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WO1996038125A1 - COMPOSITIONS COSMETIQUES OU DERMATOLOGIQUES CONTENANT DES OLIGOMERES OU DES POLYMERES D'ACIDES α-HYDROXYCARBOXYLIQUES - Google Patents

COMPOSITIONS COSMETIQUES OU DERMATOLOGIQUES CONTENANT DES OLIGOMERES OU DES POLYMERES D'ACIDES α-HYDROXYCARBOXYLIQUES Download PDF

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Publication number
WO1996038125A1
WO1996038125A1 PCT/EP1996/002354 EP9602354W WO9638125A1 WO 1996038125 A1 WO1996038125 A1 WO 1996038125A1 EP 9602354 W EP9602354 W EP 9602354W WO 9638125 A1 WO9638125 A1 WO 9638125A1
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groups
oligomers
polymers
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branched
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PCT/EP1996/002354
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German (de)
English (en)
Inventor
Sven Gohla
Waltraud Kaden
Jürgen KIELHOLZ
Uta Kruse
Uta Meiring
Jens Nielsen
Franz STÄB
Florian Wolf
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Beiersdorf Ag
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Publication of WO1996038125A1 publication Critical patent/WO1996038125A1/fr

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    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/74—Synthetic polymeric materials
    • A61K31/765—Polymers containing oxygen
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/85—Polyesters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/75—Anti-irritant
    • 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

