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    • 专利摘要:
    The present invention relates to cosmetic agents characterized by the active content of at least one caffeic acid ester.
    公开号:KR20040021604A
    申请号:KR10-2003-7015134
    申请日:2002-05-11
    公开日:2004-03-10
    发明作者:앙리플로랑스；모제필리쁘；뽈리쥘르
    申请人:코니스 프랑스, 에스.에이.；
    IPC主号:
    专利说明:

    Cosmetic preparations {COSMETIC AGENTS}
    [2] Today, cosmetic preparations face the demanding needs of consumers. Thus, skin creams are no longer sufficient just to provide a good feel, and also contribute to many other needs, for example to control the moisture level of the skin, or to protect the skin against ultraviolet and free radicals, Or it is expected to meet the prevention of environmental stress. For example, there is a particular need for agents that are used when sunburned and have anti-inflammatory effects that neutralize skin damage. According to the current trend, there is particular interest in plant components.
    [3] In this regard, FR-A1 2638967 (Andary) discloses that mono- and dicafeyltartaric acid esters have analgesic inhibitory effects comparable to aspirin. WO 98/11778 (Squires) relates to the use of the treatment of viral or bactericidal inflammation of an extract of Echinacea enriched in caffeic acid esters. According to DE-A1 3744570 (Lomapharm), chicory acid is used to stimulate the immune system. An article in Planta medica 61 (6), 510-514 (1995) , Maffei et al. Describes the effectiveness of echinocosides in protecting collagen against attack of free radicals. Caffeic acid esters are known to inhibit the integrase enzymes required for propagation of the AIDS virus [King et al . J. Med. Chem. 42 (3), 497-509 (1999) ], which has been of special interest today.
    [4] Accordingly, a problem addressed by the present invention is to provide novel cosmetic preparations that combine skin protective activity with anti-inflammatory in particular.
    [1] The present invention relates generally to the field of cosmetics and, more particularly, to formulations containing an effective amount of caffeic acid esters.
    [5] The present invention relates to cosmetic preparations containing an effective amount of at least one caffeic acid ester.
    [6] Surprisingly, it has been found that caffeic acid esters, in particular mono- and dicafet tartaric acid esters, and extracts in which these substances are concentrated meet the above-mentioned needs in an excellent manner.
    [7] Caffeic Acid Ester
    [8] The ester of dihydroxycinnamic acid or caffeic acid may be a condensation product of straight or branched chains with saturated or unsaturated C 6-22 alcohols. However, particular preference is given to esters with hydroxycarboxylic acids, i.e., acyl groups of caffeic acid combined with hydroxyl groups of hydroxycarboxylic acids. Typical examples of suitable hydroxycarboxylic acids other than lactic acid, ricinoleic acid, 12-hydroxystearic acid and maleic acid are especially citric acid, preferably tartaric acid. If the hydroxycarboxylic acid has one or more hydroxyl groups, not only monoesters but also diesters may be used alone or in combination. Thus, particular preference is given to monocafeoyltartaric acid (caftaric acid, formula I), dicafeoyltartaric acid (chicory acid, formula II) and mixtures thereof:
    [9]
    [10]
    [11] According to another embodiment of the invention, the preparation may contain a caffeic acid ester corresponding to formula III:
    [12]
    [13] [Wherein, the substituent R independently of each other represents a hydrogen or a hydroxyl group, and R 1 is a hydroxyl or a residue of a dicarboxylic acid or a dicarboxylic acid monoester]. Preferred esters of formula III are those in which the aromatic rings each have two hydroxyl groups in the ortho or para position and the substituent R is located in a nonaromatic ring system with respect to the hydroxyl. Typical examples are 3,5-dicafeoylquinic acid (3,5-DCQA) in which R 1 represents hydroxyl, and 1 -methoxyoxalyl-3,5-di in which R 1 represents a monomethyl ester residue of oxalic acid. Caffe oil quinic acid (1-MO-3,5-DCQA).
    [14] According to another preferred embodiment of the invention, the preparation may contain free caffeic acid in addition to the caffeic acid ester, wherein the weight ratio of ester to acid is generally in the range of 90:10 to 99: 1. The preparations according to the invention may contain caffeic acid esters in an amount of 0.01 to 5, preferably 0.1 to 2, more preferably 0.5 to 1% by weight.
    [15] Extracts Rich in Caffeic Acid Ester
    [16] Basically, although caffeic acid esters can of course be synthesized, for economic reasons it is preferred to use extracts of plants or bacteria that contain effective amounts of these substances. An ester in which two moles of caffeic acid are linked together by two hydroxyl groups of one mole of tartaric acid is a plant of the genus Echinacea, such as Echinacea purpurea, E. pallida or E. pallida. It is particularly often found in E. augustifolia. The starting materials are in particular chicory and coffee beans, and therefore these extracts are particularly preferred as raw materials. Caffeic acid esters, in particular those corresponding to formula III, can also be produced biotechnically by bacteria, for example of the baccaris genistelloide type or the Achyrocline satureoide type. The material is extracted directly from the aqueous solution.
    [17] extraction
    [18] The extract can be prepared by the originally known method, for example by aqueous, alcoholic or aqueous / alcoholic extraction of plants or parts thereof. Suitable conventional extraction methods, each well known to those skilled in the art and that can be used in principle, such as maceration, remaceration, digestion, agitation, fluid bed extraction, ultrasonic extraction, countercurrent extraction, percolation ), Repercolation, evacolation (extraction under reduced pressure), diacolation, and solid / liquid extraction under continuous reflux performed in a Soxhlet extractor, See, eg, Hagers Handbuch der Pharmazeutischen Praxis (5th edition, Vol. 2, pp. 1026-1030, Springer Verlag, Berlin-Heidelberg-New York 1991) . Exudation is advantageous for industrial use. Although dry plants and / or parts of plants, which are mechanically comminuted and optionally degreasable prior to extraction, are generally used, fresh plants or parts thereof are suitable as starting materials. Any grinding method known to those skilled in the art can be used, for example freeze grinding. Preferred solvents for the extraction process are organic solvents, water (preferably hot water with temperatures above 80 ° C., in particular above 95 ° C.), or mixtures of organic solvents and water, in particular low molecular weight alcohols with rather high content of water. . Particular preference is given to extraction with methanol, ethanol, pentane, hexane, heptane, acetone, propylene glycol, polyethylene glycol, ethyl acetate, and mixtures thereof and water-containing mixtures. The extraction process is usually carried out at 20 to 100 ° C, preferably at 30 to 90 ° C, in particular at 60 to 80 ° C. According to one preferred embodiment, the extraction process is carried out under an inert gas atmosphere to avoid oxidation of the components of the extract. This is particularly important if the extraction is carried out at temperatures above 40 ° C. The extraction time is selected by the person skilled in the art according to the starting material, the extraction method, the extraction temperature, the ratio of the solvent to the raw material and the like. After the extraction process, the crude extract obtained may optionally be subjected to other conventional steps such as, for example, purification, concentration and / or decolorization. If necessary, the extract prepared above can be subjected to selective removal of, for example, individual unwanted components. The extraction process can be performed to any degree, but typically continues until it is exhausted. Typical yields for extracts of (optionally degreased) dry leaves (= dry extracts relative to the amount of raw material used) range from 3 to 15, in particular from 6 to 10% by weight. The present invention includes the discovery that the extraction conditions and the yield of the final extract can be selected according to the desired field of use. Although the solvent can also be completely removed afterwards by drying, in particular spraying or freeze-drying the remaining dark red solid, the extract itself has an active substance content (= solids content) of 0.5 to 10% by weight, per se Can be used. If the purely active substances described above cannot be synthesized by simpler and cheaper methods, the extracts can also be used as starting materials for their preparation. Thus, the content of active substance in the extract may be 5 to 100% by weight, preferably 50 to 95% by weight. The extract itself may be present as a water-containing formulation and / or formulation dissolved in an organic solvent, and as a spray-dried or freeze-dried anhydrous solid. In contrast, suitable organic solvents include, for example, aliphatic alcohols of carbohydrates 1 to 6 (eg ethanol), ketones (eg acetone), halogenated hydrocarbons (eg chloroform or methylene chloride), Lower esters or polyols (eg glycerol or glycol).
    [19] Commercial application
    [20] The invention also relates to the use of caffeic acid esters for the preparation of cosmetic preparations, in particular to skin preparations, wherein said preparation is present in an amount of from 0.01 to 5, preferably from 0.1 to 2, in particular from 0.5 to 1% by weight. Can be. The invention also relates to specific uses of the caffeic acid esters as follows:
    [21] ▷ anti-inflammatory agents;
    [22] Reduction in the release of inflammation-promoting substances from mastocytes or basophilic or eosinophilic leukocytes;
    [23] Active ingredient against acne and rosaceae;
    [24] Cell protection against oxidative stress;
    [25] Cellular protection against UV-A and UV-B rays; And
    [26] Reduced production of reactive oxygen components (ROS) during respiratory rupture.
    [27] As mentioned above, the use according to the invention also extends to extracts of plants or microorganisms having a corresponding high percentage content of caffeic acid esters.
