EP1511460A1 - Preparation cosmetique et/ou dermatologique contenant des 2,3-dibenzyle-butyrolactones - Google Patents

Preparation cosmetique et/ou dermatologique contenant des 2,3-dibenzyle-butyrolactones

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Publication number
EP1511460A1
EP1511460A1 EP03730088A EP03730088A EP1511460A1 EP 1511460 A1 EP1511460 A1 EP 1511460A1 EP 03730088 A EP03730088 A EP 03730088A EP 03730088 A EP03730088 A EP 03730088A EP 1511460 A1 EP1511460 A1 EP 1511460A1
Authority
EP
European Patent Office
Prior art keywords
cosmetic
polyethylene glycol
derivatives
skin
glycosides
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.)
Ceased
Application number
EP03730088A
Other languages
German (de)
English (en)
Inventor
Franz STÄB
Rainer Wolber
Thomas Blatt
Ludger Kolbe
Claudia Mundt
Stefan Gallinat
Kirsten Venzke
Tom Karen Dieck
Ute Breitenbach
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 EP1511460A1 publication Critical patent/EP1511460A1/fr
Ceased 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
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/006—Antidandruff preparations
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/602—Glycosides, e.g. rutin
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • 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
    • A61Q19/08—Anti-ageing preparations
    • 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
    • A61Q19/10—Washing or bathing 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
    • 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
    • A61Q5/02—Preparations for cleaning the hair
    • 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
    • A61Q5/12—Preparations containing hair conditioners

Definitions

  • the present invention relates to a cosmetic and / or dermatological preparation containing one or more 2,3-dibenzylbutyrolactone derivatives and / or their glycosides in addition to any other cosmetic and / or dermatological active ingredients, auxiliaries and additives.
  • the skin is the largest human organ. It fulfills a variety of functions (e.g. heat regulation, sensory organ for sensation of touch and warmth, barrier function, protection against dehydration).
  • the skin can be divided into three histologically separable layers:
  • the outermost layer is the epidermis. As a boundary layer, it forms the actual protective cover against the environment. At around a tenth of the total thickness, it is also the thinnest layer of the skin.
  • the epidermis is a stratified tissue in which the outer layer, the stratum corneum, is the important part for the barrier function. It is worn in contact with the environment and is therefore in a constant process of renewal, whereby fine scales are continuously released to the outside and corneal and lipid material horned from the inside is reproduced.
  • the dermis Under the epidermis is the dermis, also known as the corium or dermis.
  • the main function of this mesodermal connective tissue is to supply the epidermis. It is formed from elastic, collagen and reticular fibers and has a large number of plasma and mast cells.
  • the subcutis (subcutis) consists of loose connective tissue with more or less numerous stored fat cells. It serves as heat protection, as mechanical padding and as a store for nutrients and water.
  • Chronological skin aging is e.g. caused by endogenous, genetically determined factors. In the epidermis and dermis it occurs due to aging e.g. the following structural damage and malfunctions, which may also fall under the term "senile xerosis":
  • Exogenous factors such as UV light and chemical pollutants, can be cumulative and e.g. accelerate or complement the endogenous aging processes.
  • exogenous factors e.g. the following structural damage and functional disorders in the skin that go beyond the extent and quality of the damage with chronological aging:
  • the microorganisms decompose the sebum into glycerol and fatty acids, which stimulates the sebum glands to produce more and attacks and destroys the follicle walls in the skin. This causes inflammation in the skin (pustules, lumps, cysts), which often only heal with scars, which permanently damages the visual appearance of people suffering from blemished skin.
  • the task of cosmetic skin care is to strengthen or strengthen the natural function of the skin as a barrier against environmental influences (e.g. dirt, chemicals, microorganisms) and against the loss of the body's own substances (e.g. water, natural fats, electrolytes) restore.
  • environmental influences e.g. dirt, chemicals, microorganisms
  • body's own substances e.g. water, natural fats, electrolytes
  • the object is surprisingly achieved by a cosmetic and / or dermatological preparation comprising one or more 2,3-dibenzylbutyrolactone derivatives and / or their glycosides in addition to any other cosmetic and / or dermatological active ingredients, auxiliaries and additives.
  • the preparation according to the invention is highly effective against all signs of aging of the skin.
  • the appearance of wrinkles and wrinkles as well as age spots is significantly suppressed.
  • Existing wrinkles and wrinkles are reduced, sagging skin is tightened again and gets a fresh and youthful appearance.
  • Existing age spots can be reduced by using the preparation according to the invention.
  • Degenerated skin areas are regenerated, circulatory disorders are markedly reduced. Even itching and the sensation of stress on the skin subside noticeably.
  • the preparation according to the invention is suitable as an effective, yet mild agent for the prophylaxis and treatment of impure skin and its pathological excesses in the form of acne.
