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(12) Patent Application Publication (10) Pub. No.: US 2016/0008237 A1 GOLDSTEN Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2016/0008237 A1 GOLDSTEN Et Al US 201600O8237A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2016/0008237 A1 GOLDSTEN et al. (43) Pub. Date: Jan. 14, 2016 (54) MICROCAPSULES COMPRISING Publication Classification SUNSCREEN AGENTS (51) Int. Cl. (71) Applicant: TAGRA BIOTECHNOLOGIES LTD., A618/II (2006.01) Natania (IL) A618/8 (2006.01) A618/35 (2006.01) (72) Inventors: Danny GOLDSTEIN, Kibbutz Dafna A61O 1704 (2006.01) (IL): Olga PRIVALOVA, Kibbutz A618/29 (2006.01) LeHavot HaBashan (IL); Lior (52) U.S. Cl. BEN-ALTABET, Kibbutz Dafna (IL); CPC. A61K 8/11 (2013.01); A61O 1704 (2013.01); Yaniv MENACHEM, Moshav Dishon A61K 8/29 (2013.01); A61K 8/35 (2013.01); (IL); Hanan HAJ, Rehaniya (IL) A61K 8/8152 (2013.01); A61K 2800/262 (2013.01); A61K 2800/412 (2013.01); A61 K (21) Appl. No.: 14/770,873 2800/52 (2013.01); A61 K 2800/30 (2013.01); (22) PCT Filed: Feb. 27, 2014 A6 IK 2800/805 (2013.01) (86). PCT No.: PCT/L2014/05O2O7 (57) ABSTRACT Microcapsules comprised of a core comprising one or more S371 (c)(1), Sunscreen agents and a shell of a wall-forming polymeric (2) Date: Aug. 27, 2015 material, which are non-rupturable upon rubbing or pressing Related U.S. ApplicationO O Data Topicalon the skin, RNR and processes of preparingR first same are disclosed.which (60) Provisional application No. 61/770,773, filed on Feb. can be, for example, Sunscreen formulations or skin care 28, 2013. formulations, are also provided. Patent Application Publication Jan. 14, 2016 Sheet 1 of 5 US 2016/0008237 A1 F.G. 1B Patent Application Publication Jan. 14, 2016 Sheet 2 of 5 US 2016/0008237 A1 S HW W mod 5. OOkW 5. Omm SE Patent Application Publication Jan. 14, 2016 Sheet 3 of 5 US 2016/0008237 A1 s Patent Application Publication Jan. 14, 2016 Sheet 4 of 5 US 2016/0008237 A1 US 2016/0008237 A1 Jan. 14, 2016 MCROCAPSULES COMPRISING major concerns regarding its systemic absorption profile has SUNSCREEN AGENTS engendered heated debates regarding the overall safety of this molecule. FIELD AND BACKGROUND OF THE 0005 AVobenzone, a dibenzoylmethane derivative (butyl INVENTION methoxydibenzoylmethane; trade names Parsol(R) 1789, 0001. The present invention, in some embodiments Eusolex(R, 9020, EscalolR 517 and others) is an oil soluble thereof, relates to microcapsules Suitable for use in topical ingredient used in Sunscreen products to absorb the full spec compositions and, more particularly, but not exclusively, to trum of UV-A rays. Its ability to absorb ultraviolet light over microcapsules comprising Sunscreen agents and to topical a wider range of UVA wavelengths than many organic Sun formulations comprising same, which can be used, for screen agents has led to its use in many commercial prepara example, in cosmetic formulations, such as Sunscreen and tions marketed as “broad spectrum Sunscreens. AVobenzone, skincare formulations. as a Sunscreen active, becomes photounstable and tends to 0002. The detrimental effects of UV exposure to the sun degrade chemically after prolonged exposure to ultraviolet have been well described in the literature. Both acute and radiation (UVR). Chemical degradation of avobenzone elimi chronic UV exposures can lead to Sunburn, photocarcinogen nates its ability to absorb UVR and hence to protect skin esis, photo-immunosuppression and photoaging. While the against damaging UV rays when it is used as a Sunscreen photoprotective benefits of the inorganic UV filters TiO, and active in Sunscreen products. ZnO have been known for decades, these earlier generations 0006. Some of the presently known sunscreen composi of inorganic filters, comprised of large particles, produce an tions contain more than one type of UV filter. Such compo opaque and white appearance on the skin. In addition to sitions are often characterized in that the UV filters tend to cosmetic drawbacks, widespread application of early formu interact, leading to a situation where the UV filter activity of lations containingTiO, or ZnO was further hindered by their one or more of the UV filters in the composition is reduced poor dispersive properties which resulted in grainy and occlu during storage or after being applied to the skin. sive qualities. Considerable effort has been made to overcome 0007 European Patent No. 1899015 discloses topical the cosmetic shortcomings of these inorganic UV filters by composition containing at least two different kinds of Sun progressively minimizing their particle size into the nano screen agents, wherein at least one kind of Sunscreen agent is range (less than 100 nm). encapsulated in microcapsules having an average, particle 0003 Nanoparticles are known to exhibit different chemi size of between 3 um to 8 Lum. Microcapsules smaller than 3 