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WO2024027929A1 - Composition avec résistance à l'eau améliorée - Google Patents

Composition avec résistance à l'eau améliorée Download PDF

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Publication number
WO2024027929A1
WO2024027929A1 PCT/EP2022/072098 EP2022072098W WO2024027929A1 WO 2024027929 A1 WO2024027929 A1 WO 2024027929A1 EP 2022072098 W EP2022072098 W EP 2022072098W WO 2024027929 A1 WO2024027929 A1 WO 2024027929A1
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WO
WIPO (PCT)
Prior art keywords
unsubstituted
substituted
alkyl
group
dimethicone
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2022/072098
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English (en)
Inventor
Jürgen Claus
Ev Suess
Imke Meyer
Nikolas BUGDAHN
Sabine Lange
Carolin HEIN
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Symrise AG
Original Assignee
Symrise 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 Symrise AG filed Critical Symrise AG
Priority to PCT/EP2022/072098 priority Critical patent/WO2024027929A1/fr
Priority to PCT/EP2023/071782 priority patent/WO2024028511A1/fr
Priority to EP23754247.7A priority patent/EP4565193A1/fr
Priority to CN202380054706.3A priority patent/CN120379638A/zh
Publication of WO2024027929A1 publication Critical patent/WO2024027929A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • 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
    • 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
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • 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
    • 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
    • A61Q19/005—Preparations for sensitive skin
    • 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
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • 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
    • A61Q19/08—Anti-ageing 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
    • A61Q5/12—Preparations containing hair conditioners

Definitions

  • the present invention relates to sunscreen products, cosmetic or pharmaceutical preparations or homecare products comprising at least one primary organic and/or inorganic UV-filter, a certain mycosporine-like amino acid compound and optionally at least one film forming agent.
  • the products and preparations provide improved water resistance and, thus, increased SPF performance without being unpleasantly sticky.
  • the present invention relates to the use of such mycosporine-like amino acid compound for improving water resistance and, thus, SPF performance, of a sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprising at least one primary organic and/or inorganic UV-filter and optionally at least one film forming agent.
  • the present invention relates to a method of increasing the water resistance and, thus, SPF performance, of a sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprising at least one primary organic and/or inorganic UV-filter and optionally at least one film forming agent by the addition of a certain mycosporine-like amino acid compound.
  • Background Art [0002] The negative effects of exposure of UV light are well-known. Prolonged exposure to sunlight causes damage such as sunburn to the skin and dries out hair making it brittle. When skin is exposed to UV light having a wavelength of from 290 nm to 400 nm, long term damage can lead to serious conditions such as skin cancer, the type of damage depending on the wavelength of the radiation.
  • UV light also contributes to aging by causing free radicals to form in the skin.
  • Free radicals include, for example, singlet oxygen, hydroxyl radical, the superoxide anion, nitric oxide and hydrogen radicals. Free radicals attack DNA, membrane lipids and proteins, generating carbon radicals. These in turn react with oxygen to produce a peroxyl radical that can attack adjacent fatty acids to generate new carbon radicals.
  • This cascade leads 220084 to a chain reaction producing lipid peroxidation products. Damage to the cell membrane results in loss of cell permeability, increased intercellular ionic concentration, and decreased ability to excrete or detoxify waste products. The end result is a loss of skin elasticity and the appearance of wrinkles. This process is commonly referred to as photo- aging.
  • UVA-radiation can trigger phototoxic or photo allergic skin reactions.
  • UV rays are classified according to their wavelength as UVA rays (320 to 400 nm) or UVB rays (280 to 320 nm).
  • anti-sun/sunscreen compositions comprising screening agents that are active in the UVA-range and in the UVB-range, i.e. within the full range of 280 nm to 400 nm, are generally used.
  • UV-filters are compounds which have a pronounced absorption capacity for ultraviolet radiation.
  • UVA and UVB filters are classified as UVA and UVB filters depending on the location of their absorption maxima; if a UV-filter absorbs both UVA and UVB, it is referred to as a UVA/B broadband absorber or UVA/UVB broadband filter.
  • UV-filters which can be used for the protection of skin are regulated in the USA by the America FDA via their OTC monograph system and are regulated in the European Union by the Cosmetic Regulation. Regulations covering the use of UV-filters exist in other countries and regions as well. These regulations not only stipulate the filters which can be used but also fix a maximum usage level for each UV-filter.
  • UV-filters available to achieve high efficacy with respect to both SPF and UVA or UVB protection.
  • formulators When updating a sunscreen formulation to meet today’s requirements, formulators must consider improved water-resistance as a key parameter, since sunscreens are often used outdoors near bodies of water. Exposure of a sunscreen product to water, such as typically occurring when bathing, results in a significant removal of the UV-filter from the skin, either by leaching out or by physical removing, which leads to a decrease of protection capacity against the UV light. This can be shown by a significant decrease of the composition’s SPF. Reapplication of the product after each water exposure is undesirable for modern consumers who seek both comfort and ease of use from their sun care products.
  • sufficient or high water-resistance can be accomplished by: preparing a fully anhydrous formulation; creating a w/o emulsion; adding alcohol to dissolve water-insoluble substances that deposit onto the skin from an insoluble layer; obtaining a meta-stable o/w emulsion with a low level of emulsifiers; and entrapping filters in skin-substantive liposomes or sponges.
  • One or more of these strategies are used when formulating a water-resistant formulation.
  • Water resistance of sun care products can further be improved by the addition of film forming polymers.
  • Water-resistant products are more likely to achieve lower transdermal delivery since their components are contained inside the applied film. This factor allows water-resistant sunscreens to provide longer-lasting SPF protection than standard sunscreen products.
  • the UV-filters entrapped in the film will have 220084 low transdermal delivery to the body, reducing the risk of chemicals penetrating the skin and lowering the accumulation of said substances.
  • These film forming polymers are either not sufficiently effective and/or render the product unattractive for the end consumer due to the resulting sensory properties as such products often exhibit an oily, dull, heavy or sticky feeling on the skin.
  • the present invention provides in a first aspect a sunscreen product, a cosmetic or pharmaceutical preparation or homecare product, comprising or consisting of (a) at least one primary organic and/or inorganic UV-filter; and (b) at least one mycosporine-like amino acid compound, represented either by the general formula (I) formula (I), as defined herein, or a tautomer or a salt thereof; or represented by the general formula (II) 220084 formula (II), as defined herein, or a tautomer or a salt thereof; or any mixture of the afore-mentioned compounds; and (c) optionally at least one film forming agent.
  • the present invention provides for the use of at least one mycosporine-like amino acid compound as defined herein or a mixture thereof for improving the water resistance and SPF performance of a sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprising at least one primary organic and/or inorganic UV-filter and optionally a film forming agent.
  • the present invention relates in a further aspect to a method of increasing the water resistance and/or SPF of a sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprising at least one primary organic and/or inorganic UV-filter and optionally a film forming agent, said method comprising the addition of an effective amount of a mycosporine-like amino acid compound as defined herein or a mixture thereof to said sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprising at least one UV-filter and optionally a film forming agent.
  • the term “at least one ...compound” means that the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention can comprise either one of said subsequently described individual compound or a mixture of two, three, four, five, six or even more different of said subsequently compounds.
  • the term “optionally” means that the subsequently described compound may but need not to be present in the composition, and that the description includes variants, where the compound is included or variants, where the compound is absent.
  • a “sunscreen product” in the context of the present invention is a photoprotective topical product for the skin including UV-filter compounds that absorbs or reflects some of the sun’s ultraviolet (UV) radiation and thus helps protect against sunburn and most importantly prevent skin cancer.
  • Sunscreens come as lotions, sprays, gels, foams (such as an expanded foam lotion or whipped lotion), sticks, powders and other topical products.
  • UV-absorbing compounds are used not only in sunscreen, but also in other personal care products, such as lipstick, shampoo, hair spray, body wash, toilet soap, and insect repellent.
  • cosmetic or pharmaceutical preparations in the context of the present invention are compositions for cosmetic or pharmaceutical purposes which contain a UV absorber in order to protect skin or hair against UV-radiation.
  • the cosmetic or pharmaceutical preparations according to the present invention are useful for providing anti-aging benefits to skin, whitening or preventing darkening of skin, improving appearance of skin, diminishing the visible signs of skin aging and improving skin’s radiance and firmness.
  • homecare products in the context of the present invention are the essentials for daily care and cleaning purpose in households. They are used for maintaining hygiene and a good aura of the homes.
  • the home care products generally include laundry detergents (powder, liquid and tablet), fabric conditioners, dishwashing detergents (liquid and tablet), hard floor and surface cleaners, glass cleaners, carpet cleaners, oven cleaners, air fresheners, disinfectants, stain removers, car wash products. These products are usually manufactured in the form of a liquid, powder, spray, granules and others. Such sunscreen containing formulations prevent premature photodamage and photobleaching to surfaces and the homecare formulation itself.
  • the component (a) of the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the first aspect of the present invention relates to at least one primary UV-filter.
  • UV-filters are well known in the art for their use in stopping radiation.
  • a UV-filter is a compound or a mixture of compounds that block or absorb ultraviolet (UV) light.
  • UV classifications include UVA (320 to 400 nm), UVB (290 to 320 nm) and UVC (200 to 280 nm).
  • UV-absorbing compounds are used not only in sunscreen, but also in other personal care products, such as lipstick, shampoo, hair spray, body wash, toilet soap, and insect repellent.
  • Chemical filters protect against UV-radiation by absorbing, reflecting, or scattering.
  • the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the invention advantageously contains at least one UVA filter and/or at least one further UVB filter and/or a broadband filter and/or at least one inorganic pigment, preferably at least one UVA filter and at least one UVB filter for their use in stopping UV radiation.
  • the at least one primary UV-filter may be one or more organic UV- filters and/or one or more inorganic UV-filters.
  • UV-filters include: 220084 (i) sparingly soluble UV-filters (not appreciably soluble in either water or oil) such as Methylene Bis-benzotriazolyl Tetramethylbutylphenol, Tris- Biphenyl Triazine, Methanone, 1,1'-(1,4-piperazinediyl)bis[1-[2-[4-(diethylamino)-2-hydroxybenzoyl- ]phenyl]; (ii) oil soluble organic UV-filters (at least partially soluble in oil or organic solvent), such as Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine, Butyl Methoxydibenzoylmethane (BMBM), Oxybenzone, Sulisobenzone, Diethylhexyl Butamido Triazone (DBT), Drometrizole Trisiloxane, Ethylhexyl Methoxycinnamate (EHMC), E
  • Benzophenones a. Benzophenone-3 (BP3) b. Benzophenone-4 (BP4)
  • Salicylates a. Homosalate (HMS) b. 2-ethylhexyl salicylate (EHS)
  • EHS 2-ethylhexyl salicylate
  • p-Aminobenzoic acid and derivatives a. Ethylhexyl dimethyl PABA (OD-PABA) b.
  • PABA 4-p-aminobenzoic acid
  • Benzimidazole derivatives a. Phenylbenzimidazole sulfonic acid (PMDSA) 220084 b.
  • Cinnamates a. Ethylhexyl methoxycinnamate (OMC) b. Isoamyl p-methoxycinnamate (IMC, amiloxate) (9) Camphor derivatives a. Terephtalydene dicamphor sulfonic acid (PDSA) b. 3-benzylidene camphor (3BC) c. Benzylidene camphor sulfonic acid (BCSA) d. 4-methylbenzylidene camphor (4-MBC) e.
  • OMC Ethylhexyl methoxycinnamate
  • IMC Isoamyl p-methoxycinnamate
  • Camphor derivatives a. Terephtalydene dicamphor sulfonic acid (PDSA) b. 3-benzylidene camphor (3BC) c. Benzylidene camphor sulfonic acid (BCSA) d. 4-methylbenzy
  • the at least one inorganic UV-filter (a) is selected from the group of pigments consisting of titanium dioxide (TiO2) (amorphous or crystallized in rutile and/or anatase form), zinc oxide (ZnO), iron oxide (Fe2O3), zirconium oxide (ZrO2), silicon (SiO2), manganese (e.g. MnO), aluminium (Al2O3), cerium oxide (Ce2O3), barium carbonate (BaCO3), calcium carbonate (CaCO3), and mixtures thereof.
  • the at least one inorganic UV-filter is titanium dioxide, zinc oxide, and mixtures thereof, more preferably the at least one inorganic UV-filter is titanium oxide and/or zinc oxide, and most preferably, the at least one inorganic UV-filter is zinc oxide.
  • ZnO has a broad UVA/UVB absorption curve, while TiO2 provides better UVB protection.
  • the at least one inorganic UV-filter is in form of particles having a weight medium particle size d50 from 1 nm to 1000 nm, preferably from 3 nm to 800 nm, more preferably from 5 nm to 600 nm, and most preferably from 10 nm to 400 nm.
  • the inorganic UV-filters also encompass nano pigments (mean size of the primary particles: generally from 1 nm to 100 nm, preferably from 3 nm to 90 nm, more preferred from 5 nm to 80 nm and most preferred from 10 to 70 nm) of untreated or treated metal oxides such as, for example, nano pigments of titanium dioxide (TiO2) (amorphous or crystallized in rutile and/or anatase form), zinc oxide (ZnO), iron oxide (Fe2O3), zirconium oxide (ZrO2), silicon (SiO2), manganese (e.g.
  • nano pigments mean size of the primary particles: generally from 1 nm to 100 nm, preferably from 3 nm to 90 nm, more preferred from 5 nm to 80 nm and most preferred from 10 to 70 nm
  • untreated or treated metal oxides such as, for example, nano pigments of titanium dioxide (TiO2) (amorphous or crystallized in
  • the treated nano pigments and non-nano pigments are pigments that have undergone one or more surface treatments of chemical, electronic, mechanochemical and/or mechanical nature with compounds, such as amino acids, beeswax, fatty acids, fatty acid esters, fatty alcohols, anionic surfactants, lecithins, sodium, potassium, zinc, iron or aluminium salts of fatty acids, metal (titanium or aluminium) alkoxides, polyethylene, silicones, proteins (collagen or elastin), alkanolamines, silicon oxides, metal oxides, sodium hexametaphosphate, alumina or glycerol, hydrated silica, stearic acid, jojoba esters, or glutamic acid derivates, [0044] The treated nano pigments and non
  • titanium oxide nano pigments treated with a silicone are preferably TiO2 treated with octyltrimethylsilane, preferably for which the mean size of the elementary particles is from 25 to 40 nm; TiO2 treated with a polydimethylsiloxane, preferably for which the mean size of the elementary particles is 21 nm; or TiO2 treated 220084 with a polydimethylhydrogenosiloxane, preferably for which the mean size of the elementary particles is 25 nm.
  • the coated zinc oxide nano pigments and zinc oxide non-nano pigments are for example ZnO coated with polymethylhydrogenosiloxane; ZnO dispersions in cyclopolymethylsiloxane/ oxyethylenated polydimethylsiloxane, containing 30 % or 80 % of nano or non-nano zinc oxides coated with silica and polymethylhydrogenosiloxane; ZnO coated with perfluoroalkyl phosphate and copolymer based on perfluoroalkylethyl as a dispersion in cyclopentasiloxane; ZnO coated with silicone-grafted acrylic polymer, dispersed in cyclodimethylsiloxane; ZnO coated with triethoxycaprylylsilane; ZnO coated with polyhydroxystearic acid; alumina-treated ZnO dispersed in an ethylhexyl methoxycinnamate/PVP
  • particulate UV-filters or inorganic pigments which can optionally be hydrophobed, such as the oxides of iron (Fe2O3), zirconium (ZrO2), silicon (SiO2), manganese (e.g. MnO), aluminium (Al2O3), cerium (e.g. Ce2O3), barium carbonate (BaCO3), calcium carbonate (CaCO3), or mixtures thereof.
  • the at least one primary organic and/or inorganic UV-filter is selected from the group consisting of Camphor Benzalkonium Methosulfate, Homosalate, Benzophenone- 3, Phenylbenzimidazole Sulfonic Acid, Terephthalylidene Dicamphor Sulfonic Acid, Butyl Methoxydibenzoylmethane, Benzylidene Camphor Sulfonic Acid, Octocrylene, Polyacrylamidomethyl Benzylidene Camphor, Ethylhexyl Methoxycinnamate, PEG-25 PABA, Isoamyl p-Methoxycinnamate, Ethylhexyl Triazone, Drometrizole Trisiloxane, Diethylhexyl Butamido Triazone, 4-Methylbenzylidene Camphor, Ethylhexyl Salicylate, Ethylhexyl Dimethyl PABA, Benzophen
  • the at least one primary organic or inorganic UV-filter is selected from the group consisting of Camphor Benzalkonium Methosulfate, Benzophenone-3, Terephthalylidene Dicamphor Sulfonic Acid, Benzylidene Camphor Sulfonic Acid, Polyacrylamidomethyl Benzylidene Camphor, PEG-25 PABA, Drometrizole Trisiloxane, Ethylhexyl Dimethyl PABA, Benzophenone-4, Benzophenone-5, Methylene Bis- Benzotriazolyl Tetramethylbutylphenol, Polysilicone-15, Titanium Dioxide (nano), Tris- biphenyl triazine (nano), Phenylene Bis-Diphenyltriazine, Methoxypropylamino Cyclohexenylidene Ethoxyethylcyanoacetate, Bis-(Diethylaminohydroxybenzoyl Benzoyl) Pipe
  • the at least one primary organic or inorganic UV-filter is selected from the group consisting of Homosalate, Phenylbenzimidazole Sulfonic Acid, Butyl Methoxydibenzoylmethane, Octocrylene, Ethylhexyl Methoxycinnamate, Isoamyl p- Methoxycinnamate, Ethylhexyl Triazone, Diethylhexyl Butamido Triazone, 4- Methylbenzylidene Camphor, Ethylhexyl Salicylate, Disodium Phenyl Dibenzimidazole Tetrasulfonate, Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine, Titanium Dioxide, Diethylamino Hydroxy benzoyl Hexyl Benzoate, Zinc Oxide, Zinc Oxide (nano), Menthyl Anthranilate, and any mixture thereof
  • UV-filters cited before which can be used in the context of the present invention are preferred but naturally are not limiting.
