WO2003080015A1 - Cosmetic or dermatological formulations containing 9-retinal and/or 9-retinal alkanolamine schiff base - Google Patents

Abstract

The invention relates to cosmetic or dermatological preparations containing 9-retinal and/or 9-retinal alkanolamine Schiff base of structural formula (I), wherein R = R'(OH)n, branched or unbranched alcanol. The use of 9-retinal and/or 9-retinal alkanolamine Schiff base leads to the induction and intensification of tanning mechanisms of the skin and intensification of hair color.

Description

 description

Cosmetic or dermatological formulations containing 9-retinal and / or

9-retinal alkanolamine Schiff base

The present invention relates to cosmetic or dermatological preparations containing 9-retinal and / or 9-retinal-alkanolamine Schiff base of the structural formula

wobei R = ROH, verzweigte oder unverzweigte Alkanole darstellen. Die Verwendung Zubereitungen enthaltend 9-Retinal und/oder 9-Retinal-alkanolamin Schiffsche Base führt zur Induktion und Intensivierung der Bräunungsmechanismen der Haut und zur Intensivierung der Haarfarbe.

where R = ROH, branched or unbranched alkanols. The use of preparations containing 9-retinal and / or 9-retinal-alkanolamine Schiff base leads to the induction and intensification of the tanning mechanisms of the skin and to the intensification of the hair color.

The damaging effect of the ultraviolet part of solar radiation on the skin is generally known. While rays with a wavelength shorter than 290 nm (the so-called UVC range) are absorbed by the ozone layer in the earth's atmosphere, rays in the range between 290 nm and 320 nm, the so-called UVB range, cause erythema simple sunburn or even more or less severe burns on the skin.

The narrower range around 308 nm is given as a maximum of the erythema effectiveness of sunlight.

Numerous compounds are known to protect against UVB radiation, most of which are derivatives of 3-benzylidene camphor, 4-aminobenzoic acid, cinnamic acid, salicylic acid, benzophenone and also 2-phenylbenzimidazole.

It is also important to have filter substances available for the range between about 320 nm and about 400 nm, the so-called UVA range, because of that Rays can cause damage. It has been shown that UVA radiation damages the elastic and collagen fibers of the connective tissue, which causes the skin to age prematurely, and that it is to be seen as the cause of numerous phototoxic and photoallergic reactions. The damaging influence of UVB radiation can be intensified by UV-A radiation.

UVA radiation can also cause skin damage by u. a. the skin's own keratin or elastin is damaged. This reduces the skin's elasticity and water retention capacity, i.e. the skin becomes less supple and tends to wrinkle. This type of wrinkling is also known as light-related skin aging. The strikingly high incidence of skin cancer in areas exposed to strong sunlight shows that damage to the genetic information in the cells is apparently also caused by sunlight.

However, UV radiation can also lead to photochemical reactions, in which case the photochemical reaction products interfere with the skin's metabolism.

Mostly such photochemical reaction products are radical compounds, e.g. Hydroxyl radicals. Undefined radical photo products, which are created in the skin itself, can also display uncontrolled subsequent reactions due to their high reactivity. But also singlet oxygen, a non-radical excited state of the oxygen molecule can occur with UV radiation, just as short-lived epoxies and many others. Singlet oxygen, for example, is characterized by increased reactivity compared to the triplet oxygen normally present (radical ground state). However, there are also excited, reactive (radical) triplet states of the oxygen molecule. Such processes are significantly involved in light-related skin aging (including wrinkling) through oxidative damage to various skin structures.

UV radiation also belongs to ionizing radiation. There is therefore a risk that ionic species also develop when exposed to UV, which in turn can then oxidatively intervene in the biochemical processes.

The pigmentation of the human skin is essentially caused by the presence of melanin. Melanin and its breakdown products (melanoids), carotene, The degree of bleeding as well as the nature and thickness of the stratum corneum and other skin layers make skin tones of practically white (with reduced filling or in the absence of blood vessels) or yellowish over light brown-reddish, bluish to brown different shades and finally almost black appear. The individual skin regions show different depths of color tint due to different amounts of melanin.

The natural melanin protects the skin from penetrating UV radiation. The number of melanin granules produced in the melanocytes determines whether the skin is light or dark. With strong pigmentation (e.g. in colored people, but also in fair-skinned people after some UV radiation), melanin can also be found in the stratum spinosum and even in the stratum corneum. It weakens the UV radiation by up to approx. 90% before it reaches the corium.

As characteristic cell organelles, melanocytes contain melanosomes, in which the melanin is formed. When stimulated by UV radiation, among other things, melanin is increasingly formed. This is ultimately transported via the living layers of the epidermis (keratinocytes) into the homolayer (comeocytes) and causes the more or less pronounced brown to brown-black skin color. Melanin is formed as the final stage of an oxidative process in which tyrosine, with the help of the enzyme tyrosinase, is converted into brown to brown-black eumelanins (DHICA and DHI melanin) or with the participation of sulfur-containing compounds to reddish pheomelanin. DHICA and DHI melanin are produced via the common intermediate stages dopaquinone and dopachrome. The latter is implemented, partly with the participation of further enzymes, either in indole-5,6-quinone carboxylic acid or in indole-5,6-quinone, from which the two eumelanins mentioned arise. The formation of phaeomelanin occurs, among other things, via the intermediates dopaquinone and cysteinyldopa.

In addition to various functions of the skin's own melanin (also "detoxification'V connection of toxic substances / pharmaceuticals, etc.), the function of melanin as a natural UV filter to protect against damaging UV rays and the antioxidant function of melanin as protection against reactive oxygen species (oxidative Stress), which can occur, among other things, from the sun's rays, is very important for the skin, including in relation to homeostasis, avoidance of skin aging, avoidance of sunburn, etc. This should not just be a cosmetic benefit in terms of increased tanning due to the increased melanin synthesis in the skin after topical application of compounds which increase the melanogenesis, but also provide additional protection through the various protective functions of melanin.

Depending on the sensitivity to light, the following skin types are generally distinguished:

Skin type I never tans, always gets a sunburn. Skin type II hardly tans, easily gets sunburned. Skin type III tans well on average. Skin type IV tans lightly and persistently, almost never gets sunburned. Skin type V dark, often almost black skin, never gets sunburned.

