EP0873111A1 - Formulations anti-uv cosmetiques et dermatologiques contenant des derives de triazine et des acides alcanecarboxyliques - Google Patents

Formulations anti-uv cosmetiques et dermatologiques contenant des derives de triazine et des acides alcanecarboxyliques

Info

Publication number
EP0873111A1
EP0873111A1 EP97902162A EP97902162A EP0873111A1 EP 0873111 A1 EP0873111 A1 EP 0873111A1 EP 97902162 A EP97902162 A EP 97902162A EP 97902162 A EP97902162 A EP 97902162A EP 0873111 A1 EP0873111 A1 EP 0873111A1
Authority
EP
European Patent Office
Prior art keywords
weight
tris
carboxylic acids
alkane carboxylic
acid
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.)
Withdrawn
Application number
EP97902162A
Other languages
German (de)
English (en)
Inventor
Heinrich Gers-Barlag
Rainer Kröpke
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Beiersdorf AG
Original Assignee
Beiersdorf AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Beiersdorf AG filed Critical Beiersdorf AG
Publication of EP0873111A1 publication Critical patent/EP0873111A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
    • 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
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • 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
    • 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

Definitions

  • Cosmetic and dermatological light protection formulations containing triazine derivatives and alkane carboxylic acids containing triazine derivatives and alkane carboxylic acids
  • the present invention relates to cosmetic and dermatological light protection preparations, in particular skin-care cosmetic and dermatological light protection preparations.
  • UVC range rays with a wavelength that is less than 290 nm
  • UVB range rays in the range between 290 nm and 320 nm, the so-called UVB range, cause erythema , a simple sunburn or even more or less severe burns.
  • the narrower range around 308 nm is given as a maximum of the erythema effectiveness of sunlight.
  • UVA range It is also important to have filter substances available for the range between about 320 nm and about 400 nm, the so-called UVA range, since their rays can also cause damage. It has been shown that UVA radiation damages the elastic and collagen fibers of the connective tissue, which causes the skin to age prematurely, and that it is the cause of numerous phototoxic and pho- allergic reactions can be seen. 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 interfere with the skin's metabolism.
  • radical compounds e.g. Hydroxyl radicals.
  • Undefined radical photo products which arise in the skin itself can also exhibit uncontrolled subsequent reactions due to their high reactivity.
  • singlet oxygen A non-radical excited state of the oxygen molecule can occur with UV radiation, as can short-lived epoxies and many others.
  • Singlet oxygen for example, is characterized by increased reactivity compared to the triplet oxygen that is normally present (basic radical state). However, there are also excited, reactive (radical) triplet states of the oxygen molecule.
  • UV radiation also belongs to ionizing radiation. There is therefore a risk that ionic species also develop when exposed to UV rays, which in turn can oxidatively intervene in the biochemical processes.
  • UVB filter is the 4,4,, 4 '- (1, 3,5-triazine-2,4,6-triyltriimino) tris benzoic acid tris (2-ethylhexyl), synonym: 2.4, 6-tris- [anilino- (p-carbo-2'-ethyl-1'-hexyloxy)] - 1,3,5-triazine.
  • This UVB firing substance is sold by BASF Aktiengesellschaft under the trade name UVINUL® T 150 and is characterized by good UV absorption properties.
  • UVB filter The main disadvantage of this UVB filter is the poor solubility in lipids.
  • Known solvents for this UVB filter can dissolve a maximum of approximately 15% by weight of this filter, corresponding to approximately 1 to 1.5% by weight of dissolved and thus active UV filter substance.
  • branched and / or unbranched alkane carboxylic acids with chain lengths of 10 to 24 carbon atoms, where at least 10% of these alkane carboxylic acids are or are present in protonated form, as a solvent, solubilizer or solubilizer for 4,4 ', 4 "- (1,3,5-Triazin-2,4,6-triyttriimino) -tris-benzoic acid ⁇ -tris (2- ⁇ thylh ⁇ xylester), especially for use in light stabilizers.
  • a prerequisite for the usability of the active compound combinations according to the invention for the purposes according to the invention is, of course, the cosmetic or dermatological harmlessness of the underlying substances.
  • alkane carboxylic acids stabilizes solutions of 4,4 ', 4 "- (1, 3,5-triazine-2 I 4,6-triyrtriimino) -tris-benzoic acid-tris (2-ethylhexyl ester) is effected since the latter substance not only has poor solubility, but also easily crystallizes out of its solution.
  • the total amount of 4,4'.4 "- (1,3,5-triazine-2,4,6-triyltriimino) -tris-benzoic acid tris (2-ethylhexyl ester) 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 one or more alkane carboxylic acids according to the invention in the finished cosmetic or dermatological preparations is 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.
  • weight hardenings of 4 > 4 ', 4 "- (1,3,5-triazine-2,4,6-triyttriimino) tris-benzoic acid tris (2-ethylhexyl ester) and one or more alkane carboxylic acids according to the invention from the range from 1:10 to 10: 1, preferably 1: 4 to 4: 1.
  • 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 (for example F ⁇ 2O3), zirconium (ZrO2) ), Silicon (Si ⁇ 2), manganese (e.g. MnO), aluminum (AI2O3), cerium (e.g. C ⁇ 2 ⁇ 3), mixed oxides of the corresponding metals as well as mixtures of such oxides. It is particularly preferred to use pigments based on TiO 2
  • the inorganic pigments are present 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.
  • Such a method consists, for example, in that the hydrophobic surface layer according to a direction
  • n and m are stoichiometric parameters to be used at will, R and R 'are the desired organic radicals.
  • hydrophobized pigments shown in analogy to DE-OS 33 14 742 are advantageous.
  • Advantageous TiO 2 pigments are available, for example, from TAYCA under the trade names MT 100 T.
  • the cosmetic and / or dermatological light protection formulations according to the invention can be composed as usual and serve the cosmetic and / or dermatological light protection, furthermore 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.
