WO2020163928A1 - Sunscreen composition, use of the sunscreen composition and process of manufacturing the sunscreen composition - Google Patents

Sunscreen composition, use of the sunscreen composition and process of manufacturing the sunscreen composition Download PDF

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Publication number
WO2020163928A1
WO2020163928A1 PCT/BR2019/050045 BR2019050045W WO2020163928A1 WO 2020163928 A1 WO2020163928 A1 WO 2020163928A1 BR 2019050045 W BR2019050045 W BR 2019050045W WO 2020163928 A1 WO2020163928 A1 WO 2020163928A1
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Prior art keywords
derivatives
sunscreen composition
composition
sunscreen
alkyl
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PCT/BR2019/050045
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French (fr)
Inventor
Antoniela GARDOLINSKI
Lais Moreira LIMA
Wagner PEREIRA
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L'oreal
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Priority to PCT/BR2019/050045 priority Critical patent/WO2020163928A1/en
Priority to BR112021012509-4A priority patent/BR112021012509B1/en
Publication of WO2020163928A1 publication Critical patent/WO2020163928A1/en

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00Barrier 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
    • A61Q17/04Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04Dispersions; Emulsions
    • A61K8/06Emulsions
    • A61K8/062Oil-in-water emulsions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/29Titanium; Compounds thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • A61K8/342Alcohols having more than seven atoms in an unbroken chain
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365Hydroxycarboxylic acids; Ketocarboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • A61K8/375Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42Amides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/442Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof substituted by amido group(s)
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/463Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4993Derivatives containing from 2 to 10 oxyalkylene groups
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/55Phosphorus compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60Sugars; Derivatives thereof
    • A61K8/604Alkylpolyglycosides; Derivatives thereof, e.g. esters
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/88Polyamides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52Stabilizers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59Mixtures
    • A61K2800/596Mixtures of surface active compounds

Definitions

  • the present invention is directed to new sunscreen compositions with high SPF and dry touch sensorial to the skin, uses of said sunscreen composition and a process of manufacturing the sunscreen compositions.
  • UVA/UVB sunscreen compositions used to accomplish photoprotection, namely, inorganic UV filters and organic UV filters.
  • the degree of UV protection afforded by a sunscreen composition is directly related to the amount and type of UV filters contained therein. The higher the amount of UV filters, the greater the degree of UV protection (UVA/UVB).
  • sunscreen compositions must provide good protection against the sun, a measure of which is the Sun Protection Factor (SPF) value, yet have satisfactory sensory perception, such as a smooth but not greasy feel upon application.
  • SPF Sun Protection Factor
  • this combination of properties has been difficult to achieve, particularly because many active sunscreen compounds themselves have an oily or greasy feel, and increasing their content tends to cause the final product to suffer from that effect.
  • sunscreen filters are oil-like and/or oil-soluble materials. High levels of sunscreen filters in sunscreen products render the products less appealing for their greasy skin feel, stickiness, long drying time, and leave shiny residue on the skin after application.
  • sunscreen compositions due to the great amount of sunscreen filters associated with great amount of pigments and further additional ingredients to ensure the good sensoriality in the O/W emulsion, it tends to be unstable.
  • the pigments are essential raw materials for delivering an additional attribute to the sunscreen composition, which is the uniformization of the skin tone and, consequently the appearance of the skin.
  • an additional attribute to the sunscreen composition which is the uniformization of the skin tone and, consequently the appearance of the skin.
  • association of pigments to a sunscreen composition results in a high complexity challenge to stabilize the emulsion.
  • the challenge of formulating a sunscreen composition having high amounts of UV filters, pigments and further additional ingredients associated with the unique sensorial described above is that such composition tends to be unstable and ineffective.
  • a stable sunscreen composition is desired, associated with easy application, good spreadability, less shine, which does not melt at high temperature on the face, has an imperceptible and dry touch, high SPF values, gives the ideal balance between hydration and oil control, uniformization of the skin’s tone and combines high protection with smoothness to the skin.
  • the inventors succeeded to overcome the problems of the state of the art and surprisingly revealed a stable sunscreen composition, even at high concentrations of pigments and organic UV filters, having a light feel and pleasant sensorial through a specific stabilizing surfactant system comprising at least one anionic surfactant and at least one non-ionic surfactant, organic UV filters and pigments.
  • the present invention is directed to new sunscreen compositions comprising (a) a stabilizing surfactant system comprising at least one anionic surfactant and at least one nonionic surfactant, (b) organic UV filters and (c) uncoated pigments.
  • composition of the present invention is stable over the time, also presents a high level of UV-protection in order to protect the skin from the damages of the sun, easy application, good spreadability, less shine, which does not melt on high temperature on the face, uniformization of the skin’s tone, has an imperceptible and dry touch and combines high protection with smoothness to the skin.
  • Figures 1 a and 1 b show the result of the centrifuge test for a composition according to Example 1 of the present invention.
  • Figures 2a and 2b show the result of the centrifuge test for a composition according to Example 2 of the present invention.
  • Figures 3a and 3b show the result of the centrifuge test for a composition according to Example 3 of the present invention.
  • Figures 4a and 4b show the result of the centrifuge test for a composition according to Example 4 of the present invention.
  • Figure 5 shows the result of the package temperature test for a composition according to Example 1 of the present invention.
  • Figure 6 shows the result of the package temperature test for a composition according to Example 2 of the present invention.
  • Figure 7 shows the result of the package temperature test for a composition according to Example 3 of the present invention.
  • Figure 8 shows the result of the package temperature test for a composition according to Example 4 of the present invention.
  • the sunscreen composition of the present invention comprises:
  • a stabilizing surfactant system comprising at least one anionic surfactant and at least one nonionic surfactant
  • composition according to the invention presents a dry touch sensorial performance, as well as a strong and robust stability of the composition over the time, even at high concentrations of pigments and organic UV filters.
  • the amount of stabilizing surfactant system in the composition of the present invention is ranging from about 1 % to 10% by weight and preferably from about 1 .5% to about 8% by weight, more preferably from about 1 .5% to about 6% by weight, including all ranges and sub-ranges there between, based on the total weight of the composition.
  • the stabilizing surfactant system of the present invention comprises at least one anionic surfactant in an amount ranging from about 0.1 % to about 8% by weight and preferably from about 0.1 % to about 5% by weight, more preferably from about 0.1 % to about 3% by weight, including all ranges and sub-ranges there between, based on the total weight of the composition.
  • the anionic surfactants of the present invention are select from disodium ethylene dicocamide PEG-15 disulfate, glyceryl stearate citrate and mixtures thereof.
  • the stabilizing surfactant system of the present invention comprises at least one non-ionic surfactant in an amount ranging from about 0.1 % to about 9.5% by weight, preferably from 0.5% to about 7% by weight, more preferably from about 1 % to about 5% by weight, including all ranges and sub ranges there between, based on the total weight of the composition.
  • non-ionic surfactants of the present invention are select from polyglyceryl-3 dicitrate/stearate, polyglyceryl-3 methylglucose distearate, arachidyl alcohol, behenyl alcohol, arachidyl glucoside, ceteareth-25, and mixtures thereof.
  • the amount of organic UV filters in the sunscreen composition of the invention preferably ranges from about 3% to about 50% by weight, preferably in an amount of from about 5% to about 40% by weight, more preferably about 7% to about 30% by weight, most preferably about 10% to about 25% by weight, based on the total weight of the composition.
  • the UV filters of the present invention are select from the group consisting of butyl methoxydibenzoylmethane, ethylhexyl salicylate, ethylhexyl triazone, octocrylene, homosalate and mixtures thereof.
