EP1401389A2 - Utilisation de carnitine et/ou d'une ou de plusieurs acyl-carnitines pour realiser des preparations cosmetiques ou dermatologiques destinees a accroitre la biosynthese de ceramide - Google Patents

Utilisation de carnitine et/ou d'une ou de plusieurs acyl-carnitines pour realiser des preparations cosmetiques ou dermatologiques destinees a accroitre la biosynthese de ceramide

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Publication number
EP1401389A2
EP1401389A2 EP02747354A EP02747354A EP1401389A2 EP 1401389 A2 EP1401389 A2 EP 1401389A2 EP 02747354 A EP02747354 A EP 02747354A EP 02747354 A EP02747354 A EP 02747354A EP 1401389 A2 EP1401389 A2 EP 1401389A2
Authority
EP
European Patent Office
Prior art keywords
polyethylene glycol
skin
acid
ether
preparations
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
EP02747354A
Other languages
German (de)
English (en)
Inventor
Thomas Blatt
Thomas Döring
Claudia Mundt
Christopher Mummert
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
Priority to EP15185392.6A priority Critical patent/EP3009127A1/fr
Priority to EP15002815.7A priority patent/EP3009124A1/fr
Publication of EP1401389A2 publication Critical patent/EP1401389A2/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
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/007—Preparations for dry skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • 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
    • A61K8/34—Alcohols
    • 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
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • 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
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/70—Biological properties of the composition as a whole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments

