USOO8852615B1 (12) United States Patent (10) Patent No.: US 8,852,615 B1 Harrison et al. (45) Date of Patent: *Oct. 7, 2014 (54) CLEAR, GREASELESS SKIN-CARE 4,935,224 A 6, 1990 Russo et al. COMPOSITIONS 4,997,853. A 3, 1991 Bernstein 5,013,726 A 5/1991 Ivy et al. 5,082,661 A 1/1992 Melnik et al. (75) Inventors: James Jeffries Harrison, West Hills, 5,124,320 A 6/1992 Ivy et al. CA (US); Nohemi Harrison, West Hills, 5,607,980 A 3, 1997 McAtee et al. CA (US) 5,759,529 A 6/1998 LeGrow et al. 5,856,361 A 1/1999 Holt et al. 5,916,548 A 6/1999 Hutchins et al. (73) Assignee: Chemsil Silicones, Inc., Chatsworth, CA 5,993,837 A 11/1999 Calello et al. (US) 6,103,266 A 8/2000 Tapolsky et al. 6,106,820 A 8/2000 Morrissey et al. (*) Notice: Subject to any disclaimer, the term of this 6,124,490 A 9/2000 Gormley et al. patent is extended or adjusted under 35 6,296,880 B1 10/2001 Murad U.S.C. 154(b) by 0 days. 6,338,855 B1 1/2002 Albacarys et al. 6,348,501 B1 2/2002 Holt et al. This patent is Subject to a terminal dis 6,372,234 B1 4/2002 Deckers et al. claimer. 6,383,523 B1 5, 2002 Murad 6,384,023 B2 5/2002 Singleton et al. 6,403,069 B1 6/2002 Chopra et al. (21) Appl. No.: 13/030.947 6,406,683 B1 6/2002 Drechsler et al. 6,419,913 B1 7/2002 Niemiec et al. (22) Filed: Feb. 18, 2011 6,503,517 B1 1/2003 Mohammadi et al. Related U.S. Application Data OTHER PUBLICATIONS (60) Division of application No. 10/855,934, filed on May USPTO Office action dated Dec. 8, 2009 in related U.S. Appl. No. 26, 2004, which is a continuation-in-part of 10/855,934, filed May 26, 2004. application No. 10/254,418, filed on Sep. 25, 2002, USPTO Office action dated Mar. 5, 2009 in related U.S. Appl. No. now abandoned. 10/855,934, filed May 26, 2004. USPTO Office action dated Sep. 5, 2008 in related U.S. Appl. No. 10/855,934, filed May 26, 2004. (51) Int. Cl. USPTO Office action dated Jan. 25, 2008 in related U.S. Appl. No. A61O 19/00 (2006.01) 10/855,934, filed May 26, 2004. A6 IK 8/89 (2006.01) A6 IK3I/07 (2006.01) * cited by examiner (52) U.S. Cl. USPC ........... 424/401; 424/70.12: 514/63; 514/725 Primary Examiner — Lakshmi Channavaljala (58) Field of Classification Search CPC ..... A61Q 19/00; A61Q 19/02: A61O 19/007; (57) ABSTRACT A61K 8/89; A61K 8/585 The present invention relates to compositions including anhy See application file for complete search history. drous compositions which include a dimethicone crosspoly mer and/or dimethicone elastomer gum and one or more skin (56) References Cited care products which may include retinoic acid, retinoic acid derivatives, retinal, retinol and/or retinyl esters, and methods U.S. PATENT DOCUMENTS of making, storing, and using Such compositions. 4,608,392 A 8/1986 Jacquet et al. 4,888,363 A * 12/1989 Dulak et al. .................. 514,725 11 Claims, No Drawings US 8,852,615 B1 1. 2 CLEAR, GREASELESS SKIN-CARE Two classes of pharmaceutical compositions particularly COMPOSITIONS prone to the aforementioned drawbacks are skin-care com positions and analgesics. RELATED APPLICATIONS Of special interest in the category of skin care composi tions are compositions including anti-wrinkle components, This is a divisional of copending U.S. patent application anti-skin atrophy components, skin repair components and Ser. No. 10/855,934, filed May 26, 2004, which is a continu mixtures thereof, and particularly skin care compositions ation-in-part of U.S. patent application Ser. No. 10/254,418, selected from the group consisting of retinoic acid, retinoic filed Sep. 25, 2002, the disclosure of each of which is hereby acid derivatives, retinal, retinol, retinyl esters and mixtures incorporated herein in its entirety by reference. 10 thereof. Retinol, perhaps the most well known of these composi FIELD OF THE INVENTION tions, is frequently used in anti-aging creams, lotions, and serums. Because retinol is very unstable to heat, light, and The present invention relates to clear, greaseless composi oxygen, products containing retinol currently must be manu 15 factured under inert gas conditions and packaged in alumi tions which include a pharmaceutically active component. num tubes to prevent oxygen or light from degrading the The compositions are preferably anhydrous and include sili active retinol. These restrictive manufacturing and packaging cones, for example, one or more of dimethicone crosspoly conditions increase the overall cost of the skin-care products, mers, dimethicone gum, hexamethyldisiloxane and low making them unaffordable to many consumers. molecular weight dimethicones. Also of interest are analgesic compositions, particularly More particularly, the composition may be a topically compositions selected from the group consisting of methyl applied composition containing one or more analgesics or salicylate, camphor, menthol