  • the amount of the uncoated pigments in the sunscreen composition of the invention preferably ranges from about 0.1 % to about 20% by weight, more preferably from about 0.5% to about 10% by weight, and most preferably from about 1 % to about 10% by weight, based on the total weight of the composition.
  • the uncoated pigments of the present invention are select from the group of metal oxide pigments, such as titanium dioxide, zinc oxide, titanium oxide, iron oxide, zirconium oxide and cerium oxide, or mixtures thereof.
  • the sunscreen composition of the invention is in the form of an oil in water (O/W) emulsion and can be used as a daily product for the skin.
  • O/W oil in water
  • the pH of the sunscreen composition according to the present invention is generally between 4 and 6.
  • composition of the present invention presents a SPF of 30, 50, 60, 70 or 90.
  • the composition of the present invention presents a high level of UV-protection in order to protect the skin from the damages of the sun, easy application, good spreadability, less shine, which does not melt on high temperature in the face, has an imperceptible and dry touch and combines high protection with smoothness to the skin. Also, the composition of the present invention is stable over the time and presents enhanced emulsion stability. In another preferred embodiment, the present invention is related to the use of a composition for manufacturing a product for preventing sunburn, which can be used as sunscreen daily product.
  • the present invention is also related to a process of manufacturing a sunscreen composition that provides the consumer with the properties described above.
  • the process of manufacturing the sunscreen composition of the present invention comprises the following steps:
  • step (b) adding an aqueous phase to the oily phase of step (a) under mixing until complete formation of the emulsion.
  • the aqueous phase of step (b) is prepared by mixing water and at least one additional ingredient.
  • step (a) of the process of the present invention further comprises the mixing of at least one additional ingredient.
  • the least one additional ingredient of steps (a) and (b) is selected from the group consisting of inorganic UV filters, coated pigments, perfume/fragrance, preserving agents, solvents, actives, fatty compounds, vitamins, fillers, silicones and polymers.
  • the expression“at least” means one or more and thus includes individual components as well as mixtures/combinations.
  • ranges provided are meant to include every specific range within, and combination of sub ranges between, the given ranges.
  • a range from 1 -5 includes specifically 1 , 2, 3, 4 and 5, as well as sub ranges such as 2-5, 3-5, 2-3, 2-4, 1 -4, etc.
  • All ranges and values disclosed herein are inclusive and combinable. For examples, any value or point described herein that falls within a range described herein can serve as a minimum or maximum value to derive a sub-range, etc.
  • the stabilizing surfactant system of the present invention comprises at least one anionic surfactant and at least one non-ionic surfactant.
  • Anionic surfactants mean a surfactant comprising, as ionic or ionizable groups, only anionic groups. These anionic groups are chosen preferably from the groups CO2H, CO2-, SO3H, SO3-, OSO3H, OSO3- O2PO2H, O2PO2H and O2PO2 2 .
  • Non-limiting anionic surfactant(s) that may be used in the present invention are selected from the group comprising alkyl sulfates, alkyl ether sulfates, alkylamido ether sulfates, alkylaryl polyether sulfates, monoglyceride sulfates, sulfonates, such as alkylsulfonates, alkylamide sulfonates, alkylarylsulfonates, alpha- olefin sulfonates, paraffin sulfonates, sulfosuccinates, alkylsulfosuccinates, alkyl ether sulfosuccinates, alkylamide sulfosuccinates, alkyl sulfoacetates, acylsarcosinates, acylglutamates, alkylsulfosuccinamates, taurates and N-acyl N-methyltaurates,
  • anionic surfactants also comprise the dimeric surfactant of formula (I), described in WO 96/14926:
  • Ri and R3 denote, independently of each other, an alkyl radical containing from 1 to 25 carbon atoms;
  • R2 denotes a spacer consisting of a linear or branched alkylene chain containing from 1 to 12 carbon atoms
  • X denotes a group -(C2H40) a -(C3H60)bZ;
  • Y denotes a group -(C2H40) c -(C3H60)dZ
  • Z denotes a hydrogen atom or a radical -CH2-COOM, -SO3M, -P(0)(OM)2, -C2H4SO3M, or -C3HSSO3M group, in which M & M' represent H or an alkali metal or alkaline-earth metal or ammonium or alkanolammonium ion,
  • a and c independently of each other, range from 0 to 15,
  • a surfactant of this type is, particularly, the one identified by the INCI name: Disodium ethylene dicocamide PEG-15 disulfate, having the following structure:
  • RCO represents a coconut fatty acid radical and m + n has a mean value of 15.
  • the anionic surfactants of the present invention are select from disodium ethylene dicocamide PEG-15 disulfate, glyceryl stearate citrate and mixtures thereof.
  • Non-limiting examples of non-ionic surfactants useful in the present invention include, for example, alkyl- and polyalkyl- esters of glycerol, such as polyglyceryl-3 dicitrate/stearate, mixtures of alkyl- and polyalkyl- esters of glycerol with polyglyceryl, such as polyglyceryl-3 methylglucose distearate, oxyalkylenated (more particularly polyoxyethylenated) fatty acid esters of glycerol; oxyalkylenated fatty acid esters of sorbitan; oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty acid esters; oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty alcohol ethers; sugar esters, for instance sucrose stearate; fatty alcohols, fatty alcohol ethers of sugars, especially alkyl polygluco
  • the mixture of the alkyl polyglucoside as defined above with the corresponding fatty alcohol may be in the form of a self-emulsifying composition. Mention may also be made of lecithins and derivatives (e.g. Biophilic), sugar esters and sodium stearoyl lactylate.
  • non-ionic surfactants of the present invention are select from polyglyceryl-3 dicitrate/stearate, polyglyceryl-3 methylglucose distearate, arachidyl alcohol, behenyl alcohol, arachidyl glucoside, ceteareth-25, and mixtures thereof.
  • organic UV filters used in the composition of the present invention are selected from the group consisting of oil-soluble organic sunscreen ingredients and water-soluble organic sunscreen ingredients.
  • suitable organic UV filters of the present invention could be as follows:
  • oil-soluble organic sunscreen ingredient means any organic compound for screening out UV radiation, which can be fully dissolved in molecular form or miscible in an oil phase or which can be dissolved in colloidal form (for example in micellar form) in an oil fatty phase.
  • Non-limiting examples of oil-soluble organic sunscreen ingredients useful in the invention include, for example, cinnamic derivatives; anthranilates; salicylic derivatives; dibenzoylmethane derivatives; camphor derivatives; benzophenone derivatives; diphenylacrylate derivatives; triazine derivatives; benzotriazole derivatives; benzalmalonate derivatives, especially those cited in patent US5624663; benzimidazole derivatives; imidazolines; bis-benzoazolyl derivatives as described in patents EP669323 and US2463264; p-aminobenzoic acid (PABA) derivatives; methylene bis(hydroxyphenylbenzotriazole) derivatives as described in applications US5237071 , US5166355, GB2303549, DE19726184 and EP8931 19; benzoxazole derivatives as described in patent applications EP0832642, EP1027883, EP1300137 and DE10162844; screening polymers and screening silicones such as
  • cinnamic derivatives include, but are not limited to, ethylhexyl methoxycinnamate, isopropyl methoxycinnamate, isoamyl methoxycinnamate, DEA methoxycinnamate, diisopropyl methylcinnamate, glyceryl ethylhexanoate dimethoxycinnamate.
  • Suitable dibenzoylmethane derivatives include, but are not limited to, butyl methoxydibenzoylmethane and isopropyl dibenzoylmethane.
  • suitable salicylic derivatives include, but are not limited to, homosalate, ethylhexyl salicylate, dipropylene glycol salicylate and TEA salicylate.
  • Beta, beta -Diphenylacrylate derivatives
  • Suitable beta, beta -diphenylacrylate derivatives include, but are not limited to, octocrylene and etocrylene.
