WO1996037187A1 - Cosmetic or dermatological preparations containing phytic acid - Google Patents
Cosmetic or dermatological preparations containing phytic acid Download PDFInfo
- Publication number
- WO1996037187A1 WO1996037187A1 PCT/EP1996/002197 EP9602197W WO9637187A1 WO 1996037187 A1 WO1996037187 A1 WO 1996037187A1 EP 9602197 W EP9602197 W EP 9602197W WO 9637187 A1 WO9637187 A1 WO 9637187A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid
- hair
- skin
- cosmetic
- preparations
- Prior art date
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- IMQLKJBTEOYOSI-UHFFFAOYSA-N Phytic acid Natural products OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 title claims abstract description 38
- IMQLKJBTEOYOSI-GPIVLXJGSA-N Inositol-hexakisphosphate Chemical compound OP(O)(=O)O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O IMQLKJBTEOYOSI-GPIVLXJGSA-N 0.000 title claims abstract description 37
- 229940068041 phytic acid Drugs 0.000 title claims abstract description 37
- 239000000467 phytic acid Substances 0.000 title claims abstract description 36
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- JGHSBPIZNUXPLA-UHFFFAOYSA-N 2-hydroxyhexadecanoic acid Chemical compound CCCCCCCCCCCCCCC(O)C(O)=O JGHSBPIZNUXPLA-UHFFFAOYSA-N 0.000 claims description 26
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- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000004792 oxidative damage Effects 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- LXTZRIBXKVRLOA-UHFFFAOYSA-N padimate a Chemical compound CCCCCOC(=O)C1=CC=C(N(C)C)C=C1 LXTZRIBXKVRLOA-UHFFFAOYSA-N 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 231100000760 phototoxic Toxicity 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960002662 propylthiouracil Drugs 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- IKGXIBQEEMLURG-BKUODXTLSA-N rutin Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 description 1
- 229960004555 rutoside Drugs 0.000 description 1
- 229940071089 sarcosinate Drugs 0.000 description 1
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 241000894007 species Species 0.000 description 1
- WWUZIQQURGPMPG-KRWOKUGFSA-N sphingosine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO WWUZIQQURGPMPG-KRWOKUGFSA-N 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- ARCJQKUWGAZPFX-UHFFFAOYSA-N stilbene oxide Chemical compound O1C(C=2C=CC=CC=2)C1C1=CC=CC=C1 ARCJQKUWGAZPFX-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 150000001629 stilbenes Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- AGGIJOLULBJGTQ-UHFFFAOYSA-N sulfoacetic acid Chemical class OC(=O)CS(O)(=O)=O AGGIJOLULBJGTQ-UHFFFAOYSA-N 0.000 description 1
- 125000005555 sulfoximide group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229960002663 thioctic acid Drugs 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- 229940094937 thioredoxin Drugs 0.000 description 1
- 108060008226 thioredoxin Proteins 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 125000002640 tocopherol group Chemical class 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- ZCIHMQAPACOQHT-ZGMPDRQDSA-N trans-isorenieratene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/c1c(C)ccc(C)c1C)C=CC=C(/C)C=Cc2c(C)ccc(C)c2C ZCIHMQAPACOQHT-ZGMPDRQDSA-N 0.000 description 1
- LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical compound OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 0.000 description 1
- LOIYMIARKYCTBW-UHFFFAOYSA-N trans-urocanic acid Natural products OC(=O)C=CC1=CNC=N1 LOIYMIARKYCTBW-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical class OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 229940040064 ubiquinol Drugs 0.000 description 1
- QNTNKSLOFHEFPK-UPTCCGCDSA-N ubiquinol-10 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC QNTNKSLOFHEFPK-UPTCCGCDSA-N 0.000 description 1
- 229940035936 ubiquinone Drugs 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
- A61K31/661—Phosphorus acids or esters thereof not having P—C bonds, e.g. fosfosal, dichlorvos, malathion or mevinphos
- A61K31/6615—Compounds having two or more esterified phosphorus acid groups, e.g. inositol triphosphate, phytic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/14—Liposomes; Vesicles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—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
-
- 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
- A61K8/55—Phosphorus compounds
-
- 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
- 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
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
- A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
- A61Q1/06—Lipsticks
-
- 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
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/51—Chelating agents
-
- 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
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/522—Antioxidants; Radical scavengers
Definitions
- the invention relates to active ingredients and cosmetic or dermatological preparations, in particular topical preparations, which alleviate the consequential damage of substances with an oxidizing effect or acute or chronic light exposure, in particular exposure to ultraviolet light, and those which have an oxidizing effect before the consequential damage or acute or chronic light UV exposure protect, i.e. act preventively.
