WO2000013658A1

WO2000013658A1 - A composition containing insect repellent

Info

Publication number: WO2000013658A1
Application number: PCT/US1998/018251
Authority: WO
Inventors: Gong-Xiang Chen; Hidekazu Tanaka
Original assignee: The Procter & Gamble Company
Priority date: 1998-09-02
Filing date: 1998-09-02
Publication date: 2000-03-16
Also published as: AU9129498A

Abstract

Disclosed is a composition having insect repellent benefits containing: (a) an active compound having formula (I); (b) a water-soluble polymer; and (c) a hydrophilic liquid carrier, wherein R?1 and R2¿ are independently selected from saturated, straight or branched alkyl group of from 1 to about 10 carbons. Preferred compositions include skin care composition in gel, lotion and liquid forms.

Description

A COMPOSITION CONTAINING INSECT REPELLENT

FIELD

The present invention relates to a topical composition. In particular, it relates to an insect repellent composition.

BACKGROUND

Consumers frequently use insect repellent products, for example, to protect from insect bites including mosquitoes, alone or along with cosmetic products, during an outdoor activity such as hiking, champing, and hunting.

These products, which come in the form of liquids, creams, pastes and gels, are rubbed, sprayed, or otherwise applied to the skin.

Many substances have been suggested through the years to be used in such repellence products as insect repellence actives including dimethyl phthalate and N,N-diethyl-m-toluamide. N,N-diethyl-m-toluamide is the most widely used insect repellent active sometimes referred to as "DEET." See U.S.

Patent 2,932,665, Wagner et al, issued on April 12, 1960, U.S. Patent 4,756,905,

Melnik, issued July 12, 1988, U.S. Patent 4,416,881 , McGovem et al, and U.S.

Patent 4,419,360, Smolanoff. DEET is very effective in protecting an outdoorsman from insects, provided it is properly applied such that it adequately covers the skin of the user.

However, relatively high concentrations of insect repellent actives such as

DEET may give rise to allergic or toxic reactions in some individuals when applied to the skin. Of course, it is well known that different individuals may exhibit significantly different allergic reactions to a given substance. In addition, some of the known insect repellent actives including DEET possess may become undesirable to some individuals at relatively high concentrations.

Based on the foregoing, there is a need for a composition containing insect repellent actives, which is natural and safe to the skin and provides prolonged efficacy of the actives. SUMMARY

This need is met by the present invention wherein compositions having superior insect repellent properties is proposed The composition contains (a) an active compound having the formula

(b) a water-soluble polymer, and

(c) a hydrophilic liquid carrier, wherein R^ and R^ are independently saturated, straight or branched alkyl of 1 to about 10 carbons

These and other features, aspects, and advantages of the present invention will become better understood from a reading of the following description, and appended claims

DETAILED DESCRIPTION

While the specification concludes with claims particularly pointing out and distinctly claiming the invention, it is believed that the present invention will be better understood from the following description

All percentages and ratios used hereinafter are by weight of total composition, unless otherwise indicated

All measurements referred to herein are made at 25°C unless otherwise specified.

All percentages, ratios, and levels of ingredients referred to herein are based on the actual amount of the ingredient, and do not include solvents, fillers, or other materials with which the ingredient may be combined as a commercially available product, unless otherwise indicated

All publications, patent applications, and issued patents mentioned herein are hereby incorporated in their entirety by reference Citation of any reference is not an admission regarding any determination as to its availability as prior art to the claimed invention

Herein, "comprising" means that other steps and other ingredients which do not affect the end result can be added This term encompasses the terms "consisting of and "consisting essentially of Herein, "topical application" means to apply or spread a material onto the surface of the skin

Herein, "dermatologically-acceptable" means that the compositions or components thereof so described are suitable for use in contact with human skin without undue toxicity, incompatibility, instability, allergic response, and the like

Herein, "safe and effective amount," means an amount of a compound or composition sufficient to significantly induce a positive^' benefit, preferably a positive skin appearance or feel benefit, including independently the benefits disclosed herein, but low enough to avoid serious side effects, e g , to provide a reasonable benefit to risk ratio, within the scope of sound judgment of the skilled artisan

All ingredients such as actives and other ingredients useful herein may be categorized or described by their cosmetic and/or therapeutic benefit or their postulated mode of action However, it is to be understood that the active and other ingredients useful herein can, in some instances, provide more than one cosmetic and/or therapeutic benefit or operate via more than one mode of action Therefore, classifications herein are made for the sake of convenience and are not intended to limit an ingredient to the particularly stated application or applications listed The topical composition of the present invention contains

