WO2007135197A2 - Utilisation de benzophénone-4 et de ses sels pour éteindre la fluorescence du phényl-dibenzimidazole-tétrasulfonate disodique - Google Patents

Utilisation de benzophénone-4 et de ses sels pour éteindre la fluorescence du phényl-dibenzimidazole-tétrasulfonate disodique Download PDF

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Publication number
WO2007135197A2
WO2007135197A2 PCT/EP2007/056997 EP2007056997W WO2007135197A2 WO 2007135197 A2 WO2007135197 A2 WO 2007135197A2 EP 2007056997 W EP2007056997 W EP 2007056997W WO 2007135197 A2 WO2007135197 A2 WO 2007135197A2
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Prior art keywords
acid
salts
benzophenone
disodium phenyl
phenyl dibenzimidazole
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WO2007135197A3 (fr
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William Johncock
Jürgen Claus
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Symrise AG
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Symrise AG
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles

Definitions

  • the present invention relates to cosmetic preparations for protection of the human skin and human hair against the harmful effects of ultraviolet solar radiation containing the water soluble UVA absorbing substance disodium phenyl dibenzimidazole tetrasulfonate [2,2'-(1 ,4-Phenylene)bis(1 H-benzimidazole-4,6- disulfonic acid, monosodium salt); 1 H-Benzimidazole-4,6-Disulfonic Acid, 2,2'- (1 ,4-Phenylene)Bis-, Disodium Salt] together with Benzophenone-4 (2-Hydroxy- 4-methoxybenzophenone-5-sulfonic acid) and its salts to quench the fluorescence of disodium phenyl dibenzimidazole tetrasulfonate.
  • disodium phenyl dibenzimidazole tetrasulfonic acid no differentiation is made between disodium phenyl dibenzimidazole tetrasulfonic acid and any salts thereof, unless otherwise indicated.
  • disodium phenyl dibenzimidazole tetrasulfonate, its salts and disodium phenyl dibenzimidazole tetrasulfonic acid and its salts are used interchangeably unless otherwise indicated.
  • UV absorbers are compounds which have a pronounced absorption capacity for ultraviolet radiation. They are used in particular as sunscreens in cosmetic and pharmaceutical preparations, but also to improve the light fastness of industrial products, such as paints, varnishes, plastics, textiles, polymers such as, for example, polymers and copolymers of mono- and diolefins, polystyrenes, poly- urethanes, polyamides, polyesters, polyureas and polycarbonates, packaging materials and rubbers.
  • UV rays are classified according to wavelength as UVA rays (320-400 nm, UVA-I: 340-400 nm, UVA-II: 320-340 nm) or UVB rays (280-320 nm).
  • UV rays can cause acute and chronic damage to the skin, the type of damage depending on the wavelength of the radiation. For instance, UVB radiation can cause sunburn (erythema) extending to most severe burning of the skin; reduction in enzyme activities, weakening of the immune system, disturbances of the DNA structure and changes in the cell membrane are also known as harmful effects of UVB rays.
  • UVA rays penetrate into deeper layers of the skin where they can acceler- ate the aging process of the skin.
  • UVA-II radiation additionally contributes to the development of sunburn.
  • UVA radiation can trigger phototoxic or photoallergy skin reactions.
  • Very frequent and unprotected irradiation of the skin by sunlight leads to a loss of skin elasticity and to increased development of wrinkles. In extreme cases, pathogenic changes in the skin extend- ing to skin cancer are observed.
  • materials which absorb or reflect UV light generally called UV absorbers, are used in cosmetic or pharamacological preparations.
  • the UV absorbers are classified as UVA and UVB absorbers depending on the location of their absorption maxima; if a UV absorber absorbs both UVA and UVB, it is referred to as a UVA/B broadband absorber.
  • UVA absorbers The number of suitable UVA absorbers is very limited and they have considerable deficiencies.
  • the filter 4-tert.-butyl-4'-methoxy-dibenzoylmethane (Butyl methoxydibenzoylmethane; absorption maximum at 357 nm) that is fre- quently used in particular for protection against UVA I radiation is not photosta- ble.
  • Photoreactions are also observed in combination with the UVB filters 2- ethylhexyl and isoamyl p-methoxycinnamate.
  • it has only a limited solubility in cosmetic oils, which can lead to problems in the formulation of cos- metic preparations.
  • sunscreen products containing dibenzoyl- methane derivatives can leave marks on textiles that are extremely difficult to wash out.
  • a relatively novel UVA filter that does not have these disadvantages is disodium phenyl dibenzimidazole tetrasulfonate sold under the trade name of Neo Heliopan® AP (e.g. EP 669 323, WO 03/084496; Symrise GmbH & Co. KG, Germany).
  • Neo Heliopan® AP e.g. EP 669 323, WO 03/084496; Symrise GmbH & Co. KG, Germany.
  • This very photostable UVA filter harmlessly dissipates its absorbed UV energy via fluorescence/phosphorescence which by a small number of con- sumers is regarded as a negative. There is therefore a need for agents to quench this fluorescence for use in cosmetic and pharmaceutical preparations.
  • quenching of fluorescence can occur by a number of mechanisms including self quenching when high concentrations of the substance are present; static quenching which occurs from a complex formed by the ground state of the fluorescor and the quencher; and colour quenching in which coloured molecules absorb the emitted fluorescence energy.
  • Typical quenchers include oxygen, but singlet oxygen is produced as a result and so is undesirable in cosmetics and pharmaceutical preparations; heavy metals such as thallium, or certain organic compounds such as alkyl bromide/fluoride/chlorides, tetrafluoroborates, anthra- cene derivatives, could in principle be used but are toxic and so are of no use in cosmetics and pharmaceutical preparations; and colours, which will give an unacceptable colour to cosmetics and pharmaceutical preparations.
  • Additional possible quenchers are water soluble plant extracts which contain UV and visible light absorbing chromophors such as but not restricted to Green Tea, Rooibos, Sophora japonica, or the UV absorbing materials that are found in the plant extracts such as rutin, riboflavins, tannins, nictinamides, quercetin, ubiquinones, polyphenols etc, or their derivatives.
  • UV absorbing materials that are found in the plant extracts such as rutin, riboflavins, tannins, nictinamides, quercetin, ubiquinones, polyphenols etc, or their derivatives.
  • these materials are either unstable in cosmetic preparations on storage or can lead to unacceptable colouration of the preparations.
  • the UV absorbing substance Benzophenone-4 (2-Hydroxy-4- methoxybenzophenone-5-sulfonic acid) and its salts absorbs strongly in the UVB wavelength with a lambda maximum of 286 nm and a molar extinction coefficient - A -
  • a preparation comprising disodium phenyl dibenzimidazole tetrasulfonic acid and/or one or more salts thereof, further comprising benzophenone-4 and/or one or more salts thereof, in an amount sufficient to reduce the fluorescence of disodium phenyl dibenzimidazole tetrasulfonic acid and, if present, its respective salt(s).
  • the preparation is a cosmetic or pharmaceutical, especially dermatological, preparation.
  • the molar ratio of the total of benzophenone-4 and its salts to the total amount of disodium phenyl dibenzimidazole tetrasulfonic acid and its salts is in the range from 0.1 : 5.0 to 5.0 : 0.1 , more preferably in the range 0.3 : 3.0 to 3.0 : 0.3 and most preferably in the range 0.4 : 2.0 to 2.0 :0.5.
  • the preparation (particularly a cosmetic and/or pharmaceutical preparation) comprises Benzophenone-4 and/or any of its salts and disodium phenyl dibenzimidazole tetrasulfonate and/or one or more salts thereof in combination with one or more further UV absorbers, such that the total fraction of UV absorbers is in the range from 0.1% to 40% by weight, more preferably in the range from 0.2% to 30% by weight and more preferably in the range 0.5% to 20% by weight, based on the total weight of the preparation.
  • a (cosmetic and/or derma- tological/pharmaceutical) preparation comprises a total amount of UV filters and/or inorganic pigments such that the preparation of the invention has a sun protection factor of greater than or equal to 2 (preferably greater than or equal to 5). These sunscreens are suitable for protecting skin and hair.
