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(12) Patent Application Publication (10) Pub. No.: US 2015/0064124 A1 YONTZ Et Al

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US 2015 0064124A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2015/0064124 A1 YONTZ et al. (43) Pub. Date: Mar. 5, 2015 (54) PERSONAL CARE FORMULATIONS A61O 9/04 (2006.01) CONTAINING ALKYL KETAL ESTERS AND A618/34 (2006.01) METHODS OF MANUFACTURE A61O5/10 (2006.01) A61O 1/02 (2006.01) (71) Applicants: Dorie J. YONTZ, Bloomington, MN A647/22 (2006.01) (US); Lee Richard RIETH, Plymouth, AOIN 25/00 (2006.01) MN (US); Nicholas MORANTE, A61O 1704 (2006.01) Holbrook, NY (US): Irwin PALEFSKY, A6R8/97 (2006.01) Fairfield, NJ (US) (52) U.S. Cl. CPC ................ A61K 8/498 (2013.01); A61O 1704 (72) Inventors: Dorie J. YONTZ, Bloomington, MN (2013.01); A61O 15/00 (2013.01); A61 K (US); Lee Richard RIETH, Plymouth, 8/4973 (2013.01); A61K 8/35 (2013.01); A61 K MN (US); Nicholas MORANTE, 8/368 (2013.01); A61K 8/97 (2013.01); A61 K Holbrook, NY (US): Irwin PALEFSKY, 8/34 (2013.01); A61K 8/4953 (2013.01); A61O Fairfield, NJ (US) 5/10 (2013.01); A61O 1/02 (2013.01); A61 K 47/22 (2013.01); A0IN 25/00 (2013.01); A61O (73) Assignee: SEGETIS, INC., Golden Valley, MN 9/04 (2013.01); A61 K 2800/49 (2013.01) (US) USPC .. 424/59: 424/62; 424/65; 514/467: 514/452: 514/159: 424/744: 514/275: 8/416: 8/421; (21) Appl. No.: 14/535,989 8/424; 8/161 (22) Filed: Nov. 7, 2014 (57) ABSTRACT Personal care formulations containing alkyl ketal esters hav Related U.S. Application Data ing the structure (62) Division of application No. 13/104,570, filed on May 10, 2011, now abandoned. I (60) Provisional application No. 61/332,982, filed on May -R 10, 2010, provisional application No. 61/332,978, CH, O filed on May 10, 2010. H2 s CH YO Publication Classification R2 O (51) Int. Cl. CH1 A6 IK 8/49 (2006.01) A61O 15/00 (2006.01) wherein a is 0 or an integer of 1 to 12: b is 0 or 1; R is a A6 IK 8/35 (2006.01) divalent Cls group optionally Substituted with up to 5 A6 IK 8/368 (2006.01) hydroxyl groups; and R' is C, alkyl. US 2015/0064124 A1 Mar. 5, 2015 PERSONAL CARE FORMULATIONS least one of the co-continuous phases is an oil phase; and CONTAINING ALKYL KETAL ESTERS AND wherein any of the foregoing oil phases comprises at least one METHODS OF MANUFACTURE of (a) a paraffinic, naphthenic or aromatic mineral oil, (b) a nonionic organic compound having a melting temperature of CROSS-REFERENCE TO RELATED less than 45°C., a molecular weight of at least 190 Daltons, an APPLICATIONS amido or ester group, and an alkyl chain containing at least 8 0001. This application is a divisional of U.S. Ser. No. carbon atoms, and a solubility in water of no greater than 1 13/104,570, filed May 10, 2011, which claims the benefit of part in 99 parts of water, (c) a nonionic organosilicone com U.S. Provisional Application No. 61/332,978, filed May 10, pound having a melting temperature of less than 45° C., and 2010, and to U.S. Provisional Application No. 61/332,982, a solubility in water of no greater than 1 part in 99 parts of filed May 10, 2010, all of the foregoing being incorporated water, (d) along chain alcohol, or (e) a wax; and (ii) an alkyl ketal ester of structure I. herein by reference in their entirety. 0007. In still another embodiment, a personal care formu FIELD OF THE INVENTION lation comprises an alkyl ketal ester of structure I, and an additional cosmetically acceptable ingredient. 0002 This invention relates to personal care formulations 0008. The invention is further illustrated by the following that contain certain alkyl ketal ester compounds and to meth Detailed Description, Examples, and Claims. ods for the manufacture of the formulations. DETAILED DESCRIPTION BACKGROUND 0009. We have found that certain alkyl ketal esters of 0003 Personal care formulations are available in a wide Structure I are excellent formulatory ingredients that provide range of formulation forms and are used in a wide variety of benefit in a wide number of personal care formulations. The specialized applications. Because these various types of for alkyl ketal esters are excellent solvents for a wide range of mulations differ enormously, as do the conditions under materials, including active agents useful in personal care which they are used, the individual formulations tend to be formulations. Many of them are at least partially miscible formulated specifically for the end-use application for which with water or other organic solvents, or both, as well as a wide they are intended. Further, the use of materials based on range of somewhat hydrophobic materials as are commonly renewable resources is becoming of increasing interest as present in personal care formulations. The alkyl ketal esters formulators redesign their formulations to meet environmen have low volatility. Under normal conditions of manufacture, tal sensitivities of their consumer bases. storage, and use, the alkyl ketal esters are not reactive with many of the other materials that are commonly found in SUMMARY personal care formulations. 