- Photodegradation of avobenzone: Stabilization effect of antioxidants
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Avobenzone is one of the most common UVA-filters in sunscreens, and is known to be photounstable. Some of the strategies used to stabilize this filter present some drawbacks like photosensitization reactions. Antioxidants are widely used as cosmetic ingredients that prevent photoageing and complement the photoprotection offered by the UV-filters preventing or reducing photogenerated reactive species. The purpose of this work was to study the effect of antioxidants in the photostabilization of avobenzone. The filter dissolved in dimethyl sulfoxide or incorporated in a sunscreen formulation was irradiated with simulated solar radiation (750 W/m2). The tested antioxidants were vitamin C, vitamin E, and ubiquinone. The area under the curve of the absorption spectrum for UVA range and the sun protection factor (SPF) were calculated. Vitamin E (1:2), vitamin C (1:0.5) and ubiquinone (1:0.5) were the more effective concentrations increasing the photostability of avobenzone. In sunscreen formulations, the most effective photostabilizer was ubiquinone which also promoted an increase in SPF. This knowledge is important to improve effectiveness of sunscreen formulation. Antioxidants can be valuable ingredients for sunscreens with a triple activity of filter stabilization, SPF boosting and photoageing prevention.
- Afonso,Horita,Sousa E Silva,Almeida,Amaral,Lob?o,Costa,Miranda, Margarida S.,Esteves Da Silva, Joaquim C.G.,Sousa Lobo
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- Methoxy-monobenzoylmethane protects human skin against uv-induced damage by conversion to avobenzone and radical scavenging
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Avobenzone, one of the most commonly used UV filters in topical sunscreens, is susceptible to photodegradation with a consequential reduction of its UV absorbing properties. This loss of function may lead to skin irritation, photodermatosis, and photoallergic reactions caused by photodegradation byproducts. In this work, we aim to address this issue with a substance named methoxy-monobenzoylmethane (MeO-MBM), which is neither a UVB nor a UVA filter, but which converts to avobenzone, a known and approved UVA filter, under mainly UVB light irradiation. The antioxidant and intracellular radical formation properties of MeO-MBM were compared to the ones of avobenzone. The UV irradiation of MeO-MBM led to an increase in UV absorption primarily in the UVA range after conversion, both in vitro and in vivo. HPTLC and UHPLC studies illustrate the conversion of MeO-MBM to avobenzone in vitro after irradiation at 250 kJ/m2, reaching a conversion rate of 48.8%. A stable molecular antioxidant activity was observed, since 100-μM MeOMBM was measured to be 11.2% in the DPPH assay, with a decrease to 9.7% after irradiation. In comparison, the molecular antioxidant activity of 100-μM avobenzone was determined to be 0.8%. In keratinocytes, MeO-MBM reduces the intracellular ROS by 90% and avobenzone by 75% with tBHP as the inducer and by 53% and 57%, respectively, when induced by pyocyanin, indicating the redox scavenging capacity of both these molecules. These results indicate that MeO-MBM functions initially as an antioxidant material and as a photoantioxidant during its conversion process to avobenzone. This research provides insight into the development of active ingredients for topical applications with dynamic functionalities. Using this approach, we demonstrate the possibility to extend the UV protection offered to skin cells while combating cellular stress in parallel.
- Carola, Christophe,Keck, Cornelia M.,Salazar, Andrew,Termer, Michael,von Hagen, Joerg
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- Novel Bifunctionalization of Activated Methylene: Base-Promoted Trifluoromethylthiolation of β-Diketones with Trifluoromethanesulfinyl Chloride
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A novel bifunctionalization of activated methylene was achieved successfully through the base-promoted trifluoromethylthiolation of β-diketones or β-ketoesters with trifluoromethanesulfinyl chloride. A series of α-trifluoromethylthiolated α-chloro-β-diketones and α-chloro-β-ketoesters were obtained in moderate to good yields under mild conditions. When β-diketones containing a phenyl group with a hydroxyl or amino substituent at the ortho position were used as substrates, intramolecular trifluoromethylthiolation/cyclization reaction took place to give the corresponding cyclic products. Furthermore, the protocol could be extended to perfluoroalkylthiolation with the sodium perfluoroalkanesulfinate/POCl3 system. On the basis of experimental results, plausible mechanisms are proposed.
