EP1677752A1 - Produits pour la peau et/ou les cheveux contenant des cyclohexenes tetrasubstitues - Google Patents

Produits pour la peau et/ou les cheveux contenant des cyclohexenes tetrasubstitues

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Publication number
EP1677752A1
EP1677752A1 EP04740896A EP04740896A EP1677752A1 EP 1677752 A1 EP1677752 A1 EP 1677752A1 EP 04740896 A EP04740896 A EP 04740896A EP 04740896 A EP04740896 A EP 04740896A EP 1677752 A1 EP1677752 A1 EP 1677752A1
Authority
EP
European Patent Office
Prior art keywords
skin
hair
acid
agent according
methyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP04740896A
Other languages
German (de)
English (en)
Inventor
Rainer Wolber
Cathrin Scherner
Karen Tom Dieck
Jens-Peter Vietzke
Kathrin Schlenz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Beiersdorf AG
Original Assignee
Beiersdorf AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Beiersdorf AG filed Critical Beiersdorf AG
Publication of EP1677752A1 publication Critical patent/EP1677752A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/04—Preparations for care of the skin for chemically tanning the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/70—Biological properties of the composition as a whole

Definitions

  • the present invention relates to agents for use on the skin and / or hair, in particular for increasing skin tanning and melanin synthesis in the skin or hair.
  • the invention encompasses cosmetic or dermatological preparations containing 4-times substituted cyclohexene compounds.
  • the use of the preparations leads to the induction and intensification of the tanning mechanisms of the skin, to the intensification of the hair color and thus also to an increase in skin or hair protection.
  • UVG range rays with a wavelength shorter than 290 nm
  • UVB range rays in the range between 290 nm and 320 nm, the so-called UVB range, cause erythema , a simple sunburn or even more or less severe burns on the skin.
  • UVA range 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, since their rays can also cause damage. It has been shown that U VA radiation damages the elastic and collagen fibers of the connective tissue, which causes the skin to age prematurely, and that it can be seen as the cause of numerous phototoxic and photoallergic reactions is. 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. As a result, elasticity and water
  • UV radiation can also lead to photochemical reactions, in which case the photochemical reaction products interfere with the skin's metabolism.
  • Such photochemical reaction products are predominantly 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.
  • Singlet oxygen a non-radically excited state of the oxygen molecule can also occur under UV radiation, as can short-lived epoxies and many others.
  • Singlet oxygen for example, is characterized by increased reactivity compared to the triplet oxygen that is normally present (radical ground state). However, there are also excited, reactive (radical) triplet states of the. Oxygen molecule.
  • Such processes are very significantly involved in light-related skin aging (including wrinkling) due to 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 human skin is essentially caused by the presence of melanin.
  • Melanin and its breakdown products (melanoids), carotene, the degree of blood circulation and the nature and thickness of the stratum comeum and other skin layers leave 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 appear almost black.
  • the individual skin regions show different depths of color due to different amounts of melanin.
  • 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.
  • melanin is also in the stratum spinosum and even
  • Hnhd-01938 (203-058-1) in the stratum corneum. It weakens the UV radiation by up to approx. 90% before it reaches the corium.
  • 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 into the horny layer (corneocytes) via the living layers of the epidermis (keratinocytes) 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 with the help of the enzyme tyrosinase.
  • DHICA and DHI melanin are produced via the common intermediate stages dopaquinone and d ⁇ pachrom.
  • 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.
  • melanin In addition to various functions of the skin's own melanin, such as "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 due to solar radiation, among other things, is very important for the skin, also with regard to homeostasis, avoidance of skin aging, avoidance of sunburn, etc. This should not only result in a cosmetic benefit in the sense of increased tanning due to the increased Melanin synthesis in the skin after topical application of compounds which increase the melanogenesis result in additional protection through the various protective functions of melanin.
  • oxidative Stress reactive oxygen species
  • the object of the present invention is therefore to provide an agent, in particular a cosmetic or dermatological preparation, which enhances the natural tanning of the skin by means of increased melanin synthesis and at the same time leads to an increased protection of the skin.
  • Skin type I never tans, always gets a sunburn.
  • Skin type II hardly tans, easily gets a sunburn.
  • 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.
  • a "healthy" skin color has also been a sign of sporting activity in particular and is therefore considered 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
  • 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.
  • make-up or make-up 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.
