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(12) Patent Application Publication (10) Pub. No.: US 2017/0071865 A1 GOLDSTEN Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2017/0071865 A1 GOLDSTEN Et Al US 2017007 1865A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2017/0071865 A1 GOLDSTEN et al. (43) Pub. Date: Mar. 16, 2017 (54) ACTIVE AGENTCONTAINING Related U.S. Application Data MCROCAPSULES (60) Provisional application No. 61/947,683, filed on Mar. 4, 2014. (71) Applicant: Tagra Biotechnologies Ltd., Natania (IL) Publication Classification (51) Int. Cl. (72) Inventors: Danny GOLDSTEIN, Kibbutz Dafna A 6LX 9/50 (2006.01) (IL): Olga PRIVALOVA, Kibbutz (52) U.S. Cl. LeHavot HaBashan (IL); Lior CPC .................................. A61K 9/5078 (2013.01) BEN-ALTABET, Kibbutz Dafna (IL); Yaniv MENACHEM, Moshav Dishon (57) ABSTRACT (IL); Hanan HAJ, Rehaniya (IL); Multi-layer microcapsules comprising a core comprising Shaher DUCHI, Kfar Rama (IL) one or more active agents and two or more shells comprised of a wall-forming polymeric material, an opaque Substance (21) Appl. No.: 15/123,639 and a fatty acid salt, which are rupturable upon rubbing or pressing on the skin, are disclosed. The microcapsules are (22) PCT Fed: Mar. 4, 2015 characterized by improved lightness values (L*) and/or compatibility in aqueous Solution-containing formulations. (86) PCT No.: PCT/L2O15/05O236 Cosmetic or cosmeceutic formulations comprising the microcapsules, which can be, for example, body skin care S 371 (c)(1), formulation or facial skin care formulations, are also pro (2) Date: Sep. 4, 2016 vided. Patent Application Publication Mar. 16, 2017. Sheet 1 of 7 US 2017/0071865 A1 Patent Application Publication Mar. 16, 2017. Sheet 2 of 7 US 2017/0071865 A1 s Patent Application Publication Mar. 16, 2017. Sheet 3 of 7 US 2017/0071865 A1 s & ? s taa: . w { ex it: s g tee f 3. t 5 "is s s s e x ga . 5 s g 3. e 8 r Patent Application Publication Mar. 16, 2017. Sheet 4 of 7 US 2017/0071865 A1 Patent Application Publication Mar. 16, 2017. Sheet 5 of 7 US 2017/0071865 A1 s 3. 3 s » Patent Application Publication Mar. 16, 2017. Sheet 6 of 7 US 2017/0071865 A1 s 3 3 s d o co Co. r. ca. re Patent Application Publication Mar. 16, 2017. Sheet 7 of 7 US 2017/0071865 A1 MO||9),deO226el 09||001-009+009+---+---+---+---+------?;?,ogg · US 2017/007 1865 A1 Mar. 16, 2017 ACTIVE AGENTCONTAINING their capsules and become apparent when applied to the skin MCROCAPSULES through breaking of the capsules by pressure exerted during application of the composition to the skin. FIELD AND BACKGROUND OF THE 0008 WO 2004/075679 discloses rigid, non-rupturable INVENTION microcapsules containing a blend of at least two coloring 0001. The present invention, in some embodiments agents and compositions comprising them, which do not thereof, relates to encapsulation and, more particularly, but change their color upon application onto the skin. The not exclusively, to newly designed microcapsules, encapsu microcapsules are non-rupturable due to the use of cross lating active agents such as pharmaceutically, dermatology, linked polymeric matrix comprising polymers that have a and/or cosmetically active agents, and to compositions and/ glass transition temperature (Tg) higher than 80° C. or formulations such as, for example, cosmetic formulations 0009 U.S. Pat. No. 6,932,984, by the present assignee, and other topical formulations, containing same. discloses single- and double-layer microcapsules and a 0002 Compositions for topical applications comprising method for microencapsulation of Substances by the solvent various colorants or other active substances are known in the removal method using non-chlorinated solvents. The art. Previous attempts to use protected colorants in dermal method is based on physical processes which do not cause applications were mostly focused towards hydrophobic or any change of original physical and/or chemical properties, Solid decorative cosmetics such as make-up, lipstick, blush, biological activity, and safety of raw materials during the and powder products. process. 0003 U.S. Pat. Nos. 5,320,835 and 5,382,433 disclose (0010 U.S. Pat. No. 7,838,037, by the present assignee, “activatable' dormant colored particles or pigments and discloses double-layer and/or triple-layer microcapsules, cosmetic formulations comprising same and further com designed to rupture by a slight mechanical action Such as prising a colored base phase, and colorant entrapping Sub rubbing or pressing on the skin, and thereby immediately strate particles dispersed in said base phase. The encapsu release their encapsulated content. These microcapsules are lated colorants are said to be released into the base phase prepared by the solvent removal method using non-chlori when mechanical action is applied to the cosmetic formu nated solvents. This method affords physical stability to the lation, and produce an intense shade in the color of the base microcapsules, high ability to entrap the active agents, phase, whereas the colorant entrapping Substrate particles protection of the active agents inside the microcapsules, and entrap the released colorants and produce a subtle shade in prevention of the diffusion of the microencapsulated active the color of the base phase. The encapsulated pigments are agents to the external water phase in a water-based prepa made by a coacervation method. ration. 