  • benzophenone derivatives include, but are not limited to, benzophenone-1 , benzophenone-2, benzophenone-3 or oxybenzone, benzophenone-4, benzophenone-5, benzophenone-6, benzophenone-8, benzophenone-9, benzophenone-12, n-hexyl 2-(4-diethylamino-2- hydroxybenzoyl)benzoate +” or as a mixture with octyl methoxycinnamate.
  • Suitable benzylidenecamphor derivatives include, but are not limited to, 3-benzylidene camphor manufactured, 4-methylbenzylidene camphor, polyacrylamidomethyl benzylidene camphor manufactured.
  • Suitable phenylbenzotriazole derivatives include, but are not limited to, drometrizole trisiloxane, methylene bis-benzotriazolyl tetramethylbutyl- phenol, or in micronized form as an aqueous dispersion.
  • Triazine derivatives examples include, but are not limited to, bis-ethylhexyloxyphenol methoxyphenyl triazine, ethylhexyl triazone, diethylhexyl butamido triazone, 2,4,6-tris(dineopentyl 4’-aminobenzalmalonate)-s-triazine, 2,4,6- tris(diisobutyl 4’-aminobenzalmalonate)s triazine, 2,4-bis(dineopentyl 4'- aminobenzalmalonate)-6-(n-butyl 4'-aminobenzoate)-s-triazine, symmetrical triazine screening agents described in patent US 6,225,467, patent application WO 2004/085412 (see compounds 6 and 9) or the document "Symmetrical Triazine Derivatives" IP.COM Journal, IP.COM Inc., West Hen
  • An example of a suitable anthranilic derivative includes, but is not limited to, menthyl anthranilate.
  • An example of a suitable imidazoline derivative includes, but is not limited to, ethylhexyl dimethoxybenzylidene dioxoimidazoline propionate.
  • Benzalmalonate derivative includes, but is not limited to, polyorganosiloxane containing benzalmalonate functions, for instance polysilicone-15.
  • An example of a suitable 4,4-diarylbutadiene derivative includes, but is not limited to, 1 -Dicarboxy(2,2’-dimethylpropyl)-4, 4-diphenyl-butadiene.
  • benzoxazole derivative includes, but is not limited to, 2,4-bis[5-(1 -dimethylpropyl)benzoxazol-2-yl-(4-phenyl)imino]-6-(2-ethylhexyl) imino-1 ,3,5-triazine, and mixtures thereof.
  • the oil-soluble organic sunscreen ingredient will be chosen from butyl methoxydibenzoylmethane, ethylhexyl salicylate, ethylhexyl triazone, octocrylene, drometrizole trisiloxane, bis-ethylhexyloxyphenol methoxyphenyl triazine, and mixtures thereof.
  • Water-soluble organic sunscreen ingredient means any organic compound for screening out UV radiation, which can be fully dissolved in molecular form or miscible in a liquid aqueous phase or which can be dissolved in colloidal form (for example in micellar form) in a liquid aqueous phase.
  • Non-limiting examples of water-soluble organic sunscreen ingredients useful in the invention include, for example, terephthalylidene dicamphor sulfonic acid (Ecamsule), phenylbenzimidazole sulfonic acid (Ensulizole), benzophenone-4, aminobenzoic acid (PABA), 4-Bis(polyethoxy)-para-aminobenzoic acid polyethoxyethyl ester (PEG-25 PABA), camphor benzalkonium methosulfate, methylene bis-benzotriazolyl tetramethylbutylphenol (Bisoctrizole), disodium phenyl dibenzimidazole tetrasulfonate (Bisdisulizole disodium), and tris-biphenyl triazine; their derivatives and corresponding salts; naphthalene bisimide derivatives such as those described in European patent application EP1990372 A2, the entire contents of which is hereby incorporated
  • the salts of the compounds that may be used according to the invention are chosen in particular from salts of alkali metals, for example sodium or potassium; salts of alkaline-earth metals, for example calcium, magnesium or strontium; metal salts, for example zinc, aluminum, manganese or copper; salts of ammonium of formula NH4+; quaternary ammonium salts; salts of organic amines, for instance salts of methylamine, dimethylamine, trimethylamine, triethylamine, ethylamine, 2- hydroxyethylamine, bis(2-hydroxyethyl)amine or tris(2-hydroxyethyl)amine; lysine or arginine salts.
  • Salts chosen from sodium, potassium, magnesium, strontium, copper, manganese or zinc salts are preferably used.
  • the sodium salt is preferably used.
  • the water-soluble organic sunscreen ingredient will be chosen from terephthalylidene dicamphor sulfonic acid, methylene bis-benzotriazolyl tetramethylbutylphenol, and mixtures thereof.
  • the suitable pigments used in the sunscreen composition of the present invention are uncoated pigments.
  • the uncoated pigments used in the sunscreen composition of the present invention are selected from the group consisting of metal oxide pigments, such as titanium dioxide, zinc oxide, titanium oxide, iron oxide, zirconium oxide and cerium oxide, or mixtures thereof.
  • composition of the invention may further comprise any usual cosmetically acceptable ingredient, which may be chosen especially from such as inorganic UV filters, coated pigments, perfume/fragrance, preserving agents, solvents, actives, fatty compounds, vitamins, fillers, silicones, polymers, and mixtures thereof.
  • cosmetically acceptable ingredient which may be chosen especially from such as inorganic UV filters, coated pigments, perfume/fragrance, preserving agents, solvents, actives, fatty compounds, vitamins, fillers, silicones, polymers, and mixtures thereof.
  • Suitable coated pigments are more particularly titanium oxides coated with silica such as the product, silica and iron oxide, silica and alumina, alumina such as the products, alumina and aluminum stearate, alumina and aluminum laurate, iron oxide and iron stearate, zinc oxide and zinc stearate, silica, alumina and silicone, silica, alumina, aluminum stearate and silicone, alumina and silicone, etc.
  • metal oxides may also be mentioned, especially titanium dioxide and cerium dioxide, including the silica-coated equiponderous mixture of titanium dioxide and cerium dioxide, as well as the alumina-silica- and silicone-coated mixture of titanium oxide and zinc dioxide, or the alumina-, silica- and glycerin-coated mixture of titanium dioxide and zinc dioxide.
  • Suitable polymers include, but are not limited to, aluminum starch octenylsuccinate, xanthan gum, poly C10-30 alkyl acrylate, acrylates/Cio-30 alkyl acrylate crosspolymer, styrene/acrylates copolymer, and mixtures thereof.
  • the composition may also comprise at least one silicon ingredient, which may be dimethicone and caprylyl methicone, among others.
  • Non-limiting example of preserving agent which can be used in accordance with the invention include phenoxyethanol.
  • Suitable fillers of the invention could be as examples of oil-absorbing fillers: mica, silica, zea may (corn) starch, magnesium oxide, nylon-12, nylon-66, cellulose, polyethylene, talc, talc (and) methicone, talc (and) dimethicone, perlite, sodium silicate, pumice, PTFE, polymethyl methacrylate, oryza sativa (rice) starch, aluminum starch octenylsuccinate, potato starch modified, alumina, silica silylate, calcium sodium borosilicate, magnesium carbonate, hydrated silica, dimethicone/vinyl dimethicone crosspolymer, sodium carboxylmethyl starch.
  • mica, silica, zea may (corn) starch, magnesium oxide, nylon-12, nylon-66, cellulose, polyethylene, talc, talc (and) methicone, talc (and) dimethicone, perlite, sodium silicate,
  • Suitable solvents include, but are not limited to water, alcohols, glycols and polyols such as glycerin, water, caprylyl glycol, pentylene glycol, propylene glycol, butylene glycol, C12-15 alkyl benzoate and mixtures thereof.