  • the 2,3-dibenzylbutyrolactone derivatives according to the invention and / or their glycosides are derived from the 2,3-dibenzylbutyrolactone also according to the invention, which is characterized by the following structure:
  • 2,3-Dibenzylbutyrolacton According to the invention, 2,3-dibenzylbutyrolactone, 2,3-dibenzylbutyrolactone derivatives and / or their glycosides in all their stereoisomeric forms, which can be present both as a racemate and in enantiomerically pure form, and also in racemic mixtures with different enantiomer proportions.
  • the formulation comprises 2,3-dibenzylbutyrolactone derivatives and / or their glycosides also the 2,3-dibenzylbutyrolactone.
  • the cosmetic and / or dermatological preparation according to the invention is preferably present in the form of an emulsion.
  • the preparations within the meaning of the present invention can preferably contain, in addition to one or more oil phases, additionally one or more water phases and, for example, in the form of W / O- (water in oil), W / S- (water in silicone oil), O / W (oil in water), B / W (silicone oil in water) emulsion are present.
  • W / O- water in oil
  • W / S- water in silicone oil
  • O / W oil in water
  • B / W silicone oil in water
  • they can advantageously also be present in so-called multiple emulsions, for example W / O / W or O / W / O emulsions.
  • Such formulations may preferably also be a microemulsion (e.g.
  • the preparations in the sense of the present invention can also be almost anhydrous (water content below 5% by weight based on the total weight of the preparation).
  • Aqueous solutions are also advantageous according to the invention.
  • the preparations according to the invention are also advantageous according to the invention in the form of lipodispersions, gels, solid sticks or aerosols.
  • Preparations within the meaning of the present invention can e.g. in the form of a cream, a lotion, a cosmetic milk, a mousse cream from an aerosol container.
  • the concentration of one or more 2,3-dibenzylbutyrolactone derivatives and / or their glycosides, based on the total weight of the preparation is advantageously from 0.001 to 10% by weight, preferably from 0.05 to 5% by weight. % and very particularly preferably from 0.01 to 2% by weight, in each case based on the total weight of the preparation.
  • the 2,3-dibenzylbutyrolactone derivatives according to the invention and / or their glycosides can advantageously be added to the preparation according to the invention in the form of plant extracts.
  • Aqueous-alcoholic extracts from plants have proven particularly useful.
  • extracts and distillates obtained with other extraction forms and methods for example extracts obtained with carbon dioxide as the extractant and steam distillates, can also be advantageously formulated into the preparations according to the invention.
  • Arctiin, arctigenin, Prestegan B, matairesinol, tracheloside and / or trachelogenin are used as 2,3-dibenzylbutyrolactone derivatives preferred according to the invention and / or their glycosides.
  • the derivatives with the following stereochemical structure are particularly preferred:
  • Arctiin and prestegan B are very particularly preferred according to the invention.
  • the 2,3-dibenzylbutyrolactone derivatives and / or their glycosides according to the invention can easily be incorporated into conventional cosmetic and / or dermatological preparations, such as sunscreen preparations, skin care preparations, anti-wrinkle preparations, but also other preparations, for example pharmaceutical preparations.
  • Cosmetic and / or dermatological preparations generally contain a large number of auxiliaries and active ingredients which can also be used advantageously in the preparations according to the invention.
  • the customary antioxidants can be used in the preparations which contain the 2,3-dibenzylbutyrolactone derivatives and / or their glycosides.
  • the antioxidants are advantageously selected from the group consisting of amino acids (eg glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (eg urocanic acid) and their derivatives, peptides such as D, L-carnosine, D-carnosine, L- Camosin and their derivatives (e.g. anserine), carotenoids, carotenes (e.g. ⁇ -carotene, ⁇ -carotene, lycopene) and their derivatives, aurothioglucose, propylthiouracil and other thiols (e.g.
  • amino acids eg glycine, histidine, tyrosine, tryptophan
  • imidazoles eg urocanic acid
  • peptides such as D, L-carnosine, D-carnosine, L- Camosin and their derivatives (e.g. anserine)
  • thioredoxin glutathione, cysteine, cystine, cystamine and their glycosyl -, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, ⁇ -linoleyl, cholesteryl and glyceryl esters) and their salts, dilauryl thiodipropionate, distearyl thiodipropionate , Thiodipropionic acid and its derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) as well as (metal) chelators (e.g.
  • ⁇ -hydroxy fatty acids palmitic acid, phytic acid, lactoferrin
  • ⁇ -hydroxy acids e.g. citric acid, Lactic acid, malic acid
  • humic acid bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives
  • unsaturated fatty acids and their derivatives e.g. ⁇ -linolenic acid, linoleic acid, oleic acid
  • folic acid and their derivatives alanine diacetic acid, flavonoids, polyphenols, catechins, vitamin C and derivatives (e.g.
  • the amount of the antioxidants (one or more compounds) in the preparations is preferably 0.001 to 10% by weight, particularly preferably 0.025 to 2.0% by weight, in particular 0.05 to 1.0% by weight, based on the total weight of the preparation.
  • vitamin A or vitamin A derivatives, or carotenes or derivatives thereof are the antioxidant or antioxidants, is advantageous to choose their respective concentrations, based on the range of 0.001 to 10 wt .-% "based on the total weight of the formulation, to choose.