- Sun, Dong-Wei,Jiang, Min,Liu, Jin-Tao
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supporting information
p. 10797 - 10802
(2019/07/03)
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- Synthesis method of avobenzone
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The invention relates to a synthesis method of avobenzone. The synthesis method uses concentrated sulfuric acid as an acid medium to provide a needed acidic condition for carboxyl esterification, theesterification reaction belongs to a relatively common reaction in organic synthesis reactions, the reaction operation is simple, the post-treatment is easy, and the purity of the obtained product does not need special purification, and the purity, yield and other aspects are ensured, so that the synthesis method is relatively suitable for industrialized large-scale production. Sodium amide with strong alkalinity is used as a basic reagent for the Claise condensation reaction, and the final product is crystallized from a dichloromethane solution by using petroleum ether with less polarity in the post-treatment of the reaction, so that the post-treatment operation of this step is greatly simplified, the purity of the obtained product is relatively high, and the yield is also greatly improved. Crystallization and recrystallization methods are basically adopted in the post-treatment of the reactions, so that the yield is improved, and the post-treatment is easy, so that a method for industrial production is provided.
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Paragraph 0016; 0017; 0020; 0021
(2019/07/10)
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- ONE-STEP, FAST, 18F-19F ISOTOPIC EXCHANGE RADIOLABELING OF DIFLUORO-DIOXABORININS AND USE OF SUCH COMPOUNDS IN TREATMENT
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A compound according to Formula (I) or a pharmaceutically acceptable salt and/or solvate thereof, wherein X1 and X2 are each independently 18F or 19F; R1 and R2 are each independently alkyl, amine, perfluoroalkyl, alkenyl, alkynyl, aryl, or aralkenyl; and R3 is H, halo, alkyl, alkyl ester, alkenyl, alkynyl, aryl, or aralkenyl; or wherein: R1 and R3 or R2 and R3 join to form a 6-membered cycloalkyl or heterocyclyl; or R1 and R3, R2 and R3, or R1, R2, and R3 join to form a substituted or unsubstituted polycyclic ring, wherein the polycyclic ring comprises fused cycloalkyl, heterocycloalkyl, aryl, or heteroaryl rings.
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Paragraph 0019; 0206-0207
(2019/12/15)
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- High-yield production process for 1,3-diphenyl propanedione compound
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The invention discloses a high-yield production process for a 1,3-diphenyl propanedione compound. The production process comprises the steps that a benzoate compound A, a catalyst and a solvent I areadded into a reaction kettle, then an acetophenone compound B is dropwise added into the reaction kettle at the set temperature for reaction, and after reaction, a final product is prepared through acidification, washing, desolvation and recrystallization. The production process has the characteristics that a mixed basic catalyst is adopted, compared with sodium methylate and a traditional process, the yield is increased by 10-15% and is greater than or equal to 85.0%, the production operation is easy, the environmental pollution is small, the product color is light, the distinctive aromatic odor is achieved, the quality is good, the market competitiveness is high, and the industrialization promotion is easy.
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Paragraph 0085-0114
(2019/02/19)
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- A process for preparing arab League Fu Benzong method
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The invention provides a method for preparing avobenzone. The method comprises the steps that p-tert-butylbenzaldehyde and p-methoxyacetophenone serve as raw materials, a condensation reaction is performed under the alkaline condition, and prepared condensation products are oxidized into the avobenzone under the action of an oxidizing agent. The preparation method is simple, convenient, easy to perform and few in reaction steps, the preparation condition is mild and easy to control, and the prepared avobenzone is light in color, good in quality, pure in smell, high in market competitiveness and capable of easily achieving industrialization popularization.
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Paragraph 0066; 0108; 0109; 0113; 0114; 0118-0119; 0123-0124
(2017/08/26)
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- A arab League Fu Benzong synthetic method
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The invention discloses a synthetic method of avobenzone. The avobenzone is prepared by subjecting phenetole and methylbenzene, as starting materials, to alkylation, oxidation, esterification, acylation and condensation reaction. During oxidation, the oxidant potassium permanganate is added to a reaction system six times, thus thermal decomposition and deacidification of the potassium permanganate is avoided, and reaction yield is higher. During esterification, with methylsulphonic acid as catalyst, P-tert-butyl benzoic acid and methanol are subjected to reflux reaction for 8 hours according to a molar ratio: 1:7; the methanol is added in two stages for reaction, and the problem that water diversion fails in the reaction process is solved. During acylation, phosphotungstic acid is used as catalyst, reaction selectivity is improved, post-reaction treatment is simpler, and reaction yield is higher; the phosphotungstic acid is recyclable, thus cost is saved and industrial production is more benefited.