  • the solvent is present in a concentration from about 15 to 100% by weight, or from about 20 to about 85% by weight, or from about 30 to about 75% by weight, or from about 35 to about 75% by weight, or preferably from about 40 to about 75% by weight, and more preferably from about 45 to about 75% by weight, including ranges and sub-ranges there between, based on the total weight of the combinations and/or compositions of the present disclosure.
  • Suitable additional actives include, but are not limited to, disodium EDTA, triethanolamine, and mixtures thereof.
  • Exemplary of fat or oil materials include, but are not limited to, esters, fatty acids, synthetic oils, and hydrocarbons/paraffins, such as stearyl alcohol, myristic acid, palmitic acid silicones mineral oil, plant/vegetable oils, and mixtures thereof.
  • Non-limiting example of vitamins suitable for the composition of the present invention includes tocopherol.
  • silicones used in the composition of the present invention but not limited to are dimethicone and caprylyl methicone.
  • Exemplary of polymers include, but not limited to, aluminum starch octenylsuccinate, xanthan gam, acrylates/Cio-30 alkyl acrylate crosspolymer and styrene/acrylates copolymer.
  • the additional ingredients may represent from 60% to 85%, such as from 60% to 80% or such as from 65 to 80% by weight of the total weight of the composition of the invention.
  • Suitable compositions according to the present invention are as Examples 1 to 4, as follows:
  • Comparative compositions are as Examples 5 to 1 1 , as follows:
  • compositions according to examples 1 to 4 were prepared according to the following steps:
  • the first test was a centrifugation of the compositions according to examples 1 to 4, with temperature variation to predict phase separation, in both low and high centrifugation speeds (between 500 and 5000 rpm). After centrifugation, the stability of the compositions is both visually and analytically evaluated.
  • the second test was performed with packaged sunscreen compositions of examples 1 to 4, wherein the stability of the emulsion was visually evaluated after the packages were submit to temperature variations between 4°C and 60 Q C.
  • the results of the package temperature tests are shown in Figures 5 to 8, respectively, for examples 1 to 4. It is possible to observe that, even at high temperatures, the compositions according to the present invention did not shown phase separation.

Abstract

The present invention is directed to new sunscreen compositions comprising (a) a stabilizing surfactant system comprising at least one anionic surfactant and at least one nonionic surfactant; (b) organic UV filters; and (c) uncoated pigments. The composition of the present invention is stable over the time, also presents a high level of UV-protection in order to protect the skin from the damages of the sun, easy application, good spreadability, less shine, which does not melt on high temperature on the face, uniformization of the skin's tone, has an imperceptible and dry touch and combines high protection with smoothness to the skin.

Description

SUNSCREEN COMPOSITION, USE OF THE SUNSCREEN COMPOSITION AND PROCESS OF MANUFACTURING THE SUNSCREEN COMPOSITION
FIELD OF THE INVENTION
The present invention is directed to new sunscreen compositions with high SPF and dry touch sensorial to the skin, uses of said sunscreen composition and a process of manufacturing the sunscreen compositions.
BACKGROUND OF THE INVENTION
The photoprotection of keratinous materials, including both skin and hair, is considered of great importance in order to protect from sun-damage, sunburn, photo aging, as well as to decrease the chances of skin cancer development caused by exposure to ultraviolet (“UV”) radiation. There are typically two types of UVA/UVB sunscreen compositions used to accomplish photoprotection, namely, inorganic UV filters and organic UV filters.
The degree of UV protection afforded by a sunscreen composition is directly related to the amount and type of UV filters contained therein. The higher the amount of UV filters, the greater the degree of UV protection (UVA/UVB).
Particularly, sunscreen compositions must provide good protection against the sun, a measure of which is the Sun Protection Factor (SPF) value, yet have satisfactory sensory perception, such as a smooth but not greasy feel upon application. However, this combination of properties has been difficult to achieve, particularly because many active sunscreen compounds themselves have an oily or greasy feel, and increasing their content tends to cause the final product to suffer from that effect.
Also, most organic sunscreen filters are oil-like and/or oil-soluble materials. High levels of sunscreen filters in sunscreen products render the products less appealing for their greasy skin feel, stickiness, long drying time, and leave shiny residue on the skin after application.
Additionally, an important problem of sunscreen compositions is that, due to the great amount of sunscreen filters associated with great amount of pigments and further additional ingredients to ensure the good sensoriality in the O/W emulsion, it tends to be unstable.
The pigments are essential raw materials for delivering an additional attribute to the sunscreen composition, which is the uniformization of the skin tone and, consequently the appearance of the skin. However, such association of pigments to a sunscreen composition results in a high complexity challenge to stabilize the emulsion. The challenge of formulating a sunscreen composition having high amounts of UV filters, pigments and further additional ingredients associated with the unique sensorial described above is that such composition tends to be unstable and ineffective.
Therefore, a stable sunscreen composition is desired, associated with easy application, good spreadability, less shine, which does not melt at high temperature on the face, has an imperceptible and dry touch, high SPF values, gives the ideal balance between hydration and oil control, uniformization of the skin’s tone and combines high protection with smoothness to the skin.
Thus, the inventors succeeded to overcome the problems of the state of the art and surprisingly revealed a stable sunscreen composition, even at high concentrations of pigments and organic UV filters, having a light feel and pleasant sensorial through a specific stabilizing surfactant system comprising at least one anionic surfactant and at least one non-ionic surfactant, organic UV filters and pigments.
SUMMARY OF THE INVENTION
The present invention is directed to new sunscreen compositions comprising (a) a stabilizing surfactant system comprising at least one anionic surfactant and at least one nonionic surfactant, (b) organic UV filters and (c) uncoated pigments.
The composition of the present invention is stable over the time, also presents a high level of UV-protection in order to protect the skin from the damages of the sun, easy application, good spreadability, less shine, which does not melt on high temperature on the face, uniformization of the skin’s tone, has an imperceptible and dry touch and combines high protection with smoothness to the skin.
BRIEF DESCRIPTION OF THE DRAWINGS
Figures 1 a and 1 b show the result of the centrifuge test for a composition according to Example 1 of the present invention.
Figures 2a and 2b show the result of the centrifuge test for a composition according to Example 2 of the present invention.
Figures 3a and 3b show the result of the centrifuge test for a composition according to Example 3 of the present invention.
Figures 4a and 4b show the result of the centrifuge test for a composition according to Example 4 of the present invention. Figure 5 shows the result of the package temperature test for a composition according to Example 1 of the present invention.
Figure 6 shows the result of the package temperature test for a composition according to Example 2 of the present invention.
Figure 7 shows the result of the package temperature test for a composition according to Example 3 of the present invention.
Figure 8 shows the result of the package temperature test for a composition according to Example 4 of the present invention.
DETAILED DESCRIPTION OF THE INVENTION
In an embodiment, the sunscreen composition of the present invention comprises:
(a) a stabilizing surfactant system comprising at least one anionic surfactant and at least one nonionic surfactant;
(b) organic UV filters; and
(c) uncoated pigments.
The composition according to the invention, presents a dry touch sensorial performance, as well as a strong and robust stability of the composition over the time, even at high concentrations of pigments and organic UV filters.
In a preferred embodiment, the amount of stabilizing surfactant system in the composition of the present invention is ranging from about 1 % to 10% by weight and preferably from about 1 .5% to about 8% by weight, more preferably from about 1 .5% to about 6% by weight, including all ranges and sub-ranges there between, based on the total weight of the composition.
The stabilizing surfactant system of the present invention comprises at least one anionic surfactant in an amount ranging from about 0.1 % to about 8% by weight and preferably from about 0.1 % to about 5% by weight, more preferably from about 0.1 % to about 3% by weight, including all ranges and sub-ranges there between, based on the total weight of the composition.