Definitions

  • the present invention relates to cosmetic or dermatological dermatological preparations containing active ingredients for the care and protection of the skin, in particular sensitive skin, and very particularly in the foreground of skin aged or aging due to intrinsic and / or extrinsic factors, and the use thereof Active ingredients and combinations of such active ingredients in the field of cosmetic and dermatological skin care.
  • Cosmetic skin care is understood primarily to mean that the natural function of the skin as a barrier against environmental influences (eg dirt, chemicals, microorganisms) and against the loss of the body's own substances (eg water, natural fats, electrolytes) is strengthened or restored ,
  • the barrier effect of the skin can be quantified by determining the transepidermal water loss (TEWL - transepidermal water loss). This is the evaporation of water from the inside of the body without taking into account the loss of water when sweating.
  • the determination of the TEWL value has proven to be extremely informative and can be used to diagnose cracked or chapped skin, to determine the compatibility of chemically differently structured surfactants and the like.
  • the water content in the top layer of skin is of the utmost importance. It can be influenced to a limited extent by introducing moisture regulators.
  • Anionic surfactants which are generally components of cleaning preparations, can increase the pH value in the horny layer for a long time, which greatly hinders regenerative processes that serve to restore and renew the barrier function of the skin. In this case, a new, often very unfavorable state of equilibrium occurs in the horny layer between regeneration and the loss of essential substances through regular extraction, which significantly affects the external appearance of the skin and the physiological functioning of the horny layer.
  • the lipid composition and amount of the horny layer of the pathologically altered, dry and dry, but not diseased skin of younger and older people deviate from the normal condition found in healthy, normally hydrated skin of an equal age group.
  • the changes in the lipid pattern of the very dry, non-eczematous skin of patients with atopic eczema represent an extreme case for the deviations that are found in the dry skin of healthy people.
  • Adverse changes in the lipid membranes of the type described above may be due to incorrectly controlled lipid biosynthesis and also ultimately increase the transepidermal water loss.
  • a long-lasting barrier weakness in turn makes the healthy skin more sensitive and in individual cases can contribute to the development of eczematous processes in the diseased skin.
  • the effect of ointments and creams on the barrier function and hydration of the horny layer usually does not consist in restoring or strengthening the physicochemical properties of the lamellae made of intercellular lipids.
  • a major partial effect is due to the mere covering of the treated skin areas and the resulting water retention in the underlying horny layer.
  • Co-applied hygroscopic Substances bind the water so that there is a measurable increase in the water content in the horny layer.
  • this purely physical barrier can be removed relatively easily.
  • the skin care effect can diminish with regular treatment, so that the status quo is finally reached again even during treatment.
  • the condition of the skin may temporarily deteriorate after discontinuation.
  • a sustainable product effect is usually not achieved or only to a limited extent.
  • the aim of the present invention was therefore to find ways to avoid the disadvantages of the prior art.
  • the effects of skin care products should be physiological, quick and sustainable.
  • Skin care in the sense of the present invention is to be understood primarily as meaning that the natural function of the skin acts as a barrier against environmental influences (e.g. dirt, chemicals, microorganisms) and against the loss of the body's own substances (e.g. water, lipids) , Electrolytes) is strengthened or restored.
  • environmental influences e.g. dirt, chemicals, microorganisms
  • the loss of the body's own substances e.g. water, lipids
  • Electrolytes e.g. water, lipids
  • the effect of ointments and creams on the barrier function and the hydration of the horny layer is based essentially on the covering (occlusion) of the treated skin areas.
  • the ointment or cream is, so to speak, a (second) artificial barrier that is supposed to prevent water loss from the skin.
  • This physical barrier can be easily for example with cleaning agents - are removed again, whereby the original, impaired state is reached again.
  • the skin care effect can decrease with regular treatment. After stopping the application of the product, the skin quickly returns to the condition before the start of treatment. With certain products, the condition of the skin may even temporarily deteriorate.
  • a sustainable product effect is usually not achieved or only to a limited extent.
  • the effect of nourishing cleaning products essentially consists in an efficient regreasing with sebum lipid-like substances.
  • the damage to the horny layer barrier can be further limited.
  • the prior art lacks preparations which have a positive effect on the barrier function and hydration of the horny layer and which strengthen or even restore the physicochemical properties of the horny layer and in particular the lamellae made of intercellular lipids.
  • the object of the present invention was therefore to eliminate the disadvantages of the prior art.
  • skin-care preparations and preparations for cleaning the skin should be made available which maintain or restore the barrier properties of the skin, especially when the natural regeneration of the skin is insufficient. They should also be suitable for the treatment and prophylaxis of consequential damage to skin drying out, for example fissures or inflammatory or allergic processes or also neurodermatitis.