  • vitamin E and / or its derivatives represent the antioxidant (s)
  • active substances in the sense of the present invention are natural active substances and / or their derivatives, such as.
  • Hop or hop malt extract and / or soy extracts and / or clover extracts can advantageously also be added to the preparations according to the invention in a concentration of 0.001 to 10% by weight, based on the total weight of the preparation.
  • Recipes according to the invention which, for. B. known Antifaltenwifkstoffe such as flavone glycosides (especially ⁇ -glycosylrutin), coenzyme Q10, vitamin E and / or derivatives and the like, are particularly advantageous for the prophylaxis and treatment of cosmetic or dermatological skin changes such as z. B. occur with skin aging (such as dryness, roughness and formation of dry wrinkles, itching, reduced re-greasing (e.g. after washing), visible vasodilation (telangiectasias, cuperosis), flaccidity and formation of wrinkles and fine lines, local hyper-, hypo- and incorrect pigmentations (e.g. age spots), increased susceptibility to mechanical stress (e.g. cracking) and the like). Furthermore, they are advantageously suitable for the treatment and prophylaxis of the clinical appearance of dry or rough skin and for the treatment and prophylaxis of the symptoms of UV-light-induced skin aging (English photoaging).
  • skin aging such
  • the cosmetic and / or dermatological preparations according to the invention can contain cosmetic auxiliaries, as are usually used in such preparations, e.g.
  • emulsifiers As emulsifiers, preservatives, preservation aids, bactericides, perfumes, UV light protection filters, skin bleaching agents, self-tanners, repellents, substances to prevent foaming, dyes, pigments that have a coloring effect, thickeners, moisturizing and / or moisturizing substances Fillers that improve the feeling on the skin, fats, oils, waxes or other common components of a cosmetic or dermatological formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.
  • Medical topical compositions in the sense of the present invention generally contain one or more medicaments in an effective concentration.
  • medicaments in an effective concentration.
  • Preparations according to the invention can also advantageously contain substances which absorb UV radiation in the UVB range, the total amount of filter substances being, for example, 0.1% by weight to 30% by weight, preferably 0.5 to 10% by weight. , in particular 1.0 to 6.0% by weight, based on the total weight of the preparations, in order to provide cosmetic preparations which protect the hair or the skin from the entire range of ultraviolet radiation. They can also serve as a sunscreen for the hair.
  • the preparations according to the invention contain UVB filter substances, they can be oil-soluble or water-soluble.
  • Oil-soluble UVB filters which are advantageous according to the invention are, for example: 3-benzylidene camphor derivatives, preferably 3- (4-methylbenzylidene) camphor, 3-
  • 4-aminobenzoic acid derivatives preferably 4- (dimethylamino) benzoic acid (2-ethylhexyl) ester, 4- (dimethylamino) benzoic acid amyl ester;
  • Esters of cinnamic acid preferably 4-methoxycinnamic acid (2-ethylhexyl) ester, 4-methoxycinnamic acid isopentyl ester;
  • esters of salicylic acid preferably salicylic acid (2-ethylhexyl) ester, salicylic acid (4-isopropylbenzyl) ester, salicylic acid homomethyl ester,
  • Esters of benzalmalonic acid preferably 4-methoxybenzalmalonic acid di (2-ethylhexyl) ester,
  • Triethanolammonium salt as well as the sulfonic acid itself
  • Sulfonic acid derivatives of benzophenones preferably 2-hydroxy-4-methoxy-benzophenone-5-sulfonic acid and their salts;
  • Sulfonic acid derivatives of 3-benzylidene camphor such as 4- (2-oxo-3-bornylidene-methyl) benzenesulfonic acid, 2-methyl-5- (2-oxo-3-bomylidene-methyl) sulfonic acid and its salts and 1 ) 4- di (2-oxo-10-sulfo-3-bomylidenemethyl) benzene and its salts (the corresponding 10-sulfato compounds, for example the corresponding sodium, potassium or triethanolammonium salt), also as benzene-1, Denotes 4- di (2-oxo-3-bomylidenemethyl-10-sulfonic acid,
  • Hydroxybenzophenone derivatives such as, for example, 2- (4-diethylamino-2-hydroxybenzoyl) benzoic acid hexyl ester, which is available, for example, from BASF under the trade name Uvinul® A Plus.
  • Benzoxazole derivatives such as, for example, 2,4-bis- [5-1 (dimethylpropyl) benzossazol-2-yl- (4-phenyl) imino] -6- (2-ethylhexyl) imino-1, 3.5 triazine (CAS no .: 288254-16-0), which is available, for example, from 3V Sigma under the trade name UVASorb® K2A.
  • UVB filters which can be used in combination with the active compound combinations according to the invention, is of course not intended to be limiting.
  • UVA filters that are usually contained in cosmetic preparations. These substances are preferably derivatives of dibenzoylmethane, in particular 1- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1,3-dione and 1-phenyl-3- (4'-isopropylphenyl) propane-1,3-dione.