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- Variations in the blaise reaction: Conceptually new synthesis of 3-amino enones and 1,3-diketones
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Organic compounds with 3-amino enone or 1,3-diketone functional groups are extremely important, as they can be converted into a plethora of heterocyclic or carbocyclic compounds, or can be used as ligands in metal complexes. We have achieved a new, easy, straightforward and convenient synthesis of 3-amino enones and 1,3-diketones starting from aryl/heteroaryl/alkyl nitriles and 1-aryl/alkyl 2-bromoethanones. The reaction is a variation of the classical Blaise reaction, and it works with zinc and trimethylsilyl chloride as an activator. By running the hydrolysis of the reaction intermediate with HCl (3 N aq.) at 0-30 °C or at 100 °C, it is possible to form either 3-amino enones or 1,3-diketones, respectively. The newly developed method was used for the synthesis of avobenzone, an ingredient of sun-screen lotions. Furthermore, an easy synthesis of (Z)-3-amino-1-[4-(tertbutyl) phenyl]-3-(4-methoxyphenyl)prop-2-en-1-one, with UV/Vis absorption characteristics similar to those of avobenzone, was also achieved.
- Rao, H. Surya Prakash,Muthanna, Nandurka
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supporting information
p. 1525 - 1532
(2015/03/04)
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- Cosmetic compositions
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Suggested is a cosmetic compositions comprising (a) a crosspolymer obtained from copolymerisation of at least two different polyols and at least one dicarboxylic acid and (b) at least one fragrance.
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- A composition for lightening skin and hair
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Suggested is a composition comprising (a) sclareolide and (b1) at least one tyrosinase inhibitor; and/or (b2) at least one sun protection factor; and/or (b3) at least one anti-oxidants; and/or (b4) at least one anti-inflammatory agent; and/or (b5) at least one desquamating agent.
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- Quantitative evaluation of thermodynamic parameters for thermal back-reaction after mechanically induced fluorescence change
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Kinetics of the thermal back-reaction of β-diketonate boron difluoride complexes after mechanical perturbation were evaluated by fluorescence intensity changes for the first time, suggesting that the activation parameters of the reaction intermediates gov
- Ito, Fuyuki,Sagawa, Takehiro
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p. 19785 - 19788
(2013/11/06)
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- TRIAZINES AS REACTION ACCELERATORS
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The invention relates to the use of at least one specific triazine or melamine and/or salt thereof as accelerator for a photoinduced reaction of 3-(4-tert-butylphenyl)-3-hydroxy-1-(4-methoxyphenyl)-propan-1-one, 1-(4-tert-butylphenyl)-3-hydroxy-3-(4-methoxyphenyl)-propan-1-one or a mixture of these compounds to give avobenzone. The invention furthermore relates to a composition comprising at least one specific triazine or melamine and to a method for the stabilisation of the UV absorption capacity of a composition by means of a mixture of at least one specific triazine or melamine together with 3-(4-tert-butylphenyl)-3-hydroxy-1-(4-methoxyphenyl)propan-1-one, 1-(4-tert-butylphenyl)-3-hydroxy-3-(4-methoxyphenyl)propan-1-one or a mixture of these compounds, particularly preferably together with 3-(4-tert-butylphenyl)-3-hydroxy-1-(4-methoxyphenyl)propan-1-one.
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Paragraph 0194
(2013/03/26)
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- Preparation and structures of some new 1H-pyrazole derivatives
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Some new 3,5-diaryl-1H-pyrazoles were prepared from aryl methyl ketones via Claisen condensation with aromatic esters and followed by cyclization with hydrazine monohydrate. Their structures were confirmed by IR, 1H NMR spectroscopy, mass spect
- Wang, Dun-Jia,Kang, Yan-Fang,Zheng, Chun-Yang,Wei, Xian-Hong
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p. 2311 - 2320
(2013/07/26)
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- PROCESS FOR THE MANUFACTURE OF DIBENZOYLMETHANE DERIVATIVES
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The invention relates to a process for the manufacture of substituted dibenzoylmethane derivatives. This economical process provides products in high purity and yields and results in shorter reaction times.
