WO1999053894A1 - Preparations cosmetiques et dermatologiques ayant une teneur en derives de triazine substitues de façon asymetrique et une action de protection contre la lumiere, ces preparations etant resistantes a l'eau et se presentant sous forme d'emulsions huile/eau - Google Patents

Preparations cosmetiques et dermatologiques ayant une teneur en derives de triazine substitues de façon asymetrique et une action de protection contre la lumiere, ces preparations etant resistantes a l'eau et se presentant sous forme d'emulsions huile/eau Download PDF

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WO1999053894A1
WO1999053894A1 PCT/EP1999/002575 EP9902575W WO9953894A1 WO 1999053894 A1 WO1999053894 A1 WO 1999053894A1 EP 9902575 W EP9902575 W EP 9902575W WO 9953894 A1 WO9953894 A1 WO 9953894A1
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group
unbranched
branched
radical
preparations
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PCT/EP1999/002575
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German (de)
English (en)
Inventor
Heinrich Gers-Barlag
Birgit Hargens
Anja MÜLLER
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Beiersdorf Ag
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Priority to EP99922098A priority Critical patent/EP1073411A1/fr
Priority to JP2000544302A priority patent/JP2002512178A/ja
Publication of WO1999053894A1 publication Critical patent/WO1999053894A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • 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
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4966—Triazines or their condensed derivatives
    • 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