Definitions

  • Cosmetic or dermatological preparations containing oligomers or polymers of ⁇ -hydroxycarboxylic acids containing oligomers or polymers of ⁇ -hydroxycarboxylic acids
  • the present invention relates to preparations in the field of cosmetic and dermatological skin and hair care, in particular those preparations with low irritation potential or cosmetic or dermatological preparations for prophylaxis, amelioration, elimination or avoidance of skin irritation.
  • the present invention relates to cosmetic and dermatological preparations for the prophylaxis and treatment of cosmetic or dermatological skin changes such as e.g. skin aging.
  • the present invention relates to preparations against the appearance of dry or rough skin.
  • the present invention relates to active substances and preparations containing such active substances for cosmetic and dermatological treatment or prophylaxis of erythematous, inflammatory, allergic or autoimmune-reactive symptoms, in particular dermatoses. Furthermore, the invention relates to the use of such active substances and preparations containing such active substances for immunostimulation of the skin, advantageously also for immunostimulation in the sense of treating injured skin, in particular for treating wounds.
  • the invention relates to preparations with extremely low so-called "stinging potential”.
  • Skin care is primarily understood to mean that 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) is strengthened or restored. If this function is disturbed, there may be an increased absorption of toxic or allergenic substances or an infestation of microorganisms and, as a result, toxic or allergic skin reactions.
  • environmental influences e.g. dirt, chemicals, microorganisms
  • the loss of the body's own substances e.g. water, natural fats, electrolytes
  • the aim of skin care is also to compensate for the loss of fat and water in the skin caused by daily washing. This is especially important when the natural regeneration ability is insufficient.
  • skin care products are intended to protect against environmental influences, especially sun and wind, and to delay the signs of aging.
  • Medical topical compositions generally contain one or more medicaments in an effective concentration.
  • medicaments in an effective concentration.
  • the epidermis is richly equipped with nerves and nerve end devices such as Father Pacini lamellar bodies, Merkel cell neurite complexes and free nerve endings for pain, cold, heat sensation and itching.
  • nerves and nerve end devices such as Father Pacini lamellar bodies, Merkel cell neurite complexes and free nerve endings for pain, cold, heat sensation and itching.
  • This "sensitive skin” differs fundamentally from “dry skin” with thickened and hardened horny layers.
  • Typical reactions of "stinging" to sensitive skin are reddening, tension and burning of the skin as well as itching.
  • “Stinging 'phenomena” can be regarded as disorders to be treated cosmetically.
  • severe itching in particular severe itching in the case of atopy, can also be described as a more serious dermatological disorder.
  • Typical disturbing neurosensory phenomena associated with the terms “stinging” or “sensitive skin” are reddening of the skin, tingling, tingling, tension and burning of the skin and itching. They can be caused by stimulating environmental conditions such as massage, tenside effects, weather influences such as sun, cold, dryness, but also moist heat, heat radiation and UV radiation, such as the sun.
  • citric acid is used to buffer cosmetic and / or dermatological preparations, but also as a synergist for antioxidants in skin and hair cosmetics.
  • DE-OS 42 04 321 describes the use of longer-chain ⁇ -hydroxycarboxylic acids as active ingredients for cosmetic deodorants.
  • US Pat. No. 4,363,815 describes the use of ⁇ -hydroxycarboxylic acids for the treatment of inflammatory skin symptoms.
  • US Pat. No. 4,380,549 describes the use of ⁇ -hydroxycarboxylic acids to relieve the symptoms of dry skin.
  • Other topical fields of application of the ⁇ -hydroxycarboxylic acids are also known, but these few examples already show that the ⁇ -hydroxycarboxylic acids are valuable substances effective on the skin, whether they are cosmetic or pharmaceutical applications.
  • Erythematous skin symptoms also appear as side effects in certain skin diseases or irregularities. For example, the typical rash in the appearance of acne is usually more or less reddened.
  • EP-OS 447 318 describes compositions for the cosmetic or pharmaceutical care of the upper skin layers, which contain polymeric, biodegradable nanoparticles in a suitable carrier, which coat an oily active substance.
  • the polymeric coating materials described also include poly (L) lactic acid, poly (DL) lactic acid, polyglycolic acid and copolymers of lactic and glycolic acid.