  • the aforesaid primary organic or inorganic UV-filters are used in the sunscreen, cosmetic or pharmaceutical preparation or homecare product either as a single component or preferably in a mixture with two, three, four or more further of said UV- filters as specified above.
  • SPF SPF
  • the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention comprises at least two, more preferably at least three, most preferably at least four or even more different primary organic and/or inorganic UV-filters, i.e. in particular organic UV-filters and/or inorganic pigments (UV-filtering pigments).
  • Such compositions according to the invention are particularly suitable for protecting the skin and hair.
  • the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention comprises at least one UVA filter and at least one UVB filter.
  • Such sunscreen products, cosmetic or pharmaceutical preparations or homecare products according to the present invention provide broad spectrum photo protection, i.e. protection from both UVA and UVB.
  • the combination of effective sun protection UV-filters of different categories such as UVA filter, UVB, broadband filter, inorganic pigments provides reliable protection against the different UV rays in the wavelength range of 290 to 400 nm.
  • the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention comprises a combination with one, two, three or more broadband filters which are selected from the group consisting of 2-ethylhexyl-2-cyano-3,3-diphenyl acrylate, ethyl-2-cyano-3,3'- diphenyl acrylate, dihydroxy-4-methoxybenzophenone, 2,4-dihydroxybenzophenone, tetrahydroxy benzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2-hydroxy-4- n-octoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, sodium hydroxymethoxy benzophenone sulfonate, disodium-2,2'-dihydroxy-4,4'-dimethoxy-5,5'- disulfobenzophenone, phenol, 2-(2H-benzotriazol-2-yl)-4-methyl
  • the component (b) in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the first aspect of the present invention is at least one mycosporine-like amino acid compound represented either by the general formula (I) formula (I), as defined herein; or represented by the general formula (II) formula (II), as defined herein.
  • Mycosporine-like amino acids are small secondary metabolites produced by organisms that live in environments with high volumes of sunlight, usually marine environments.
  • the MAAs are imine derivatives of mycosporines and contain an amino-cyclohexene-imine ring linked to an amino acid, amino alcohol or amino group.
  • the compounds are capable of electron delocalization.
  • said compounds demonstrate antioxidant qualities.
  • compound(s) or “compound(s) of the present invention” refers to all compounds encompassed by the structural formula (I) and/or formula (lI) and/or formula (III) and/or formula (IV) disclosed herein and includes each subgenus and all specific compounds within the formula whose structure is disclosed herein.
  • the compounds may be identified by either their chemical structure and/or chemical name. When the chemical structure and chemical name are in conflict, the chemical structure determines the identity of the compound.
  • halogen residue/moiety or group alone or as part of another substituent according to the present invention refers to F, Cl, Br or I.
  • alkyl alone or as part of another substituent according to the present invention refers to a saturated or mono- or polyunsaturated linear or branched monovalent hydrocarbon radical obtained by removing a hydrogen atom from a single carbon atom of a corresponding parent alkane.
  • alkyl also includes any alkyl moieties in radicals derived therefrom, such as alkoxy, alkylthio, alkylsulphonyl saturated linear or branched hydrocarbon radicals having 1 to 10, 1 to 8, 1 to 6, or 1 to 4 carbon atoms.
  • alkyl radical is further bonded to another atom, it becomes an alkylene radical or alkylene group.
  • alkylene also refers to a divalent linear or branched alkyl.
  • -CH2CH3 is an ethyl
  • -CH2CH2- is an ethylene.
  • alkylene alone or as part of another substituent refers to a saturated linear or branched divalent hydrocarbon radical obtained by removing two hydrogen atoms from a single carbon atom or two different carbon atoms of a starting alkane.
  • the linear or branched alkyl group or alkylene group comprises 1 to 10 carbon atoms. In other still more preferred variants, the linear or branched alkyl group or alkylene group comprises 1 to 6 carbon atoms. [0069] More preferred according to the invention are saturated linear or branched C1 to C6 alkyl groups or saturated linear or branched C1 to C6 alkylene groups. [0070] Most preferred the linear or branched alkyl groups or alkylene groups with 1 to 4 carbon atoms.
  • Preferred alkyl radicals/moieties or alkyl groups include, but are not limited to: C1 to C6 alkyl comprising methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2- methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2- dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1- methylpentyl, 2- methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2- dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl
  • alkyl group or alkylene group as defined above may further be substituted.
  • alkyl or alkylene further includes radicals or groups having any degree of saturation, i.e., groups having only single carbon-carbon bonds ("alkyl” or 220084 "alkylene"), groups having one or more double carbon-carbon bonds (“alkenyl”), radicals having one or more triple carbon-carbon bonds (“alkynyl”), and groups having a mixture of single, double and/or triple carbon-carbon bonds.
  • the radical may be in either the cis or trans conformation around the double bond(s). So that the term “alkenyl” also includes the corresponding cis/trans isomers.
  • the linear or branched alkenyl group comprises 2 to 10 carbon atoms. In other preferred variants, the linear or branched alkenyl group comprises 2 to 6 carbon atoms.
  • the linear or branched alkenyl group comprises 2 to 4 carbon atoms.
  • Preferred according to the invention are mono- or di-unsaturated linear or branched C1 to C6 alkenyl groups.
  • Typical alkenyl radicals or alkenyl groups include, but are not limited to, ethenyl; propenyls such as prop-1-en-1-yl, prop-1-en-2-yl, prop-2-en-1-yl (allyl), prop-2-en-2-yl, cycloprop-1-en-1-yl, cycloprop-2-en-1-yl; butenyls such as but-1-en-1-yl, but-1-en-2-yl, 2- methyl-prop-1-en-1-yl, but-2-en-1-yl, but-2-en-2-yl, buta-1,3-dien-1-yl, buta-1,3-dien-2-yl and the like.
  • alkenyl group as defined above may further be substituted.
  • alkynyl alone or as part of another substituent according to the present invention refers to an unsaturated linear or branched monovalent hydrocarbon radical having at least one carbon-carbon triple bond (C ⁇ C triple bond). 220084 [0081]
  • the linear or branched alkynyl group comprises 2 to 10 carbon atoms.
  • the alkynyl group comprises 2 to 6 carbon atoms.
  • the alkynyl group comprises 2 to 4 carbon atoms.
  • alkynyl radicals/moieties or alkynyl groups include, but are not limited to, ethynyl; propynyls such as prop-1-yn-1-yl, prop-2-in-1-yl, etc.; butynyls such as but-1-in- 1-yl, but-1-in-3-yl, but-3-in-1-yl, and the like.
  • the alkynyl group as defined above may further be substituted.
  • the alkyl group or alkylene group as defined above may further be substituted.
  • alkoxy alone or as part of another substituent according to the present invention refers to a linear or branched radical of the formula -O-R, where R is alkyl or substituted alkyl, as defined herein.
  • the linear or branched alkoxy group comprises 2 to 10 carbon atoms.
  • the linear or branched alkoxy group comprises 2 to 6 carbon atoms.
  • the linear or branched alkoxy group comprises 2 to 4 carbon atoms.
  • Most preferred according to the invention are linear or branched C1 to C6 alkoxy groups.
  • Typical alkoxy radicals/moieties or alkoxy groups include C1 to C6 alkoxy comprising C1 to C4 alkoxy such as. methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy; as well as pentoxy, 1- methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2- dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2- 220084 methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2- dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3- dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2- trimethylpropoxy
  • the alkoxy radical or alkoxy group is 2-allyloxyethoxy.
  • the alkoxy group or alkylene group as defined above may further be substituted.
  • alkylthio or “thioalkoxy” alone or as part of another substituent according to the present invention refers to a radical of the formula -S-R, wherein R is alkyl or substituted alkyl, as defined herein.
  • alkyl or alkylene also includes heteroalkyl radicals or heteroalkyl groups.
  • heteroalkyl by itself or as part of other substituents refers to alkyl groups in which one or more of the carbon atom(s) is/are independently replaced by the same or another heteroatom or by the same or another heteroatomic group(s).
  • Typical heteroatoms or heteroatomic groups that may replace the carbon atoms include, but are not limited to, -O-, -S-, -N-, -Si-, -NH-, -S(O)- , -S(O)2-, -S(O)NH-, -S(O)2NH-, and the like, and combinations thereof.
  • the heteroatoms or heteroatomic groups may be located at any internal position of the alkyl group.
  • alkyl group or alkylene group as defined above may further be substituted.
  • cycloalkyl alone or as part of another substituent according to the present invention refers to a saturated or mono- or polyunsaturated, non-aromatic, cyclic monovalent hydrocarbon radical in which the carbon atoms are ring-linked and which has no heteroatom.
  • the carbon ring can occur as a monocyclic compound, which has only a single ring, or as a polycyclic compound, which has two or more rings.
  • the term "cycloalkyl" includes a three- to ten- membered monocyclic cycloalkyl radical or cycloalkyl group or a nine- to twelve- membered polycyclic cycloalkyl radical or cycloalkyl group.
  • the cycloalkyl moiety comprises a five-, six- or seven-membered monocyclic cycloalkyl moiety or a nine- to twelve-membered bicyclic cycloalkyl moiety.
  • a cycloalkyl radical or group comprises 3 to 20 carbon atoms. In an even more preferred embodiment, a cycloalkyl radical comprises 6 to 15 carbon atoms. In a most preferred embodiment, a cycloalkyl radical comprises 6 to 10 carbon atoms. Most preferred are monocyclic C3 to C7 cycloalkyl groups.
  • Typical cycloalkyl radicals or cycloalkyl groups include, but are not limited to, saturated carbocyclic radicals having 3 to 20 carbon atoms, such as C3 to C12 carbocyclyl, comprising cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, and cyclododecyl; cyclopentyl, cyclohexyl, cycloheptyl, as well as cyclopropyl-methyl, cyclopropyl-ethyl, cyclobutyl- methyl, cyclobutyl-ethyl, cyclopentyl-methyl, cyclopentyl-ethyl, cyclohexyl-methyl, or C3- to C7-carb
  • cycloalkyl radicals or cycloalkyl groups preferred according to the invention include but are not limited to naphthyl, indenyl groups and the like.
  • cycloalkenyls are compounds with one, two or more double bond(s), where the number of possible, mostly conjugated double bonds in the molecule depends on the ring size.
  • Typical cycloalkenyls include, but are not limited to, cyclopropenyl, cyclopentenyl, cyclohexenyl, cyclopentadienyl, and the like.
  • cycloalkyl further includes cycloalkynyls, i.e. unsaturated, -C ⁇ C-triple bonds, containing cyclic hydrocarbon radicals between two carbon atoms of the ring molecule, the triple bond depending on the ring size for reasons of ring tension.
  • Typical cycloalkynyles include cyclooctin.
  • aryl alone or as part of another substituent according to the present invention refers to a monovalent aromatic hydrocarbon radical derived by removing a hydrogen atom from a single carbon atom of an aromatic ring SY-stem.
  • aryl includes a three- to ten-membered monocyclic aryl radical or aryl group or a nine- to twelve-membered polycyclic aryl radical or aryl group.
  • the carboaryl radical comprises a five- , six- or seven-membered monocyclic carboaryl radical or a nine- to twelve-membered bicyclic carboaryl radical.
  • the aryl radical comprises 3 to 20 carbon atoms.
  • the aryl moiety comprises 6 to 15 ring atoms.
  • an aryl radical comprises 6 to 10 carbon atoms.
  • Most preferred according to the invention are monocyclic C3 to C10 aryl groups. Most preferred are monocyclic C3 to C7 aryl groups.
  • Typical aryl radicals include, without being limited thereto, benzene, phenyl, biphenyl, naphthyl such as 1- or 2-naphthyl, tetrahydronaphthyl, fluorenyl, indenyl, and phenanthrenyl.
  • Typical carboaryl moieties further include, but are not limited to, groups derived from aceanthrylene, acenaphthylene, acephenanthrylene, anthracene, azulene, benzene, chrysene, corone, fluoranthene, fluorene, hexacene, hexaphene, hexalene, as- indacene, S-indacene, indane, indene, naphthalene, octacene, octaphene, octalene, ovalene, penta-2,4-diene, pentacene, pentalene, pentaphene, perylene, phenalene, phenanthrene, picene, pleiadene, pyrene, pyranthrene, rubicene, triphenylene, trinaphthalene and the like.
  • Aromatic polycyclic aryl radicals or aryl groups preferred according to the invention include, but are not limited to, naphthalene, biphenyl and the like.
  • the aryl moiety or group, as defined above, may further be substituted.
  • 220084 [0115]
  • arylalkyl alone or as part of another substituent according to the present invention refers to an acyclic alkyl group in which one of the hydrogen atoms attached to a carbon atom, typically a terminal or sp carbon atom, is replaced by an aryl group as defined herein. In other words, arylalkyl may also be considered as alkyl substituted by aryl.
  • Typical arylalkyl groups include, but are not limited to, benzyl, 2- phenylethan-1-yl, 2-phenylethen-1-yl, naphthylmethyl, 2-naphthylethan-1-yl, 2- naphthylethen-1-yl, naphthobenzyl, 2-naphthophenylethan-1-yl, and the like.
  • heteroarylalkyl alone or as part of another substituent refers to a cyclic alkyl group in which one of the hydrogen atoms attached to a carbon atom is replaced by a heteroaryl group.
  • the heteroarylalkyl group is a 6- to 20-membered heteroarylalkyl, e.g., the alkyl, alkenyl, or alkynyl group of the heteroarylalkyl is a C1- to C6-alkyl and the heteroaryl group is a 5- to 15-membered heteroaryl group.
  • the heteroarylalkyl is a 6- to 13-membered heteroarylalkyl, e.g., the alkyl, alkenyl, or alkynyl group is a C1- to C3-alkyl and the heteroaryl group is a 5 to 10-membered heteroaryl.
  • heterocycloalkyl alone or as part of another substituent according to the present invention refers to a saturated or mono- or polyunsaturated, non-aromatic, cyclic monovalent hydrocarbon radical in which one or more carbon atom(s) is/are independently replaced by the same or a different heteroatom.
  • Typical heteroatoms to replace the carbon atom(s) include, but are not limited to, N, P, O, S, Si, etc.
  • heterocycloalkyl groups include, without being limited thereto, groups derived from epoxides, azirines, thiiranes, imidazolidine, morpholine, piperazine, piperidine, pyrazolidine, pyrrolidone, quinuclidine and the like.
  • the "heterocycloalkyl" moiety or group comprises 3 to 20 ring atoms.
  • the heterocycloalkyl moiety comprises 6 to 15 ring atoms.
  • the heterocycloalkyl moiety comprises 6 to 10 carbon atoms.
  • heterocycloalkyl moiety can occur as a monocyclic compound, which has only a single ring, or as a polycyclic compound, which has two or more rings, such as bicyclic, tricyclic or spirocyclic.
  • heterocycloalkyl includes three- to seven-membered, saturated or mono- or polyunsaturated heterocycloalkyl moieties comprising one, two, three or four heteroatoms selected from the group consisting of O, N and S. The heteroatom or heteroatoms may occupy any position in the heterocycloalkyl ring.
  • heterocycloalkyl includes a three- to ten- membered monocyclic heterocycloalkyl radical or a nine- to twelve-membered polycyclic heterocycloalkyl radical.
  • the heterocycloalkyl moiety comprises a five-, six- or seven-membered monocyclic heterocycloalkyl moiety or a nine- to twelve-membered bicyclic heterocycloalkyl moiety.
  • the "heterocycloalkyl" moiety or group comprises 3 to 20 ring atoms.
  • the heterocycloalkyl moiety comprises 6 to 15 ring atoms. In an even more preferred embodiment, the heterocycloalkyl moiety comprises 6 to 10 carbon atoms. [0123] Most preferred according to the invention are monocyclic heterocycloalkyl radicals comprising 3 to 12 carbon atoms. Most preferred are monocyclic heterocycloalkyl radicals having 5 to 7 ring atoms.
