WO2015124233A1 - Préparations cosmétiques ou dermatologiques contenant au moins un dérivé de biphénylamine et utilisation d'au moins un dérivé de biphénylamine pour le bronzage de la peau - Google Patents

Préparations cosmétiques ou dermatologiques contenant au moins un dérivé de biphénylamine et utilisation d'au moins un dérivé de biphénylamine pour le bronzage de la peau Download PDF

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Publication number
WO2015124233A1
WO2015124233A1 PCT/EP2014/077887 EP2014077887W WO2015124233A1 WO 2015124233 A1 WO2015124233 A1 WO 2015124233A1 EP 2014077887 W EP2014077887 W EP 2014077887W WO 2015124233 A1 WO2015124233 A1 WO 2015124233A1
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WIPO (PCT)
Prior art keywords
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branched
groups
alkyl
connection
Prior art date
Application number
PCT/EP2014/077887
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German (de)
English (en)
Inventor
Andre Mahns
Torsten Schläger
Ludger Kolbe
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 WO2015124233A1 publication Critical patent/WO2015124233A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/04—Preparations for care of the skin for chemically tanning the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • 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
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid

Definitions

  • the present invention relates to cosmetic and dermatological preparations for tanning the skin, especially those which simultaneously provide protection against UV radiation.
  • UVC range rays with a wavelength less than 290 nm
  • UVB range rays in the range between 290 nm and 320 nm
  • the narrower range around 308 nm is given.
  • UVA range it is important to have available filter substances, since even its rays can cause damage.
  • UVA radiation has been shown to cause damage to the connective tissue's elastic and collagenous fibers, prematurely aging the skin, and to be the cause of many phototoxic and photoallergic reactions.
  • the damaging influence of UVB radiation can be amplified by UVA radiation.
  • UVA radiation can also cause skin damage by damaging the skin's own keratin or elastin. This reduces the elasticity and water retention of the skin, ie the skin becomes less supple and tends to wrinkle.
  • the strikingly high incidence of skin cancer in areas of strong sunlight shows that apparently too Damage to the genetic information in the cells by sunlight, especially caused by UV-Ashlhlung.
  • UV radiation can also lead to photochemical reactions, in which case the photochemical reaction products intervene in the skin metabolism.
  • such photochemical reaction products are free-radical compounds, e.g. Hydroxyl radicals.
  • Undefined radical photoproducts which develop in the skin itself, can also display uncontrolled sequelae due to their high reactivity.
  • singlet oxygen a non-radical excited state of the oxygen molecule can occur on UV irradiation, as well as short-lived epoxides and many others.
  • Singlet oxygen for example, is distinguished from the normally present triplet oxygen (radical ground state) by increased reactivity. However, there are also excited, reactive (radical) triplet states of the oxygen molecule.
  • UV radiation counts as ionizing radiation.
  • ionic species may also be formed upon UV exposure, which in turn may oxidatively interfere with the biochemical processes.
  • the pigmentation of human skin is essentially caused by the presence of melanin.
  • Melanin and its degradation products (melanoids), carotene, degree of blood flow and the nature and thickness of the stratum corneum and other skin layers make skin shades different from virtually white (with reduced filling or in the absence of blood vessels) or yellowish to light brown-reddish, bluish to brown Nuances and finally appear almost black.
  • the individual skin regions show different depth of color due to different amounts of melanin.
  • melanin protects the skin from penetrating UV radiation.
  • the number of melanin granules produced in the melanocytes determines whether they are light or dark skinned.
  • melanin With strong pigmentation (for example, in colored people, but also in fair-skinned persons after some UV irradiation), melanin is also found in the stratum spinosum and even in the stratum corneum. It attenuates UV radiation by up to about 90% before it reaches the corium.
  • the following skin types are usually distinguished:
  • Skin type II hardly tans, easily gets sunburned. Skin type III tans well on average.
  • Skin type V Dark, often almost black, skin never gets sunburned.
  • the natural shielding of harmful UV radiation is a tangible benefit of natural skin tanning.
  • a "healthy" skin color has been considered a sign of particular sporting activity and is therefore considered desirable by a broad consumer group, who are therefore dependent on self-tanning preparations for skin types I and II who wish to enjoy such a skin tint
  • skin type III who are not too exposed to the risks of sunbathing and still want to look tanned, are willing target groups for self-tanning preparations.