  • cosmetic or dermatological preparations according to the invention in particular when the oligomers, polymers, co-oligomers and / or copolymers according to the invention are incorporated into an oil phase, are stable against depolymerization (or de-oligomerization) and their advantageous First have an effect on human skin. Since the oligomers, polymers, co-oligomers and / or copolymers according to the invention gradually release the monomers on which they are based, they are particularly suitable as depot systems or for sustained release.
  • the oligomers, polymers, co-oligomers and / or co-polymers according to the invention also have the advantage, surprisingly, even if their hydrolysis to the underlying monomers has not yet taken place or has not yet taken place completely, to increase the skin moisture.
  • the invention also relates to a process for stabilizing an effective amount of one or more oligomers and / or polymers and / or co-oligomers and / or co-polymers of one or more ⁇ -hydroxycarboxylic acids of the general formula
  • ⁇ -hydroxycarboxylic acids on which the oligomers and / or polymers and / or co-oligomers and / or co-polymers are based are advantageously selected from the group of ⁇ -hydroxyalkanoic acids, which in turn is particularly advantageous from the group of C2- _-Alkyl carboxylic acids can be selected.
  • oligomers and / or polymers and / or co-oligomers and / or copolymers of glycolic acid, lactic acid, ⁇ -hydroxybutyric acid and / or ⁇ -hydroxyvaleric acid are particularly preferred.
  • oligo- or polyglycolides are characterized by their structure
  • Co-oligo- or copolymers of lactic acid and glycolic acid are characterized, for example, by a structure according to the sum of the numbers k and j corresponds to the number n. It is clear to the person skilled in the art that the arrangement of the co-monomers in a co-oligomer or co-polymer can be carried out in blocks, alternating, randomly distributed or according to other arrangement principles. All of these types of arrangement can be used advantageously according to the invention.
  • Oligo- or poly-2-hydroxybutyrates are characterized by the structure
  • Oligo- or poly-2-hydroxyvalerates are characterized by the structure
  • ⁇ -hydroxycarboxylic acids present as enantiomers as basic constituents of the oligomers or polymers which are more beneficial to skin care than their optical antipodes, for example L-lactic acid.
  • the number n for at least 40% by weight of the oligomer and / or polymer and / or co-oligomer and / or co-polymer used is advantageously at least 8, preferably 10.
  • the upper limit for n can in principle remain open, but nevertheless values for n of 60 to 1,000, in particular 200, have proven to be advantageous.
  • polymers which consist of at least 40% by weight of approximately 60,000 monomer units and those which consist of at least 40% by weight of approximately 100,000 monomer units can also be used advantageously.
  • Oligo (DL-lactate-co-glycolate) (50:50), average value for n * 8; j * k ⁇ ⁇
  • the content of the oligomers, co-oligomers, polymers and / or copolymers in the cosmetic or pharmaceutical preparations is advantageously 0.01-20% by weight, preferably 0.5-5% by weight, particularly preferably 1 , 5 - 2.5 wt .-%, each based on the total weight of the cosmetic or pharmaceutical preparations.
  • the oligomer or co-oligomers, polymers and / or copolymers in dissolved form into cosmetic formulations.
  • the person skilled in the art can make a non-inventive selection from a large number of known solvents which are generally known for the given substance class. It was surprising, however, that partially or completely esterified polybasic carboxylic acids would prove to be particularly advantageous solvents for the oligomers, co-oligomers, polymers and / or co-polymers according to the invention.
  • AOOC-X-COOB where X is selected from the group consisting of up to four carboxylic acid groups and up to four carboxylic acid alkyl ester groups -COOD, -COOE, -COOF and up to four hydroxyl groups, branched and or unbranched alkylene groups with up to six C. -Atoms and the group of the types substituted with up to four carboxylic acid groups and up to four carboxylic acid alkyl ester groups -COOD, -COOE, -COOF and up to four hydroxyl groups
  • A, B, D, E and F represent branched or unbranched alkyl groups with up to five carbon atoms.
  • esters are triethyl citrate
  • esters are not only good solvents for the oligomers, polymers, co-oligomers and / or copolymers according to the invention, but also stabilize them against depolymerization or deoligomerization.
  • esters preferably the citric acid esters, act synergistically with the oligomers, polymers according to the invention in relation to the cosmetic or dermatological action of the ⁇ -hydroxycarboxylic acids, in particular in relation to the caring effect, especially in relation to the action against skin aging.
  • these esters act synergistically with the oligomers, polymers according to the invention in relation to the cosmetic or dermatological action of the ⁇ -hydroxycarboxylic acids, in particular in relation to the caring effect, especially in relation to the action against skin aging.
  • Co-oligomers and / or copolymers together.