  • Typical heterocycloalkyl moieties include, but are not limited to: Five- or six- membered, saturated or monounsaturated heterocycloalkyl containing one or two nitrogen atoms and/or one oxygen or sulphur atom or one or two oxygen and/or sulphur atoms as ring members comprising 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2- tetrahydrothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3- lsoxazolidinyl, 4-lsoxazolidinyl, 5-lsoxazolidinyl, 3-lsothiazolidinyl, 4-lsothiazolidinyl, 5- lsothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl,
  • heterocycloalkyl moiety or group, as defined above, may further be substituted.
  • heteroaryl by itself or as part of another substituent according to the present invention refers to a monovalent heteroaromatic radical obtained by removing a hydrogen atom from a single atom of a heteroaromatic ring SY-stem. Typical heteroaryl radicals, or.
  • Heteroaryl groups include, but are not limited to, those derived from acridine, ⁇ -carboline, chroman, chromium, cinnoline, furan, imidazole, indazole, indole, indoline, indolizine, isobenzofuran, isochromium, isoindole, isoindoline, isoquinoline, isothiazole, isoxazole, naphthyridine, oxadiazole, oxazole, perimidine, phenanthridine, phenanthroline, phenazine, phthalazine, pteridine, purine, pyran, pyrazine, pyrazole, pyridazine, pyridine, pyrimidine, pyrrole, thiazole, thiophene, triazole, xanthene and the like are derived.
  • heteroaryl moiety can occur as a monocyclic compound having only a single ring or as a polycyclic compound having two or more rings.
  • heteroaryl includes a three- to ten- membered monocyclic heteroaryl radical or a nine- to twelve-membered polycyclic heteroaryl radical.
  • the heteroaryl moiety comprises a five-, six- or seven-membered monocyclic heteroaryl moiety or a nine- to twelve- membered bicyclic heteroaryl moiety.
  • heteroaryl includes three- to seven-membered monocyclic heteroaryl radicals comprising one, two, three or four heteroatoms selected from the 220084 group consisting of O, N and S.
  • the heteroatom or heteroatoms may occupy any position in the heteroaryl ring.
  • the heteroaryl moiety or group comprises 3 to 20 ring atoms.
  • the heteroaryl moiety comprises 6 to 15 ring atoms.
  • the heteroaryl group comprises 6 to 10 ring atoms.
  • Most preferred according to the invention are monocyclic C3 to C7 heteroaryl groups.
  • heteroaryl moieties or heteroaryl groups include, but are not limited to, those derived from furan, thiophene, pyrrole, benzothiophene, benzofuran, benzimidazole, indole, pyridine, pyrazole, quinoline, imidazole, oxazole, isoxazole, and pyrazine.
  • Five-membered aromatic heteroaryl radicals containing, in addition to carbon atoms, one, two or three nitrogen atoms or one or two nitrogen atoms and one sulfur or oxygen atom as ring atoms include 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3- pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2- thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-lmidazolyl, 4-lmidazolyl, and 1,3,4-triazol-2-yl.
  • Five-membered aromatic heteroaryl radicals containing one, two, three or four nitrogen atoms as ring atoms include 1-, 2- or 3-pyrrolyl, 1-, 3- or 4-pyrazolyl, 1-, 2- or 4- lmidazolyl, 1,2,3-[1H]-triazol-1-yl, 1,2,3-[2H]-triazol-2-yl, 1,2,3-[1H]-triazol-4-yl, 1,2,3- [1H]-triazol-5-yl, 1,2,3-[2H]-triazol-4-yl, 1,2,4-[1H]-triazol-1-yl, 1,2,4-[1H]-triazol-3-yl, 1,2,4-[1H]-triazol-5-yl, 1,2,4-[4H]-triazol-4-yl, 1,2,4-[4H]-triazol-3-yl, [1H]-tetrazol-1-yl, [1H]
  • Five-membered aromatic heteroaryl radicals containing a heteroatom selected from oxygen or sulphur and optionally one, two or three nitrogen atoms as ring atoms include 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 3- or 4-lsoxazolyl, 3- or 4-isothiazolyl, 2-, 4- or 5-oxazolyl, 2-, 4- or 5-thiazolyl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4- thiadiazol-2-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and 1,3,4-oxadiazol-2-yl.
  • C-spirocycles in the context of the present application means compounds that have at least two molecular rings with only one common atom.
  • the simplest spiro compounds are bicyclic (having just two rings) or have a bicyclic portion as part of the larger ring system, in either case with the two rings connected through the defining single common atom.
  • the one common atom connecting the participating rings distinguishes spiro compounds from other bicyclic structures: from isolated ring compounds like biphenyl that have no connecting atoms, from fused ring compounds like decalin having two rings linked by two adjacent atoms, and from bridged ring compounds like norbornane with two rings linked by two non-adjacent atoms.
  • Spiro compounds may be fully carbocyclic (all carbon) or heterocyclic (having one or more non- carbon atom, such as N, O and S).
  • the common atom that connects the two (or sometimes three) rings is called the spiro atom.
  • the spiro atom is a carbon atom.
  • the C-spirocycles compound means compounds that are fully carbocyclic (all carbon).
  • substituted in the context of the present invention means that one or more hydrogen atoms of the indicated radical or group is/are independently replaced by the same or a different substituent(s). Additionally, the term “substituted” specifically provides for one or more, i.e., two, three, four, five, six or more, substitutions commonly used in the art. However, it is generally known that the substituents should be selected so that they do not adversely affect the useful properties of the compound or its function.
  • Suitable substituents in the context of the present invention preferably include halogen groups, perfluoroalkyl groups, perfluoroalkoxy groups, alkyl groups, alkenyl groups, alkynyl groups, hydroxy groups, oxo groups, mercapto groups, alkylthio groups, alkoxy groups, aryl or heteroaryl groups, aryloxy groups or heteroaryloxy groups, arylalkyl or heteroarylalkyl groups, arylalkoxy or heteroarylalkoxy groups, amino groups, alkyl and dialkylamino groups, carbamoyl groups, alkylcarbonyl groups, carboxyl groups, alkoxycarbonyl groups, alkylaminocarbonyl groups, dialkylaminocarbonyl groups, arylcarbonyl groups, aryloxycarbonyl groups, alkylsulfonyl groups, arylsulfonyl groups, cycloalkyl groups, cyano groups,
  • Substituents or substituent groups useful for substituting saturated carbon atoms in the indicated group or radical more preferably include, but are not limited to, halogen, hydroxyl, alkyl, alkenyl, alkynyl, alkoxyl, -NH2, amino (primary, secondary, or tertiary), nitro, thiol, thioether, imine, cyano, amido, phosphonato, phosphine, carboxyl, thiocarbonyl, sulfonyl, sulfonamide, ketone, aldehyde, ester, acetyl, acetoxy, carbamoyl, oxygen (O); haloalkyl (e.g., trifluoromethyl); aminoacyl and aminoalkyl, carbocyclic cycloalkyl, which may be monocyclic or fused or non-fused polycyclic (e.g., cyclopropyl, cyclobutyl
  • pyrrolidinyl piperidinyl, piperazinyl, morpholinyl, or thiazinyl
  • carbocyclic or heterocyclic monocyclic or fused or non-fused polycyclic aryl (e.g., phenyl, naphthyl, pyrrolyl, indolyl, furanyl, thiophenyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, quinolinyl, isoquinolinyl, acridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, benzimidazolyl, benzothiophenyl, or benzofuranyl), -CO2CH3, -CONH2, -OCH2CONH2; -SO2NH2, -OCHF2, -CF3,
  • the substituents used to replace a particular radical or radical may in turn be further substituted, typically with one or more of the same or different radicals selected from the various groups indicated above and as defined in detail above.
  • substituted combinations such as substituted arylalkyl
  • either 220084 the aryl or the alkyl group may be substituted, or both the aryl and the alkyl group may be substituted with one or more substituents.
  • the mycosporine-like amino acid compound (b) of general formula (I) is either an acid compound or an ester compound represented by the general formula (III) formula (III), wherein R’, R1’, R2’ and R3’ have the same meaning as defined above for general formula (I); or is an amide compound represented by the general formula (IV) formula (IV), wherein R’, R1’, amide’ and R3’ have the same meaning as defined above for general formula (I).
  • the amide’ is NH2.
  • the mycosporine-like amino acid compound (b) is an acid compound represented by the general formula (III-acid), wherein R’, R1’ and R3’ have the same meaning as defined above for general formula (I) formula (III-acid), [0145]
  • Such mycosporine-like amino acid compounds are particularly photo-stable and temperature-stable compounds and show stability in pH solution or in different emulsion types and do not degrade.
  • R’ or in the general formula (II) R” is selected from the group consisting of unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted , unsubstituted or substituted , unsubstituted or substituted , unsubstituted or substituted , unsubstituted or substituted , unsubstituted or substituted , unsubstituted or substituted , and unsubstituted or substituted , 220084 wherein the dotted line designates the binding site to the cyclohexene-imine ring.
  • in the general formula (I) R’ or in the general formula (II) R” is an unsubstituted or substituted alkenyl.
  • in the general formula (I) R’ or in the general formula (II) R” is an unsubstituted or substituted alkynyl.
  • formula (III) or formula (IV) R’ or in the general formula (II) R” is an unsubstituted or substituted .
  • mycosporine-like amino acid compound according to general formula (I), formula (III) or formula (IV) wherein R’ is an unsubstituted or substituted .
  • the mycosporine-like amino acid compound (b) is represented either by the general formula (V) 220084 formula (V), wherein - R1’, Z and R3’ have the same meaning as defined above for general formula (I); - R4’, R5’ and R6’ which may be identical or different, are independently from each other selected from the group consisting of H, OH, halogen, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted alkoxy, unsubstituted or substituted alkylthio, unsubstituted or substituted alkanoyl/acyl R
  • the mycosporine-like amino acid compound is a compound according to general formula (I), formula (III) or formula (IV), wherein - R’ is unsubstituted or substituted phenyl; and/or - Z is -O-R2’ or amide’; and/or - R1’ is selected from the group consisting of CH2, C(methyl)2, O, S, SO, SO2, NH and N(alkyl); and/or - R2’ is selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, , , , (2-ethyl- hexyl) and phenyl; and/or - amide’ is selected from the group consisting of NH2, NHalkyl, N(alkyl)2, -N(O- alkyl)(alky
  • the mycosporine-like amino acid is a compound according to general formula (I), formula (III) or formula (IV), wherein R4’, R5’ and R6’ which may be identical or different, are independently from each other selected from the group consisting of H, OH, methyl, ethyl, iso-propyl, tert.-butyl, and O-methyl.
  • the mycosporine-like amino acid compound is a compound according to general formula (II) or formula (VI), wherein R4”, R5” and R6” which may be identical or different, are independently from each other selected from the group consisting of H, OH, methyl, ethyl, iso-propyl, tert.-butyl and O-methyl.
  • R4”, R5” and R6 which may be identical or different, are independently from each other selected from the group consisting of H, OH, methyl, ethyl, iso-propyl, tert.-butyl and O-methyl.
  • the substituted phenyl bonded to the imino functionality is selected from the group consisting of wherein the dotted line designates the binding site to the cyclohexene-imine ring.
  • the mycosporine-like amino acid compound is a compound according to general formula (II) or formula (VI), wherein X is S.
  • mycosporine-like amino acid compounds considerably improve the water resistance of a sunscreen product, cosmetic or pharmaceutical preparation or homecare 220084 product comprising a primary organic and/or inorganic UV-filter, and, thus, improve the SPF of the formulation.
  • n is 1.
  • the mycosporine-like amino acid compound (b) is represented by the general formula (A) formula (A), wherein R1’, R3’, R4’, R5’ and R6’ have the same meaning as defined above for general formula (V).
  • the mycosporine-like amino acid compound (b) of general formula (I) is either an acid compound or an ester compound represented by the general formula (VII) formula (VII), 220084 wherein R1’, R2’, R3’, R4’, R5’ and R6’ have the same meaning as defined above for general formula (V).
  • the mycosporine-like amino acid compound (b) is an acid compound represented by the general formula (VII-acid) formula (VII-acid), wherein R1’, R3’, R4’, R5’ and R6’ have the same meaning as defined above for general formula (V).
  • Such mycosporine-like amino acid compounds are particularly photo-stable and temperature-stable compounds and show stability in pH solution or in different emulsion types and do not degrade.
  • the mycosporine-like amino acid compound (b) is an ester compound represented by the general formula (VII-ester) formula (VII-ester), 220084 wherein R1’, R3’, R4’, R5’ and R6’ have the same meaning as defined above for general formula (V).
  • the alkyl residue in the formula (VII-ester) is methyl or ethyl or propyl or butyl. Most preferred the alkyl residue in the formula (VII-ester) is methyl.
  • ester compounds are particularly stable.
  • the mycosporine-like amino acid compound (b) is an amide compound represented by the general formula (VIII) formula (VIII), wherein R1’, amide’, R3’, R4’, R5’ and R6’ have the same meaning as defined above for general formula (V).
  • the mycosporine-like amino acid compound (b) is an amide compound represented by the general formula (VIII-amide) formula (VIII-amide), 220084 wherein R1’, R3’, R4’, R5’ and R6’ have the same meaning as defined above for general formula (V) and R11’ and R12’ are independently from each other selected from the group consisting of H, OH and alkyl.
  • the R11’ alkyl and R12’ alkyl in the formula (VIII- amide) are independently from each other selected from methyl, ethyl, propyl or butyl.
  • R11’ and R12’ in the formula (VIII-amide) are each H or each methyl.
  • the mycosporine-like amino acid compound (b) is a Weinreb amide compound represented by the general formula (VIII-Weinreb amide) formula (VIII-Weinreb amide), wherein R1’, R3’, R4’, R5’ and R6’ have the same meaning as defined above for general formula (V).
  • the alkyl residue in the formula (VIII-Weinreb amide) is selected from the group consisting of methyl, ethyl, propy.
  • the mycosporine-like amino acid compound (b) is a hydroxamate compound represented by the general formula (VIII- hydroxamate derivative) 220084 R6 ⁇ formula (VIII-hydroxamate derivative), wherein R1’, R3’, R4’, R5’ and R6’ have the same meaning as defined above for general formula (V).
  • the amide compound (VIII-amide) the mycosporine-like amino acid compound (b) is an alkylated hydroxamate derivative represented by the general formula (VIII-alkylated hydroxamate derivative) R6 ⁇ formula (VIII-alkylated hydroxamate derivative), wherein R1’, R3’, R4’, R5’ and R6’ have the same meaning as defined above for general formula (V).
  • the alkyl residue in the formula (VIII-alkylated hydroxamate derivative) is selected from the group consisting of methyl, ethyl, propyl and butyl, more preferred the alkyl is methyl.
  • the mycosporine-like amino acid compound (b) is an alcohol compound represented by the general formula (IX-alcohol) 220084 formula (IX-alcohol), wherein R1”, X, R4”, R5” and R6” have the same meaning as defined above for general formula (VI).
  • the mycosporine-like amino acid compound (b) is an acid compound represented by the general formula (IX-acid) formula (IX-acid), wherein R1”, X, R4”, R5” and R6” have the same meaning as defined above for general formula (VI).
  • the mycosporine-like amino acid compound (b) is an ester compound represented by the general formula (VII-ester) formula (IX-ester), 220084 wherein R1”, X, R4”, R5” and R6” have the same meaning as defined above for general formula (VI).
  • the alkyl residue in the formula (VII-ester) is methyl or ethyl or propyl or butyl, more preferred the alkyl residue is methyl.
  • the mycosporine-like amino acid compound (b) is an amide compound represented by the general formula (X) R 6 ⁇ ⁇ formula (X), wherein R1”, amide”, X, R4”, R5” and R6” have the same meaning as defined above for general formula (VI).
  • the mycosporine-like amino acid compound (b) is an amide compound represented by the general formula (X-amide), R6 ⁇ ⁇ formula (X-amide), 220084 wherein R1”, X, R4”, R5” and R6” have the same meaning as defined above for general formula (VI) and R11” and R12” are independently from each other selected from the group consisting of H, OH and alkyl.
  • R11” alkyl and R12” alkyl in the formula (X-amide) is methyl or ethyl or propyl or butyl.
  • R11’ and R12’ in the formula (X-amide) are each H or each ethyl.
  • the mycosporine-like amino acid compound (b) is a Weinreb amide compound represented by the general formula (X-Weinreb amide) R6 ⁇ ⁇ formula (X-Weinreb amide), wherein R1”, X, R4”, R5” and R6” have the same meaning as defined above for general formula (VI).
  • the alkyl residue in the formula (X-Weinreb amide) is selected from the group consisting of methyl, ethyl, propyl and butyl, more preferred the alkyl residue is methyl.
  • the mycosporine-like amino acid compound (b) is a hydroxamate derivative represented by the general formula (X- hydroxamate acid derivative) 220084 R6 ⁇ ⁇ formula (X-hydroxamate derivative), wherein R1”, X, R4”, R5” and R6” have the same meaning as defined above for general formula (VI)
  • the amide compound (VIII-amide) the mycosporine-like amino acid compound (b) is an alkylated hydroxamate derivative represented by the general formula (VIII-alkylated hydroxamate derivative) formula (X-alkylated hydroxamate derivative), wherein R1”, X, R4”, R5” and R6” have the same meaning as defined above for general formula (VI).
