A) or / and di-mannosyl-di-inositol phosphate ( DMIP) or an optical isomer, derivative, e.g. an acid, a salt or ester of these compounds or combinations thereof.

Among the pyrimidinecarboxylic acids are especially ectoin ((S) - 1, 4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid) and hydroxyectoin ((S ₁ S) -1, 4,5,6-tetrahydro-5 -hydroxy-2-methyl-4-pyrimidinecarboxylic acid and to name their derivatives. These compounds stabilize enzymes and other biomolecules in aqueous solutions and organic ones

Solvents. Furthermore, they particularly stabilize enzymes against denaturing conditions, such as salts, extreme pH values, surfactants, urea, guanidinium chloride and other compounds.

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

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

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

wherein R ^{1 is} H or C1-8 alkyl, R ^{2 is} H or C1-4 alkyl and R ³ , R ⁴ , R ⁵ and R ^{6 are} each independently a group Are H, OH, NH ₂ and C1-4 alkyl. Pyrimidinecarboxylic acids in which R ^{2 is} a methyl or an ethyl group and R ¹ or R ⁵ and R ^{6 are} H are preferably used. The pyrimidinecarboxylic acids ectoin ((S) -1, 4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid) and hydroxyectoin ((S, S) -1, 4,5,6- Tetrahydro-5-hydroxy-2-methyl-4-pyrimidine-carboxylic acid) used. The preparations according to the invention preferably contain pyrimidinecarboxylic acids of this type in amounts of up to 15% by weight. The pyrimidinecarboxylic acids are preferably used in ratios of 100: 1 to 1: 100 to the compounds of the formula I, ratios in the range 1:10 to 10: 1 being particularly preferred.

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

Among the aryl oximes likewise preferably used, 2-hydroxy-5-methyllaurophenone oxime, which is also referred to as HMLO, LPO or F5, is preferably used. Its suitability for use in

cosmetic products is, for example, from the German

Publication DE-A-41 16 123 known. Preparations which contain 2-hydroxy-5-methyllaurophenone oxime are accordingly for

Treatment of skin diseases associated with inflammation. It is known that such preparations e.g. can be used to treat psioriasis, various forms of eczema, irritative and toxic dermatitis, UV dermatitis and other allergic and / or inflammatory diseases of the skin and the appendages of the skin. Preparations according to the invention which, in addition to the

Compound of formula I additionally contain an aryl oxime, preferably 2-hydroxy-5-methyllaurophenone oxime, show surprising anti-inflammatory suitability. The preparations contain

preferably 0.01 to 10% by weight of the aryloxime, it being particularly preferred if the preparation contains 0.05 to 5% by weight of aryloxime. In a further likewise preferred embodiment of the present invention, the preparation according to the invention contains at least one self-tanner.

The following can be used as advantageous self-tanners:

HC = OH ₂ C-OH

I.

HC = O HC = O CH ₂ HC-OH

I I

II HC-OH C = O CH ₂ C = O

I.

I I I I I

H ₂ C-OH H ₂ C-OH HC = OH ₂ C-OH

Blycerolaldehv rd hydroxymethylglyoxal succinic dialdehyde Erythn

H ₂ C-OH

Also worth mentioning is 5-hydroxy-1,4-naphthoquinone (juglone), which is extracted from the shells of fresh walnuts

5-hydroxy-1,4-naphthoquinone (juglone) as well as the 2-hydroxy-1,4-naphthoquinone (Lawson) found in the henna leaves.

2-hydroxy-1,4-naphthoquinone (Lawson)

H ₂ C-OH

C = O

H ₂ C-OH

1,3-dihydroxyacetone (DHA)

The preparations according to the invention can also contain dyes and color pigments. The dyes and pigments can be selected from the corresponding positive list of the Cosmetics Regulation or the EC list of cosmetic colorants. In most cases, they are identical to the colorants approved for food. Advantageous color pigments are, for example, titanium dioxide, mica, iron oxides (for example Fe ₂ O ₃ , Fe ₃ O ₄ , FeO (OH)) and / or tin oxide. Advantageous dyes are, for example, carmine, Berlin blue, chrome oxide green, ultramarine blue and / or manganese violet. It is particularly advantageous to choose the dyes and / or color pigments from the list below. The Color Index Numbers (CIN) are taken from the Rowe Color Index, 3rd edition, Society of Dyers and Colorists, Bradford, England, 1971.