  • UVA filters come from the group of triazines, for example the 2,4- • bis - ⁇ [4- (2-ethylhexyloxy) -2-hydroxy] phenyl ⁇ -6- (4-methoxyphenyl) -1 , 3,5-triazine
  • Tinosorb® S and the group of triazoles, such as the 2,2'-methylene-bis- [6-2H-benzotriazol-2yl] -4- (1, 1, 3,3-tetramethylbutyl) phenol
  • Tinosorb® M an advantageous water-soluble UVA filter is the 2'-bis- (1,4-phenylene) -1 H -benzimidazole-4,6-disulfonic acid sodium salt (trade name Neo Heliopan AP®).
  • the quantities used for the UVB combination can be used.
  • Cosmetic and / or dermatological preparations according to the invention advantageously additionally contain inorganic pigments based on metal oxides and / or other metal compounds which are sparingly soluble or insoluble in water, in particular the oxides of titanium (TiO 2 ), zinc (ZnO), iron (eg Fe 2 O 3 ) , Zirconium (ZrO 2 ), silicon (SiO 2 ), manganese (eg MnO), aluminum (AI 2 O 3 ), cerium (eg Ce 2 O 3 ), mixed oxides of the corresponding metals and mixtures of such oxides. Pigments based on TiO 2 are particularly preferred.
  • the inorganic pigments are present in hydrophobic form, ie that they have been treated to be water-repellent on the surface.
  • This surface treatment can be in it exist that the pigments are provided with a thin hydrophobic layer by methods known per se.
  • Such a method consists, for example, in that the hydrophobic surface layer according to a direction
  • n and m are stoichiometric parameters to be used at will, R and R 'are the desired organic residues.
  • hydrophobized pigments shown in analogy to DE-OS 33 14742 are advantageous.
  • Advantageous TiO 2 pigments are available, for example, under the trade names MT 100 T from TAYCA, M 160 from Kemira and T 805 from Degussa.
  • Preparations according to the invention can also contain anionic, nonionic and / or amphoteric surfactants, especially if crystalline or microcrystalline solids, for example inorganic micropigments, are to be incorporated into the preparations according to the invention.
  • Surfactants are amphiphilic substances that can dissolve organic, non-polar substances in water.
  • hydrophilic parts of a surfactant molecule are mostly polar functional groups, for example -COO ' , -OSO 3 2 " , -SO 3 ' , while the hydrophobic parts generally represent non-polar hydrocarbon residues.
  • Surfactants are generally classified according to Art and charge of the hydrophilic part of the molecule. There are four groups:
  • nonionic surfactants generally have carboxylate, sulfate or sulfonate groups as functional groups. In aqueous solution they form negatively charged organic ions in an acidic or neutral environment. Cationic surfactants are characterized almost exclusively by the presence of a quaternary ammonium group. In aqueous solution they form positively charged organic ions in an acidic or neutral environment. Amphoteric surfactants contain both anionic and cationic groups and therefore behave like anionic or cationic surfactants in aqueous solution depending on the pH. They have a positive charge in a strongly acidic environment and a negative charge in an alkaline environment. In the neutral pH range, however, they are zwitterionic, as the following example should illustrate:
  • Non-ionic surfactants do not form ions in an aqueous medium.
  • Anionic surfactants to be used advantageously are acylamino acids (and their salts), such as
  • acylglutamates for example sodium acylglutamate, di-TEA-palmitoylaspartate and sodium caprylic / capric glutamate,
  • acyl peptides for example palmitoyl-hydrolyzed milk protein, sodium cocoyl-hydrolyzed soy protein and sodium / potassium cocoyl-hydrolyzed collagen,
  • sarcosinates for example myristoyl sarcosin, TEA-lauroyl sarcosinate, sodium lauroyl sarcosinate and sodium cocoyl sarcosinate,
  • taurates for example sodium lauroyl taurate and sodium methyl cocoyl taurate
  • Carboxylic acids and derivatives such as
  • carboxylic acids for example lauric acid, aluminum stearate, magnesium alkanolate and zinc undecylenate
  • ester carboxylic acids for example calcium stearoyl lactylate, laureth-6 citrate and sodium PEG-4 lauramide carboxylate
  • ether carboxylic acids for example sodium laureth-13 carboxylate and sodium PEG-6 cocamide carboxylate,
  • Phosphoric acid esters and salts such as DEA-oleth-10-phosphate and dilureth-4-phosphate
  • acyl isethionates e.g. Sodium / ammonium cocoyl isethionate
  • alkylsulfonates for example Natriumcocosmonoglyceridsuifat, sodium C 12 . ⁇ 4 olefinsulfonates sulfonate fin-, sodium lauryl sulfoacetate and magnesium PEG-3 cocamide sulfate,
  • Sulfosuccinates for example dioctyl sodium sulfosuccinate, disodium laureth sulfosuccinate, disodium lauryl sulfosuccinate and disodium undecylenamido MEA sulfosuccinate
  • alkyl ether sulfate for example sodium, ammonium, magnesium, MIPA, TIPA laureth sulfate, sodium and sodium C 12 - 13 pareth
  • alkyl sulfates for example sodium, ammonium and TEA lauryl sulfate.