  • the alkyl residue in formula (X-alkylated hydroxamate derivative) is selected from the group consisting of methyl, ethyl, propyl and butyl, more preferred the alkyl residue is methyl.
  • the sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprises at least one mycosporine-like amino acid compound selected from the group consisting of the 220084 following compounds I-1 to I-128 according to the general formula (I) and II-1 to II-192 according to the general formula (II): Table 1: 220084 220084 220084 220084 220084 220084 220084 220084 220084 220084 or a tautomer or a salt thereof, or any mixture of the afore-said compounds.
  • phenyl may be unsubstituted or substituted as defined herein, and R2’, amide’, Y, amide“ and alkyl have the same meaning as defined above.
  • R2’ is selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, , , , (2-ethylhexyl) and phenyl;
  • amide’ is selected from the group consisting of NH2, NHalkyl, N(alkyl)2, -N(O-alkyl)(alkyl) (Weinreb amide) and -N(OH)(H) (hydroxamate);
  • Y is selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, , , , (2-ethylhexyl) and phenyl;
  • amide” is selected from the group consisting of the group consisting
  • the sunscreen product of cosmetic or pharmaceutical preparation comprises at least one mycosporine-like amino acid compound selected from the group consisting of: 220084 Table 2: 220084 220084 or a tautomer or a salt thereof, or any mixture of the afore-said compounds.
  • the compounds MAA-2 salt and MAA-9 acid are particularly preferred, since they have a pronounced water resistance improving effect.
  • MAA-9 is particularly preferred.
  • Said compound having an acid functionality is photo-stable and temperature-stable and show stability in pH solution or in oil-in-water emulsions and does not degrade.
  • the sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprises at least one mycosporine-like amino acid compound selected from the group consisting of: MAA-12: , 220084 MAA-13: , or a tautomer or a salt thereof, or any mixture of the afore-said compounds, wherein alkyl is preferably either methyl or ethyl or propyl or butyl, most preferred methyl.
  • Said most preferred mycosporine-like amino acid compounds are used either as single substance or in a mixture with one, two or more different mycosporine-like amino acid compounds as defined herein.
  • the sunscreen product or cosmetic or pharmaceutical composition according to the first aspect of the present invention is further characterized in that it does not contain one or more of the following mycosporine-like amino acid compounds: 220084 (R,E)-8-((4-methoxyphenylimino)-6,6-dimethyl- 3,4,4,6,7- hexahydro-2H-benzo[b][1,4] thiazine-3-carboxylic acid (CAS1629023-04-06); IUPAC: 8-(4-methoxyanilino)-6,6- dimethyl-2,3,5,7-tetrahydro-1,4-benzothiazine-3-carboxylic acid; IUPAC: Ethyl 2-[[(3E)-3-(4-methoxyphenyl)imino-5,5-dimethyl-cyclohexen-1- yl]amino]acetate SY-20: 6,6-dimethyl-8((4-(octyloxy)pheny
  • Various mycosporine-like amino acid compounds (b) as described herein contain one or more chiral centers, and, thus, can exist as racemic mixtures of enantiomers, mixtures of diastereomers or enantiomerically or optically pure compounds. It should also be noted the compounds of the invention include E and Z isomers, or a mixture thereof, and cis and trans isomers or a mixture thereof. [0206] Accordingly, the chemical structures of general formulae (I) to (X) and compounds explicitly disclosed herein include all possible enantiomers and diastereomers or stereoisomers.
  • the mycosporine-like amind acid compounds (b) of the invention are isolated as either the E or Z isomer. In other embodiments, the compounds of the invention are a mixture of the E and Z isomers.
  • stereomerically pure compounds are used in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention. As used herein and unless otherwise indicated, the term "stereomerically pure" means that one stereoisomer of a compound is substantially free of other stereoisomers of that compound or one geometric isomer (e.g., about a double bond) is substantially free of the other geometric isomer.
  • a stereomerically pure compound of the invention having one chiral centre will be substantially free of the opposite enantiomer of the compound.
  • a stereomerically pure compound of the invention having two chiral centres, or a composition thereof will be substantially free of other diastereomers of the compound.
  • a stereomerically pure compound of the invention having a double bond capable of E/Z isomerism, or a composition thereof, will be substantially free of one of the E/Z isomers.
  • a typical stereomerically pure compound comprises greater than about 80 % by weight of one stereoisomer or E/Z isomer of the compound and less than about 20 % by weight of other stereoisomers or E/Z isomer of the compound, more preferably greater than about 90 % by weight of one stereoisomer or E/Z isomer of the compound and less than about 10 % by weight of the other stereoisomers or E/Z isomer of the compound, 220084 even more preferably greater than about 95 % by weight of one stereoisomer or E/Z isomer of the compound and less than about 5 % by weight of the other stereoisomers or E/Z isomer of the compound, and most preferably greater than about 97 % by weight of one stereoisomer or E/Z isomer of the compound and less than about 3 % by weight of the other stereoisomers or E/Z isomer of the compound.
  • stereomerically enriched means a compound of the invention, or a composition thereof, that comprises greater than about 60 % by weight of one stereoisomer or E/Z isomer of a compound of the invention, preferably greater than about 70 % by weight, more preferably greater than about 80 % by weight of one stereoisomer or E/Z isomer of a compound of the invention.
  • mycosporine-like amino acid compound according to formulae (I) to (X) as well as individual mycosporine- like amino acid compounds specified herein, are to be interpreted as encompassing racemic mixtures of enantiomers, mixtures of diastereomers or enantiomerically or optically pure compounds.
  • the compounds according to general formulae (I) to (X) are in equilibrium with their tautomer structures, in which the hydrogen of the amino group changes its places with the double bond of the cyclohexene ring.
  • Tautomerism is defined as each of two or more isomers of a compound which exist together in equilibrium and are readily interchanged by migration of an atom or group within the molecule. Tautomeric pure or enriched systems will readily interchange into the equilibrium state over time.
  • the tautomers of general formula (I) are represented by general formulae (I-tau): 220084 formula (I) formula (I-tau).
  • the tautomers of general formula (II) are represented by general formula (II-tau): ⁇ formula (II) formula (II-tau).
  • the mycosporine-like amino acid compounds according to formulae (I) to (X) as well as individual mycosporine-like amino acid compounds specified herein are used according to the first aspect of the present invention either in neutral, i.e. uncharged form, or in the form of their salts, such as an acid addition salt, with inorganic or organic acids.
  • salt in the context of the present invention refers to a salt of a compound that possesses the desired effect or pharmacological activity of the parent compound.
  • Such salts include: (1) acid addition salts formed with inorganic acids, or formed with organic acids, preferably monovalent or polyvalent carboxylic acids; or (2) salts formed when an acidic proton present in the starting compound is replaced by a metal ion, e.g., an alkali metal ion, an alkaline earth ion, or an aluminium ion; or coordinated with an organic base.
  • acid addition salts are again particularly preferred, since the mycosporine-like amino acid compounds according to the general formulae (I) to (X) or the mycosporine-like amino acid compounds specified herein comprise a protonable N atom.
  • the inorganic acids that form acid addition salts with the mycosporine-line amino acid compound are preferably selected from the group consisting of hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid and the like. Particularly preferred is the hydrochloride salt or the sulphate salt or the phosphate salt. [0222] Even more preferred are acid addition salts with organic mono- or polycarboxylic acids. Further preferred are acid addition salts with organic mono- or polycarboxylic acids, wherein the carboxylic acid is selected from saturated or mono- or polyunsaturated C1 to C30 monocarboxylic acids, saturated or mono- or polyunsaturated C3 to 10 di- or tricarboxylic acids.
  • the carboxylic acid may be mono- or poly-substituted with hydroxy groups, preferably ⁇ -hydroxycarboxylic acids in which the hydroxy group is located on the carbon atom adjacent to the carboxy group.
  • hydroxy groups preferably ⁇ -hydroxycarboxylic acids in which the hydroxy group is located on the carbon atom adjacent to the carboxy group.
  • ⁇ -hydroxycarboxylic acids are malic acid, citric acid, 2- hydroxy-4-methylmercaptobutyric acid, glycolic acid, isocitric acid, mandelic acid, lactic acid, tartronic acid, or tartaric acid.
  • the organic acids that form acid addition salts with the mycosporine-like amino acid compound are preferably selected from the group consisting of amino acids, acetic 220084 acid, trifluoroacetic acid, propionic acid, hexanoic acid, cyclopentane propionic acid, glycolic acid, pyruvic acid, lactic acid, malonic acid, oxalic acid, succinic acid, malic acid, maleic acid, fumaric acid, tartaric acid, citric acid, benzoic acid, 3-(4- hydroxybenzoyl)benzoic acid, cinnamic acid, mandelic acid, methanesulfonic acid, ethanesulfonic acid, 1,2-ethanedisulfonic acid, 2-hydroxyethanesulfonic acid, benzenesulfonic acid, 4-chlorobenzenesulfonic acid, 2-naphthalenesulfonic acid, 4- toluenesulfonic acid, camphors
  • the metal ions for salt formation that replace an acidic proton present in the starting compound are selected from the group consisting of alkali metal ions, preferably Na+ or K+, alkaline earth metal ions, preferably Ca++, Mg++, and Al+++.
  • the coordinating organic base for salt formation is selected from the group consisting of ethanolamine, diethanolamine, triethanolamine, N-methylglucamine, and the like.
  • mycosporine-like amino acid compound includes both the neutral, uncharged form of the compound/molecule and equally the salt form of the compound.
  • the salt form of the mycosporine-like amino acid compounds leads to a lower logPOW and, thus, making the compounds more hydrophilic, which results in a better water solubility.
  • the cationic salts of the mycosporine-like amino acid compounds support emulsification processes in emulsions, due to their surface active, i.e. co- emulsifying, properties.
  • the cationic salt form of the mycosporine-like 220084 compounds shows excellent substantivity behaviour on skin and hair: most conditioning actives are cationic; the conditioning effect leads to a softer skin feel, which makes the end products more accepted by the consumer.
  • the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention optionally contains at least one film forming agent (c).
  • a film forming agent (c) is not mandatory in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention but can be advantageously incorporated.
  • Film forming agents are well known in the art from their use as agents for improving the water resistance of sunscreen products.
  • a film forming agent is a hydrophobic material that imparts water resistance and film forming characteristics to the sunscreen products, cosmetic or pharmaceutical preparations or homecare products.
  • suitable film forming agents include copolymers derived from polymerization of octadecene-1 and maleic anhydride.
  • a preferred film forming agent is a polyanhydride resin.
  • Another preferred film forming agent is a copolymer of vinyl pyrrolidone and eicosene monomers.
  • Standard film forming agents are chitosan, microcrystalline chitosan, quaternized chitosan, polyvinyl pyrrolidone, vinyl pyrrolidone/vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid and salts thereof and similar compounds.
  • the film forming agents are preferably selected from the group consisting of Polyamide-8 (such as Oleocraft LP 20 PA (MV)), Polyamide-3 (such as Oleocraft MP 32 PA (MV)), Trimethylpentanediol/Adipic 220084 Acid/Glycerin Crosspolymer (such as WetFilm), Octyldodecyl Citrate Crosspolymer (such as CosmoSurf CE 100), Polyglyceryl-3 Methyl Glucose Distearate (such as TegoCare 450), C28-52 Olefin/Undecylenic Acid Copolymer (such as Performa V6112), Hydrolyzed Jojoba esters, Jojoba Esters, Aqua (such as Floraester Jojoba K100), Cyclopentasiloxane Acrylates/Dimethicone copolymer (such as KP545), Acrylates/Beheneth-25 Methacylate Copo
  • Polyamide-8 such as Ole
  • the film forming agents are selected from the group consisting of Trimethylpentanediol/Adipic Acid/Glycerin Crosspolymer (such as WetFilm), Octyldodecyl Citrate Crosspolymer (such as CosmoSurf CE 100), Polyglyceryl-3 Methyl Glucose Distearate (such as TegoCare 450), C28-52 Olefin/Undecylenic Acid Copolymer (such as Performa V6112), Hydrolyzed Jojoba esters, Jojoba Esters, Aqua (such as Floraester Jojoba K100), Cyclopentasiloxane Acrylates/Dimethicone copolymer (such as KP545), Styrene/Acrylates Copolymer (such as Dermacryl E Polymer), 220084 Acrylates/Octylacrylamide Copolymer (such as Dermacryl 2.0 Polymer), Beeswax (C
  • the film forming agents are selected from the group consisting of Hydrolyzed Jojoba esters, Jojoba Esters, Aqua (such as Floraester Jojoba K100), Cyclopentasiloxane Acrylates/Dimethicone copolymer (such as KP545), Styrene/Acrylates Copolymer (such as Dermacryl E Polymer), Acrylates/Octylacrylamide Copolymer (such as Dermacryl 2.0 Polymer), Beeswax (Cera Alba) (and) Sodium Stearoyl Lactylate (such as SymEffect Sun), Pullulan, Xanthan Gum, Microcrystalline cellulose (and) Sphingomonas ferment extract (and) Cellulose gum (such as PemuPurTM START Polymer), Microcrystalline Cellulose (and) Cellulose Gum (such as Natpure Cellgum Plus), Hydrogenated Polycyclopentadiene (and) Caprylic/Capric Trigly
  • the aforesaid film forming agents are used in the sunscreen, cosmetic or pharmaceutical preparation or homecare product either as a single component or preferably in a mixture with two or more further of said film forming agents as specified above.
  • the film forming agent (c) is used in amounts effective to allow the final formulation to remain on the skin after exposure to circulating water for at least 40 to 80 minutes.
  • a mycosporine-like amino acid compound (b) as defined herein to a sunscreen product or cosmetic or pharmaceutical preparation or homecare product according to the present invention, the adhesion of the film forming agent (c) on the skin or on surfaces can significantly be improved.
  • the combination of a mycosporine-like amino acid compound (b) and a film forming agent (c) result in a synergistic adherence effect of the sunscreen product or cosmetic or pharmaceutical preparation or homecare product on the skin or on a surface, to which the formulation is applied.
  • the improved adherence of the film forming agent in turn results in an improved water resistance, and, thus, provides excellent UV-protection even after bathing compared to products or preparations without the addition of the specified mycosporine- like amino acid compounds.
  • the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the first aspect of the present invention comprises thus one of the following combinations of components (b) and (c): ⁇ at least one compound according to formula (I) as defined herein plus at least one film forming agent: Hydrolyzed Jojoba esters and/or Jojoba Esters and/or Aqua 220084 (such as Floraester Jojoba K100) and/or Cyclopentasiloxane Acrylates/Dimethicone copolymer (such as KP545) and/or Styrene/Acrylates Copolymer (such as Dermacryl E Polymer) and/or Acrylates/Octylacrylamide Copolymer (such as Dermacryl 2.0 Polymer) and/or Beeswax (Cera Alba) (and) Sodium Stearoyl Lactylate (such as SymEffect Sun) and/or Pullulan and/or Xanthan Gum and/or Microcrystalline
  • More preferred combinations of component (b) and (c) in the sunscreen product or cosmetic or pharmaceutical preparation according to the first aspect of the present invention are: ⁇ MAA-1 plus at least one film forming agent: Hydrolyzed Jojoba esters and/or Jojoba Esters and/or Aqua (such as Floraester Jojoba K100) and/or Cyclopentasiloxane Acrylates/Dimethicone copolymer (such as KP545) and/or Styrene/Acrylates Copolymer (such as Dermacryl E Polymer) and/or Acrylates/Octylacrylamide Copolymer (such as Dermacryl 2.0 Polymer) and/or Beeswax (Cera Alba) (and) Sodium Stearoyl Lactylate (such as SymEffect Sun) and/or Pullulan and/or Xanthan Gum and/or Microcrystalline cellulose (and) Sphingomonas ferment extract (and) Cellulose gum (such as PemuPur
  • a synergistic water resistance improving effect can be shown for a combination of a mycosporine-like amino acid compound such as MAA-1, MAA-2, MAA-3, MAA-4, MAA-5, MAA-6, MAA-7, MAA-8, MAA-9, MAA-10 or MAA-11 and any of the film forming agent.
  • This tenacity effect can especially be observed when the mycosporine-like amino acid is in its salt form, i.e. in its cationic form.
  • a beneficial tenacity improving effect can preferably be obtained for MAA-2 and MAA-9.
  • the combination of the film building agents with said mycosporine-like amino acid compounds show a distinctive adhesion of the sunscreen products, cosmetic or pharmaceutical preparation or homecare product on the skin or on surfaces, resulting in an improvement of the water resistance.
  • the adhesion improving effect is especially pronounced for the mycosporine-like amino acid compounds MAA-2 salt and MAA-9 acid, when combined with any of the film forming agent.