    [28] Cosmetic and / or pharmaceutical preparations
    [29] Caffeic acid esters can be used, for example, in the preparation of cosmetic preparations such as creams, gels, lotions, alcoholic and aqueous / alcoholic solutions, emulsions, wax / fatty compounds, stick preparations, powders or ointments. . The formulations may also be used as additional auxiliaries and additives, including mild surfactants, oil components, emulsifiers, pearlescent waxes, viscosity factors, thickeners, superfatting agents, stabilizers, polymers, silicone compounds, fats, waxes. , Lecithin, phospholipids, biogenic agents, sun protection agents, antioxidants, deodorants, antiperspirants, anti-dandruff agents, film formers, swelling agents, repellents, magnetic tanning agents, tyrosine inhibitors (Pigmentation inhibitor), a hydrophobic-inducing substance, a solubilizer, a preservative, a fragrance oil, a dye and the like.
    [30] Surfactants
    [31] Suitable surfactants are usually anionic, nonionic, cationic and / or which may be present in the formulation in an amount of about 1 to 70% by weight, preferably 5 to 50% by weight, more preferably 10 to 30% by weight. Amphoteric or zwitterionic surfactants. Representative examples of anionic surfactants include soaps, alkyl benzenesulfonates, alkanesulfonates, olefin sulfonates, alkylether sulfonates, glycerol ether sulfonates, α-methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, fatty alcohol ethers. Sulfates, glycerol ether sulfates, fatty acid ether sulfates, hydroxy mixed ether sulfates, monoglyceride (ether) sulfates, fatty acid amide (ether) sulfates, mono- and dialkyl sulfosuccinates, Mono- and dialkyl sulfosuccinamates, sulfoglycerides, amide soaps, ether carboxylic acids and salts thereof, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, N-acylamino acids , For example, acyl lactylate, acyl tartrate, acyl glutamate and acyl acyl Spatates, alkyl oligoglucoside sulfates, protein fatty acid condensates (especially wheat-based vegetable products) and alkyl (ether) phosphates. If the anionic surfactants contain polyglycol ether chains, they may have a conventional homolog distribution, but preferably have a narrow range of homologous distributions. Representative examples of nonionic surfactants include fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers and mixed formals. ), Optionally partially oxidized alkyl (alkenyl) oligoglycosides or glucuronic acid derivatives, fatty acid-N-alkyl glucamides, protein hydrolyzates (particularly wheat based vegetable products), polyol fatty acids Esters, sugar esters, sorbitan esters, polysorbates and amine oxides. If the nonionic surfactants contain polyglycol ether chains, they may have a conventional homogeneous distribution, but preferably have a narrow range of homogeneous distributions. Representative examples of cationic surfactants are quaternary ammonium compounds such as dimethyl distearyl ammonium chloride, and esterquat, especially quaternized fatty acid trialkanolamine ester salts. Representative examples of amphoteric or zwitterionic surfactants are alkylbetaines, alkylamidobetaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines. The above-mentioned surfactants are all known compounds. Information on its structure and manufacturing method can be found in the relevant overview, for example [J. Falbe (ed.), "Surfactants in Consumer Products", Springer Verlag, Berlin, 1987, pp. 54-124 ] or [J. Falbe (ed.), "Katalysatoren, Tenside und Mineraloeladditive (Catalysts, Surfactants and Mineral Oil Additives)", Thieme Verlag, Stuttgart, 1978, pp. 123-217 . Representative examples of particularly suitably mild, ie especially dermatologically suitable, surfactants are fatty alcohol polyglycol ether sulfates, monoglyceride sulfates, mono- and / or dialkyl sulfosuccinates, fatty acid isethionates, fatty acids Sarcosinates, fatty acid taurides, fatty acid glutamate, α-olefin sulfonates, ether carboxylic acids, alkyl oligoglucosides, fatty acid glucamides, alkylamidobetaines, amphoacetals and / or preferably wheat proteins Protein fatty acid condensates.
    [32] Oil ingredients
    [33] Suitable oil components are, for example, Guerbet alcohols based on fatty alcohols having 6 to 18, preferably 8 to 10 carbon atoms, straight C 6-22 fatty acids and straight or branched C 6-22 Esters of fatty alcohols, or esters of branched C 6-13 carboxylic acids with straight or branched C 6-22 fatty alcohols, for example myristyl myristate, myristyl palmitate, myristyl stearate, myristyl iso Stearate, myristyl oleate, myristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetyl behenate, cetyl oleate, stearyl myriate Stearyl palmitate, stearyl stearate, stearyl isostearate, stearyl oleate, stearyl behenate, stearyl Leucate, isostearyl myristate, isostearyl palmitate, isostearyl stearate, isostearyl isostearate, isostearyl oleate, isostearyl behenate, isostearyl oleate, oleyl myristate , Oleyl palmitate, oleyl stearate, oleyl isostearate, oleyl oleate, oleyl behenate, oleyl erucate, behenyl myristate, behenyl palmitate, behenyl stearate, behenyl iso Stearate, behenyl oleate, behenyl behenate, behenyl erucate, erucil myristate, erucil palmitate, erucil stearate, erucil isostearate, erucil oleate, erucil behenate and e Lucille eleucate. See also esters of straight C 6-22 fatty acids with branched chain alcohols, in particular 2-ethyl hexanol, esters of C 18-38 alkylhydroxycarboxylic acids with straight or branched C 6-22 fatty alcohols (see DE 197 56 377). A1 ), in particular based on dioctyl malate, straight and / or branched chain fatty acids and polyhydric alcohols (for example propylene glycol, dimer diols or trimer triols) and / or germane alcohols, C 6-10 fatty acids Triglycerides, liquid mono-, di- and triglyceride mixtures based on C 6-18 fatty acids, esters of C 6-22 fatty alcohols and / or Guerbe alcohols with aromatic carboxylic acids, in particular benzoic acid, C 2-12 dicar Esters of straight or branched chain alcohols having acids with 1 to 22 carbon atoms or polyols containing 2 to 10 carbon atoms and 2 to 6 hydroxyl groups, vegetable oils, branched chain primary alcohols, substituted cyclohexane , Chain and branched C 6-22 fatty alcohol carbonates, such as dicarboxylic ruffle reel carbonate (Cetiol CC), fatty acid based gerbe carbonates having 6 to 18, preferably 8 to 10 carbon atoms, esters of benzoic acid with straight and / or branched chain C 6-22 alcohols (e.g. Finsolv TN), straight or branched, symmetric or asymmetric dialkyl ethers having 6 to 22 carbon atoms per alkyl group, for example dicaprylyl ether (Cetiol OE), ring-opening reaction products of epoxidized fatty acid esters and polyols, silicone oils (cyclomethicone, silicon methicone types, etc.) and / or aliphatic or naphthenic hydrocarbons, for example squalane, squalene or dialkyl cyclohexane This is suitable.
    [34] Emulsifier
    [35] Suitable emulsifiers are, for example, nonionic surfactants from one or more of the following groups:
    [36] 2-30 moles of ethylene for straight chain C 8-22 fatty alcohols, C 12-22 fatty acids, alkyl phenols having 8 to 15 carbon atoms in the alkyl group, and alkylamines having 8 to 22 carbon atoms in the alkyl group Oxides and / or 0-5 moles of propylene oxide addition product;
    [37] Alkyl and / or alkenyl oligoglycosides having 8 to 22 carbon atoms, and ethoxylated analogs thereof;
    [38] Addition products of 1 to 15 moles of ethylene oxide to castor oil and / or hydrogenated castor oil;
    [39] Addition products of 15 to 60 moles of ethylene oxide to castor oil and / or hydrogenated castor oil;
    [40] Partial esters of glycerol and / or sorbitan with unsaturated, straight or saturated, branched fatty acids having from 12 to 22 carbon atoms and / or hydroxycarboxylic acids having from 3 to 18 carbon atoms, and from 1 to 30 Molar ethylene oxide to its addition product;
    [41] Polyglycerol (average autocondensation 2 to 8), polyethylene glycol (molecular weight 400 to 5,000), trimethylolpropane, pentaerythritol, sugar alcohols (eg sorbitol), alkyl glucosides (eg methyl glucoside, Butyl glucoside, lauryl glucoside), and saturated and / or unsaturated, straight or branched chain fatty acids having 12 to 22 carbon atoms with polyglucoside (eg cellulose) and / or having 3 to 18 carbon atoms Partial esters of oxycarboxylic acids, and their addition products to 1 to 30 moles of ethylene oxide;
    [42] Mixed esters of pentaerythritol, fatty acids, citric acid and fatty alcohols according to DE 1165574 PS , and / or mixed esters of fatty acids having 6 to 22 carbon atoms, methyl glucose and polyols, preferably glycerol or polyglycerols,
    [43] Mono-, di- and trialkyl phosphates and mono-, di- and / or tri-PEG-alkyl phosphates and salts thereof;
    [44] Wool wax alcohols;
    [45] Polysiloxane / polyalkyl / polyether copolymers and corresponding derivatives;
    [46] Block copolymers such as polyethylene glycol-30 dipolyhydroxystearate;
    [47] Polymer emulsifiers, for example Pemulen form (TR-1, TR-2) of Goodrich;
    [48] Polyalkylene glycols, and
    [49] Glycerol carbonate.