  • UV absorbers are, for example, organic UV absorbers from the class of 4-aminobenzoic acid and derivatives, salicylic acid derivatives, benzophenone derivatives, dibenzoylmethane derivatives, di- phenylacrylates, 3-imidazol-4-ylacrylic acid and its esters, benzofuran derivatives, benzylidenemalonate derivatives, polymeric UV absorbers containing one or more organosilicon radicals, cinnamic acid derivatives, camphor derivatives, trianilino-s-triazine derivatives, 2-hydroxyphenylbenzotriazole derivatives, phenyl, menthyl anthranilate, benzotriazole derivatives, indole derivatives.
  • organic UV absorbers from the class of 4-aminobenzoic acid and derivatives, salicylic acid derivatives, benzophenone derivatives, dibenzoylmethane derivatives, di- phenylacrylates, 3-imidazol-4-yl
  • UV absorbers specified below which can be used additionally for the purposes of the present invention, are preferred, but of course are not limiting.
  • Such preferred UV filters are as follows:
  • UVB filters such as, for example:
  • menthyl anthranilate (Neo Heliopan ® MA)
  • Broadband filters such as, for example:
  • UVA filters such as, for example:
  • UV absorbers particularly suitable for combination are as follows:
  • menthyl anthranilate (Neo Heliopan ® MA)
  • particulate UV filters or inorganic pigments which if desired may have been rendered hydrophobic, such as the oxides of titanium (TiO 2 ), of zinc (ZnO), of iron (Fe 2 O 3 ), of zirconium (ZrO 2 ), of silicon (SiO 2 ), of manganese (z.B. MnO), of aluminium (AI 2 O 3 ), of cerium (e.g. Ce 2 O 3 ) and/or mixtures.
  • Mexoryl ® SX and its salts used in the cosmetic or dermatological formulation containing Benzophenone-4 and/or any of its salts and disodium phenyl dibenzimidazole tetrasulfonate is in the range of 0.1 to 10.0%, preferably in the range from 0.3 to 8% and most preferably in the range from 0.5 to 5.0% of the total formulation.
  • the total amount of oil soluble UV filters that may be used in a cosmetic or dermatological formulation containing Benzophenone-4 or its salts, and disodium phenyl dibenzimidazole tetrasulfonate, for example but not limited to (2- ethylhexyl) 4,4 ' ,4 " -(1 ,3,5-triazine-2,4,6-triyltriimino)tribenzoate and /or -tert-butyl- 4'-methoxydibenzoylmethane, and / or 2-ethylhexyl 4-dimethylaminobenzoate, and / or Mexoryl ® XL and/or Uvasorb ® HEB and/or Tinosorb ® S and/or Benzophe- none-3 and/or Parsol ® SLX and/or Neo Heliopan ® MA, and /or isoamyl p- methoxycinnamate, and/or 2-
  • Ethylhexyl methoxycinnamate used in the cosmetic or derma- tological formulation Benzophenone-4 and/or any of its salts and disodium phenyl dibenzimidazole tetrasulfonate is in the range of 0.1 to 20.0%, preferably in the range from 0.3 to 15% and most preferably in the range from 0.5 to 10.0% of the total formulation.
  • the amount of lsoamyl p-methoxycinnamate used in the cosmetic or derma- tological formulation containing Benzophenone-4 and/or any of its salts and disodium phenyl dibenzimidazole tetrasulfonate is in the range of 0.1 to 20.0%, preferably in the range from 0.3 to 15% and most preferably in the range from 0.5 to 10.0% of the total formulation.
  • the amount of Octocrylene used in the cosmetic or dermatological formulation containing Benzophenone-4 and/or any of its salts and disodium phenyl dibenzimidazole tetrasulfonate is in the range of 0.1 to 20.0%, preferably in the range from 0.3 to 15% and most preferably in the range from 0.5 to 10.0% of the total formulation.
  • the amount of salicylate esters used in the cosmetic or dermatological formulation containing Benzophenone-4 and/or any of its salts and disodium phenyl dibenzimidazole tetrasulfonate is in the range of 0.1 to 20.0%, preferably in the range from 0.3 to 15% and most preferably in the range from 0.5 to 10.0% of the total formulation.
  • Ethylhexyl salicylate is chosen as the UV filter, it is ad- vantageous that its total amount ranges from 0.1 to 5.0% of the formulation and when Homosalate is chosen as the UV filter it is advantageous that its total amount ranges from 0.1 to 15.0% of the formulation
  • the amount of Butyl methoxydibenzoylmethane used in the cosmetic or derma- tological formulation containing Benzophenone-4 and/or any of its salts and disodium phenyl dibenzimidazole tetrasulfonate is in the range of 0.1 to 10.0%, preferably in the range from 0.3 to 7.0% and most preferably in the range from 0.5 to 5.0% of the total formulation.
  • the amount of Uvinul ® A Plus used in the cosmetic or dermatological formulation containing Benzophenone-4 and/or any of its salts and disodium phenyl dibenzimidazole tetrasulfonate is in the range of 0.1 to 10.0%, preferably in the range from 0.3 to 7.0% and most preferably in the range from 0.5 to 5.0% of the total formulation.
  • the amount of Tinosorb ® S used in the cosmetic or dermatological formulation containing Benzophenone-4 and/or any of its salts and disodium phenyl diben- zimidazole tetrasulfonate is in the range of 0.1 to 10.0%, preferably in the range from 0.3 to 7.0% and most preferably in the range from 0.5 to 5.0% of the total formulation.
  • the amount of Uvasorb ® HEB used in the cosmetic or dermatological formulation containing Benzophenone-4 and/or any of its salts and disodium phenyl dibenzimidazole tetrasulfonate is in the range of 0.1 to 10.0%, preferably in the range from 0.3 to 7.0% and most preferably in the range from 0.5 to 5.0% of the total formulation.
  • the amount of Uvinul ® T-150 used in the cosmetic or dermatological formulation containing Benzophenone-4 and/or any of its salts and disodium phenyl dibenzimidazole tetrasulfonate is in the range of 0.1 to 10.0%, preferably in the range from 0.3 to 7.0% and most preferably in the range from 0.5 to 5.0% of the total formulation.
  • the total amount of oil microfine organic and/or inorganic pigments for example but not limited to triazine derivatives and/or Zinc Oxide (coated and un-coated), and/or titanium dioxide (coated or un-coated) that may be used in a cosmetic or dermatological formulation containing Benzophenone-4 and/or any of its salts and disodium phenyl dibenzimidazole tetrasulfonate is in the range of 0.1 to
  • UV filter it is advantageous that its total amount ranges from 0.1% to 10.0% of the formulation and when one or more triazine organic pigment(s) are chosen it is advantageous that its total amount ranges from 0.1% to 10.0% of the formulation.
  • UV filters for example with the UV filters listed above and particularly with the UV filters listed as "particularly suitable for combination", but not limited to these, leads to synergistic effects in the degree of protection offered against UVB and UVA radiation as determined by measurements to determine sun protection factors against UVA and / or UVB radiation.
  • the invention thus also provides the teaching that combining (a) Benzophenone- 4 or any of its salts and (b) disodium phenyl dibenzimidazole tetrasulfonic acid or any of its salts with individual or any desired mixtures of any of the UV filters listed above as well as any from the allowed UV filters for use in sun protection products legislated in : USA: by the Food and Drug Administration (FDA). published in the Monograph for Sunscreen Drug Products for Over-The-Counter Human Use.
  • FDA Food and Drug Administration
  • benzophenone-4 absorbs UV radiation, when it is used in combination with disodium phenyl diben- zimidazole tetrasulfonate it also leads to photostabilisation of UV absorbers of lower stability to UV such as derivatives of butyl methoxydibenzoylmethane.
  • benzophenone-4 and its salts together with disodium phenyl diben- zimidazole tetrasulfonate or its acid form give rise to stabilisation of the UVA absorber 4-tert.-butyl-4'-methoxydibenzoylmethane, which is highly unstable to light.