Definitions

  • Cosmetic or dermatological preparations containing unsymmetrically substituted triazine derivatives which waterproof light protection preparations in the form of
  • the present invention relates to cosmetic and dermatological preparations containing unsymmetrically substituted triazine derivatives.
  • the present invention relates to cosmetic and dermatological light protection preparations, in particular skin care cosmetic and dermatological light protection preparations.
  • the present invention relates to waterproof light protection preparations.
  • UVC range rays with a wavelength shorter than 290 nm
  • UVB range rays in the range between 290 nm and 320 nm, the so-called UVB range, cause erythema simple sunburn or even more or less severe skin burns.
  • the narrower range around 308 nm is regarded as a maximum of the erythema effectiveness of sunlight.
  • UVB radiation Numerous compounds are known to protect against UVB radiation, most of which are derivatives of 3-benzylidene camphor, 4-aminobenzoic acid, cinnamic acid, salicylic acid, benzophenone and also 2-phenylbenzimidazole. can. It has been proven that UVA radiation leads to damage to the elastic and collagen fibers of the connective tissue, which causes the skin to age prematurely and can be seen as the cause of numerous phototoxic and photoallergic reactions. The damaging influence of UVB radiation can be intensified by UVA radiation.
  • UV radiation can also lead to photochemical reactions, in which case the photochemical reaction products intervene in the skin and cell metabolism.
  • radical compounds e.g. Hydroxy radicals, hydroperoxy radicals and superoxide ions.
  • Undefined radical photo products which are created in the skin itself, can also display uncontrolled subsequent reactions due to their high reactivity.
  • singlet oxygen a non-radical excited state of the oxygen molecule, can occur with UV radiation, just as short-lived epoxies and many others.
  • Singlet oxygen for example, is characterized by increased reactivity compared to the triplet oxygen normally present (radical ground state). However, there are also excited, reactive (radical) triplet states of the oxygen molecule.
  • antioxidants and / or free radical scavengers can be incorporated into the cosmetic or dermatological formulations.
  • UV absorbers or UV reflectors are most inorganic pigments that are known to be used in cosmetics to protect the skin from UV rays. These are oxides of titanium, zinc, iron, zirconium, silicon, manganese, aluminum, cerium and mixtures thereof, as well as modifications.
  • Sunscreen preparations are particularly often required and used on bathing beaches or in outdoor pools. It is then desirable that the light protection formulation is largely water-resistant, so that it is not washed off the skin or only to a small extent.
  • Water-soluble UV filter substances are electrolytes which, in particular, destabilize O / W emulsions.
  • polyethoxylated emulsifiers are used.
  • these often have dermatological disadvantages, because the use of the usual cosmetic emulsifiers is harmless. Nevertheless, emulsifiers, like any chemical substance, can cause allergic or hypersensitive reactions in individual cases.
  • the prior art usually uses non-water-soluble UV filter substances, water-repellent raw materials (e.g. silicone oils in high concentrations) and / or film formers, in particular high-molecular compounds (e.g. PVP / hexadecene copolymers). This creates barriers between the UV filter substances on the skin and the water.
  • water-repellent raw materials e.g. silicone oils in high concentrations
  • film formers e.g. PVP / hexadecene copolymers
  • symmetrically substituted s-triazines have three identical substituents and are represented, for example, by the 4,4 ', 4 "- (1,3,5-triazine-2,4,6-triyltriimino) tris-benzoic acid tris (2-ethylhexyl ester), analogous to the INCI nomenclature: octyltriazon, which is represented by the following structure:
  • s-triazine derivatives which are unsymmetrically substituted with respect to the C 3 axis have different substituents, as a result of which the C 3 symmetry is destroyed.
  • “symmetrical” or “asymmetrical” is always understood to be symmetrical or asymmetrical with respect to the C 3 axis of the triazine base, unless something else was expressly mentioned.
  • EP-A-570 838 describes unsymmetrically substituted s-triazine derivatives whose chemical structure is represented by the generic formula
  • R represents a branched or unbranched C 8 -alkyl radical, a C 5 -C 2 -cycloalkyl radical, optionally substituted with one or more dC - alkyl groups
  • X represents an oxygen atom or an NH group
  • Ri represents a branched or unbranched C 1 -C 8 8 -alkyl radical, a C 5 -C 2 cycloalkyl radical, optionally substituted with one or more C 1 -C 4 alkyl groups, or a
  • Hydrogen atom an alkali metal atom, an ammonium group or a group of
  • A represents a branched or unbranched d-cis-alkyl radical, a Cs-C 2 -cycloalkyl or aryl radical, optionally substituted with one or more d-
  • R 3 represents a hydrogen atom or a methyl group
  • n represents a number from 1 to 10
  • Ci-Cis-alkyl radical a C 5 -C 12 cycloalkyl radical, optionally substituted with one or more C ⁇ - C - alkyl groups, when X represents the NH group, and a branched or unbranched C cis-alkyl radical, a Cs -C 2 -cycloalkyl radical, optionally substituted with one or more dC 4 - alkyl groups, or a hydrogen atom, an alkali metal atom, an ammonium group or a group of the formula