  • camitin and / or one or more acyl-camitines for the production of cosmetic or dermatological preparations for the production of cosmetic or dermatological preparations for increasing ceramide biosynthesis, for improving the barrier properties of the skin and for Prevention or reduction of skin dehydration.
  • acylated and non-acylated camitin in cosmetic or dermatological preparations is known per se.
  • FR-OS 2 654 618 describes the use of L-carnitine derivatives in cosmetic preparations for regulating cell growth.
  • US Pat. No. 4,839,159 describes topical preparations for improving or preventing harmful skin conditions, including wrinkling, which is due to a loss of skin elasticity.
  • L-Carnitine [3-hydroxy-4- (trimethylammonio) butyric acid betaine] has the structural formula
  • the L-form of camitin is widespread in animal tissues, especially the striped muscles. In fatty acid metabolism, it serves as a carrier for acyl groups through the mitochondrial membrane. These are transferred from acyl-coenzyme A to the hydroxyl group of L-camitine by an acyl transferase. L-carnitine and acyl-L-camitine are transported through the membrane by means of a transport protein (Translocase). Both entantiomers (D- and L-form) can be used advantageously for the purposes of the present invention. It can also be advantageous to use any mixture of enantiomers, for example a racemate of D and L form.
  • acylcarnitines are selected from the group of substances of the following general structural formula
  • R is selected from the group of branched and unbranched alkyl radicals with up to 10 carbon atoms.
  • Propionylcamitine and, very particularly preferably, acetylcarnitine are preferred.
  • Both entantiomers (D- and L-form) can be used advantageously for the purposes of the present invention. It can also be advantageous here to use any enantiomeric mixture, for example a racemate of D and L form.
  • the preparations according to the invention advantageously contain 0.001-10% by weight of camitin and / or one or more acylcarnitines, based on the total weight of the preparations.
  • preparations containing the active compound combinations according to the invention, customary antioxidants can be used.
  • the antioxidants are advantageously selected from the group consisting of amino acids (r as glycine, histidine, tyrosine, tryptophan) and derivatives thereof, imidazoles (for example Urocaninkla- re) and their derivatives, peptides such as D, L-carnosine, D-carnosine, L- Carnosine and its de- derivatives (e.g. anserine), carotenoids, carotenes (e.g. ⁇ -carotene, ⁇ -carotene, lycopene) and their derivatives, lipoic acid and their derivatives (e.g.
  • amino acids r as glycine, histidine, tyrosine, tryptophan
  • imidazoles for example Urocaninkla- re
  • peptides such as D, L-carnosine, D-carnosine, L- Carnosine and its de- derivatives (e.g. anserine)
  • carotenoids e.g.
  • thiols e.g. thioredoxin, glutathione, cysteine, Cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, ⁇ -linoleyl, cholesteryl and glyceryl esters
  • Dilaurylthiodipropionat Distearylthiodipropionat
  • Thiodipropionic acid and their derivatives esters, ethers, peptides, lipids, nucleotides, nucleosides and salts
  • sulfoximine compounds eg Buthioninsulfoximine, Homocysteinsulfoximin, Buthioninsulfone, Penta-, Hexa-, Hept
  • ⁇ -hydroxy fatty acids e.g. citric acid, lactic acid, malic acid
  • humic acid e.g. citric acid, lactic acid, malic acid
  • humic acid e.g. citric acid, lactic acid, malic acid
  • humic acid e.g. citric acid, lactic acid, malic acid
  • humic acid e.g. citric acid, lactic acid, malic acid
  • humic acid e.g. citric acid, lactic acid, malic acid
  • humic acid e.g. citric acid, lactic acid, malic acid
  • humic acid e.g. citric acid, lactic acid, malic acid
  • humic acid e.g. citric acid, lactic acid, malic acid
  • humic acid e.g. citric acid, lactic acid, malic acid
  • humic acid e.g. citric acid, lactic acid, malic acid
  • humic acid 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 to 20% by weight, in particular 1 to 10% by weight, based on the total weight of the preparation ,
  • the prophylaxis or the cosmetic or dermatological treatment with the active ingredient used according to the invention or with the cosmetic or topical dermatological preparations with an effective content of active ingredient used according to the invention is carried out in the usual way, namely in such a way that the active ingredient used according to the invention or the cosmetic or topical dermatological preparations with an effective content of inventive 'ß active ingredient used on the affected skin is applied.
  • the active ingredient used according to the invention can advantageously be incorporated into customary cosmetic and dermatological preparations, which can be in various forms.
  • they can be a solution, an emulsion of the type water-in-oil (W / O) or of the type oil-in-water (O / W), or a multiple emulsions, for example of the type water-in-oil-in -Water (W / O / W) or oil-in-water-in-oil (O / W / O), a hydrodispersion or lipodispersion, a gel, a solid stick or an aerosol.
  • W / O type water-in-oil
  • O / W oil-in-water-in-oil
  • hydrodispersion or lipodispersion for example of the type water-in-oil-in -Water (W / O / W) or oil-in-water-in-oil (O / W / O), a hydrodispersion or lipodispersion, a gel, a solid stick or an aerosol.
  • Emulsions according to the invention in the sense of the present invention are advantageous and contain e.g. Fats, oils, waxes and / or other fat bodies, as well as water and one or more emulsifiers, as are usually used for such a type of formulation.
  • the cosmetic preparations according to the invention can therefore contain cosmetic auxiliaries as are usually used in such preparations, e.g. Preservatives, bactericides, deodorizing substances, antiperspirants, insect repellents, vitamins, anti-foaming agents, dyes, pigments with a coloring effect, thickening agents, softening substances, moisturizing and / or moisturizing substances, fats, oils, waxes or other usual components a cosmetic formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.