  • the weight ratio of the oligomers, polymers, co-oligomers and / or copolymers on the one hand to the above-described stabilizing esters on the other hand is advantageously in the range from about 1:10 to 10: 1, preferably about 1: 4 to 2 : 1, particularly preferably about 3: 7.
  • DE-GbM 88 04 423 It is known, for example from DE-GbM 88 04 423, to use corresponding citric acid esters as plasticizers for polyiactides / glycolides and similar polymers.
  • the cosmetic or pharmaceutical use according to the invention was neither suggested nor anticipated by DE-GbM 88 04 423, which relates to surgical materials.
  • DE-GbM 88 04 423 recommends acetone as the solvent, which is neither cosmetically nor pharmaceutically acceptable.
  • silicone oils such as dimethicone as solvents for the oligomers, polymers, co-oligomers and / or copolymers according to the invention.
  • the oligomers, polymers, co-oligomers or copolymers according to the invention are remarkably stable in cosmetic and pharmaceutical preparations and largely decompose only on human skin to form the underlying oligomers, which then become available to the skin with all its advantageous properties. It is also possible and possibly advantageous to use suspensions of the oligomers, polymers, co-oligomers and / or co-polymers according to the invention.
  • micronization Before the solution or suspension process, it can be advantageous to precede a micronization process, it being preferred to prefer the micronization with cooling, for example at temperatures below -78 ° C., in particular at temperatures below -150 ° C. at approx. -190 ° C.
  • the dissolving process is preferably carried out by means of strong agitation, for example in an ultra-turrax. It can also be advantageous to add a wetting agent or an antistatic agent during the solution or suspension process.
  • Preparations according to the invention are produced in accordance with the usual rules familiar to those skilled in the art.
  • the preparations according to the invention are advantageously in the form of emulsions, preferably O / W emulsions.
  • emulsions preferably O / W emulsions.
  • W / O emulsions hydrodispersions, gels, oils, multiple emulsions, for example in the form of W / O / W or OW / O emulsions, anhydrous ointments or ointment bases etc.
  • finely dispersed droplets of the second phase water droplets in W / O or lipid vesicles in O / W emulsions
  • finely dispersed droplets of the first phase are emulsified in such droplets.
  • These droplets can also have finer disperse droplets (third degree multiple emulsion) and so on.
  • W / O or O / W emulsions water-in-oil or oil-in-water
  • W / O / W water-in-oil or oil-in-water
  • the second degree multiple emulsions are sometimes referred to as "bimultiple systems", such third degrees as “trimultiple systems” etc. (W.Seifriz, Studies in Emulsions, J.Phys.Chem., 29 (1925) 738-749).
  • Processes for producing multiple emulsions are known per se to the person skilled in the art. There are two-pot processes in which a simple emulsion (e.g. a W / O emulsion) is introduced and, by adding another phase (e.g. a water phase) with a corresponding emulsifier (e.g. an O / W emulsifier) into a multiple emulsion (e.g. a W / O / W emulsion) is transferred.
  • a simple emulsion e.g. a W / O emulsion
  • another phase e.g. a water phase
  • a corresponding emulsifier e.g. an O / W emulsifier
  • a multiple emulsion e.g. a W / O / W emulsion
  • a second method consists in converting emulsifier mixtures with an oil phase and a water phase into a multiple W / O / W emulsion in a one-pot process.
  • the emulsifiers are dissolved in the oil phase and combined with the water phase.
  • Hydrodispersions are dispersions of a liquid, semi-solid or solid inner (discontinuous) lipid phase in an outer aqueous (continuous) phase.
  • hydrodispersions are essentially free of emulsifiers. Like other emulsions, hydro dispersions represent metastable systems and are inclined to change into a state of two discrete phases that are coherent. In emulsions, the choice of a suitable emulsifier prevents phase separation.
  • the stability of such a system can be ensured, for example, by building a gel structure in the aqueous phase in which the lipid droplets are stably suspended.
  • Such preparations have proven to be extremely advantageous and particularly stable.
  • Advantageous thickeners for this purpose are carbopols, polysaccharide-based thickeners and bentonites.
  • Particularly advantageous preparations are also obtained if the active compounds according to the invention are combined with antioxidants and / or other substances which counteract cell aging.
  • the preparations advantageously contain one or more antioxidants. All of the antioxidants suitable or customary for cosmetic and / or dermatological applications are used as inexpensive, but nevertheless optional anti-oxidants.
  • Amino acids e.g. glycine, histidine, tyrosine, tryptophan
  • imidazoles e.g. urocanic acid
  • peptides such as D, L-carnosine, D-carnosine, L-camosine and their derivatives (e.g. anserine)