  • A represents a branched or unbranched d-cis-alkyl radical, a C 5 -d 2 -cycloalkyl or aryl radical, optionally substituted by one or more d-
  • R 3 represents a hydrogen atom or a methyl group
  • n represents a number from 1 to 10 when X represents an oxygen atom.
  • Such s-triazine derivatives which in contrast to 4,4 ', 4 "- (1,3,5-triazine-2,4,6-triyltrimino) -tris-benzoic acid tris (2-ethylhexyl ester) improved by Characterize solubility in many oil components, according to the teaching of documents EP-A-821 937, EP-A-821 938, EP-A-821 939, EP-A-821 940 and EP-A-821 941 with different other light protection filters can be combined in cosmetic or dermatological preparations, in order to take account of certain technical facts, and sulfonated UV filter substances are also mentioned as optional components of the formulations mentioned in the abovementioned documents.
  • a further object of the present invention was to provide light protection preparations which are notable for a high light protection action and good cosmetic and dermatological acceptance.
  • the present invention relates to the use of combinations of active ingredients which act to protect against light
  • R represents a branched or unbranched C 1 -C 8 -alkyl radical, a Cs-C 1 -cycloalkyl radical, optionally substituted by one or more C 1 -C 4 -alkyl groups
  • X represents an oxygen atom or an NH group
  • R T represents a branched or unbranched C 1 -C 8 alkyl radical, a C 3 -C 2 cycloalkyl radical, optionally substituted with one or more CrC 4 alkyl groups, or a
  • Hydrogen atom an alkali metal atom, an ammonium group or a group of
  • A represents a branched or unbranched dC 18 -alkyl radical, a Cs-Cir-cycloalkyl or aryl radical, optionally substituted by one or more d- C 4 -alkyl groups,
  • R 3 represents a hydrogen atom or a methyl group
  • n represents a number from 1 to 10
  • a branched or unbranched C 1 -C 8 alkyl radical a C 5 -C 2 cycloalkyl radical, optionally substituted with one or more C 1 -C 4 alkyl groups
  • X represents the NH group
  • a branched or unbranched C 1 -C 8 alkyl radical a C 3 -C 2 cycloalkyl radical, optionally substituted with one or more dC 4 alkyl groups, or a
  • Hydrogen atom an alkali metal atom, an ammonium group or a group of
  • A represents a branched or unbranched d-cis-alkyl radical, a Cs-C 12 -cycloalkyl or aryl radical, optionally substituted by one or more d-
  • R 3 represents a hydrogen atom or a methyl group
  • n represents a number from 1 to 10
  • X represents an oxygen atom
  • the present invention relates to the use of combinations of active ingredients which act to protect against light
  • Advantageous water-soluble UV filter substances in the sense of the present invention are in particular those which carry one or more sulfonic acid groups or sulfonate groups on their molecular structure.
  • the following are particularly preferred:
  • the 2-phenylbenzimidazole-5-sulfonic acid and its salts for example the sodium, potassium or its triethanolammonium salt
  • Sulfonic acid derivatives of benzophenones preferably 2-hydroxy-4-methoxybenzophenon-5-sulfonic acid and their salts, for example the corresponding sodium, potassium or triethanolammonium salt:
  • water-soluble UV filter substances used according to the invention which carry a sulfonic acid group or sulfonate group on their molecular structure, extremely 12
  • UV filter substances which have two or more sulfonic acid groups or sulfonate groups on their molecular structure are often preferred.
  • Medical topical compositions usually contain one or more drugs in effective concentration.
  • drugs for the sake of simplicity, reference is made to the legal provisions of the Federal Republic of Germany (e.g. cosmetics regulation, food and drug law) for a clear distinction between cosmetic and medical use and corresponding products.
  • the present invention relates to light protection preparations in the form of O / W emulsions comprising active compound combinations
  • IR 6 distinguish, wherein R 4 represents a branched or unbranched alkyl radical having 1 to 24 carbon atoms, where R 5 represents either a hydrogen atom or a branched or unbranched alkyl radical having 1 to 24 carbon atoms and where R ⁇ either represents a hydrogen atom or a branched or unbranched acyl radical Represents 1 to 24 carbon atoms, and.
  • the present invention relates to light protection preparations in the form of O / W emulsions comprising active ingredient combinations
  • IR 6 distinguish, wherein R 4 represents a branched or unbranched alkyl radical having 1 to 24 carbon atoms, where R 5 represents either a hydrogen atom or a branched or unbranched alkyl radical having 1 to 24 carbon atoms and where Rs either represents a hydrogen atom or a branched or unbranched acyl radical Represents 1 to 24 carbon atoms, and which
  • R 7 , R 8 and R 9 are selected from the group which comprises: H, branched or unbranched, saturated or unsaturated fatty acid residues with 8 to 24 carbon atoms, in which up to three aliphatic hydrogen atoms can be substituted by hydroxyl groups and n represents a number from 2 to 8, and which
  • (e) are essentially free of polyethoxylated emulsifiers.
