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United States Patent (19) 11 Patent Number: 5,885,593 Epstein (45) Date of Patent: *Mar 23, 1999

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United States Patent (19) 11 Patent Number: 5,885,593 Epstein (45) Date of Patent: *Mar 23, 1999 USOO588.5593A United States Patent (19) 11 Patent Number: 5,885,593 Epstein (45) Date of Patent: *Mar 23, 1999 54 SKIN CARE COMPOSITION INCLUDING 5,476,852 12/1995 Cauwenbergh ......................... 514/252 CYCLODEXTRIN MATERIALS AND 5,648,380 7/1997 Martin ......... ... 514/461 METHOD FOR TREATING SKIN 5,674,912 10/1997 Martin ..................................... 514/724 THEREWITH FOREIGN PATENT DOCUMENTS 75 Inventor: Howard Epstein, Rochester, N.Y. 4-74107 3/1992 Japan. 73 Assignee: The Andrew Jergens Company, OTHER PUBLICATIONS Cincinnati, Ohio “Hydroxy Acids and Skin Aging,” Cosmetics & Toiletries * Notice: This patent issued on a continued pros- Magazine, yo), 109, Sep. 1994, pp. 41-48. ecution application filed under 37 CFR Brochure: “B Cyclodextrin Kleptose(R, The Newa Approach 1.53(d), and is subject to the twenty year to Molecular66 Encapsulation”- - by Roquette Fréres, 1992. patent term provisions of 35 U.S.C. Brochure: “Cavitron Cyclo-Dextrins, A Breakthrough for 154(a)(2). Molecular Encapsulation,” by Amaizo, 1991. “Solving Problems with Cyclodextrins in Cosmetics,” Cos 21 Appl. No.: 682,333 G's. cc Toiletries Magazine, vol. 108, Nov. 1994, pp. 22 Filed: Jul. 17, 1996 Primary Examiner José G. Dees O O ASSistant Examiner Michael A. Williamson Relatedeae U.S. Applicationpplication DatUata Attorney, Agent, or Firm-Oblon, Spivak, McClelland, 60 Provisional application No. 60/005,692, Sep. 28, 1995. Maier & Neustadt, P.C. (51) Int. Cl." ....................................................... A61K 7/48 57 ABSTRACT 52 U.S. Cl. .......................... 424/401; t There is disclosed a method for treating skin along with a 14/847; 514/873 novel skin care composition comprising the following com 58 Field of Search ............................. s' S.S. ponents in a Suitable carrier: /844, s (a) from about 1 to about 10 weight percent of a cyclo 56) References Cited dextrin material; and (b) from about 1 to about 15 weight percent of an acid U.S. PATENT DOCUMENTS material Selected from: 3,879,537 4/1975 Van Scott ................................ 424/311 alpha hydroxy acids, beta hydroxy acids, alpha keto 3,920.835 11/1975 Van Scott ..... ... 424/311 acids, beta keto acids, and combinations thereof. 3,984,566 10/1976 Van Scott ..... ... 424/283 4,105,783 8/1978 Yu ............ ... 424/283 The skin care composition includes a cyclodextrin material 4,197,316 4/1980 Yu ............ ... 424/317 to reduce the irritation and Stinging caused by the presence 4,234,599 11/1980 Van Scott ..... - - - - 424/279 of the aforementioned acid materials. 4,380,549 4/1983 Van Scott ..... ... 424/317 4.389,418 6/1983 Burton ..... ... 424/365 5,091,171 2/1992 Yu ........................................... 424/642 18 Claims, No Drawings 5,885,593 1 2 SKIN CARE COMPOSITION INCLUDING alpha hydroxy acids, beta hydroxy acids, alpha keto CYCLODEXTRIN MATERIALS AND acids, beta keto acids, and combinations thereof. METHOD FOR TREATING SKIN The skin care composition of the present invention may THEREWITH comprise both oil-in-water (water-out) emulsions and water in-oil (oil-out) emulsions. Such emulsions and their formu lation are well known in the art. Emulsifiers employed Such This application claims the benefit of U.S. Provisional formulations have traditionally included anionic (e.g. Application No(s). 60/005,692, filed Sep. 28, 1995. Sodium lauryl Sulfates, ammonium Stearate, Sulfated castor oil, dioctyl Sodium SulfoSuccinate), nonionic (e.g. PEG FIELD OF THE INVENTION gylceryl), amphoteric, cationic, and mixtures thereof. By The present invention generally relates to the use of 1O way of example, U.S. Pat. No. 4,389,418 to Burton discloses cyclodextrin materials to reduce the irritation and Stinging a skin care compositions including a cationic emulsifier, i.e. caused by acid materials, e.g. alpha hydroxy acids, used a quaternary ammonium compound. Another example of a within skin care compositions. nonionic formulation is provided in the example Section below. BACKGROUND OF THE INVENTION 15 The cyclodextrins used in the present invention are cycli coligosaccarides produced by the enzymatic degradation of Alpha and beta hydroxy (and keto) acids have been used Starch and have multiple glucose or glucopyranose units, in a wide variety of skin care compositions to remove dead usually 6 to 8 units. Depending on the particular preparation cells from the Surface of the skin and to assist in skin reaction conditions employed, cyclodextrins generally con moisturization. See U.S. Pat. Nos. 3,879,537, 3,920,835, tain Six, Seven or eight of Such units, connected by alpha 3,984,566, 4,105,783, 4,197,316, 4,234,599, 4,380,549, and (1,4) bonds. The Six, Seven or eight unit cyclodextrins are 5,091,171. Also see Smith, W. P., “Hydroxy Acids and Skin commonly known as alpha-, beta-, and gamma Aging,” Cosmetics & Toiletries, Vol. 109, pp. 41-48 cyclodextrins, respectively. A particularly preferred beta (September, 1994). Such acids are of interest in skin care cyclodextrin material is available from Amaizo American compositions because of the demand for products that 25 Maize-Products Co. under the trade no. 410-105. diminish the appearance of fine lines on the face and Cyclodextrins are well known and are commercially improve the appearance of flaking or dry skin. Although produced by the enzymatic degradation of Starch. For Such acid materials offer a number of advantages, they also example, beta-cyclodextrin is the major product of the commonly cause skin irritation and Stinging, particularly reaction between the enzyme cyclodextrin transglycosylase when used in effective concentrations, i.e. greater than about and a starch Solution pretreated with gamma-amylase. 