It may also be advantageous to choose one or more substances from the following group as the dye:

2,4-dihydroxyazobenzene, 1- (2'-chloro-4'-nitro-1'phenylazo) -2-hydroxynaphthalene, ceres red, 2- (4-sulfo-1-naphthylazo) -1-naphthol-4- sulfonic acid, calcium salt of 2-hydroxy-1, 2'-azonaphthalene-1'-sulfonic acid, calcium and barium salts of 1- (2-sulfo-4-methyl-1-phenylazo) -2-naphthylcarbonic acid, calcium salt of 1- (2-Sulfo-1-naphthylazo) -2-hydroxynaphthalene-3-carboxylic acid, aluminum salt of 1- (4-sulfo-1-phenylazo) -2-naphthol-6-sulfonic acid, aluminum salt of 1- (4-sulfo -1-naphthylazo) -2-naphthol-3,6-disulfonic acid, 1- (4-sulfo-1-naphthylazo) -2-naphthol-6,8-disulfonic acid, aluminum salt of 4- (4-sulfo-1-phenylazo ) -2- (4-sulfophenyl) -5- (big blank) pyrazolone-3-carboxylic acid, aluminum and zirconium salts of 4,5-dibromo-fluorescein, aluminum and zirconium salts of 2,4,5,7-tetrabromofluorescein, S '^'. δ'.θ'-tetrachlor ^ ASy-tetrabromofluorescein and its aluminum salt, aluminum salt of 2,4,5,7-tetraiodofluorescein, aluminum salt of quinophthalone disulfonic acid, aluminum salt of indigo disulfonic acid, red and black iron oxide (CIN: 77 491 (red) and 77 499 (black) ), Iron oxide hydrate (CIN: 77492),

Manganese ammonium diphosphate and titanium dioxide.

Also advantageous are oil-soluble natural dyes, such as. B. paprika extract, ß-carotene or cochineal.

Gel creams containing pearlescent pigments are also advantageous for the purposes of the present invention. The types of pearlescent pigments listed below are particularly preferred:

1. Natural pearlescent pigments, such as. B.

1. "Fish silver" (guanine / hypoxanthine mixed crystals

Fish scales) and

2. "mother-of-pearl" (milled mussel shells)

2. Monocrystalline pearlescent pigments such as B. bismuth oxychloride

(BiOCI) 3rd layer substrate pigments: e.g. B. mica / metal oxide

Pearlescent pigments are based, for example, on powdered pigments or castor oil dispersions of bismuth oxychloride and / or titanium dioxide and bismuth oxychloride and / or titanium dioxide on mica. Z is particularly advantageous. B. the gloss pigment listed under CIN 77163.

The following pearlescent pigment types based on mica / metal oxide are also advantageous:

Z are particularly preferred. B. those available from Merck under the trade names Timiron, Colorona or Dichrona

Pearlescent pigments.

The list of the pearlescent pigments mentioned is of course not intended to be limiting. Advantageous in the sense of the present invention

Pearlescent pigments are available in numerous ways known per se. For example, other substrates besides mica can be coated with other metal oxides, such as. B. silica and the like. Are advantageous for. B. with TiO ₂ and Fe ₂ O ₃ coated SiO ₂ particles ("Ronaspheren"), which are sold by Merck and are particularly suitable for the optical reduction of fine wrinkles.

It can also be advantageous to do without a substrate such as mica. Pearlescent pigments which are produced using SiO ₂ are particularly preferred. Such pigments, which can also have gonichromatic effects, are z. B. available under the trade name Sicopearl Fantastico from BASF.

Pigments from Engelhard / Mearl based on calcium sodium borosilicate, which are coated with titanium dioxide, can also be used advantageously. These are available under the name Reflecks.

Due to their particle size of 40-80 μm, they have a glitter effect in addition to the color.

Also particularly advantageous are effect pigments, which come in various forms under the trade name Metasomes Standard / Glitter

Colors (yellow, red, green, blue) are available from Flora Tech.

The glitter particles are in mixtures with various auxiliaries and

Dyes (such as dyes with the Color Index (Cl)

Numbers 19140, 77007, 77289, 77491).

The dyes and pigments can be present either individually or in a mixture and can be coated with one another, with different coating effects generally causing different color effects. The total amount of dyes and coloring pigments is advantageously from the range of z. B.

0.1% by weight to 30% by weight, preferably from 0.5 to 15% by weight, in particular from 1.0 to 10% by weight, in each case based on the total weight of the preparations. All compounds or components that can be used in the preparations are either known and commercially available or can be synthesized by known methods.

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

As a form of application of the preparations according to the invention, e.g. called: solutions, suspensions, emulsions, PIT emulsions, pastes, ointments, gels, creams, lotions, powders, soaps, surfactant-containing cleaning preparations, oils, aerosols and sprays. Other forms of application are e.g. Sticks, shampoos and shower baths. Any customary carrier substances, auxiliary substances and optionally further active substances can be added to the preparation.