The natural shielding of harmful UV radiation is a tangible advantage of natural skin tanning. For some decades now, a "healthy" skin color has been a sign of sporting activity in particular and is therefore regarded as desirable by a wide range of consumers. Representatives of skin types I and II who want to enjoy such a skin tint are therefore dependent on self-tanning preparations anyway But representatives of skin type III who are not too exposed to the risks of sunbathing and still want to look tanned are grateful target groups for self-tanning preparations.

The easiest way to give your skin a brown hue is to apply appropriately colored make-up or make-up preparations. However, only those parts of the body that are covered by the colored preparations are of course stained. With the help of washable make-up preparations, a light skin tint can be achieved (e.g. extracts from fresh green walnut shells, henna). A disadvantage of the make-up is therefore the time-consuming procedure of applying. Another disadvantage is that they rub off heavily on textiles such as shirt collars or blouses. In addition, the different dyes can have different allergenic potency and can even be irritating to the skin.

Artificial skin tanning can be achieved by cosmetic or medical means, whereby the following approaches play a role:

Through regular intake of carotene preparations, carotene is stored in the subcutaneous fatty tissue, the skin gradually turns orange to yellow-brown. The staining can also be done by chemical modification of the skin's skin layer with so-called self-tanning preparations. The most important active ingredient is dihydroxyacetone (DHA). The skin tanning achieved in this way cannot be washed off and is only removed with the normal desquamation of the skin (after approx. 10-15 days). Dihydroxyacetone can be called ketotriose and reacts as a reducing sugar with the amino acids of the skin or the free amino and imino groups of keratin via a series of intermediates in the sense of a Maillard reaction to brown-colored substances, so-called melanoids, which occasionally also melanoidins to be named.

A particular disadvantage of tanning with dihydroxyacetone is that, in contrast to "sun-tanned" skin, the tanned skin is not protected against sunburn. Another disadvantage of dihydroxyacetone is that it, especially under the influence of ultraviolet radiation, albeit in mostly releases small amounts of formaldehyde, so there was an urgent need to find ways in which the decomposition of dihydroxyacetone can be effectively countered.

An object of the present invention is to find alternatives to DHA as a self-tanning agent which do not have any disadvantageous properties as are known from DHA.

Staining by self-tanners takes place without exposure to sunlight. In contrast to this, so-called “pre-tan products” or “tan promoters” are also offered, which have to be applied before exposure to the sun. These preparations then turn yellow in the sun, which is said to lead to a slight brown-yellow coloring of the epidermis, which additionally reinforces the "tan".

Another type of artificial tanning, which is also completely independent of UV light, can be brought about by the hormones, which are also released in the body as a result of (natural) UV radiation and ultimately stimulate the melanocytes to synthesize melanin. In this context, descendants of proopiomelanocortin (POMC) such as aMSH and synthetic variants (such as NDP) may be mentioned, some of which have much higher activity than natural aMSH. Although these hormones can generally bring about a tan, their use in cosmetics is forbidden, since they are clearly pharmacological acting substances (hormones), which should not be widely used without medical indication.

The object of the present invention was therefore to remedy the disadvantages of the prior art.

In addition to skin health and skin care, hair care is an extremely intensively researched area in cosmetics.

Hair is the thread-like, thread-like, almost universal skin appendage (missing from the palms of the hands, soles of the feet, extended sides of the toes, end of the fingers); distinguished as long hair (the head, beard, armpit, pubic hair = Capilli, Barba, Hirci or Pubes; in men also chest hair), short, bristle hair (Supercilia, Cilia, Vibrissae, Tragi) and wool hair (Lanugo, Velus hair ). The structure of all these hairs is roughly similar: the central hair mark (from epithelial cells with eosinophilic granules of the trichohyaline granule), surrounded by the hair cortex (from horny cells; contains pigments) and the cuticle (cuticle pili; coreless epidermal layer) and of layers of the epithelial and connective tissue sheath.

The hair is divided into the hair shaft protruding from the skin and the oblique hair root reaching into the subcutis, the layers of which correspond approximately to those of the epidermis. The thickened lower end of the root, the hair bulb, sits on a vascular connective tissue cone, the hair papilla, protruding into it (both as a hair floor). The onion is in the initial (= anagen) phase, the cyclically repeating hair formation layered onion-like due to constant new formation of cells due to its layer close to the papilla (matrix), later closed, bulbous, completely horny (piston hair) and finally, in the end (= telogen) phase, displaced towards the follicle opening by a new hair - starting from a newly formed hair papilla.

Melanin is responsible for the personal hair color. Melanin is formed in the melanocytes, cells that are associated with the keratinocytes of the hair bulb

Hair marks occur. As characteristic cell organelles, melanocytes contain melanosomes, in which the melanin is formed. This will go over the long Dendrites of the melanocytes are transferred into the keratinocytes of the precortical matrix and produce the more or less pronounced blonde to brown-black hair color. Melanin is formed as the final stage of an oxidative process in which tyrosine is converted into brown to brown-black eumelanins (DHICA and DHI melanin) or with the participation of sulfur-containing compounds to reddish pheomelanin with the help of the enzyme tyrosinase. DHICA and DHI melanin are produced via the common intermediate stages dopaquinone and dopachrome. The latter is implemented, partly with the participation of further enzymes, either in indole-5,6-quinone carboxylic acid or in indole-5,6-quinone, from which the two eumelanins mentioned arise. The formation of phaeomelanin occurs, among other things, via the intermediates dopaquinone and cysteinyldopa. Cysteine is also necessary if the phaeomelanin is to be created for blonde and reddish hair.

Eumelanin is the black-brown pigment. It is mainly about the depth of color of the hair. In brown and black hair it occurs in clearly recognizable granules.

Phaeomelanin is the red pigment. It is responsible for light blonde, blonde and red hair. The structure of this melanin is much finer and smaller. The different hair colors result from the different proportions of the melanin types:

• Blond hair contains little eumelanin and a lot of phaeomelanin.

• Dark hair contains a lot of eumelanin and little phaeomelanin.

• Red hair also has little eumelanin and a lot of phaeomelanin.

• All shades of hair in between arise from different mixing ratios of the two melanin types.

The pigment formation process can only proceed if sufficient tyrosinase is available. This enzyme is formed less frequently with increasing age. This gradually leads to gray hair. The reason: with little tyrosinase, less and less tyrosine is formed. The production of melanin also decreases. The missing melanin is replaced by the storage of air bubbles. The hair appears gray. This process is usually insidious. It begins at the temples and then extends to the entire hair on the head. Then it hits the beard and eyebrows. Finally, all of the body's hair is gray.