  • carotenoids e.g. ⁇ -carotene, ß-carotene, lycopene
  • lipoic acid and their derivatives e.g. dihydroliponic acid
  • aurothioglucose propylthiouracil and other thiols
  • 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, dilaurylthiodipropionate, distearylthiodipropionate, thiodipropionic acid and their derivatives (esters, Ethers, peptides, lipids, nucleotides, nucleosides and salts) and sulfoximine compounds (e.g.
  • buthionine sulfoximines homocysteine sulfoximine, buthionine sulfones, penta-, hexa-, heptahionine sulfoximine) in very low tolerable dosages (e.g. pmol to ⁇ mol / kg), also (metal) -Chela gates (e.g. ⁇ -hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), humic acid, bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives (e.g.
  • the amount of the antioxidants (one or more compounds) in the preparations is preferably 0.001 to 30% by weight, particularly preferably 0.05-20% by weight, in particular 1-10% by weight, based on the total weight of the preparation.
  • vitamin E and / or its derivatives represent the antioxidant (s)
  • vitamin A or vitamin A derivatives or carotenes or their derivatives represent the antioxidant or antioxidants, it is advantageous to use their respective concentrations in the range from 0.001-10% by weight, based on the total weight of the formulation, to choose.
  • Cttronic acid, salicylic acid, other ⁇ -hydroxycarboxylic acids, biotin and the like can advantageously be used as other substances which counteract cell aging.
  • the cosmetic preparations according to the invention can contain cosmetic auxiliaries as are usually used in such preparations, e.g. Preservatives, bactericides, deodorizing substances, irritant substances, antiperspirants, insect repellents, vitamins, anti-foaming agents, dyes, pigments with a coloring effect, thickeners, softening substances, moisturizing and / or moisturizing substances, fats, Oils, waxes or other common components of a cosmetic formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.
  • cosmetic auxiliaries e.g. Preservatives, bactericides, deodorizing substances, irritant substances, antiperspirants, insect repellents, vitamins, anti-foaming agents, dyes, pigments with a coloring effect, thickeners, softening substances, moisturizing and / or moisturizing substances, fats, Oils, waxes or other common components of a cosmetic formulation such as alcohols,
  • the preparations according to the invention can also advantageously contain substances which absorb UV radiation in the UVB range, the total amount of the filter substances being, for example, 0.1% by weight to 30% by weight, preferably 0.5 to 10% by weight. %, in particular 1 to 6% by weight, based on the total weight of the preparation, in order to provide cosmetic preparations which protect the skin from the entire range of ultraviolet radiation, and in which the stinging of the ⁇ -hydroxycarboxylic acids or ⁇ -keto carboxylic acids are prevented or drastically reduced.
  • the pH of the preparations according to the invention can advantageously be set in the acidic range, the pH range from 3.5 to 7 being preferred, particularly preferably from 4 to 6, very particularly about 5.5.
  • the stability of the oligomers, polymers, co-oligomers and / or copolymers according to the invention is additionally increased by buffering.
  • Preparations according to the invention can also advantageously serve as sunscreens.
  • Emulsions according to the invention e.g. in the form of a sun protection cream or sun protection milk are advantageous and contain e.g. the fats, oils, waxes and other fat bodies mentioned, as well as water and an emulsifier, as is usually used for such a type of formulation.
  • Oils such as triglycerides of capric or caprylic acid, but preferably castor oil; Fats, waxes and other natural and synthetic fat bodies, preferably esters of fatty acids with alcohols of low C number, e.g. with isopropanol, propylene glycol or glycerin, or esters of fatty alcohols with low C number alkanoic acids or with fatty acids; Alkyl benzoates;
  • Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiloxanes and mixed forms thereof.
  • Alcohols, diols or polyols of low 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 analogous products, furthermore alcohols with a low C number, for example ethanol, isopropanol, 1, 2-propanediol, glycerol and in particular one or more thickeners, which one or more can advantageously be selected from the group consisting of silicon dioxide, aluminum silicates, polysaccharides or their derivatives, for example hyaluronic acid, xanthan gum, hydroxypropyl methyl cellulose, particularly advantageously from the group of polyacrylates, are preferred a polyacrylate from the group of the so-called carbopoles, for example carbopoles of types
  • the cosmetic or dermatological sunscreen preparations advantageously contain inorganic pigments, in particular micropigments, e.g. in amounts of 0.1% by weight to 30% by weight, preferably in amounts of 0.5% by weight to 10% by weight, but in particular 1% by weight to 6% by weight on the total weight of the preparations.