- UVA radiation is also the cause of numerous phototoxic and photo-allergic reactions. It can also increase the harmful effects of UVB radiation.
- ketoproteins result from an oxidative modification of side groups of amino acid residues of the protein. A carbonyl group is introduced into these side chains with the participation of strong oxidizing agents (for example H 2 0 2 ).
- strong oxidizing agents for example H 2 0 2 .
- ketoproteins also serve as markers for the UV or oxygen radical-induced damage to proteins of the epidermis. Human hair is also exposed to the damaging effects of UV light and weathered as it ages, among other things due to the oxidative splitting of stabilizing disulfide bridges.
- high concentrations of hydrogen peroxides are used in a large number of hair dyeing processes, which may possibly cause damage to the hair substance as a side effect.
- the photochemical reaction products are predominantly radical compounds, for example hydroxyl radicals.
- Undefined radical photo products which arise in the skin and hair itself, can also initiate uncontrolled subsequent reactions due to their high reactivity.
- singlet oxygen, a non-radical, excited and very reactive state of the oxygen molecule can occur with UV radiation, just as short-lived epoxies and many others.
- UV radiation also belongs to ionizing radiation. There is therefore a risk that ionic species will also be formed on UV exposure, which in turn, e.g. can oxidatively intervene in biochemical processes of the skin
- Typical UVB filters are derivatives of 3-benzylidene camphor, 4-aminobenzoic acid, cinnamic acid, salicylic acid, benzophenone and 2-phenylbenzimidazole. To protect the skin from UVA radiation, certain derivatives of dibenzoylmethane are mostly used.
- UV filters pose the following problems for the consumer: They only have a protective, but no therapeutic effect. To ensure optimal protection, the filter substances must cover the skin permanently with an even and evenly distributed film. However, these requirements can hardly be met, since wrinkles permeate the surface of the skin and the user often moves or sweats in water under sunlight. In addition, UV filters can harbor a certain risk of irritation for mucous membranes and occasionally cause a burning sensation on sensitive areas of the skin (stinging potential).
- topical preparations are admixed with UV-reflecting or UV-scattering substances.
- Substances such as titanium dioxide or zinc oxide fulfill this task, but give the preparations an unattractive, whitish color. In addition, it is not always possible to adequately fix these substances on the skin surface.
- antioxidants and / or radical scavengers can also be added to cosmetic or dermatological preparations.
- Antioxidants are substances that prevent oxidation processes in the surrounding medium (skin, hair or product).
- Antioxidants which are used in the fields of cosmetics and pharmacy are, for example, ⁇ -tocopherol, in particular in the form of ⁇ -tocopherol acetate, butylated hydroxyanisole and butylated hydroxytoluene.
- vitamin E a substance with a known antioxidative, that is to say oxygen radical neutralizing, effect in sunscreen formulations, but the effect achieved here still falls short of the hoped-for effect.
- An object of the present invention was to eliminate the disadvantages of the prior art.
- an active ingredient or preparations containing this active ingredient should be made available, the use of which can reduce or reduce the damage to the skin and / or hair due to oxidative influence, for example by reducing the formation of ketoproteins.
- a further object of the present invention was to provide cosmetic preparations in particular which counteract the aging of the hair or before or after treatment of the hair with bleaching agents or hair dye preparations, even those with a high content of strong oxidizing agents, for example hydrogen peroxide, the harmful oxidizing effect of which.
- the invention relates to the use of phytic acid or its salts for the prophylaxis and treatment of damaging oxidative effects on the skin or the hair.
- the invention also relates to the use of cosmetic or dermatological preparations containing phytic acid or its salts for the prophylaxis and treatment of damaging oxidative effects on the skin or the hair.
- Topical preparations are preferred.
- Phytic acid (myo-inositol hexaphosphate, international free name: fytic acid) is known and described in the literature ("Römpp Chemie Lexikon", 9th edition, Georg Thieme Verlag, Stuttgart, DE, p. 3431 (1991) and "The Merck Index, 11 Edition, Merck & Co., Inc., Rahway, USA, p. 1172 (1989).