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Page/Page column 10-11
(2012/07/13)
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- COSMETIC COMPOSITIONS COMPRISING AN ESTER DERIVED FROM 4-CARBOXY-2-PYRROLIDINONE AND A MEROCYANIN SCREENING AGENT; USE OF SAID DERIVATIVE AS A SOLVENT FOR A MEROCYANIN SCREENING AGENT
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The present invention relates to a composition comprising, in a cosmetically acceptable medium, at least one ester derived from 4-carboxy-2-pyrrolidinone, of formula (I) below: in which: R1 denotes a linear or branched C1-C20 alkyl radical,R2 denotes a linear or branched C1-C20 alkyl radical that may contain a C5-C6 ring, the phenyl radical, the benzyl radical or the phenethyl radical,and at least one merocyanin-type UV screening agent. The present invention also relates to the use of at least one ester derived from 4-carboxy-2-pyrrolidinone, of formula (I), as defined above, in a composition comprising, in a cosmetically acceptable medium, at least one merocyanin-type UV screening agent, as a solvent for said merocyanin screening agent, in and/or as an agent for improving the solubility of said merocyanin screening agent in said composition or with the aim of improving the sun protection factor.
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- COSMETIC COMPOSITIONS COMPRISING AN ESTER DERIVED FROM 4-CARBOXY-2-PYRROLIDINONE AND A LIPOPHILIC SCREENING AGENT; USE OF SAID DERIVATIVE AS A SOLVENT FOR A BENZOPHENONE LIPOPHILIC SCREENING AGENT
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The present invention relates to a composition comprising, in a cosmetically acceptable medium, at least one ester derived from 4-carboxy-2-pyrrolidinone, of formula (I) below: in which: R1 denotes a linear or branched C1-C20 alkyl radical,R2 denotes a linear or branched C1-C20 alkyl radical that may contain a C5-C6 ring, the phenyl radical, the benzyl radical or the phenethyl radical,and at least one benzophenone-type lipophilic UV screening agent. The present invention also relates to the use of at least one ester derived from 4-carboxy-2-pyrrolidinone, of formula (I), as defined above, in a composition comprising, in a cosmetically acceptable medium, at least one benzophenone-type lipophilic UV screening agent, as a solvent for said benzophenone screening agent, in and/or as an agent for improving the solubility of said benzophenone screening agent in said composition or with the aim of improving the sun protection factor.
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- COSMETIC TREATMENT METHOD USING A COMPOUND THAT CAN BE CONDENSED IN SITU AND A UV-RADIATION-FILTERING AGENT
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The present invention relates to a method for the cosmetic treatment of the skin, comprising the application, to the skin: of a compound or group of compounds A capable of condensing in situ and exhibiting at least one reactive functional group FA which is free after condensation; and of a screening agent C which screens out UV radiation, comprising a reactive functional group FC capable of forming a covalent bond or a physical (ionic, hydrogen) bond by reaction with the functional group FA.
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- Steady-state and laser flash photolysis studies on photochemical formation of 4-tert-butyl-4′-methoxydibenzoylmethane from its derivative via the Norrish Type II reaction in solution
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A photochemical formation process of avobenzone (AB; 4-tert-butyl-4′-methoxydibenzoylmethane) from 1,1-(4-tert-butybenzoyl)(4′-methoxybenzoyl)butane (PrAB) is studied by steady-state and laser flash photolysis in solution. The quantum yield of the formation via the triplet state of PrAB is determined to be 0.23 in degassed acetonitrile at 295K. The Arrhenius plots of the decay rate of triplet PrAB show that photoelimination proceeds with an activation energy of 6.0kcalmol-1 and the frequency factor of 4.6×1010s-1.
- Yamaji, Minoru,Paris, Cecilia,Miranda, Miguel ángel
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experimental part
p. 153 - 157
(2010/10/20)
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- Photoprotective compositions comprising photosensitive 1,3,5-triazine compounds, dibenzoylmethane compounds and siliceous s-triazines substituted with two aminobenzoate or aminobenzamide groups
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UV-photoprotective, topically applicable cosmetic/dermatological compositions contain: (a) at least one dibenzoylmethane compound,(b) at least one 1,3,5-triazine compound that is photosensitive in the presence of a dibenzoylmethane compound, and(c) at least one siliceous s-triazine compound substituted with two aminobenzoate or aminobenzamide groups, or a tautomeric form thereof, the 1,3,5-triazine compounds being improvedly photostable in such compositions.