Medically, gray hair is called canities. There are several ways of graying. Premature graying, from the age of 20, is also called Canities praecox.

Symptoms of canities, or symptomatic graying of the hair, can have various causes. This includes:

Pernicious anemia (vitamin B deficiency anemia), severe endocrinological disorders, e.g. B. in thyroid diseases. acute, febrile diseases,

Drug side effects, • cosmetics,

Metals.

The coloring of hair, especially of living human hair, using natural dyes, as has been known for the dye henna since ancient times, and which has been pushed into the background for years in favor of synthetic dyes, has been the subject of a new one for some years interest. The red hue created by henna is a disadvantage.

With increasing age, the melanin production that causes the hair color decreases: the hair becomes gray or white. It is a cosmetic wish of some consumers to reverse this process or to let it run more slowly. For this purpose, the cosmetic industry uses lead acetate in some countries, which is toxic and is therefore prohibited in the European Cosmetics Regulation. This lead acetate is preferably applied to the hair as a solution and remains there for a long time without being washed off. For dyeing keratin fibers, e.g. B. hair, wool or fur, generally either direct dyes or oxidation dyes, which are formed by oxidative coupling of one or more developer components with one another or with one or more coupler components, are used. Coupler and developer components are also referred to as oxidation dye precursors.

Primary aromatic amines with a further free or substituted hydroxyl or amino group in the para or ortho position, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives and 2,4,5,6-tetraaminopyrimidine and derivatives thereof are usually used as developer components used.

Special representatives are, for example, p-phenylenediamine, p-toluenediamine, 2,4,5,6-tetraaminopyrimidine, p-aminophenol, N, N-bis (2-hydroxyethyl) -p-phenylenediamine, 2- (2,5-diaminophenyl ) -ethanol, 2- (2,5-diaminophenoxy) -ethanol, 1-phenyl-3-carboxyamido-4-amino-pyrazolon-5, 4-amino-3-methylphenol, 2-aminomethyl-4-aminophenol, 2- Hydroxy-methyl-4-aminophenol, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6-triamino-4-hydroxypyrimidine.

M-Phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenols are generally used as coupler components. Suitable coupler substances are, in particular, α-naphthol, 1, 5-, 2,7- and 1, 7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 2 , 4-diaminophenoxyethanol, 1-phenyl-3-methylpyrazolon-5, 2,4-dichloro-3-aminophenol, 1, 3-bis (2,4-diaminophenoxy) propane, 2-chlororesorcinol, 4-chlororesorcinol , 2-chloro-6-methyl-3-aminophenol, 2-methylresorcinol and 5-methylresorcinol.

With regard to other conventional dye components, reference is expressly made to the "Dermatology" series, edited by Ch. Culnan, H. Maibach, Marcel Dekker Inc., New York, Basel, 1986, Vol. 7, Ch. Zviak, The Science of Hair Care, Cape. 7, pages 248-250 (direct dyes), and Chap. 8, pages 264-267 (oxidation dyes), as well as the "European Inventory of Cosmetic Raw Materials", 1996, published by the European Commission, available in disk form from the Federal Association of German Industry and Trade Companies for Medicines, Health Care Products and Personal Care Products, Mannheim , With oxidation dyes intensive dyeings can be achieved with good fastness properties, but the development of the color is generally done under the influence of oxidizing agents such. B. H ₂ O ₂ , which in some cases can damage the fiber. Furthermore, some oxidation dye precursors or certain mixtures of

Oxidation dye precursors sometimes have a sensitizing effect on people with sensitive skin. Direct dyes are applied under gentler conditions, but their disadvantage is that the dyeings often have inadequate fastness properties.

The object of the present invention is to improve the independent melanin production of the hair, but without coloring agents and in particular oxidizing agents such. B. H ₂ O _{2 to be} instructed. In addition, the agents must have no or only a very low sensitization potential.

The object of the present invention was therefore to remedy the disadvantages of the prior art.

It has surprisingly been found that cosmetic or dermatological preparations according to one of claims 1 to 10 solve the bundle of tasks.

When looking for a suitable substance which helps to avoid the disadvantages of the prior art listed, the compounds 9-retinal are of the structural formula

and 9-retinal alkanolamine Schiff base of the structural formula A A

synthetisiert worden. R ist ein verzweigter oder unverzweigter Alkanolrest R = R^'(OH)_n, mit R^'= C1 bis C20 Kohlenwasserstoffrest und n=1 - 5. R ist beispielsweise ein Methanol- , Ethanol-, Propanol-, n-Butanol-, i-Butanol-, Pentanol-, neo-Pentanol-, Hexanol-, Heptanol- bzw. Octanolrest. Bevorzugt ist R' ein C1 bis C5 Kohlenwasserstoffrest. Rest R ist weiter bevorzugt gewählt aus den Resten: 1-Amino-Ethan-1 ,2-diol, 2-Amino- Propan-1 ,3-diol, 2-Amino-Propan-1 ,2,3-triol, 3-Amino-Butan-1-ol, 4-Amino-Butan-1 ,2,3- triol, 3-Amino-butan-1 ,4-diol, 3-Amino-butan-1 ,2,4-triol, 3-Amino-Pentan-1-ol, 2-Amino- Butan-1 ,4-diol, 2-Amino-Butan-1 ,3,4-triol, 3-Amino-Pentan-1 ,5-diol, 3-Amino-Pentan- 1 ,2,5-triol.

synthesized. R is a branched or unbranched alkanol radical R = R ^' (OH) _n , with R ^' = C1 to C20 hydrocarbon radical and n = 1-5. R is, for example, a methanol, ethanol, propanol, n-butanol, i -Butanol, pentanol, neo-pentanol, hexanol, heptanol or octanol residue. R 'is preferably a C1 to C5 hydrocarbon radical. R is more preferably selected from the groups: 1-amino-ethane-1,2-diol, 2-amino-propane-1,3-diol, 2-amino-propane-1, 2,3-triol, 3- Amino-butan-1-ol, 4-amino-butane-1, 2,3-triol, 3-amino-butane-1, 4-diol, 3-amino-butane-1, 2,4-triol, 3- Amino-pentan-1-ol, 2-amino-butane-1, 4-diol, 2-amino-butane-1, 3,4-triol, 3-amino-pentane-1, 5-diol, 3-amino- Pentane-1, 2,5-triol.