    [50] Ethylene oxide addition products
    [51] Addition products of ethylene oxide and / or propylene oxide to fatty alcohols, fatty acids, alkylphenols or castor oil are known commercially available products. These are homogeneous mixtures whose average degree of alkoxylation corresponds to the ratio of the amount of ethylene oxide and / or propylene oxide, and the amount of substrate on which the addition reaction is carried out. C 12/18 fatty acid monoesters and diesters of addition products to glycerol of ethylene oxide are known from DE 2024051 PS as refatting agents for cosmetic preparations.
    [52] Alkyl and / or alkenyl oligoglycosides
    [53] Alkyl and / or alkenyl oligoglycosides, their preparation and use are known from the prior art. They are especially prepared by reacting glucose or oligosaccharides with primary alcohols having 8 to 18 carbon atoms. Regarding glycoside units, both monoglycosides in which cyclic sugar units are attached to fatty alcohols by glycoside linkages, and oligomeric glycosides, preferably with an oligomerization degree of about 8 or less, are suitable. The degree of oligomerization is a statistical mean value, based on which the typical homogeneous distribution of the industrial product is based.
    [54] Partial Glyceride
    [55] Representative examples of suitable partial glycerides are hydroxystearic acid monoglycerides, hydroxystearic acid diglycerides, isostearic acid monoglycerides, isostearic acid diglycerides, oleic acid monoglycerides, oleic acid diglycerides, ricinol Resin monoglycerides, ricinoleic acid diglycerides, linoleic acid monoglycerides, linoleic acid diglycerides, linolenic acid monoglycerides, linolenic acid diglycerides, erucic acid monoglycerides, erucic acid diglycerides, Tartar monoglycerides, tartaric acid diglycerides, citric acid monoglycerides, citric acid diglycerides, malic acid monoglycerides, malic acid diglycerides, and industrial mixtures of the above, which may also contain small amounts of triglycerides as a manufacturing process this . Also suitable are addition products of 1 to 30 moles, preferably 5 to 10 moles of ethylene oxide, to the partial glycerides.
    [56] Sorbitan ester
    [57] Suitable sorbitan esters include sorbitan monoisostearate, sorbitan sesquiisostearate, sorbitan diisostearate, sorbitan triisostearate, sorbitan monooleate, sorbitan sesquioleate, Sorbitan Dioleate, Sorbitan Trioleate, Sorbitan Mono-Eleucate, Sorbitan Sesque-Eleucate, Sorbitan Die-Eleucate, Sorbitan Tri-Eleucate, Sorbitan Monolicinoleate, Sorbitan Ses Quiricinoleate, sorbitan diricinoleate, sorbitan triricinoleate, sorbitan monohydroxystearate, sorbitan sesquihydroxystearate, sorbitan dihydroxystearate, sorbitan trihydroxystearate Latex, sorbitan monotartrate, sorbitan sesquitartrate, sorbitan dita Sorbitan sorbitan tritartrate, sorbitan monocitrate, sorbitan sesquicitrate, sorbitan dicitrate, sorbitan tricitrate, sorbitan monomaleate, sorbitan sesquimaleate, sorbitan di Maleate, sorbitan trimaleate and industrial mixtures thereof. Also suitable are addition products of 1 to 30 moles, preferably 5 to 10 moles of ethylene oxide, to the sorbitan esters.
    [58] ▷ polyglycerol ester
    [59] Representative examples of suitable polyglycerol esters include polyglyceryl-2 dipolyhydroxystearate (Dehymuls PGPH), Polyglycerol-3 Diisostearate (Lameform TGI), Polyglyceryl-4 Isostearate (Isolan GI 34), Polyglyceryl-3 Oleate, Diisostearoyl Polyglyceryl-3 Diisostearate (Isolan PDI), Polyglyceryl-3 Methylglucose Distearate (Tego Care 450), Polyglyceryl-3 Beeswax (Cera Bellina) ), Polyglyceryl-4 Caprate (Polyglycerol Caprate T2010 / 90), Polyglyceryl-3 Cetyl Ether (Chimexane NL), Polyglyceryl-3 Distearate (Cremophor GS 32) and polyglyceryl polylysinoleate (Admul WOL 1403), polyglyceryl dimerate isostearate and mixtures thereof. Examples of other suitable polyol esters include trimethylolpropane or pentaerythritol and lauric acid, cocofatty acid, tallow fatty acid, palmitic acid, stearic acid, oleic acid, behenic acid, and the like. Mono-, di- and triesters which selectively react with from 30 moles of ethylene oxide.
    [60] ▷ anionic emulsifier
    [61] Typical anionic emulsifiers are fatty acids containing 12 to 22 carbon atoms, such as palmitic acid, stearic acid or behenic acid, and dicarboxylic acids containing 12 to 22 carbon atoms, such as azelaic acid or sebacic acid.
    [62] Amphoteric and cationic emulsifiers
    [63] Another suitable emulsifier is a zwitterionic surfactant. Zwitterionic surfactants are surfactant compounds containing at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule. Particularly suitable zwitterionic surfactants are the so-called betaines such as N-alkyl-N, N-dimethyl ammonium glycinates having 8 to 18 carbon atoms each in alkyl or acyl groups, for example cocoalkyl dimethyl ammonium glycinate , N-acylaminopropyl-N, N-dimethyl ammonium glycinate such as cocoacylaminopropyldimethyl ammonium glycinate and 2-alkyl-3-carboxymethyl-3-hydroxyethyl imidazoline, and cocoa Real aminoethyl hydroxyethylcarboxymethyl glycinate. Particular preference is given to fatty acid amide derivatives known as CTFA name cocamidopropyl betaine . Ampholytic surfactants are also suitable emulsifiers. Amphoteric surfactants are surfactant compounds which contain not only C 8/18 alkyl or acyl groups, but also at least one free amino group and at least one —COOH— or —SO 3 H— group in the molecule and are capable of internal salt formation. Examples of suitable amphoteric surfactants are N-alkyl glycine, N-alkyl propionic acid, N-alkylaminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N-, each having about 8 to 18 carbon atoms in the alkyl group Alkylamidopropyl glycine, N-alkyl taurine, N-alkyl sarcosine, 2-alkylaminopropionic acid and alkylaminoacetic acid. Particularly preferred amphoteric surfactants are N-cocoalkylaminopropionate, cocoacylaminoethyl aminopropionate and C 12/18 acyl sarcosine. Finally, cationic surfactants are also suitable emulsifiers, particularly those of esterquat type, preferably methyl-4-difatty acid triethanolamine ester salts.
    [64] Fat and wax
    [65] Representative examples of fats are glycerides, ie solid or liquid, vegetable or animal products consisting essentially of mixed glycerol esters of higher fatty acids. Suitable waxes are in particular natural waxes, for example candelilla wax, carnauba wax, Japan wax, espartograss wax, cork wax, guaruma wax, Rice-eye oil wax, sugar cane wax, ouricury wax, montan wax, beeswax, shellac wax, spermaceti, lanolin (wool wax), uropygial fat, ceresin ceresine, ozokerite (earth wax), petrolatum, paraffin wax and microcrystalline wax; Chemically modified waxes (hard waxes), for example montan ester waxes, sasol waxes, hydrogenated jojoba waxes and synthetic waxes such as polyalkylene waxes and polyethylene glycol waxes to be. Other suitable additives besides fats are fat-like substances such as lecithin and phospholipids. Lecithin is known among those skilled in the art as glycerophospholipids formed from fatty acids, glycerol, phosphoric acid and choline by esterification. Thus, lecithin is also frequently referred to by those skilled in the art as phosphatidyl choline (PC). An example of natural lecithin is kephalin, also known as phosphatidic acid and a derivative of 1,2-diacyl-sn-glycerol-3-phosphate. In contrast, phospholipids are generally understood to be mono-, preferably diesters (glycerophosphates) of phosphoric acid and glycerol, usually classified as fat. Sphingosine and sphingolipids are also suitable.
    [66] Pearl luster wax
    [67] Suitable pearlescent waxes are, for example, alkylene glycol esters, specifically ethylene glycol distearate; Fatty acid alkanolamides, specifically coco fatty acid diethanolamides; Partial glycerides, specifically stearic acid monoglycerides; Esters of polybasic, optionally hydroxysubstituted carboxylic acids with fatty alcohols having 6 to 22 carbon atoms, in particular long chain esters of tartaric acid; Fatty compounds such as fatty alcohols having a total of at least 24 carbon atoms, fatty ketones, fatty aldehydes, fatty ethers and fatty carbonates, specifically laurone and distearylethers; Fatty acids such as stearic acid, hydroxystearic acid or behenic acid, olefin epoxides having 12 to 22 carbon atoms and fatty alcohols having 12 to 22 carbon atoms and / or 2 to 15 carbon atoms and 2 to 10 Ring-opening products of polyols having hydroxyl groups, and mixtures thereof.