  • UV absorbers such as, for example, methylbenzylidene- camphor, 2-ethylhexyl-2-cyano-3,3'-diphenylacrylate, octyltriazone,
  • UVA absorbers especially UVA-I absorbers
  • a combination of Benzophenone-4 and/or any of its salts and disodium phenyl dibenzimidazole tetrasulfon ic acid and/or any of its salts together with butyl methoxydibenzoylmethane, or Tinosorb S or indanylidene derivatives or Benzoylcinnamyl nitriles (UVA-I absorbers) is to be mentioned in particular for broad UV protection.
  • UVA filters that are preferred to be used in combination with both of Benzophenone-4 and/or any of its salts and disodium phenyl dibenzimidazole tetrasulfon ic acid and/or any of its salts, on their own or in combination, are Mexoryl SX, Mexoryl ® XL, Tinosorb ® M, Tinosorb ® S, Benzophenone-3, Uvinul ® A Plus, Neo Heliopan ® 357 and Neo Heliopan ® MA.
  • the abovementioned combinations can be combined with all UVB filters and mixtures of these filters (cf. the above mentioned particularly suitable UV (sic) absorbers) for optimum broadband protection against UVA and UVB radiation.
  • Neo Heliopan ® AV, Neo Heliopan ® E1000, Neo Heliopan ® Hydro, Neo Heliopan ® MBC, Neo Heliopan ® 303, Neo Heliopan ® OS, Neo Heliopan ® HMS, Uvinul ® T150, Uvasorb ® HEB, Parsol ® SLX are particularly suitable UVB filters.
  • Cosmetic and dermatological preparations in the sense of this invention contain one or more conventional UVA, UVB and/or broadband filters as single substances or in arbitrary mixtures with one another in the lipid phase and/or in the aqueous phase. They are satisfactory products in every respect which, surprisingly are distinguished by high UVA protection and a high UVB protection factor.
  • UV absorbers leave marks on articles of clothing that can no longer be washed out.
  • the UVA absorber tert.-butyl- methoxydibenzoylmethane is known to produce marks on textiles that can no longer be washed out.
  • the use of a of Benzophenone-4 and/or any of its salts and disodium phenyl dibenzimidazole tetrasulfonate according to the invention do not have this disadvantage since any marks formed on textiles can be washed out very readily.
  • the (cosmetic and/or pharmaceutical/dermatological) preparations according to the invention can be formulated in the customary manner and serve as cosmetic and/or dermatological sunscreens and also for the treatment, care and cleansing of the skin and/or the hair and as a make-up product in decorative cosmetics.
  • cosmetic and pharmaceutical preparations serving for protection of skin and hair against UV radiation can be in the use forms conventionally used, i.e. in the form of oil-in-water, water-in-oil or mixed emulsion, in the form of milk, in the form of lotion or cream, aerosol, hydrodispersion gel or oil gel (emulsifier-free), spray, foam, solution, powder, pencil preparation or in the form of any other customary cosmetic or pharmaceutical formulation.
  • Preparations such as sham- poo, rinse, conditioner, gel, lotion, spray or cream are preferably used for protection of the hair against UV rays.
  • the (cosmetic and/or pharmaceutical/dermatological) preparations according to the present invention can have the customary composition and can be used for cosmetic and/or dermatological sun protection, and also for the treatment, care and cleansing of the skin and/or of the hair and as a make-up product in decorative cosmetics.
  • the preparations according to the present invention can, depending on their formulation, be used, for example, as skin protection cream, cleansing milk, sunscreen lotion, nourishing cream, day cream or night cream.
  • the preparations according to the present invention can, depending on their formulation, also be used for example, in hair care compositions such as shampoos, conditioners, 2 in 1 preparations, anti-dandruff shampoos, hair tonics, hair lotions, hair rinses, styling products, sprays, etc.
  • preparations according to the present invention are bases for pharmaceutical preparations. Preference is given, in particular, to those cosmetic and dermatological preparations in the form of a skin care, hair care or make-up product. Typical embodiments are creams, gels e.g.
  • hydrogels but not limited to hydrogels, hydrodispersion gels, oil gels; lotions, alcoholic and aqueous/alcoholic solutions, emulsions in their various forms for example but not limited to oil in water (O/W), water in oil (W/O), mixed emulsions, PIT emulsions, Pickering emulsions, microemulsions, nano-emulsions; aerosol foams, non- aerosol foams, aerosols sprays, non-aerosol sprays, pump sprays, serums, roll- ons, pastes, balsams, or stick preparations.
  • O/W oil in water
  • W/O water in oil
  • mixed emulsions PIT emulsions
  • aerosol foams non- aerosol foams, aerosols sprays, non-aerosol sprays, pump sprays, serums, roll- ons, pastes, balsams, or stick preparations.
  • compositions may also comprise, as further auxiliaries and additives, mild surfactants, co-emulsifiers, super- fatting agents, pearlescent waxes, bodying agents, thickeners, polymers, silicone compounds, fats, waxes, stabilizers, biogenic active ingredients, deodorant active ingredients, antidandruff agents, film formers, swelling agents, hydrotropic agents, preservatives, insect repellants, tanning agents, artificial self-tanning agents (e.g. dihydroxyacetone), stabilizers, perfume oils, dyes, antimicrobial agents, aqueous and non-aqueous plant extracts and the like.
  • mild surfactants e.g. dihydroxyacetone
  • co-emulsifiers emulsifiers
  • super- fatting agents e.g., pearlescent waxes, bodying agents, thickeners, polymers, silicone compounds, fats, waxes, stabilizers, biogenic active ingredients, deodorant active ingredients, antidandruff agents, film formers, swelling
  • the cosmetic and dermatological preparations according to the present invention are applied to the skin and/or the hair in a sufficient amount in the manner customary for cosmetics or pharmacological and dermatological preparations.
  • cosmetic and dermatological preparations in the form of a cosmetic composition for the protection of the skin and hair.
  • these can contain at least one inorganic pigment, preferably an inorganic mi- cropigment.
  • Benzophenone-4 and/or any of its salts and disodium phenyl dibenzimidazole tetrasulfonate used according to the present invention can contain at least one inorganic pigment, preferably an inorganic mi- cropigment.
  • Those cosmetic and dermatological preparations that are in the form of a skin care or make-up product are particularly preferred.
  • the cosmetic and dermatological preparations according to the present invention can comprise cosmetic auxiliaries, as are customarily used in such preparations, e.g. preservatives, bactericides, perfumes, antifoams, dyes, pigments which have a coloring action, thickeners, moisturizers and/or humectants, 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 auxiliaries e.g. preservatives, bactericides, perfumes, antifoams, dyes, pigments which have a coloring action, thickeners, moisturizers and/or humectants, 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.
  • Preferred embodiments of the cosmetic and/or pharmaceutical, especially de- rmatological preparations of the invention may also comprise anionic, cationic, nonionic and/or amphoteric surfactants.
  • Surfactants are amphiphilic substances which can dissolve organic, nonpolar substances in water.
  • the hydrophilic components of a surfactant molecule are usually polar functional groups, for example -COO ' , -OSO 3 2' , -SO 3 " , while the hydrophobic parts as a rule are nonpolar hydrocarbon radicals.
  • Surfactants are in general classified accord- ing to the nature and charge of the hydrophilic molecular moiety. A distinction can be made between four groups here:
  • Anionic surfactants as a rule contain carboxylate, sulphate or sulphonate groups as functional groups. In aqueous solution, they form negatively charged organic ions in an acid or neutral medium. Cationic surfactants are almost exclusively characterized by the presence of a quaternary ammonium group. In aqueous solution, they form positively charged organic ions in an acid or neutral medium. Amphoteric surfactants contain both anionic and cationic groups and accordingly behave like anionic or cationic surfactants in aqueous solution, depending on the pH. In a strongly acid medium they have a positive charge, and in an alkaline medium a negative charge. On the other hand, they are zwitterionic in the neutral pH range. Polyether chains are typical of nonionic surfactants. Nonionic surfactants do not form ions in an aqueous medium.