It has proven to be advantageous if the branched alkanol radical R has more than one hydroxyl group, for example a diol or triol radical. The result is an improved solubility in aqueous systems and associated increased bioavailability of the substance.

In particular 9-retinal ethanolamine Schiff base of structural formula B

B

proves to be an extremely advantageous substance for solving the problems, where R = C ₂ H ₄ OH.

Both 9-retinal and 9-retinal Schiff base have proven to be the only additives as well as a mixture in cosmetic preparations. 9-Retinal Schiff's base has been shown to be particularly advantageous as an additive in cosmetic preparations.

In the chemical literature there is only a quote from the above compound (Jiang, Long; Chin. Chem. Lett. 2 (12), 1991), which does not indicate any use in cosmetic or dermatological formulations can be found. Furthermore, there is no indication in the literature that the compounds according to the invention induce the melanogenesis of the skin and the hair. The name of one of the compounds according to the invention, compound B, is found to be 9-retinalethanolamine Schiff base, retinal- (2-hydroxyethyl) imine or retinalethylene olimine Schiff base, all of which fall under structure B shown. The compound B according to the invention is listed under CAS No. 141271-29-6.

Figure 1: Induction of melanogenesis in primary cultures of human melanocytes over 72 hours with the active ingredient according to the invention

(Retinal- (2-hydroxyethyl) imine; Rl) were incubated. Melanogenesis was quantified using cell lysates using ¹⁴ C-tyrosine

Installation (n = 6).

Intensive research has shown that the compounds according to the invention lead to induction of skin pigmentation in topical cosmetic or dermatological preparations (see Figure 1). Melanogenesis is increased, there is more melanin in the skin, the skin becomes brown and the skin's own protection is physiologically increased. Even when applied topically to hair, the compounds according to the invention in suitable preparations lead to an intensification of the hair color, with which natural graying of the hair can also be avoided and even reversed. The activation of the skin's own tanning and the intensification of hair coloring can of course be done with and without the involvement of UV light.

The compounds according to the invention, corresponding to the structural formulas 9-retinal or A or B, are distinguished, inter alia, by the fact that, after topical application, they induce the formation of skin-specific pigments in the skin, increase the melanin synthesis and in this way intensify tanning of the skin. They are harmless to health, non-irritating and easy to use, and the resulting shade naturally corresponds to that of the natural, healthy skin color. The tan obtained is - since it corresponds to the natural tanning - lightfast and not washable. The preparations according to the invention also surprisingly intensify the tanning of already tanned skin and furthermore delay the bleaching of tanned skin. Another advantage of the present invention results from the protective properties of natural melanin formed in the skin. In addition to various other functions of the skin's own melanin (such as "detoxification" or binding of toxic substances and / or pharmaceuticals etc.), these functions of melanin are also very important for the skin, in particular with regard to homeostasis, the avoidance of Skin aging and the like:

Melanin acts as a natural UV filter to protect against damaging UV rays and also as an antioxidant to protect against reactive oxygen species (oxidative stress), which can occur, among other things, from sun exposure.

Thus, when used according to the invention (i.e. after topical application), there is not only a cosmetic benefit in the sense of increased tanning due to the increased melanin synthesis in the skin, but also an additional benefit due to the various protective benefits of melanin. Accordingly, the compounds 9-retinal and 9-retinal Schiff base according to the invention are outstandingly suitable in cosmetic or dermatological preparations.

The content of the compounds, 9-retinal and / or 9-retinal-alkanolamine Schiff base, is between 0.0001 and 30% by weight, advantageously between 0.01 and 10% by weight, particularly advantageously between 0.02 and 2% by weight .% each based on the total weight of the preparation.

The cosmetic or dermatological preparations according to the invention induce the formation of skin and hair-specific pigments in the skin and the hair, intensify the existing natural and / or artificial tanning of the skin, intensify the natural hair coloring and let the skin tanning and the hair coloring last longer.

In all respects, the formulations according to the invention are extremely satisfactory preparations which are distinguished by a uniform coloring effect. It was not foreseeable for the person skilled in the art that the formulations according to the invention

^{■ be} easier to formulate

^{■ give} the skin and hair a natural look faster and better, make the tanning and hair coloring last longer, work better than moisturizing preparations, better promote smoothing of the skin, are characterized by better care, better sensory properties, such as spreadability on the skin

Skin and hair or the ability to be absorbed into the skin, and ■ would offer better / risk-free protection of the skin and hair (against UV radiation) than the preparations of the prior art. In addition, the formulations according to the invention surprisingly have no hormonal effects.

The cosmetic and / or dermatological formulations according to the invention can be composed as usual and can be used in particular for the treatment and care of the skin and / or hair, as a make-up product in decorative cosmetics or as a sunscreen or so-called pre- or after-preparation. Correspondingly, depending on their structure, the formulations according to the invention can be used, for example, as skin protection cream, face cream, cleansing milk, sunscreen lotion, nutrient cream, day or night cream, etc.

It is also possible and advantageous in the sense of the present invention to insert the active ingredient used according to the invention in aqueous systems or surfactant preparations for cleaning and care of the skin and hair. This includes shower gels, shampoos but also conditioners, hair care treatments, hair rinses, hair tonics, sprays etc.

It is of course known to the person skilled in the art that sophisticated cosmetic compositions are usually inconceivable without the customary auxiliaries and additives. These include, for example, consistency agents, fillers, perfumes, dyes, emulsifiers, additional active ingredients such as vitamins or proteins, light stabilizers, stabilizers, insect repellents, alcohol, water, salts, antimicrobial, proteolytic or keratolytically active substances, etc.

It is also advantageous to present the active ingredient (s) according to the invention in encapsulated form, for example in collagen matrices and other customary encapsulation materials, such as, for example, cyclic oligosaccharides (in particular alpha, beta, HP-beta, random-beta, gamma-cyclodextrin), where alpha, beta or gamma-cyclodextrins can be used as encapsulation material. Furthermore, it may be advantageous to present the active ingredient systems according to the invention in the form of cellulose encapsulations, in gelatin, wax matrices or encapsulated in liposomes. When encapsulated with cyclodextrins, it is assumed that the cyclodextrin skeletons act as the host molecule and the active ingredient according to the invention acts as the guest molecule. For the preparation, cyclodextrins are dissolved in water and the active ingredient according to the invention, 9-retinal and / or 9-retinal Schiff base, is added. The molecular adduct then precipitates as a solid and can be subjected to the usual cleaning and preparation steps. It is known that cyclodextrin-guest complexes in an appropriate solvent (eg water) are in equilibrium between the specific guest-cyclodextrin complex and the dissociated form, it being possible for cyclodextrin and guest to be separated to a certain extent. Such balance systems are also advantageous in the sense of the present invention.