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- Cosmetic/sunscreen compositions containing dibenzoylmethane compounds and dithiolane compound photostabilizers therefor
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Cosmetic/sunscreen compositions contain a combination of at least one dibenzoylmethane sunscreen compound and a photostabilizing amount of at least one dithiolane compound of formula (I) below:
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- Cosmetic compositions comprising 4-carboxy-2-pyrrolidinone esters and triazine lipophilic UV-screening agents
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UV-screening compositions, formulated into a cosmetically acceptable medium, contain at least one ester solvent derived from 4-carboxy-2-pyrrolidinone, of formula (I) below: in which: R1 is a linear or branched C1-C20 alkyl radical,R2 is a linear or branched C1-C20 alkyl radical that may contain a C5-C6 ring member, the phenyl radical, the benzyl radical or the phenethyl radical, and at least one triazine-type lipophilic UV-screening agent.
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- AHR MEDIATORS
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The invention relates to a method for finding and assessing agonists [and] antagonists of the aryl hydrocarbon receptor (Ah receptor; AhR), to the agonists and antagonists themselves and to uses thereof
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- Sun protection compositions comprising semi-crystalline polymers and hollow latex particles
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Topically applicable cosmetic/dermatological UV protection compositions having enhanced SPF contain at least one organic UV screening agent and/or at least one inorganic screening agent, such compositions also containing at least the following constituents (A) and (B): A) a semi-crystalline polymer which is solid at ambient temperature and has a melting point of greater than or equal to 30° C., containing a) a polymeric backbone and b) at least one crystallizable organic side chain and/or one crystallizable organic block forming part of the backbone of this said polymer, said polymer having a number-average molecular mass Mn of greater than or equal to 1,000, and B) hollow latex particles having a particle size ranging from 150 to 380 nm, formulated into a topically applicable, physiologically acceptable medium therefor.
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- COSMETIC OIL-IN-WATER EMULSION
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A cosmetic or dermatological compositions of oil-in-water emulsion type, including, in a physiologically acceptable medium, at least gemini surfactant of formula (I): in which R1 and R3 denote, independently of one another, 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 and Y denote, independently of one another, a group —(C2H4O)a—(C3H6O)bZ; n ranges from 1 to 10, in combination with an effective amount of at least one semi-crystalline polymer which is solid at ambient temperature and which has a melting point below 70° C., said polymer having a number-average molecular mass greater than or equal to 2000, said emulsion having a proportion of fatty phase of greater than 10% by weight relative to the total weight of the composition and including more than 40% by weight of non-volatile oil(s) relative to the weight of the fatty phase.
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- Photostable cosmetic compositions comprising dibenzoylmethane/pyrrolidinone compounds
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Photostable UV-photoprotecting cosmetic sunscreen compositions contain (a) an effective UV-photoprotecting amount of at least one dibenzoylmethane compound sunscreen, (b) an effective radiation-photostablizing amount of at least one pyrrolidinone compound having the formula (I) below: and, advantageously, at least one liquid fatty phase and at least one lipophilic active sunscreen agent of low solubility, formulated into (c) a cosmetically acceptable support therefor.
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- Photoprotective cosmetic compositions comprising photostabilized dibenzoylmethane compounds and siloxane-containing arylalkyl benzoate amide compounds
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Photostable, topically applicable cosmetic/dermatological compositions contain at least one dibenzoylmethane sunscreen compound and at least one photostabilizing siloxane-containing arylalkyl amide compound of formula (I) below:
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- Benzoic acid ester compounds, compositions, uses and methods related thereto
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Benzoic acid ester compounds of formula (I): wherein R and R1-R5 are as defined in the description, methods for producing them and use thereof in cosmetic, pharmaceutical, personal care and industrial preparations as sunscreens based on photochemical precursor properties of ultraviolet absorbers.
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Page/Page column 17; 35
(2010/11/23)
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- Process for the purification of 1,3-diketones
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A process for the purification of 1,3-diketones comprising reacting a 1,3-diketone with an earth metal or alkaline earth metal complexing agent in an organic solvent, isolating, washing and decomposing the resulting complex, and isolating the purified 1,3-diketone.
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- Photostable UV-screening compositions comprising dibenzoylmethane/diarylbutadiene compounds
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Topically applicable, photostable cosmetic/dermatological UV-screening compositions comprise (a) at least one photolabile UV-screening dibenzoylmethane compound and (b) a dibenzoylmethane photostabilizing amount of at least one 4,4-diarylbutadiene compound, formulated into a topically applicable, cosmetically/dermatologically acceptable support therefor; the weight ratio of the 4,4-diarylbutadiene compound(s) to the diarylbutadiene compound(s) is characteristically greater than 2.5 and the subject compositions are advantageously devoid of any cinnamate sunscreen.