  • Anionic surfactants which are advantageously used are acylamino acids (and salts thereof), such as:
  • acyl glutamates for example sodium acyl glutamate, di-TEA-palmitoyl aspartate and sodium caprylic/capric glutamate
  • - acyl peptides for example palmitoyl hydrolysed milk protein, sodium cocoyl hydrolysed soya protein and sodium/potassium cocoyl hydrolysed collagen
  • sarcosinates for example myristoyl sarcosine, TEA-lauroyl sarcosinate, sodium lauroyl sarcosinate and sodium cocoyl sarcosinate,
  • taurates for example sodium lauroyl taurate and sodium methylcocoyl taurate
  • TEA stearate Glyceryl stearates
  • ester-carboxylic acids for example calcium stearoyl lactylate, laureth-6 citrate and sodium PEG-4 lauramide carboxylate, glyceryl stearates, glyceryl- oleylstearates, glyceryl citrates, glyceryl oleyl citrates,
  • Glucoside esters such as for example
  • cetearyl glucoside, lauryl glucoside phosphoric acid esters and salts such as, for example :
  • cetyl phosphate (mono, di cetyl and their mixtures), Potassium cetyl phosphate, (mono, di cetyl and their mixtures), DEA cetyl phosphate (mono, di cetyl and their mixtures), DEA -oleth-10 phosphate and dilaureth-4 phos- phate,
  • acyl isethionates e.g. sodium/ammonium cocoyl isethionate
  • alkylsulphonates for example sodium coco-monoglyceride sulphate, so- dium C12-14 olefinsulphonate, sodium lauryl sulphoacetate and magnesium PEG-3 cocamide sulphate,
  • sulphosuccinates for example dioctyl sodium sulphosuccinate, disodium laureth-sulphosuccinate, disodium laurylsulphosuccinate and disodium un- decylenamido-MEA-sulphosuccinate
  • sulphuric acid esters such as:
  • alkyl ether sulphate for example sodium, ammonium, magnesium, MIPA, TIPA laureth sulphate, sodium myreth sulphate and sodium C12-13 pareth sulphate,
  • alkyl sulphates for example sodium, ammonium and TEA lauryl sulphate.
  • alkylamines alkylimidazoles
  • B + any desired cation, e.g. Na + and
  • Quaternary surfactants contain at least one N atom which is covalently bonded to 4 alkyl or aryl groups. This leads to a positive charge, independently of the pH. Alkylbetaine, alkylamidopropylbetaine and alkylamidopropylhydroxysulphaine are advantageous.
  • the cationic surfactants used can further preferably be chosen from the group consisting of quaternary ammonium compounds, in particular benzyltrialkylammonium chlorides or bromides, such as, for example, benzyldi- methylstearylammonium chloride, and also alkyltrialkylammonium salts, for example cetyltrimethylammonium chloride or bromide, alkyldimethyl- hydroxyethylammonium chlorides or bromides, dialkyldimethylammonium chlorides or bromides, alkylamideethyltrimethylammonium ether sulphates, al- kylpyridinium salts, for example lauryl- or cetylpyridinium chloride, imidazoline derivatives and compounds having a cationic character, such as amine oxides, for example alkyldimethylamine oxides or alkylaminoethyldimethylamine oxides. Cetyltrimethyl-ammonium salt
  • acyl/dialkylethylenediamine for example sodium acylamphoacetate, diso- dium acylamphodipropionate, disodium alkylamphodiacetate, sodium acylamphohydroxypropylsulphonate, disodium acylamphodiacetate and sodium acylamphopropionate, N-alkylamino acids, for example aminopropyl alkylglutamide, alkyl- aminopropionic acid, sodium alkylimidodipropionate and lauroampho- carboxyglycinate. acylamphohydroxypropylsulphonate, disodium acylamphodiacetate and sodium acylamphopropionate,
  • N-alkylamino acids for example aminopropyl alkylglutamide, alkyl- aminopropionic acid, sodium alkylimidodipropionate and lauroampho- carboxyglycinate.
  • alkanolamides such as cocamides MEA/DEA/MIPA
  • amine oxides such as cocoamidopropylamine oxide
  • - ethers for example ethoxylated/propoxylated alcohols, ethoxy- lated/propoxylated esters, ethoxylated/propoxylated glycerol esters, ethoxylated/propoxylated cholesterols, ethoxylated/propoxylated triglyceride esters, ethoxylated/propoxylated lanolin, ethoxylated/propoxylated polysi- loxanes, propoxylated POE ethers and alkyl polyglycosides, such as lauryl glucoside, decyl glucoside and coco-glycoside.
  • alkyl polyglycosides such as lauryl glucoside, decyl glucoside and coco-glycoside.
  • sucrose esters sucrose ethers
  • polyglycerol esters diglycerol esters, monoglycerol esters polyglyceryl-2 dipolyhydroxystearate (Dehymuls ® PGPH), polyglyceryl-3 diisostearate (Lameform ® TGI), polyglyceryl-4 isostearate (lsolan ® GI 34), polyglyceryl- 3 oleate, diisostearyl polyglyceryl-3 diisostearate (lsolan ® PDI), polyglyceryl-
  • anionic and/or amphoteric surfactants with one or more nonionic surfactants is further advantageous.
  • cosmetic and dermatological preparations advantageously, but not obligatorily, comprise inorganic pigments based on finely disperse metal oxides and/or other metal compounds which are insoluble or sparingly soluble in water, in particular the oxides of titanium (TiO 2 ), zinc (ZnO), iron (e.g. Fe 2 O 3 ), zirconium (ZrO 2 ), silicon (SiO 2 ), manganese (e.g. MnO), aluminum (AI 2 O 3 ), cerium (e.g. Ce 2 O 3 ), mixed oxides of the corresponding metals, and mixtures of such oxides.
  • These pigments are X-ray-amorphous or non-X-ray-amorphous.
  • X-ray-amorphous oxide pigments are metal oxides or semi-metal oxides which reveal no or no recognizable crystalline structure in X-ray diffraction experiments. Such pigments are often obtainable by flame reaction, for example by reacting a metal or semi-metal halide with hydrogen and air (or pure oxygen) in a flame.
  • X-ray-amorphous oxide pigments are used as thickeners and thixotropic agents, flow auxiliaries for emulsion and dispersion stabilization and as carrier substance (for example for increasing the volume of finely divided powders).
  • X-ray-amorphous oxide pigments which are known and often used in cosmetic or dermatological galenics are, for example, high-purity silicon oxide.
  • X- ray-amorphous silicon dioxide pigments with a particle size in the range from 5 to 40 nm and an active surface area (BET) in the range from 50 to 400 m 2 /g, preferably 150 to 300 m 2 /g, where the particles are to be regarded as spherical particles of very uniform dimension.
  • BET active surface area
  • the silicon dioxide pigments are recognizable as loose, white powders. Silicon dioxide pigments are sold com- suddenly under the name Aerosil ® (CAS-No. 7631 -85-9) or Carb-O-Sil
  • Aerosil ® grades are, for example, Aerosil ® 0X50, Aerosil ® 130, Aerosil ® 150, Aerosil ® 200, Aerosil ® 300, Aerosil ® 380, Aerosil ® MQX 80, Aerosil ® MOX 170, Aerosil ® COK 84, Aerosil ® R 202, Aerosil ® R 805, Aerosil ® R 812, Aerosil ® R 972, Aerosil ® R 974, Aerosil ® R976.
  • cosmetic or dermatological light protection preparations comprise 0.1 to 20% by weight, advantageously 0.5 to 10% by weight, more preferably 1 to 5% by weight, of X-ray-amorphous oxide pigments.
  • the non-X-ray-amorphous inorganic pigments are, according to the present invention, advantageously in hydrophobic form, i.e. have been surface-treated to repel water.
  • This surface treatment may involve providing the pigments with a thin hydrophobic layer by processes known per se. Such a process involves, for example, producing the hydrophobic surface layer by a reaction according to
  • n and m are stoichiometric parameters to be used as desired, and R and R' are the desired organic radicals.