    [68] Viscosity Factors and Thickeners
    [69] Viscosity factors mainly used are fatty alcohols or hydroxy fatty alcohols having 12 to 22, preferably 16 to 18 carbon atoms, and also partial glycerides, fatty acids or hydroxy fatty acids. Preference is given to using these materials in combination with alkyl oligoglucosides and / or fatty acid N-methyl glucamides and / or polyglycerol poly-12-hydroxystearates of the same chain length. Suitable thickeners are, for example, Aerosil Relative high molecular weight of type (hydrophilic silica), polysaccharides, in particular xanthan gum, guar guar, agar agar, alginate and tylose, carboxymethyl cellulose and hydroxyethyl cellulose, also fatty acids Polyethylene glycol monoesters and diesters, polyacrylates (eg Carbopols And Pemulen type [Goodrich]; Synthalens [Sigma]; Keltrol type [Kelco]; Sepigel type [Seppic]; Salcare type [Allied Colloids]), polyacrylamides, polymers, polyvinyl alcohol and polyvinyl pyrrolidone. Other viscosity factors that have proven particularly effective include bentonite, for example cyclopentasiloxane, disteardimonium hectorite and Bentone, a mixture of propylene carbonate Gel VS-5PC (Rheox). Other suitable viscosity factors include surfactants such as ethoxylated fatty acid glycerides, esters of fatty acids and polyols such as pentaerythritol or trimethylol propane, a narrow range of fatty alcohol ethoxylates or alkyl oligoglucosides, And electrolytes such as sodium chloride and ammonium chloride.
    [70] Superfatting agent
    [71] Hyperlipidemic agents can be selected from materials such as, for example, lanolin and lecithin, and polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides, wherein the fatty acid alkanolamides Also acts as a foam stabilizer.
    [72] Stabilizer
    [73] Stabilizers that can be used are metal salts of fatty acids, for example magnesium, aluminum and / or zinc stearate or ricinoleate.
    [74] polymer
    [75] Suitable cationic polymers are, for example, cationic cellulose derivatives, for example the tradename Polymer JR 400 from Amerchol. Copolymers of quaternized hydroxyethyl cellulose, cationic starch, diallyl ammonium salt and acrylamide, quaternized vinyl pyrrolidone / vinyl imidazole polymers, such as Luviquat (BASF), condensation products of polyglycols and amines, quaternized collagen polypeptides, for example Lauryldimonium Hydroxypropyl Hydrolyzed Collagen (Lamequat L, Gruenau), quaternized wheat polypeptide, polyethyleneimine, cationic silicone polymers such as copolymers of amodimethicone, adipic acid and dimethylaminohydroxypropyl diethylenetriamine (Cartaretins , Sandoz), a copolymer of acrylic acid and dimethyl diallyl ammonium chloride (Merquat 550, Chemviron), for example, polyaminopolyamides as described in FR 2252840 A and their crosslinked water soluble polymers, cationic chitin derivatives, for example quaternized, optionally in a microcrystalline dispersion Chitosan, dihaloalkyl, for example a condensation product of dibromobutane and bis-dialkylamine, for example bis-dimethylamino-1,3-propane, cationic guar gum, for example Jaguar of Celanese CBS, Jaguar C-17, Jaguar C-16, quaternized ammonium salt polymer, for example Mirapol of Miranol A-15, Mirapol AD-1, Mirapol AZ-1.
    [76] Suitable anionic, zwitterionic, amphoteric and nonionic polymers are, for example, vinyl acetate / crotonic acid copolymers, vinyl pyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobornyl acrylic Copolymers, methyl vinyl ether / maleic anhydride copolymers and esters thereof, uncrosslinked polyacrylic acid, and polyacrylic acids crosslinked with polyols, acrylamidopropyl trimethylammonium chloride / acrylate copolymers, octylacrylamide / methyl met Acrylate / tert-butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymer, polyvinyl pyrrolidone, vinyl pyrrolidone / vinyl acetate copolymer, vinyl pyrrolidone / dimethylaminoethyl methacrylate / Vinyl caprolactam terpolymers, and optionally derivatized cellulose ethers and The Recon. Other suitable polymers and thickeners are described in Cosm. Toil. 108 , 95 (1993) .
    [77] Silicone compound
    [78] Suitable silicone compounds are, for example, dimethyl polysiloxane, methylphenyl polysiloxane, cyclic silicone and amino-, fatty acid-, alcohol-, polyether-, epoxy-, fluorine-, glycoside- which are possible both in liquid and resin form at room temperature. And / or alkyl-modified silicone compounds. Other suitable silicone compounds are simethicone which is a mixture of dimethicones and hydrogenated silicates of average chain length of 200 to 300 dimethylsiloxane units. For a detailed overview of suitable volatile silicones see Todd et al . , Cosm. Toil. 91 , 27 (1976) .
    [79] UV protection factor and antioxidant
    [80] The ultraviolet protection factor according to the invention is, for example, an organic substance which is liquid or crystalline at room temperature and is capable of absorbing ultraviolet light and which can emit absorbed energy in the form of longer wavelength radiation, for example heat. Filter). UV-B filters may be oil soluble or water soluble. The following are examples of oil soluble materials:
    [81] 3-benzylidene camphor or 3-benzylidene norcampa and derivatives thereof, for example 3- (4-methylbenzylidene) -campa as described in EP 0693471 B1 ;
    [82] 4-aminobenzoic acid derivatives, preferably 4- (dimethylamino) -benzoic acid-2-ethylhexyl ester, 4- (dimethylamino) -benzoic acid-2-octyl ester and 4- (dimethylamino) -benzoic acid amyl ester;
    [83] Esters of cinnamic acid, preferably 4-methoxycinnamic acid-2-ethylhexyl ester, 4-methoxycinnamic acid propyl ester, 4-methoxycinnamic acid isoamyl ester, 2-cyano-3,3-phenylcinnamic acid 2-ethylhexyl ester (octocrylene);
    [84] Esters of salicylic acid, preferably salicylic acid-2-ethylhexyl ester, salicylic acid-4-isopropylbenzyl ester, salicylic acid homomentyl ester;
    [85] Derivatives of benzophenones, preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-meth Oxybenzophenone;
    [86] Esters of benzalmalonic acid, preferably 4-methoxybenzalmalonic acid di-2-ethylhexyl ester;
    [87] Triazine derivatives, for example in 2,4,6- trianilino- (p-carbo-2'-ethyl-1'-hexyloxy) -1,3,5-triazine and EP 0818450 A1 Octyl triazone described, or dioctyl butamido triazone (Uvasorb HEB);
    [88] Propane-1,3-dione, for example 1- (4-tert-butylphenyl) -3- (4'-methoxyphenyl) -propane-1,3-dione;
    [89] Ketotricyclo (5.2.1.0) decane derivatives described in EP 0694521 B1 .
    [90] Suitable water soluble materials are as follows:
    [91] 2-phenylbenzimidazole-5-sulfonic acid, and alkali metal, alkaline earth metal, ammonium, alkylammonium, alkanolammonium and glucammonium salts thereof.
    [92] Sulfonic acid derivatives of benzophenone, preferably 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and salts thereof;
    [93] Sulfonic acid derivatives of 3-benzylidene camphors such as 4- (2-oxo-3-bornylidenemethyl) -benzene sulfonic acid and 2-methyl-5- (2-oxo-3-bornylidene) -sulfonic acid And salts thereof.
    [94] Typical UV-A filters are in particular derivatives of benzoyl methane, for example 1- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) -propane-1,3-dione, 4- tert-butyl-4'-metoxysidbenzoyl methane (Parsol 1789), 1-phenyl-3- (4'-isopropylphenyl) -propane-1,3-dione, and the enamine compound described in DE19712033 A1 (BASF). In addition, UV-A and UV-B filters can of course also be used in the form of mixtures. Particularly preferred bonds are benzoyl methane in combination with cinnamic acid esters, preferably 4-methoxycinnamic acid-2-ethyl hexyl ester and / or 4-methoxycinnamic acid propyl ester and / or 4-methoxycinnamic acid isoamyl ester, eg 4-tert-butyl-4'-methoxydibenzoylmethane (Parsol 1789) and derivatives of 2-cyano-3,3-phenylcinnamic acid-2-ethylhexyl ester (octocrylene). Such combinations advantageously combine with a water soluble filter, for example 2-phenylbenzimidazole-5-sulfonic acid, and alkali metal, alkaline earth metal, ammonium, alkylammonium, alkanolammonium and glu ammonium salts thereof.