  • Carotene is stored in the subcutaneous adipose tissue by regular intake of carotene preparations, the skin gradually turns orange to yellow-brown. With the help of washable make-up preparations a slight skin tone can be achieved (for example extracts of fresh green walnut shells, henna)
  • the staining can also be done by way of chemical modification of the horny layer of the skin with so-called self-tanning preparations.
  • the most important active ingredient is dihydroxyacetone (DHA).
  • DHA dihydroxyacetone
  • the skin tanning achieved in this way is not washable and is only removed with the normal desquamation of the skin (after approx. 10-15 days).
  • Dihydroxyacetone can be referred to as ketotriose and reacts as reducing sugar with the amino acids of the skin or the free amino and imino groups of keratin via a series of intermediates in the sense of a Maillard reaction to brown-colored substances, so-called melanoids, which occasionally also called melanoidins.
  • a disadvantage of tanning with dihydroxyacetone is that the skin tanned with it is not protected against sunburn, as opposed to "tanned" skin.
  • formulations of the invention increase the pigmentation of the skin, allow a more uniform tanning of the skin, develop no undesirable odors when applied to the skin and avoid discoloration of the clothing after application to the skin.
  • Skin care products according to the invention advantageously contain from 0.00001 to 20% by weight of one or more biphenylamine derivatives.
  • A, B, C, D, E may be different, partly the same or completely the same and be independent of each other:
  • R 3 hydrogen, C 1 -C 24 -alkyl (branched and unbranched), C 1 -C 24 -alkenyl (branched and unbranched), C 1 -C 24 -hydroxyalkyl (branched and unbranched), C 1 -C 24 -methoxyalkyl (branched and unbranched), not mono- or polysubstituted indol-3-yl, non-mono- or polysubstituted indol-1-yl, CHPhPh, naphthyl, aromatic or aliphatic homo- or heterocyclic ring systems with up to n-ring-forming atoms, the number n being values of 3 to 8 and the respective ring systems may in turn be substituted by up to n-1 alkyl groups, hydroxyl groups, carboxyl groups, amino groups, nitrile functional groups, sulfur-containing substituents, halogens, ester groups, singly or multiply substituted benzyl groups and / or ether groups.
  • biphenylamine derivatives mentioned can be present both as free base and as salts: e.g. as fluoride, chloride, bromide, iodide, sulfate, carbonate, ascorbate, acetate or phosphate.
  • salts e.g. as fluoride, chloride, bromide, iodide, sulfate, carbonate, ascorbate, acetate or phosphate.
  • halogen salts e.g. Chloride and bromide.
  • the human primary melanocytes of three donors are combined in equal proportions before sowing into an assay plate.
  • the cells are seeded by means of multidrop (lab systems) in a total cell number of 7,500 cells per well of a 384 microtiter plate in a volume of 40 ⁇ l complete medium (MGM medium (CellSystems) including associated supplements).
  • MGM medium CellSystems
  • test substances are added in 1 1 different concentrations covering a range of 39nM to 40 ⁇ .
  • the test substances are in a volume of 15 ⁇ _ lean medium (MGM medium (Cell-Systems) without supplements) are added to the cells, followed by an incubation period of 4 days.
  • MGM medium Cell-Systems
  • Melanin is characterized by its light-absorbing effect, so that the measurement of melanogenesis via an absorption measurement (Synergy 4, BioTek) is carried out through the individual wells. These measurements are carried out at two times, firstly directly after the addition of the test substances (measurement I) and then at the end of their four-day incubation period (measurement II).
  • the measurement I serves above all to identify light-absorbing test substances which would interfere with the measurement methodology.
  • Measurement II serves to assess the extent to which the test substances to be investigated influence melanogenesis.
  • such preparations contain 0.00001 to 20% by weight, in particular 0.001 to 10% by weight, very particularly 0.005 to 1% by weight, of one or more of the biphenylamine derivatives used according to the invention on the total weight of the preparation.
  • Cosmetic and dermatological preparations according to the invention can be present in various forms:
  • they may contain a solution, an anhydrous preparation, an emulsion or microemulsion of the water-in-oil (W / O) or oil-in-water (O / W) type, a multiple emulsion, for example of the Water-in-oil-in-water (W / O / W), a gel, a solid stick, an ointment or even an aerosol.
  • W / O water-in-oil
  • O / W oil-in-water
  • W Water-in-oil-in-water
  • W Water-in-oil-in-water
  • a gel for example of the Water-in-oil-in-water
  • solid stick for example encapsulated as cellulose encapsulates, encapsulated in gelatin or liposomally.
  • the cosmetic and dermatological preparations according to the invention may comprise cosmetic adjuvants conventionally used in such preparations, for example preservatives, bactericides, perfumes, foaming inhibitors, colorants, pigments having a coloring effect, thickeners, surface-active substances, emulsifiers, softening, moisturizing and / or moisturizing substances, fats, oils, waxes or other customary constituents of a cosmetic or dermatological formulation, such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.