  • the different dyes can have different alfefgenen potency and even irritate the skin.
  • the object of the present invention is therefore also to provide preparations which do not have the disadvantages of make-up tanning preparations.
  • carotene By taking carotene supplements regularly, carotene is stored in the subcutaneous fatty tissue, the skin gradually turns orange to yellow-brown.
  • Hnhd-01938 (203-058-1)
  • 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).
  • DHA dihydroxyacetone
  • 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).
  • Hydroxyacetone can be called etotriose and reacts as a reducing sugar with the amino acids of the skin or the free amino and i mino groups of keratin via a series of intermediates in the sense of a Maillard reaction to brown-colored substances, so-called melanoids, which are sometimes also called melanoidins.
  • a particular disadvantage of tanning with dihydroxyacetone is that the skin tanned with it, in contrast to "sun-tanned" skin, is not protected against sunburn.
  • dihydroxyacetone releases formaldehyde, in particular under the influence of ultraviolet radiation, even if mostly in small amounts. It was therefore an urgent need to have 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.
  • US 5093360 describes cosmetic or pharmaceutical preparations which contain retinal (vitamin A aldehyde) and / or their derivatives. Retinal or its derivatives are used in combination with active agents or as additives in various preparations to remedy dermatological errors.
  • Retinal or its derivatives are used in combination with active agents or as additives in various preparations to remedy dermatological errors.
  • tanning preparations which contain retinal or their derivatives in addition to the tanning agents.
  • retinal or its derivatives alone have an effect on skin tanning.
  • Hn d-01938 (203-058-1) 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.
  • proopiomelanocortin such as aMSH
  • synthetic variants such as N DP
  • these hormones can generally bring about a tan, their use in cosmetics is forbidden since they are clearly pharmacologically active substances (hormones) * which should not be used widely without medical indication.
  • Hair is the thread-like, almost universal (attached to the palms of the hands, soles of the feet, extensor sides of the toe and end of the fingers) skin appendages;
  • 25 horny cells contains pigments) and the cuticle (cuticle pili; seedless epidermis layer) as well as layers of the epithelial and connective tissue hair sheath.
  • the hair is divided into the hair shaft protruding from the skin and the sloping 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).
  • Melanin is responsible for the personal hair color.
  • Melanin is formed in the melanocytes, cells that occur in the hair bulb in association with the keratinocytes of the hair market.
  • Melanocytes contain - as characteristic cell organelles - melanosomes in which the melanin is formed. This is transferred via the long dendrites of the melanocytes into the keratinocytes of the precortical matrix and creates 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 with the help of the enzyme tyrosinase via several intermediate stages to the brown to brown-black eumelanins (DHICA and DHI melanin) or with the participation of.
  • DHICA and DHI melanin brown to brown-black eumelanins
  • phaeomelanin sulfur-containing compounds is converted to reddish phaeomelanin.
  • DHICA and DHI melanin are produced via the common intermediate stages dopaquinone and dopach rom. The latter is converted, partly with the participation of further enzymes, either into indole-5,6-quinone carboxylic acid or into indole-5,6-quinone, from which the two called Eumelanine 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 result from different mixing ratios of the two melanin types.
  • Hnhd-01938 (203-058-I)
  • the pigment formation process can only proceed if sufficient tyrosinase is available. This enzyme is produced less frequently with 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.
  • gray hair is called canities.
  • canities There are several ways of graying. Premature graying, from the age of 20, is also called Canities praecox.
  • Symptoms of canities can have various causes. These include: Pernicious anemia (vitamin B deficiency anemia), severe endocrinological disorders, e.g. B. in thyroid diseases. acute, febrile diseases, drug side effects, cosmetics, metals.
  • Pernicious anemia vitamin B deficiency anemia
  • severe endocrinological disorders e.g. B. in thyroid diseases. acute, febrile diseases, drug side effects, cosmetics, metals.
  • H ⁇ hd-01938 (203-058-1) preferably applied to the hair as a solution and remains there for a long time without being washed off.
  • keratin fibers e.g. B. hair, wool or fur
  • 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
  • Coupler and developer components are also referred to as oxidation dye precursors.
  • Primary aromatic amines with a further free or substituted hydroxy or amino group in the para or ortho position, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazone derivatives and 2,4,5,6-tetraaminopyrimidine and derivatives thereof are usually used as developer components used.