Preferred additives come from the group of preservatives, antioxidants, stabilizers, solubilizers, vitamins, colorants, odor improvers. Ointments, pastes, creams and gels can contain the usual carriers, e.g. animal and vegetable fats, waxes, paraffins, starch, tragacanth, cellulose derivatives, polyethylene glycols, silicones, bentonites, silica, talc and zinc oxide or mixtures of these substances. Powders and sprays can contain the usual carriers, e.g. Milk sugar, talc, silica, aluminum hydroxide, calcium silicate and polyamide powder or mixtures of these substances. Sprays can also contain the usual propellants, e.g. Chlorofluorocarbons, propane / butane or dimethyl ether.

Solutions and emulsions can contain the usual carriers such as solvents, solubilizers and emulsifiers, e.g. Water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1, 3-butyl glycol, oils, especially cottonseed oil, peanut oil, corn oil, olive oil, castor oil and sesame oil, glycerol fatty acid esters, polyethylene glycols and fatty acid esters of sorbitol contain these substances.

Suspensions can be the usual carriers such as liquid diluents, e.g. water, ethanol or propylene glycol, suspending agents, eg ethoxylated isostearyl alcohols, polyoxyethylene sorbitol esters and

Contain polyoxyethylene sorbitan esters, microcrystalline cellulose, aluminum meta-hydroxide, bentonite, agar-agar and tragacanth or mixtures of these substances. Soaps can contain the usual carriers such as alkali salts of fatty acids,

Contain salts of fatty acid semiesters, fatty acid protein hydrolyzates, isothionates, lanolin, fatty alcohol, vegetable oils, vegetable extracts, glycerol, sugar or mixtures of these substances. Surfactant-containing cleaning products can contain the usual carriers such as salts of fatty alcohol sulfates, fatty alcohol ether sulfates, sulfoberstein acid half-esters, fatty acid protein hydrolysates, isothionates, imidazolinium derivatives, methyl thaiates, sarcosinates, fatty acid amide ether sulfates, alkyl amidobetaine, fatty alcohol ethoxylates, fatty alcohol ethoxylates Contain glycerin fatty acid esters or mixtures of these substances.

Face and body oils can use the usual carriers such as

contain synthetic oils such as fatty acid esters, fatty alcohols, silicone oils, natural oils such as vegetable oils and oily plant extracts, paraffin oils, lanolin oils or mixtures of these substances.

Other typical cosmetic forms of application are also lipsticks, lip care sticks, mascara, eyeliner, eye shadows, blush, powder, emulsion and wax make-up as well as sun protection, pre-sun and after-sun preparations.

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

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

Preparation is used. The lipid phase can advantageously be selected from the following group of substances:

Mineral oils, mineral waxes

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

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

Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes,

Diphenylpolysiloxanes and mixed forms thereof.

The oil phase of the emulsions, oleogels or hydrodispersions or lipodispersions in the sense of the present invention is advantageously selected from the group of esters from saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 3 to 30 carbon atoms and saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 3 to 30 carbon atoms, from the group of the esters of aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 3 to 30 carbon atoms Atoms. Such ester oils can then advantageously be selected from the group of isopropyl myristate, isopropyl palmitate, isopropyl stearate, isopropyl oleate, n-butyl stearate, n-hexyl laurate, n-decyl oleate, isooctyl stearate, isononyl stearate, isononylisononanoate, 2-ethyl-2-ethylhexyl palate 2-octyldodecyl palmitate, oleyl oleate, olerlerucate, erucyl oleate, erucylerucate as well as synthetic, semi-synthetic and natural mixtures of such esters, e.g. B. Jojoba oil.

Furthermore, the oil phase can advantageously be chosen from the group of branched and unbranched hydrocarbons and waxes, silicone oils, dialkyl ethers, the group of saturated or unsaturated, branched or unbranched alcohols, and also fatty acid triglycerides, especially the triglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 8 to 24, in particular 12-18 C atoms. The fatty acid triglycerides can for example be advantageously selected from the group of synthetic, semi-synthetic and natural oils, e.g. 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 can also be used advantageously for the purposes of the present invention. It may also be advantageous to use waxes, for example cetyl palmitate, as the sole lipid component of the oil phase.

The oil phase is selected from the group 2-Ethylhexylisostea- advantageous rat, octyldodecanol, isotridecyl isononanoate, isoeicosane, 2-ethylhexyl cocoate, C ₂ -, caprylic-capric acid triglyceride ₁₅ -alkyl, dicapryl ether.

Particularly advantageous are mixtures of C _{_2-15} -alkyl and

2-ethylhexyl isostearate, mixtures of C ₁₂ -i ₅ alkyl benzoate and isotridecyl isononanoate and mixtures of Ci ₂ -i ₅ alkyl benzoate, 2-ethylhexyl isostearate and isotridecyl isononanoate.

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

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

Silicone oil to be used according to the invention. However, other silicone oils can also be used advantageously for the purposes of the present invention, for example hexamethylcyclotrisiloxane, polydimethylsiloxane, poly (methylphenylsiloxane). Mixtures of cyclomethicone and isotridecyl isononanoate, cyclomethicone and 2-ethylhexyl isostearate are also particularly advantageous.