Mutatis mutandis, corresponding requirements apply to the formulation of medical preparations.

Medical topical compositions in the sense of the present invention generally contain one or more drugs in effective concentration. For the sake of simplicity, reference is made to the legal provisions of the Federal Republic of Germany (e.g. cosmetics regulation, food and drug law) for a clear distinction between cosmetic and medical use and corresponding products. It is also advantageous to add the active ingredient used according to the invention as an additive to preparations which already contain other active ingredients for other purposes.

Those cosmetic and dermatological preparations which are in the form of a sunscreen are particularly preferred. These can advantageously additionally contain at least one further UVA filter and / or at least one further UVB filter and / or at least one inorganic pigment, preferably an inorganic micropigment. Surprisingly, cosmetic and dermatological preparations according to the invention are able to prolong the natural tanning process.

It was also astonishing that cosmetic and dermatological formulations according to the invention are able to serve for the treatment of hypopigmentation (vitiligo, uneven pigmentation in aging skin, etc.).

According to the invention, the cosmetic and dermatological preparations can contain cosmetic auxiliaries as are usually used in such preparations, e.g. Preservatives, bactericides, perfumes, substances to prevent foaming, dyes, pigments that have a coloring effect, thickeners, moisturizing and / or moisturizing substances, fats, oils, waxes or other common components of a cosmetic or dermatological formulation such as alcohols, polyols, Polymers, foam stabilizers, electrolytes, organic solvents, silicone derivatives or moisturizers.

Moisturizers are substances or mixtures of substances that give cosmetic or dermatological preparations the property of reducing the release of moisture from the horny layer (also called transepidermal water loss (TEWL)) after application or distribution on the skin surface and / or positively hydrating the horny layer to influence.

Advantageous moisturizers for the purposes of the present invention are, for example, glycerin, lactic acid, pyrrolidone carboxylic acid and urea. Furthermore, it is particularly advantageous to use polymeric moisturizers from the group of water-soluble and / or water-swellable and / or water-gelable polysaccharides. Particularly advantageous are, for example, hyaluronic acid and / or a fucose-rich polysaccharide, which is filed in the Chemical Abstracts under the registration number 178463-23-5 and z. B. under the name Fucogel®1000 from the company SOLABIA S.A. is available.

Glycerin can be used as a moisturizer in the sense of the present application in the range of 0.05-30% by weight, particularly preferably 1-10%. The amounts of cosmetic or dermatological auxiliary substances and carriers and perfume to be used in each case can easily be determined by a person skilled in the art depending on the type of product in question by simply trying them out.

An additional content of antioxidants in the preparations according to the invention is generally preferred. According to the invention, all the antioxidants suitable or customary for cosmetic and / or dermatological applications can be used as favorable antioxidants. It is therefore advantageous to add antioxidants to the preparations according to the invention. The antioxidants are advantageously selected from the group consisting of amino acids (eg glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (eg urocanic acid) and their derivatives, peptides such as D, L-carnosine, D-carnosine, L-car- nosin and its derivatives (e.g. anserine), carotenoids, carotenes (e.g. α-carotene, ß-carotene, lycopene) and their derivatives, chlorogenic acid and their derivatives, lipoic acid and their derivatives (e.g. dihydroliponic acid), aurothioglucose, propylthiouracil and other thiols (e.g. Thioredoxin, glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, γ-linoleyl, cholesteryl and glyceryl esters) as well as their salts, dilauryl thiodipropionate, distearyl thio dipropionate, thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (e.g. buthionine sulfoximines, homocysteine sulfoximine, buthionine sulfones, penta- ion sulfones, xa-, heptathionesulfoximine) 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 (e.g. γ-linolenic acid, oleic acid, oleic acid), folic acid and their derivatives, ubiquinone and ubiquinol and their derivatives, vitamin C and Derivatives (e.g. ascorbyl palmitate, Mg ascorbyl phosphate, ascorbyl acetate), tocopherols and derivatives (e.g. vitamin E acetate), vitamin A and derivatives (vitamin A palmitate) as well as coniferyl benzoate of the benzoin resin, rutinic acid and its derivatives, α-glycosyl rutin, ferulic acid, furfurylidene glucitol, camosin, butylated hydroxytoluene, butylated hydroxyanisole, nordihydroguajak resin acid, nordihydroguajaretic acid, trihydroxybutyrophenone, uric acid and its derivatives, mannose and their derivatives, zinc and their derivatives (eg ZnO, ZnSO ₄ ) selenium and their derivatives (eg selenium methionine), stilbenes and their derivatives (eg stilbene oxide, trans-stilbene oxide) and the derivatives suitable according to the invention (Salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids) of these active ingredients.

The amount of the aforementioned antioxidants (one or more compounds) in the preparations is preferably 0.001 to 30% by weight, particularly preferably 0.05-20% by weight, in particular 1-10% by weight, based on the total weight of the Preparation.

If vitamin E and / or its derivatives represent the antioxidant (s), it is advantageous to choose their respective concentrations from the range of 0.001-10% by weight, based on the total weight of the formulation.

If vitamin A or vitamin A derivatives or carotenes or their derivatives represent the antioxidant or antioxidants, it is advantageous to use their respective concentrations in the range from 0.001-10% by weight, based on the total weight of the formulation, to choose.

Cosmetic or dermatological formulations within the meaning of the present invention can preferably contain, in addition to one or more oil phases, one or more water phases and, for example, in the form of W / O, O / W, W / O W or O / W / O Emulsions are present. Such emulsions can preferably also be a microemulsion, a Pickering emulsion or a sprayable emulsion.

In addition, the formulations according to the invention can also advantageously be in the form of oil-free preparations, such as gels, or as anhydrous preparations.

The formulations according to the invention can furthermore advantageously also contain dihydroxyacetone or nut extracts as well as other substances which are intended to maintain or produce the tan or to additionally reinforce them.