  • ⁇ MAA-12 plus at least one film forming agent Hydrolyzed Jojoba esters and/or Jojoba Esters and/or Aqua (such as Floraester Jojoba K100) and/or Cyclopentasiloxane Acrylates/Dimethicone copolymer (such as KP545) and/or Styrene/Acrylates Copolymer (such as Dermacryl E Polymer) and/or Acrylates/Octylacrylamide Copolymer (such as Dermacryl 2.0 Polymer) and/or Beeswax (Cera Alba) (and) Sodium Stearoyl Lactylate (such as SymEffect Sun) and/or Pullulan and/or Xanthan Gum and/or Microcrystalline cellulose (and) Sphingomonas ferment extract (and) Cellulose gum (such as PemuP
  • the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the invention contains the primary sun protection factors, i.e. inorganic and/or organic UV-filters, in a total amount so that the product or preparation according to the invention has a sun protection factor SPF of 6 to 100, preferably 6 to 70.
  • Such compositions according to the invention are particularly suitable for protecting the skin, hair and nails.
  • secondary sun protection ingredients of the antioxidant type may also be advantageously used in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention in order to further optimize UV protection.
  • Secondary sun protection ingredients of the antioxidant type interrupt the photochemical reaction chain which is initiated when UV rays penetrate into the skin.
  • secondary sun protection ingredients are amino acids (for example arginine, lysine, glycine, histidine, tyrosine, tryptophane) and derivatives thereof, imidazoles (for example urocanic acid) and derivatives thereof, peptides, such as D,L- carnosine, D-carnosine, L-carnosine and derivatives thereof (for example anserine), carotenoids, carotenes (for example alpha-carotene, beta-carotene, lycopene) and 220084 derivatives thereof, chlorogenic acid and derivatives thereof, liponic acid and derivatives thereof (for example dihydroliponic acid), aurothioglucose, propylthiouracil and other thiols (for example thioredoxine, glutathione, cysteine, cystine, cystamine and glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, but
  • the group of secondary sun protection ingredients also encompasses plant- based extract(s).
  • Said plant-based extracts have antioxidative and in general photoprotective properties and interrupt the photochemical reaction chain which is initiated when UV rays penetrate into the skin, thus, are effective in preventing skin aging.
  • the plant extracts with UV protection properties are selected from the group 220084 consisting of Lignin/Cellulose, Lignin, Lignin Hydrolyzed, Propolis and green propolis, Galanga Extract, macro and micro algae (Porphyra, red algae (Porphyra Umbilicalis), Palmaria palmata, Saccharina latissimi, Corallina pilulifera, Eckloina cava, Sargassum sagamianum, Porphyra rosengurttii, Sargassum siliquastrum, Thalassiosira weissflogii, Green Microalgae (e.g.
  • the plant extracts with UV protection properties are selected from the group consisting of Lignin/Cellulose, Lignin, Lignin Hydrolyzed, Galanga Extract, Porphyra, red algae (Porphyra Umbilicalis), Green Microalgae (e.g.
  • the amount of secondary sun protection substances in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention is advantageously from 0.005 to 5.0 % by weight, preferably from 0.01 to 4.0 % by weight, most preferred from 0.05 to 3.0 % by weight, based on the total weight of the ready-to-use formulation.
  • the UV-filters are incorporated either in the aqueous or in the lipophilic part of the sunscreen product, cosmetic or pharmaceutical preparation or homecare product, depending if they are water or oil (fat) soluble/miscible UV-filters or may even be added to the final product by standard methods known to a person skilled in the art.
  • the at least one primary organic and/or inorganic UV-filter (a) according to the first aspect of the present invention is present in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product in an amount of 0.01 to 80.0 % by weight, based on the total weight of the final formulation.
  • the sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprises the primary organic and/or inorganic UV-filter (a) in an amount of 0.1 to 75.0 % by weight, based on the total weight of the final formulation.
  • the UV-filter is advantageously used in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product in an amount of 0.5 to 70.0 % by weight, based on the total weight of the final formulation.
  • the UV- filter is advantageously used in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product in an amount of 1.0 to 60.0 % by weight, based on the total weight of the final formulation.
  • the above amounts relate to the total content of the UV-filters in the mixture, i.e. the amount is the sum of the content of all primary UV-filters in the mixture.
  • the total amount of UV-filters are present in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention, in an amount of 0.1 to 85.0 % by weight, based on the total weight of the final formulation.
  • the sunscreen product, cosmetic or pharmaceutical preparation comprises the primary organic and/or inorganic UV-filter (a) and the further UV-protection components as defined herein in an amount of 0.3 to 80.0 % by weight, based on the total weight of the final formulation.
  • the UV-filter (a) and the further UV-protection components as defined herein are advantageously used in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product in an amount of 0.5 to 75.0 % by weight, based on the total weight of the final formulation.
  • the at least one mycosporine-like amino acid compound (b) according to the first aspect of the present invention is present in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product in an amount of 0.001 to 15.0 % by weight, based on the total weight of the final formulation.
  • the sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprises the at least one mycosporine-like amino acid compound (b) in an amount of 0.01 to 10.0 % by weight, based on the total weight of the final formulation.
  • the at least one mycosporine-like amino acid compound (b) is advantageously used in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product in an amount of at 0.05 to 7.5 % by weight, based on the total weight of the final formulation.
  • the at least one mycosporine-like amino acid compound is advantageously used in the sunscreen product, cosmetic or 220084 pharmaceutical preparation or homecare product in an amount of at 0.1 to 5.0 % by weight, based on the total weight of the final formulation.
  • the optionally at least one film forming agent (c) according to the first aspect of the present invention is present in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product in an amount of 0.01 to 10.0 % by weight, based on the total weight of the final formulation.
  • the sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprises the film forming agent (c) in an amount of 0.05 to 8.0 % by weight, based on the total weight of the final formulation.
  • the film forming agent (c) is advantageously used in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product in an amount of 0.1 to 5.0 % by weight, based on the total weight of the final formulation.
  • the above amounts relate to the total content of the film forming agents in the mixture, i.e. the amount is the sum of the content of all film forming agents in the mixture.
  • the sunscreen product according to the first aspect of the present invention comprises (i) 0.01 to 80.0 % by weight of primary organic and/or inorganic UV-filter; (ii) 0.001 to 15.0 % by weight of at least one mycosporine-like amino acid compound as defined herein; and (iii) optionally 0.01 to 10.0 % by weight of at least one film forming agent; based on the based on the total weight of the final formulation.
  • the cosmetic or pharmaceutical preparation according to the first aspect of the present invention comprises 220084 (iv) 1.0 to 60.0 % by weight of at least one primary organic and/or inorganic UV-filter; (v) 0.1 to 5.0 % by weight of at least one mycosporine-like amino acid compound as defined herein; and (vi) optionally 0.1 to 5.0 % by weight of at least one film forming agent; based on the based on the total weight of the final formulation.
  • the sunscreen products, cosmetic or pharmaceutical preparations or homecare products according to the present invention provide broad spectrum photo-protection und therefore provide protection from both UVA and UVB radiation.
  • Sun protection factor (SPF) is a measure of UVB protection.
  • the compositions of the present invention have an SPF of at least 6.
  • the SPF can vary as needed.
  • the type and amount of UVA and UVB filters can be varied to obtain a desired level of SPF.
  • the SPF of the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention is at least 6, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80 or even more.
  • the sunscreen product, cosmetic or pharmaceutical, in particular dermatological, preparation or homecare product as defined herein are intended for topical application, such as in the form of ointments, pastes, creams and gels, etc. they are preferably based on a carrier. Most common acceptable carrier is water.
  • Acceptable carries other than water include glycerin, C1-4 alcohols, organic solvents, fatty alcohols, fatty ethers, fatty esters, polyols, glycols, vegetable oils, mineral oils, liposomes, laminar lipid materials, water, or a mixture thereof.
  • Non-limiting examples of organic solvents include mono alcohols and polyols such as ethyl alcohol, isopropyl alcohol, propyl alcohol, benzyl alcohol, and phenylethyl alcohol, or glycols or glycol ethers such as, for example, monomethyl, monoethyl and monobutyl ethers of ethylene glycol, propylene glycol or ethers thereof such as, for example, monomethyl ether of propylene glycol, butylene glycol, hexylene glycol, dipropylene glycol as well as alkyl ethers of diethylene glycol, for example monoethyl ether or monobutyl ether of diethylene glycol.
  • mono alcohols and polyols such as ethyl alcohol, isopropyl alcohol, propyl alcohol, benzyl alcohol, and phenylethyl alcohol
  • glycols or glycol ethers such as, for example, monomethyl, monoethyl and monobutyl ether
  • organic solvents are ethylene glycol, propylene glycol, butylene glycol, hexylene glycol, propane diol, and glycerin.
  • the organic solvents can be volatile or non- 220084 volatile compounds.
  • the total amount of carrier in the compositions can vary but is typically 40 to 90 % by weight, based on the total weight of the composition.
  • the products or preparations of the present invention may include at least one water-soluble or organic solvent.
  • Non-limiting examples of organic solvents include monoalcohols and polyols such as ethyl alcohol, isopropyl alcohol, propyl alcohol, benzyl alcohol, and phenylethyl alcohol, or glycols or glycol ethers such as, for example, monomethyl, monoethyl and monobutyl ethers of ethylene glycol, propylene glycol or ethers thereof such as, for example, monomethyl ether of propylene glycol, butylene glycol, hexylene glycol, dipropylene glycol as well as alkyl ethers of diethylene glycol, for example monoethyl ether or monobutyl ether of diethylene glycol.
  • monoalcohols and polyols such as ethyl alcohol, isopropyl alcohol, propyl alcohol, benzyl alcohol, and phenylethyl alcohol
  • glycols or glycol ethers such as, for example, monomethyl, monoethyl and monobut
  • organic solvents are ethylene glycol, propylene glycol, butylene glycol, hexylene glycol, propane diol, and glycerin.
  • the organic solvents can be volatile or non- volatile compounds.
  • water-soluble solvents include alkanols (polyhydric alcohols such as glycols and polyols) such as glycerin, 1 ,2,6-hexanetriol, trimethylolpropane, ethylene glycol, propylene glycol, diethylene glycol, butylene glycol, hexylene glycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol, dipropylene glycol, 1 ,3-butanediol, 2,3-butanediol, 1 ,4-butanediol, 3-methyl-1 ,3- butanediol, 1 ,5- pentanediol, tetraethylene glycol
  • the total amount water-soluble or organic solvent(s) in the composition according to the present invention may vary but is typically 0.1 to 50 % by weight, based on the total weight of the composition.
  • the products or preparations of the present invention may include at least one solubilizing agent.
  • Solubilizing agents are compounds that help solubilize the UV-filter(s) and/or other components in the compositions.
  • a particularly useful but non limiting example of a solubilizing agent is a hydrotrope.
  • Hydrotropes (or hydrotropic agents) are a diverse class of typically water-soluble compounds that may be characterized by an amphiphilic molecular structure and an ability to dramatically increase the solubility of poorly soluble organic molecules in water.
  • Non-limiting examples of hydrotopes include sodium 1,3-benzenedisulfonate, sodium benzoate, sodium 4-pyridinecarboxylate, sodium salicylate, sodium benzene sulfonate, caffeine, sodium p-toluene sulfonate, sodium butyl monoglycolsulfate, 4- aminobenzoic acid HCI, sodium cumene sulfonate, N,N-diethylnicotinamide, N-picolylnicotinamide, N-allylnicotinamide, 2- methacryloyloxyethyl phosphorylcholine, resorcinol, butylurea, pyrogallol, N- picolylacetamide 3.5, procaine HCI, proline HCI, nicotinamide, pyridine, 3-picolylamine, sodium ibuprofen, sodium xylenesulfonate, ethyl carbamate, pyridoxal hydrochlor
  • particularly useful hydrotropes include nicotinamide (niacinamide), caffeine, sodium PCA, sodium salicylate, urea, and dhydroxyethyl urea, in particular, nicotinamide (niacinamide) and/or caffeine.
  • nicotinamide niacinamide
  • a combination of two or more, three or more, or four or more hydrotopes may also be used in the compositions according to the present invention.
  • the total amount of solubilizing agent(s) in the compositions of the present invention may vary but are typically in an amount of 0.01 to 20 % by weight, based on the total weight of the composition.
  • the sunscreen product, cosmetic or pharmaceutical preparation or homecare product may include at least one oil phase or at least one oil component, waxes, starch, tragacanth, cellulose derivatives, polyethylene glycols, silicones, bentonites, silica, talc and zinc oxide or any mixture thereof.
  • Powders include carriers such as lactose, talc, silica, aluminium hydroxide, calcium silicate and polyamide powder or any mixture thereof.
  • Solutions and emulsions include carriers such as solvents such as water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, propylene glycol, etc. or any mixture thereof.
  • the oil phase or the oil component in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention which may be suitable are for example plant oils, hydrocarbons, fatty alcohols, fatty acid esters, or mixtures of two or more of the aforesaid oil components.
  • the oil phase or oil component in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product is preferably a plant oil and even more preferably a liquid plant oil. It can also advantageously be a mixture of two or more plant oils components, especially liquid plant oil mixtures.
  • Plant oils or vegetable oils are oils extracted from seeds, or less often, from other parts of fruits. Like animal fats, plant oils are mixtures of triglycerides. Soybean oil, rapeseed oil and cocoa butter are examples of plant oils from seeds. Olive oil, palm oil and rice bran oil are examples of oils from other parts of fruits. In common usage, plant oil or vegetable oil may refer exclusively to vegetable fats which are liquid at room temperature or at 35 to 37 °C skin temperature. Vegetable oils are usually edible. [0271] The term “plant oils” also includes unsaturated plant oils. Unsaturated oils or vegetable oils can be transformed through partial or complete “hydrogenation” into oils of higher melting point.
  • the hydrogenation process involves “sparging” the oil at high temperature and pressure with hydrogen in the presence of a catalyst, typically a powdered nickel compound. As each carbon-carbon double-bond is chemically reduced 220084 to a single bond, two hydrogen atoms each form single bonds with the two carbon atoms. The elimination of double bonds by adding hydrogen atoms is called saturation; as the degree of saturation increases, the oil progresses toward being fully hydrogenated.
  • An oil may be hydrogenated to increase resistance to rancidity (oxidation) or to change its physical characteristics. As the degree of saturation increases, the oil's viscosity and melting point increase.
  • the plant oil is selected from the group consisting of Persea Gratissima (Avocado Oil), Abies Alba Seed Oil, Acacia Victoriae Seed Oil, Actinidia Chinensis (Kiwi) Seed Oil, Amaranthus Hypochondriacus Seed Oil, Arachis Hypogaea (Peanut) Oil, Astrocaryum Murumuru Seed Butter, Astrocaryum Tucuma Seed Butter, Astrocaryum Tucuma Seed Oil, Astrocaryum Vulgare Fruit Oil, Astrocaryum Vulgare Kernel Oil, Avena Sativa (Oat) Kernel Oil, Brassica Alba Seed Oil, Brassica Campestris (Rapeseed) Seed Oil, Butyrospermum Parkii (Shea) Butter, Butyrospermum Parkii (Shea) Oil, Calendula Officinalis Seed Oil, Calophyllum Inophyllum Seed Oil, Calophyllum Tacamahaca
  • Hydrocarbons are in general organic compounds consisting entirely of hydrogen and carbon. As defined by IUPAC nomenclature or organic chemistry, the classifications for hydrocarbons are: 1. Saturated hydrocarbons are the simplest of the hydrocarbon species. They are composed entirely of single bonds and are saturated with hydrogen. The formula for acyclic saturated hydrocarbons (i.e., alkanes) is CnH2n+2. The most general form of saturated hydrocarbons is CnH2n+2(1-r), where r is the number of rings. Those with exactly one ring are the cycloalkanes.
  • Saturated hydrocarbons are the basis of petroleum fuels and are found as either linear or branched species.
  • Unsaturated hydrocarbons have one or more double or triple bonds between carbon atoms. Those with double bond are called alkenes. Those with one double bond have the formula CnH2n (assuming non-cyclic structures). Those containing triple bonds are called alkynes. Those with one triple bond have the formula CnH2n ⁇ 2.
  • Aromatic hydrocarbons, also known as arenes are hydrocarbons that have at least one aromatic ring. 220084 [0275] Hydrocarbons can be inter alia liquids (e.g. hexane and benzene), waxes or low melting solids (e.g. paraffin wax and naphthalene).
  • 'aliphatic' refers to non- aromatic hydrocarbons. Saturated aliphatic hydrocarbons are sometimes referred to as “paraffins”. Mineral oils and waxes are mixtures of predominantly saturated hydrocarbons consisting of straight ⁇ chain, branched and ring structures with carbon chain lengths greater than C14. Mineral oils and waxes are chemical substances prepared from naturally occurring crude petroleum oil. They mainly consist of mineral oil saturated hydrocarbons (MOSH) and mineral oil aromatic hydrocarbons (MOAH). Hydrocarbons have been used for many decades in skin and lip care cosmetic products due to their excellent skin tolerance as well as their high protecting and cleansing performance and broad viscosity options. In contrast to vegetable oils, mineral oils are non ⁇ allergenic since they are highly stable and not susceptible to oxidation or rancidity.