- the invention also relates to combinations of active substances containing one or more active substances selected from the group of phytic acid and its salts in combination with one or more active substances selected from the group of chelating agents.
- Preferred chelating agents are alpha-hydroxy fatty acids and their salts or deferoxamine and its acid addition salts.
- active ingredients also extends to the active ingredient combinations and preparations with them.
- cosmetic or dermatological preparations characterized by a content of an active ingredient combination containing one or more active ingredients, selected from the group of phytic acid and its salts in combination with an active ingredient or more active ingredients, selected from the group of chelating agents, are the subject of Invention.
- Topical preparations are preferred.
- Combinations are preferred which contain one or more alpha-hydroxy fatty acids as chelating agents and / or deferoxamine.
- the invention also relates to the use of active substance combinations containing one or more active substances, selected from the group of phytic acid and its salts, in combination with an active substance or more active substances, selected from the group of chelating agents, for the prophylaxis and treatment of damaging oxidative effects on the skin or hair.
- cosmetic or dermatological preparations characterized by a content of a combination of active substances, containing one or more active substances, selected from the group of phytic acid and its salts in combination with one or more active substances, selected from the group of chelating agents, for the prophylaxis and treatment of damaging oxidative effects on the skin or the hair.
- Mixtures of alpha-hydroxy fatty acids can be formed by two, more or even a larger number of compounds and contain these compounds in different amounts by weight.
- fractions from natural sources can have a larger number due to Have homologues or structural isomers, however, synthesized acids can consist of one compound each.
- the alpha-hydroxy fatty acids according to the invention can be straight-chain or branched.
- the saturated, aliphatic alpha-hydroxy fatty acids are preferred.
- Preferred alpha-hydroxy fatty acids according to the invention contain 8 to 20 carbon atoms, but in particular 14 to 18 carbon atoms, particularly preferably 16 carbon atoms. Mixtures of the fatty acids in such areas are also advantageous.
- alpha-hydroxy fatty acids and their salts are particularly preferred:
- alpha-hydroxy fatty acids obtained from wool wax can also be used, e.g. Alpha-hydroxy fatty acid mixtures obtainable according to known isolation processes (DE-A-2 04 321) which are obtained from wool wax acid mixtures. They are preferably obtained as a D-enantiomer mixture. The individual compounds obtainable by known processes are also preferred.
- alpha-hydroxy fatty acids according to the invention are known or can be obtained by known processes. Racemates obtained in the synthesis can be split into the isomers in customary processes.
- Preferred salts of the active compounds according to the invention are compatible salts, in particular water-soluble salts, for example the sodium or potassium salts.
- the active compounds according to the invention are preferably used in the acid form.
- ⁇ -Hydroxy fatty acids are natural components of the lipid membranes present in the human horny layer. They are bound to the sphingosine of ceramides 4, 5 and 61 or 611 in an amide-like manner and can be released by an enzyme present in the horny layer, ceramidase. They have no UV-absorbing properties and are therefore not attributable to the filter substances.
- ⁇ -Hydroxypalmitic acid is regarded as a particularly advantageous ⁇ -hydroxy fatty acid in the sense of the present invention.
- the ⁇ -hydroxypalmitic acid is a natural component of the wool wax acid ⁇ of sheep, which is also a source of this active ingredient for cosmetic or dermatological preparations.
- Deferoxamine is known from the literature and the free international short name for desferrioxamine or also 30-amino-3,14,25-trihydroxy-3,9, 14,20,25-pentaazatriacontan-2, 10, 13,21, 24-pentaon ("Römpp Chemie Lexikon", 9th edition, Georg Thieme Verlag, Stuttgart, p. 876 (1991) and "The Merck Index", 11th edition, Merck & Co., Inc., Rahway, USA, p. 449 ( 1989).
- Preferred acid addition salts are compatible salts, especially water soluble salts, e.g. the hydrochloride.
- oxidative action is to be understood both to mean the action of substances having an oxidizing action and also the oxidative action of radiation, namely light, in particular UV light and the secondary products caused thereby.
- damage are meant those effects which cause undesirable changes in the skin or hair, for example aging, or ketoprotein formation but, for example, not the desired bleaching effect of hair bleaches or, for example, the desired effect of hair colors.
- the active substances and preparations according to the invention are distinguished in that they alleviate the consequential damage of oxidizing substances or acute or chronic light exposure, in particular exposure to ultraviolet light, and protect them from the consequential damage of oxidizing substances or acute or chronic light exposure or UV exposure, i.e. preventively Act.