    [95] In addition to the above soluble materials, insoluble photoprotective pigments, ie finely dispersed metal oxides or salts, can also be used for the purposes of the present invention. Examples of suitable metal oxides are, in particular, zinc oxide and titanium dioxide, and oxides of iron, zirconium oxide, silicon, manganese, aluminum and cerium, and mixtures thereof. Silicates (talc), barium sulphate and zinc stearate can be used as salts. Oxides and salts are used in the form of pigments for skin protection and skin protection emulsions, and decorative cosmetics. The particles should have an average diameter of less than 100 nm, preferably 5 to 50 nm, in particular 15 to 30 nm. They may be spherical in shape, but elliptical particles or other non-spherical particles may also be used. In addition, the pigments can be surface-treated, ie hydrophilized or hydrophobized. Typical examples are coated titanium dioxides such as Titandioxid T 805 (Degussa) and Eusolex There is T2000 (Merck). Suitable hydrophobic coatings are in particular silicones, especially of trialkoxyoctylsilanes or simethicones. So-called micro- or nanopigments are preferably used as sunscreens. Micronized zinc oxide is preferably used. Other suitable UV protection filters are described in P. Finkel's overview [ SOFW-Journal 122 , 543 (1996) ] and in Parf. Kosm. 3 , 11 (1999) .
    [96] In addition to the two groups of primary sunscreen factors described above, secondary sunscreen factors of the antioxidant type may also be used. Secondary sunscreen factors of the antioxidant type interfere with the photochemical reaction chains that are triggered when ultraviolet light penetrates the skin. Representative examples thereof include amino acids (eg glycine, histidine, tyrosine, tryptophan) and derivatives thereof, imidazoles (eg urocanic acid) and derivatives thereof, peptides such as D, L-carnosine , D-carnosine, L-carnosine and derivatives thereof (e.g., anserine), carotenoids, carotene (e.g., α-carotene, β-carotene, lycopene) and derivatives thereof, Chlorogenic acid and its derivatives, lipoic acid and its derivatives (e.g. dihydrolipoic acid), aurothioglucose, propylthiouracil and other thiols (e.g. thioredoxin ( thioredoxine, glutathione, cysteine, cystine, cystamine and glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, γ-linoleyl, cholesteryl and Glyceryl esters thereof and Salts of these, dilaurylthiodipropionate, distearylthiodipropionate, thiodipropionic acid and derivatives thereof (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) and very low compatible doses ( For example, pmol to μmol / kg) of sulfoximine compounds (e.g. butionine sulfoximine, homocysteine sulfoximine, butionine sulfone, penta-, hexa- and hepta-thione sulfoximine) , (Metal) chelators (e.g. α-hydroxyfatty acid, palmitic acid, phytic acid, lactoferrine), α-hydroxy acids (e.g. citric acid, lactic acid, malic acid) ), Humic acid, bile acid, bile extract, bilirubin, biliverdin, EDTA, EGTA and its derivatives, unsaturated fatty acids and derivatives thereof (e.g., γ-linolenic acid, linoleic acid, oleic acid) , Folic acid and derivatives thereof, ubiquinone (u biquinone) and ubiquinol and derivatives thereof, vitamin C and derivatives thereof (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, rutinic acid and derivatives thereof of benzoin resin, α-glycosyl rutin, ferulic acid, furfu Liliden Gluscitol, Carnosine, Butyl Hydroxytoluene, Butyl Hydroxyanisole, nordihydroguaiac Resin Acid, nordihydroguaiaretic acid, Trihydr a hydroxy butyric benzophenone, uric acid and derivatives thereof, mannose (mannose) and derivatives thereof, superoxide-dismutase (Superoxid-dismutase), zinc and derivatives thereof (e.g., ZnO, ZnSO 4), selenium and Derivatives (e.g. selenium methionine), stilbenes and derivatives thereof (e.g. stilbene oxide, trans-stilbene oxide) and derivatives of these active substances suitable for the purposes of the present invention (salts, esters) , Ethers, sugars, nucleotides, nucleosides, peptides and lipids).
    [97] Biogenic agents
    [98] In the context of the present invention, biological agents include, for example, tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, (deoxy) ribohexane and cleavage products thereof, β-glucan, retinol, bisabolol , Allantoin, phytantriol, panthenol, AHA acid, amino acids, ceramides, pseudoceramides, essential oils, plant extracts such as plum extract, bambara nuts Extracts, and vitamin complexes.
    [99] Deodorant and Antimicrobial Agent
    [100] Cosmetic deodorants counter, mask or eliminate body odors. Body odor is formed as a result of the action of skin bacteria on apocrine sweating which results in the formation of decomposition products with an unpleasant odor. Thus, deodorants contain active ingredients that act as antimicrobial agents, enzyme inhibitors, malodor absorbers or malodor masking agents.
    [101] ▷ antimicrobial agents
    [102] Basically, suitable antimicrobial agents are all substances which act against gram-positive bacteria, for example 4-hydroxybenzoic acid and its salts and esters, N- (4-chlorophenyl) -N '-( 3,4-dichlorophenyl) -urea, 2,4,4'-trichloro-2'-hydroxydiphenylether (triclosan), 4-chloro-3,5-dimethylphenol, 2,2 ' -Methylene-bis- (6-bromo-4-chlorophenol), 3-methyl-4- (1-methylethyl) -phenol, 2-benzyl-4-chlorophenol, 3- (4-chlorophenoxy) -Propane-1,2-diol, 3-iodo-2-propynyl butyl carbamate, chlorohexidine, 3,4,4'-trichlorocarbanilide (TTC), antibacterial perfume, thymol ( thymol), thyme oil, eugenol, clove oil, menthol, mint oil, farnesol, phenoxyethanol, glycerol monocaprate, glycerol monocaprylate, glycerol monolau Latex (GML), diglycerol monocaprate ( DMC), salicylic acid-N-alkylamides, for example salicylic acid-n-octyl amide or salicylic acid-n-decyl amide.
    [103] ▷ enzyme inhibitor
    [104] Suitable enzyme inhibitors are, for example, esterase inhibitors. Esterase inhibitors are preferably trialkyl citrates such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate and especially triethyl citrate (Hydagen CAT). Esterase inhibitors reduce odor formation by inhibiting enzyme activity. Other esterase inhibitors include sterol sulfates or phosphates such as lanosterol, cholesterol, campesterol, stigmasterol and cytosterol sulfates or phosphates, dicarboxylic acids and esters thereof, for example For example, glutaric acid, glutaric acid monoethyl ester, glutaric acid diethyl ester, adipic acid, adipic acid monoethyl ester, adipic acid diethyl ester, malonic acid and malonic acid diethyl ester, hydroxycarboxylic Acids and esters thereof, such as citric acid, malic acid, tartaric acid or tartaric acid diethyl ester, and zinc glycinate.
    [105] Odor absorbent
    [106] Suitable malodor absorbers are substances which can absorb and retain large amounts of malodor-forming compounds. They reduce the partial pressure of the individual components and also reduce the rate at which they diffuse. In this regard, it is important that the fragrance should remain intact. Odor absorbers are not effective against bacteria. These are, for example, zinc complexes of ricinoleic acid, or certain flavors mainly of odor neutrality known as "fixateurs" to those skilled in the art, for example, ladanum or styrox ( styrax) or certain abietic acid derivatives. Odor masking agents, besides their odor-shielding function, are perfumes or perfumes that impart their special flavor characteristics to deodorants. Suitable perfume oils are, for example, mixtures of natural and synthetic perfumes. Natural flavors include extracts of flowers, stems and leaves, fruits, fruit peels, roots, woody parts, herbs and grasses, needles and branches, rosin and balsams. Animal raw materials, such as musk and dissociation, may also be used. Representative synthetic perfume compounds are products of the ester, ether, aldehyde, ketone, alcohol and hydrocarbon type. Examples of fragrance compounds of the ester type include benzyl acetate, p-tert-butyl cyclohexyl acetate, linalyl acetate, phenyl ethyl acetate, linalyl benzoate, benzyl formate, allyl cyclohexyl propionate, styralyl (styrallyl) propionate and benzyl salicylate. Ethers include, for example, benzyl ethyl ether, and aldehydes include, for example, straight alkanal, citral, citronellal, citro, having from 8 to 18 carbon atoms. Citronellyloxyacetaldehyde, cyclamen aldehyde, hydroxycitronellal, lilial and bourgeonal. Examples of suitable ketones are, for example, ionone and methyl cedryl ketone. Suitable alcohols are anethol, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol. Hydrocarbons mainly include terpene and balsam. However, preference is given to using mixtures of different perfume compounds which together produce a pleasant fragrance characteristic. Another suitable perfume oil is a relatively low volatility essential oil which is mainly used as an aromatic component. Examples include sage oil, chamomile oil, cloves oil, melissa balm oil, mint oil, cinnamon leaf oil, lime-flower oil, juniper berry oil, vetiver oil, olibanum ) Oil, galbanum oil, ladanum oil and lavendin oil. Preference is given to using the following individually or in the form of mixtures: bergamot oil, dihydromyrcenol, lily, lyral, citronellol, phenylethyl alcohol, α-hexylcinnamaldehyde, Geraniol, benzyl acetone, cyclamen aldehyde, linalool, Boisambrene Forte, Ambroxan, indole, hedione, sandelice, citrus oil, mandarin oil , Orange oil, allylamyl glycolate, cyclovertal, labendine oil, clary oil, β-damascone, geranium oil bourbon, cyclohexyl salicylate, Bertofix Coeur, Iso-E-Super, Fixolide NP, evernyl, iraldein gamma, phenylacetic acid, geranyl acetate, benzyl acetate, rose ) Oxide, romillat, tooth Rotiyl and floramat.