The lipid phase of the emulsions according to the invention can advantageously be selected from the following group of substances:

Mineral oils, mineral waxes - oils, such as triglycerides of capric or caprylic acid, but preferably castor oil; Fats, waxes and other natural and synthetic fat bodies, preferably esters of fatty acids with alcohols with a low C number, for example with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids with a low C number or with fatty acids; - alkyl benzoates;

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

The oil phase of the emulsions, oleogels or hydrodispersions or lipodispersions for the purposes of the present invention 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 C atoms, from the group of esters of aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 3 to 30 C- 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 palmitate Hexyldecyl stearate, 2-octyldodecyl palmitate, oleyl oleate, olerlerucate, erucyl oleate, erucylerucate as well as synthetic, semi-synthetic and natural mixtures of such esters, for example Jojoba oil.

Furthermore, the oil phase can advantageously be 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 also the fatty acid triglycerides, especially the triglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 8 to 24, in particular 12 - 18 carbon atoms. The fatty acid triglycerides can, for example, advantageously be selected from the group of synthetic, semi-synthetic and natural oils, e.g. 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 advantageously selected from the group consisting of 2-ethylhexyl isostearate, octyldodecanol, isotridecyl isononanoate, isoeicosane, 2-ethylhexyl cocoate, C ₂ .i ₅ alkylbenzoate, caprylic capric acid triglyceride, dicaprylyl ether.

Mixtures of C ₁₂ are particularly advantageous. ₁₅ alkyl benzoate and 2-ethylhexyl isostate, mixtures of Cι. _{2 15} alkyl benzoate and isotridecyl isononanoate and mixtures of C ₂ -i ₅ alkyl benzoate, 2-ethylhexyl isostearate and isotridecyl isononanoate.

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

The oil phase can advantageously also 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 advantageously used as the silicone oil to be used according to the invention. However, other silicone oils can also be used advantageously for the purposes of the present invention, for example hexamethylcyclotnsiloxane, 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 optionally advantageously contains

Alcohols, diols or polyols of low C number, and 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 analog products, furthermore alcohols of low C number, for example Ethanol, isopropanol, 1,2-propanediol, glycerol and in particular one or more thickeners, which one or more can advantageously be selected from the group consisting of silicon dioxide, aluminum silicates, polysaccharides or their derivatives, e.g.

Hyaluronic acid, xanthan gum, hydroxypropylmethyl cellulose, especially 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.

UV filter substances can also be added to the preparation according to the invention.

Particularly advantageous UV filter substances which are liquid at room temperature for the purposes of the present invention are homomenthyl salicylate (INCI: homosalate), 2-ethylhexyl-2-cyano-3,3-diphenylacrylate (INCI: octocrylene), 2-ethylhexyl-2-hydroxybenzoate (2- Ethyl hexyl salicylate, octyl salicylate, INCI: octyl salicylate) and esters of cinnamic acid, preferably 4-methoxycinnamic acid (2-ethylhexyl) ester (2-ethylhexyl-4-methoxycinnamate, INCI: octyl methoxycinnamate) and 4-methoxycinnamate isopentyl ester cinnamate, INCI: isoamyl p-methoxycinnamate). Preferred inorganic pigments are metal oxides and / or other metal compounds which are sparingly soluble or insoluble in water, in particular oxides of titanium (TiO ₂ ), zinc (ZnO), iron (e.g. Fe ₂ O ₃ ), zirconium (ZrO ₂ ), silicon ( SiO ₂ ), manganese (e.g. MnO), aluminum (Al ₂ O ₃ ), cerium (e.g. Ce ₂ O ₃ ), mixed oxides of the corresponding metals as well as mixtures of such oxides and the sulfate of barium (BaSO ₄ ). For the purposes of the present invention, the pigments can also advantageously be used in the form of commercially available oily or aqueous predispersions. Dispersing aids and / or solubilizing agents can advantageously be added to these predispersions. According to the invention, the pigments can advantageously be surface-treated ("coated"), for example, a hydrophilic, amphiphilic or hydrophobic character should be formed or retained. This surface treatment can consist in that the pigments are prepared using a thin hydrophilic and / or hydrophobic inorganic and / or organic layer The various surface coatings can also contain water in the sense of the present invention.

Inorganic surface coatings in the sense of the present invention can consist of aluminum oxide (Al ₂ O ₃ ), aluminum hydroxide Al (OH) ₃ , or aluminum oxide hydrate (also: alumina, CAS no .: 1333-84-2), sodium hexametaphosphate (NaPO ₃ ) ₆ , sodium metaphosphate (NaPO ₃ ) _n , silicon dioxide (Siö ₂ ) (also: silica, CAS No .: 7631-86- 9), or iron oxide (Fe ₂ O ₃ ). These inorganic surface coatings can occur alone, in combination and / or in combination with organic coating materials.

Organic surface coatings in the sense of the present invention can consist of vegetable or animal aluminum stearate, vegetable or animal stearic acid, lauric acid, dimethylpolysiloxane (also: dimethicone), methylpolysiloxane (methicone), simethicone (a mixture of dimethylpolysiloxane with an average chain length of 200 to 350 dimethylsiloxane Units and silica gel) or alginic acid. These organic surface coatings can occur alone, in combination and / or in combination with inorganic coating materials.

Ziήkoxidparticles suitable according to the invention and predispersions of zinc oxide particles are available under the following trade names from the listed companies:

Suitable titanium dioxide particles and predispersions of titanium dioxide particles are available under the following trade names from the companies listed:

Advantageous UV-A filter substances for the purposes of the present invention are dibenzoyl methane derivatives, in particular 4- (tert-butyl) -4'-methoxydibenzoyl methane (CAS No. 70356-09-1), which is available from Givaudan under the Parsol brand ^® 1789 and is sold by Merck under the trade name Eusolex® 9020.