The aqueous phase of the preparations according to the invention advantageously advantageously contains alcohols, diols or polyols of low C number, and also their ethers, preferably ethanol, isopropanol, propylene glycol,

Glycerin, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether, diethylene glycol monomethyl or monoethyl ether and similar products, furthermore alcohols of low C number, e.g. As ethanol, isopropanol, 1, 2-propanediol, glycerol and in particular one or more thickeners, which one or which can advantageously be selected from the group

Silicon dioxide, aluminum silicates, polysaccharides or their derivatives, e.g. Hyaluronic acid, xanthan gum, hydroxypropylmethyl cellulose, particularly advantageously from the group of polyacrylates, preferably a polyacrylate from the group of so-called carbopoles, for example carbopoles of types 980, 981, 1382, 2984, 5984, each individually or in combination.

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

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

In a preferred embodiment, the preparations according to the invention contain hydrophilic surfactants. The hydrophilic surfactants are preferably selected from the group consisting of alkyl glucosides, acyl lactylates, betaines and cocoamphoacetate.

Alkyl glylcosides which are used particularly advantageously according to the invention are selected from the group octylglucopyranoside, nonylglucopyranoside, decyl glucopyranoside, undecylglucopyranoside, dodecylglucopyranoside, tetra-decylglucopyranoside and hexadecylglucopyranoside.

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

The acyl lactylates are in turn advantageously selected from the group of substances which are characterized by the structural formula

CH ₃ R ¹ -CO-CH

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

Company.

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

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

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

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

The preparations according to the invention are advantageously characterized in that the hydrophilic surfactant or surfactants in concentrations of 0.01-20% by weight, preferably 0.05-10% by weight, particularly preferably 0.1-5% by weight , in each case based on the total weight of the composition, is or are present. For use, the cosmetic and dermatological preparations according to the invention are applied to the skin and / or the hair in a sufficient amount in the manner customary for cosmetics.

Cosmetic and dermatological preparations according to the invention can be in various forms. So you can z. Legs

Solution, an anhydrous preparation, an emulsion or microemulsion of the water-in-oil (W / O) or oil-in-water (O / W) type, a multiple emulsion, for example of the Waser-in-ÖI-in type -Water

(W / O / W), a gel, a solid stick, an ointment or an aerosol. It is also advantageous to give ectoine in an encapsulated form, e.g. B. in collagen matrices and other common encapsulation materials, e.g. B. as cellulose encapsulation, encapsulated in gelatin, wax matrices or liposomal. In particular wax matrices like those in the

DE-OS 43 08 282 described, have proven to be cheap

exposed. Emulsions are preferred. O / W emulsins particularly preferred. Emulsions, W / O emulsions and O / W emulsions are available in the usual way.

For example, the known W / O and O / W emulsifiers can be used as emulsifiers. It is advantageous to use other customary co-emulsifiers in the preferred O / W emulsions according to the invention.

According to the invention, O / W emulsifiers are advantageously chosen as co-emulsifiers, primarily 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 ¹ , or if isoalkyl derivatives are present, the preferred HLB value of such emulsifiers can also be lower or higher.

It is advantageous to choose the fatty alcohol ethoxylates from the group of the ethoxylated stearyl alcohols, cetyl alcohols, cetylstearyl alcohols (cetearyl alcohols). Particularly preferred are: polyethylene glycol (13) stearyl ether (steareth-13), polyethylene glycol (14) stearyl ether (steareth-14), polyethylene glycol (15) stearyl ether (steareth-15),

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

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

Polyethylene glycol (16) isocetyl ether (isoceteth-16), polyethylene glycol (17) - isocetyl ether (isoceteth-17), polyethylene glycol (18) isocetyl ether (isoceteth-18), polyethylene glycol (19) isocetyl ether (isoceteth-19), polyethylene glycol (20 ) isocetyl ether (isoceteth-20), polyethylene glycol (12) oleyl ether (oleth-12), polyethylene glycol (13) oleyl ether (oleth-13), polyethylene glycol (14) oleyl ether (oleth-14), polyethylene glycol (15) oleyl ether (oleth -15), polyethylene glycol (12) lauryl ether (Laureth-12), polyethylene glycol (12) - isolauryl ether (isolaureth-12), polyethylene glycol (13) cetylstearyl ether (ceteareth-13), polyethylene glycol (14) cetylstearyl ether (ceteareth-14), polyethylene glycol (15) cetyl stearyl ether (ceteareth-15), polyethylene glycol (16) cetyl stearyl ether (ceteareth-16), polyethylene glycol (17) - cetyl stearyl ether (ceteareth-17), polyethylene glycol (18) cetyl stearyl ether (ceteareth-18), polyethylene glycol (19) cetyl stearyl ether (Ceteareth-19), polyethylene glycol (20) cetyistearyl ether (Ceteareth-20).