    [107] ▷ Antiperspirant
    [108] Antiperspirants reduce sweating and, therefore, act against wetness of the armpits or odors in the body by affecting the activity of eccrine sweat glands. An aqueous or water-free antiperspirant formulation typically contains the following ingredients:
    [109] Astringent active ingredients,
    [110] Oil component,
    [111] ▷ nonionic emulsifier,
    [112] ▷ secondary emulsifiers,
    [113] ▷ viscosity factor
    [114] Auxiliaries, for example in the form of thickeners or complexing agents, and / or
    [115] Non-aqueous solvents such as ethanol, propylene glycol and / or glycerol.
    [116] Suitable astringent active ingredients of antiperspirants are especially salts of aluminum, zirconium or zinc. Suitable antihydrotic agents of this type are, for example, aluminum chloride, aluminum chlorohydrate, aluminum dichlorohydrate, aluminum sesquichlorohydrate, and their for example 1,2-propylene glycol and Complexes, aluminum hydroxyalantoinates, aluminum chloride tartrates, aluminum zirconium trichlorohydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium pentachlorohydrate, and their complexes with amino acids such as, for example, glycine . The fat soluble and water soluble auxiliaries typically used in antiperspirants may be present in relatively small amounts. Such fat-soluble aids include, for example:
    [117] ▷ anti-inflammatory, skin protective or aromatic essential oils,
    [118] ▷ synthetic skin protectants and / or
    [119] Oil-soluble balm.
    [120] Typical water soluble additives include, for example, preservatives, water soluble fragrances, pH adjusters such as buffer mixtures, water soluble thickeners such as water soluble natural or synthetic polymers such as xanthan gum, hydroxyethyl cellulose, Polyvinyl pyrrolidone or high molecular weight polyethylene oxide.
    [121] Film former
    [122] Conventional film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinyl pyrrolidone, vinyl pyrrolidone / vinyl acetate copolymers, acrylic acid polymers, quaternized cellulose derivatives, collagen , Hyaluronic acid and its salts and similar compounds.
    [123] Swelling agent
    [124] Suitable aqueous commercial swelling agents are montmorillonite, clay minerals, Pemulen and alkyl-modified Carbopol types (Goodrich). Other suitable polymers and swelling agents are described in R. Lochhead's review, Cosm. Toil. 108 , 95 (1993) .
    [125] Insect repellent
    [126] Suitable insect repellents are N, N-diethyl-m-toluamide, pentane-1,2-diol or ethyl butylacetylaminopropionate.
    [127] Magnetic tanning agent and pigmentation inhibitor
    [128] Suitable magnetic tanning agents are dihydroxyacetones. Suitable tyrosine inhibitors that inhibit melanin formation and are used as pigmentation inhibitors include, for example, arbutin, ferulic acid, kojic acid, coumaric acid and ascorbic acid (vitamin C). )
    [129] Hydrogenic Causing Agents (Hydrotrope)
    [130] In addition, in order to improve flow behavior, a combustible triggering material such as ethanol, isopropyl alcohol or polyol may be used. Suitable polyols preferably have from 2 to 15 carbon atoms and at least 2 hydroxyl groups. The polyols may have other functional groups, in particular amino groups, or may be modified with nitrogen. Representative examples are as follows:
    [131] Glycerol;
    [132] Alkylene glycols having an average molecular weight of 100 to 1000 Daltons such as ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and polyethylene glycol;
    [133] Degree of self-condensation 1.5 to 10 industrial oligoglycerol mixtures, for example industrial diglycerol mixtures with a diglycerol content of 40 to 50% by weight;
    [134] Methylol compounds such as trimethylol ethane, trimethylol propane, trimethylol butane, pentaerythritol and dipentaerythritol;
    [135] Lower alkyl glucosides, especially those having from 1 to 8 carbon atoms in the alkyl group, for example methyl and butyl glucoside;
    [136] Sugar alcohols having 5 to 12 carbon atoms, for example sorbitol or mannitol,
    [137] Sugars having 5 to 12 carbon atoms, for example glucose or sucrose;
    [138] Amino sugars such as glucamine;
    [139] Dialcoholamines such as diethanolamine or 2-aminopropane-1,3-diol.
    [140] Preservative
    [141] Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid, and the tradename Surfacine Known are silver complexes and other classes of compounds listed in Appendix 6, Parts A and B of Kosmetikverordnung ("Cosmetics Directive").
    [142] Balm and aroma
    [143] Suitable perfume oils are mixtures of natural and synthetic perfumes. Natural flavors include flowers (lilies, lavender, roses, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petite grains), fruits (anise ( anise) berries, coriander, cumin, juniper), fruit peel (bergamot, lemon, orange), roots (nutmeg, angelica, celery, cardamom, costus, iris, calmus), wood grain (pine) , Sandalwood, guaiac wood, cedarwood, rosewood, herbs and grasses (tarragon, lemongrass, sage, thyme), needles and branches (spruce) , Fir, pine, pine), rosin and balsam (galbanum, elemi, benzoin, myrrh, olibanum, opoponax) extracts. Animal raw materials such as musk and dissociation may also be used. Representative synthetic perfume compounds are products of the ester, ether, aldehyde, ketone, alcohol and hydrocarbon type. Examples of fragrance compounds of the ester type are benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, dimethyl benzyl carvinyl acetate, phenylethyl acetate, linalyl benzoate, benzyl formate, ethyl Methyl phenyl glycinate, allyl cyclohexyl propionate, styralyl propionate and benzyl salicylate. Ethers include, for example, benzyl ethyl ether, and aldehydes include, for example, straight alkanals having 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamen aldehyde, Hydroxycitronellal, lily and burgional. Examples of suitable ketones are ionone, α-isomethylionone and methyl cedryl ketone. Suitable alcohols include anethol, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol. Hydrocarbons mainly include terpenes and balsams. However, preference is given to using mixtures of different perfume compounds which together produce a pleasant fragrance characteristic. Another suitable perfume oil is a relatively low volatility essential oil mainly used as an aromatic component. Examples include sage oil, chamomile oil, cloves oil, melissa oil, mint oil, cinnamon leaf oil, linden-flower oil, juniper berry oil, vetiver oil, olibanum oil, galbanum oil, radanum oil and rabendine oil. have. Preference is given to using the following individually or in the form of mixtures: bergamot oil, dihydromirsenol, lily, lyral, citronellol, phenylethyl alcohol, α-hexylcinnamaldehyde, geraniol, benzyl acetone , Cyclamen Aldehyde, Linalool, Brosambarene Forte, Ambroxane, Indole, Hedion, Sandelis, Citrus Oil, Mandarin Oil, Orange Oil, Allylamyl Glycolate, Cyclovertal, Labendine Oil, Clary Oil , β-Damascon, Geranium Oil Bourbon, Cyclohexyl Salicylate, Bertopix Coyur, Iso-E-Super, Picsolidide NP, Everyl, Iraldine Gamma, Phenylacetic Acid, Geranyl Acetate, Benzyl Acetate, Rose Oxide , Lomillat, erotyl and floramat.
    [144] Suitable aromas include, for example, peppermint oil, spearmint oil, anidese oil, japanese anise oil, caraway oil, eucalyptus oil, fennel oil, citrus oil, wintergreen oil, cloves oil, menthol and the like.
    [145] dyes
    [146] Suitable dyes are described, for example, in Farbstoffkommission der Deutschen Forschungsgemeinschaft, Verlag Chemie, Weinheim, 1984, pp. 81-106 ] any suitable material approved for cosmetic use, such as listed in the publication "Kosmetische Faerbemittel" . Examples are Cochinyl Red A (CI 16255), Pattern Blue V (CI 42051), Indigotin (CI 73015), Chlorophyllin (CI 75810), Quinoline Yellow (CI 47005), Titanium Dioxide (CI 77891), Indanthrene Blue RS (CI 69800) and Mother Lake (CI 58000). Luminol may also be present as a luminescent dye. These dyes are generally used at concentrations of from 0.001 to 0.1% by weight, based on the total mixture.
    [147] The total percentage content of auxiliaries and additives may be 1 to 50% by weight, preferably 5 to 40% by weight, based on the specific formulation. The formulations may be prepared by standard high or low temperature processes and are preferably prepared by a phase inversion temperature method.
    [148] Preparation Example 1. 0.05 kg of chopped chicory root was introduced into a glass beaker containing 500 ml of 70% by volume aqueous methanol. The mixture was stirred at 45 ° C. for 1 hour and the solid components were filtered off. The extract was then removed from methanol, freeze dried and 18.6 g of residue was obtained. 10 g of the crude extract was dissolved in 10 mL of water and introduced into a 4 × 40 cm Amberlite XAD 1180 column, eluted sequentially with 750 mL of water, 750 mL of methanol (40% by volume) and 3750 mL of methanol (60% by volume). I was. In addition to chicory acid, the eluate contains, in particular, chlorogenic acid, free caffeic acid and various caffeoyl conjugenes.