  • Cationic Surfactants Cationic surfactants to be used advantageously are
  • Quaternary surfactants contain at least one N atom that is covalently linked to 4 alkyl or aryl groups. Regardless of the pH value, this leads to a positive charge.
  • Alkyl betaine, alkyl amidopropyl betaine and alkyl amidopropyl hydroxysulfain are advantageous.
  • the cationic surfactants used in the invention can also preferably be chosen from the group of quaternary ammonium compounds, especially benzyltrialkylammonium chlorides or bromides, such as rylammoniumchlorid Benzyldimethylstea-, further alkyltrialkylammonium salts, for example cetyltrimethylammonium chloride or bromide, chloride Alkyldimethylhydroxyethylammonium- or bromides, dialkyldimethylammonium chlorides or bromides , Alkylamidethyl-trimethylammonium ether sulfates, alkylpyridinium salts, for example lauryl or cetylpyrimidinium chloride, imidazoline derivatives and compounds with a cationic character such as amine oxides, for example alkyldimethylamine oxides or alkylaminoethyldimethylamine oxides. Cetyltrimethylammonium salts are particularly advantageous.
  • acyl / dialkyl ethylenediamine for example sodium acyl amphoacetate, disodium acyl amphodipropionate, disodium alkyl amphodiacetate, sodium acylamphohydroxypropyl sulfonate, disodium acyl amphodiacetate and sodium acyl amphopropionate,
  • N-alkylamino acids for example aminopropylalkylglutamide, alkylaminopropionic acid, sodium alkylimidodipropionate and lauroamphocarboxyglycinate.
  • alkanolamides such as Cocamide MEA / DEA / MI PA
  • amine oxides such as cocoamidopropylamine oxide
  • esters which are formed by esterifying carboxylic acids with ethylene oxide, glycerol, sorbitan or other alcohols,
  • ethers for example ethoxylated / propoxylated alcohols, ethoxylated / propoxylated esters, ethoxylated / propoxylated glycerol esters, ethoxylated / propoxylated cholesterols, ethoxylated / propoxylated triglyceride esters, ethoxylated propoxylated lanolin, ethoxylated / propoxylated polysiloxanes, propoxylated POE ethers and
  • Alkyl polyglycosides such as lauryl glucoside, decyl glycoside and cocoglycoside.
  • the surface-active substance can be present in the preparations according to the invention in a concentration between 1 and 30% by weight, based on the total weight of the preparations.
  • the cosmetic or dermatological preparations according to the invention can be composed as usual and can be used for the treatment, care and cleaning of the skin and / or hair and as a make-up product in decorative cosmetics. Correspondingly, depending on their structure, they can be used, for example, as skin protection creams, cleansing milk, sun protection lotion, nutritional creams, day or night creams, etc. It may be possible and advantageous to use the preparations according to the invention as the basis for pharmaceutical formulations.
  • the preparations according to the invention contain e.g. 0.001 to 30% by weight, preferably 0.01% to 10% by weight, but in particular 0.1% to 5% by weight, in each case based on the total weight of the preparations of the active compounds according to the invention ,
  • Cosmetic and dermatological preparations for protecting the hair from UV rays according to the invention are, for example, shampooing agents, preparations which are used when rinsing the hair before or after the shampooing, before or after the permanent wave treatment, before or after the coloring or discoloration of the Hair is applied to preparations for blow-drying or pickling hair, preparations for coloring or decolouring, to a styling and treatment lotion, a hair lacquer or to permanent waving agents.
  • the lipid phase of the cosmetic and / or dermatological preparations according to the invention can advantageously be selected from the following group of substances: mineral oils, mineral wax oils, such as triglycerides of capric or caprylic acid, and also natural oils such as e.g. Castor oil;
  • Fats, waxes and other natural and synthetic fat bodies preferably
  • Esters of fatty acids with alcohols with a low C number e.g. with isopropanol, propyl lenglycol or glycerin, or esters of fatty alcohols with low C number alkanoic acids or with fatty acids; benzoates;
  • Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiloxanes and mixed forms thereof.
  • the oil phase of the preparation of the present invention is advantageously selected from the group of the esters from saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 3 to 30 carbon atoms and saturated and / or unsaturated, branched and / or unbranched alcohols a chain length of 3 to 30 carbon atoms, from the group of esters of aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols of a chain length of 3 to 30 carbon atoms.
  • ester oils can then advantageously be selected from the group of isopropyl myristate, isopropyl palmitate, isopropyl stearate, isopropyl oleate, n-butyl stearate, n-hexyl laurate, n-decyl oleate, isooctyl stearate, isononyl stearate, isononylisononanoate, 2-ethyl-2-ethylhexyl palmitate 2-octyldodecyl palmitate, oleyl oleate, olerlerucate, erucyl oleate, erucylerucate and synthetic, semisynthetic and natural mixtures of such esters, for example Jojoba oil.