  • 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, e.g. Preservatives, bactericides, perfumes, substances to prevent foaming, dyes, pigments which have a coloring effect, thickeners, moisturizing and / or moisturizing substances, fats, oils, waxes or other customary components of a cosmetic or dermatological formulation tion such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.
  • cosmetic auxiliaries e.g. Preservatives, bactericides, perfumes, substances to prevent foaming, dyes, pigments which have a coloring effect, thickeners, moisturizing and / or moisturizing substances, fats, oils, waxes or other customary components of a cosmetic or dermatological formulation tion such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.
  • 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 granted from the group consisting of amino acids (eg glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (eg urocanic acid) and their derivatives, peptides such as D, L-carnosine, D-camosine, L-camosine and its derivatives (eg anserine), carotenoids, carotenes (eg ⁇ -carotene, ⁇ -carotene, lycopene) and their derivatives, chlorogenic acid and their derivatives, lipoic acid and their derivatives (eg dihydroliponic acid), aurothioglucose, propytthiouracil and other thiols (eg thioredoxin, glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoy
  • ⁇ -hydroxy fatty acids e.g. Ci tronic acid, lactic acid, malic acid
  • humic acid e.g. Ci tronic acid, lactic acid, malic acid
  • humic acid e.g. Ci tronic acid, lactic acid, malic acid
  • humic acid e.g. Ci tronic acid, lactic acid, malic acid
  • humic acid e.g. Ci tronic acid, lactic acid, malic acid
  • humic acid e acid, bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives
  • unsaturated fatty acids and their derivatives eg ⁇ -linolenic acid, linoleic acid, oleic acid
  • folic acid and their derivatives furfurylidene sorbitol and its derivatives
  • ubiquinone and ubiquinol and their derivatives vitamin C and derivatives (for example ascor
  • ZnO, ZnS ⁇ 4 selenium and its derivatives (e.g. selenium methionine), stilbene and its derivatives (e.g. stilbene oxide, trans-stilbene oxide) and the derivatives suitable according to the invention (sentences, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids) of these active substances.
  • 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 ⁇ tung.
  • 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.
  • 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 with a low C number, for example with isopropanol, propylene glycol or glycerol. or esters of fatty alcohols with low C number alkanoic acids or with fatty acids: alkyl benzoates;
  • Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenyipolysiloxanes and mixed forms thereof.
  • Alcohols, diols or polyols of low C number, and their ethers preferably ethanol, isopropanol, propylene glycol, glycerin, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether, diethylene glycol monomethyl or monoethyl ether and similar products , furthermore low C-number alcohols, e.g.
  • Ethanol, isopropanol, 1,2-propanediol, glycerol and in particular one or more thickeners which one or more can advantageously be selected from the group silicon dioxide, aluminum silicates, polysaccharides or their derivatives, e.g. Hyaluronic acid, xanthan gum, hydroxypropylmethylcellulose, 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, each 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, based 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 the filter substances is, 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 preparations, for cosmetic preparations to provide that protect the skin from the entire range of ultraviolet radiation. They can also serve as sunscreens.
  • 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;
  • UVB filters which can be used in combination with the active ingredient 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, especially 1- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1,3-dione and 1-phenyl-3- (4'-isopropylphenyl) propane-1,3 -dion.
  • These combinations or preparations which contain these combinations are also the subject of the invention.
  • the amounts used for the UVB combination can be used.
  • the invention also relates to a process for the preparation of the cosmetic and / or dermatological light protection preparations according to the invention, which is characterized in that the 4,4 ', 4 "- (1,3,5-triazine 2,4 1 6-triyltriimino) -tris-benzoic acid ⁇ -tris (2- ⁇ thylhexyl ester) suspended in one or more alkane carboxylic acids or an oil phase containing alkane carboxylic acids with uniform stirring and, if appropriate, with heating and, if desired, if homogenized, if appropriate combined with further lipid components and optionally combined with one or more emulsifiers, then the oil phase is mixed with the aqueous phase, into which a thickener has optionally been incorporated, and which preferably has about the same temperature as the oil phase, if desired, homogenized and Allow to cool to room temperature. After cooling to room temperature, further homogenization can take place, especially if volatile constituents are to be incorporated.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Emergency Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Toxicology (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne des combinaisons de substances actives filtrant les UV, constituées de tris(2-éthylhexylester) d'acide 4,4',4''-(1,3,5-triazine-2,4,6-triyltriimino)-tris-benzoïque et d'acides alcanecarboxyliques à chaîne ramifiée et/ou non ramifiée, d'une longueur de chaîne de 10 à 24 atomes de carbone, ces acides alcanecarboxyliques étant présents dans une proportion d'au moins 10 % sous une forme ayant subi une protonation.
EP97902162A 1996-01-13 1997-01-04 Formulations anti-uv cosmetiques et dermatologiques contenant des derives de triazine et des acides alcanecarboxyliques Withdrawn EP0873111A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19601104A DE19601104A1 (de) 1996-01-13 1996-01-13 Kosmetische und dermatologische Lichtschutzzubereitungen mit einem Gehalt an Triazinderivaten und Alkancarbonsäuren
DE19601104 1996-01-13
PCT/EP1997/000029 WO1997025020A1 (fr) 1996-01-13 1997-01-04 Formulations anti-uv cosmetiques et dermatologiques contenant des derives de triazine et des acides alcanecarboxyliques