    [149] Preparation Example 2 16 kg of powdered chicory root was introduced into a glass beaker containing 78 ml of 96% by volume ethanol. The mixture was stirred at 45 ° C. for 6 hours and the solid components were filtered off. Ethanol was then evaporated from the filtrate solution to give a dry extract at 23% by weight concentration (23 g of dry extract for 100 mL of liquid).
    [150] The crude extract was introduced into a 50 mm × 250 mm Lichrosher RP18 10 μm HPLC column and eluted with a mobile solvent of 76% water, 4% acetic acid 20% acetic acid. Peaks after 900 to 1000 seconds were collected. The mobile solvent was removed by evaporation and freeze-dried to give the desired fraction.
    [151] A. Cell Protection Against UV-B Rays
    [152] The purpose of this test is to show that the extract is anti-inflammatory to human keratinocytes. UV-B was chosen as a stress factor because UV-B causes skin inflammation (erythema, edema) by activating an enzyme that releases arachidonic acid, such as, for example, phospholipase A2 (PLA2). This not only damages the membrane tissue, but also forms inflammatory substances such as, for example, PGE2 type prostaglandins. The effect of UV-B rays on keratinocytes was measured in vitro through the release of cytoplasmic enzymes, such as LDH (lactate dehydrogenase), that involve cell damage and the formation of PGE2. To carry out the test, fibroblast cultures were mixed with fetal calf serum and inoculated with test substance two days later. After 36 hours of incubation at 37 ° C. and 5 vol% CO 2 level, the nutrient medium was replaced with electrolyte solution and fibroblasts were damaged by UV-B specific amount (50 mJ / cm 2 ). The amount of keratinocytes was measured by a cell counter after trypsinization, and LDH concentrations were measured by enzymes. The results are shown in Table 1, where activity is expressed as% relative to baseline, which is the mean value of two test series involving two measurements.
    [153] Anti-inflammatory activity (relative)extract Concentration (% w / v) Cell DNA LDH released Base group without UV-B irradiation01000 Base group with UV-B irradiation029100 UV-B Probe + Chicory Extract0.00033389 UV-B Probe + Chicory Extract0.00013678 UV-B Probe + Ascorbic Acid0.014850
    [154] B. Stimulation Inhibitory Activity
    [155] 4 μl of a 1.5 wt% aqueous solution of the extract of Preparation Example was added to a commercial skin cream. Subsequently, 1 cm 2 area inside both forearms of 10 volunteer panels was treated with 3 μl of a 70% by weight glycolic acid solution. The test cream was then applied to the right forearm and the placebo cream to the left forearm, with volunteers not knowing which cream contained the ingredient being tested. The extent of stimulation for a 10 minute contact time was assessed with a magnitude of 0 (none) to 3 (slightly). The result (average value) was shown in Table 2. Mean of stimulus size was 2.75 for placebo and 0.2 for test substance.
    [156] Sensory evaluationContact time (min) Stimulus size PlaceboTest productDeviation One303 2303 3303 430.52.5 53One2 620.51.5 72.502.5 82.502.5 92.502.5 10303
    [157] C. Anti-inflammatory Activity
    [158] In the process of skin inflammation, leukocytes such as, for example, polymorphonuclear neutrophil granulocytes (PMN) are stimulated by peptides such as, for example, cytokines, for example with leukotriene released from activated or necrotic cells of the dermis. Emits the same messenger material. The activated PMN releases not only pro-inflammatory cytokines, leukotrienes and proteolytic enzymes, but also ROS such as superoxides and hypochlorite anions that act to destroy invading pathogens or fungi, for example. This activity of PMN during inflammation is known as respiratory rupture and can cause additional damage in tissue. To investigate to what extent the test extract can prevent or reduce respiratory rupture, the cell lines of human leukemia granulocytes of PMN were incubated with the test substance at 37 ° C. and 5% by volume CO 2 . After the yeast extract (Zymoic acid) was added to the cell solution to initiate respiratory rupture, the release of superoxide anions was measured through the reaction with luminol. The results are shown in Table 3, where the number of cells and the amount of ROS released are expressed as% relative to baseline, which is the average of a series of measurements including three measurements.
    [159] Anti-inflammatory activity (relative)Test product Concentration (% w / v) Cell count Released ROS Control 100100 Chicory Extract0.00199 ± 926 ± 11 Chicory Extract0.01102 ± 48 ± 2 Chicory Extract0.181 ± 42 ± 1 Monocycline0.001102 ± 230 ± 7
    [160] The above examples show that chicory extract has a strong inhibitory effect on respiratory rupture of human granulocytes, without damaging human granulocytes.
    [161] D. Free Radical Suppression Test
    [162] Free radicals are reactive materials characterized by nonconjugated free electrons. They are derived from, for example, unsaturated fatty acids, certain amino acids, and oxygen, which spontaneously forms during biological processes or during natural inflammatory processes, such as in the respiratory chain, especially in mitochondria. Oxidative stress, such as ultraviolet irradiation or environmental toxins, includes the formation of free radicals that cause damage to cellular and tissue components (lipids, proteins, sugars, and nucleic acids). In fact, the toxicity of free radicals is critically influenced by oxygen content and plays an important role in the aging process and serious diseases such as cancer and diabetes.
    [163] Activity against free radicals was determined by biochemical tests using reactive oxygen species (ROS), the so-called superoxide anions (O 2 °). Superoxide anions are derived from xanthine oxidase and lipoxygenase activity. Xanthine oxidase (XOD) is an enzyme that is activated during oxidative stress and promotes the release of O2 ° during the decomposition of hypoxanthine (HX), which is produced in excess when it interferes with metabolism of energy cells. O 2 ° was then reacted spontaneously or with superoxide dismutase (SOD) to form hydrogen peroxide (H 2 O 2 ), a source of HO radicals that allowed the reaction to continue during the Fenton reaction. O 2 ° released during the inflammatory process is formed from arachidonic acid by lipoxygenase activity of leukocytes during leukotriene synthesis ( MacCord, M., Chabot Fletcher, M., Breton, J., Marshall, LA; Journal of Investigative Dermatology, 1994, Vol. 102, pp. 980-986; Bouclier, M., Hensby CN; Annales de Dermatologie & de Venereologie, 1986, Vol. 113, pp. 1289-1293 ).
    [164] Test using superoxide anion O2 ° produced by xanthine oxidase (Table 4a)
    [165] Enzyme-based hypoxanthine / xanthine oxidase forms O2 ° which reacts with the tetrazolium salt and forms colored compounds where optical density can be measured at 540 nm. Active materials against free radicals reduce the optical density.
    [166] Test using superoxide anion produced by lipoxygenase (Table 4b)
    [167] Enzyme-based arachidonic acid / lipoxygenase forms O 2 ° which can be measured by luminescence with luminol during the synthesis of leukotriene. The greater the activity against free radicals, the more luminescent is suppressed.
    [168] result:
    [169] Test with superoxide anion O2 ° produced by xanthine oxidase Concentration (% w / v)Inhibition Rate (%)EC 50 (% w / v) Extract of Preparation Example 20.1950.0154 0.03770.0140
    [170] Test using superoxide anion O2 ° produced by lipoxygenase extractConcentration (% w / v)Suppression (%)EC 50 (% w / v) Extract of Preparation Example 10.0003160.0007 0.00175 0.00370 0.0191 Extract of Preparation Example 20.003350.00169 0.00369 0.0195 Caffeic Acid (Sigma)0.00002160.00018 0.000254
    [171] D. Anti Aging Activity-Determination of G6PDH Activity
    [172] This test was used to measure the stimulation of the G6PDH enzyme (glucose 6 phosphate dehydrogenase) which interferes with the aging process of human skin. G6PDH promotes the first stage of the "orthosaccharide pathway" (also known as the hexose monophosphate pathway or the HMP pathway). The first step, ie conversion of glucose-6-phosphate (G6P) to 6-phosphogluconate (6GP) by G6PDH, requires coenzyme NADP, which in turn is converted to NADPH2. This reduced form of coenzyme promotes many enzymatic reactions, and also glutathione recycling and lipid synthesis.
    [173] During the "orthosaccharide route", an essential component of DANN, namely deoxyribose, is produced. Reduced glutathione can protect skin enzymes containing SH groups or enhance the cell's resistance to oxidative stress. Thus, G6PDH is an important enzyme for the synthesis of important components for protecting skin against skin regeneration and oxidative stress.
    [174] Measurement of G6PDH (glucose 6 phosphate dehydrogenase) activity is described by Garidelli de Quincenet in Annual Dermatol. Venereol. 107 (12) , 1163-1170 (1980) ]. Using in vitro culture of fibroblasts of human dermis, Desaulniers in Toxic. In vitro 12 (4) , 409-422 (1998) ], the DNA content was measured. Incubation time of fibroblasts was 3 days. The results are shown in Table 5, where the average of eight trials including three measurements.