  • the oil phase can advantageously be selected from the group of branched and unbranched hydrocarbons and waxes, the silicone oils, the dialkyl ethers, the group of saturated or unsaturated, branched or unbranched alcohols, and also the fatty acid triglycerides, especially the triglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 8 to 24, in particular 12 - 18 carbon atoms.
  • the fatty acid triglycerides can, for example, advantageously be selected from the group of synthetic, semisynthetic 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.
  • oil phase is advantageously selected from the group consisting of 2-ethylhexyl isostearate, octyldodecanol, isotridecyl isononanoate, isoeicosane, 2-ethylhexyl cocoate, C 12 -i5-alkylbenzoate, caprylic capric acid triglyceride, dicaprylyl ether, dicaprylyl carbonate.
  • Particularly advantageous are mixtures of C 12 .i5 benzoate and 2-ethylhexyl isostearate, mixtures of C 12 -i 5 alkyl benzoate and isotridecyl isononanoate and mixtures of C 2 -i 5 alkyl benzoate, 2-ethylhexyl isostearate and isotridecyl isononanoate.
  • hydrocarbons paraffin oil, squalane and squalene can be used advantageously for the purposes of the present invention.
  • the oil phase can also advantageously have a content of cyclic or linear silicone oils or consist entirely of such oils, although it is preferred to use an additional content of other oil phase components in addition to the silicone oil or the silicone oils.
  • Such silicones or silicone oils can be present as monomers, which are generally characterized by structural elements, as follows:
  • Linear silicones with several siloxyl units which can advantageously be used according to the invention are generally characterized by structural elements as follows;
  • silicon atoms can be substituted with the same or different alkyl radicals and / or aryl radicals, which are generally represented here by the radicals R ⁇ - Rj (to say that the number of different radicals is not necessarily limited to up to 4), m can assume values from 2 - 200,000.
  • Cyclic silicones to be used advantageously according to the invention are generally characterized by structural elements as follows where the silicon atoms can be substituted with the same or different alkyl radicals and / or aryl radicals, which are generally represented here by the radicals R1-R (to say that the number of different radicals is not necessarily limited to up to 4), n can take values from 3/2 to 20. Broken values for n take into account that there may be odd numbers of siloxyl groups in the cycle.
  • Cyclomethicone e.g. decamethylcyclopentasiloxane
  • silicone oils can also be used advantageously for the purposes of the present invention, for example undecamethylcyclotrisiloxane, polydimethylsiloxane, poly (methylphenylsiloxane), cetyldimethicone, behenoxydimethicone.
  • silicone oils of a similar constitution to the compounds described above, the organic side chains of which are derivatized, for example polyethoxylated and / or polypropoxylated.
  • these include, for example, polysiloxane-polyalkyl-polyether copolymers such as the cetyl-dimethicone copolyol, the (cetyl-dimethicone copolyol (and) polyglyceryl-4-isostearate (and) hexyl laurate)
  • 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 lower C-number, and 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 monoethyl ether and similar products, furthermore low C number alcohols, for example ethanol, isopropanol, 1, 2-propanediol, glycerol and in particular one or more thickeners, which or which can advantageously be selected from the group silicon dioxide, aluminum silicates.
  • alcohols, diols or polyols of lower C-number, and their ethers preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoe
  • Preparations according to the invention particularly advantageously contain one or more hydrocolloids.
  • These hydrocolloids can advantageously be selected from the group of the gums, polysaccharides, cellulose derivatives, layered silicates, polyacrylates and / or other polymers.
  • Preparations according to the invention which are present as hydrogels contain one or more hydrocolloids. These hydrocolloids can advantageously be selected from the aforementioned group.
  • Gums include plant or tree sap that harden in the air and form resins or extracts from aquatic plants. Gum arabic, locust bean gum, tragacanth, karaya, guar gum, pectin, gellan gum, carrageenan, agar, algine, chondrus, xanthan gum can advantageously be selected from this group for the purposes of the present invention.
  • derivatized gums such as e.g. Hydroxy-propyl guar (Jaguar® HP 8).
  • polysaccharides and derivatives are e.g. Hyaluronic acid, chitin and chitosan, chondroitin sulfates, starch and starch derivatives.
  • cellulose derivatives are e.g. Methyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl methyl cellulose.
  • Layered silicates include naturally occurring and synthetic clays such as montmorillonite, bentonite, hectorite, laponite, magnesium aluminum silicates such as Veegum®. These can be used as such or in modified form such as stearylalkonium hectorites. Furthermore, silica gels can also advantageously be used.
  • the polyacrylates include e.g. Carbopol types from Goodrich (Carbopol 980, 981, 1382, 5984, 2984, ETD 2001, ETD 2020, ETD 2050, Ultrez 10 or Pemulen TR1 & TR2).
  • Carbopol types from Goodrich (Carbopol 980, 981, 1382, 5984, 2984, ETD 2001, ETD 2020, ETD 2050, Ultrez 10 or Pemulen TR1 & TR2).