  • a fatty alcohol (or long-chain alcohol) is usually a high-molecular-weight, straight- chain primary alcohol, but can also range from as few as 4 to 6 carbons to as many as 22 to 26, derived from natural fats and oils. The precise chain length varies with the source.
  • Some commercially important fatty alcohols are lauryl, stearyl and oleyl alcohols. They are colourless oily liquids (for smaller carbon numbers) or waxy solids, although impure samples may appear yellow.
  • Fatty alcohols usually have an even number of carbon atoms and a single alcohol group (—OH) attached to the terminal carbon. Some are unsaturated and some are branched.
  • fatty alcohols in nature are found as waxes which are esters with fatty acids and fatty alcohols.
  • the traditional sources of fatty alcohols have largely been various vegetable oils and these remain a large-scale feedstock.
  • the alcohols are obtained from the triglycerides (fatty acid triesters), which form the bulk of the oil.
  • the process involves the transesterification of the triglycerides to give methyl esters which are then hydrogenated to give the fatty alcohols.
  • Fatty alcohols are also prepared from petrochemical sources. In the Ziegler process, ethylene is oligomerized using triethylaluminium followed by air oxidation.
  • ethylene can be oligomerized to give mixtures of alkenes, which are subjected to hydroformylation, this process affording odd-numbered aldehyde, which is subsequently hydrogenated.
  • Fatty alcohols are mainly used in the production of detergents and surfactants. They are 220084 components also of cosmetic solvents. They find use as co-emulsifiers, emollients and thickeners in cosmetics.
  • the fatty alcohol is selected from the group consisting of phenyl propanol, dimethyl phenylbutanol, hexyldecanol, octyldodecanol, octyldecanol, tridecylalcohol, isostearyl alcohol, phenylisohexanol, phenylpropanol, trimethylbenzenepropanol, isoamylalcohol, isostearyl alcohol, and isotridecyl alcohol.
  • the fatty alcohol is selected from the group consisting of hexyldecanol, octyldodecanol, phenylpropanol, isoamylalcohol, and mixtures of two or more of the aforesaid fatty alcohols.
  • the fatty alcohol can be used either as a single component or in a mixture with one or more further different fatty alcohol(s) as specified above.
  • a fatty acid ester is a type of ester that results from the combination of a fatty acid with an alcohol.
  • the alcohol component is glycerol
  • the fatty acid esters produced can be monoglycerides, diglycerides or triglycerides.
  • Fatty acid esters have a conditioning effect of softening the skin to create a smoothing sensation. They are also added to cosmetics to dissolve high-polarity active ingredients and UV absorbers. Esters of straight-chain fatty acids and lower alcohols are effective for dissolving slightly soluble ingredients for oils with a light touch during application. Isostearic acids and other liquid oils with branched fatty acids and unsaturated fatty acids are commonly used as emollients. Higher fatty acid esters and esters of higher alcohols with relatively high melting points are added to skin creams to adjust the application touch. [0279] In addition to the oil phase or oil component as defined above, the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention preferably includes one or more oil bodies.
  • Suitable oil bodies which form constituents of the O/W emulsions, are, for example, Guerbet alcohols based on fatty alcohols having 6 to 18, preferably 8 to 10, carbon atoms, esters of linear C5 – C22 fatty acids with linear or branched C5 - C22 fatty alcohols or esters of branched C1 – C13 carboxylic acids with linear or branched C6 – C22 fatty alcohols, such as, for example, myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl 220084 oleate, myristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetyl behenate, cetyl erucate, stearyl myristate, ste
  • esters of linear C6 – C22 fatty acids with branched alcohols in particular 2- ethylhexanol, esters of C18 – C38 alkylhydroxy carboxylic acids with linear or branched C6 – C22 fatty alcohols, in particular Dioctyl Malate, esters of linear and/or branched fatty acids with polyhydric alcohols (such as, for example, propylene glycol, dimerdiol or trimertriol) and/or Guerbet alcohols, triglycerides based on C6 – C10 fatty acids, liquid mono-/di-/triglyceride mixtures based on C6 – C18 fatty acids, esters of C6 – C22 fatty alcohols and/or Guerbet alcohols with aromatic carboxylic acids, in particular benzoic acid, esters of C2 – C12 dicarboxylic acids with linear or branched alcohols having 1 to 22 carbon atoms or polyols
  • Finsolv® TN linear or branched, symmetrical or asymmetrical dialkyl ethers having 6 to 22 carbon atoms per alkyl group, such as, for example, dicaprylyl ether (Cetiol® OE), ring-opening products of epoxidized fatty acid esters with polyols, silicone oils (cyclomethicones, silicone methicone grades, etc.) and/or aliphatic or naphthenic hydrocarbons, such as, for example, squalane, squalene or dialkylcyclohexanes.
  • dicaprylyl ether such as, for example, dicaprylyl ether (Cetiol® OE), ring-opening products of epoxidized fatty acid esters with polyols, silicone oils (cyclomethicones, silicone methicone grades, etc.) and/or aliphatic or naphthenic hydrocarbons, such as, for example, squalane, squalen
  • the sunscreen product, cosmetic or pharmaceutical, in particular dermatological, preparation or homecare product according to the present invention may advantageously combined with further standard cosmetic or pharmaceutical excipients and/or active substances and/or additives and/or auxiliaries, such as are customarily used in such 220084 compositions, such as for example abrasives, anti-acne agents, agents against ageing of the skin, anti-cellulitis agents, anti-dandruff agents, anti-inflammatory agents, anti- microbial agents, irritation-preventing agents, irritation-inhibiting agents, antioxidants, astringents, odor absorbers, perspiration-inhibiting agents, antiseptic agents, anti-statics, binders, buffers, carrier materials, chelating agents, cell stimulants, cleansing agents, depilatory agents, surface-active substances, deodorizing agents, antiperspirants, softeners, emulsifiers, enzymes, enzyme inhibitors, essential oils, fibers, film-forming agents, fixatives, foam-forming agents, foam stabilizer
  • cosmetically or pharmaceutically excipients and/or active substances and/or additives and/or auxiliaries such as emollients, rheology additives, silicones, dry-feel modifiers, skin moisturizing and/or moisture-retaining substances, 220084 lenitive substances, physiological cooling agents, antioxidants, emulsifiers, anti-microbial agents, preservatives, fragrances or perfume oils, and any mixture of two or more of the afore-mentioned substances are particularly preferred in the preparation of sunscreen products, cosmetic and pharmaceutical preparations or homecare products.
  • emollients such as emollients, rheology additives, silicones, dry-feel modifiers, skin moisturizing and/or moisture-retaining substances, 220084 lenitive substances, physiological cooling agents, antioxidants, emulsifiers, anti-microbial agents, preservatives, fragrances or perfume oils, and any mixture of two or more of the afore-mentioned substances are particularly preferred in the preparation of sunscreen products, cosmetic
  • Oil bodies and emollients The sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention advantageously includes one or more oil bodies or emollients.
  • An emollient is an oleaginous or oily substance which helps to smooth and soften the skin, and may also reduce its roughness, cracking or irritation.
  • sunscreen products emollients counteract the known stickiness of some UV-filters and keep the crystalline and oil-soluble organic and inorganic UV-filters solubilized and prevent them from recrystallisation.
  • emollients serve as wetting agents for inorganic UV-filters for a homogeneous dispersion in the formulations.
  • Suitable oil bodies are, for example, Guerbet alcohols based on fatty alcohols having 6 to 18, preferably 8 to 10, carbon atoms, esters of linear C6-C22-fatty acids with linear or branched C6-C22-fatty alcohols or esters of branched C6-C 13- carboxylic acids with linear or branched C6-C 22-fatty alcohols, such as, for example, myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl oleate, myristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetyl behenate, cetyl erucate, stearyl myristate, stearyl palmitate, stearyl stearate, stearyl isostear
  • esters of linear C6-C22-fatty acids with branched alcohols in particular 2- ethylhexanol, esters of C18-C38- alkylhydroxy carboxylic acids with linear or branched C6- C 22-fatty alcohols, in particular Dioctyl Malate, esters of linear and/or branched fatty acids with polyhydric alcohols (such as, for example, propylene glycol, dimerdiol or trimertriol) and/or Guerbet alcohols, triglycerides based on C6 -C10-fatty acids, liquid mono-/di- 220084 /triglyceride mixtures based on C6-C18-fatty acids, esters of C6- C22-fatty alcohols and/or Guerbet alcohols with aromatic carboxylic acids, in particular benzoic acid, esters of C2- C12-dicarboxylic acids with linear or branched alcohols having 1 to 22 carbon atoms or polyols having
  • Finsolv® TN linear or branched, symmetrical or a symmetrical dialkyl ethers having 6 to 22 carbon atoms per alkyl group, such as, for example, dicaprylyl ether (Cetiol® OE), ring-opening products of epoxidized fatty acid esters with polyols, silicone oils (cyclomethicones, silicone methicone grades, etc.) and/or aliphatic or naphthenic hydrocarbons, such as, for example, squalane, squalene or dialkylcyclohexanes and any mixture thereof.
  • dicaprylyl ether such as, for example, dicaprylyl ether (Cetiol® OE), ring-opening products of epoxidized fatty acid esters with polyols, silicone oils (cyclomethicones, silicone methicone grades, etc.) and/or aliphatic or naphthenic hydrocarbons, such as, for example, squalane
  • Rheology modifiers The sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention advantageously includes one or more thickening agents and/or rheology modifier.
  • the rheology modifier is present in an amount that prevents significant dripping or pooling of the composition after application to the skin.
  • the rheology modifier is a carbomer.
  • the rheology modifier is selected from stearic acid, palmitic acid, stearyl alcohol, cetyl alcohol, behenyl alcohol, stearic acid, palmitic acid, the polyethylene glycol ether of stearyl alcohol having an average of about 1 to about 21 ethylene oxide units, the polyethylene glycol ether of cetyl alcohol having an average of about 1 to about 5 ethylene oxide units, and mixtures thereof.
  • Additional example of rheology modifiers include thickener or gelling agents, including substances which can increase the viscosity of a composition. Thickening agents include those that can increase the viscosity of a composition without substantially modifying the efficacy of the active ingredient within the formulation.
  • Thickening agents can also increase the stability of the formulations of the present application.
  • thickening agents include hydrogenated polyisobutene or trihydroxy stearin, or a mixture of both.
  • Additional non-limiting examples of additional 220084 thickening agents that can be used in the context of the present application include carboxylic acid polymers, crosslinked polyacrylate polymers, polyacrylamide polymers, polysaccharides, and gums.
  • carboxylic acid polymers include crosslinked compounds containing one or more monomers derived from acrylic acid, substituted acrylic acids, and salts and esters of these acrylic acids and the substituted acrylic acids, wherein the crosslinking agent contains two or more carbon-carbon double bonds and is derived from a polyhydric alcohol (see CTFA International Cosmetic Ingredient Dictionary, Fourth Edition, 1991, pp. 12 and 80).
  • Examples of commercially available carboxylic acid polymers include carbomers, which are homopolymers of acrylic acid crosslinked with allyl ethers of sucrose or pentaerythritol (e.g., CarbopolTM 900 series from B. F. Goodrich).
  • Non-limiting examples of crosslinked polyacrylate polymers include cationic and nonionic polymers.
  • Non-limiting examples of polyacrylamide polymers include polyacrylamide, isoparaffin and Laureth-7, multi-block copolymers of acrylamides and substituted acrylamides with acrylic acids and substituted acrylic acids.
  • Non-limiting examples of polysaccharides include cellulose, carboxymethyl hydroxyethylcellulose, cellulose acetate propionate carboxylate, hydroxyethylcellulose, hydroxyethyl ethylcellulose, hydroxypropyl cellulose, hydroxypropyl methylcellulose, methyl hydroxyethylcellulose, microcrystalline cellulose, sodium cellulose sulfate, and mixtures thereof.
  • alkyl substituted cellulose where the hydroxy groups of the cellulose polymer are hydroxyalkylated (preferably hydroxy ethylated or hydroxypropylated) to form a hydroxyalkylated cellulose which is then further modified with a C10-C30 straight chain or branched chain alkyl group through an ether linkage.
  • these polymers are ethers of C10-C30 straight or branched chain alcohols with hydroxyalkylcelluloses.
  • Other useful polysaccharides include scleroglucans comprising a linear chain of (1-3) linked glucose units with a (1-6) linked glucose every three unit.
  • Non-limiting examples of gums that can be used with the present compositions include acacia, agar, algin, alginic acid, ammonium alginate, amylopectin, calcium 220084 alginate, calcium carrageenan, carnitine, carrageenan, dextrin, gelatin, gellan gum, guar gum, guar hydroxypropyltrimonium chloride, hectorite, hyaluroinic acid, hydrated silica, hydroxypropyl chitosan, hydroxypropyl guar, karaya gum, kelp, locust bean gum, natto gum, potassium alginate, potassium carrageenan, propylene glycol alginate, sclerotium gum, sodium carboxymethyl dextran, sodium carrageenan, tragacanth gum, xanthan gum, and mixtures thereof.
  • the thickening agent is Chondrus crispus (carrageenan) extract.
  • the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention may advantageously include one or more agents for improving water resistance.
  • An agent for improving water resistance is a hydrophobic material that imparts film forming and water resistance characteristics to an emulsion.
  • Typical suitable water resistance improving agents include copolymers derived from polymerization of octadecene-1 and maleic anhydride.
  • a preferred water resistance improving agent is a polyanhydride resin.
  • Another preferred water resistance improving agent is a copolymer of vinyl pyrrolidone and eicosene monomers.
  • the water resistance improving agent(s) is/are used in amounts effective to allow the final formulation to remain on the skin or surface after exposure to circulating water for at least 40 minutes, preferably 80 minutes.
  • One or more water resistance improving agents can optionally be included in the final formulation in an amount ranging from 0.01 to 10.0 % by weight, preferably 0.05 to 8.0 % by weight, more preferably 0.1 to 5.0 % by weight, based on the total weight of the final formulation.
  • Silicones In order to impart a silky, spreadable, and luxurious texture and to make skin look and feel smoother, and additionally to improve processability (antifoaming) the sunscreen product or cosmetic or pharmaceutical preparation according to the present invention preferably includes one or more silicones or silicone deratives.
  • Suitable silicones can be chosen from the group consisting of Acefylline Methylsilanol Mannuronate, Acetylmethionyl Methylsilanol Elastinate Acrylates/Behenyl, Acrylate/Dimethicone Methacrylate Copolymer, Acrylates/Behenyl Methacrylate/Dimethicone Methacrylate Copolymer, Acrylates/Bis-Hydroxypropyl Dimethicone Crosspolymer, Acrylates/Dimethicone Copolymer, Acrylates/Dimethicone 220084 Methacrylate/Ethylhexyl Acrylate Copolymer, Acrylates/Dimethiconol Acrylate Copolymer, Acrylates/Ethylhexyl Acrylate/Dimethicone Methacrylate Copolymer, Acrylates/Octylacrylamide/Diphenyl Amodimethicone Copolymer
  • the silicones to be contained in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the invention are Dimethicone, Cyclomethicone, Cyclopentasiloxane, Cyclotetrasiloxane, Phenyl Trimethicone, and Cyclohexasiloxane.
  • the total amount of silicone compound(s) in the compositions according to the present invention can vary but is typically 0.1 to 20 % by weight, based on the total weight of the composition.
  • Dry-feel modifiers The sunscreen product or cosmetic or pharmaceutical preparation according to the present invention is preferably combined with dry-feel modifiers.
  • a dry-feel modifier is an agent which, when incorporated in an emulsion, imparts a "dry feel" to the skin when the emulsion dries. Dry-feel modifiers may also reduce sunscreen migration on the skin. Dry feel modifiers can include starches, talc, kaolin, chalk, zinc oxide, silicone fluids, inorganic salts such as barium sulfate and sodium chloride, C6 to C12 alcohols such as octanol; sulfonated oils; surface treated silica, precipitated silica, fumed silica such as Aerosil® available from the Degussa Inc. of New York, N.Y. U.S.A.
  • the sunscreen product or cosmetic or pharmaceutical preparation according to the present invention comprises advantageously one or more skin-moisturizing and/or moisture-retaining substances.
  • Preferred skin moisturizing and/or moisture-retaining substances are selected from the group consisting of alkane diols or alkane triols comprising 3 to 12 carbon atoms, preferably C3-C10-alkane diols and C3-C10-alkane triols. More preferably the skin moisturizing agents are selected from the group consisting of glycerol, 1,2- propylene glycol, 1,2-butylene glycol, 1,3-butylene glycol, 1,2-pentanediol, 1,2- hexanediol, 1,2-octanediol and 1,2-decanediol.