In a preferred embodiment, the anionic surfactants of the present invention are select from disodium ethylene dicocamide PEG-15 disulfate, glyceryl stearate citrate and mixtures thereof.
In a preferred embodiment, the stabilizing surfactant system of the present invention comprises at least one non-ionic surfactant in an amount ranging from about 0.1 % to about 9.5% by weight, preferably from 0.5% to about 7% by weight, more preferably from about 1 % to about 5% by weight, including all ranges and sub ranges there between, based on the total weight of the composition.
In a preferred embodiment, the non-ionic surfactants of the present invention are select from polyglyceryl-3 dicitrate/stearate, polyglyceryl-3 methylglucose distearate, arachidyl alcohol, behenyl alcohol, arachidyl glucoside, ceteareth-25, and mixtures thereof.
The amount of organic UV filters in the sunscreen composition of the invention preferably ranges from about 3% to about 50% by weight, preferably in an amount of from about 5% to about 40% by weight, more preferably about 7% to about 30% by weight, most preferably about 10% to about 25% by weight, based on the total weight of the composition.
In a preferred embodiment, the UV filters of the present invention are select from the group consisting of butyl methoxydibenzoylmethane, ethylhexyl salicylate, ethylhexyl triazone, octocrylene, homosalate and mixtures thereof.
The amount of the uncoated pigments in the sunscreen composition of the invention preferably ranges from about 0.1 % to about 20% by weight, more preferably from about 0.5% to about 10% by weight, and most preferably from about 1 % to about 10% by weight, based on the total weight of the composition.
In a preferred embodiment, the uncoated pigments of the present invention are select from the group of metal oxide pigments, such as titanium dioxide, zinc oxide, titanium oxide, iron oxide, zirconium oxide and cerium oxide, or mixtures thereof.
The sunscreen composition of the invention is in the form of an oil in water (O/W) emulsion and can be used as a daily product for the skin.
The pH of the sunscreen composition according to the present invention is generally between 4 and 6.
In another preferred embodiment, the composition of the present invention presents a SPF of 30, 50, 60, 70 or 90.
Therefore, the composition of the present invention presents a high level of UV-protection in order to protect the skin from the damages of the sun, easy application, good spreadability, less shine, which does not melt on high temperature in the face, has an imperceptible and dry touch and combines high protection with smoothness to the skin. Also, the composition of the present invention is stable over the time and presents enhanced emulsion stability. In another preferred embodiment, the present invention is related to the use of a composition for manufacturing a product for preventing sunburn, which can be used as sunscreen daily product.
The present invention is also related to a process of manufacturing a sunscreen composition that provides the consumer with the properties described above.
The process of manufacturing the sunscreen composition of the present invention comprises the following steps:
(a) preparing an oily phase by mixing the organic UV filters, the uncoated pigments and the stabilizing surfactant system, wherein the oily phase is heated until complete homogenization; and
(b) adding an aqueous phase to the oily phase of step (a) under mixing until complete formation of the emulsion.
In a particular embodiment, the aqueous phase of step (b) is prepared by mixing water and at least one additional ingredient.
In another particular embodiment, the step (a) of the process of the present invention further comprises the mixing of at least one additional ingredient.
Preferably, the least one additional ingredient of steps (a) and (b) is selected from the group consisting of inorganic UV filters, coated pigments, perfume/fragrance, preserving agents, solvents, actives, fatty compounds, vitamins, fillers, silicones and polymers.
TERMS
As used herein, the expression“at least” means one or more and thus includes individual components as well as mixtures/combinations.
Other than in the operating examples, or where otherwise indicated, all numbers expressing quantities of ingredients and/or process conditions are to be understood as being modified in all instances by the term“about,” meaning within +/- 5% of the indicated number.
As used herein, all ranges provided are meant to include every specific range within, and combination of sub ranges between, the given ranges. Thus, a range from 1 -5, includes specifically 1 , 2, 3, 4 and 5, as well as sub ranges such as 2-5, 3-5, 2-3, 2-4, 1 -4, etc. All ranges and values disclosed herein are inclusive and combinable. For examples, any value or point described herein that falls within a range described herein can serve as a minimum or maximum value to derive a sub-range, etc. STABILIZING SURFACTANT SYSTEM
The stabilizing surfactant system of the present invention comprises at least one anionic surfactant and at least one non-ionic surfactant.
Anionic Surfactants
Anionic surfactants mean a surfactant comprising, as ionic or ionizable groups, only anionic groups. These anionic groups are chosen preferably from the groups CO2H, CO2-, SO3H, SO3-, OSO3H, OSO3- O2PO2H, O2PO2H and O2PO22 .
Non-limiting anionic surfactant(s) that may be used in the present invention are selected from the group comprising alkyl sulfates, alkyl ether sulfates, alkylamido ether sulfates, alkylaryl polyether sulfates, monoglyceride sulfates, sulfonates, such as alkylsulfonates, alkylamide sulfonates, alkylarylsulfonates, alpha- olefin sulfonates, paraffin sulfonates, sulfosuccinates, alkylsulfosuccinates, alkyl ether sulfosuccinates, alkylamide sulfosuccinates, alkyl sulfoacetates, acylsarcosinates, acylglutamates, alkylsulfosuccinamates, taurates and N-acyl N-methyltaurates, isethionates, N-acylisethionates, N-acyltaurates, phosphates and alkyl phosphates, salts of alkyl monoesters and polyglycoside-polycarboxylic acids, acyllactylates, mixed esters of organic acids with glycerol, such as glyceryl stearate citrate and as glyceryl stearate lactate, salts of D-galactoside uronic acids, salts of alkyl ether carboxylic acids, salts of alkyl aryl ether carboxylic acids, and salts of alkylamido ether carboxylic acids; or the non-salified forms of all of these compounds, the alkyl and acyl groups of all of these compounds containing from 6 to 24 carbon atoms and the aryl group denoting a phenyl group. Some of these compounds may be oxyethylenated and then preferably comprise from 1 to 50 ethylene oxide units.
Further examples of anionic surfactants also comprise the dimeric surfactant of formula (I), described in WO 96/14926:
Figure imgf000007_0001
in which:
Ri and R3 denote, independently of each other, an alkyl radical containing from 1 to 25 carbon atoms;
R2 denotes a spacer consisting of a linear or branched alkylene chain containing from 1 to 12 carbon atoms;
X denotes a group -(C2H40)a-(C3H60)bZ;
Y denotes a group -(C2H40)c-(C3H60)dZ;
in which
Z denotes a hydrogen atom or a radical -CH2-COOM, -SO3M, -P(0)(OM)2, -C2H4SO3M, or -C3HSSO3M group, in which M & M' represent H or an alkali metal or alkaline-earth metal or ammonium or alkanolammonium ion,
a and c, independently of each other, range from 0 to 15,
b and d, independently of each other, range from 0 to 10, and the sum of a + b + c + d ranges from 1 to 25; and n ranges from 1 to 10. A surfactant of this type is, particularly, the one identified by the INCI name: Disodium ethylene dicocamide PEG-15 disulfate, having the following structure:
Figure imgf000008_0001
wherein RCO represents a coconut fatty acid radical and m + n has a mean value of 15.
In a preferred embodiment, the anionic surfactants of the present invention are select from disodium ethylene dicocamide PEG-15 disulfate, glyceryl stearate citrate and mixtures thereof.