  • Hydrophobicized pigments prepared analogously to DE-A 33 14 742, for example, are advantageous.
  • TiO 2 pigments as are sold under the trade name T805 from Degussa.
  • TiO 2 /Fe 2 O 3 mixed oxides as are supplied, for example, under the trade name T817, also from Degussa.
  • the total amount of inorganic pigments, in particular hydrophobic inorganic mi- cropigments, in the finished cosmetic or dermatological preparations is advantageously chosen from the range from 0.1 to 30% by weight, preferably 0.1 to 10.0% by weight, preferably 0.5 to 6.0% by weight, based on the total weight of the preparations.
  • An additional content of skin lightening ingredients in the cosmetic or derma- tological preparation is optional.
  • Such skin lightening ingredients which can be used are for example but not limited to the following : kojic acid (5-hydroxy-2- hydroxymethyl-4-pyranone), kojic acid derivatives such as for example kojic dipalmitate, arbutin, ascorbic acid, ascorbic acid derivatives, hydroquinone, hydroquinone derivatives, styryl resorcinol derivatives (e.g. 4-(1 -phenylethyl)1 ,3- benzenediol), molecules containing sulphur, such as glutathione or cysteine for example, alpha-hydroxy acids (e.g.
  • alpha-hydroxy fatty acids palmitic acid, phytic acid, lactoferrin, humic acid, gallic acid, bile extracts, bilirubin, biliverdin), retinoids, soja milk, soya extract, serine protease inhibitors or lipoic acid or other synthetic or natural active compounds for skin and hair lightening, these compounds also being used in the form of an extract from plants, such as bearberry extract, rice extract, papaya extract, liquorice root extract or constituents concentrated from these, such as glabridin or licochalcone A, Artocarpus extract, extract from Rumex and Ramulus species, extracts from pine species (Pinus) and extracts from Vitis species or stilbene derivatives concentrated from these, extract from saxifraga, mulberry, Scutelleria and/or grapes.
  • an extract from plants such as bearberry extract, rice extract, papaya extract, liquorice root extract or constituents concentrated from these, such as glabridin or licochalcone
  • antioxidants in the cosmetic or dermatological preparation are generally preferred. According to the present invention, favorable antioxidants which can be used are all antioxidants customary or suitable for cosmetic and/or dermatological applications.
  • the antioxidants are advantageously chosen from the group of amino acids (e.g. glycine, histidine, tyrosine, tryptophan) and derivatives thereof, imidazoles (e.g. urocanic acid) and derivatives thereof, peptides, such as D,L-carnosine, D- carnosine, L-carnosine and derivatives thereof (e.g. anserine), carotenoids, carotenes (e.g. ⁇ -carotene, ⁇ -carotene, lycopene) and derivatives thereof, chlorogenic acid and derivatives thereof, lipoic acid and derivatives thereof (e.g.
  • amino acids e.g. glycine, histidine, tyrosine, tryptophan
  • imidazoles e.g. urocanic acid
  • peptides such as D,L-carnosine, D- carnosine, L-carnosine and derivatives thereof (e.g. anserine)
  • thiore- doxin glutathione, cysteine, cystine, cystamine and the glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, ⁇ -linoleyl, cholesteryl and glyceryl esters thereof
  • salts thereof dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and derivatives thereof (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts), and sulfoximine compounds (e.g.
  • buthionine sulfoximines in very low tolerated doses (e.g. pmol to ⁇ mol/kg)
  • very low tolerated doses e.g. pmol to ⁇ mol/kg
  • metal chelating agents e.g. ⁇ -hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin
  • ⁇ -hydroxy acids e.g.
  • vitamin E acetate
  • vitamin A and derivatives vitamin A palmitate
  • coniferyl benzoate of benzoin resin rutinic acid and derivatives thereof, ⁇ -glycosylrutin, ferulic acid, furfurylideneglucitol, carnosine, butylhydroxy-toluene, butylhydroxyanisol, nordihydroguaiacic acid, nordihydroguaiaretic acid, trihy- droxybutyrophenone, uric acid and derivatives thereof, mannose and derivatives thereof, zinc and derivatives thereof (e.g. ZnO, ZnSO 4 ), selenium and derivatives thereof (e.g.
  • stilbenes and derivatives thereof e.g. stilbene oxide, trans-stilbene oxide
  • derivatives salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids
  • the amount of the above-mentioned antioxidants (one or more compounds) in the preparations is preferably 0.001 to 30% by weight, more preferably 0.05 to 20% by weight, and most preferably 1 to 10% by weight, based on the total weight of the preparation.
  • Preferred embodiments of the cosmetic and/or pharmaceutical, especially der- matologically active preparations of the invention may advantageously also com- prise vitamins and vitamin precursors, it being possible for all the vitamins and vitamin precursors which are suitable or usual for cosmetic and/or dermatological applications to be used.
  • vitamins and vitamin precursors such as tocopherols, vitamin A, niacin acid and niacinamide, further vitamins of the B complex, in particular biotin, and vitamin C and panthenol and derivatives thereof, in particular the esters and ethers of pan- thenol, and cationically derivatized panthenols, such as panthenol triacetate, panthenol monoethyl ether and the monoacetate thereof and cationic panthenol derivatives.
  • vitamin E and/or derivatives thereof represent the antioxidant(s)
  • vitamin A or vitamin A derivatives, or carotenes or derivatives thereof represent the antioxidants
  • Preferred embodiments of the cosmetic and/or pharmaceutical, especially dermatological preparations of the invention may also comprise lipids chosen from the following group of substances:
  • Qi is a linear or branched alkyl radical having 6 to 24 C atoms and
  • Q 2 is a linear or branched alkyl radical having 4 to 16 C atoms.
  • An oil phase or oil component in the narrower (and preferred) sense of the present invention i.e. of the inventively limited substances or substances present only in a minor fraction, encompasses the following groups of substances:
  • silicone oils from the group of the cyclotrisiloxanes, cyclopentasiloxanes, dimethylpolysiloxanes, diethylpolysiloxanes, methylphenylpolysiloxanes, diphenylpolysiloxanes and hybrid forms thereof;
  • Q 1 is a (preferably linear) alkyl radical having 6 to 18 C atoms and
  • Q 2 is a (preferably linear) alkyl radical having 4 to 16 C atoms.
  • An oil phase in the narrowest (and most preferred) sense of the present invention encompasses the following groups of substances:
  • silicone oils from the group undecamethylcyclotrisiloxane, cyclomethicone, decamethylcyclopentasiloxane, dimethylpolysiloxanes, diethylpolysilox- anes, methylphenylpolysiloxanes and diphenylpolysiloxanes;
  • Q 1 is a (preferably linear) alkyl radical having 6 to 18 C atoms and
  • Q 2 is a (preferably linear) alkyl radical having 4 to 16 C atoms.
  • Particularly preferred components of type (i) in the oil phase are as follows: iso- propyl myristate, isopropyl palmitate, isopropyl stearate, 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-octyldodecyl palmitate, oleyl oleate, oleyl erucate, erucyl oleate, erucyl erucate, 2-ethylhexyl isostearate, isotridecyl isononanoate, 2-ethylhexyl coco
  • Fatty acid triglycerides may also be in the form of, or in the form of a constituent of, synthetic, semisynthetic and/or natural oils, examples being olive oil, sunflower oil, soya oil, peanut oil, rapeseed oil, almond oil, palm oil, coconut oil, palm kernel oil and mixtures thereof.
  • Particularly preferred oil components of type (vii) in the oil phase are as follows: 2-butyl-1 -octanol, 2-hexyl-1 -decanol, 2-octyl-1 -dodecanol, 2-decyltetradecanol, 2-dodecyl-1 -hexadecanol and 2-tetradecyl-1 -octadecanol.
  • Particularly preferred oil components in the oil phase are mixtures comprising Ci 2 -Ci5-alkyl benzoate and 2-ethylhexyl isostearate, mixtures comprising Ci 2 -Ci 5 - alkyl benzoate and isotridecyl isononanoate, mixtures comprising Ci 2 -Ci 5 -alkyl benzoate, 2-ethylhexyl isostearate and isotridecyl isononanoate, mixtures com- prising cyclomethicone and isotridecyl isononanoate, and mixtures comprising cyclomethicone and 2-ethylhexyl isostearate.