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

Polyethylene glycol (20) stearate, polyethylene glycol (21) stearate,

Polyethylene glycol (22) stearate, polyethylene glycol (23) stearate,

Polyethylene glycol (24) stearate, polyethylene glycol (25) stearate,

Polyethylene glycol (12) isostearate, polyethylene glycol (13) isostearate,

Polyethylene glycol (14) isostearate, polyethylene glycol (15) isostearate,

Polyethylene glycol (16) isostearate, polyethylene glycol (17) isostearate,

Polyethylene glycol (18) isostearate, polyethylene glycol (19) isostearate,

Polyethylene glycol (20) isostearate, polyethylene glycol (21) isostearate,

Polyethylene glycol (22) isostearate, polyethylene glycol (23) isostearate,

Polyethylene 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 (19) oleate,

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

It is also favorable to choose 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) sorbitan monooleate.

Optional W / O emulsifiers which may be advantageous according to the invention are: fatty alcohols with 8 to 30 carbon atoms, monoglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 8 to 24, in particular 12-18 C. Atoms, diglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 8 to 24, in particular 12-18 C atoms, monoglycerol ethers saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 8 to 24, in particular 12-18 C atoms, diglycerol ethers of saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 8 to 24, in particular 12-18 C atoms, propylene glycol ester of saturated and / or unsaturated, branched and / or unbranched ter alkane carboxylic acids with a chain length of 8 to 24, in particular 12-18 C atoms, and sorbitan esters of saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 8 to 24, in particular 12-18 C atoms. Particularly advantageous W / O emulsifiers are glyceryl monostearate,

Glyceryl monoisostearate, glyceryl monomyristate, glyceryl monooleate, diglyceryl monostearate, Diglycerylmonoisostearat, propylene glycol monostearate, propylene glycol monoisostearate alcohol, propylene glycol monocaprylate, propylene glycol monolaurate, sorbitan monoisostearate, sorbitan monolaurate, sorbitan monocaprylate, Sorbitanmonoisooleat, 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.

Preparations preferred according to the invention are particularly suitable for protecting human skin against aging processes and against oxidative stress, i.e. against damage by radicals, such as e.g. generated by solar radiation, heat or other influences. In doing so, it harbors various, usually for this application

dosage forms used. It can be used in particular as a lotion or emulsion, such as a cream or milk (O / W, W / O, O / W / O, W / O / W), in the form of oily-alcoholic, oily-aqueous or aqueous-alcoholic gels or solutions, are available as solid pins or are made up as aerosol.

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

Thickeners, softeners, wetting agents, surfactants, emulsifiers, preservatives, anti-foaming agents, perfumes, waxes, lanolin, blowing agents, dyes and / or pigments which color the agent itself or the skin, and others commonly used in cosmetics Ingredients. An oil, wax or other fatty substance, a low monoalcohol or a low polyol or mixtures thereof can be used as the dispersing or solubilizing agent. To the particularly

preferred monoalcohols or polyols include ethanol, i-propanol, propylene glycol, glycerin and sorbitol.

A preferred embodiment of the invention is an emulsion which is present as a protective cream or milk and, in addition to the compound or compounds of the formula I, 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 Contains water.

Further preferred embodiments are oily lotions based on natural or synthetic oils and waxes, lanolin, fatty acid esters, in particular triglycerides of fatty acids, or 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 according to the invention can also be in the form of an alcoholic gel which contains one or more lower alcohols or polyols, such as ethanol, propylene glycol or glycerol, and one Thickeners 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 fat bodies. If a preparation is made up as an aerosol, the usual propellants, such as alkanes, fluoroalkanes and

Chlorofluoroalkanes.

The cosmetic preparation can also be used to protect the hair against photochemical damage to prevent changes Color shades, discoloration or mechanical damage

prevent. In this case, it is suitably packaged as a shampoo, lotion, gel or emulsion for rinsing, the respective preparation being applied before or after shampooing, before or after dyeing or decoloring or before or after the perm. It can also be a preparation as a lotion or gel for hairdressing and

Treat, be selected as a lotion or gel for brushing or laying a water wave, as a hair varnish, permanent wave agent, dye or decolorizer of the hair. In addition to the compound or compounds of the formula I, the preparation with light protection properties can contain various adjuvants used in this type of agent, such as surfactants, thickeners, polymers, plasticizers,

Preservatives, foam stabilizers, electrolytes, organic solvents, silicone derivatives, oils, waxes, anti-greasing agents, dyes and / or pigments that color the agent itself or the hair or other ingredients commonly used for hair care.

