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(12) Patent Application Publication (10) Pub US 20140335138A1 (19) United States (12) Patent Application Publication (10) Pub. N0.: US 2014/0335138 A1 Goldstein et al. (43) Pub. Date: NOV. 13, 2014 (54) MICROCAPSULES COMPRISING BLACK Publication Classi?cation PIGMENTS (51) Int. Cl. (76) Inventors: Danny Goldstein, KibbutZ Dafna (IL); A61K 8/11 (2006.01) Yuri Yasman, Carmiel (IL); Olga A61Q 1/10 (2006.01) B01J13/12 (2006.01) Privalova, KibbutZ LeHavot HaBashan A61K 8/81 (2006.01) (IL); Lior Benaltabet, KibbutZ Dafna C09C1/56 (2006.01) (1L) C09C1/24 (2006.01) (52) US. Cl. (21) Appl. No.: 14/118,266 CPC A61K8/11 (2013.01); C09C 1/56 (2013.01); C09C1/24 (2013.01); B01J13/12 (2013.01); (22) PCT Filed: May 16, 2012 A61K8/8152 (2013.01); A61Q 1/10 (2013.01); A61K 2008/115 (2013.01); A61K 2800/65] PCT No.: PCT/IL2012/000192 (2013.01); A61K 2800/624 (2013.01); A61K (86) 2800/43 (2013.01); C01P 2004/61 (2013.01) § 371 (0X1)’ USPC ......... .. 424/401; 524/560; 524/555; 524/431; (2), (4) Date: Nov. 18, 2013 524/306; 524/521; 523/336; 523/322 (57) ABSTRACT Monolayered microcapsules comprising a black pigment and Related US. Application Data cosmetic formulations comprising them are provided for use (60) Provisional application No. 61/486,413, ?led on May particularly in mascara and eye liner formulations. The black 16, 201 1. pigment may be carbon black, black iron oxide, or both. Patent Application Publication Nov. 13, 2014 Sheet 1 0f 4 US 2014/0335138 A1 il‘ig. m “iii” ‘30;quwag 42>C?)m 3i m i m 1 i w ms was; 3005: 9arfic§e 33% {pm} Patent Application Publication Nov. 13, 2014 Sheet 2 0f 4 US 2014/0335138 A1 Patent Application Publication Nov. 13, 2014 Sheet 3 0f 4 US 2014/0335138 A1 Patent Application Publication Nov. 13, 2014 Sheet 4 0f 4 US 2014/0335138 A1 US 2014/0335138 A1 Nov. 13, 2014 MICROCAPSULES COMPRISING BLACK resulting in more area to wet and thus requiring more energy PIGMENTS than a carbon black particle having lower surface area. Addi tionally, as the carbon black aggregate becomes smaller there FIELD OF THE INVENTION is a higher volume concentration of carbon black at the same weight loading (compared to particles having larger aggre [0001] The present invention relates to microcapsules com prising black pigments and to topical compositions compris gates) resulting in smaller inter-aggregate distances and, con sequently, greater attractive forces to overcome. ing them, particularly for use in cosmetics, more particularly for use in mascara and eye liner formulations. [0009] It would be bene?cial to provide carbon black in an encapsulated form that would increase the safety of use, avoid BACKGROUND OF THE INVENTION dustiness during manufacturing of the composition, and improve dispersion of carbon black in the composition and [0002] The most popular black pigments in cosmetic prod will not be considered as a nanomaterial (1 -100 nanometer). ucts nowadays are carbon black and iron oxide black. Black [0010] US. Pat. No. 5,286,291 discloses pigments contain iron oxide pigment, also known as ferrous ferric oxide ing carbon black and having improved abrasion resistance. (Fe3O4), consists of particles with diameters between about 1 WO 2010/085689 discloses antimicrobial carbon black dis and 100 nanometers. It has no known health hazards and is persions. US. Pat. No. 7,300,512 discloses a method ofmak considered non-toxic. It is more opaque and less toxic than ing pigment dispersion containing a carrier such as castor oil other black pigments. or vegetable wax, wherein the pigment is optionally black [0003] Carbon black pigment is produced by the incom iron oxide. plete combustion of hydrocarbon gas or oil. It is an ultra black [0011] US. Pat. No. 6,932,984 andU.S. Pat. No. 7,838,037 pigment, providing the most authentic black shades available. assigned to the same applicant of the present application The bene?ts of carbon black for use in cosmetics and particu disclose a method for microencapsulation of substances by larly in mascaras include less clumping, less beading, less the solvent removal method using non-chlorinated solvents. buildup, better lash separation and better lash curling. Since The method is based on physical processes only which do not carbon black is lighter with more color effect at low use cause any change of original physical and/ or chemical prop concentrations, ?nal formulations offer maximum cosmetic erties, biological activity, and safety of raw materials during performance without caking and buildup. the process. This method affords physical stability of the [0004] However, carbon black has not been permitted for microcapsules, high ability to entrap the active agents, pro cosmetic use in the US. from 1976 to 2004. In 2004 the US. tection of the active agents inside the microcapsules, and Food and Drug Administration (FDA) approved the use in prevention of the diffusion of the microencapsulated active cosmetics of one form of carbon black: high purity furnace agents to the external water phase in a water-based prepara black (one of the ?ve types of carbon black which have been tion. In US. Pat. No. 7,838,037 the resulting microcapsules produced). The FDA named the allowed colorant D&C Black are double layer and triple layer microcapsules. WO 2009/ #2 to emphasize that the material is subject to batch certi? 