  • Preferred embodiments of the cosmetic and/or pharmaceutical, especially der- matologically active preparations of the invention may advantageously also comprise the use of polymers to imrove the spreadibility of the formulation upon the skin or hair, or improve the water and or sweat and or rub-off resistancy of the formula and to improve the protection factor of the formulation.
  • Examples of such polymers are : VP/Eicosene copolymers sold under the trade name of Antaron V-220 by International Speciality Products, VP/Hexadecene copolymer sold under the trade names Antaron V-216 and Antaron V-516 by International Speci- ality Products, Tricontanyl PVP sold under the trade name of Antaron WP-660 by International Speciality Products, Isohexadecane and Ethyl- ene/Propylene/Styrene copolymer and Butylene/Styrene copolymer sold under the trade names of Versagel MC and MD by Penreco, Hydrogenated polyisobu- tene and and Ethylene/Propylene/Styrene copolymer and Butylene/Styrene copolymer sold under the trade mane of Versagel ME by Penreco, Acry- lates/Octylacrylamide Coploymers sold under the trade
  • the amount of polymers used to obtain the desired effect in the formulation range from 0.10% to 5.0% by weight of the fomulation and especially in the range from 0.25% to 3.0% by weight of the formulation.
  • Preferred embodiments of the cosmetic and/or pharmaceutical, especially der- matologically active preparations of the invention comprise, if desired, further ingredients having care properties, such as, for example, fatty alcohols having 6 to 30 C atoms.
  • the fatty alcohols here can be saturated or unsaturated and linear or branched. Furthermore, these fatty alcohols can in some cases be part of the oil phase (III) if they correspond to the definition given there.
  • Alcohols which can be employed are, for example, decanol, decenol, octanol, octenol, dodecanol, dodecenol, octadienol, decadienol, dodecadienol, oleyl alcohol, rici- noleyl alcohol, erucyl alcohol, stearyl alcohol, isostearyl alcohol, cetyl alcohol, lauryl alcohol, myristyl alcohol, arachidyl alcohol, caprylyl alcohol, capryl alcohol, linoleyl alcohol, linolenyl alcohol and behenyl alcohol, and also Guerbet alcohols thereof, such as, for example, 2-octyl-1 -dodecanol, it being possible for the list to be extended virtually as desired by further alcohols of related structural chemis- try.
  • the fatty alcohols preferably originate from natural fatty acids, being conventionally prepared from the corresponding esters of the fatty acids by reduction.
  • Fatty alcohol fractions which are formed by reduction from naturally occurring fats and fatty oils, such as beef tallow, peanut oil, colza oil, cottonseed oil, soya oil, sunflower oil, palm kernel oil, linseed oil, maize oil, castor oil, rapeseed oil, sesame oil, cacao butter and coconut fat, can further be employed.
  • Substances having care properties which advantageously can be employed in the cosmetic and/or dermatologically active preparations can further include
  • ceramides where ceramides are understood as meaning N- acylsphingosins (fatty acid amides of sphingosin) or synthetic analogues of such lipids (so-called pseudo-ceramides), which significantly improve the water retention capacity of the stratum corneum.
  • phospholipids for example soya lecithin, egg lecithin and cephalins
  • phytosterols and phytosterol-containing fats or waxes are examples of phytosterols and phytosterol-containing fats or waxes
  • paraffin oils and silicone oils include, inter alia, dialkyl- and alkylarylsiloxanes, such as dimethylpolysiloxane and methylphenyl- polysiloxane, and also alkoxylated and quaternised derivatives thereof.
  • Animal and/or plant protein hydrolysates can advantageously also be added to preferred embodiments of cosmetic and/or pharmaceutical, especially derma- tologically active, preparations of the invention.
  • Substances which are advantageous in this respect are, in particular, elastin, collagen, keratin, milk protein, soya protein, oat protein, pea protein, almond protein and wheat protein fractions or corresponding protein hydrolysates, and also condensation products thereof with fatty acids, and quaternised protein hydrolysates, the use of plant protein hydrolysates being preferred.
  • the aqueous phase of the preparations according to the present invention optionally advantageously comprises alcohols, diols or polyols (lower alkyl), and ethers thereof, preferably ethanol, isopropanol, propylene glycol, 1 ,2-hexanediol, 1 ,2-octanediol, 1 ,2-decanediol, a mixture of 1 ,2-hexanediol and 1 ,2-octanediol, a mixture of 1 ,2-hexanediol and 1 ,2-decanediol, a mixture of 1 ,2-octanediol and 1 ,2-decanediol, a mixture of 1 ,2-hexanediol, 1 ,2-octanediol and 1 ,2-decanediol, a mixture of 1 ,2-hexanediol, 1
  • ethanol 1 ,2-propanediol, glycerol, and, in particular, one or more thickeners which can advantageously be chosen from the group of silicon dioxide, aluminum silicates, polysaccharides and derivatives thereof, e.g. hyaluronic acid, xanthan gum, hydroxypropylmethylcellulose, particularly advantageously from the group of polyacrylates, preferably a polyacrylate from the group of so-called Carbopols, for example, Carbopol grades 980, 981 , 1382, 2984, 5984, in each case individually or in combination.
  • Carbopols for example, Carbopol grades 980, 981 , 1382, 2984, 5984, in each case individually or in combination.
  • Preferred embodiments of the cosmetic and/or pharmaceutical, especially der- matologically active preparations of the invention may also comprise active antiinflammatory and/or redness- and/or itching-alleviating compounds (anti-irritants). All the active anti-inflammatory or redness- and/or itching-alleviating compounds which are suitable or usual for cosmetic and/or dermatological applications can be used here.
  • Active anti-inflammatory and redness- and/or itching-alleviating compounds which are advantageously employed are steroidal anti-inflammatory substances of the corticosteroid type, such as hydrocortisone, dexamethasone, dexamethasone phosphate, methylprednisolone or cortisone, it being possible for the list to be extended by addition of further steroidal anti-inflammatories.
  • Non- steroidal anti-inflammatories can also be employed.
  • oxicams such as piroxicam or tenoxicam
  • salicylates such as aspirin, Disalcid, Solprin or fendosal
  • acetic acid derivatives such as diclofenac, fenclofenac, indomethacin, sulindac, tolmetin, or clindanac
  • fena- mates such as mefenamic, meclofenamic, flufenamic or niflumic
  • propionic acid derivatives such as ibuprofen, naproxen, benoxaprofen or pyrazoles, such as phenylbutazone, oxyphenylbutazone, febrazone or azapropazone.
  • natural anti-inflammatory or redness- and/or itching-alleviating substances can be employed.
  • Plant extracts, specific highly active plant extract fractions and highly pure active substances isolated from plant extracts can be employed. Extracts, fractions and active substances from camomile, aloe vera, Commiphora species, Rubia species, willow, rose-bay willow-herb, oats, and also pure substances, such as, inter alia, bisabolol, apigenin 7-glucoside, boswellic acid, phytosterols, glycyrrhizic acid, glabridin or licochalcone A, are particularly preferred.
  • the preparations of the present invention can also comprise mixtures of two or more active anti-inflammatory compounds.
  • Bisabolol, boswellic acid, and also extracts and isolated highly pure active compounds from oats and Echinacea are particularly preferred for use in the context of the invention as antiinflammatory and redness- and/or itching-alleviating substances, and alpha- bisabolol and extracts and isolated highly pure active compounds from oats are especially preferred.
  • the amount of anti-irritants (one or more compounds) in the preparations is preferably 0.0001% to 20% by weight, with particular preference 0.0001 % to 10% by weight, in particular 0.001 % to 5% by weight, based on the total weight of the preparation.
  • Preferred embodiments of the cosmetic and/or pharmaceutical, especially der- matologically active preparations of the invention may advantageously also comprise moisture retention regulators.