(a) an active compound having the formula

(b) a water-soluble polymer, and

(c) a hydrophilic liquid carrier, wherein R¹ and R^ are independently selected from saturated, straight or branched alkyl groups of from 1 to about 10 carbons The composition is, preferably, a dermatologically-acceptable topical composition, more preferably, a cosmetic composition. The composition provides superior insect repellent efficacy, especially prolonged repellent efficacy A Active compound

The composition of the present invention contains a safe and effective amount of an active compound having the formula

wherein R^ and R² are independently selected from saturated, straight or branched alkyl groups of from 1 to about 10 carbons

In the above structure, preferably R¹ and R² are independently selected from saturated, straight alkyl groups of from 1 to about 3 carbons More preferably, R^ IS methyl and R² IS methyl, ethyl, or propyl

The active compound (I) of the present invention provides strong activity to repel insects such as mosquitoes and gnats It is believed that repellent mechanism of the formula (I) is that the active compounds work only for repelling insects instead of killing them.

Preferably, the composition contains from about 0 5% to about 50% of the active compound, more preferably from about 1 % to about 10%

In one embodiment, the active compound can be derived by a method described in Chinese patent application No 94100746, Hanzhi et al , filed on July 26, 1995.

B. Water-soluble polymer

The composition of the present invention contains a water-soluble polymer The water-soluble polymers are selected from the group consisting of a carbonic acid polymer, a polysacchaπde, a gum, and mixtures thereof Preferably, the composition contains from about 0 01% to about 20% of the water-soluble polymer, preferably from about 0 1 % to about 5%

While not wishing to be bound by theory, it is believed that water-soluble polymer prevents and/or retards an evaporation of the repellent active into the atmosphere and minimize the penetration of the repellent actives into the skin Such performances tend to show the repellent active compound staying on the skin surface longer, resulting in a longer lasting repellent efficacy While not wishing to be bound by theory, it is believed that prevention of the evaporation of the active compounds and the reducing of the penetration of the active compounds to skin can be explained by one of the following three mechanisms 1) a film formed by the water-soluble polymer tends to provide a physical barrier to the repellent molecules,

2) the water-soluble polymers macro-molecules tend to randomly embody the repellent molecules, and 3) hydrophilic groups on the water-soluble polymer molecules tends to form strong hydrogen bonds with the repellent molecules through the hydroxyl and/or oxygen groups on the repellent molecules.

Accordingly, the repellent actives can stay on the skin surface longer, resulting in providing long lasting repellent efficacy

Nonlimiting examples of suitable water-soluble polymers in the compositions herein include carboxylic acid polymers, polysacchaπdes, and gums.

(0 Carboxylic Acid Polymers The carboxylic acid polymers useful in the present invention are crosslinked compounds containing one or more monomers derived from acrylic acid, substituted acrylic acids, and salts and esters of these acrylic acids and the substituted acrylic acids, wherein the cross nking agent contains two or more carbon-carbon double bonds and is derived from a polyhydric alcohol. The preferred carboxylic acid polymers are of two general types. The first type of polymer is a crosslinked homopolymer of an acrylic acid monomer or derivative thereof (e.g., wherein the acrylic acid has substituents on the two and three carbon positions independently selected from the group consisting of C-j_4 alkyl, -CN, -COOH, and mixtures thereof) The second is a crosslinked copolymer having a first monomer selected from the group consisting of an acrylic acid monomer or derivative thereof (as just described in the previous sentence), a short chain alcohol {i.e., a C-|_4) acrylate ester monomer or derivative thereof {e.g., wherein the acrylic acid portion of the ester has substituents on the two and three carbon positions independently selected from the group consisting of C-|_4 alkyl, -CN, -COOH, and mixtures thereof), and mixtures thereof; and a second monomer which is a long chain alcohol {i.e., C_β- 4θ) acrylate ester monomer or derivative thereof {e.g , wherein the acrylic acid portion of the ester has substituents on the two and three carbon positions independently selected from the group consisting of C-1.4 alkyl, -CN, -COOH, and mixtures thereof). Combinations of these two types of polymers are also useful herein.