  • Further skin moisturizing and/or moisture- retaining substances include sodium lactate, urea, urea derivatives, alcohols, glycerol, diols such as propylene glycol, hexylene glycol, collagen, elastin or hyaluronic acid, diacyl adipates, petrolatum, urocanic acid, lecithin, panthenol, phytantriol, lycopene, (pseudo- )ceramides, glycosphingolipids, cholesterol, phytosterols, chitosan, chondroitin sulphate, lanolin, lanolin esters, amino acids, alpha-hydroxy acids (such as citric acid, lactic acid, malic acid) and their derivatives, mono-, di- and oligosaccharides such as glucose, galactose, fructose, mannose, fructose and lactose, polysugars such as R-glucans, in particular 1,3-1,
  • the sunscreen product or cosmetic or pharmaceutical preparation according to the present invention can also contain advantageously one or more lenitive substances, wherein any lenitive substances can be used which are suitable or customary in cosmetic or pharmaceutical applications such as alpha-bisabolol, azulene, guaiazulene, 18-beta-glycyrrhetinic acid, allantoin, Aloe vera juice or gel, extracts of Hamamelis virginiana (witch hazel), Echinacea species, Centella asiatica, chamomile, Arnica montana, Glycyrrhiza species, algae, seaweed and Calendula officinalis, and vegetable oils such as sweet almond oil, baobab oil, olive oil and panthenol, Laureth-9, Trideceth-9 and 4-t-butylcyclohexanol.
  • any lenitive substances can be used which are suitable or customary in cosmetic or pharmaceutical applications such as alpha-bisabolol, azulene, guai
  • Physiological cooling agents The sunscreen product or cosmetic or pharmaceutical preparation according to the present invention can be particularly advantageously combined with one or more physiological cooling agent(s).
  • the use of cooling agents can alleviate itching.
  • Preferred individual cooling agents for use within the framework of the present invention are listed below.
  • cooling agents listed can also be used in combination with one another: which are preferably selected here from the following list: menthol and menthol derivatives (for example L-menthol, D-menthol, racemic menthol, isomenthol, neoisomenthol, neomenthol) menthylethers (for example (I-menthoxy)-1,2- propanediol, (l-menthoxy)-2-methyl-1,2-propanediol, l-menthyl-methylether), menthone glyceryl acetal, menthone glyceryl ketal or mixtures of both, menthylesters (for example menthylformiate, menthylacetate, menthylisobutyrate, menthyhydroxyisobutyrat, menthyllactates, L-menthyl-L-lactate, L-menthyl-D-lactate, menthyl-(
  • Cooling agents which are preferred due to their particular synergistic effect are l-menthol, d-menthol, racemic menthol, menthone glycerol acetal (trade name: Frescolat ® MGA), menthyl lactate (preferably l-menthyl lactate, in particular l-menthyl l-lactate (trade name: Frescolat ® ML)), substituted menthyl-3-carboxamides (such as menthyl-3-carboxylic acid N-ethyl amide), 2-isopropyl-N-2,3-trimethyl butanamide, substituted cyclohexane carboxamides, 3-menthoxypropane-1,2-diol, 2-hydroxyethyl menthyl carbonate, 2- hydroxypropyl menthyl carbonate and isopulegol.
  • menthone glycerol acetal trade name: Frescolat ® MGA
  • menthyl lactate preferably l
  • cooling agents 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: Frescolat ® ML)), 3-menthoxypropane-1,2-diol, 2-hydroxyethyl menthyl carbonate and 2- hydroxypropyl menthyl carbonate.
  • menthone glycerol acetal trade name: Frescolat ® MGA
  • menthyl lactate preferably l-menthyl lactate, in particular l-menthyl l-lactate (trade name: Frescolat ® ML)
  • 3-menthoxypropane-1,2-diol 2-hydroxyethyl menthyl carbonate and 2- hydroxypropyl menthyl carbonate.
  • Very particularly preferred cooling agents are l- menthol, menthone glycerol acetal (trade name: Frescolat ® MGA) and menthyl lactate (preferably l-menthyl lactate, in particular l-menthyl l-lactate (trade name: Frescolat ® ML).
  • Antioxidants The sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention comprises advantageously one or more antioxidants.
  • Suitable antioxidants encompass amino acids (preferably glycine, histidine, tyrosine, tryptophan) and derivatives thereof, imidazoles (preferably urocanic acid) and derivatives thereof, peptides, preferably D,L-carnosine, D-carnosine, L- carnosine and derivatives thereof (preferably anserine), carnitine, creatine, matrikine peptides (preferably lysyl-threonyl-threonyl-lysyl-serine) and palmitoylated pentapeptides, carotenoids, carotenes (preferably alpha-carotene, beta-carotene, lycopene) and derivatives thereof, lipoic acid and derivatives thereof (preferably dihydrolipoic acid), aurothioglucose, propyl thiouracil and other thiols (preferably thioredoxine, glutathione, cysteine, cystine, cystamine and glycosyl
  • chelators preferably alpha-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin, alpha-hydroxy acids (preferably citric acid, lactic acid, malic acid), humic acid, bile acid, bile extracts, tannins, bilirubin, biliverdin, EDTA, EGTA and derivatives thereof), unsaturated fatty acids and derivatives thereof (preferably gamma-linolenic acid, linoleic acid, oleic acid), folic acid and derivatives thereof, ubiquinone and derivatives thereof, ubiquinol and derivatives thereof, vitamin C and derivatives (preferably ascorbyl palmitate, Mg ascorbyl phosphate, ascorbyl acetate, ascorbyl glucoside), tocopherols and derivatives (preferably vitamin E acetate), vitamin A and derivatives (vitamin A palmitate) and coniferyl benzoate of benzo
  • the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention can also advantageously contain one or more emulsifiers in order to keep the sunscreen product, 220084 cosmetic or pharmaceutical preparation or homecare product stable.
  • Emulsifiers include amphoteric, anionic, cationic or nonionic emulsifiers, used alone or as a mixture.
  • the emulsifiers are chosen in an appropriate manner according to the emulsion to be obtained.
  • Preferred examples include: - products of the addition of 2 to 30 mol ethylene oxide and/or 0 to 5 mol propylene oxide onto linear C8-22 fatty alcohols, onto C12-22 fatty acids and onto alkyl phenols containing 8 to 15 carbon atoms in the alkyl group; - C12/18 fatty acid monoesters and diesters of addition products of 1 to 30 mol ethylene oxide onto glycerol; - glycerol mono- and diesters and sorbitan mono- and diesters of saturated and unsaturated fatty acids containing 6 to 22 carbon atoms and ethylene oxide addition products thereof; - addition products of 15 to 60 mol ethylene oxide onto castor oil and/or hydrogenated castor oil; - polyol est
  • Mixtures of compounds from several of these classes are also suitable; - addition products of 2 to 15 mol ethylene oxide onto castor oil and/or hydrogenated castor oil; - partial esters based on linear, branched, unsaturated or saturated C6/22 fatty acids, ricinoleic acid and 12-hydroxystearic acid and glycerol, polyglycerol, pentaerythritol, dipentaerythritol, sugar alcohols (for example sorbitol), alkyl glucosides (for example methyl glucoside, butyl glucoside, lauryl glucoside) and polyglucosides (for example cellulose); - mono-, di and trialkyl phosphates and mono-, di- and/or tri-PEG-alkyl phosphates and salts thereof; - wool wax alcohols; - polysiloxane/polyalkyl polyether copolymers and corresponding derivatives; - mixed esters of pentaery
  • the addition products of ethylene oxide and/or propylene oxide onto fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters and sorbitan mono- and diesters of fatty acids or onto castor oil are known commercially available products. They are homologue mixtures of which the average degree of alkoxylation corresponds to the ratio between the quantities of ethylene oxide and/or propylene oxide and substrate with which the addition reaction is carried out. C12/18 fatty acid monoesters and diesters of addition products of ethylene oxide onto glycerol are known as lipid layer enhancers for cosmetic formulations.
  • Partial glycerides Typical examples of suitable partial glycerides are hydroxystearic acid monoglyceride, hydroxystearic acid diglyceride, isostearic acid monoglyceride, isostearic acid diglyceride, oleic acid monoglyceride, oleic acid diglyceride, ricinoleic acid monoglyceride, ricinoleic acid diglyceride, linoleic acid monoglyceride, linoleic acid diglyceride, linolenic acid monoglyceride, linolenic acid diglyceride, erucic acid monoglyceride, erucic acid diglyceride, tartaric acid monoglyceride, tartaric acid diglyceride, citric acid monoglyceride, citric acid diglyceride, malic acid monoglyceride, malic acid diglyceride, malic acid monoglyceride, malic acid diglyceride, malic
  • Sorbitan esters are sorbitan monoisostearate, sorbitan sesquiisostearate, sorbitan diisostearate, sorbitan triisostearate, sorbitan monooleate, sorbitan sesquioleate, sorbitan dioleate, sorbitan trioleate, sorbitan monoerucate, sorbitan sesquierucate, sorbitan dierucate, sorbitan trierucate, sorbitan monoricinoleate, sorbitan sesquiricinoleate, sorbitan diricinoleate, sorbitan triricinoleate, sorbitan monohydroxystearate, sorbitan sesquihydroxystearate, sorbitan dihydroxystearate, sorbitan trihydroxystearate, sorbitan monotart
  • Polyglycerol esters Typical examples of suitable polyglycerol esters are Polyglyceryl-2 Dipolyhydroxystearate (Dehymuls ® PGPH), Polyglycerin-3-Diisostearate (Lameform ® TGI), Polyglyceryl-4 Isostearate (Isolan ® GI 34), Polyglyceryl-3 Oleate, Diisostearoyl Polyglyceryl-3 Diisostearate (Isolan® PDI), Polyglyceryl-3 Methylglucose Distearate (Tego Care ® 450), Polyglyceryl-3 Beeswax (Cera Bellina ® ), Polyglyceryl-4 Caprate (Polyglycerol Caprate T2010/90), Polyglyceryl-3 Cetyl Ether (Chimexane ® NL), Polyglyceryl-2 Dipolyhydroxystearate (Dehymuls ® PGPH), Polyglycerin-3-Diisostear
  • Suitable polyolesters are the mono-, di- and triesters of trimethylol propane or pentaerythritol with lauric acid, cocofatty acid, tallow fatty acid, palmitic acid, stearic acid, oleic acid, behenic acid and the like optionally reacted with 1 to 30 mol ethylene oxide.
  • Anionic emulsifiers Typical anionic emulsifiers are aliphatic C12 to C 22 fatty acids, such as palmitic acid, stearic acid or behenic acid for example, and C12 to C22 dicarboxylic acids, such as azelaic acid or sebacic acid for example.
  • Amphoteric emulsifiers are amphoteric or zwitterionic surfactants.
  • Zwitterionic surfactants are surface-active compounds which contain at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines, such as the N-alkyl-N,N-dimethyl ammonium glycinates, for example cocoalkyl dimethyl ammonium glycinate, N-acylaminopropyl-N,N-dimethyl ammonium glycinates, for example cocoacylaminopropyl dimethyl ammonium glycinate, and 2-alkyl-3- carboxymethyl-3-hydroxyethyl imidazolines containing 8 to 18 carbon atoms in the alkyl or acyl group and cocoacylaminoethyl hydroxyethyl carboxymethyl glycinate.
  • betaines such as the N-alkyl-N,N-dimethyl ammonium glycinates, for example cocoalkyl dimethyl ammonium glycinate, N-acylaminopropyl-N,N-dimethyl ammonium glycinates, for example cocoacylamino
  • Ampholytic surfactants are also suitable emulsifiers.
  • Ampholytic 220084 surfactants are surface-active compounds which, in addition to a C8/18 alkyl or acyl group, contain at least one free amino group and at least one ⁇ COOH- or -SO3H- group in the molecule and which are capable of forming inner salts.
  • ampholytic surfactants are N-alkyl glycines, N-alkyl propionic acids, N-alkylaminobutyric acids, N- alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropyl glycines, N-alkyl taurines, N-alkyl sarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids containing around 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethyl aminopropionate and C12/18 acyl sarcosine.
  • Antimicrobial agents The sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention can advantageously combined with an anti-microbial agent which act primarily against microorganisms, in particular bacteria, yeast and/or fungi and includes one or more anti-microbial agents such as Caprylhydroxamic Acid, o-Cymen-5-ol, Isopropylparaben, Capryloyl Glycine, Phenylpropanol, Tropolone, PCA Ethyl Cocoyl Arginate, 2-Methyl 5-Cyclohexylpentanol, Phenoxyethanol, Disodium EDTA, Methylparaben and its salts, Sodium Benzoate, Benzyl Alcohol, Potassium Sorbate, Benzyl Salicylate, Propylparaben, Sodium Methylparaben, Methylchloroisothiazolinone, Methylisothiazolinone, Ethy
  • the sunscreen product, cosmetic or pharmaceutical preparation or homecare product as defined herein is advantageously combined with at least one further antimicrobial agent which is different from the anti-microbial agents specified above.
  • the combination with a further antimicrobial agent provides reliable protection against microbial degradation and deterioration of the preparation, in particular during storage.
  • the further different antimicrobial agent provides reliable protection against other microorganisms as described above, for example Corynebacterium, Anaerococcus, Finegoldia, Moraxella, Porphyromonas, Fusobacterium, Malassezia, Peptoniphilus, Streptococcus, Lactobacillus, Gardnerella, Fannyhessea, Epidermophyton, Trichophyton, Cutibacterium.
  • the combination with a further different antimicrobial agent allows antimicrobial protection against different groups of microorganisms, and, thus, a broader spectrum of microorganism.
  • the further different antimicrobial agent in the context of the present invention is preferably selected from the group consisting of 2-benzylheptanol, alkyl (C 12-22) trimethyl ammonium bromide and chloride, ascorbic acid and salts thereof, benzalkonium bromide, benzalkonium chloride, benzalkonium saccharinate, benzethonium chloride, Benzoic Acid, camphor, cetylpyridinium chloride, chlorhexidine diacetate, chlorhexidine dihydrochloride, chlorocresol, chloroxylenol, Cyclohexylglycerin, Dimethyl phenylbutanol, Dimethyl phenylpropanol, ethanol, ethyl lauroyl arginate HCl, Ethyl Lauroyl Arginate Laurate, eucalyptol, gluconic acid and salts thereof, glycerin, hexamidine, hexamidine diisethionate
  • the aforesaid antimicrobial agents are used in the sunscreen, cosmetic or pharmaceutical preparation or homecare product either as a single component or preferably in a mixture with two or more further of said antimicrobial agents as specified above.
  • the antimicrobial agent is present in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product in an amount of 0.01 to 25.0 % by weight, preferably 0.02 to 15.0 % by weight, most preferred in an amount of 0.05 to 6.0 % by weight, based on the total weight of the final formulation.
  • the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention preferably includes one or more preservatives which are suitable or customary in sunscreen products, cosmetic or pharmaceutical preparations or homecare products.
  • Suitable and advantageously preservatives are, for example, benzoic acid, sodium benzoate, ammonium benzoate, butyl benzoate, calcium benzoate, ethyl benzoate, isobutyl benzoate, isopropyl benzoate, magnesium benzoate, mea-benzoate, methyl benzoate, phenyl benzoate, potassium benzoate, propyl benzoate, propionic acid, ammonium propionate, calcium propionate, magnesium propionate, potassium propionate, sodium propionate, salicylic acid, calcium salicylate, magnesium salicylate, measalicylate, sodium salicylate, potassium salicylate, teasalicylate, sorbic acid, calcium sorbate, sodium sorbate,
  • Drugs The sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention is preferably combined with one or more drugs.
  • the pharmaceutically active agent is selected from anti-acne agents, agents used to treat rosacea, analgesics, anesthetics, anorectals, antihistamines, anti-inflammatory agents including non-steroidal anti-inflammatory drugs, antibiotics, antifungals, antivirals, antimicrobials, anti-cancer actives, scabicides, pediculicides, antineoplastics, antiperspirants, antipruritics, antipsoriatic agents, antiseborrheic agents, biologically active proteins and peptides, burn treatment agents, cauterizing agents, depigmenting agents, depilatories, diaper rash treatment agents, enzymes, hair growth stimulants, hair growth retardants including eflornithine and its salts and analogs, hemostatics, kerotolytics, canker sore treatment agents, cold
  • the sunscreen product or cosmetic or pharmaceutical, in particular dermatological, preparation according to the first aspect of the present invention is intended for topical applications.
  • the term “topical” is understood to mean external applications on a mammal’s skin or mucosa, which are in particular for the protection, treatment, care and cleansing of the skin, scalp, eyelashes, eyebrows, nails, mucous membranes and hair.
  • the mammal is preferably a human.
  • the cosmetic or pharmaceutical preparation is either a rinse off or a leave on preparation.
  • the sunscreen products according to the present invention may be in the form of an aqueous solution, dispersions, a hydro alcoholic vehicle, a stick, an ointment, a gel, an aerosol (foams, sprays, propellant pump) and the like.
  • the sunscreen product, cosmetic or pharmaceutical, in particular dermatological, preparation or homecare product according to the first aspect of the present invention can be present in different forms, e.g.
  • the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the first aspect of the invention is a dispersion.