  • the following substances for example are used as moisture retention regulators (moisturizers): sodium lactate, urea, alcohols, sorbitol, glycerol, propylene glycol, aliphatic 1 ,2-diols with a C number of 5- 10, collagen, elastin or hyaluronic acid, diacyl adipates, petrolatum, ectoin, uro- canic acid, lecithin, pantheol, phytantriol, lycopene, algae extract, ceramides, cholesterol, glycolipids, chitosan, chondroitin sulphate, polyamino acids and polyamino sugars, lanolin, lanolin esters, amino acids, alpha-hydroxy acids (e.g.
  • citric acid lactic acid, malic acid
  • sugars e.g. inositol
  • alpha-hydroxy fatty acids e.g. 1,3-bis(trimethyl)
  • phytosterols e.g. 1,3-bis(trimethyl)
  • triterpene acids such as betulinic acid or ursolic acid
  • algae extracts
  • Preferred embodiments of the cosmetic and/or pharmaceutical, especially der- matologically active preparations of the invention may advantageously also comprise mono-, di- and oligosaccharides, such as, for example, glucose, galactose, fructose, mannose, fruit sugars and lactose.
  • Preferred embodiments of the cosmetic and/or pharmaceutical, especially der- matologically active preparations of the invention may advantageously also comprise plant extracts, which are conventionally prepared by extraction of the whole plant, but also in individual cases exclusively from blossom and/or leaves, wood, bark or roots of the plant.
  • Extracts which are advantageous in particular are those from aloe, witch hazel, algae, oak bark, rose-bay willow-herb, stinging nettle, dead nettle, hops, camomile, yarrow, arnica, calendula, burdock root, horsetail, hawthorn, linden blossom, almond, pine needle, horse chestnut, sandalwood, juniper, coconut, mango, apricot, orange, lemon, lime, grapefruit, apple, green tea, grapefruit pip, wheat, oats, barley, sage, thyme, wild thyme, rosemary, birch, mallow, lady's smock, willow bark, restharrow, coltsfoot, hibiscus, ginseng and ginger root.
  • the extracts from aloe vera, camomile, algae, rosemary, calendula, ginseng, cucumber, sage, stinging nettle, linden blossom, arnica and witch hazel are particularly preferred.
  • Mixtures of two or more plant extracts can also be employed.
  • Extraction agents which can be used for the preparation of plant extracts mentioned are, inter alia, water, alcohols and mixtures thereof.
  • alcohols lower alcohols, such as ethanol and isopropanol, but also polyhydric alcohols, such as ethylene glycol, propylene glycol and butylene glycol, are preferred, and in particular both as the sole extraction agent and in mixtures with water.
  • the plant extracts can be employed both in pure and in diluted form.
  • Preferred embodiments of the cosmetic and/or pharmaceutical, especially der- matologically active preparations of the invention may in numerous cases advan- tageously comprise the following preservatives:
  • Preservatives which are preferably chosen here are those such as benzoic acid, its esters and salts, propionic acid and its salts, salicylic acid and its salts, 2,4-hexadienoic acid (sorbic acid) and its salts, formaldehyde and paraformaldehyde, 2-hydroxybiphenyl ether and its salts, 2-zincsulphidopyridine N-oxide, inorganic sulphites and bisulphites, sodium iodate, chlorobutanolum, 4-ethylmercuryl(ll)-5-amino-1 ,3-bis(2-hydroxybenzoic acid), its salts and esters, dehydracetic acid, formic acid, 1 ,6-bis(4-amidino-2-bromophenoxy)-n-hexane and its
  • cosmetic and/or pharmaceutical, especially dermatologically active preparations of the invention may also comprise substances having a cooling action.
  • Individual active cooling compounds which are preferred for use in the context of the present invention are listed below. The skilled person is able to supplement the following list with a large number of further active cooling compounds; the active cooling compounds listed can also be employed in combination with one another: l-menthol, d-menthol, racemic menthol, menthone glycerol acetal (trade name: Frescolat ® MGA), menthyl lactate (trade name: Frescolat ® ML, menthyl lactate is preferably l-menthyl lactate, in particular l-menthyl l-lactate), substituted menthyl-3-carboxylic acid amides (e.g.
  • menthyl 3- hydroxybutyrate monomenthyl succinate, 2-mercaptocyclodecanone, menthyl 2-pyrrolidin-5-onecarboxylate, 2,3-dihydroxy-p-menthane, 3,3,5-trimethylcyclo- hexanone glycerol ketal, 3-menthyl 3,6-di- and -trioxaalkanoates, 3-menthyl methoxyacetate, icilin.
  • Preferred active cooling compounds are: l-menthol, d-menthol, racemic menthol, menthone glycerol acetal (trade name: Frescolat ® MGA), menthyl lactate (pref- erably l-menthyl lactate, in particular l-menthyl l-lactate, trade name: Fresco- lat ® ML), substituted menthyl-3-carboxylic acid amides (e.g.
  • menthyl-3-carboxylic acid N-ethylamide 2-isopropyl-N-2,3-trimethylbutanamide, substituted cyclo- hexanecarboxylic acid amides, 3-menthoxypropane-1 ,2-diol, 2-hydroxtethyl menthyl carbonate, 2-hydroxypropyl menthyl carbonate, isopule- gol.
  • Particularly preferred active cooling compounds are: l-menthol, racemic menthol, menthone glycerol acetal (trade name: Frescolat ® MGA), menthyl lactate (preferably l-menthyl lactate, in particular l-menthyl l-lactate, trade name: Fresco- lat ® ML), 3-menthoxypropane-1 ,2-diol, 2-hydroxyethyl menthyl carbonate, 2- hydroxypropyl menthyl carbonate.
  • Very particularly preferred active cooling compounds are: l-menthol, menthone glycerol acetal (trade name: Frescolat ® MGA), menthyl lactate (preferably l-menthyl lactate, in particular l-menthyl l-lactate, trade name: Frescolat ® ML).
  • the use concentration of the active cooling compounds to be employed is, depending on the substance, preferably in the concentration range from 0.01 % to 20% by weight, and more preferably in the concentration range from 0.1% to 5% by weight, based on the total weight of the completed (ready-to-use) cosmetic or pharmaceutical preparation.
  • Benzophenone-4 in this example has been neutralised with sodium hydroxide.
  • the sodium salt of Benzophenone-4 is also called Benzophenone-5 and the same quenching effect is observed whether Benzophenone 4 neutralised in-situ or when Benzophenone-5 is used.
  • Part B Mix all ingredients together and heat to 85 9 C, then add to Part A. with stirring. Homogenise and cool to ambient temperature.
  • Part C Add to parts A and B at 30 °C with stirring. Homogenise.
  • Part A Heat to about 85 0 C.
  • Part B Weigh in raw materials without Carbopol. Disperse Carbopol therein using Ultra Turrax. Heat to about 85 °C. Add B to A. and then homogenise while hot (Ultra Turrax). Leave to cool with stirring.
  • Part C Add to A/B at 30 'O or less with stirring
  • Part A Heat to about 85 0 C.
  • Part B Weigh in raw materials without Carbopol. Disperse Carbopol therein using Ultra Turrax. Heat to about 85 °C. Add B to A.
  • Part C Immediately add to A/B and then homogenise while hot (Ultra Tur- rax). Leave to cool with stirring.
  • Part D Add and stir in.
  • Part A Heat to 80-85 0 C.
  • Part B Heat to 80-85°C, Add part B to part A with stirring.
  • Part C Disperse Carbopol into the water and neutralise with NaOH, with stirring. Add part C at about 60 °C with stirring. Allow to cool to RT (room temperature).
  • Part D Add and stir.
  • Part A Dissolve the solids in the oils and liquid UV filters (heating to about 70 ⁇ ). Allow to cool to about 30 'O, add the remaining constituents apart from Carbopol and Pemulen and mix at room temperature (stir for about 5 minutes). Stir in Carbopol and Pemulen.
  • Part B Add water and glycerin, then disperse Neo Heliopan® Hydro with vigorous stirring and heating to 70 °C, add Amino Methyl Propanol until all of the Neo Heliopan® Hydro, Neo Heliopan® AP and Benzo- phenone-4 has been dissolved and add all of part B to part A with stirring. Stir for about 60 minutes with cooling and homogenise using the Ultra Turrax.