  • cosmetic auxiliaries as are usually used in such preparations, e.g. Preservatives, bactericides, deodorizing substances, antiperspirants, insect repellents, vitamins, anti-foaming agents, dyes, pigments with a coloring effect, thickening agents, softening substances, moisturizing and / or moisturizing substances, fats, oils, waxes or other usual components a cosmetic formulation such as alcohols, polyo
  • Medical topical compositions in the sense of the present invention generally contain one or more drugs in effective concentration.
  • cosmetic and medical Application refer to the legal provisions of the Federal Republic of Germany (e.g. cosmetics regulation, food and drug law).
  • Preparations according to the invention can also advantageously contain substances which absorb UV radiation in the UVB range, the total amount of filter substances e.g. 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 produce cosmetic preparations To provide that protect the hair or skin from the entire range of ultraviolet radiation. They can also serve as a sunscreen for the hair.
  • UVB filter substances if they 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:
  • 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,
  • 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,
  • Salts of 2-phenylbenzimidazole-5-sulfonic acid such as its sodium, potassium or triethanolammonium salt, and also the sulfonic acid itself;
  • Sulfonic acid derivatives of benzophenones preferably 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and its salts
  • Sulfonic acid derivatives of 3-benzylidene camphor such as 4- (2-oxo-3-bomylidene-methyl) benzenesulfonic acid, 2-methyl-5- (2-oxo-3-bornylidene methyl) sulfonic acid and its salts and 1,4- di (2-oxo-10-sulfo-3-bornylidenemethyl) benzene and its salts (the corresponding 10-sulfato compounds, e.g. the corresponding sodium, potassium or triethanolammonium salt), also as benzene-1,4,4 called di (2-oxo-3-bornylidenemethyl-10-sulfonic acid
  • 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.
  • the quantities used for the UVB combination can be used.
  • Cosmetic and dermatological preparations according to the invention advantageously also 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 (for example MnO), aluminum (Al 2 O 3 ), cerium (for example 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 in hydrophobic form, i.e. that they have been treated to be water-repellent on the surface.
  • 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 after a rectification n TiO 2 + m (RO) 3 Si-R '-> n TiO 2 (surface)
  • 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 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 of type and charge of the hydrophilic part of the molecule. There are four groups:
  • Anionic surfactants generally have carboxylate, sulfate or sulfonate groups as functional groups. In an 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 accordingly behave like anionic or cationic surfactants in aqueous solution depending on the pH. in the strongly acidic environment they have a positive charge and in an alkaline environment a negative charge. In the neutral pH range, however, they are zwitterionic, as the following example should illustrate:
  • B + any cation, eg Na +
  • Non-ionic surfactants do not form ions in an aqueous medium.
  • 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 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 dilaureth-4-phosphate, Sulfonic acids and salts such as
  • acyl isethionates e.g. Sodium / ammonium cocoyl isethionate
  • alkyl sulfonates for example sodium coconut monoglyceride sulfate, sodium C 12-14 olefin sulfonate, 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
  • sulfuric acid esters such as
  • alkyl ether sulfate for example sodium, ammonium, magnesium, MIPA, TIPA laureth sulfate, sodium myreth sulfate and sodium C 12-13 pareth sulfate,
  • Alkyl sulfates for example sodium, ammonium and TEA lauryl sulfate.
  • Quaternary surfactants contain at least one N atom which 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 be also preferably selected from the group of quaternary ammonium compounds, in particular benzene zyltrialkylammoniumchloride or bromides, such as Benzyldimethylstea- rylammoniumchlorid, also alkyltrialkylammonium, such as for example Ce tyltrimethylammoniumchlorid or bromide, alkyldimethylhydroxyethylammonium chlorides or bromides, dialkyldimethylammonium chlorides or bromides, alkylamidethyltrimethylammonium 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 salt
  • acyl / dialkyl ethylenediamine for example sodium acyl amphoacetate, disodium acyl amphodipropionate, disodium alkyl amphodiacetate, sodium acylamphohydroxypropyl sulfonate, disodium acylamphodiacetate and sodium acylamphopropionate,
  • N-alkylamino acids for example aminopropylalkylglutamide, alkylaminopropionic acid, sodium alkylimidodipropionate and lauroamphocarboxyglycinate.
  • alkanolamides such as Cocamide MEA / DEA / MIPA
  • amine oxides such as cocoamidopropylamine oxide
  • esters which are formed by esterification of 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 propoxyliert.es lanolin, ethoxylated / propoxylated polysiloxanes, propoxylated POE ethers and alkylpolyglycosyl 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 95% by weight, based on the total weight of the preparations.
  • the lipid phase of the cosmetic or dermatological emulsions 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, for example
  • Fats, waxes and other natural and synthetic fat bodies preferably
  • Esters of fatty acids with low C alcohols e.g. with isopropanol, propylene glycol or glycerin, or esters of fatty alcohols with low C number alkanoic acids or with fatty acids;
  • Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiloxanes and
  • the oil phase of the emulsions 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-ethylhexyl stylate, 2-ethylhexyl palylate, Octyldodecyl palmitate, oleyl oleate, olerlerucate, erucyl oleate, erucylerucate as well as synthetic, semi-synthetic and natural mixtures of such esters, for example Jojoba oil.
  • the oil phase can advantageously be chosen 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, for example olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palm oil, coconut oil, palm kernel oil and the like. Any mixtures of such oil and wax components can also be used advantageously for the purposes of the present invention. It may also be advantageous to use waxes, for example cetyl palmitate, as the sole lipid component of the oil phase.
  • synthetic, semisynthetic and natural oils for example olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palm oil, coconut oil, palm kernel oil and the like. Any mixtures of such oil and wax components can also be used advantageously for the purposes of the present invention. It may also be advantageous to use waxes, for example cetyl palmitate, as the sole lipid component of the oil phase.
  • the oil phase is advantageously selected from the group consisting of 2-ethylhexyl isostearate, octyldodecanol, isotridecyl isononanoate, isoeicosane, 2-ethylhexyl cocoate, C 12 . 15 alkyl benzoate, caprylic capric acid triglyceride, dicaprylyl ether.
  • hydrocarbons paraffin oil, squalane and squalene can be used advantageously for the purposes of the present invention.
  • the oil phase can advantageously also have a content of cyclic or linear silicone oils or consist entirely of such oils, although it is preferred to use an additional content of other oil phase components in addition to the silicone oil or the silicone oils.
  • Such silicones or silicone oils can be present as monomers, which 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 represented here generally by the radicals R 1 - R 4 (want to say that the number of different residues is not necessarily limited to up to 4), m can assume values from 2 to 200,000.
  • 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)
  • the aqueous phase of the preparations according to the invention advantageously advantageously contains alcohols, diols or polyols of low C number, and also their ethers, preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether , Diethylene glycol monomethyl or monoethyl ether and similar products, furthermore alcohols of low carbon number, for example ethanol, isopropanol, 1, 2-propanediol, glycerol and in particular one or more thickeners, which can advantageously be selected from the group consisting of silicon dioxide, aluminum silicates.
  • Preparations according to the invention which are present as emulsions particularly advantageously contain one or more hydrocolloids.
  • hydrocolloids can advantageously be selected from the group of the gums, polysaccharides, cellulose derivatives, phyllosilicates, 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. Hydroxypropyl guar (Jaguar® HP 8).
  • polysaccharides and derivatives are e.g. Hyaluronic acid, chitin and chitosan, chondroitin sulfates, starch and starch derivatives.
  • the cellulose derivatives include, for example, 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.
  • silica gels can also advantageously be used.
  • the polyacrylates include e.g. Carbopol types from Goodrich (Carbopol 980, 981, 1382, 5984, 2984, EDT 2001 or Pemulen 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 fatty acid esters and fatty acid esters of polyhydric alcohols and their ethoxylated derivatives (e.g. glyceryl monostearates, sorbitan stearates, glyceryl stearyl citrates, sucrose stearates) b) ethoxylated fatty alcohols and fatty acids c) ethoxylated fatty amides, fatty acid glycol amides, fatty acid glycol amides, fatty acid glycol amides, e.g. Triton X)
  • polyhydric alcohols and their ethoxylated derivatives e.g. glyceryl monostearates, sorbitan stearates, glyceryl stearyl citrates, sucrose stearates
  • ethoxylated fatty alcohols and fatty acids ethoxylated fatty amides, fatty acid glycol
  • 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, for example distearyldimonium chloride
  • the 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 chosen 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-) ⁇ -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
  • the polyethoxylated or polypropoxylated or polyethoxylated and polypropoxylated O / W emulsifiers chosen 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 the ethoxylated stearyl alcohols, cetyl alcohols, cetylstearyl alcohols (cetearyl alcohols).
  • the following are particularly preferred: Polyethylene glycol (13) stearyl ether (steareth-13), polyethylene glycol (14) stearyl ether (steareth-14), polyethylene glycol (15) stearyl ether (steareth-15), polyethylene glycol (16) stearyl ether (steareth-16), polyethylene glycol (17) stearyl ether ( Steareth-17), polyethylene glycol (18) stearyl ether (Steareth-18), polyethylene glycol (19) stearyl ether (Steareth-19), polyethylene glycol (20) - stearyl ether (Steareth-20),
  • Polyethylene glycol (12) lauryl ether (Laureth-12), polyethylene glycol (12) isolauryl ether (Isolureth-12).
  • the 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 isostearate, polyethylene glycol (18) glyceryl oleate / cocoat to choose.
  • 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, diglycerin 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 atom
  • W / O emulsifiers are glyceryl stearate Glycerylmonoiso-, glyceryl monomyristate, glyceryl, diglyceryl monostearate, Diglycerylmono- isostearate, propylene glycol caprylate, propylene glycol monoisostearate, propylene glycol, propylene glycol, sorbitan, sorbitan, sorbitan monocaprylate, 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.
  • Example 1 (O / W cream):