  • the term “dispersion” in the context of the present invention means, that the sunscreen product, cosmetic or pharmaceutical preparation or homecare product is a disperse two-phase system consisting of colloidal particles (disperse phase) and a medium in which they are suspended (disperse medium).
  • Such dispersions for example emulsions, comprise the at least one oil component (without UV-filters) preferably in an amount of ⁇ 1 % by weight, more preferably in an amount of ⁇ 3 % by weight.
  • the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the first aspect of the present invention takes various forms such as an emulsion, in particular a O/W emulsion, a W/O emulsion, a multiple emulsion, a hydrodispersion gel, a balm, a multiple emulsion of the water-in-oil type (W/O/WO) or of the oil-in-water type (O/W/O), PIT emulsion, Pickering emulsion, a micro- emulsion, a liquid, a lotion, a suspension, a milk, an ointment, a paste, a gel, a cream based, an oil based or a liposome-based formulation or a an aerosol such as foams and sprays, including all types of silicon based emulsions.
  • an emulsion in particular a O/W emulsion, a W/O emulsion, a multiple emulsion, a
  • the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention is in the form of an emulsion as defined herein, advantageously in the form of an oil-in-water (O/W) emulsion comprising an oily phase dispersed in an aqueous phase in the presence of an O/W or polymeric emulsifier.
  • O/W oil-in-water
  • the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention is a dispersion, preferably an emulsion
  • the oil component is present in the cosmetic or pharmaceutical preparation in an amount of 0.01 to 50.0 % by weight, based on the total weight of the composition.
  • the cosmetic or pharmaceutical preparation comprises the oil component in an amount of 0.1 to 45.0 % by weight, based on the total weight of the composition.
  • the oil component is advantageously used in the cosmetic or pharmaceutical preparation in an amount of at 1.0 to 40 % by weight, based on the total weight of the composition.
  • the sunscreen product, cosmetic or pharmaceutical, preferably dermatological, preparation or homecare product according to the first of the invention is a water free formulation, i.e. an oil formulation.
  • the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention is a water free formulation, i.e.
  • oil component is present in the cosmetic or pharmaceutical preparation in an amount of ⁇ 60 % by weight, preferably in an amount of ⁇ 75 % by weight, more preferably in an amount of ⁇ 90 % by weight, based on the total weight of the composition.
  • water free formulations include e.g. oils, skin butters, powders, lip stick, antiperspirant/deo sticks, and decorative cosmetics.
  • further water free formulations are likewise formulations on the basis of ethanol/diols/triols/glycols such as sprays or gels.
  • the sunscreen product, cosmetic or pharmaceutical preparation or homecare product as disclosed herein is an aqueous or an aqueous/alcoholic, preferably aqueous/ethanolic, or an aqueous/glycolic, or an alcoholic/glycolic, preferably ethanolic/glycolic, based solution.
  • this could be glycerin in water or alcohol compositions.
  • Said solutions are homogeneous one phase system of water/alcohol/glycol and additional components.
  • the aqueous/alcoholic or aqueous/glycolic or alcoholic/glycolic based solution comprises an aliphatic alcohol or a glycol in an amount of 0.1 to 70.0 % by weight, preferably in an amount of 0.5 to 60.0 % by weight, more preferably in an amount of 1.0 to 50.0 % by weight, based on the total weight of the solution.
  • the aliphatic alcohol is preferably selected from the group consisting of ethanol, isopropanol, n-propanol.
  • the glycol is preferably selected from the group consisting of glycerin, propylene glycol, 1,3-Propanediol, 1,2-Propanediol, 1,2–C5 to C10-alkanediols, butylene glycol or dipropylene glycol.
  • the overall water content in the final aqueous based solutions can be ⁇ 30 % by weight, more preferably ⁇ 40 % by weight, most preferably ⁇ 50 % by weight.
  • Such aqueous or aqueous/alcoholic or aqueous/glycolic or alcoholic/glycolic based solutions include for example deo/antiperspirant preparations, after shave, cleansing preparations, or anti-acne preparations.
  • the inventive composition is an impregnation solution in the form of an emulsion spray or ethanol/oil spray for wet wipes.
  • the above formulations or compositions are prepared according to usual and known methods.
  • the products and preparations according to the present invention are for cosmetic and/or non-therapeutic use for personal care, skin protection, skin care, sun care, scalp protection, scalp care, hair care, nail care, in particular for the prevention and treatment of skin conditions, intolerant or sensitive skin, skin irritation, skin reddening, wheals, pruritis (itching), skin aging, wrinkle formation, loss of skin volume, loss of skin 220084 elasticity, piment spots, pigment abnormalities, skin dryness, flaking, greasiness, hypopigmentation and/or hyperpigmentation of the skin; or a preparation for animal care.
  • Examples of personal care are preferably anti-ageing preparations, skin care emulsions, body oils, body lotions, cleansing lotions, face or body balms, after shave balms, after sun balms, deo emulsions, cationic emulsions, body gels, treatment creams, skin protection ointments, moisturizing gels, face and/or body moisturizers, light protective preparations (sunscreens), micellar water, hair sprays, color protection hair care products, skin lightning products, anti-dark-spot reparation, etc.
  • the cosmetic preparations include also make-ups, eye-care preparation, eye shadows, mascara, eyeliner, lip care preparation such as lip stick, lip gloss, mail care preparations, such as nail varnish, nail varnish removers, [0329]
  • the preparation according to the present invention is a preparation of medical use.
  • the pharmaceutical, in particular dermatological, composition according to the present invention is preferably a preparation for the prevention and treatment of a condition of the skin, mucosa, nails or hair.
  • the sunscreen product or cosmetic or pharmaceutical, in particular dermatological composition according to the first aspect of the present invention is applied to the skin, hair, scalp and/or nails in an adequate amount in such manner as is customary with sunscreen products or cosmetics and dermatological products.
  • the products and preparations according to the present invention are homecare products.
  • the home care products generally include laundry detergents (powder, liquid and tablet), fabric conditioners, dishwashing detergents (liquid and tablet), hard floor and surface cleaners, glass cleaners, carpet cleaners, oven cleaners, air fresheners, disinfectants, stain removers, car wash products. These products are usually manufactured in the form of a liquid, powder, spray, granules and others. 220084 [0333] Surprisingly, it was found that the addition of a mycosporine-like amino acid compounds or their salts as defined in the present application has the effect of improving the water resistance of a sunscreen product, cosmetic or pharmaceutical preparation or homecare product.
  • the increased water resistance makes said formulations more substantive to the skin or surfaces. Hence, important ingredients of said formulations, such as UV-filters, are not leached out when they come in contact with water and make the products more effective.
  • the water resistance is highly improved, i.e. increased, by the addition of a mycosporine-like amino acid compound (b) as defined therein.
  • the control samples containing no mycosporine-like amino acid compound (b) exhibited average or low water resistance properties.
  • An improvement of the water resistance can be observed when a mycosporine- like amino acid compound according to general formula (I) or general formula (II) as defined herein is added to a sunscreen product or cosmetic or pharmaceutical preparation.
  • a pronounced water resistance improving effect is especially observed for the mycosporine-like amino acid compounds according to general formula (II).
  • a mycosporine-like amino acid compound according to general formula (II) wherein X is S, a particular pronounced water resistance improving effect can be reached.
  • Particular beneficial are the mycosporine-like amino acid compounds according to the general formula (V) or (VI) when added to a sunscreenproduct or cosmetic or pharmaceutical preparation.
  • the mycosporine-like amino acid compounds are particularly effective in improving the water resistance of a sunscreen product or cosmetic or 220084 pharmaceutical preparation when they are in the form of an acid or in salt form as described above in detail.
  • the water resistance of a sunscreen product, a cosmetic or pharmaceutical preparation or homecare product can be increased by at least 5 %, in some instances by even more than 10 %, as it is demonstrated in the following examples.
  • the addition of MAA-2 salt in an amount of 1.0 % by weight results in a water resistance which is 5.9 % higher than the water resistance of the reference sample, i.e. the sample without the addition of the mycosporine-like amino acid compound.
  • the addition of MAA-2 salt in an amount of 3.0 % by weight even results in a water resistance which is 10.1 % higher than the water resistance of the control sample, i.e.
  • the addition of MAA-9 acid in an amount of 1.0 results in a water resistance which is 6.8 % higher than the water resistance of the reference sample, i.e. the sample without the addition of the mycosporine-like amino acid compound.
  • the addition of MAA-9 acid in an amount of 3.0 % by weight even results in a water resistance which is 10.6 % higher compared to the water resistance of the reference sample, i.e. the sample without the addition of the mycosporine-like amino acid compound.
  • the water 220084 resistance effect is especially pronounced for the mycosporine-like amino acid compounds MAA-12, MAA-13 and MAA-14 as specified above or any mixture thereof.
  • a mycosporine-like amino acid as defined herein to the sunscreen product or cosmetic or pharmaceutical preparation or homecare product the adhesion of the film forming agent on the skin or on surfaces can significantly be improved.
  • the combination of a film forming agent and a mycosporine-like amino acid result in a synergistic adherence effect of the sunscreen product or cosmetic or pharmaceutical preparation or homecare product on the skin or on a surface, to which the formulation is applied.
  • the improved adherence of the film forming agent in turn results in an improved water resistance, and, thus, provides excellent UV-protection even after bathing compared to products or preparations without the addition of the specified mycosporine-like amino acid compounds.
  • Such tenacity improving effect can be shown for the mycosporine-like amino acid compounds MAA-1, MAA-2, MAA-3, MAA-4, MAA-5, MAA-6, MAA-7, MAA-8, MAA-9, MAA-10 and MAA-11 or any mixture thereof.
  • Beneficial tenacity improving effect can be obtained preferably for MAA-2 and MAA-9 or a mixture thereof.
  • This tenacity effect can especially be observed when the mycosporine-like amino acid is in its salt form, i.e.
  • the combination of the film building agents with said mycosporine-like amino acid compounds show a distinctive adhesion of the sunscreen products, cosmetic or pharmaceutical preparation or homecare product on the skin or on surfaces, resulting in an improvement of the water resistance.
  • a particular adhesion improving effect can also be demonstrated for the Weinreb- amide derivatives, hydroxamate derivatives or alkylated hydroxamate derivatives of the mycosporine-like amino acid compounds as defined herein.
  • the adhesion improving effect is especially pronounced for the mycosporine-like amino acid compounds MAA-12, MAA-13 and MAA-14 as specified above or any mixture thereof.
  • the SPF can also be improved.
  • sunscreen products, cosmetic or pharmaceutical products or homecare product having a significant increase in water resistance as well as high sun protection factor (SPF).
  • SPDF sun protection factor
  • the improved SPF allows to reduce the amount of the UV- filter, in particular the primary organic and/or inorganic UV-filter, without affecting the envisaged SPF.
  • the present invention provides for a sunscreen product or cosmetic or pharmaceutical preparation wherein the water resistance is increased by at least 5 %, compared to a sunscreen product or cosmetic or pharmaceutical preparation without the mycosporine-like amino acid compound, preferred by at least 7.5 %, more preferred by at least 10 % and most preferred by at least 12.5 %.
  • the present invention relates in a further aspect to the use of a mycosporine-like amino acid compound (b) as defined herein or a mixture thereof for improving the water resistance of a sunscreen product or cosmetic or pharmaceutical preparation stabilizing the photostability of a UV-filter.
  • a mycosporine-like amino acid compound (b) as defined herein or a mixture thereof for improving the water resistance of a sunscreen product or cosmetic or pharmaceutical preparation stabilizing the photostability of a UV-filter.
  • the water resistance is increased by at least 7.5 %, more preferred by at least 10 % and most preferred by at least 12.5 %.
  • the present invention relates to a method of increasing the water resistance of a sunscreen product or cosmetic or pharmaceutical preparation. In the method an effective amount of at least one mycosporine-like amino acid compound as defined herein or a mixture thereof is added to said sunscreen product or cosmetic or pharmaceutical preparation.
  • Example 1 – Water resistance Test The water resistance test is carried out as in-vitro substantivity determination of UV-filters [0359] Principle: The formulation to be tested (emulsion, solution) is weighed on fabric strips with the help of an analytical balance and half of the fabric strips are immersed in water. Subsequently, all fabric strips are individually boiled, the extract solution is transferred to a measuring flask, filled up to 100 ml and measured in a UV-Vis spectrometer. The absorption maxima are used to determine the difference between the immersed/watered and the undiluted/non-watered samples and to calculate the substantivity. [0360] 1.
  • Sample preparation [0361] 1.1 Fabric: The fabric used in pre-treated as follows: the fabric is washed twice in a conventional washing machine with unscented mild detergent at 30 °C and then air- dried. Fabric made of 100 % pure new wool is suitable for the test. [0362] 1.2 Watered sample: 0.100 to 0.150 g of a formulation as specified in the following Table 3 to be tested is weighed on a treated wool fabric strip, as described before, of 5 x 10 cm in size. The formulation is distributed with the finger. The sample is allowed to dry for 30 minutes. Then the sample is weighed back.
  • Phase B The ingredients of phase B were mixed while stirring, in order to dissolve the ingredients.
  • the water phase will be cloudy in combination with sodium hydroxide solution. Afterwards, the water phase B is heated to 80 °C. Afterwards, the hot phase B was added to the hot phase A and homogenized (Ultra Turrax® T25: 13000rpm / 3 min). Finally, the mixture was cooled down to ambient temperature while stirring.
  • Table 3 220084
  • Results As can be retrieved from Table 3, the water resistance is highly improved, i.e. increased by the combination of the formulation with a certain mycosporine- like amino acid compound.
  • the control example (A) containing no mycosporine-like amino acid compound exhibited average or lower water resistance properties in comparison to the tested sample containing a mycosporine-like amino acid.
  • the addition of MAA-2 salt in an amount of 1.0 % by weight results in a water resistance which is 5.9 % higher than the water resistance of the reference sample, i.e. the sample without the addition of the mycosporine-like amino acid compound.
  • the addition of MAA- 2 salt in an amount of 3.0 % by weight even results in a water resistance which is 10.1 % higher than the water resistance of the control sample, i.e. containing none mycosporine- like amino acid compound.
  • Sunscreen products, cosmetic and pharmaceutical preparations are indicated as % by weight for all formulations: ⁇ Sunscreen Oil Spray with Ethanol, expected SPF 30, UVA/UVB balanced ⁇ Urban Sun Spray expected SPF 50+ ⁇ Sunscreen Spray (O/W), expected SPF 30 (all in one pot/cold manufacturing process) ⁇ UV protection water spray SPF 50 ⁇ Sunscreen Spray, *SPF 50+, Very Water Resistant** ⁇ Sunscreen Lotion (O/W), expected SPF 50* (cold/cold manufacturing process) ⁇ Beach Time Lotion SPF 30 ⁇ Anti-Sweat Sunscreen Lotion ⁇ Sun protection milk (w/o) ⁇ Face Protecting Watery Mousse expected SPF 30* ⁇ Full protection drops expected SPF 50 ⁇ Glow Brightener, expected SPF 50plus* ⁇ Sunscreen Fluid for acne-prone Skin, expected SPF 30 ⁇ No More Shine Fluid expected SPF50 ⁇ Light Sunscreen Fluid.

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Abstract

La présente invention concerne des produits d'écran solaire, des préparations cosmétiques ou pharmaceutiques ou des produits de soins à domicile comprenant au moins un filtre UV organique et/ou inorganique primaire, un certain composé d'acide aminé de type mycosporine et éventuellement au moins un agent filmogène. Les produits et les préparations fournissent une résistance à l'eau améliorée et, par conséquent, une performance de FPS accrue sans être collants de manière désagréable. En outre, la présente invention concerne l'utilisation d'un tel composé d'acide aminé de type mycosporine pour améliorer la résistance à l'eau et, ainsi, les performances de FPS, d'un produit d'écran solaire, d'une préparation cosmétique ou pharmaceutique ou d'un produit de soins à domicile comprenant au moins un filtre UV organique et/ou inorganique primaire et éventuellement au moins un agent filmogène. Enfin, la présente invention concerne une méthode d'augmentation de la résistance à l'eau et, ainsi, des performances de FPS, d'un produit d'écran solaire, d'une préparation cosmétique ou pharmaceutique ou d'un produit de soins à domicile comprenant au moins un filtre UV organique et/ou inorganique primaire et éventuellement au moins un agent filmogène par l'ajout d'un certain composé d'acide aminé de type mycosporine.
PCT/EP2022/072098 2022-08-05 2022-08-05 Composition avec résistance à l'eau améliorée Ceased WO2024027929A1 (fr)

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PCT/EP2022/072098 WO2024027929A1 (fr) 2022-08-05 2022-08-05 Composition avec résistance à l'eau améliorée
PCT/EP2023/071782 WO2024028511A1 (fr) 2022-08-05 2023-08-07 Composition avec résistance à l'eau améliorée
EP23754247.7A EP4565193A1 (fr) 2022-08-05 2023-08-07 Composition avec résistance à l'eau améliorée
CN202380054706.3A CN120379638A (zh) 2022-08-05 2023-08-07 具有改进的耐水性的组合物

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