Publications (1)

Publication Number Publication Date
EP0873111A1 true EP0873111A1 (fr) 1998-10-28

Family

ID=7782715

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97902162A Withdrawn EP0873111A1 (fr) 1996-01-13 1997-01-04 Formulations anti-uv cosmetiques et dermatologiques contenant des derives de triazine et des acides alcanecarboxyliques

Country Status (5)

Country Link
US (1) US6080388A (fr)
EP (1) EP0873111A1 (fr)
JP (1) JP2000503018A (fr)
DE (1) DE19601104A1 (fr)
WO (1) WO1997025020A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU7913798A (en) * 1997-05-23 1998-12-11 Unichema Chemie Bv Uv absorbent compositions
DE19831107A1 (de) * 1998-07-11 2000-01-13 Beiersdorf Ag Kosmetische und dermatologische Lichtschutzformulierungen mit einem Gehalt an Triazinderivaten und Alkancarbonsäuren bzw. deren Salzen
US20020110604A1 (en) * 2000-08-11 2002-08-15 Ashni Naturaceuticals, Inc. Composition exhibiting synergistic antioxidant activity
DE10111039A1 (de) * 2001-03-06 2002-09-12 Beiersdorf Ag Verwendung von Wirkstoffkombinationen aus alpha-Liponsäure und dermatologisch verträglichen Substanzen, die Lichtabsorption im UV-A-Bereich und/oder UV-B-Bereich zeigen, zur Herstellung von kosmetischen oder dermatologischen Zubereitungen zur Behandlung und/oder Prophylaxe der Symptome der intrinsischen und/oder extrinsischen Hautalterung sowie zur Behandlung und Prophylaxe der schädlichen Auwirkungen ultravioletter Strahlung auf die Haut
US20090136438A1 (en) * 2007-07-25 2009-05-28 Dermaplus, Inc. Photo-protective dermatological formulations and methods of using the same

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3408406A1 (de) * 1984-03-08 1985-09-12 Beiersdorf Ag, 2000 Hamburg Licht- und sonnenschutzmittel
FR2662079B1 (fr) * 1990-05-18 1993-11-05 Oreal Emulsion cosmetique filtrante comprenant un filtre uv-a et un filtre uv-b et son utilisation pour la protection de la peau contre les radiations ultraviolettes.
FR2720641B1 (fr) * 1994-06-03 1996-07-26 Oreal Compositions cosmétiques antisolaires comprenant de la 2,4,6-tris[p-(2'-éthylhexyl-1'-oxycarbonyl)anilino]-1,3,5-triazine et du malate de dioctyle et utilisations.
FR2720640B1 (fr) * 1994-06-03 1996-07-26 Oreal Compositions cosmétiques photoprotectrices à base d'un mélange synergétique de filtres et de nanopigments et utilisations.
FR2720637B1 (fr) * 1994-06-03 1996-07-26 Oreal Compositions cosmétiques photoprotectrices à base d'un mélange synergétique de filtres et utilisations.

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9725020A1 *

Also Published As

Publication number Publication date
DE19601104A1 (de) 1997-07-17
WO1997025020A1 (fr) 1997-07-17
JP2000503018A (ja) 2000-03-14
US6080388A (en) 2000-06-27

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