Further objects of the present invention are a method for producing a preparation, which is characterized in that at least one compound of formula I with residues as above

described with a cosmetic or dermatological or for

Food or household products suitable carrier is mixed, and the use of a compound of formula I for the preparation of a preparation. The preparations according to the invention can be prepared using

Techniques are made that are well known to those skilled in the art.

The mixing can result in dissolving, emulsifying or dispersing the compound of the formula I in the carrier.

It has also been found that compounds of the formula I can have a stabilizing effect on the preparation. When using in

corresponding products therefore remain stable longer and do not change their appearance. In particular, even with prolonged use or storage, the effectiveness of the ingredients remains, e.g. B. vitamins. Among other things, this is particularly advantageous in the case of compositions for protecting the skin against the action of UV rays, since these cosmetics are exposed to particularly high levels of exposure to UV radiation. The positive effects of compounds of the formula I result in their particular suitability for use in cosmetic or pharmaceutical preparations.

The properties of compounds of the formula I are equally positive for use in foods or as food supplements or as “functional food”

The explanations given for foods also apply analogously to food supplements and to "functional food". The foods which can be enriched according to the present invention with one or more compounds of the formula I include all materials which are suitable for consumption by animals or for consumption by animals People are suitable, for example vitamins and provitamins thereof, fats, minerals or amino acids ". (The food can be solid or liquid, ie it can be in the form of a drink).

Accordingly, the present invention furthermore relates to the use of a compound of the formula I as a food additive for human or animal nutrition, and to preparations which

Food or nutritional supplements are included and appropriate carriers.

Foodstuffs which can be enriched with one or more compounds of the formula I according to the present invention are, for example, foods which come from a single natural source, such as Sugar, unsweetened juice, nectar or puree from a single plant species, e.g. unsweetened apple juice (e.g. a mixture of different types of apple juice), grapefruit juice, orange juice, apple compote, apricot nectar, tomato juice, tomato sauce,

Tomato puree, etc. Other examples of foods made according to the present invention with one or more compounds of the formula I can be enriched are grain or cereals from a single plant species and materials which are produced from such plant species, such as, for example, cereal syrup, rye flour, wheat flour or oat bran. Mixtures of such foods are also suitable, for example, to be enriched with one or more compounds of the formula I according to the present invention

MultiVitamin preparations, mineral mixtures or sugared juice. Further examples of foods which can be enriched with one or more compounds of the formula I according to the present invention are food preparations, for example prepared cereals, pastries, mixed drinks, specially prepared for children

Called foods, such as yogurt, diet foods, low-calorie foods or animal feed.

The foods which can be enriched according to the present invention with one or more compounds of the formula I thus comprise all edible combinations of carbohydrates, lipids, proteins, inorganic elements, trace elements,

Vitamins, water or active metabolites from plants and animals. The foods which can be enriched with one or more compounds of formula I according to the present invention are preferably administered orally, e.g. in the form of dishes, pills, tablets, capsules, powders, syrups, solutions or suspensions. The foods of the invention enriched with one or more compounds of formula I can be prepared using techniques that are well known to those skilled in the art.

Furthermore, compounds of the formula I have only a weakly pronounced inherent color. The weakly pronounced inherent color is e.g. This is of great advantage if the ingredients' own color of the ingredients is undesirable for aesthetic reasons.

The proportion of the compounds of the formula I in the preparation is preferably from 0.01 to 20% by weight, particularly preferably from 0.05 to 10% by weight and particularly preferably from 0.1 to 5% by weight, based on the entire preparation. The proportion of the compounds of the formula I in the preparation is very particularly preferably from 0.1 to 2% by weight, based on the overall preparation. The use of a compound of formula I as a skin-binding UV filter is particularly preferred.

It is also preferred to use a compound of the formula I as a skin-tanning active ingredient.

Even without further explanations, it is assumed that a person skilled in the art can use the above description to the greatest extent.

Examples

Example 1: Reaction of erythrulose with (E) - (4-methoxy) - cinnamic acid chloride

In a three-necked flask, a solution of erythrulose (9.16 g 76.3 mmol, 3 eq.) In abs. Pyridine (250 ml_) a solution of (E) - (4-methoxy) - cinnamic acid chloride (5.0 Og ₁ 25.4 mmol) in abs. Dichloromethane (75 mL) at 0-5 ⁰ C slowly added dropwise with stirring. Is then stirred for 1 hour at 1O ⁰ C and then for 5 h at room temperature. The solvent is then distilled off and the remaining crude product is taken up in water (100 ml) and extracted with ethyl acetate (3x100 ml). The combined organic phases are washed with water (2x50 mL)

washed and dried over magnesium sulfate. That after

Distilling off the ethyl acetate i. Vac. remaining crude product is recrystallized from ethanol (20 mL). The fancy

The product is filtered off and washed with ethanol (5 mL). The product is a mixture of the 3 mono-esters (E) -3- (4-methoxy-phenyl) - acrylic acid 3,4-dihydroxy-2-oxo-butyl ester, (E) -3- (4 -Methoxy-phenyl) - acrylic acid 3,4-dihydroxy-2-oxo-butyl ester and (E) -3- (4-methoxy-phenyl) - acrylic acid 3-hydroxy-1-hydroxymethyl-2-oxo-propyl ester.