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- Dibenzoylmethane sunscreen compositions photostabilized with amphiphilic block copolymers
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Topically applicable photostable sunscreen/photoprotective compositions contain at least one dibenzoylmethane UV-sunscreen and an effective photostabilizing amount therefor of at least one amphiphilic block copolymer which comprises at least one nonionic hydrophilic polymer block and at least one hydrophobic polymer block, formulated into a topically applicable, cosmetically acceptable medium therefor.
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- Phase inverted oil-in-water photoprotective emulsions comprising nanopigments of metal oxides and 4,4-diarylbutadiene UV-A sunscreens
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Stable UV-photoprotective, phase inverted oil-in-water emulsions, well suited for the photoprotection of the skin, lips and/or hair, the average size of the globules which constitute the oily phase thereof ranging from 100 nm to 1,000 nm, contain inorganic metal oxide nanopigments and at least one organic UV-screening agent, and which also contain at least one organic 4,4-diarylbutadiene UV-A-screening agent.
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- Water-in-oil photoprotective emulsions comprising polyolefinic surfactants and 4,4-diarylbutadiene UV-A sunscreens
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Stable UV-photoprotective water-in-oil emulsions, well suited for the photoprotection of the skin, lips and/or hair against the damaging effects of UV-radiation, contain at least one polymeric surfactant comprising at least one polar part and at least one polyolefinic apolar part, and also containing at least one organic 4,4-diarylbutadiene UV-A-screening agent.
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- Photoprotective UV-screening compositions comprising triazine/dibenzoylmethane/diarylbutadiene compounds
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Topically applicable, photostable cosmetic/dermatological UV-screening compositions suited for photoprotecting the skin and the hair, comprise (a) at least one UV-screening dibenzoylmethane compound, (b) at least one UV-screening 1,3,5-triazine compound that is photosensitive in the presence of a dibenzoylmethane compound, and (c) a 1,3,5-triazine photostabilizing amount of at least one 4,4-diarylbutadiene compound, formulated into a topically applicable, cosmetically/dermatologically acceptable support therefor; the weight ratio of the 4,4-diarylbutadiene compound(s) to the dibenzoylmethane compound(s) is characteristically greater than 2.5 and the subject compositions are advantageously devoid of any cinnamate sunscreen.
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- Photostable photoprotective UV-screening compositions comprising dibenzoylmethane/methyl-benzylidenecamphor/diarylbutadiene compounds
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Topically applicable, photostable cosmetic/dermatological UV-screening compositions comprise (a) at least one UV-screening dibenzoylmethane compound, (b) p-methylbenzylidenecamphor, and (c) a methylbenzylidenecamphor photostabilizing amount of at least one 4,4-diarylbutadiene compound, formulated into a topically applicable, cosmetically/dermatologically acceptable support therefor; the weight ratio of the 4,4-diarylbutadiene compound(s) to the dibenzoylmethane compound(s) is characteristically greater than 2.5 and the subject compositions are advantageously devoid of any cinnamate sunscreen.
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- Nonaerosol/aerosol dispensing of sunscreen sprays comprising silica microparticles
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Nonaerosol/atomizer pumps or aerosol dispensers comprise (A) a reservoir confining at least one vaporizable sunscreen composition suited for UV-photoprotecting the skin and/or hair against the damaging effects of UV radiation, the at least one vaporizable sunscreen composition comprising (1) a UV-photoprotecting amount of at least one UV-sunscreen and (2) an SPF-enhancing amount of generally spherical silica microparticles, formulated into (3) a topically applicable, cosmetically acceptable carrier therefor, and (B) at least one agent for pressurizing the at least one vaporizable sunscreen composition into a spray of fine sunscreen particles.
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- Aqueous photoprotective compositions comprising acrylamido-2-methylpropanesulfonic acid polymers and 4,4-diarylbutadiene UV-A sunscreens
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Photoprotective compositions, e.g., oil-in-water or water-in-oil emulsions, well suited for the photoprotection of the skin, lips and/or hair against the damaging effects of UV-radiation, comprise at least one aqueous phase, at least one oily phase, at least one partially or completely neutralized, crosslinked or non-crosslinked water-soluble or water-dispersible acrylamido-2-methylpropanesulfonic acid (AMPS) polymer and at least one UV radiation-screening system, said at least one screening system comprising at least one 4,4-diarylbutadiene UV-A-screening agent
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- Aqueous antisun/sunscreen compositions comprising amphiphilic 2-Acrylamidomethylpropanesulfonic acid polymers and water-soluble silicones
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Photoprotective compositions well suited for the photoprotection of the skin, lips and/or hair against the damaging effect of UV-radiation comprise at least one aqueous phase and at least one system for screening out UV-radiation, and which also contain: (a) at least one partially or totally neutralized, crosslinked or non-crosslinked amphiphilic polymer of 2-acrylamidomethylpropanesulfonic acid (AMPS), and (b) at least one water-soluble silicone comprising at least one terminal or pendent monovalent polyoxyalkylene group.