    [175] G6PDH Activity-Measurement on Fibroblasts of Human DermisLevel of G6PDH after 6 days (% Of control) density medium Analysis number SEM Control010080 Extract of Preparation Example 20.0003%112810 0.001%120811 Retinoic Acid in Ethanol0.0003 mM120810 0.001 mM128813
    [176] The tested chicory root extract and retinoic acid obviously increased G6PDH activity in human fibroblasts, thus fighting oxidative stress and environmentally harmful substances, and maintaining and regenerating important components of the skin such as collagen, elastin and glycoproteins. It has a high potential for stimulating time cells.
    [177] Many formulations are shown in Tables 6a and 6b.
    [178] Examples of cosmetic preparations (water, preservatives fill 100% by weight)Composition (INCI) One 2 3 4 5Emulgade SE Glyceryl Sterate (and) Cetearette 12/20 (and) Cetearyl Alcohol (and) Cetyl Palmitate5.05.04.0--Eumulgin B1 ceteareth-12--1.0--Lameform TGI Polyglyceryl-3 Isostearate---4.0-Dehymuls PGPH Polyglyceryl-2 Dipolyhydroxystearate ----4.0Monomuls 90-O 18 Glyceryl Oleate---2.0-Cetiol HE PEG-7 Glyceryl Cocoate----2.0Cetiol OE dicaprylyl ether---5.06.0Cetiol PGL hexyldecanol (and) hexyldecyl laurate--3.010.09.0Cetiol SN cetearyl isononanoate3.03.0---Cetiol V decyl oleate3.03.0---Myritol 318 coco caprylate caprate--3.05.05.0 beeswax---7.05.0Nutrilan Elastin E20 Hydrolyzed Elastin2.0----Nutrilan I-50 Hydrolyzed Collagen-2.0---Gluadin AGP Hydrolyzed Wheat Gluten--0.5--Gluadin WK sodium cocoyl hydrolyzed wheat protein---0.50.5 Extract of Preparation1.01.01.01.01.0Hydagen CMF Chitosan1.01.01.01.01.0 Magnesium Sulfate Heptahydrate---1.01.0 Glycerin (86 wt.%)3.03.05.05.03.0 (1) soft cream, (2,3) moisturizing emulsion, (4,5) night cream
    [179] Examples of cosmetic preparations (water, preservatives fill 100% by weight)Composition (INCI) 6 7 8 9 10 11 12 13 14 15Dehymuls PGPH Polyglyceryl-2 Dipolyhydroxystearate 4.03.0-5.0------Lameform TGI Polyglyceryl-3 Diisostearate2.01.0--------Emulgade PL 68/50 cetearyl glucoside (and) cetearyl alcohol----4.0---3.0-Eumulgin B2 cethearet-20-------2.0--Tegocare PS Polyglyceryl-3 Methylglucose Distearate--3.0---4.0---Eumulgin VL 75 polyglyceryl-2 dipolyhydroxystearate (and) lauryl glucoside (and) glycerin-----3.5--2.5- beeswax3.02.05.02.0------Cutina GMS Glyceryl Stearate-----2.04.0--4.0Lanette O cetearyl alcohol--2.0-2.04.02.04.04.01.0Antaron V 216 PVP / hexadecene copolymer-----3.0---2.0Myritol 818 cocoglycerides5.0-10.0-8.06.06.0-5.05.0Finsolv TN C12 / 15 Alkyl Benzoate-6.0-2.0--3.0--2.0Cetiol J 600 Orail Erucate7.04.03.05.04.03.03.0-5.04.0Cetiol OE dicaprylyl ether3.0-6.08.06.05.04.03.04.06.0 Mineral oil-4.0-4.0-2.0-1.0--
    [180] Examples of cosmetic preparations (water, preservatives fill 100% by weight)Composition (INCI) 6 7 8 9 10 11 12 13 14 15Cetiol PGL hexadecanol (and) hexyldecyl laurate 7.03.07.04.0 1.0 Bis-abolol1.21.21.21.21.21.21.21.21.21.2 Extract of Preparation1.01.01.01.01.01.01.01.01.01.0Hydagen CMF Chitosan1.01.01.01.01.01.01.01.01.01.0Copherol F 1300 Tocopherol / Tocopheryl Acetate0.51.01.02.01.01.01.02.00.52.0Neo heliopan Hydro Sodium Phenylbenzimidazole Sulfonate3.0 3.0 2.0 2.0 Neo heliopan 303 octocrylene 5.0 4.05.0 10.0Neo heliopan BB Benzophenone-31.5 2.01.5 2.0 Neo heliopan E 1000 Isoamyl p-methoxycinnamate5.0 4.0 2.02.04.010.0 Neo heliopan AV octyl methoxycinnamate4.0 4.03.02.03.04.0 10.02.0Uvinul T 150 octyl driazone2.04.03.01.01.01.04.03.03.03.0 zinc oxide 6.06.0 4.05.0 Titanium dioxide 5.0 Glycerin (86 wt.%)5.05.05.05.05.05.05.05.05.05.0 (6) W / O sunscreen cream, (7-9) W / O sunscreen lotion, (10, 12, 14) O / W sunscreen lotion, (11, 13, 15) O / W sunscreen cream
    权利要求:
    Claims (22)
    [1" claim-type="Currently amended] Cosmetic preparations containing an effective amount of at least one caffeic acid ester.
    [2" claim-type="Currently amended] The formulation according to claim 1, which contains an ester of caffeic acid and hydroxycarboxylic acid.
    [3" claim-type="Currently amended] The formulation according to claim 1 or 2, which contains an ester of caffeic acid with citric acid and / or tartaric acid.
    [4" claim-type="Currently amended] The preparation according to any one of claims 1 to 3, characterized in that it contains monocafeoyl tartaric acid (caftaric acid), dicafeoyl tartaric acid (chicory acid) or mixtures thereof.
    [5" claim-type="Currently amended] The formulation according to any one of claims 1 to 4, which contains a caffeic acid ester corresponding to formula (III)
    [Formula III]
    [Wherein, the substituent R independently of each other represents a hydrogen or a hydroxyl group, and R 1 is a hydroxyl or a residue of a dicarboxylic acid or a dicarboxylic acid monoester].
    [6" claim-type="Currently amended] 6. The formulation according to claim 5, wherein R 1 contains an ester of formula III which is a residue of oxalic acid monomethyl ester.
    [7" claim-type="Currently amended] The formulation according to any one of claims 1 to 6, which further contains free caffeic acid.
    [8" claim-type="Currently amended] 8. The formulation according to any one of claims 1 to 7, characterized in that it contains an extract of a plant or bacteria containing an effective amount of caffeic acid ester.
    [9" claim-type="Currently amended] The formulation according to claim 8, which contains a plant extract of the genus Echinacea.
    [10" claim-type="Currently amended] 10. The formulation according to claim 9, which contains extracts of chicory and / or coffee beans.
    [11" claim-type="Currently amended] The formulation of claim 8 which contains extracts of Baccharis genistelloide bacteria and / or Achyrocline satureiode bacteria.
    [12" claim-type="Currently amended] The formulation according to any one of claims 1 to 11, which contains caffeic acid ester in an amount of 0.01 to 5% by weight.
    [13" claim-type="Currently amended] Use of caffeic acid esters used for the preparation of cosmetic preparations.
    [14" claim-type="Currently amended] Use according to claim 13, characterized in that the cosmetic preparation is a skin treatment preparation.
    [15" claim-type="Currently amended] Use of caffeic acid esters used as anti-inflammatory.
    [16" claim-type="Currently amended] Use of caffeic acid esters used to reduce the release of inflammation-promoting substances from mast cells, or basophilic or eosinophilic leukocytes.
    [17" claim-type="Currently amended] Use of caffeic acid esters as an active ingredient against acne and rosacea.
    [18" claim-type="Currently amended] Use of caffeic acid esters used to protect cells against oxidative stress.
    [19" claim-type="Currently amended] Use of caffeic acid esters used to protect cells against UV-A and UV-B rays.
    [20" claim-type="Currently amended] Use of caffeic acid esters used to reduce the production of reactive oxygen species (ROS) in respiratory bursts.
    [21" claim-type="Currently amended] Use of caffeic acid esters as active anti-aging components.
    [22" claim-type="Currently amended] Use of caffeic acid esters as an active ingredient for protecting sensitive skin.
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    同族专利:
    公开号 | 公开日
    WO2002094210A2|2002-11-28|
    JP2005506310A|2005-03-03|
    EP1487400A2|2004-12-22|
    US20040170581A1|2004-09-02|
    AU2002338914A1|2002-12-03|
    WO2002094210A3|2004-10-21|
    EP1260212A1|2002-11-27|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    法律状态:
    2001-05-21|Priority to EP01401318A
    2001-05-21|Priority to EP01401318.9
    2002-05-11|Application filed by 코니스 프랑스, 에스.에이.
    2002-05-11|Priority to PCT/EP2002/005201
    2004-03-10|Publication of KR20040021604A
    优先权:
    申请号 | 申请日 | 专利标题
    EP01401318A|EP1260212A1|2001-05-21|2001-05-21|Cosmetic composition|
    EP01401318.9|2001-05-21|
    PCT/EP2002/005201|WO2002094210A2|2001-05-21|2002-05-11|Cosmetic agents|
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