Example 2: 2-cyano-3,3-diphenyl-acrylic acid 2,4-dihydroxy-3-oxobutyl ester is obtained from 2-cyano-3,3-diphenylacryl chloride in accordance with the procedure according to Example 1.

Example 3: Lotion (W / O) for application to the skin

% By weight

Polyg lycery l-2-d ipoly hydoxystea rat 5.0

Beeswax 0.5

Zinc stearate 0.5

Hexyl laurate 9.0

Cetyl isononanoate 6.0

Shea butter 0.5 DL-α-tocopherol acetate 1.0

Product from one of Examples 1-2 0.5

B glycerin 5.0

Magnesium sulfate heptahydrate 1.0

Preservatives q.s.

Water, demineralized ad 100

Preparation Phase A is heated to 75 ° C and phase B to 80 ⁰ C. Phase B is slowly added to phase A with stirring. After homogenization, the mixture is cooled with stirring. Be at a temperature of 40 ⁰ C.

Perfume added. The following are used as preservatives:

0.05% propyl 4-hydroxybenzoate

0.15% methyl 4-hydroxybenzoate Example 4: Lotion (W / O) for application to the skin

% By weight

A P Poollvyαgllvycceerrvyll - 22 - ddiiDpoollvyhhvyddrrooxxvysstteeaarraatt 5.0

Beeswax 0.5

Zinc stearate 0.5

Hexyl laurate 9.0

Cetyl isononanoate 6.0

Shea butter 0.5

DL-α-tocopherol acetate 1.0

B Product from one of Examples 1-2 1, 0

Glycerin 5.0

Magnesium sulfate heptahydrate 1.0

Preservative qs Water, demineralized ad 100

Manufacturing

Phase A is heated to 75 ⁰ C and phase B to 8O ⁰ C. Phase B is slowly added to phase A with stirring. After homogenization, the mixture is cooled with stirring. Be at a temperature of 40 ⁰ C.

Perfume added.

The following are used as preservatives:

0.05% propyl 4-hydroxybenzoate

0.15% methyl 4-hydroxybenzoate

Example 5: Lotion (W / O) for application to the skin:

% By weight

Product from one of Examples 1-2 1.0

Polyglyceryl-2-dipolyhydroxystearate 5.0

Beeswax 0.5

Zinc stearate 0.5

Hexyl laurate 9.0

Cetyl isononanoate 6.0

Shea butter 0.5

DL-α-tocopherol acetate 1.0

5,7-dihydroxy-2-methyl-chromen-4-one 1, 0

B glycerin 5.0

Magnesium sulfate heptahydrate 1.0

Preservatives q.s.

Water, demineralized ad 100 Manufacturing

Phase A is heated to 75 ° C and phase B to 8O ⁰ C. Phase B is slowly added to phase A with stirring. After homogenization, the mixture is cooled with stirring. Be at a temperature of 40 ⁰ C.

Perfume added.

The following are used as preservatives:

0.05% propyl 4-hydroxybenzoate

0.15% methyl 4-hydroxybenzoate

Example 6: Cream (O / W) containing Ectoin wt.%

Paraffin, low viscosity (1) 8.0

Isopropyl myristate (1) 4.0

Mirasil CM5 (2) 3.0

Stearic acid (1) 3.0

Arlacel 165 V (3) 5.0

Product from one of Examples 1-2 1, 0

B glycerin (87%) (1) 3.0

Germaben Il (4) 0.5

Water, demineralized ad 100

RonaCare ™ Ectoin (1) 1, 0

Manufacturing

**

First, phases A and B are heated separately to 75 ° C. Then phase A is slowly added to phase B with stirring and stirred until a homogeneous mixture is formed. After homogenization of the emulsion, the mixture is cooled to 30 ^° C. with stirring. Then will heated to 35 ° C, phase C added and stirred until homogeneous.