Non-Ionic Surfactants
Non-limiting examples of non-ionic surfactants useful in the present invention include, for example, alkyl- and polyalkyl- esters of glycerol, such as polyglyceryl-3 dicitrate/stearate, mixtures of alkyl- and polyalkyl- esters of glycerol with polyglyceryl, such as polyglyceryl-3 methylglucose distearate, oxyalkylenated (more particularly polyoxyethylenated) fatty acid esters of glycerol; oxyalkylenated fatty acid esters of sorbitan; oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty acid esters; oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty alcohol ethers; sugar esters, for instance sucrose stearate; fatty alcohols, fatty alcohol ethers of sugars, especially alkyl polyglucosides (APGs) such as decyl glucoside, lauryl glucoside, cetostearyl glucoside, optionally as a mixture with cetostearyl alcohol, and also arachidyl glucoside, for example in the form of a mixture of arachidyl alcohol, behenyl alcohol and arachidyl glucoside. According to one particular embodiment of the invention, the mixture of the alkyl polyglucoside as defined above with the corresponding fatty alcohol may be in the form of a self-emulsifying composition. Mention may also be made of lecithins and derivatives (e.g. Biophilic), sugar esters and sodium stearoyl lactylate.
In a preferred embodiment, the non-ionic surfactants of the present invention are select from polyglyceryl-3 dicitrate/stearate, polyglyceryl-3 methylglucose distearate, arachidyl alcohol, behenyl alcohol, arachidyl glucoside, ceteareth-25, and mixtures thereof.
ORGANIC UV FILTERS
The organic UV filters used in the composition of the present invention are selected from the group consisting of oil-soluble organic sunscreen ingredients and water-soluble organic sunscreen ingredients. Non-limiting suitable organic UV filters of the present invention could be as follows:
Oil-soluble organic sunscreen ingredient
The “oil-soluble organic sunscreen ingredient” means any organic compound for screening out UV radiation, which can be fully dissolved in molecular form or miscible in an oil phase or which can be dissolved in colloidal form (for example in micellar form) in an oil fatty phase.
Non-limiting examples of oil-soluble organic sunscreen ingredients useful in the invention include, for example, cinnamic derivatives; anthranilates; salicylic derivatives; dibenzoylmethane derivatives; camphor derivatives; benzophenone derivatives; diphenylacrylate derivatives; triazine derivatives; benzotriazole derivatives; benzalmalonate derivatives, especially those cited in patent US5624663; benzimidazole derivatives; imidazolines; bis-benzoazolyl derivatives as described in patents EP669323 and US2463264; p-aminobenzoic acid (PABA) derivatives; methylene bis(hydroxyphenylbenzotriazole) derivatives as described in applications US5237071 , US5166355, GB2303549, DE19726184 and EP8931 19; benzoxazole derivatives as described in patent applications EP0832642, EP1027883, EP1300137 and DE10162844; screening polymers and screening silicones such as those described especially in patent application WO 93/04665; dimers derived from alkyl- styrene such as those described in patent application DE 19855649; 4,4- diarylbutadienes such as those described in patent applications EP0967200, DE19746654, DE19755649, EP-A-1008586, EP1 133980 and EP1 133981 , merocyanine derivatives such as those described in patent applications WO 04/006878, WO 05/058269 and WO 06/032741 ; and mixtures thereof, the entire contents of the patents and patent applications being incorporated by reference in their entirety.
As examples of other suitable oil-soluble organic sunscreen ingredients, mention may be made of those denoted hereinbelow under their INCI name:
Cinnamic derivatives:
Examples of suitable cinnamic derivatives include, but are not limited to, ethylhexyl methoxycinnamate, isopropyl methoxycinnamate, isoamyl methoxycinnamate, DEA methoxycinnamate, diisopropyl methylcinnamate, glyceryl ethylhexanoate dimethoxycinnamate.
Dibenzoylmethane derivatives:
Examples of suitable dibenzoylmethane derivatives include, but are not limited to, butyl methoxydibenzoylmethane and isopropyl dibenzoylmethane.
Salicylic derivatives:
Examples of suitable salicylic derivatives include, but are not limited to, homosalate, ethylhexyl salicylate, dipropylene glycol salicylate and TEA salicylate.
Beta, beta -Diphenylacrylate derivatives:
Examples of suitable beta, beta -diphenylacrylate derivatives include, but are not limited to, octocrylene and etocrylene.
Benzophenone derivatives:
Examples of suitable benzophenone derivatives include, but are not limited to, benzophenone-1 , benzophenone-2, benzophenone-3 or oxybenzone, benzophenone-4, benzophenone-5, benzophenone-6, benzophenone-8, benzophenone-9, benzophenone-12, n-hexyl 2-(4-diethylamino-2- hydroxybenzoyl)benzoate +” or as a mixture with octyl methoxycinnamate.
Benzylidenecamphor derivatives:
Examples of suitable benzylidenecamphor derivatives include, but are not limited to, 3-benzylidene camphor manufactured, 4-methylbenzylidene camphor, polyacrylamidomethyl benzylidene camphor manufactured.
Phenylbenzotriazole derivatives:
Examples of suitable phenylbenzotriazole derivatives include, but are not limited to, drometrizole trisiloxane, methylene bis-benzotriazolyl tetramethylbutyl- phenol, or in micronized form as an aqueous dispersion.
Triazine derivatives: Examples of suitable triazine derivatives include, but are not limited to, bis-ethylhexyloxyphenol methoxyphenyl triazine, ethylhexyl triazone, diethylhexyl butamido triazone, 2,4,6-tris(dineopentyl 4’-aminobenzalmalonate)-s-triazine, 2,4,6- tris(diisobutyl 4’-aminobenzalmalonate)s triazine, 2,4-bis(dineopentyl 4'- aminobenzalmalonate)-6-(n-butyl 4'-aminobenzoate)-s-triazine, symmetrical triazine screening agents described in patent US 6,225,467, patent application WO 2004/085412 (see compounds 6 and 9) or the document "Symmetrical Triazine Derivatives" IP.COM Journal, IP.COM Inc., West Henrietta, NY, US (20 September 2004), especially 2,4,6-tris(biphenyl)-1 ,3,5-triazines (in particular 2,4,6-tris(biphenyl-4- yl)-1 ,3,5-triazine and 2,4,6-tris(terphenyl)-1 ,3,5-triazine, which is included in patent applications WO 06/035000, WO 06/034982, WO 06/034991 , WO 06/035007, WO 2006/034992 and WO 2006/034985).
Anthranilic derivatives:
An example of a suitable anthranilic derivative includes, but is not limited to, menthyl anthranilate.
Imidazoline derivatives:
An example of a suitable imidazoline derivative includes, but is not limited to, ethylhexyl dimethoxybenzylidene dioxoimidazoline propionate.
Benzalmalonate derivatives:
An example of a suitable Benzalmalonate derivative includes, but is not limited to, polyorganosiloxane containing benzalmalonate functions, for instance polysilicone-15.
4,4-Diarylbutadiene derivatives:
An example of a suitable 4,4-diarylbutadiene derivative includes, but is not limited to, 1 -Dicarboxy(2,2’-dimethylpropyl)-4, 4-diphenyl-butadiene.
Benzoxazole derivatives:
An example of suitable benzoxazole derivative includes, but is not limited to, 2,4-bis[5-(1 -dimethylpropyl)benzoxazol-2-yl-(4-phenyl)imino]-6-(2-ethylhexyl) imino-1 ,3,5-triazine, and mixtures thereof.
Preferably, the oil-soluble organic sunscreen ingredient will be chosen from butyl methoxydibenzoylmethane, ethylhexyl salicylate, ethylhexyl triazone, octocrylene, drometrizole trisiloxane, bis-ethylhexyloxyphenol methoxyphenyl triazine, and mixtures thereof.
Water-soluble organic sunscreen ingredient The“water-soluble organic sunscreen ingredient” means any organic compound for screening out UV radiation, which can be fully dissolved in molecular form or miscible in a liquid aqueous phase or which can be dissolved in colloidal form (for example in micellar form) in a liquid aqueous phase.