Advantageous further UV filter substances in the sense of the present invention are sulfonated, water-soluble UV filters, such as. B .:

Phenylene-1,4-bis (2-benzimidazyl) -3,3'-5,5'-tetrasulfonic acid and its salts, especially the corresponding sodium, potassium or ethanol ammonium salts, in particular phenylene-1, 4-bis- (2-benzimidazyl) -3,3'-5,5'-tetrasulfonic acid bis-sodium salt with the INCI name bisimidazylate (CAS no .: 180898-37-7), which is available, for example, from Haarmann & Reimer under the trade name Neo Heliopan AP;

• Salts of 2-phenylbenzimidazole-5-sulfonic acid, such as its sodium, potassium or triethanolammonium salt, and the sulfonic acid itself with the INCI name

Phenylbenzimidazole sulfonic acid (CAS No. 27503-81-7), which is available, for example, under the trade name Eusolex 232 from Merck or under Neo Heliopan Hydro from Haarmann &Reimer;

• 1,4-di (2-oxo-10-sulfo-3-bornylidenemethyl) benzene (also: 3,3 '- (1,4-phenylenedimethylene)) bis- (7,7-dimethyl-2- oxo-bicyclo- [2.2.1] hept-1-ylmethane sulfonic acid) and its salts (especially the corresponding 10-sulfato compounds, especially the corresponding sodium, potassium or triethanolammonium salt), which is also known as benzene-1, 4-di (2-oxo-3-bornylidenemethyl-10-sulfonic acid) Benzene-1, 4-di (2-oxo-3-bornylidenemethyl-10-sulfonic acid) has the INCI name Terephtalidene Dicampher Sulfonic Acid (CAS. -No .: 90457-82-2) and is available, for example, under the trade name Mexoryl SX from Chimex; sulfonic acid derivatives of 3-benzylidene camphor, such as 4- (2-oxo-3-bomylidene-methyl) ) benzenesulfonic acid, 2-methyl-5- (2-oxo-3-bomylidenemethyl) sulfonic acid and salts thereof. Advantageous UV filter substances for the purposes of the present invention are also so-called broadband filters, ie filter substances which contain both UV-A and UV Absorb B radiation.

Advantageous broadband filters or UV-B filter substances are, for example, triazine derivatives, such as. B. • 2,4-bis - {[4- (2-ethylhexyloxy) -2-hydroxy] phenyl} -6- (4-methoxyphenyl) -1,3,5-triazine (INCI: Aniso Triazine) , which is available under the trade name Tinosorb® S from CIBA-Chemicals GmbH;

• Diethylhexylbutylamidotriazon (INCI: Diethylhexylbutamidotriazone), which is available under the trade name UVASORB HEB from Sigma 3V; ^• 4,4 ', 4 "- (1,3,5-triazine-2,4,6-triyltriimino) tris-benzoic acid tris (2-ethylhexyl ester), also: 2,4,6-tris [anilino - (p-carbo-2'-ethyl-1'-hexyloxy)] - 1, 3,5-triazine (INCI: Ethylhexyl Triazone), which is sold by BASF Aktiengesellschaft under the trade name UVINUL® T 150. An advantageous broadband filter For the purposes of the present invention, the 2,2'-methylene-bis- (6- (2H-benzotriazol-2-yl) -4- (1, 1, 3,3-tetramethylbutyl) phenol), which is available under the trade name Tinosorb® M from CIBA-Chemicals GmbH.

Another advantageous broadband filter for the purposes of the present invention is 2- (2H-benzotriazol-2-yl) -4-methyl-6- [2-methyl-3- [1, 3,3,3-tetramethyl-1 - [( trimethylsilyl) oxy] disiloxanyl] propyl] phenol (CAS no .: 155633-54-8) with the INCI name Drometrizole Trisiloxane, which is available under the trade name Mexoryl® XL from Chimex.

The other UV filter substances can be oil-soluble or water-soluble. Advantageous oil-soluble UV-B and / or broadband filter substances in the sense of the present invention are e.g. B .:

■ 3-benzylidene camphor derivatives, preferably 3- (4-methylbenzylidene) camphor, 3-benzylidene camphor;

■ 4-aminobenzoic acid derivatives, preferably 4- (dimethylamino) benzoic acid (2-ethylhexyl) ester, 4- (dimethylamino) benzoic acid amyl ester; ^■ Derivatives of benzophenone, preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone

^■ as well as UV filters bound to polymers.

^■ 3- (4- (2,2-bis ethoxycarbonylvinyl) phenoxy) propenyl) - methoxysiloxan / dimethylsiloxane - copolymer which is obtainable for example from Hoffmann La Roche under the trade name Parsol SLX.

Advantageous water-soluble filter substances are e.g. B .:

Sulfonic acid derivatives of 3-benzylidene camphor, such as. B. 4- (2-oxo-3-bomylidene methyl) benzenesulfonic acid, 2-methyl-5- (2-oxo-3-bornylidene methyl) sulfonic acid and salts thereof. A further light protection filter substance according to the invention to be used advantageously is ethylhexyl-2-cyano-3,3-diphenylacrylate, obtainable (octocrylene) from BASF under the name Uvinul ^® N 539th

Particularly advantageous preparations within the meaning of the present invention, which are distinguished by a high or very high UV-A and / or UV-B protection, preferably also contain further UV-A and in addition to the filter substance (s) according to the invention / or broadband filter, in particular dibenzoylmethane derivatives [for example the 4- (tert-butyl) -4'-methoxydibenzoylmethane], phenylene-1, 4-bis (2-benzimidazyl) -3,3'-5,5'-tetrasulfonic acid and / or their salts, the 1,4-di (2-oxo-10-sulfo-3-bornylidenemethyl) benzene and / or its salts and / or the 2,4-bis - {[4- (2-ethyl- hexyloxy) -2-hydroxy] phenyl} -6- (4-methoxyphenyl) -1, 3,5-triazine, in each case individually or in any combination with one another.

The list of the UV filters mentioned, which can be used in the sense of the present invention, should of course not be limiting. The preparations according to the invention advantageously contain the substances which absorb UV radiation in the UV-A and / or UV-B range in a total amount of, for. B. 0.1 wt .-% to 30 wt .-%, preferably 0.5 to 20 wt .-%, in particular 1, 0 to 15.0 wt .-%, each based on the total weight of the preparations to cosmetic To provide preparations that protect the hair or skin from the entire range of ultraviolet radiation. They can also serve as a sunscreen for the hair.

The formulations according to the invention can advantageously, although not necessarily, also be used in combination with UV radiation - be it with artificially produced or natural ultraviolet rays - for example to increase natural tanning or to achieve a particularly long-lasting tanning.

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

The preparation of the compounds according to the invention, 9-retinal or 9-retinal Schiff base, is known to the person skilled in the art. The 9-retinal Schiff base is prepared by reacting retinal, in particular all-trans retinal, with the desired alkanolamine of the general formula NH2-R ^' -OH, where R ^{' is} a hydrocarbon radical having 1 to 20 carbon atoms.