0004 Disclosed herein are personal care formulations, the 0010 Because of these attributes, the alkyl ketal esters are personal care formulations comprising an alkyl ketal ester useful in a wide range of personal care formulations, includ having the structure ing formulations that contain various types of active agents as described below, as well as formulations that do not contain Such active agents. The alkylketal esters can provide a range of benefits to the formulation. The particular benefits seen in R1 any given formulation will depend on the particular ingredi CH, O1 ents and function of that formulation. HC1 O 0011. In an embodiment, the alkyl ketal esters of structure CH O I can be used to enhance the solubility of an active agent in a R2 O personal care formulation. Depending on the native solubility CH1 of the active agent in the formulation and the type of formu lation, the alkyl ketal ester can be used as a cosolvent with water, as a compatibilizer with water and an organic solvent, whereina is 0 or an integer of 1 to 12, b is 0 or 1, Radivalent as a cosolvent with an organic solvent, as an emulsifier, or a Cs group optionally substituted with up to 5 hydroxyl combination comprising of any of one or more of the forego groups, and R' is C. alkyl; and an active agent selected from ing. As is known to those of skill in the art of formulating organic anti-aging agents, organic anti-acne agents, organic personal care products, an individual ingredient can have skin whiteners, organic ultraViolet light absorbers, organic more than one type of function, for example a given alkyl tanning agents, organic anti-alopecia agents, antifungal ketal ester could function both as a cosolvent and as a com agents, anti-dandruff active agents, antimicrobial agents, patibilizer. organic medicinals, depilatory compounds, hair dyes, organic 0012. When the active agent has limited water solubility, insect repellants, and combinations thereof. the alkyl ketal ester can in Some embodiments function as a 0005 Also disclosed is a waxy personal care formulation cosolvent, together with water. Many alkyl ketal esters are comprising a wax, an emollient, and an alkyl ketal ester of good solvents for active agents and also have good miscibility structure I. in water. The presence of Such an alkyl ketal ester can allow 0006. In another embodiment, a personal care formulation the concentration of the active agent to be increased, often in the form of an emulsion comprises (i) a continuous phase without the presence of volatile organic compounds (VOCs) and a disperse phase wherein the continuous phase or the Such as ethanol, isopropanol, acetone, ethyl acetate, and the disperse phase is an aqueous phase and the other is an oil like in the formulation. The result in some cases can be a more phase; or at least two co-continuous phases wherein at least concentrated low VOC formulation. The alkyl ketal ester can one of the co-continuous phases is an aqueous phase and at also perform additional functions, such as compatibilization US 2015/0064124 A1 Mar. 5, 2015 of aqueous and organic phases, compatibilization or solubi 0017. Because the alkyl ketal ester is a good solvent for a lization of certain organic materials into an aqueous phase, wide range of materials, it is very useful for making concen emulsification of an oil phase into an aqueous phase or of an trates, which can be let down into water, an alcohol or other aqueous phase into an oil phase. diluent. 0013 The alkyl ketal ester can act as an emulsifier, com 0018 Still another benefit of the alkyl ketal ester in some patibilizer, or solubilizer for ingredients other than the active formulations is that it allows the amount of water to be agent, or as a co-emulsifier, co-compatibilizer, or co-solubi increased in otherwise highly hydrophobic formulations. lizer for ingredients other than the active agent, in particular This can provide a moisturizing function in Some cases, or if the alkyl ketal ester is highly water-soluble. Moreover, provide other benefits. A notable example of this is in lip care incorporation of the alky ketal ester can lead to a lighter, less formulations, particularly lipsticks, lip glosses, and lip balms, greasy or heavy-feeling formulation, especially compared to and cuticle balms which are based on waxes and other highly many other naturally-derived ingredients.
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