  • R 4 is advantageously selected from the group of unbranched alkyl radicals, preference being given to the myristyl radical, the palmityl radical, the stearyl radical and the eicosyl radical.
  • R 5 can advantageously represent a hydrogen atom, but is preferably selected from the group consisting of methyl, ethyl, propyl and isopropyl.
  • Re can advantageously represent a hydrogen atom, but can also advantageously be selected from the group consisting of myristoyl, palmitoyl, stearoyl and eicosoyl.
  • the surface-active substances A from the group methyl glucose monostearate (formula as below) will be or will be particularly advantageous.
  • methylglucose sesquistearate any mixtures thereof, for example approximately equimolar mixtures thereof, which are also referred to as methylglucose sesquistearate.
  • methyl glucose sesquistearate is commercially available, for example, under the trade name Tego® Care PS from the company Th.Goldschmidt KG.
  • the surface-active substances B are also selected with particular advantage from the group of compounds in which n assumes the value 3 and R 3 , R 4 and R 5 are selected independently of one another from the group which comprises: H, branched or unbranched , saturated or unsaturated fatty acid residues with 14 to 20 carbon atoms, in particular the structures listed below:
  • an approximately equimolecular mixture of the compounds A2 and B1 has turned out to be the preferred emulsifier combination according to the invention, the radicals R 7 and R 9 in B1 preferably both denoting a stearate radical.
  • emulsifier combinations are available as "Polyglyceryl (3) -methylglucose distearate” (PGMS) under the trade name Tego Care® 450 from the company Th. Goldschmidt KG.
  • the total amount of the water-soluble UV filter substance or substances in the finished cosmetic or dermatological preparations is advantageously chosen in the range from 0.1-10.0% by weight, preferably 0.5-6.0% by weight on the total weight of the preparations.
  • the total amount of 2-phenylbenzimidazole-5-sulfonic acid (if it is this substance which is to be used as a sulfonated UV filter substance in the sense of the present invention) or its salts in the finished cosmetic or dermatological preparations is advantageously from the range of 0.1-10.0% by weight, preferably 0.5-6.0% by weight, based on the total weight of the preparations.
  • the total amount of 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid (if it is this substance which is to be used as a sulfonated UV filter substance in the sense of the present invention) or its salts in the finished cosmetic or dermatological preparations is advantageously obtained the range of 0.1-10.0% by weight, preferably 0.5-6.0% by weight, based on the total weight of the preparations.
  • the total amount of 4- (2-oxo-3-bomylidenemethyl) benzenesulfonic acid (if it is this substance which is to be used as a sulfonated UV filter substance in the sense of the present invention) or its salts in the finished cosmetic or dermatological preparations is advantageous selected from the range of 0.1-10.0% by weight, preferably 0.5-6.0% by weight, based on the total weight of the preparations. 17
  • the total amount of 2-methyl-5- (2-oxo-3-bornylidenemethyl) benzenesulfonic acid (if it is this substance which is to be used as a sulfonated UV filter substance in the sense of the present invention) or its salts in the finished cosmetic or dermatological preparations are advantageously selected from the range from 0.1 to 10.0% by weight, preferably 0.5 to 6.0% by weight, based on the total weight of the preparations.
  • the total amount of benzene-1,4-di (2-oxo-3-bornylidenemethyl-10-sulfonic acid (if it is this substance which is to be used as a sulfonated UV filter substance in the sense of the present invention) or its salts in the Finished cosmetic or dermatological preparations are advantageously chosen from the range of 0.1-10.0% by weight, preferably 0.5-6.0% by weight, based on the total weight of the preparations.
  • the total amount of one or more asymmetrically substituted s-triazine derivatives, in particular dioctylbutylamidotriazone, in the finished cosmetic or dermatological preparations is advantageously in the range from 0.1 to 15.0% by weight, preferably 0.5 to 8.0% by weight .-% selected, based on the total weight of the preparations.
  • 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. It is particularly preferred to use pigments based on TiO 2 .
  • 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 Ti0 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.
  • the cosmetic and / or dermatological light protection formulations according to the invention can be composed as usual and can be used for cosmetic and / or dermatological light protection, also for the treatment, care and cleaning of the skin and / or hair and as a make-up product in decorative cosmetics.
  • the cosmetic and dermatological preparations according to the invention are applied to the skin and / or the hair in a sufficient amount in the manner customary for cosmetics.
  • Those cosmetic and dermatological preparations which are in the form of a sunscreen are particularly preferred. These can advantageously additionally contain at least one further UVA filter and / or at least one further UVB filter and / or at least one inorganic pigment, preferably an inorganic micropigment.