cal, mechanical, electrical and optical properties than stan um were sown to leak. The microcapsules are obtainable by dard-sized particles. Recently, it was reported, on the basis of an emulsion polymerization process or by a sol-gel process, in vitro cell experiments, that pure TiO, or ZnO nanoparticles wherein the encapsulating agent is a tetraalkoxysilane. Sol can induce free radical formation in the presence of light and gel microcapsules comprising Sunscreen agents are disclosed that this may damage applied therewith. Therefore, the incor in U.S. Pat. No. 6,303,149. These microcapsules were poration of TiO, and ZnO nanoparticles into Sunscreens has designed to permanently encapsulate the Sunscreen agents, raised interesting questions regarding the dermal penetration, but a significant amount of leakage of the Sunscreen agents systemic absorption and Subsequent toxicity of these nano through the microcapsules was observed when the microcap particles. Currently, there is no in vivo evidence to indicate Sules were incorporated into usual Sunscreen compositions, possible toxicity of nanoparticulate TiO, or ZnO in humans particularly when the microcapsules were of size Smaller than using Sunscreen products. To date, the current weight of evi 3 Jum. dence indicates that the particles remain on the surface of the 0008 Marcato et al., 2011 discloses polymeric and solid skin and in the outer dead layer (stratum corneum) of the skin. lipid nanoparticles as carriers of benzophenone-3 (BZ3), Thus, an analysis of the available evidence fails to demon aiming to improve the safety of Sunscreen products by strate toxicity of these products after cutaneous application to decreasing BZ3 skin penetration and decreasing BZ3 concen healthy, intact skin. Nevertheless, comprehensive and exten tration in Sunscreen formulation. BZ3 is encapsulated in poly sive studies are being sponsored by health authorities in dif (c-caprolactone) (PCL) nanoparticles by the nanoprecipita ferent countries to assess adverse effects of nanoparticles of tion method and in solid lipid nanoparticles (SLN) by the hot TiO or ZnO on the biological properties of cells and conse high pressure homogenization method. The particles were quent, negative health implications. stable for 40 days. After which time the encapsulated BZ3 0004 Oxybenzone (benzophenone-3) is a widely-used was released. lipophilic broad spectrum molecular Sunscreen agent that 0009 U.S. Pat. Nos. 6,932,984 and 7,838,037, by the effectively absorbs ultraviolet B (UVB: 290-320 nm), some present assignee, disclose a method for microencapsulation ultraviolet A (UVA; 320-360 nm) and some ultraviolet C of Substances by the solvent removal method using non (250-290 nm) light rays. However, oxybenzone is the most chlorinated solvents. The method is based on physical pro common cause of photoallergic contact dermatitis. Indeed, cesses which do not cause any change of original physical many Sunscreen molecules penetrate the skin causing photo and/or chemical properties, biological activity, and safety of allergies, phototoxic reactions and skin irritation (Marcato et raw materials during the process. This method affords physi al., 2011: "Nanostructured polymer and lipid carriers for cal stability of the microcapsules, high ability to entrap the sunscreen. Biological effects and skin permeation'. J. Nano active agents, protection of the active agents inside the micro science and Nanotechnology, Vol. 11, 1880-1886). In addi capsules, and prevention of the diffusion of the microencap tion, Systemic absorption of oxybenzone following its topical Sulated active agents to the external water phase in a water application on the skin has been reported (Burnett and Wang, based preparation. In U.S. Pat. No. 7,838,037 the resulting 2011: "Current sunscreen controversies: a critical review', microcapsules are double-layer and/or triple-layer microcap Photodermatology, Photoimmunology & Photomedicine, Sules, designed to rupture by a slight mechanical action Such vol. 27, pages 58-67). Aside from its photoallergic potential, as rubbing or pressing on the skin, and thereby immediately US 2016/0008237 A1 Jan. 14, 2016 release their encapsulated content. WO 2009/138978, by the 0022. According to some embodiments of the present present assignee, discloses cosmetic compositions, including invention, the microcapsule has a size within a range selected Sunscreen compositions, comprising double-layer, rupturable from about 1 um to about 100 um, from about 1 um to about microcapsules which contain one or more microencapsulated 90 um, from about 1 um to about 80 Lum, about 1 um to about colorants, inter alia, titanium oxide. WO 2009/138978 dis 70 um, 1 um about to about 60 um, about 1 um to about 50 um, closes a 45 SPF Sunscreen, color-changing composition com about 1 um to about 40 um, about 1 um to
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