  • M-Phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenols are generally used as coupler components.
  • Suitable coupler substances are, in particular, ⁇ -naphthol, 1, 5-, 2,7- and 1, 7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 2 , 4-diamine .
  • ophenoxyethanol 1-phenyl-3-methyl-pyrazolon-5, 2,4-dichloro-3-aminophenol, 1, 3-bis (2,4-diaminophenoxy) propane, 2-chlororesorcinol, 4-chlororesorcinol, 2 -Chlor-6-methyl-3-aminophenol, 2-methylresorcinol and 5-methylresorcinol.
  • Hnhd-01938 (203-058-1) European Commission, available in diskette form from the Federal Association of German Industry and Commerce for Medicinal Products, Health Care Products and Personal Care Products, Mannheim.
  • 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 0 2 , which in some cases can result in damage to the fiber. Furthermore, some oxidation dye precursors or v certain mixtures of oxidation dye precursors can have a sensitizing effect sometimes in 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.
  • the agents must have no or only a very low sensitization potential.
  • the invention includes the use of such agents and the compounds according to the invention as agents for increasing the tan or the melanin synthesis in the skin or hair.
  • cosmetic or dermatological preparations contain one or more compounds of the structure
  • R1, R2 and / or R5 are selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxy and / or alkyl carboxylates with alkyl radicals selected from methyl, ethyl , Propyl or butyl, preferably is methyl;
  • R6 and / or R7 are selected from the group consisting of methyl, hydrogen, ethyl, propyl, isopropyl, butyl, tert-butyl, hydroymethyl, hydroxyethyl, hydroxypropyl, hydroxy or alkyl carboxylate, the alkyl radical being selected from methyl, ethyl, propyl or Butyl, methyl is preferred;
  • R4 is selected from carbonyl oxygen, amino acid residues Ala, Ser, Gly, Val, Leu, lle, Pro, Trp, Phe, Met Tyr, Thr, Cys, Asn, Asp, Glu, Lys, Arg, Gin, H, Orn, Sar , Hyl, Hyp, Hse or Hey, preferably Ala, Ser or Gly, - residues of the structure N- (CH 2 ) x -OH, N- (CHR9) x -CH2OH, N- (CH 2 ) x -OCOMe, where each
  • R9 is selected from hydrogen and / or hydroxy
  • R11 is selected from methyl, hydroxymethyl, hydrogen, prop-2-yl, isobutyl, but-2-yl, pyrrolidin-1, 2-diyl, 1 H-indol-3-yl-methyl, benzyl; 2- (methylthio) ethyl, 4-hydroxy-benzyl, 1-hydroxyethyl, mercaptomethyl, 2-amino-2-oxoethyl, carboxymethyl, carboxyethyl, 4-aminobutyl, 3 - ⁇ [amino (imino ) methyl] amino ⁇ propyl, 3-amino-3-oxopropyl, hydrogen and N-Me, 3-aminopropyl, ethyl, 1 H-imidazol-4-yl-methyl, butyl, propyl, 4 -Amino-3-hydroxy-butyl-, 4-hydroxy-pyrrolidin-1, 2-diyl-, hydroxy
  • R12 is selected from mono- to polysaccharides, preferably uniform and / or mixed mono-, di- or trisaccharides, preferably glucose, glycerose, erythrose, threose, ribose, arabinose, lyxose, xylose, ailose, altrose, galactose, gose, idose , Mannose or talose.
  • mono- to polysaccharides preferably uniform and / or mixed mono-, di- or trisaccharides, preferably glucose, glycerose, erythrose, threose, ribose, arabinose, lyxose, xylose, ailose, altrose, galactose, gose, idose , Mannose or talose.
  • the compounds are 9-retinal of the structural formula
  • the substances according to the invention are outstandingly suitable for bringing about increased tanning of the skin.
  • Suitable are all compounds of the structures listed above which the person skilled in the art can select from the respective groups without being inventive.
  • the person skilled in the art will, in particular, be used for cosmetic or dermatological purposes
  • Hnhd-01938 (203-058-1) Choose preferably only those whose tolerability, toxicology and the like, are not critical.
  • the skin's own melanin has various functions, such as "detoxification'V connection of toxic substances / pharmaceuticals.