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- Finely divided photoprotective oil-in-water emulsions comprising 4,4-diarylbutadiene UV-A sunscreens
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UV-Photoprotective oil-in-water emulsions well suited for photoprotecting the skin, lips and/or hair against the damaging effects of UV-radiation, the oil globules of which having an average size of at most 500 nm and containing particles of at least one ionic polymer and at least one UV-radiation-screening system, such screening system comprising at least one 4,4-diarylbutadiene UV-A-screening agent.
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- Photostabilized dibenzoylmethane sunscreens immobilized within sol/gel matrices
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Photoprotective cosmetic/dermatological compositions well suited for the UV-photoprotection of the skin, hair, nails, eyebrows, eyelashes and/or lips, contain an effective photostable and UV-photoprotecting amount of at least one dibenzoylmethane organic sunscreen immobilized within a matrix prepared via sol-gel process from at least one silicon alkoxide, at least one non-ionic surfactant and water, but in the absence of any organic solvent, formulated into a topically applicable, cosmetically/dermatologically acceptable medium therefor.
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- Photochemical behavior of a new long-chain UV absorber derived from 4-tert-butyl-4′-methoxydibenzoylmethane
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A new UV filter, the 1-(4-tert-butylphenyl)-2-decanyl-3-(4′- methoxyphenyl)-propane-1,3-dione, called C10-DBM, was prepared by grafting a 10-carbon aliphatic chain to the α-carbonyl position of 4-tert-butyl-4′-methoxydibenzoylmethane (BM-DBM), a well-known and often used UV filter. The UV-A absorption efficiency of organic solutions containing the new filter was tested and compared with identical solutions containing BM-DBM with or without irradiation (xenon lamp). The originality of this new filter is that its UV-A absorbance appeared during irradiation of the molecule. Although the molar absorption coefficient of C01-DBM in the UV-A domain was lower than that of BM-DBM, the solutions absorption exhibited a much more photostable behavior under irradiation. In this study, we first demonstrated that C10-DBM was a precursor of BM-DBM (enol isomer) by means of high-performance liquid chromatography followed by mass spectrometry. Indeed, we showed that the UV-A absorption of C10-DBM solutions appearing during the irradiation of the molecule was due to a Norrish-II reaction (β-cleavage), which induced the release of the BM-DBM enol form and 1-decene. Then, we established a kinetic model for the photochemistry of C10-DBM and fitted the variation of UV absorption spectra to confirm the proposed mechanism.
- Wetz, Fabienne,Routaboul, Corinne,Lavabre, Dominique,Garrigues, Jean-Christophe,Rico-Lattes, Isabelle,Pernet, Ingrid,Denis, Alain
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p. 316 - 321
(2007/10/03)
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- SYNERGISTICALLY UV-PHOTOPROTECTING MIXED SUNSCREEN COMPOSITIONS
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Topically applicable cosmetic/dermatological sunscreen composition well suited for the enhanced UV-photoprotection of human skin and/or hair, contain synergistically UV-APPD-enhancing amounts of (i) at least one UV-screening silicon compound having a benzotriazole functional group substituent, (ii) at least one UV-screening dibenzoylmethane compound, and (iii) at least one UV-screening amino-substituted 2-hydroxybenzophenone compound having the following structural formula (III): formulated into (iv) a topically applicable, cosmetically/dermatologically acceptable vehicle, diluent or carrier therefor.
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- UV-photostabilized sunscreen compositions comprising dibenzoylmethane/triazine/benzophenone compounds
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Topically applicable cosmetic/dermatological sunscreen compositions well suited for the stable UV-photoprotection of human skin and/or hair, are devoid of any p-methylbenzylidenecamphor, but which contain (a) an effective photoprotecting amount of at least one UV-sunscreening dibenzoylmethane compound, (b) an effective photoprotecting amount of at least one UV-screening 1,3,5-triazine compound normally photosensitive in the presence of a dibenzoylmethane compound (a), and (c) an effective photostabilizing amount of at least one UV-screening amino-substituted 2-hydrozybenzophenone compound having the following structural formula (VIII): formulated into (d) a topically applicable, cosmetically/dermatologically acceptable vehicle, diluent or carrier therefor.