The production is based, for example, on the production of 9-retinalethanolamine Schiff base of structural formula B.

dargestellt.

shown.

Ethanol abs. / Mol sieve / 0 ° C

H ₂ O

B

For example, 500 mg of all-trans retinal are dissolved in 30 ml of absolute ethanol in a 50 ml flask under a nitrogen atmosphere and 1.5 g of molecular sieve (4 Å) are added. The solution is cooled to 0 ° C., 1.07 g of ethanolamine are added dropwise and the mixture is stirred for four hours. The solution is filtered with abs. Washed diethyl ether, concentrated and dried. The remaining ethanolamine is removed using an oil pump. 9-Retinalethanolamine Schiff base of formula B is obtained. The reaction is carried out in the same way at higher temperatures, for example at 10 ° C., 20 ° C. or 25 ° C.

The following examples are intended to illustrate the present invention without restricting it. Unless otherwise stated, all quantities, parts and percentages are based on the weight and the total amount or on the total weight of the preparations.

Examples

1. PIT emulsions

2. Examples of O / W cream

3. Examples of O / W cream

Octoxyglycerin 0,30 1,00 0,50

Octoxyglycerin 0.30 1.00 0.50

Glycerin 3.00 7.50 7.50 2.50

Glycine soy 1.00 1.50

Magnesium sulfate 1.00 0.50 0.50

Magnesium chloride 1.00 0.70

Tocopherol acetate 0.50 0.25 1.00

Retinal (2-hydroxyethyl) imine 0.15 0.08 0.5 1.00 0.80

Preservatives q.s. q.s. q.s. q.s. q.s.

Ethanol 3.00 1.50 1.00

Perfume q.s. q.s. q.s. q.s. q.s.

Water ad. ad. ad. ad. ad. 100 100 100 100 100

5. Examples of W / O emulsions

6. Examples of hydrodispersions

7. Example (gel cream):

8. Example (W / O cream)

10. Example (spray formulation)

11. Example (shower bath)

Sodium laureth sulfate 33.00

Potassium-cocoyl-hydrolyzed collagen 11.00 (30%)

Der pH-Wert wird auf 3,0 eingestellt.

The pH is adjusted to 3.0.

14. Example (conditioner shampoo with perfume)

15. Example (clear conditioner shampoo)

16. Example (clear light shampoo with volume effect)

Claims

claims 1. Cosmetic or dermatological preparations containing 9-retinal of the structural formula

and / or 9-retinal alkanolamine Schiff base of the structural formula

where R = R ^' (OH) _{n is} branched or unbranched alkanols, with R ^' = C1 to C20 hydrocarbon radical and n = 1-5. 2. Cosmetic or dermatological preparations according to claim 1 containing 9-retinal alkanolamine Schiff base, characterized in that R ^'is a C1 to C5 hydrocarbon radical. 3. Cosmetic or dermatological preparations according to claim 1 or 2 containing 9-retinal alkanolamine Schiff base of the structural formula

4. Preparation according to claims 1 to 3, characterized in that the content of 9-retinal and / or 9-retinal-alkanolamine Schiff base. Between 0.0001 and 30 wt.%, In particular. Between 0.01 and 10 wt .%, particularly advantageously between 0.02 and 2% by weight, based on the total weight of the preparation. 5. Preparation according to claims 1 to 4, characterized in that 9-retinal and / or 9-retinal alkanolamine Schiff base is contained in encapsulated form. 6. Preparation according to claim 5, characterized in that the encapsulation material consists of collagen matrices, cyclic oligosaccharides, alpha-, beta-, HP-beta, random-me-beta or gamma-cyclodextrin, cellulose, gelatin, wax matrices or liposomes. 7. Preparation according to one of claims 1 to 6, characterized in that at least one UVA filter and / or at least one UVB filter and / or at least one inorganic pigment, preferably an inorganic micropigment, is contained. 8. Preparation according to one of claims 1 to 7, characterized in that in addition antioxidants in a proportion of 0.001 to 30% by weight, particularly preferably 0.05-20% by weight, in particular 0.1-10% by weight, based on the total weight of the preparation. 9. Preparation according to one of claims 1 to 8, characterized in that in addition preservatives, bactericides, perfumes, substances for preventing foaming, dyes, fillers, pigments which have a coloring effect, thickeners, moisturizing and / or moisturizing substances, fats , oils, waxes, alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents, silicone derivatives, moisturizers, vitamins, proteins, light stabilizers, stabilizers, insect repellents, water, salts, antimicrobial, proteolytically or keratolytically active substances, drugs or other common components of a cosmetic or dermatological formulation are included. 10. Preparation according to claim 9, characterized in that glycerin is added as a moisturizer in the range from 0.05 to 30% by weight, particularly preferably 1 to 10% by weight, based on the total mass of the preparation. 11. Use of the preparation according to one of claims 1 to 10 as an aqueous system and / or surfactant preparation for cleaning and care of the skin and / or hair. 12. Use of the preparation according to one of claims 1 to 10 as a multiple emulsion, microemulsion, Pickering emulsion or sprayable emulsion. 13. Use of the preparation according to one of claims 1 to 10 as a presun, a sunscreen or an aftersun formulation. 14. Use of the preparation according to one of claims 1 to 10 for topical use on skin and / or hair. 15. Use of the preparation according to one of claims 1 to 10 for tanning the skin. 16. Use of the preparation according to claim 1 to 10 to increase melanin synthesis in the skin. 17. Use of the preparation according to one of claims 1 to 10 to prolong the brown color of the skin. 18. Use of the preparation according to one of claims 1 to 10 for protecting the skin from oxidative stress. 19. Use of the preparation according to one of claims 1 to 10 for protecting the skin against chronological and light-related skin aging. 20. Use of the preparation according to one of claims 1 to 10 for intensifying the hair color. 21. Use of the preparation according to one of claims 1 to 10 to prevent graying of the hair and / or to protect the hair from fading due to sunlight. 22. Use of the preparation according to one of claims 1 to 21 as a shower gel, shampoo, conditioner, hair care treatment, hair conditioner, hair tonic, hair spray, makeup, skin protection, face, cleaning, sun protection, nutrient, day or night cream, gel, or lotion or cleansing preparation.