  • polymers e.g. Polyacrylamides (Seppigel, 305), polyvinyl alcohols, PVP, PVP / VA copolymers, polyglycols.
  • Preparations according to the invention in the form of emulsions contain one or more emulsifiers.
  • emulsifiers can advantageously be selected from the group of nonionic, anionic, cationic or amphoteric emulsifiers.
  • nonionic emulsifiers are a) partial and fatty acid ester of polyhydric alcohols and ethoxylated derivatives thereof (eg. As glyceryl monostearate, sorbitan stearates, Glycerylstearylcitrate, Sucrosestearate) b) ethoxylated fatty alcohols and fatty acids c) ethoxylated fatty amines, fatty acid amides, fatty acid alkanolamides d) alkylphenol polyglycol ethers (such as Triton X) e) Sugar derivatives (esters and / or ethers of glucose, sucrose and other sugars; e.g. alkyl polyglycosides such as polyglyceryl-3-methylglucose distearate, methylglucose sesquistearate)
  • polyhydric alcohols and ethoxylated derivatives thereof eg. As glyceryl monostearate,
  • the anionic emulsifiers include a) soaps (e.g. sodium stearate) b) fatty alcohol sulfates c) mono-, di- and trialkylphosphonic acid esters and their ethoxylates
  • the cationic emulsifiers include a) quaternary ammonium compounds with a long-chain aliphatic radical, e.g. Distearyldimonium Chloride
  • amphoteric emulsifiers include a) alkylamininoalkane carboxylic acids b) betaines, sulfobetaines c) imidazoline derivatives
  • emulsifiers which include beeswax, wool wax, lecithin and sterols.
  • O / W emulsifiers can, for example, advantageously be selected from the group of polyethoxylated or polypropoxylated or polyethoxylated and polypropoxylated products, for example: - the fatty alcohol ethoxylates of the ethoxylated wool wax alcohols, the polyethylene glycol ethers of the general formula RO - (- CH 2 -CH 2 -O -) n -R ', the fatty acid ethoxylates of the general formula
  • RO - (- CH 2 -CH 2 -O-) n -CH 2 -COOH and n represent a number from 5 to 30, - the polyoxyethylene sorbitol fatty acid esters, the alkyl ether sulfates of the general formula RO - (- CH 2 -CH 2 -O- ) n -SO 3 -H of the fatty alcohol propoxylates of the general formula
  • RO - (- CH 2 -CH (CH 3 ) -O-) n -H the polypropylene glycol ether of the general formula RO - (- CH 2 -CH (CH 3 ) -O-) n -R ⁇ of the propoxylated wool wax alcohols, the etherified fatty acid propoxylates
  • the polyethoxylated or polypropoxylated or polyethoxylated and polypropoxylated O / W emulsifiers selected are particularly advantageously selected from the group of substances with HLB values of 11-18, very particularly advantageously with HLB values of 14.5-15. 5, provided the O / W emulsifiers have saturated radicals R and R '. If the O / W emulsifiers have unsaturated radicals R and / or R ', or if isoalkyl derivatives are present, the preferred HLB value of such emulsifiers can also be lower or higher.
  • fatty alcohol ethoxylates from the group of ethoxylated stearyl alcohols, cetyl alcohols, cetyl stearyl alcohols (cetearyl alcohols).
  • cetyl alcohols cetyl stearyl alcohols
  • cetearyl alcohols cetearyl alcohols
  • Polyethylene glycol (12) lauryl ether (Laureth-12), polyethylene glycol (12) iso lauryl ether (Isolureth-12).
  • Sodium laureth-11 carboxylate can advantageously be used as the ethoxylated alkyl ether carboxylic acid or its salt.
  • Sodium laureth 1-4 sulfate can advantageously be used as alkyl ether sulfate.
  • Polyethylene glycol (30) cholesteryl ether can advantageously be used as the ethoxylated cholesterol derivative.
  • Polyethylene glycol (25) soyasterol has also proven itself.
  • polyethylene glycol glycerol fatty acid esters from the group polyethylene glycol (20) glyceryl laurate, polyethylene glycol (21) glyceryl laurate, polyethylene glycol (22) glyceryl laurate, polyethylene glycol (23) glyceryl laurate, polyethylene glycol (6) glyceryl capethylene / caprinate 20 ) glyceryl oleate, polyethylene glycol (20) glyceryl isostate, polyethylene glycol (18) glyceryl oleate / cocoate.
  • sorbitan esters from the group consisting of polyethylene glycol (20) sorbitan monolaurate, polyethylene glycol (20) sorbitan monostearate, polyethylene glycol (20) sorbitan monoisostearate, polyethylene glycol (20) sorbitan monopalmitate, polyethylene glycol (20) sorbitan monooleate.