  • the function of melanin as a natural UV filter for protection against harmful UV rays and the antioxidant function of melanin as protection against reactive oxygen species (oxidative Stress), which can occur due to sun radiation is very important for the skin, also in relation to homeostasis, avoidance of skin aging, avoidance of sunburn, etc. This should not only result in a cosmetic benefit in the sense of increased tanning due to the increased Melanin synthesis in the skin after topical application of compounds which increase the melanogenesis according to the invention also provide additional protection through the various protective functions of melanin.
  • the substances according to the invention are suitable for strengthening the physiological tanning of the skin by means of an increased melanin synthesis and thus also increasing the skin's own protection.
  • a major advantage is that this physiological tanning is achieved without having to be exposed to natural solar radiation with its damaging influences on the skin or that this is only necessary to a comparatively small extent in order to achieve the desired skin tanning.
  • uneven skin pigmentations (“uneven skin tone") are also compensated.
  • the advantage the complexion appears more uniform, which is particularly desirable for aging skin (age spots), melasma and post-inflammatory hyperpigmentation.
  • the invention therefore preferably relates to cosmetic or dermatological preparations containing compounds according to the invention, as defined above.
  • the invention also relates to the use of the preparations thus produced.
  • the compounds according to the invention comprise ring-shaped hydrocarbon compounds, the ring-shaped structure preferably being composed of 6 carbon atoms and being partially to completely unsaturated and additionally having several, in particular 4, hydrocarbon substituents.
  • the compounds according to the invention are simply referred to as tetrasubstituted cyclohexene compounds.
  • 3 substituents are short-chain, preferably consisting of a methyl group (R1, R2 and R5), a further, fourth, substituent (R3), which also consists of
  • a branched and / or partially to completely unsaturated hydrocarbon compound can comprise 1 to 25 carbon atoms, but preferably at least 4 and at most 20 carbon atoms.
  • the end of the “fourth substituent” opposite the annular structure preferably, but not necessarily, has a polar end.
  • the 4-fold substituted compounds according to the invention could be crystallized out as suitable compounds for use on human skin and hair.
  • Three basic building blocks, the cyclohexene ring, the structure and chain length of the radical R3 and its functional groupings or polarities are essential. All of these findings lead to the compounds according to the invention, which the person skilled in the art can select according to structure (I) and any remaining information.
  • the 4-fold substituted cyclohexene compounds according to the invention are known per se, at least from a synthetic point of view, but are not mentioned in connection with their suitability as agents for use on the skin or hair.
  • the person skilled in the art can select a compound from the group of compounds listed in claim 1 as required and even combine it with other compounds in order to achieve the effects which are advantageous according to the invention. It follows from this that the compound according to the invention has the following general structure:
  • R1, R2 and R5 is preferably a methyl radical and R3 in the manner described above creates a C 1 -C 25 radical, preferably a C 4 -C 20 radical, d, which preferably forms a polar at the opposite end Group has.
  • ⁇ / -3,7-dimethyl-9- (2,6,6-trimethylcyclohex-1-en-1-yl) nona-2,4,6,8-tretraen-1-ylidenes] is alanine preferred, characterized by the structure.
  • Hnhd-01938 (203-058-1) wherein R4 represent amino acids bound via an imino functionality, in particular glycine and serine, and R1, R2, R5, R6 and R7 is a methyl radical.
  • R4 represent amino acids bound via an imino functionality, in particular glycine and serine
  • R1, R2, R5, R6 and R7 is a methyl radical.
  • the following synthesis instructions are cited as examples: Rani, Aruna V., Tet Lett, 33, 10, 1992, 1379-1382 and Pshenichnikova, AB, Russ. J. Bioorg. Chem., 22, 11, 1996, 744-747 and Int J. Vitamin and Nutrition Research, 62, 4, 1992, 298-302 and EP 440078 A2. s.
  • connection structure (I) From the connection structure (I), the following preferred connections (IUPAC names) with the specified structures result:
  • R1, R2, R5, R6 and R7 as the methyl radical and R4 as the radical of the structure N-OH.
  • R1, R2, R5, R6 and R7 as the methyl radical
  • connection structure (I) also gives the following
  • acetyl retinyliminoethanol The manufacturing instructions for acetyl retinyliminoethanol are as follows:
  • the mixture is filtered and the solvent is removed on a rotary evaporator.
  • compositions in particular cosmetic or dermatological preparations, lead to the induction of pigmentation of the skin.