- the active compounds and preparations according to the invention reduce the formation of ketoproteins in the skin and reduce or prevent the skin changes or skin damage which occur with skin aging, in particular endogenous skin aging and photoaging of the skin. They have a preventive effect, but they can also repair damage that has already occurred.
- the active substances and preparations according to the invention for the prophylaxis and treatment of skin changes and skin damage caused by skin aging, in particular endogenous skin aging and photoaging of the skin and ketoprotein formation.
- the active substances and preparations according to the invention can be used with UVA and / or UVB radiation.
- the hair is also subject to a constant aging process, which is mainly based on oxidative effects.
- the dye chromophore is formed by the reaction of precursors (phenols, aminophenols, more rarely diamines) and bases (mostly p-phenylenediami ⁇ ) with the oxidizing agent, mostly hydrogen peroxide. Hydrogen peroxide concentrations around 6% are usually used.
- the hydrogen peroxide also has a bleaching effect.
- oxidatively colored human hair similar to bleached hair, microscopic holes can be detected at the places where Meianingranuia was present.
- the oxidizing agent hydrogen peroxide not only reacts with the color precursors but also with the hair substance and can cause damage to the hair.
- Oxidative agents that can cause damage are also used for bleaching hair and shaping hair.
- the invention particularly relates to the use of the active compounds and preparations according to the invention for the prophylaxis and treatment of hair damage caused by hair cosmetics, e.g. Bleaching agents, colorants and shaping agents.
- hair cosmetics e.g. Bleaching agents, colorants and shaping agents.
- Proteins better prevent ketoprotein formation in the skin, reduce the aging effect, protect the skin against photoreactions, better absorb the skin
- the cosmetic or dermatological preparations or formulations according to the invention can be composed as usual and can be used for the treatment, care and cleaning of the skin and / or hair and as a make-up product in decorative cosmetics.
- phytic acid or its Salt They contain e.g. 0.001 to 20 wt .-%, preferably 0.1 wt .-% to 10 wt .-%, but in particular 0.1 wt .-% to 3 wt .-%, each based on the total weight of the preparations of phytic acid or its Salt.
- the proportion of the active compound combinations according to the invention in the preparations is, for example 0.001 to 10% by weight, preferably 0.1% to 5% by weight, but in particular 0.1% to 1% by weight, in each case based on the total weight of the preparations.
- the weight ratio of the phytic acid or its salts to that of the chelating agent is advantageously 20: 1 to 1:20, preferably 5: 1 to 1: 5, particularly preferably approximately 2: 1 to 1: 2.
- 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. Preparations for the treatment and care of the skin are particularly preferred.
- Cosmetic and dermatological preparations according to the invention can be in various forms.
- they can be a solution, an anhydrous preparation, an emulsion or microemission of the water-in-oil (W / O) or oil-in-water (O / W) type, multiple emulsions, for example of the water- in-oil-in-water (W / O / W), a gel, a solid stick, an ointment or an aerosol.
- W / O water-in-oil
- O / W oil-in-water
- An advantageous embodiment of the present invention is therefore also the use of active substances according to the invention for protecting the skin and / or hair from oxidative damage, in particular this use of the active substances according to the invention in shampoos and washing formulations.
- 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 that have a coloring effect, thickeners, surface-active substances, emulsifiers, softening, 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.
- cosmetic auxiliaries e.g. Preservatives, bactericides, perfumes, substances to prevent foaming, dyes, pigments that have a coloring effect, thickeners, surface-active substances, emulsifiers, softening, moisturizing and / or moisturizing substances, fats, oils, waxes or other usual components of a cosmetic or dermatological formulation such as alcohols, polyols, polymers, foam stabilizer
- the active compounds according to the invention can also be combined with antioxidants for the effects according to the invention.
- Such combinations are also the subject of the invention, as are the uses as have already been stated for the active compounds.