  • the light protection formulations according to the invention can advantageously contain substances which absorb UV radiation in the UVB range, the total amount of the filter substances e.g. 0.1% by weight to 30% by weight, preferably 0.5 to 10% by weight, in particular 1 to 6% by weight, based on the total weight of the preparations, in order to provide cosmetic preparations places that protect the skin from the entire range of ultraviolet radiation. They can also serve as sunscreens.
  • the UVB filters can be oil-soluble or water-soluble.
  • Advantageous oil-soluble UVB filter substances include:
  • 3-benzylidene camphor derivatives preferably 3- (4-methylbenzylidene) camphor, 3-benzylidene camphor;
  • 4-aminobenzoic acid derivatives preferably 4- (dimethylamino) benzoic acid (2-ethylhexyl ester, 4- (dimethylamino) benzoic acid amyl ester;
  • esters of cinnamic acid preferably 4-methoxycinnamic acid (2-ethylhexyl) ester, 4-methoxycinnamic acid isopentyl ester;
  • benzophenone preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone;
  • Esters of benzalmalonic acid preferably 4-methoxybenzalmalonic acid di (2-ethylhexyl) ester;
  • Advantageous water-soluble UVB filter substances include: - Salts of 2-phenylbenzimidazole-5-sulfonic acid such as its sodium, potassium or triethanammonium salt, and the sulfonic acid itself;
  • 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 which have hitherto usually been 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-phenyI- 3- (4'-isopropylphenyl) propane-1,3-dione.
  • These combinations or preparations containing these combinations are also the subject of the invention.
  • the quantities used for the UVB combination can be used.
  • the total amount of UVA filter substances can advantageously be 0.1% by weight to 30% by weight, preferably 0.5 to 10% by weight, in particular 1 to 6% by weight, based on the total weight of the preparation, in order to provide cosmetic preparations which protect the skin from the entire range of ultraviolet radiation and in which the stinging of the ⁇ -hydroxycarboxylic acids or ⁇ -ketocarboxylic acids is prevented or drastically reduced.
  • Cosmetic and dermatological preparations which are in the form of a sunscreen, a pre-soleil or apres-soleil product are also advantageous. These advantageously also contain at least one UVA filter and / or at least one UVB filter.
  • cosmetic and dermatological preparations which are in the form of a sunscreen, a pre-soleil or apres-soleil product are also particularly advantageous. product and in addition to the UVA filter (s) and / or the UVB filter (s)
  • Filters contain one or more antioxidants.
  • Cosmetic and dermatological preparations according to the invention preferably 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 T ⁇ O2), zinc (ZnO), iron (eg F ⁇ 2 ⁇ 3), zirconium (Zr ⁇ 2), Silicon (Si ⁇ 2), manganese (e.g. MnO), aluminum (AI2O3), cerium (e.g. C ⁇ 2 ⁇ 3), mixed oxides of the corresponding metals and mixtures of such oxides. It is particularly preferred to use pigments based on TiO 2
  • a prerequisite for the use of inorganic pigments for the purposes of the invention is, of course, the cosmetic or dermatological harmlessness of the underlying substances.
  • the particle diameter of the pigments used is advantageous to choose the particle diameter of the pigments used to be less than 100 nm.
  • the inorganic pigments are in hydrophobic form, that is to say that they have been surface-treated to be water-repellent.
  • This surface treatment can consist in that the pigments are provided with a thin hydrophobic layer by methods known per se.
  • One such method consists, for example, in that the hydrophobic surface layer according to a reaction
  • n and m are stoichiometric parameters to be used at will, R and R 'are the desired organic radicals.
  • hydrophobized pigments shown in analogy to DE-OS 33 14 742 are advantageous.
  • Advantageous TiO 2 pigments are available, for example, under the trade names T 805 (DEGUSSA) or M 262 (KEMIRA) or M 160 (KEMIRA) or MT 100 T (TAYCA).
  • Advantageous SiO 2 pigments can be selected from the range of hydrophobic pigments sold under the trade names AEROSIL (DEGUSSA), for example AEROSIL R 812 or AEROSIL R 972.
  • Preparations according to the invention are advantageously characterized by a content of 0.1 to 10% by weight, in particular 0.5 to 5.0% by weight, of hydrophobic inorganic pigments, in each case based on the total weight of the composition.
  • Cetyl stearyl isononanoate PEG-20 cetyl stearyl ether, cetyl stearyl alcohol, glyceryl stearate, glycerol, cetyl palmitate, PEG-12 cetyl stearyl ether, benzoic acid 15.00
  • Cetyl stearyl isononanoate PEG-20 cetyl stearyl ether, cetyl stearyl alcohol, glyceryl stearate, glycerol, cetyl palmitate, PEG-12 cetyl stearyl ether, benzoic acid 15.00
  • Resomer 104 (30% by weight) in triethyl citrate 6.60
  • Resomer 104 (30% by weight in triethyl citrate) 6.60
  • Resomer 104 (30% by weight in tributyl citrate) 6.60