  • 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.
  • a melanogenesis assay was carried out after 3 days of incubation of primary normal human melanocytes with test substance versus control.
  • Hnhd-01938 (203-058-1)
  • the compounds according to the invention are distinguished, inter alia, by the fact that, after topical application, they induce the formation of the skin's own pigments in the skin, increase the melanin synthesis and in this way produce an increased tanning of the skin handle, and the resulting shade naturally corresponds to that of the natural healthy skin color.
  • the browning obtained - which corresponds to the natural tanning - is lightfast and cannot be washed off.
  • 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 benefits of natural melanin formed in the skin.
  • melanin 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.
  • agents according to the invention e.g. Cosmetic or dermatological preparations induce the formation of skin and hair-specific pigments in the skin and hair, intensify the existing natural and / or artificial tanning of the skin, compensate for inconsistent pigmentation of the skin, intensify the natural hair coloring and leave the skin tanning as the hair coloring also last longer.
  • 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
  • Hnhd-01938 (203-058-1) ⁇ give the skin and hair a natural look faster and better
  • ⁇ better promote smoothing of the skin, ⁇ are characterized by better care effects
  • ⁇ have better sensory properties, such as, for example, the spreadability on the 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.
  • the formulations according to the invention surprisingly have no hormonal effects.
  • the content of the compounds 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, in each case based on the total weight of the composition.
  • 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.
  • 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.
  • compositions are usually inconceivable without the customary auxiliaries and additives.
  • auxiliaries and additives include, for example, consistency enhancers, 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.
  • Hnhd-01938 (203-058-1) It is also advantageous to present the compound or compounds 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-Me-beta, gamma-cyclodextrin), where, according to the chemical properties known to the person skilled in the art, alpha-, beta- or gamma-cyclodextrins are used as encapsulation material.
  • cyclic oligosaccharides in particular alpha, beta, HP-beta, random-Me-beta, gamma-cyclodextrin
  • the compounds according to the invention may be advantageous to present the compounds according to the invention or their mixtures in the form of cellulose encapsulations, encapsulated in gelatin, wax matrices or liposomally.
  • 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.
  • cyclodextrins are dissolved in water and the active ingredient according to the invention is added. The molecular adduct then precipitates as a solid and can be subjected to the usual cleaning and preparation steps.
  • Medical topical compositions in the sense of the present invention generally contain one or more drugs in effective concentration.
  • the compound (s) according to the invention is also advantageous to add the compound (s) according to the invention as an additive to preparations which already contain other active ingredients for other purposes.
  • the formulations according to the invention are also particularly suitable for combinations with active ingredients which have a positive effect on the condition of the skin. It has been shown that active ingredients to positively influence the aging skin, which reduce the appearance of wrinkles or existing wrinkles. So especially in
  • Hnhd-01938 (203-058-1) Combination with bioquinones, especially ubiquinone Q10, creatine, creatinine, camitin, biotin, isoflavone, cardiolipin, lipoic acid, anti freezing proteins, hop and hop malt extracts.
  • Promotional agents for the restructuring of the connective tissue such as isoflavonoids and isoflavonoid-containing plant extracts such as, for example, soybean and clover extracts, can also be used very well in the formulations according to the invention.
  • formulations are particularly suitable, active ingredients to support skin functions in dry skin, such as vitamin C, biotin, camitin, creatine, propionic acid, green tea extracts, eucalyptus oil, urea and mineral salts such as. B. NaCI, marine minerals and osmolytes such. B. taurine, inositol, betaine, quaternary ammonium compounds to use.
  • active ingredients to support skin functions in dry skin such as vitamin C, biotin, camitin, creatine, propionic acid, green tea extracts, eucalyptus oil, urea and mineral salts such as. B. NaCI, marine minerals and osmolytes such. B. taurine, inositol, betaine, quaternary ammonium compounds to use.
  • active ingredients to support skin functions in dry skin such as vitamin C, biotin, camitin, creatine, propionic acid, green tea extracts, eucalyptus oil, urea and mineral salts
  • Active substances such as sericosides, various extracts of liquorice, licochalcones, in particular licochalocon A, silymarin, silyphos, dexpanthenol, inhibitors of prostaglandin metabolism, in particular cyclooxygenase and leukotriene metabolism, in particular 5-lipoxyenase, but also 5- Lipoxvase inhibitor protein, FLAP.