- 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-carnosine,
- D-carnosine, L-camosine and their derivatives e.g. anserine
- carotenoids e.g. carotenoids
- Carotenes e.g. ⁇ -carotene, ⁇ -carotene, lycopene
- Carotenes e.g. ⁇ -carotene, ⁇ -carotene, lycopene
- Chlorogenic acid and its derivatives e.g., Chlorogenic acid and its derivatives, lipoic acid and its derivatives (e.g., Chlorogenic acid and its derivatives, lipoic acid and its derivatives (e.g., Chlorogenic acid and its derivatives, lipoic acid and its derivatives (e.g., Chlorogenic acid and its derivatives, lipoic acid and its derivatives (e.g., Chlorogenic acid and its derivatives, lipoic acid and its derivatives (e.g., Chlorogenic acid and its derivatives, lipoic acid and its derivatives (e.g., Chlorogenic acid and its derivatives, lipoic acid and its derivatives (e.g., Chlorogenic acid and its derivatives, lipoic acid and its derivatives (e.g.
- Dihydrolipoic acid Dihydrolipoic acid
- aurothioglucose e.g., aurothioglucose
- propylthiouracil e.g., thioie
- Derivatives esters, ethers, peptides, lipids, nucleotides, nucleosides and salts
- sulfoximine compounds e.g. buthionine sulfoximines
- Heptathioninsulfoximine in very low tolerable doses (e.g. pmol to ⁇ mol / kg), humic acid, bile acid, bile extracts, bilirubin, biliverdin,
- Ascorbyl palmitate Mg ascorbyl phosphate, ascorbyl acetate), tocopherols and
- Derivatives e.g. vitamin E acetate
- vitamin A and derivatives vitamin A palmitate
- coniferyl benzoate of the benzin resin rutinic acid and its derivatives
- Stilbenes and their derivatives e.g. stilbene oxide, trans-stilbene oxide
- derivatives suitable according to the invention salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids
- 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.
- vitamin E and / or its derivatives represent the antioxidant or antioxidants, it is advantageous to have their respective concentrations in the range of 0.001-10% by weight, based on the total weight of the formulation.
- 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.
- Emulsions according to the invention are advantageous and contain e.g. the said fats, oils, waxes and other fat bodies, as well as water and an emulsifier, as is usually used for such a type of formulation.
- oils such as triglycerides of capric or caprylic acid, but preferably castor oil;
- Fats, waxes and other natural synthetic and / or partially 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;
- Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiloxanes and mixed forms thereof.
- saturated compounds such as hydrocarbons of natural or synthetic origin (petroleum jelly, squalane)
- 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 analogous products, furthermore alcohols of low carbon 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 silicon dioxide, aluminum silicates, polysaccharides or their derivatives, e.g.
- hyaluronic acid, xanthan gum, hydroxypropylmethyl cellulose particularly advantageously from the group of the polyacrylates, preferably a polyacrylate from the group of the so-called carbopoles, for example carbopoles of types 980, 981, 1382, 2984, 5984, or also of types ETD ( Easy-to-disperse) 2001, 2020, 2050, each individually or in any combination with each other.
- carbopoles for example carbopoles of types 980, 981, 1382, 2984, 5984, or also of types ETD ( Easy-to-disperse) 2001, 2020, 2050, each individually or in any combination with each other.
- Water can also be a component of alcoholic solvents.
- Emulsions according to the invention are advantageous and contain e.g. the fats, oils, waxes and other fat bodies mentioned, as well as water and an emulsifier, as is usually used for such a type of formulation.
- Gels according to the invention usually contain alcohols of low carbon number, for example ethanol, isopropanol, 1, 2-propanediol, glycerin, and water or an 'abovementioned oil in the presence of a thickener, preferably in oily-alcoholic gels is silicon dioxide or an aluminum silicate, in the case of aqueous-alcoholic or alcoholic gels is preferably a polyacrylate.
- alcohols of low carbon number for example ethanol, isopropanol, 1, 2-propanediol, glycerin, and water or an 'abovementioned oil in the presence of a thickener, preferably in oily-alcoholic gels is silicon dioxide or an aluminum silicate, in the case of aqueous-alcoholic or alcoholic gels is preferably a polyacrylate.
- Suitable propellants for preparations according to the invention which can be sprayed from aerosol containers are the customary, known volatile, liquefied propellants, for example hydrocarbons (propane, butane, isobutane), which can be used alone or in a mixture with one another. Compressed air can also be used advantageously.
- hydrocarbons propane, butane, isobutane
- Preparations according to the invention can also advantageously contain substances which absorb UV radiation in the UVB range, the Total amount of the filter substances is, for example, 0.1% 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, to provide cosmetic preparations that protect the hair or skin from the entire range of ultraviolet radiation. They can also serve as a sunscreen for the hair or skin.