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Abstract

Les compositions cosmétiques ou dermatologiques décrites, qui contiennent une quantité efficace d'un ou plusieurs oligomères, et/ou polymères, et/ou co-oligomères et/ou copolymères en solution ou en suspension d'un ou plusieurs acides α-hydroxycarboxyliques de formule générale (I) réticulés les uns aux autres selon le schéma (II), permettent l'administration de ces acides α-hydroxycarboxyliques monomères dans des compositions cosmétiques ou dermatologiques.
PCT/EP1996/002354 1995-06-02 1996-05-31 COMPOSITIONS COSMETIQUES OU DERMATOLOGIQUES CONTENANT DES OLIGOMERES OU DES POLYMERES D'ACIDES α-HYDROXYCARBOXYLIQUES WO1996038125A1 (fr)

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DE1995120237 DE19520237A1 (de) 1995-06-02 1995-06-02 Kosmetische oder dermatologische Zubereitungen, enthaltend Oligomere oder Polymere von alpha-Hydroxycarbonsäuren

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Cited By (2)

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EP0831767A4 (fr) * 1995-06-07 2000-05-17 Yu Ruey J Esters d'alpha hydroxyacide utilises pour traiter le vieillissement de la peau
EP0835651A3 (fr) * 1996-10-11 2005-04-13 L'oreal Emulsion cosmétique H/E à forte teneur en électrolytes

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DE19711244A1 (de) * 1997-03-18 1998-10-08 Beiersdorf Ag Lichtschutzzubereitungen mit einem Gehalt an Partialglyceriden der Bernsteinsäure und wasserlöslichen UV-Filtersubstanzen
DE19713776A1 (de) * 1997-04-03 1998-10-08 Beiersdorf Ag Lichtschutzzubereitungen mit einem Gehalt an basischen Aminosäuren und wasserlöslichen UV-Filtersubstanzen
DE19714765A1 (de) * 1997-04-10 1998-10-15 Merck Patent Gmbh Verwendung von niedermolekularen, oligomeren Estern von alpha-Hydroxysäuren und/oder aromatischen o-Hydroxysäuren in kosmetischen Formulierungen
PT1216021E (pt) * 1999-09-15 2005-07-29 Bayer Consumer Care Ag Composicoes farmaceuticas e/ou cosmeticas
DE60030996T2 (de) * 1999-09-30 2007-03-01 L'oreal Kosmetische zusammensetzungen mit aluminiumoxid enthaltenden nanopartikeln
US20070027105A1 (en) 2005-07-26 2007-02-01 Alza Corporation Peroxide removal from drug delivery vehicle
AU2007325918B2 (en) 2006-11-03 2013-10-17 Durect Corporation Transdermal delivery systems comprising bupivacaine
JP2023515918A (ja) 2020-01-13 2023-04-17 デュレクト コーポレーション 不純物が低減された徐放性薬物送達システム及び関連の方法

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EP0413528A1 (fr) * 1989-08-15 1991-02-20 Ruey J. Dr. Yu Compositions amphotériques et formes polymériques des alpha-hydroxy-acides, et leur application thérapeutique
EP0447318A1 (fr) * 1990-03-16 1991-09-18 L'oreal Composition pour le traitement cosmétique et/ou pharmaceutique des couches supérieures de l'épiderme par application topique sur la peau et procédé de préparation correspondant
EP0514067A1 (fr) * 1991-05-07 1992-11-19 Unilever Plc Composition cosmétique

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EP0637450A3 (fr) * 1993-08-04 1995-04-05 Collagen Corp Méthode et composition pour revigorer le tissu cicatriciel.

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US4363815A (en) * 1975-07-23 1982-12-14 Yu Ruey J Alpha hydroxyacids, alpha ketoacids and their use in treating skin conditions
EP0413528A1 (fr) * 1989-08-15 1991-02-20 Ruey J. Dr. Yu Compositions amphotériques et formes polymériques des alpha-hydroxy-acides, et leur application thérapeutique
EP0447318A1 (fr) * 1990-03-16 1991-09-18 L'oreal Composition pour le traitement cosmétique et/ou pharmaceutique des couches supérieures de l'épiderme par application topique sur la peau et procédé de préparation correspondant
EP0514067A1 (fr) * 1991-05-07 1992-11-19 Unilever Plc Composition cosmétique

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0831767A4 (fr) * 1995-06-07 2000-05-17 Yu Ruey J Esters d'alpha hydroxyacide utilises pour traiter le vieillissement de la peau
EP0835651A3 (fr) * 1996-10-11 2005-04-13 L'oreal Emulsion cosmétique H/E à forte teneur en électrolytes

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