  • the cosmetic and dermatological preparations according to the invention can contain cosmetic auxiliaries as are usually used in such preparations, for example preservatives, bactericides, perfumes, substances for preventing foaming, dyes, pigments which have a coloring effect, thickeners, moisturizing and / / or moisturizing substances, fats, oils, waxes or other usual components of a cosmetic or dermatological formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives. 19
  • cosmetic auxiliaries as are usually used in such preparations, for example preservatives, bactericides, perfumes, substances for preventing foaming, dyes, pigments which have a coloring effect, thickeners, moisturizing and / / or moisturizing substances, fats, oils, waxes or other usual components of a cosmetic or dermatological formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives. 19
  • antioxidants are generally preferred. According to the invention, all the antioxidants suitable or customary for cosmetic and / or dermatological applications can be used as favorable antioxidants.
  • 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-camosin, D-camosin, L- Camosin and its derivatives (e.g. Anserin), carotenoids, carotenes (e.g. ⁇ -carotene, ⁇ -carotene, lycopene) and their derivatives, chlorogenic acid and their derivatives, lipoic acid and their derivatives (e.g.
  • amino acids eg glycine, histidine, tyrosine, tryptophan
  • imidazoles eg urocanic acid
  • peptides such as D, L-camosin, D-camosin, L- Camosin and its derivatives (e.g. Anserin)
  • 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
  • salts dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (e.g.
  • buthionine sulfoximines homocysteine sulfoximine, buthionine Penta-, hexa-, heptathioninsulfoximine
  • very low tolerable doses e.g. pmol to ⁇ mol / kg
  • metal chelators eg ⁇ -hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin
  • ⁇ -hydroxy acids eg 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.
  • the amount of the aforementioned antioxidants (one or more compounds) in the preparations is preferably 0.001 to 30% by weight, particularly preferably 0.05-20% by weight, in particular 1-10% by weight, based on the total weight of the Preparation. 20th
  • vitamin E and / or its derivatives represent the antioxidant (s)
  • vitamin A or vitamin A dehvate 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.
  • the lipid phase can advantageously be selected from the following group of substances: mineral oils, mineral waxes
  • Oils such as triglycerides of capric or caprylic acid, but preferably castor oil; Fats, waxes and other natural and synthetic fat bodies, preferably esters of fatty acids with alcohols 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.
  • the oil phase of the emulsions, oleogels or hydrodispersions or lipodispersions for the purposes of the present invention is advantageously selected from the group of esters from saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 3 to 30 carbon atoms and saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 3 to 30 C atoms, from the group of esters from aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 3 to 30 C 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, ethyl-2-ethylhexyl, ethyl-2-ethylhexyl 2-octyldodecyl palmitate, oleyl oleate, olerlerucate, erucyl oleate, erucylerucate and 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, e.g. 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 -i 5 -alkyl benzoate, caprylic capric acid triglyceride, dicaprylyl ether.
  • Particularly advantageous are mixtures of C 2 - ⁇ s benzoate and 2-ethylhexyl isostearate, mixtures of C 12- i 5 -alkyl benzoate and isotridecyl isononanoate and mixtures of C ⁇ . 2 15-alkylbenzoate, 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 advantageously also contain cyclic or linear silicone oils or consist entirely of such oils, although it is preferred to use an additional content of other oil phase components in addition to the silicone oil or the silicone oils.
  • Cyclomethicone (octamethylcyclotetrasiloxane) is advantageously used as the silicone oil to be used according to the invention. But other silicone oils are also advantageous in the sense of 22
  • hexamethylcyclotrisiloxane for example hexamethylcyclotrisiloxane, polydimethylsiloxane, poly (methylphenylsiloxane).
  • 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 analog products, furthermore alcohols of low C number, for example Ethanol, isopropanol, 1, 2-propanediol, glycerol and in particular one or more thickeners, which one or more can advantageously be selected from the group consisting of silicon dioxide, aluminum silicates, poiysaccharides or their derivatives, e.g.
  • Hyaluronic acid, xanthan gum, hydroxypropylmethyl cellulose particularly advantageously from the group of polyacrylates, preferably a polyacrylate from the group of so-called carbopoles, for example carbopoles of types 980, 981, 1382, 2984, 5984, in each case individually or in combination.
  • 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 further 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, is in particular 1 to 6% by weight, based on the total weight of the preparations, in order to 23
  • the other 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;
  • 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'-methoxyphenyr) propane-1,3-dione and 1-phenyl-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.
  • Sorbitan monstearate 1 Sorbitan monstearate 1, 00