Sources of supply

(1) Merck KGaA

(2) Rhodia

(3) Uniqema

(4) ISP Example 7: Topical composition as a W / O emulsion

% By weight

A Isolan PDI (2) 3.0

Paraffin oil, fl. (1) 17.0

Isopropyl myristate 5.0

Beeswax 0.2

Cutina HR (2) 0.3

Product from one of Examples 1-2 1, 0

B water, demineralized ad 100

Glycerin (87%) 4.0

Magnesium sulfate 1.0

Germaben H-E (3) 1, 0

RonaCare ™ LPO (1) 2.0

Manufacturing

Phases A and B are heated to 75 ° C. Phase B is under

Stir added to phase A. Then the mixture at

Homogenize 9000 rpm for 2 min. With the Turrax. The mixture obtained is cooled to 30 to 35 ° C. and C is stirred in. Sources of supply

(1) Merck KGaA

(2) Goldschmidt AG

(3) ISP

Example 8: Preparations

The following are examples of formulations for cosmetic preparations which contain compounds selected from Examples 1 and 2. The designation of the connections takes place according to the information in the description. For the rest, the INCI names of the commercially available compounds are given. UV-Pearl, OMC stands for the preparation with the INCI name:

Water (for EU: Aqua), ethylhexyl methoxycinnamate, silica, PVP, chlorophenesin, BHT; this preparation is commercially available under the name Eusolex DarmUV Pearl ™ OMC from Merck KGaA, Darmstadt.

The other UV pearls listed in the tables are each composed analogously, with OMC being replaced by the specified UV filters.

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

Table 1 (continued)

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

Table 3: Gels, numbers in% by weight

Claims

1. Compound according to formula I.

wherein

X represents O ₁ NH or N-alkyl,

Y stands for O, NH or N-alkyl

Z represents O ₁ NH or N-alkyl

Sp ₁ Sp ^' , Sp ^" can be the same or different and stand for -H ₁ - (CH ₂ J _n -, - (CH ₂ )" - C (= O) - (CHz) o- or - (CH ₂ ) _n -C (= O) -

n, o, p, q stand for an integer independently selected from the range starting with O and ending with

40 and

A ₁ A ^' and A ^" stand for a substituent which absorbs UV radiation and has a conjugated π-electron system of at least 4π electrons, wherein A ₁ A ^' and A ^" in turn with one or more groups -Sp-X-CH ₂ -C (= O) -CH ₂ -OH substituted and may be the same or different and where A ₁ A ^' and A ^" are omitted at the positions where Sp ₁ Sp ^' or Sp ^" are H.

2. A compound according to claim 1, characterized in that X ₁ Y and / or Z are O.

3. A compound according to claim 1 and / or 2, characterized in that Sp-A and / or Sp ^' -A ^' and / or Sp "-A ^" stand for C = O.

4. Connection according to one of claims 1 to 3, characterized

characterized in that it is a 1, 3,4-tri, 1, 3-di, 1,4-di, 3,4-di, 1-mono, 3-mono or 4-monoester who is dealing with erythrulose.

5. Connection according to one of claims 1 to 4, characterized

characterized that it is a 1-mono, 3-mono or 4-monoester of erythrulose.

6. Connection according to one of claims 1 to 5, characterized

characterized that it is a 4-monoester of erythrulose.

7. Connection according to one of claims 1 to 6, characterized

marked that it is a compound from the following group:

8. Preparation containing a carrier, characterized in that the preparation contains 0.001 to 99% by weight of at least one compound of the formula I according to Claims 1 to 7 or its topically tolerable salts and / or derivatives.

9. Preparation containing a carrier, characterized in that the one or more compounds of the formula I in amounts of 0.01 to 20% by weight, preferably 0.05 to 10% by weight and

particularly preferably 0.1 to 5% by weight are contained in the preparation.

10. Preparation according to at least one of the preceding claims, characterized in that the preparation contains one or more antioxidants and / or one or more further UV filters and / or one or more self-tanners.

11. Process for the preparation of compounds according to formula I with

Residues according to at least one or more of claims 1 to 7, wherein X, Y and Z are O _1, characterized in that erythrulose or an erythrulose derivative in which a hydroxyl group is provided with a protective function with an acid chloride

R- (CH ₂ ) _m - (C = O) CI is implemented.

12. Use of a compound according to formula I or one

Preparation according to at least one of claims 8 to 10 for the prophylaxis against time and / or light-induced aging processes of human skin or human hair, in particular for

Prophylaxis against dry skin, wrinkling and / or

Pigment disorders, and / or for pigmentation control and / or for reducing or preventing damaging effects of UV rays on the skin.

13. Use of a compound according to formula I or one

Preparation according to at least one of claims 8 to 10 for the prophylaxis against or reduction of skin imperfections, such as wrinkles, fine lines, rough or large-pored skin.

14. Use for the preparation of a preparation according to at least

one of claims 8 to 10, characterized in that at least one compound of formula I with residues as described above is mixed with a cosmetically or dermatologically or carrier suitable for food or household products.

15. Use of at least one compound according to formula I or a preparation according to at least one of claims 8 to 10 for Care, preservation or improvement of the general

Condition of the skin or hair.

16. Use of a compound of formula I according to one of the

Claims 1 to 7 as a UV filter and / or as a skin-binding UV filter.

17. Use of a compound of formula I according to one of the

Claims 1 to 7 as a tanning agent.