  • W / O emulsifiers that can be used are: fatty alcohols with 8 to 30 carbon atoms, monoglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 8 to 24, in particular 12-18, carbon atoms, diglycerol esters saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 8 to 24, in particular 12 - 18 C atoms, monoglycerol ethers saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 8 to 24, in particular 12 - 18 C - Atoms, diglycerol ethers of saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 8 to 24; in particular 12-18 C atoms, propylene glycol esters of saturated and / or unsaturated, branched and
  • W / O emulsifiers are glyceryl stearate Glycerylmonoiso-, glyceryl monomyristate monoisostearate, glyceryl, diglyceryl monostearate, Diglyceryl-, propylene glycol, propylene glycol monoisostearate glycol, propylene colmonocaprylat, advice propylene glycol, sorbitan, Sorbitanmonolau-, sorbitan, Sorbitanmonoisooleat, sucrose, cetyl alcohol, stearyl alcohol, Arachidyl alcohol, behenyl alcohol, isobehenyl alcohol, selachyl alcohol, chimyl alcohol, polyethylene glycol (2) stearyl ether (steareth-2), glyceryl monolaurate, glyceryl monocaprinate, glyceryl monocaprylate.
  • W / O emulsifiers are glyceryl stearate Glyce
  • cyclodextrins and / or cyclodextrin derivatives are understood to mean the native cyclodextrins ⁇ -, ⁇ - and ⁇ -cyclodextrin and the derivatives of these species, in particular all or partially etherified and / or esterified and / or otherwise derivatized on the hydroxyl groups ⁇ -, ⁇ - and ⁇ -cyclodextrins such as ⁇ -cyclodextrin, ⁇ -cyclodextrin, hydroxypropyl- ⁇ -cyclodextrin, hydroxypropyl- ⁇ -cyclodextrin, partly methylated (random Methyl-) ß-cyclodextrin and / or ⁇ -cyclodextrin.
  • cyclodextrins and their derivatives can form inclusion complexes. They are suitable for the "molecular encapsulation" of active ingredients (e.g. as a protective coating for sensitive molecules in cosmetic and pharmaceutical formulations).
  • cyclodextrins or cyclodextrin-guest inclusion complexes or the cyclodextrin-substance mixtures used according to the invention can be incorporated into common cosmetic or dermatological formulations without difficulty.
  • the cyclodextrin and / or their derivatives are advantageously used in a concentration of 0.0005 to 20.0% by weight, preferably in a concentration of 0.01 to 10% by weight and particularly preferably in a concentration of 0, 1 to 5.0% by weight, based on the total weight of the preparation used.
  • cyclodextrin species which are particularly preferred according to the invention are ⁇ -cyclodextrin and hydroxypropyl- ⁇ -cyclodextrin.
  • the use of one or more 2,3-dibenzylbutyrolactone derivatives and / or their glycosides for the production of a medicament for the treatment and / or prophylaxis of skin aging symptoms.
  • Dibenzylbutyrolactone derivatives and / or their glycosides for the manufacture of a medicament for the treatment and / or prophylaxis of impure skin and acne according to the invention.
  • Cosmetic according to the invention for the treatment and / or prophylaxis of impure skin and acne.
  • the prophylaxis or the cosmetic or dermatological treatment with the 2,3-dibenzylbutyrolactone derivatives used according to the invention and / or their glycosides or with the cosmetic or topical dermatological preparations with an effective content of 2,3-dibenzylbutyrolactone derivatives used according to the invention and / or their glycosides are carried out in the usual way, in such a way that the 2,3-dibenzylbutyrolactone derivatives used according to the invention and / or their glycosides or the cosmetic or topical dermatological preparations with an effective content of 2,3-dibenzylbutyrolactone derivatives used according to the invention and / or whose glycosides are applied to the affected skin areas.
  • hair care In addition to skin health and skin care, another area of cosmetics is hair care.
  • the preparations according to the invention are surprisingly suitable for the treatment and care of the appendages of the skin, ie the nails, the sweat glands, the sebaceous glands, the hair follicles and in particular the hair.
  • the treatment and care of oily hair and / or dandruff is advantageous according to the invention, since these manifestations have a certain relationship with the manifestations of impure skin (increased sebum production) or dry, inflammatory skin.
  • the preparations according to the invention in the form of shampoos, conditioning, rinses and cures can advantageously be used according to the invention.

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Abstract

L'invention concerne une préparation cosmétique et/ou dermatologique contenant un ou plusieurs dérivés de 2,3-dibenzyle-butyrolactone et/ou des glycosides de ceux-ci, outre éventuellement d'autres agents actifs, auxiliaires et additifs cosmétiques et/ou dermatologiques.
EP03730088A 2002-05-27 2003-05-22 Preparation cosmetique et/ou dermatologique contenant des 2,3-dibenzyle-butyrolactones Ceased EP1511460A1 (fr)

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DE10223486 2002-05-27
DE10223486A DE10223486A1 (de) 2002-05-27 2002-05-27 Kosmetische und/oder dermatologische Zubereitung mit 2,3-Dibenzylbutyrolactonen
PCT/EP2003/005347 WO2003099244A1 (fr) 2002-05-27 2003-05-22 Preparation cosmetique et/ou dermatologique contenant des 2,3-dibenzyle-butyrolactones

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