138978 of the same applicant discloses cosmetic composi cation. tions comprising double layer microcapsules which contain [0005] In addition, carbon black is very dif?cult to handle black iron oxide with additional iron oxides. during the process of manufacturing formulations. It consists of ?ne amorphous particles having an average primary par BRIEF DESCRIPTION OF THE FIGURES ticle size as small as 0.05 to 0.5 pm. Due to the ?ne primary [0012] FIGS. 1A-1B show particle size distribution of car particle size, carbon black particles tend to heavily aggregate bon black microcapsules having an average particle size of 40 and can be dif?cult to disperse uniformly in vehicles or resin pm or 1-2 pm, respectively. compositions. In addition, carbon black particles have a very [0013] FIGS. 2A-2C show scanning electron microscope low bulk density (about 0.1 g/cm3) and, accordingly, can easily become airborne and contaminate the working envi (SEM) images of non-encapsulated carbon black (raw mate rial, 2A); carbon black microcapsules having an average par ronment. ticle size of 40 pm in magni?cation x1000 (2B), and carbon [0006] Pigments, especially carbon black, present prob black microcapsules having an average particle size of 1 -2 pm lems to customers trying to handle and disperse these prod in magni?cation of x5000 (2C). ucts. Customers desire to have a product which is dust free, [0014] FIG. 3 shows SEM image of black iron oxide micro can be easily handled in conventional material transferring capsules in magni?cation x1000. equipment and have the same product in a form that will easily disperse in the host formulation. Additionally, carbon DETAILED DESCRIPTION OF THE INVENTION black lacks signi?cant surface functional groups, which means that the particles are hard to wet and therefore dif?cult [0015] Among conventional black pigments, carbon black to disperse. exhibits excellent blackness. Carbon black powder consists [0007] Achieving an adequate dispersion involves impart of ?ne amorphous particles exhibiting average particle size as ing enough energy in the system to overcome attractive forces small as 0.05 to 0.5 pm. Special color effects can be achieved between particles without putting much energy in the system by incorporation of carbon black into pigments. Carbon black that can destroy or change the desired properties of the for (D&C Black #2) is approved by FDA for use in eyeliner, mulation. Achieving dispersions of particulate matter, and in mascara, eye shadow, lipstick, blush, make up and founda particular carbon black dispersions, remains the domain of tion. experience and know how. [0016] In order to get full color tone out of carbon black it [0008] The primary particle size of a carbon black particle is of paramount importance that a good dispersion is made. determines, to a large extent, its degree of dispersability. The However, it is very dif?cult to disperse carbon black uni smaller the primary particle the higher the surface area, formly in formulations. Carbon black particle size is directly US 2014/0335138 A1 Nov. 13, 2014 related to the surface area of the pigment and in?uences its spherical homogeneous granules of the active substance dis color, rheology, dispersion and electrical conductivity in the persed in a polymer and are, in strict sense, spherically empty formulation. Carbon black particles tend to heavily aggre particles. gate. It can easily become airborne and contaminate work [0023] The term “wall-forming polymer” refers to a poly environments (bulk density of 0.1 g/cm3). mer or a combination of two or more different polymers as [0017] The present invention provides monolayered micro de?ned herein, which form a component of the external wall capsules comprising a core of a black pigment and a shell of or layer or shell of the microcapsules. The term “polymer a wall-forming polymeric material selected from a polyacry shell” refers to a polymer layer containing the wall-forming late, a polymethacrylate, a cellulose ether, a cellulose ester, or polymer(s). a combination thereof, wherein the microcap sules do not [0024] The dimensions and values disclosed herein are not contain a plasticizer (the plasticizer would cause softening of to be understood as being strictly limited to the exact numeri the wall-forming polymers). cal values recited. lnstead, unless otherwise speci?ed, each [0018] According to certain embodiments, the black pig such dimension is intended to mean both the recited value and ment is carbon black.
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