1 weight percent, and more commonly around 3 to about 15 Cyclodextrins have the shape of truncated cones with weight percent. The irritation caused by Such acid materials primary and Secondary hydroxyl groups located at opposite is most noticeable in applications of skin care compositions ends of the torus. The glucosyl-o-bridges point into the to Sensitive skin areas, e.g facial application. AS Such, the center of the molecule and the primary hydrogel groups application Such skin care compositions are often limited. 35 project from one outer edge while the Secondary hydroxyl groups project from the other edge. The result is a molecule SUMMARY OF THE INVENTION with a relatively hydrophobic center and a hydrophilic outer The present invention is directed toward reducing the Surface. These shapes and hydrophilic/hydrophobic domains irritation and Stinging associated with skin care composition provide for inclusion or incorporation of guest molecules including alpha and beta hydroxy and/or alpha and beta keto 40 into the center of the molecule. acids in amounts greater than about 1 weight percent and AS used herein, the term “cyclodextrins' includes cyclo typically between about 3 to about 15 weight percent. The dextrin derivatives, Such as cyclodextrin carbonates, ethers, present invention includes the use of cyclodextrin materials esters, and polyethers, polymers or copolymers of polymer which Significantly reduces the aforementioned irritation. ized cyclodextrins, Such as polymerized beta-cyclodextrins, More specifically, the present invention includes a method 45 and Substituted cyclodextrins Such as those with functional for treating skin along with a skin care composition com groupS bonded to one or more of the hydroxyl groups. prising the following components in a Suitable carrier: Suitable function groups include, but are not limited to, (a) from about 1 to about 10 weight percent of a cyclo methyl, ethyl, hydroxyethyl, and hydroxypropyl and acetyl dextrin material; groups. Cyclodextrins of particular applicability to the 50 present invention include hydroxyalkyl beta cyclodextrins, (b) from about 1 to about 15 weight percent of an acid e.g. hydroxy propyl and hydroxy ethyl beta cyclodextrin, material Selected from: beta cyclodextrin crosslinked with epichlorohydrin, and alpha hydroxy acids, beta hydroxy acids, alpha keto other modified cyclodextrins Such as those commercially acids, beta keto acids, and combinations thereof. available from the Amaizo, American Maize-Products Com DETAILED DESCRIPTION OF THE 55 pany under the Cavitron Cyclo-dextrinsTM mark. INVENTION Acid materials applicable to the present invention include alpha and beta hydroxy acids and alpha and beta keto acids. The present invention includes a method for treating skin Such acid materials are well known for use in skin care along with a skin care composition used therein. The present compositions and are described in U.S. Pat. Nos. 3,879,537, method comprises the Step of applying the Subject Skin care 60 3,920,835, 3,984,566, 4,105,783, 4,197,316, 4,234,599, composition to the skin, wherein the Subject Skin care 4,380,549, and 5,091,171. Such materials should be phar composition comprises the following components in a Suit maceutically acceptable and have an acidic disasSociation able carrier: constant (pK) within the range of about 1 to about 6, (a) from about I to about 10 weight percent of a cyclo preferably about 2.5 to about 5.0 (measured at 25 C.), and dextrin material; 65 more preferably about 3 to about 4. (b) from about 1 to about 15 weight percent of an acid Hydroxy polycarboxylic acids may be provided as the material Selected from: alpha or beta analogs and may be present as free acids, 5,885,593 3 4 peroxides, lactones, amides, esters, or Salts. Illustrative of weight percent, more preferably about 1 to about 20 weight the variety of acids included are Saccharic acid, percent, and still more preferably about 5 to about 15 weight 2-hydroxyglutaric acid, 3,4-dihydroxyglutamic acid, 2.5- percent. dihydroxy-6-aminohexanoic acid, acetopyruvic acid, acetyl The Subject Skin care composition may include additional pyruvic acid, beta-fluoropyruvic acid, tartaric acid, citric components Such as (a) petrolatum or mineral oil, (b) fatty acid, 2-hydroxybenzoic acid (Salicylic acid), 2-hydroxy-2- alcohols, (c) fatty ester emollients, (d) Silicone oils or fluids, methylbutyric acid, 2-hydroxy isobutyric acid, mandelic and (e) preservatives.
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