Non-limiting examples of water-soluble organic sunscreen ingredients useful in the invention include, for example, terephthalylidene dicamphor sulfonic acid (Ecamsule), phenylbenzimidazole sulfonic acid (Ensulizole), benzophenone-4, aminobenzoic acid (PABA), 4-Bis(polyethoxy)-para-aminobenzoic acid polyethoxyethyl ester (PEG-25 PABA), camphor benzalkonium methosulfate, methylene bis-benzotriazolyl tetramethylbutylphenol (Bisoctrizole), disodium phenyl dibenzimidazole tetrasulfonate (Bisdisulizole disodium), and tris-biphenyl triazine; their derivatives and corresponding salts; naphthalene bisimide derivatives such as those described in European patent application EP1990372 A2, the entire contents of which is hereby incorporated by reference; and cinnamido amine cationic quaternary salts and derivatives such as those described in United States Patent 5,601 ,81 1 , the entire contents of which is hereby incorporated by reference, and mixtures thereof.
The salts of the compounds that may be used according to the invention are chosen in particular from salts of alkali metals, for example sodium or potassium; salts of alkaline-earth metals, for example calcium, magnesium or strontium; metal salts, for example zinc, aluminum, manganese or copper; salts of ammonium of formula NH4+; quaternary ammonium salts; salts of organic amines, for instance salts of methylamine, dimethylamine, trimethylamine, triethylamine, ethylamine, 2- hydroxyethylamine, bis(2-hydroxyethyl)amine or tris(2-hydroxyethyl)amine; lysine or arginine salts. Salts chosen from sodium, potassium, magnesium, strontium, copper, manganese or zinc salts are preferably used. The sodium salt is preferably used.
Preferably, the water-soluble organic sunscreen ingredient will be chosen from terephthalylidene dicamphor sulfonic acid, methylene bis-benzotriazolyl tetramethylbutylphenol, and mixtures thereof.
UNCOATED PIGMENTS
The suitable pigments used in the sunscreen composition of the present invention are uncoated pigments.
In a preferred embodiment, the uncoated pigments used in the sunscreen composition of the present invention are selected from the group consisting of metal oxide pigments, such as titanium dioxide, zinc oxide, titanium oxide, iron oxide, zirconium oxide and cerium oxide, or mixtures thereof.
ADDITIONAL INGREDIENTS
In addition to the essential components described hereinbefore, the composition of the invention may further comprise any usual cosmetically acceptable ingredient, which may be chosen especially from such as inorganic UV filters, coated pigments, perfume/fragrance, preserving agents, solvents, actives, fatty compounds, vitamins, fillers, silicones, polymers, and mixtures thereof.
A person skilled in the art will take care to select the optional additional ingredients and/or the amount thereof such that the advantageous properties of the composition according to the invention are not, or are not substantially, adversely affected by the envisaged addition.
Suitable coated pigments are more particularly titanium oxides coated with silica such as the product, silica and iron oxide, silica and alumina, alumina such as the products, alumina and aluminum stearate, alumina and aluminum laurate, iron oxide and iron stearate, zinc oxide and zinc stearate, silica, alumina and silicone, silica, alumina, aluminum stearate and silicone, alumina and silicone, etc.
Mixtures of metal oxides may also be mentioned, especially titanium dioxide and cerium dioxide, including the silica-coated equiponderous mixture of titanium dioxide and cerium dioxide, as well as the alumina-silica- and silicone-coated mixture of titanium oxide and zinc dioxide, or the alumina-, silica- and glycerin-coated mixture of titanium dioxide and zinc dioxide.
Suitable polymers include, but are not limited to, aluminum starch octenylsuccinate, xanthan gum, poly C10-30 alkyl acrylate, acrylates/Cio-30 alkyl acrylate crosspolymer, styrene/acrylates copolymer, and mixtures thereof.
The composition may also comprise at least one silicon ingredient, which may be dimethicone and caprylyl methicone, among others.
Non-limiting example of preserving agent which can be used in accordance with the invention include phenoxyethanol.
Suitable fillers of the invention could be as examples of oil-absorbing fillers: mica, silica, zea may (corn) starch, magnesium oxide, nylon-12, nylon-66, cellulose, polyethylene, talc, talc (and) methicone, talc (and) dimethicone, perlite, sodium silicate, pumice, PTFE, polymethyl methacrylate, oryza sativa (rice) starch, aluminum starch octenylsuccinate, potato starch modified, alumina, silica silylate, calcium sodium borosilicate, magnesium carbonate, hydrated silica, dimethicone/vinyl dimethicone crosspolymer, sodium carboxylmethyl starch.
Suitable solvents include, but are not limited to water, alcohols, glycols and polyols such as glycerin, water, caprylyl glycol, pentylene glycol, propylene glycol, butylene glycol, C12-15 alkyl benzoate and mixtures thereof.
In various embodiments, the solvent is present in a concentration from about 15 to 100% by weight, or from about 20 to about 85% by weight, or from about 30 to about 75% by weight, or from about 35 to about 75% by weight, or preferably from about 40 to about 75% by weight, and more preferably from about 45 to about 75% by weight, including ranges and sub-ranges there between, based on the total weight of the combinations and/or compositions of the present disclosure.
Suitable additional actives include, but are not limited to, disodium EDTA, triethanolamine, and mixtures thereof.
Exemplary of fat or oil materials include, but are not limited to, esters, fatty acids, synthetic oils, and hydrocarbons/paraffins, such as stearyl alcohol, myristic acid, palmitic acid silicones mineral oil, plant/vegetable oils, and mixtures thereof.
Non-limiting example of vitamins suitable for the composition of the present invention includes tocopherol.
Examples of silicones used in the composition of the present invention but not limited to are dimethicone and caprylyl methicone.
Exemplary of polymers, include, but not limited to, aluminum starch octenylsuccinate, xanthan gam, acrylates/Cio-30 alkyl acrylate crosspolymer and styrene/acrylates copolymer.
The additional ingredients may represent from 60% to 85%, such as from 60% to 80% or such as from 65 to 80% by weight of the total weight of the composition of the invention.
By way of non-limiting illustration, the invention will now be described with reference to the following examples.
EXAMPLES
EXAMPLES 1 TO 4
Suitable compositions according to the present invention are as Examples 1 to 4, as follows:
Figure imgf000014_0001
Figure imgf000015_0001
EXAMPLES 5 TO 1 1
Comparative compositions are as Examples 5 to 1 1 , as follows:
Figure imgf000015_0002
Figure imgf000016_0001
EXAMPLE 12
The compositions according to examples 1 to 4 were prepared according to the following steps:
Step (a): Prepare an oily phase by mixing the UV filters, the pigments, the surfactants, C12-15 alkyl benzoate and xanthan gum until total homogenization;
Step (b): Prepare an aqueous phase by mixing the water, caprylyl glycol and phenoxyethanol;
Step (c): Add the aqueous phase of step (b) to the oily phase of step (a) under mixing until complete formation of the emulsion.
EXAMPLE 13 In order to demonstrate the emulsion stability of the composition according to the present invention, two different stability tests were performed.
Test 1 - Centrifuge Test
The first test was a centrifugation of the compositions according to examples 1 to 4, with temperature variation to predict phase separation, in both low and high centrifugation speeds (between 500 and 5000 rpm). After centrifugation, the stability of the compositions is both visually and analytically evaluated.
The results of the centrifugation tests are shown in Figures 1 to 4, respectively, for examples 1 to 4, wherein “a” indicates the result of the visual evaluation and“b” the analytical data of the stability index along time. It is possible to observe that the sunscreen compositions according to the present invention did not shown phase separation in the visual evaluation and exhibited low instability indexes during centrifugation.