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Abstract

L'invention concerne l'utilisation de carnitine et/ou d'une ou de plusieurs acyl-carnitines pour réaliser des préparations cosmétiques ou dermatologiques destinées à accroître la biosynthèse de céramide.
EP02747354A 2001-06-19 2002-06-07 Utilisation de carnitine et/ou d'une ou de plusieurs acyl-carnitines pour realiser des preparations cosmetiques ou dermatologiques destinees a accroitre la biosynthese de ceramide Ceased EP1401389A2 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP15185392.6A EP3009127A1 (fr) 2001-06-19 2002-06-07 Utilisation de carnitine et/ou d'une ou plusieurs acyl-carnitines destinees a la fabrication de preparations dermatologiques ou cosmetiques
EP15002815.7A EP3009124A1 (fr) 2001-06-19 2002-06-07 Utilisation de carnitine et/ou d'une ou plusieurs acyl-carnitines destinees a la fabrication de preparations dermatologiques ou cosmetiques pour la fabrication de preparation cosmetiques ou dermatologiques destinees a augmenter la biosynthese de ceramide

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10129502A DE10129502A1 (de) 2001-06-19 2001-06-19 Verwendung von Carnitin und/oder einem oder mehreren Acyl-Carnitinen zur Herstellung von kosmetischen oder dermatologischen Zubereitungen zur Steigerung der Ceramidbiosynthese
DE10129502 2001-06-19
PCT/EP2002/006254 WO2002102340A2 (fr) 2001-06-19 2002-06-07 Utilisation de carnitine et/ou d'une ou de plusieurs acyl-carnitines pour realiser des preparations cosmetiques ou dermatologiques destinees a accroitre la biosynthese de ceramide

Related Child Applications (2)

Application Number Title Priority Date Filing Date
EP15185392.6A Division EP3009127A1 (fr) 2001-06-19 2002-06-07 Utilisation de carnitine et/ou d'une ou plusieurs acyl-carnitines destinees a la fabrication de preparations dermatologiques ou cosmetiques
EP15002815.7A Division EP3009124A1 (fr) 2001-06-19 2002-06-07 Utilisation de carnitine et/ou d'une ou plusieurs acyl-carnitines destinees a la fabrication de preparations dermatologiques ou cosmetiques pour la fabrication de preparation cosmetiques ou dermatologiques destinees a augmenter la biosynthese de ceramide

Publications (1)

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EP1401389A2 true EP1401389A2 (fr) 2004-03-31

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Family Applications (3)

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EP02747354A Ceased EP1401389A2 (fr) 2001-06-19 2002-06-07 Utilisation de carnitine et/ou d'une ou de plusieurs acyl-carnitines pour realiser des preparations cosmetiques ou dermatologiques destinees a accroitre la biosynthese de ceramide
EP15002815.7A Withdrawn EP3009124A1 (fr) 2001-06-19 2002-06-07 Utilisation de carnitine et/ou d'une ou plusieurs acyl-carnitines destinees a la fabrication de preparations dermatologiques ou cosmetiques pour la fabrication de preparation cosmetiques ou dermatologiques destinees a augmenter la biosynthese de ceramide
EP15185392.6A Withdrawn EP3009127A1 (fr) 2001-06-19 2002-06-07 Utilisation de carnitine et/ou d'une ou plusieurs acyl-carnitines destinees a la fabrication de preparations dermatologiques ou cosmetiques

Family Applications After (2)

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EP15002815.7A Withdrawn EP3009124A1 (fr) 2001-06-19 2002-06-07 Utilisation de carnitine et/ou d'une ou plusieurs acyl-carnitines destinees a la fabrication de preparations dermatologiques ou cosmetiques pour la fabrication de preparation cosmetiques ou dermatologiques destinees a augmenter la biosynthese de ceramide
EP15185392.6A Withdrawn EP3009127A1 (fr) 2001-06-19 2002-06-07 Utilisation de carnitine et/ou d'une ou plusieurs acyl-carnitines destinees a la fabrication de preparations dermatologiques ou cosmetiques

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US (1) US20040176448A1 (fr)
EP (3) EP1401389A2 (fr)
JP (1) JP2004534068A (fr)
DE (1) DE10129502A1 (fr)
WO (1) WO2002102340A2 (fr)

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WO2007043339A1 (fr) * 2005-09-30 2007-04-19 Showa Denko K.K. Derive de carnitine, sel, preparation externe pour la peau et substance cosmetique
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US20040176448A1 (en) 2004-09-09
WO2002102340A3 (fr) 2003-07-17
DE10129502A1 (de) 2003-01-09
EP3009124A1 (fr) 2016-04-20
JP2004534068A (ja) 2004-11-11
EP3009127A1 (fr) 2016-04-20

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