0004 U.S. Pat. No. 5,380,485 discloses colored cosmetic (0011 WO 2009/138978, by the present assignee, dis compositions, comprising particulate fillers coated with closes cosmetic compositions for dermal/topical application polymer that is combined with colorants, and their applica comprising double-layer, rupturable microcapsules which tion in decorative cosmetics. contain one or more microencapsulated colorants, and active 0005 U.S. patent application having Publication Nos. Substances. When applied to the skin, such compositions 2005/0031558 and 2005/0276774 disclose a personal care or produce an immediate color change effect indicating the cosmetic composition containing microparticles comprising delivery to the skin of the active substances contained in said a shatter resistant blend of distinct colorants microencapsu compositions. lated within a polymer matrix, preferably a cross-linked polymer matrix that does not allow any of the entrapped SUMMARY OF THE INVENTION colorant to be released even under prolonged use. The matrix polymer is preferably transparent or translucent Such 0012. In a cosmetic composition or formulation it is that the blend of encapsulated colorants provides the color highly desirable to retain an active Substance within capsules ing of the cosmetic product itself and of the skin upon before application thereof. There is also a need to protect application of the cosmetic composition. The microparticles encapsulated active Substances from potential detrimental disclosed in 2005/0276774 further contain secondary par effect caused by other Substances, particularly in a combined ticles (i.e. hydrophobic polymers different from those of the formulation that comprises active Substances in combination matrix polymer) that are distributed throughout the matrix. with colorants. 0006 U.S. Pat. No. 4,756,906 discloses decorative cos 0013 The effectiveness of protection or masking by metic compositions containing a first colorant and micro single-layer microencapsulation depends on the chemical capsules containing a solvated second colorant, different structure, molecular weight and physical properties of the from the first colorant. Upon rupture of the microcapsules, microencapsulated ingredient. For some active Substances, the coloration of the encapsulated pigment is added into the the known methods of single-layered microencapsulation do composition thereby altering its color characteristics. not provide an adequate protection from leaking and/or a 0007 U.S. Patent Application Publication No. 2008/ satisfying masking effect, and hence the use of single 81057 discloses compositions comprising at least one encap layered microcapsules may result in, for example, coloring Sulated pigment and at least one skin coloring agent chosen of the cosmetic composition before it is applied to the skin, from self-tanning agents and melanogenesis activators. The in case a colorant is encapsulated, or is leaching or decom composition develops a slow, long-term color after applica position of active agents before the composition is applied. tion to the skin due to the biological action of the self 0014 Currently known microcapsules not always pro tanning agents or the melanogenesis activators, while encap vide an adequate protection from leaking and/or a satisfying Sulated pigments provides immediate coloring of the skin. masking effect of the encapsulated agent. In addition, Such The pigments are said to be invisible in the composition by microcapsules often exhibit inferior stability in gel and other virtue of their encapsulation, but are readily released from water-based formulations. US 2017/007 1865 A1 Mar. 16, 2017 0015. In a search for microcapsules that would not be 0026. According to some of any of the embodiments limited by incompatibility with water-based formulations, described herein, the opaque Substance is TiO, and wherein and that would exhibit substantial stability in water-based an amount of TiO ranges from about 10% to about 80%, or formulations and an improved masking and/or protecting from about 30% to about 80%, or from about 30% to about effect and release of the encapsulated agent (e.g., colorant or 60%, by weight, of a total weight of the microcapsule. an active agent as described herein), the present inventors 0027. According to some of any
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