  • the incorporation of pigmentation modulators also proved to be advantageous. Active substances are to be mentioned here which reduce the pigmentation of the skin and thus lead to a cosmetically desired lightening of the skin and / or reduce the appearance of age spots and / or lighten existing age spots.
  • Examples include tyrosine sulfate, dioic acid (8-hexadecen-1, 16-dicarboxylic acid as well as lipoic acid and liponamide, various extracts of licorice. Kojic acid, HydroGhinon, arbutin, fruit acids, especially alpha-hydroxy acids (AHAs), bearberry (Uvae ursi ), Ursolic acid, ascorbic acid, green tea extracts, aminoguanidine, pyridoxamine.
  • the formulations according to the invention proved to be excellent combination partners for other active ingredients which bring about enhanced or faster tanning of the skin (advanced glycation end products (AGE), lipofuscins, nucleic acid oligonucleotides, Purines and pyrimidines, NO-releasing substances), be it with or without the influence of UV light.
  • AGE glycation end products
  • lipofuscins lipofuscins
  • nucleic acid oligonucleotides nucleic acid oligonucleotides
  • Purines and pyrimidines Purines and pyrimidines
  • NO-releasing substances advanced glycation end products
  • Cosmetic and dermatological preparations in the form of a sunscreen are particularly preferred. These can advantageously also have at least one further UVA filter and / or at least one further UVB filter
  • cosmetic and dermatological preparations according to the invention are able to prolong the natural tanning process.
  • cosmetic and dermatological formulations according to the invention are able to serve for the treatment of hypopigmentation (vitiligo, uneven pigmentation in aging skin, etc.).
  • 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.
  • cosmetic auxiliaries 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 that after application or distribution, the release of moisture from the skin layer on the skin surface (also
  • 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%.
  • antioxidants in the preparations according to the invention are generally preferred. According to the invention, all the antioxidants suitable or customary for cosmetic and / or dermatological applications can be used as favorable antioxidants.
  • antioxidants are advantageously selected from the group consisting of amino acids (for example glycine, histidine, tyrosine, phenylalanine, tryptophan) and their derivatives (in particular N-acetyl-tyrosine, N-acetyl-phenylalanine), imidazoles (for example urocanic acid) and their Derivatives, peptides such as DL-camosin, D-camosin, L-camosin and their derivatives (e.g. anserine), carotenoids, carotenes (e.g.
  • amino acids for example glycine, histidine, tyrosine, phenylalanine, tryptophan
  • imidazoles for example urocanic acid
  • peptides such as DL-camosin, D-camosin, L-camosin and their derivatives (e.g. anserine), carotenoids, carotenes (e.g.
  • -carotene, ⁇ -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, cystine, cystarmine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, Palmitoyl, oleyl, linoleyl, cholesteryl and glyceryl esters) and their salts, dilaurylthlodipropionate, distearylthio dipropionate, thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) and sulfoximine compounds (e.g.
  • ⁇ -hydroxy fatty acids palmitic acid, phytic acid, lactoferrin
  • ⁇ -Hydroxy acids eg citric acid, lactic acid, malic acid
  • humic acid eg citric acid, lactic acid, malic acid
  • bile acid e.g. g citric acid, lactic acid, malic acid
  • humic acid e.g citric acid, lactic acid, malic acid
  • bile acid e extracts
  • bilirubin biliverdin
  • EDTA EGTA
  • unsaturated fatty acids and their derivatives eg ⁇ -linolenic acid, linoleic acid, oleic acid
  • folic acid e.g.
  • ascorbyl palmitate Mg ascorbyl phosphate, ascorbyl acetate), tocopherols and derivatives (e.g. vitamin E acetate), vitamin A and derivatives (vitamin A palmitate) and coniferyl - benzoate of benzoin, rutinic acid and their 'derivatives, ⁇ -Glycosylrütin, ferulic acid, Furfurylidenglucitol, carnosine, butylhydroxytoluene, butylhydroxyanisole,
  • 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.
  • vitamin E and / or its derivatives turn on the antioxidant (s) d, it is advantageous to choose their respective concentrations from the range from 0.001 to 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 in the sense 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 ⁇ / V / O- Emulsions are present.
  • Such emulsions can preferably also be a microemulsion, a Pickering emulsion or a sprayable emulsion.