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  • Cosmetics (AREA)

Abstract

L'invention concerne des associations d'agents actifs ayant une action de protection contre la lumière. Ces associations sont composées (a) d'au moins une substance filtre U.V. soluble dans l'eau, notamment de substances qui portent sur leur squelette de molécule au moins un groupe d'acide sulfonique ou de sulfonate et (b) d'au moins un dérivé de s-triazine substitué de façon asymétrique. Ces associations sont utilisées pour produire des préparations de protection contre la lumière, résistantes à l'eau et se présentant sous forme d'émulsions huile/eau.
PCT/EP1999/002575 1998-04-18 1999-04-16 Preparations cosmetiques et dermatologiques ayant une teneur en derives de triazine substitues de façon asymetrique et une action de protection contre la lumiere, ces preparations etant resistantes a l'eau et se presentant sous forme d'emulsions huile/eau WO1999053894A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP99922098A EP1073411A1 (fr) 1998-04-18 1999-04-16 Preparations cosmetiques et dermatologiques ayant une teneur en derives de triazine substitues de fa on asymetrique et une action de protection contre la lumiere, ces preparations etant resistantes a l'eau et se presentant sous forme d'emulsions huile/eau
JP2000544302A JP2002512178A (ja) 1998-04-18 1999-04-16 油／水エマルションの形態の水抵抗性日焼け止め調製物を表す、非対称的に置換されたトリアジン誘導体を含む化粧品又は皮膚科学的調製物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19817296A DE19817296A1 (de) 1998-04-18 1998-04-18 Kosmetische oder dermatologische Zubereitungen mit einem Gehalt an unsymmetrisch substituierten Triazinderivaten, welche wasserfeste Lichtschutzzubereitungen in Form von O/W-Emulsionen darstellen
DE19817296.6 1998-04-18

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Publication Number Publication Date
WO1999053894A1 true WO1999053894A1 (fr) 1999-10-28

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PCT/EP1999/002575 WO1999053894A1 (fr) 1998-04-18 1999-04-16 Preparations cosmetiques et dermatologiques ayant une teneur en derives de triazine substitues de façon asymetrique et une action de protection contre la lumiere, ces preparations etant resistantes a l'eau et se presentant sous forme d'emulsions huile/eau

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EP (1) EP1073411A1 (fr)
JP (1) JP2002512178A (fr)
DE (1) DE19817296A1 (fr)
WO (1) WO1999053894A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003030859A2 (fr) * 2001-10-04 2003-04-17 Beiersdorf Ag Emulsions huile dans l'eau contenant des principes actifs non polaires
WO2003082237A2 (fr) * 2002-03-28 2003-10-09 Beiersdorf Ag Formulations de protection solaire cosmetiques et dermatologiques hydroresistantes contenant une quantite d'esters acetyles de l'acide stearique
EP2005938A1 (fr) * 2007-06-14 2008-12-24 Beiersdorf AG Préparations cosmétiques ou dermatologiques ayant une teneur en oxygène moléculaire, dérivés de glucose actifs en surface et de préférence une ou plusieurs substances absorbant la lumière UV

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0507407D0 (en) * 2005-04-13 2005-05-18 Shaikh Jim Self-heating fluid connector
DE202006007976U1 (de) 2006-05-15 2006-07-20 Beiersdorf Ag Sprühbares Sonnenschutzmittel

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WO1995022313A1 (fr) * 1994-02-22 1995-08-24 Henkel Kommanditgesellschaft Auf Aktien Emulsions
EP0796851A1 (fr) * 1996-03-22 1997-09-24 3V SIGMA S.p.A Dérivés de s-triazine en tant qu'agent antisolaire
EP0821942A2 (fr) * 1996-08-02 1998-02-04 Beiersdorf Aktiengesellschaft Formulations cosmétiques et dermatologiques de protection solaire contenant des dérivés de triazine et des dérivés de glucose tensio-actifs
DE19631222A1 (de) * 1996-08-02 1998-02-12 Beiersdorf Ag Stabile Lichtschutzzubereitungen mit einem Gehalt an grenzflächenaktiven Glucosederivaten und wasserlöslichen UV-Filtersubstanzen
DE19631219A1 (de) * 1996-08-02 1998-02-12 Beiersdorf Ag Wasserfeste Lichtschutzzubereitungen mit einem Gehalt an anorganischen Mikropigmenten und wasserlöslichen UV-Filtersubstanzen
EP0838214A2 (fr) * 1996-10-22 1998-04-29 Basf Aktiengesellschaft Compositions cosmétiques comprenant une combinaison d'absorbants d'UV, y compris un dérivé de triazine
DE19726785A1 (de) * 1997-06-24 1999-01-07 Beiersdorf Ag Kosmetische und dermatologische Lichtschutzformulierungen mit einem Gehalt an s-Triazinderivaten und Alkylglukosiden
WO1999006014A2 (fr) * 1997-07-30 1999-02-11 3V Sigma S.P.A. Combinaisons d'ecrans solaires et compositions les contenant
EP0904770A1 (fr) * 1997-08-13 1999-03-31 Beiersdorf Aktiengesellschaft Utilisation des oxydes amorphous aux rayons X pour renforcer le facteur photoprotectif et/ou la UV-protection des agents photoprotectifs cosmétiques ou dermatologiques