- the emulsions according to the invention contain UVB filter substances, they can be oil-soluble or water-soluble.
- Oil-soluble UVB filters which are advantageous according to the invention are, for example:
- 3-benzylidene camphor derivatives preferably 3- (4-methylbenzylidene) camphor, 3-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;
- 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, 2,4,6-trianiiino- (p-carbo-2'-ethyl-1 '- hexyloxy) -1, 3,5-triazine.
- 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 e.g. 4- (2-oxo-3-bornylidene methyl) benzenesulfonic acid, 2-methyl-5- (2-oxo-3-bornylidene methyl) sulfonic acid and their salts.
- UVB filters mentioned, which can be used in combination with the active compounds according to the invention, should of course not be limiting.
- the invention also relates to the use of the active compounds according to the invention with at least one UVB filter as an antioxidant or the use of the active compounds according to the invention with at least one UVB filter in a cosmetic or dermatological preparation.
- UVA filters can also be advantageous to combine active ingredients according to the invention with UVA filters.
- suitable are those which have hitherto usually been contained in cosmetic preparations.
- These substances are preferably derivatives of dibenzoylmethane, in particular 1- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1, 3-dione and 1-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.
- the invention also relates to the use of a combination of the active compounds according to the invention with at least one UVA filter or the use of a combination of the active compounds according to the invention with at least one UVA filter in a cosmetic or dermatological preparation.
- the invention also relates to the use of a combination of the active compounds according to the invention with at least one UVA filter and at least one UVB filter or the use of a combination of Active substances according to the invention with at least one UVA filter and at least one UVB filter in a cosmetic or dermatological preparation.
- Cosmetic and dermatological preparations with an effective content of active substances according to the invention can also contain inorganic pigments which are usually 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 in which the oxides are the active agents. It is particularly preferred to use pigments based on titanium dioxide.
- UVA filter and pigment or preparations containing this combination are also the subject of the invention.
- the amounts given for the above combinations can be used.
- Cosmetic and dermatological preparations for protecting the hair from UV rays according to the invention are, for example, shampooing agents, preparations which are used when rinsing the hair before or after the shampooing, before or after the permanent wave treatment, before or after the coloring or discoloration of the Hair is applied to preparations for blow-drying or pickling hair, preparations for coloring or decolouring, to a styling and treatment lotion, a hair lacquer or to permanent waving agents.
- the combinations with UV filters and UV protective substances have the effects described for the active substances and can be used in the same way.
- the cosmetic and dermatological preparations contain active substances and auxiliaries as are usually used for this type of preparations for hair care and hair treatment.
- auxiliaries Preservatives, surface-active substances, substances to prevent foaming, thickening agents, emulsifiers, fats, oils, waxes, organic solvents, bactericides, perfumes, dyes or pigments, the task of which is to dye the hair or the cosmetic or dermatological preparation itself, electrophoresis , Substances against greasy hair.
- Electrolytes for the purposes of the present invention are water-soluble alkali metal, ammonium, alkaline earth metal (including magnesium) and zinc salts of inorganic anions and any mixtures of such salts, it being necessary to ensure that these salts are pharmaceutically or cosmetically harmless award.
- the anions according to the invention are preferably selected from the group of chlorides, sulfates and hydrogen sulfates, phosphates, hydrogen phosphates and linear and cyclic oligophosphates as well as carbonates and hydrogen carbonates.
- Cosmetic preparations which are a skin cleansing agent or shampooing agent preferably contain at least one anionic, non-ionic or amphoteric surface-active substance, or else mixtures of such substances, active substance combinations according to the invention in an aqueous medium and auxiliaries as are usually used therefor.
- the surface-active substance or the mixtures of these substances can be present in the shampoo in a concentration of between 1% and 50% by weight.
- the cosmetic or dermatological preparations are in the form of a lotion which is rinsed out and used, for example, before or after decolorization, before or after shampooing, between two shampooing steps, before or after permanent wave treatment, these are, for example, aqueous or aqueous alcoholic solutions, which may contain surface-active substances, the concentration of which may be between 0.1 and 10% by weight, preferably between 0.2 and 5% by weight.
- aqueous or aqueous alcoholic solutions which may contain surface-active substances, the concentration of which may be between 0.1 and 10% by weight, preferably between 0.2 and 5% by weight.
- These cosmetic or dermatological preparations can also be aerosols with the auxiliaries usually used for them.