  • formulations according to the invention can also advantageously be in the form of oil-free preparations, such as gels, or as anhydrous preparations.
  • 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; benzoates; Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiloxanes and mixed forms thereof.
  • the oil phase of the emulsions, oligogels or hydrodispersions or lipodispersions within the meaning 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 C atoms and saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 3 to 30 C atoms, from the group of esters from aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols Chain length from 3 to 30 carbon atoms.
  • ester oils can then advantageously be selected from.
  • the oil phase can also advantageously be selected from the group of branched and unbranched hydrocarbons and waxes, silicone oils, dialkyl ethers, the group of saturated or unsaturated, branched or unbranched alcohols, and also fatty acid triglycerides, especially the triglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 8 to 24, in particular 12 - 18 carbon atoms.
  • the fatty acid triglycerides can for example 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.
  • Hnhd-01 ' 938 (203-058-I) be waxes, for example cetyl palmitate, to be used as the sole lipid component of the oil phase.
  • the oil phase is advantageously selected from the group 2-ethylhexyl isostearate, octyldodecanol, isotridecyl isononanoate, isoeicosane, 2-ethylhexyl cocoate, C 12-15 alkyl benzoate, caprylic capric acid triglyceride, dicaprylyl ether.
  • Mixtures of d 2 are particularly advantageous.
  • 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 (Oetamethyleyclotetrasiloxane) is advantageously used as the silicone oil to be used according to the invention.
  • 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, of cyclomethicone and 2-ethylhexyl isostearate are also particularly advantageous.
  • the aqueous phase of the preparations according to the invention advantageously advantageously contains - alcohols, diols or polyols of low C number, and also their ethers, preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or - monobutyl ether, diethylene glycol monomethyl or rnonoethyl ether and analogous 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
  • Hnhd-01938 (203-058-1) Silicon dioxide, aluminum silicates, polysaccharides or their derivatives, for example 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, 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, I NCI: octyl salicylate) and esters of cinnamic acid, preferably 4-methoxycinnamic acid (2-ethylhexyl) ester (2-ethylhexyl 4-methoxycinnamate, INCI: octyl methoxycinnamate) and 4-methoxycinnamate acid (l-methoxycinnamate) 4-methoxycinnamate, INCI: isoamyl
  • Preferred inorganic pigments are metal oxides and / or other metal compounds which are sparingly soluble or insoluble in water, in particular oxides of titanium (Ti0 2 ), zinc (ZnO), iron (e.g. Fe 2 0 3 ), zirconium (ZrO 2 ), silicon ( SiO 2 ), manganese (e.g. MnO), aluminum (Al 2 O 3 ), cerium (e.g. Ce 2 0 3 ), mixed oxides of the corresponding metals as well as mixtures of such oxides and the sulfate of barium, (BaS0 4 ).
  • the pigments can also advantageously be used in the form of commercially available oily or aqueous predispersions.
  • 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 In the sense of the present invention, the various surface coatings can also contain water.
  • Inorganic surface coatings in the sense of the present invention can consist of aluminum oxide (Al 2 0 3 ), aluminum hydroxide Al (OH) 3 , or aluminum oxide hydrate (also: alumina, CAS no .: 1333-84-2), sodium hexametaphosphate (NaP0 3 ) 6 , sodium metaphosphate (NaP0 3 ) n , silicon dioxide (SiO 2 ) (also: silica, CAS no. : 7631-86- Hnhd-01938 (203-058-I) 9), or iron oxide (Fe 2 0 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 Siltcagel) or alginic acid.
  • dimethylpolysiloxane also: dimethicone
  • methicone methylpolysiloxane
  • simethicone a mixture of dimethylpolysiloxane with an average chain length of 200 to 350 dimethylsiloxane -Units and Siltcagel
  • alginic acid can consist of vegetable or animal aluminum stearate, vegetable or animal stearic acid, lauric acid, dimethylpolysiloxane (also: dimethicone), methylpoly
  • Zinc oxide particles and predispersions of zinc oxide particles suitable according to the invention 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:
  • 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. 0 70356-09-1), which is sold by Givaudan under the brand name Parsol ® 1789 and 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.
  • Hnhd-01938 especially the 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.
  • Advantageous UV filter substances in the sense of the present invention are also so-called broadband filters, i.e. Filter substances that absorb both UV-A and UV-B radiation.