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FR2674851B1 (fr) * 1991-04-04 1995-02-10 Oreal Derives s-triaziniques portant des substituants benzylidene camphre, compositions cosmetiques filtrantes et leur utilisation pour proteger la peau et les cheveux du rayonnement ultraviolet.
FR2674850B1 (fr) * 1991-04-04 1993-07-02 Oreal Derives s-triaziniques portant des substituants benzalmalonates, compositions cosmetiques filtrantes les contenant et leur utilisation pour proteger la peau et les cheveux du rayonnement ultraviolet.
DE19631221C2 (de) * 1996-08-02 1999-07-01 Beiersdorf Ag Schaumförmige Lichtschutzzubereitungen mit einem Gehalt an wasserlöslichen Lichtschutzfiltersubstanzen und grenzflächenaktiven Substanzen

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995022313A1 (fr) * 1994-02-22 1995-08-24 Henkel Kommanditgesellschaft Auf Aktien Emulsions
EP0796851A1 (fr) * 1996-03-22 1997-09-24 3V SIGMA S.p.A Dérivés de s-triazine en tant qu'agent antisolaire
EP0821942A2 (fr) * 1996-08-02 1998-02-04 Beiersdorf Aktiengesellschaft Formulations cosmétiques et dermatologiques de protection solaire contenant des dérivés de triazine et des dérivés de glucose tensio-actifs
DE19631222A1 (de) * 1996-08-02 1998-02-12 Beiersdorf Ag Stabile Lichtschutzzubereitungen mit einem Gehalt an grenzflächenaktiven Glucosederivaten und wasserlöslichen UV-Filtersubstanzen
DE19631219A1 (de) * 1996-08-02 1998-02-12 Beiersdorf Ag Wasserfeste Lichtschutzzubereitungen mit einem Gehalt an anorganischen Mikropigmenten und wasserlöslichen UV-Filtersubstanzen
EP0838214A2 (fr) * 1996-10-22 1998-04-29 Basf Aktiengesellschaft Compositions cosmétiques comprenant une combinaison d'absorbants d'UV, y compris un dérivé de triazine
DE19726785A1 (de) * 1997-06-24 1999-01-07 Beiersdorf Ag Kosmetische und dermatologische Lichtschutzformulierungen mit einem Gehalt an s-Triazinderivaten und Alkylglukosiden
WO1999006014A2 (fr) * 1997-07-30 1999-02-11 3V Sigma S.P.A. Combinaisons d'ecrans solaires et compositions les contenant
EP0904770A1 (fr) * 1997-08-13 1999-03-31 Beiersdorf Aktiengesellschaft Utilisation des oxydes amorphous aux rayons X pour renforcer le facteur photoprotectif et/ou la UV-protection des agents photoprotectifs cosmétiques ou dermatologiques

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003030859A2 (fr) * 2001-10-04 2003-04-17 Beiersdorf Ag Emulsions huile dans l'eau contenant des principes actifs non polaires
WO2003030859A3 (fr) * 2001-10-04 2003-09-12 Beiersdorf Ag Emulsions huile dans l'eau contenant des principes actifs non polaires
EP1897527A1 (fr) * 2001-10-04 2008-03-12 Beiersdorf AG Emulsions huile dans l'eau contenant des principes actifs non polaires
WO2003082237A2 (fr) * 2002-03-28 2003-10-09 Beiersdorf Ag Formulations de protection solaire cosmetiques et dermatologiques hydroresistantes contenant une quantite d'esters acetyles de l'acide stearique
WO2003082237A3 (fr) * 2002-03-28 2004-02-05 Beiersdorf Ag Formulations de protection solaire cosmetiques et dermatologiques hydroresistantes contenant une quantite d'esters acetyles de l'acide stearique
EP2005938A1 (fr) * 2007-06-14 2008-12-24 Beiersdorf AG Préparations cosmétiques ou dermatologiques ayant une teneur en oxygène moléculaire, dérivés de glucose actifs en surface et de préférence une ou plusieurs substances absorbant la lumière UV

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DE19817296A1 (de) 2000-01-20
EP1073411A1 (fr) 2001-02-07
JP2002512178A (ja) 2002-04-23

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