- a cosmetic preparation in the form of a lotion that is not rinsed out, in particular a lotion for inlaying the hair, a lotion used for blow-drying the hair, a styling and treatment lotion generally provides an aqueous, alcoholic or aqueous-alcoholic solution represents and contains at least one cationic, anionic, non-ionic or amphoteric polymer or mixtures thereof, as well as active ingredient combinations according to the invention in effective concentration.
- the amount of the polymers used is e.g. between 0.1 and 10% by weight, preferably between 0.1 and 3% by weight.
- Cosmetic preparations for the treatment and care of the hair which contain active ingredients according to the invention, can be present as emulsions which are of the non-ionic or anionic type.
- non-ionic emulsions contain oils or fatty alcohols, which can also be polyethoxylated or polypropoxylated, for example, or also mixtures of the two organic components.
- These emulsions may contain cationic surface-active substances.
- cosmetic preparations for the treatment and care of the hair can be in the form of gels which, in addition to an effective content of active compound combinations according to the invention and the solvents usually used for them, preferably water, and also organic thickeners, for example gum arabic, xanthan gum, sodium alginate, cellulose derivatives, preferably methyl cellulose, hydroxymethyl cellulose , Hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose or inorganic thickeners, for example aluminum silicates such as bentonites, or a mixture of polyethylene glycol and polyethylene glycol stearate or distearate.
- organic thickeners for example gum arabic, xanthan gum, sodium alginate, cellulose derivatives, preferably methyl cellulose, hydroxymethyl cellulose , Hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose or inorganic thickeners, for example aluminum silicates such as bentonites, or a mixture of
- the thickener is contained in the gel, for example, in an amount between 0.1 and 30% by weight, preferably between 0.5 and 15% by weight.
- the amount of the active compounds according to the invention in an agent intended for the hair is preferably 0.05% by weight to 10% by weight, in particular 0.5% by weight to 5% by weight, based on the total weight of the agent.
- Aqueous cosmetic cleaning agents according to the invention or water-free or anhydrous cleaning agent concentrates intended for aqueous cleaning can contain anionic, nonionic and / or amphoteric surfactants, for example
- Cosmetic preparations which are cosmetic cleaning preparations for the skin, can be in liquid or solid form.
- they preferably contain at least one anionic, nonionic or amphoteric surface-active substance or mixtures thereof, if desired one or more electrolytes and auxiliaries of the kind usually used for this purpose.
- the surface-active substance can be present in the cleaning preparations in a concentration between 1 and 94% by weight, based on the total weight of the preparations.
- Cosmetic preparations which are a shampooing agent preferably contain, in addition to an effective content of active ingredients according to the invention, at least one anionic, nonionic or amphoteric surface-active substance or mixtures thereof, optionally an electrolyte and auxiliary according to the invention, as are usually used therefor.
- the surface-active substance can be present in the shampoo in a concentration between 1% by weight and 94% by weight.
- compositions according to the invention contain water and, if appropriate, the additives customary in cosmetics, for example perfume, thickeners, dyes, deodorants, antimicrobial substances, lipid-replenishing agents, complexing and sequestering agents, pearlescent agents, plant extracts, vitamins, active ingredients and the like.
- the additives customary in cosmetics for example perfume, thickeners, dyes, deodorants, antimicrobial substances, lipid-replenishing agents, complexing and sequestering agents, pearlescent agents, plant extracts, vitamins, active ingredients and the like.
- the present invention also encompasses a cosmetic or dermatological method for protecting the skin and hair from oxidative or photooxidative processes, which is characterized in that a cosmetic agent which contains an effective concentration of active compound combinations according to the invention is sufficient Apply a lot to the skin or hair.
- the active substances according to the invention can be used individually or as a mixture of several active substances and can also be contained individually or as a mixture in the preparations.
- the invention also relates to the process for the preparation of the cosmetic compositions according to the invention, which is characterized in that active ingredients according to the invention are incorporated into cosmetic and dermatological formulations in a manner known per se. This can e.g. done by stirring or emulsifying.