  • Advantageous broadband filters or UV-B filter substances are, for example, triazine derivatives, such as. B.
  • Hnhd-01938 (203-058-1) is available under the trade name Tinosorb® M from CIBA-Chemicals GmbH.
  • Another invention is 2- (2H-benzotriazol-2-yl) -4-methyl-6- [2-methyl-3- [1, 3,3,3-tetramethyl-1 - [(trimethylsilyl) oxy] di- siloxanyl] propyl] phenol (CAS No .: 155633-54-8) with the INCI name Drometrizole Trisiioxane, 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;
  • benzophenone preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone
  • Advantageous water-soluble filter substances are e.g. B .:
  • Sulfonic acid derivatives of 3-benzylidene camphor such as. B. 4- (2-oxo-3-bornylidene 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 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-
  • dibenzoylmethane derivatives for example the 4- (tert-butyl) -4'-methoxydibenzoylmethane
  • Benzoxazole derivatives such as, in particular, 2,4-bis- [5-1 (dimethylpropyl) benzoxazol-2-yl- (4-phenyl) -imino] -6- (2-ethylhexyl) -imino-1 are also particularly advantageous according to the invention , 3,5-triazine with the CAS No. 288254-16-0, which is available, for example, under the trade name Uvasorb® K2A, and hydroxybenzophenones such as, in particular, the 2- (4'-diethylamino-2'-hydoxybenzoyl) benzoic acid hexyl ester or else Aminobenzophenone, which is available under the Uvinul A Plus.
  • 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
  • 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
  • formulations according to the invention can advantageously, although not necessarily, also be used in combination with UV radiation - be it with artificially generated or natural ultraviolet rays - for example in order to increase natural tanning or to achieve a particularly long-lasting tanning.
  • 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 use of the agent according to the invention in particular a cosmetic and / or dermatological preparation, is preferred - as an aqueous system and / or surfactant preparation for cleaning and care of the skin and / or hair,
  • Hnhd-01938 (203-058-1) - as a multiple emulsion, microemulsion, Pickering emulsion or sprayable emulsion, - as a presun, a sunscreen or an aftersun formulation, - for topical use on skin and / or hair, - for tanning the skin, - for skin care, - for Protection of the skin and / or hair from damaging UV rays,. - to increase melanin synthesis in the skin,.
  • the compounds according to the invention can likewise be a constituent of a polymer matrix, a skin and / or wound dressing, a plaster, a cloth or pad, a spray or on or in textiles, such as bandages or bath textiles.
  • polymer matrices such as, for example, polyurethane matrices
  • Active ingredient release - the compounds from the matrix can be released to the skin or hair and enable their advantageous properties there.
  • the compounds In a plaster application or applied to textiles, bandages or the like, the compounds can penetrate the skin and bring about the desired protection, care or tanning effect.
  • Hnhd-01938 (203-058-1) Water, VES (fully desalinated) ad 100.0 ad 100.0 ad 100.0 The pH is adjusted to 6.

Abstract

L'invention concerne des produits destinés à être appliqués sur la peau ou les cheveux, notamment pour augmenter le bronzage de la peau et la synthèse de la mélanine dans la peau ou les cheveux. L'invention concerne en particulier des préparations cosmétiques ou dermatologiques contenant des cyclohexènes tétrasubstitués. L'utilisation de ces préparations permet d'induire et d'intensifier les mécanismes du bronzage, d'intensifier la couleur des cheveux et par là même de renforcer les défenses propres de la peau et des cheveux.
EP04740896A 2003-09-08 2004-07-10 Produits pour la peau et/ou les cheveux contenant des cyclohexenes tetrasubstitues Withdrawn EP1677752A1 (fr)

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DE10341663A DE10341663A1 (de) 2003-09-08 2003-09-08 Haut- und/oder Haarmittel enthaltend 4-fach substituierte Cyclohexen-Verbindungen
PCT/EP2004/007627 WO2005032506A1 (fr) 2003-09-08 2004-07-10 Produits pour la peau et/ou les cheveux contenant des cyclohexenes tetrasubstitues

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106747002A (zh) * 2016-12-27 2017-05-31 刘曲波 一种防冻保温砂浆
CN106747002B (zh) * 2016-12-27 2018-12-28 南京旭程建筑材料科技有限公司 一种防冻保温砂浆

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