  • Part C Stir in at ambient temperature.
  • Part A Heat to about 85 0 C.
  • Part B Heat to about 85°C. Add B to A. Allow to cool with stirring then homogenise.
  • Part C Stir in at ambient temperature.
  • Part A Heat to about 85 0 C.
  • Part B Heat to about 85°C (without zinc oxide; disperse zinc oxide therein using the Ultra Turrax). Add B to A. Allow to cool with stirring.
  • Part C Add and then homogenise.
  • Part A Heat to 80 °C.
  • Part B Heat to 80°C Add to part A with stirring.
  • Part C Disperse Carbopol in water and neutralise with sodium hydroxide solution. Add to part A/B at about 55 °C.
  • Part D Stir in at ambient temperature.
  • Part A Dissolve Lara Care A-200 into the other constituents of part A with stirring.
  • Part B Weigh in all raw materials (without Pemulen) and dissolve the crystalline substances with heating. Disperse Pemulen therein. Add part B to part A then homogenise for 1 minute.
  • Part C Stirr in the ingredients until all have dissolved and add part C+D then homogenise again for 1 -2 minutes using the Ultra Turrax.
  • Part A Disperse Carbopol in water and neutralise with triethanolamine solu- tion.
  • Part B Add to part A with stirring.
  • Part C Dissolve crystalline constituents in the other raw materials of part C with warming (max.40°C) and add to part A/B. Stir well and then ho- mogenise. (Homozenta).
  • Part A Heat to 80 0 C.
  • Part B Swell Natrosol in water, Neo Heliopan® AP, Benzophenone-4 and Amino Methyl propanol, add Nipagin M and heat to 80 °C. Add to part A with stirring and emulsify. Cool down with stirring. Part C: Add at 35 ⁇ and cool to RT with stirring.
  • Part A Stir Amaze XT into the water with stirring until it is swollen and a gel has formed
  • Part B Stir the ingredients together and add to Part A and then add Parts C with stirring until uniform and then add Part D with gentle stirring.
  • Part A Heat all components except for the Xanthan Gum and TiO 2 to 85 °C. Then add Xanthan Gum and TiO 2 and homogenise.
  • Part B Heat all components to ⁇ 'O and add to Part A with stirring, stir to room temperature.
  • Part C Add Part C to Parts A & B and homogenise.
  • Part A Dissolve the Neo Heliopan 357 in the other components of phase A (except for Pemulen and EDTA) by heating up to 50 9 C.
  • Part B Add to Part A without stirring, then start emulsifying.
  • Part C Add Part C to Parts A & B while homogenising.
  • Part A Dissolve Merquat in water with stirring
  • Part B Add Neo Heliopan Hydro and neutralise with Amino Methyl Propanol, dissolve until a clear solution has formed.
  • Part C Add the ingredients to part AB as listed and stir until a uniform solu- tion has formed.
  • the viscosity can be adjusted by the amount of sodium chloride.
  • the pH of the resulting formulation was in the range of 5.2 - 5.5

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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)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne des préparations cosmétiques destinées à protéger la peau et les cheveux contre les effets nocifs du rayonnement solaire ultraviolet, ces préparations contenant la substance hydrosoluble anti UVA phényl-dibenzimidazole-tétrasulfonate disodique [acide 2,2'-(1,4-phénylène)bis(1H-benzimidazole-4,6-disulfonique, sel monosodique); acide 1H-benzimidazole-4,6-disulfonique, 2,2'-(1,4-phénylène)bis-, sel disodique] associée à la benzophénone-4 (acide 2-hydroxy-4-méthoxybenzophénone-5-sulfonique) et ses sels pour éteindre la fluorescence du phényl-dibenzimidazole-tétrasulfonate disodique.
PCT/EP2007/056997 2007-07-09 2007-07-09 Utilisation de benzophénone-4 et de ses sels pour éteindre la fluorescence du phényl-dibenzimidazole-tétrasulfonate disodique Ceased WO2007135197A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/EP2007/056997 WO2007135197A2 (fr) 2007-07-09 2007-07-09 Utilisation de benzophénone-4 et de ses sels pour éteindre la fluorescence du phényl-dibenzimidazole-tétrasulfonate disodique

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2007/056997 WO2007135197A2 (fr) 2007-07-09 2007-07-09 Utilisation de benzophénone-4 et de ses sels pour éteindre la fluorescence du phényl-dibenzimidazole-tétrasulfonate disodique

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WO2007135197A2 true WO2007135197A2 (fr) 2007-11-29
WO2007135197A3 WO2007135197A3 (fr) 2008-05-02

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011000069A2 (fr) 2009-06-29 2011-01-06 Natura Cosméticos S.A. Composition cosmétique, kit de traitement cutané, méthode de traitement des peaux grasses ou mixtes ou des peaux acnéiques
JP2011513320A (ja) * 2008-02-27 2011-04-28 シェーリング−プラウ ヘルスケア プロダクツ，インコーポレイテッド アボベンゾンを含有するサンケア組成物の増強された光安定性
US20140093469A1 (en) * 2011-06-10 2014-04-03 Henkel Ag & Co., Kgaa Shine-producing hair-styling product with a strong hold, providing hair with a pleasant feel
WO2013102248A3 (fr) * 2012-01-06 2014-08-07 . Johnson & Johnson Do Brasil Industria E Comercio De Produtos Para Saude Ltda. Composition cosmétique aqueuse de protection solaire et son utilisation, procédé cosmétique pour l'application de ladite composition, procédé cosmétique pour prévenir et réguler la séborrhée de la peau, procédé cosmétique pour protéger la peau des lésions provoquées par le rayonnement ultraviolet et produit cosmétique
US10039700B2 (en) 2009-04-27 2018-08-07 Bayer Healthcare Llc Enhanced efficiency of sunscreen compositions
EP4176936A1 (fr) * 2021-11-08 2023-05-10 Martiderm, SL Préparation cosmétique pour la protection de la peau et des cheveux contre le rayonnement solaire

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19820660C5 (de) * 1998-05-08 2010-03-04 Stada Arzneimittel Ag Gelförmige Lichtschutzzubereitungen, enthaltend öl- und wasserlösliche UV-Filter
FR2879454B1 (fr) * 2004-12-20 2007-02-23 Oreal Composition solaire comprenant au moins un filtre uv hydrophile et au moins une hydroxyalkyluree

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011513320A (ja) * 2008-02-27 2011-04-28 シェーリング−プラウ ヘルスケア プロダクツ，インコーポレイテッド アボベンゾンを含有するサンケア組成物の増強された光安定性
US10039700B2 (en) 2009-04-27 2018-08-07 Bayer Healthcare Llc Enhanced efficiency of sunscreen compositions
US12151009B2 (en) 2009-04-27 2024-11-26 Beiersdorf Ag Enhanced efficiency of sunscreen compositions
WO2011000069A2 (fr) 2009-06-29 2011-01-06 Natura Cosméticos S.A. Composition cosmétique, kit de traitement cutané, méthode de traitement des peaux grasses ou mixtes ou des peaux acnéiques
US20140093469A1 (en) * 2011-06-10 2014-04-03 Henkel Ag & Co., Kgaa Shine-producing hair-styling product with a strong hold, providing hair with a pleasant feel
WO2013102248A3 (fr) * 2012-01-06 2014-08-07 . Johnson & Johnson Do Brasil Industria E Comercio De Produtos Para Saude Ltda. Composition cosmétique aqueuse de protection solaire et son utilisation, procédé cosmétique pour l'application de ladite composition, procédé cosmétique pour prévenir et réguler la séborrhée de la peau, procédé cosmétique pour protéger la peau des lésions provoquées par le rayonnement ultraviolet et produit cosmétique
EP4176936A1 (fr) * 2021-11-08 2023-05-10 Martiderm, SL Préparation cosmétique pour la protection de la peau et des cheveux contre le rayonnement solaire

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