- Vitamin E acetate 2.00
- Titanium dioxide 1.00
- Paraffin oil, pigments and dyes ad 100.00
- Vitamin E acetate 2.00
- Titanium dioxide 1.00
- Paraffin oil, pigments and dyes ad 100.00
- Titanium dioxide 1.00
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Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP8535379A JPH11505818A (en) | 1995-05-23 | 1996-05-22 | Cosmetic or dermatological preparations containing phytic acid |
EP96917399A EP0827392A1 (en) | 1995-05-23 | 1996-05-22 | Cosmetic or dermatological preparations containing phytic acid |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19518845A DE19518845A1 (en) | 1995-05-23 | 1995-05-23 | Cosmetic or dermatological preparations containing phytic acid |
DE19518845.4 | 1995-05-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1996037187A1 true WO1996037187A1 (en) | 1996-11-28 |
Family
ID=7762628
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1996/002197 WO1996037187A1 (en) | 1995-05-23 | 1996-05-22 | Cosmetic or dermatological preparations containing phytic acid |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0827392A1 (en) |
JP (1) | JPH11505818A (en) |
DE (1) | DE19518845A1 (en) |
WO (1) | WO1996037187A1 (en) |
Cited By (5)
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CN101076316B (en) * | 2004-12-17 | 2011-11-09 | 株式会社资生堂 | Composition and method for accelerating fibulin-5 production and/or enhancing fibulin-5 activity |
CN103338746A (en) * | 2011-01-27 | 2013-10-02 | 太阳星光齿磨公司 | Composition containing polyunsaturated fatty acid |
US20210236398A1 (en) * | 2020-01-31 | 2021-08-05 | L'oreal | Compositions and methods for hair |
US20220362128A1 (en) * | 2019-06-27 | 2022-11-17 | L'oreal | Composition comprising ingredients for dic-gel and polyol |
WO2023034283A1 (en) * | 2021-08-30 | 2023-03-09 | Living Proof, Inc. | Methods for strengthening and repairing hair |
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DE10050155A1 (en) * | 2000-10-11 | 2002-04-18 | Beiersdorf Ag | Stabilization of cosmetic or dermatological emulsions, hydrogels or oleogels useful eg as skin-care or make-up compositions is by addition of desferrioxamine |
JP2005325034A (en) * | 2004-05-12 | 2005-11-24 | Okuno Chem Ind Co Ltd | Singlet oxygen eliminator |
JP4502903B2 (en) * | 2005-08-01 | 2010-07-14 | 中野製薬株式会社 | Two-component oxidative hair dye / bleaching agent composition |
JP4502904B2 (en) * | 2005-08-01 | 2010-07-14 | 中野製薬株式会社 | Two-component oxidative hair dye / bleaching agent composition |
WO2007039057A1 (en) * | 2005-09-23 | 2007-04-12 | Dsm Ip Assets B.V. | Cosmetic compositions comprising hydroxyfatty acids |
JP5279209B2 (en) * | 2006-06-27 | 2013-09-04 | ロート製薬株式会社 | Topical skin preparation |
JP6824823B2 (en) * | 2017-06-06 | 2021-02-03 | 株式会社マンダム | Nrf2 gene expression promoter, catalase gene expression promoter, and glutathione peroxidase gene expression promoter |
WO2024132679A1 (en) * | 2022-12-21 | 2024-06-27 | Evonik Dr. Straetmans Gmbh | Compositions containing biosurfactants and desferrioxamines |
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- 1996-05-22 JP JP8535379A patent/JPH11505818A/en active Pending
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CN101076316B (en) * | 2004-12-17 | 2011-11-09 | 株式会社资生堂 | Composition and method for accelerating fibulin-5 production and/or enhancing fibulin-5 activity |
CN103338746A (en) * | 2011-01-27 | 2013-10-02 | 太阳星光齿磨公司 | Composition containing polyunsaturated fatty acid |
CN103338746B (en) * | 2011-01-27 | 2015-12-23 | 太阳星光齿磨公司 | Compositions containing polyunsaturated fatty acid |
US20220362128A1 (en) * | 2019-06-27 | 2022-11-17 | L'oreal | Composition comprising ingredients for dic-gel and polyol |
US20210236398A1 (en) * | 2020-01-31 | 2021-08-05 | L'oreal | Compositions and methods for hair |
WO2023034283A1 (en) * | 2021-08-30 | 2023-03-09 | Living Proof, Inc. | Methods for strengthening and repairing hair |
Also Published As
Publication number | Publication date |
---|---|
JPH11505818A (en) | 1999-05-25 |
EP0827392A1 (en) | 1998-03-11 |
DE19518845A1 (en) | 1996-11-28 |
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