  • cosmetic adjuvants conventionally used in such preparations, for example preservatives, bactericides, perfumes, foaming inhibitors, colorants, pigments having a coloring effect, thickeners, surface-active substances, emulsifiers, softening, moisturizing and / or moisturizing substances, fats, oils, waxes or other customary constituents of a cosmetic or dermatological formulation, such as alcohols, polyols, poly
  • Oils such as triglycerides of capric or caprylic acid, further natural oils such as e.g. Castor oil;
  • Fats, waxes and other natural and synthetic fats preferably esters of fatty acids with lower C-number alcohols, e.g. with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids of low C number or with fatty acids;
  • Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiloxanes and mixed forms thereof.
  • the oil phase of the emulsions, oleogels or hydrodispersions or lipodispersions in the context of the present invention is advantageously selected from the group of esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids having a chain length of 3 to 30 carbon atoms and saturated and / or or unsaturated, branched and / or unbranched alcohols having a chain length of from 3 to 30 carbon atoms, from the group consisting of esters of aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols having a chain length of from 3 to 30 carbon atoms. atoms.
  • ester oils can then advantageously be selected from the group isopropyl myristate, isopropyl palmitate, isopropyl steate, isopropyl oleate, n-butyl stearate, n-hexyl laurate, n-decyl oleate, isooctyl stearate, isononyl stearate, isononyl isononanoate, 2-ethylhexyl palmitate, 2-ethylhexyl laurate, 2-hexyldecyl stearate, 2-octyl dodecyl palmitate, oleyl oleate, oleyl erucate, erucyl oleate, erucyl erucate and synthetic, semi-synthetic and natural mixtures of such esters, for example jojoba oil.
  • the aqueous phase of the preparations according to the invention optionally contains advantageously humectants such as propylene glycol or panthenol, and in particular one or more thickeners which can be advantageously selected from the group silicon dioxide, aluminum silicates, hydroxypropylmethylcellulose, particularly advantageously a polyacrylate such as Carbopols type 980, each individually or in combination.
  • advantageously humectants such as propylene glycol or panthenol
  • thickeners which can be advantageously selected from the group silicon dioxide, aluminum silicates, hydroxypropylmethylcellulose, particularly advantageously a polyacrylate such as Carbopols type 980, each individually or in combination.
  • Emulsions of the invention are advantageous and contain e.g. the said fats, oils, waxes and other fatty substances, as well as water and an emulsifier, as commonly used for such a type of formulation.
  • Gels according to the invention usually contain low C number alcohols, e.g. Ethanol, propylene glycol, and water or an abovementioned oil in the presence of a thickener, which is preferably silica or an aluminum silicate in the case of oily-alcoholic gels, preferably a polyacrylate in the case of aqueous-alcoholic or alcoholic gels.
  • a thickener which is preferably silica or an aluminum silicate in the case of oily-alcoholic gels, preferably a polyacrylate in the case of aqueous-alcoholic or alcoholic gels.
  • Suitable propellants for preparations which can be sprayed from aerosol containers according to the invention are the customary known highly volatile, liquefied propellants, for example hydrocarbons (propane, butane, isobutane), which can be used alone or mixed with one another. Also, compressed air is advantageous to use.
  • preparations according to the invention may also contain substances which absorb UV radiation in the UVB range, the total amount of filter substances being e.g.
  • the preparation contains UV filter selected from the group of compounds phenylene-1, 4-bis (2-benzimidazyl) -3,3'-5,5'-tetrasulfonklaresalze; 2-phenylbenzimidazole-5-sulfonic acid salts; 1,4-di (2-oxo-10-sulfo-3-bomylidenemethyl) benzene and its salts; 4- (2-oxo-3-bornylidenemethyl) benzenesulfonic acid; 2-methyl-5- (2-oxo-3-bornylidenemethyl) sulfonic acid salts; 2- (2H-Benzotriazol-2-yl) -4-methyl-6- [2-methyl-3- [1,3,3,3-tetra-methyl-1 - [(trimethylsilyl) oxy] disiloxanyl] propyl] -phenol; 3- (4-methylbenzylidene) camphor; 3 benzylidenecamphor; ethy
  • the preparation contains no 3- (4-methylbenzylidene) - camphor and 2-hydroxy-4-methoxybenzophenone (INCI: oxybenzone), that is free of these ingredients.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne des préparations cosmétiques ou dermatologiques contenant au moins un dérivé de biphénylamine, et l'utilisation d'au moins un dérivé de biphénylamine pour la production de préparations cosmétiques pour le bronzage de la peau.
PCT/EP2014/077887 2014-02-19 2014-12-16 Préparations cosmétiques ou dermatologiques contenant au moins un dérivé de biphénylamine et utilisation d'au moins un dérivé de biphénylamine pour le bronzage de la peau WO2015124233A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102014203011.0 2014-02-19
DE102014203011.0A DE102014203011A1 (de) 2014-02-19 2014-02-19 Kosmetische oder dermatologische Zubereitungen mit einem Gehalt an einem oder mehreren Biphenylamin-Derivaten und Verwendung von einem oder mehreren Biphenylamin-Derivaten zur Bräunung der Haut