Test 2 - Package Temperature Test
The second test was performed with packaged sunscreen compositions of examples 1 to 4, wherein the stability of the emulsion was visually evaluated after the packages were submit to temperature variations between 4°C and 60QC. The results of the package temperature tests are shown in Figures 5 to 8, respectively, for examples 1 to 4. It is possible to observe that, even at high temperatures, the compositions according to the present invention did not shown phase separation.

Claims

SET OF CLAIMS
1. A sunscreen composition comprising:
(a) a stabilizing surfactant system comprising:
(i) at least one anionic surfactant selected from the group consisting of: alkyl sulfates, alkyl ether sulfates, alkylamido ether sulfates, alkylaryl polyether sulfates, monoglyceride sulfates, sulfonates, such as alkylsulfonates, alkylamide sulfonates, alkylarylsulfonates, alpha-olefin sulfonates, paraffin sulfonates, sulfosuccinates, alkylsulfosuccinates, alkyl ether sulfosuccinates, alkylamide sulfosuccinates, alkyl sulfoacetates, acylsarcosinates, acylglutamates, alkylsulfosuccinamates, taurates, N-methyltaurates and N-acyltaurates, isethionates, N-acylisethionates, phosphates and alkyl phosphates, salts of alkyl monoesters and polyglycoside-polycarboxylic acids, acyllactylates, mixed esters of organic acids with glycerol, such as glyceryl stearate citrate and glyceryl stearate lactate, salts of D- galactoside uronic acids, salts of alkyl ether carboxylic acids, salts of alkyl aryl ether carboxylic acids, and salts of alkylamido ether carboxylic acids; or the non-salified forms of all of these compounds, the alkyl and acyl groups of all of these compounds containing from 6 to 24 carbon atoms, and dimeric anionic surfactants represented by formula (I):
Figure imgf000018_0001
in which:
Ri and Fb denote, independently of each other, an alkyl radical containing from 1 to 25 carbon atoms;
R2 denotes a spacer consisting of a linear or branched alkylene chain containing from 1 to 12 carbon atoms;
X denotes a group -(C2H40)a-(C3H60)bZ;
Y denotes a group -(C2H40)c-(C3H60)dZ;
in which
Z denotes a hydrogen atom or a radical -CH2-COOM, -SO3M, -P(0)(0M)2, -C2H4SO3M, or -C3HSSO3M group, in which M & M' represent H or an alkali metal or alkaline-earth metal or ammonium or alkanolammonium ion,
a and c, independently of each other, range from 0 to 15, b and d, independently of each other, range from 0 to 10, and
the sum of a + b + c + d ranges from 1 to 25; and n ranges from 1 to 10; and
(ii) at least one nonionic surfactant selected from the group consisting of: alkyl- and polyalkyl- esters of glycerol, mixtures of alkyl- and polyalkyl- esters of glycerol with polyglyceryl, oxyalkylenated fatty acid esters of glycerol; oxyalkylenated fatty acid esters of sorbitan; oxyalkylenated fatty acid esters; oxyalkylenated fatty alcohol ethers, sugar esters, fatty alcohols, fatty alcohol ethers of sugars;
(b) organic UV filters; and
(c) uncoated pigments.
2. The sunscreen composition, according to claim 1 , comprising from 1 % to 10% by weight of stabilizing surfactant system, including all ranges and sub ranges there between, based on the total weight of the composition.
3. The sunscreen composition, according to claim 1 , wherein the stabilizing surfactant system comprises at least one anionic surfactant in an amount ranging from 0.1 % to 8% by weight, including all ranges and sub-ranges there between, based on the total weight of the composition.
4. The sunscreen composition, according to claim 1 , wherein the stabilizing surfactant system comprises at least one nonionic surfactant in an amount ranging from 0.1 % to 9.5% by weight, including all ranges and sub-ranges there between, based on the total weight of the composition.
5. The sunscreen composition, according to claim 1 , wherein the organic UV filters in the sunscreen composition ranges from 3% to 50% by weight, based on the total weight of the composition.
6. The sunscreen composition, according to claim 1 , wherein the amount of the uncoated pigments in the sunscreen composition of the invention ranges from 0.1 % to 20% by weight, based on the total weight of the composition.
7. The sunscreen composition, according to claim 1 , wherein the at least one anionic surfactant is selected from the group consisting of glyceryl stearate citrate and disodium ethylene dicocamide peg-15 disulfate.
8. The sunscreen composition, according to claim 1 , wherein the at least one non-ionic surfactant is selected from the group consisting of polyglyceryl-3 dicitrate/stearate, polyglyceryl-3 methylglucose distearate, arachidyl alcohol, behenyl alcohol, arachidyl glucoside and ceteareth-25.
9. The sunscreen composition, according to claim 1 , wherein the organic UV filters are selected from the group consisting of oil-soluble organic sunscreen ingredients and water-soluble organic sunscreen ingredients.
10. The sunscreen composition, according to claim 9, wherein the oil- soluble organic sunscreen ingredients are selected from the group consisting of cinnamic derivatives, anthranilates, salicylic derivatives; dibenzoylmethane derivatives, camphor derivatives; benzophenone derivatives; diphenylacrylate derivatives; triazine derivatives; benzotriazole derivatives; benzalmalonate derivatives, benzimidazole derivatives; imidazolines; bis-benzoazolyl derivatives; p-aminobenzoic acid (PABA) derivatives; methylene bis(hydroxyphenylbenzotriazole), benzoxazole derivatives and mixtures thereof.
1 1 . The sunscreen composition, according to claim 9, wherein water- soluble organic sunscreen ingredients are selected from the group consisting of terephthalylidene dicamphor sulfonic acid, phenylbenzimidazole sulfonic acid, benzophenone-4, aminobenzoic acid, 4-Bis(polyethoxy)-para-aminobenzoic acid polyethoxyethyl ester, camphor benzalkonium methosulfate, methylene bis- benzotriazolyl tetramethylbutylphenol, disodium phenyl dibenzimidazole tetrasulfonate and tris-biphenyl triazine; their derivatives and corresponding salts; and mixtures thereof.
12. The sunscreen composition, according to claim 1 , wherein the uncoated pigments are selected from the group consisting of metal oxide pigments, such as titanium dioxide, zinc oxide, titanium oxide, iron oxide, zirconium oxide and cerium oxide, or mixtures thereof.
13. The sunscreen composition, according to claim 1 , wherein it further comprises additional ingredients selected from inorganic UV filters, coated pigments, perfume/fragrance, preserving agents, solvents, actives, fatty compounds, vitamins, fillers, silicones, polymers and mixtures thereof.
14. The sunscreen composition, according to claim 1 , wherein it is in the form of an O/W emulsion.
15. Use of the sunscreen composition, as defined in claim 1 , wherein it is for the manufacture of a product to be used as sunscreen daily product.
16. A process of manufacturing the sunscreen composition, as defined in claim 1 , comprising the following steps: (a) preparing an oily phase by mixing the organic UV filters, the uncoated pigments and the stabilizing surfactant system, wherein the oily phase is heated until complete homogenization;
(b) adding an aqueous phase to the oily phase of step (a) under mixing until complete formation of the emulsion.
17. The process, according to claim 16, wherein the aqueous phase is prepared by mixing water and at least one additional ingredient.
18. The process, according claim 16, wherein step (a) further comprises the mixing of at least one additional ingredient.
19. The process, according to claim 17 or 18, wherein the at least one additional ingredient is selected from the group consisting of inorganic UV filters, coated pigments, perfume/fragrance, preserving agents, solvents, actives, fatty compounds, vitamins, fillers, silicones and polymers.
PCT/BR2019/050045 2019-02-13 2019-02-13 Sunscreen composition, use of the sunscreen composition and process of manufacturing the sunscreen composition WO2020163928A1 (en)

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