and capsaicin. Methyl salicylate one or more skin care components. is a 2-hydroxybenzoic acid methyl ester which can occur In a further and more specific aspect, the invention relates naturally in wintergreen oil, betula oil, Sweet birch oil, teab to clear, greaseless compositions including a pharmaceuti 25 erry oil and in the leaves of Gualtheria procumbens L. Eri cally active component such as an analgesic including methyl cadeae and in the bark of Betula lenta L. Betulaceae. It can salicylate, camphor, menthol and capsaicin or a skin care also be prepared by etherification of salicylic acid with component selected from the group consisting of anti-wrinkle methanol. Camphor is 1,7,7-trimethylbicyclo2.2.1]heptan components, anti-skin atrophy components, skin repair com 2-one and occurs in all parts of the camphor tree, Cinnamo ponents, and mixtures thereof. Advantageously, the pharma 30 mum camphora T. It is also synthesized from vinyl chloride ceutically active component is a skin care component selected and cyclopentadiene. Menthol, or 5-methyl-2-1-methyl from the group consisting of retinoic acid, retinoic acid ethyl-cyclohexanol, can be obtained from mint oils, for derivatives, retinal, retinol, retinyl esters and mixtures example, peppermint oil. It can also be obtained through thereof. hydrogenation of thymol. Capsaicin, or N-(4-hydroxy-3- 35 methoxybenzyl)-8-methylnontrans-6-enamide, can be BACKGROUND obtained from the fruits of plants of the Capsicum genus. Water and oil containing compositions such as gels, lotions Various pharmaceutical products are designed for topical and creams are useful for application of menthol, camphor, application, for instance in the form of gels, creams and and capsaicin and methyl salicylate as well as other analge lotions. Among such products are compositions including 40 sics. U.S. Pat. No. 5,124,320 and U.S. Pat. No. 5,013,726 anti-acne actives, antimicrobial and antifungal actives, anti disclose compositions in which methyl salicylate, menthol wrinkle and anti-skin atrophy actives, skin barrier repair aids, and camphor are dissolved into C12-C15 alcohols benzoate, cosmetic Soothing aids, artificial tanning agents and accelera eucalyptus oil and jojoba oil. tors, skin lightening actives, Sunscreen actives, skin tighten There remains a need for topically applied compositions ing agents, anti-itch agents, hair growth inhibitors, descqua 45 which may be used to apply skin-care products. and/or anal mating agents, antiglycation agents, wound healing actives, gesics which are easily and economically prepared, are non actives to treat psoriasis, skin cancer, impetigo, herpes, chick Sticky, greaseless, require less drying time after application to enpox and dermatitis and mixtures thereof. the skin, do not stain the skin, provide water resistance or Some of the above compositions include components that waterproofing, act to efficiently retain actives and are not are insoluble or only slightly soluble in water, but are readily 50 irritating to the skin. soluble in non-polar substances such as organic Solvents and In addition, a need exists for skin-care products, particu oils. However, compositions including oils and the like have larly retinol-containing skin-care products, which can be eco certain drawbacks in their use. For example, they may pro nomically packaged in opaque containers and which remain duce a sticky and/or greasy feel upon application to the skin. stable when exposed to oxygen and/or higher than normal The compositions may also be inconvenient for use by, for 55 temperatures. example, requiring an extended drying time after application to the skin and/or staining the skin and/or clothing. In addi SUMMARY tion, these compositions do not necessarily provide for a film layer that will be effective to retain volatile actives. Further, The present invention meets these needs. Compositions of after application the compositions typically are easily solu 60 the invention can be manufactured at relatively low cost under bilized by aqueous solutions such as perspiration which may non-restrictive conditions. Such compositions are preferably lead to loss of the composition and/or the actives. Further, anhydrous with no oily component, and as Such have a water or oil containing compositions often include emulsifi reduced greasy feel relative to similar or identical composi ers which can cause skin irritation. In addition, the process of tions which include oil and/or water. Advantageously, the making these compositions typically involves heating which 65 compositions will dry in a reduced period of time relative to may lead to the loss of the actives by, for example, evapora similar or identical compositions which include oil and/or tion and/or Sublimation.