Publications (1)

Publication Number Publication Date
WO2015124233A1 true WO2015124233A1 (fr) 2015-08-27

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DE (1) DE102014203011A1 (fr)
WO (1) WO2015124233A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108863850A (zh) * 2017-02-09 2018-11-23 复旦大学 联芳基类化合物及其制备方法和用途
US10485745B2 (en) 2016-04-29 2019-11-26 L'oreal UV-A/UV-B sunscreen composition
JP2020508981A (ja) * 2017-02-09 2020-03-26 ▲復▼旦大学Ｆｕｎｄａｎ Ｕｎｉｖｅｒｓｉｔｙ ビアリール化合物、その製造方法及び用途
US11583480B2 (en) 2019-08-27 2023-02-21 L'oreal Sunscreen composition with a high UV filter load

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1023859B (de) * 1955-08-22 1958-02-06 Gen Aniline & Film Corp Ultraviolett-Absorptionsmittel
US4293193A (en) * 1979-08-15 1981-10-06 Temple University Amine-substituted liquid crystal compositions
US6946489B2 (en) * 2000-03-24 2005-09-20 Merck Patent Gmbh Substituted biphenyl derivatives
US20080253978A1 (en) * 2005-06-03 2008-10-16 Isdin, S.A. Derivatives of Pyrrolyltriazine Together with Methods for Obtaining Them and Their Use as Protecting Agents Uv Radiation
WO2008134712A2 (fr) * 2007-04-30 2008-11-06 Living Proof, Inc. Utilisation d'inhibiteurs de la métalloprotéinase de la matrice pour les soins de la peau
US20110020251A1 (en) * 2009-07-27 2011-01-27 Shih Jenn S Ultraviolet-Absorbing Compounds
US8623871B2 (en) * 2006-01-25 2014-01-07 Synta Pharmaceuticals Corp. Substituted biaryl compounds for inflammation and immune-related uses
DE102012215501A1 (de) * 2012-08-31 2014-03-06 Beiersdorf Ag Kosmetische oder dermatologische Zubereitungen mit einem Gehalt an einem oder mehreren Biphenylamin-Derivaten und Verwendung von einem oder mehreren Biphenylamin-Derivaten zur Herstellung kosmetischer Zubereitungen zur Bräunung der Haut

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1023859B (de) * 1955-08-22 1958-02-06 Gen Aniline & Film Corp Ultraviolett-Absorptionsmittel
US4293193A (en) * 1979-08-15 1981-10-06 Temple University Amine-substituted liquid crystal compositions
US6946489B2 (en) * 2000-03-24 2005-09-20 Merck Patent Gmbh Substituted biphenyl derivatives
US20080253978A1 (en) * 2005-06-03 2008-10-16 Isdin, S.A. Derivatives of Pyrrolyltriazine Together with Methods for Obtaining Them and Their Use as Protecting Agents Uv Radiation
US8623871B2 (en) * 2006-01-25 2014-01-07 Synta Pharmaceuticals Corp. Substituted biaryl compounds for inflammation and immune-related uses
WO2008134712A2 (fr) * 2007-04-30 2008-11-06 Living Proof, Inc. Utilisation d'inhibiteurs de la métalloprotéinase de la matrice pour les soins de la peau
US20110020251A1 (en) * 2009-07-27 2011-01-27 Shih Jenn S Ultraviolet-Absorbing Compounds
DE102012215501A1 (de) * 2012-08-31 2014-03-06 Beiersdorf Ag Kosmetische oder dermatologische Zubereitungen mit einem Gehalt an einem oder mehreren Biphenylamin-Derivaten und Verwendung von einem oder mehreren Biphenylamin-Derivaten zur Herstellung kosmetischer Zubereitungen zur Bräunung der Haut

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
J N BAXTER ET AL: "The Infrared Spectra of Some Sulphonamides.", JOURNAL OF THE CHEMICAL SOCIETY, 1 January 1955 (1955-01-01), pages 669 - 679, XP055174432, Retrieved from the Internet <URL:http://pubs.rsc.org/en/content/articlepdf/1955/jr/jr9550000669> [retrieved on 20150306] *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10485745B2 (en) 2016-04-29 2019-11-26 L'oreal UV-A/UV-B sunscreen composition
CN108863850A (zh) * 2017-02-09 2018-11-23 复旦大学 联芳基类化合物及其制备方法和用途
JP2020508981A (ja) * 2017-02-09 2020-03-26 ▲復▼旦大学Ｆｕｎｄａｎ Ｕｎｉｖｅｒｓｉｔｙ ビアリール化合物、その製造方法及び用途
US11583480B2 (en) 2019-08-27 2023-02-21 L'oreal Sunscreen composition with a high UV filter load

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