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- Composition containing a dibenzoylmethane derivative and an alpha-alkylstyrene dimer uv stabilising method
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The invention relates to a cosmetic or dermatological composition, for topical use, in particular for the photoprotection of skin and hair, characterized in that it comprises at least, in a cosmetically acceptable support: (a) from 0.1 to 20% by weight of a UV screening agent of the dibenzoylmethane-based type and (b) from 0.1 to 20% by weight of one specific alpha-alkylstyrene-based dimer. The invention relates to a novel process for improving the stability of at least one dibenzoylmethane derivative towards UV radiation, which consists in combining with the said dibenzoylmethane derivative an effective amount of at least one specific alpha-alkylstyrene-based dimer.
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- Synergistically UV-photoprotecting sunscreen compositions comprising camphorsulfonic acid/benzophenone compounds
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Topically applicable cosmetic/dermatological sunscreen compositions well suited for the enhanced UV-photoprotection of human skin and/or hair, contain synergistically SPF-enhancing amounts of (a) benzene-1,4-di(3-methylidene-10-camphorsulfonic acid), optionally in partially or completely neutralized state, and (b) at least one amino-substituted 2-hydroxybenzophenone compound having the following structural formula (I): formulated into (c) a topically applicable, cosmetically/dermatologically acceptable vehicle, diluent or carrier therefor.
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- UV-photostabilized sunscreen compositions comprising dibenzoylmethane/benzophenone compounds
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Topically applicable cosmetic/dermatological sunscreen compositions well suited for the stable UV-photoprotection of human skin and/or hair are devoid of any p-methylbenzylidenecamphor, but contain (a) an effective photoprotecting amount of at least one UV-screening dibenzoylmethane compound, and (b) an effective photostabilizing amount of at least on UV-screening amino-substituted 2-hydroxybenzophenone compound having the following structural formula (I): 1formulated into (c) a topically applicable, cosmetically/dermatologically acceptable vehicle, diluent or carrier therefor.
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- Self-tanning composition containing an N-acyl amino acid ester and a self-tanning agent
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The invention relates to cosmetic and/or dermatological compositions more particularly intended for artificially tanning and/or browning the skin, comprising, in a cosmetically acceptable support, at least one self-tanning agent and at least one N-acyl amino acid ester. The invention also relates to a cosmetic treatment process for artificially tanning and/or browning the skin, characterized in that it consists in applying to the skin an effective amount of a composition according to the invention. The invention also relates to the use of an N-acyl amino acid ester with the aim of improving the coloration and/or stability of a self-tanning agent in a composition for artificially tanning and/or browning the skin.
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- STABLE/IMPROVEDLY SELF-TANNING COMPOSITIONS COMPRISING AMINO-SUBSTITUTED 2-HYDROXYBENZOPHENONE COMPOUNDS
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Topically applicable cosmetic/dermatological self-tanning compositions well suited for enhancing the coloration imparted by and/or the stabilizing of the self-tanning agent, contain (i) an effective amount of at least one artificial/sunless tanning agent, and (ii) an effective stabilizing/enhancedly self-tanning amount of at least one amino-substituted 2-hydroxybenzophenone compound having the following structural formula (I): formulated into (iii) a topically applicable, cosmetically/dermatologically acceptable vehicle, diluent or carrier therefor.
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- Dibenzoylmethane sunscreen compositions containing photostablizing amounts of tri-substituted butane compounds
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Improvedly photostable UV-photoprotecting cosmetic/dermatological compositions for the skin and/or the hair contain (a) a UV-photoprotective amount of at least one dibenzoylmethane sunscreen, e.g., 4-(tert-butyl)-4′-methoxydibenzoylmethane or 4-isopropyldibenzoylmethane, advantageously (a′) a UV-photoprotective amount of at least one 1,3,5-triazine sunscreen, e.g., 2-[(p-(tert-butylamido]-4,6-bis[(p-(2′ethylhexyl-1′-oxycarbonyl)anilino]-1,3,5-triazine or 2,4,6-tris[p-(2′-ethylhexyl-1′-oxycarbonyl)anilino]-1,3,5-triazine, (b) an effective sunscreen photostabilizing amount of 1,1,1-tris(2-methyl-4-hydroxy-5-tert-butylphenyl) butane, formulated into (c) a topically applicable, cosmetically acceptable vehicle, diluent or carrier therefor.
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