In the first type of crosslinked homopolymers, the monomers are preferably selected from the group consisting of acrylic acid, methacrylic acid, ethacrylic acid, and mixtures thereof, with acrylic acid being most preferred In the second type of crosslinked copolymers the acrylic acid monomer or derivative thereof is preferably selected from the group consisting of acrylic acid, methacrylic acid, ethacrylic acid, and mixtures thereof, with acrylic acid, methacrylic acid, and mixtures thereof being most preferred. The short chain alcohol acrylate ester monomer or derivative thereof is preferably selected from the group consisting of C-_|_4 alcohol acrylate esters, Cι _4 alcohol methacrylate esters, C1.4 alcohol ethacrylate esters, and mixtures thereof, with the C-1.4 alcohol acrylate esters, C-_|_4 alcohol methacrylate esters, and mixtures thereof, being most preferred The long chain alcohol acrylate ester monomer is selected from the group consisting of Cs-40 alkyl acrylate esters, with C-ιo-30 ^a'kyl acrylate esters being preferred. The crosslinking agent in both of these types of polymers is preferably a polyalkenyl polyether of a polyhydric alcohol containing more than one alkenyl ether group per molecule, wherein the parent polyhydric alcohol contains at least 3 carbon atoms and at least 3 hydroxyl groups Preferred cross nkers are those selected from the group consisting of allyl ethers of sucrose and allyl ethers of pentaerythritol, and mixtures thereof. These polymers useful in the present invention are more fully described in U.S. Patent 5,087,445, Haffey et al, issued February 11 , 1992; U.S. Patent 4,509,949, Huang et al, issued April 5, 1985, U.S. Patent 2,798,053, Brown, issued July 2, 1957; CTFA International Cosmetic Ingredient Dictionary, fourth edition, 1991 , pp. 12 and 80, the disclosures of which are herein incorporated by reference.

Examples of commercially available homopolymers of the first type useful herein include the carbomers, which are homopolymers of acrylic acid crosslinked with allyl ethers of sucrose or pentaerythritol The carbomers are available as the Carbopol® 900 series from B.F. Goodrich {e.g , Carbopol® 954). Examples of commercially available copolymers of the second type useful herein include copolymers of C-|0-30 alkyl acrylates with one or more monomers of acrylic acid, methacrylic acid, or one of their short chain {i.e. C1.4 alcohol) esters, wherein the crosslinking agent is an allyl ether of sucrose or pentaerythritol. These copolymers are known as acrylates/C 10-30 alkyl acrylate crosspolymers and are commercially available as Carbopol® 1342, Carbopol® 1382, Pemulen TR-1 , and Pemulen TR-2, from B.F. Goodrich. In other words, examples of carboxylic acid polymer thickeners useful herein are those selected from the group consisting of carbomers, acrylates/C ι o-30 ^a|kyl acrylate crosspolymers, and mixtures thereof. (iQ Polysaccharides A wide variety of polysacchaπdes are useful herein as the water-soluble polymer Herein, "polysaccharides" refers to the water- soluble polymer containing a backbone of repeating sugar (/ e , carbohydrate) units Nonlimiting examples of polysacchaπde include those selected from the group consisting of cellulose, carboxymethyl hydroxyethylcellulose, cellulose acetate propionate carboxylate, hydroxyethylcellulose hydroxyethyl ethylcellulose, hydroxypropylcellulose, hydroxypropyl methylcellulose, methyl hydroxyethylcellulose, microcrystalline cellulose, sodium cellulose sulfate and mixtures thereof In the above examples, useful sacchaπsdes are the alkyl substituted celluloses The hydroxy groups of the cellulose polymer are preferably hydroxyalkylated (preferably, hydroxyethylated or hydroxypropylated) forming a hydroxyalkylated cellulose that is further modified with a Cι rj-30 straight or branched alkyl group of from about 10 to about 30 carbon atoms through an ether linkage Preferred polymers are ethers of straight or branched alcohols of from about 10 to about 30 carbons with hydroxyalkylcellulose

Examples of alkyl groups useful herein include those selected from the group consisting of stearyl, isostearyl, lauryl, myπstyl, cetyl, isocetyl, cocoyl (i e alkyl groups derived from the alcohols of coconut oil), palmityl, oleyl, linoleyl, linolenyl, πcinoleyl, behenyl, and mixtures thereof Preferred among the alkyl hydroxyalkyl cellulose ethers is the material given in the CTFA designation as cetyl hydroxyethylcellulose, which is the ether of cetyl alcohol and hydroxyethylcellulose This material is sold under the tradename Natrosol® CS Plus from Aqualon Corporation Other useful polysaccharides include scleroglucans comprising a linear chain of 1 to less than 3 linked glucose units with a 1 to less than 6 linked glucose every three units, a commercially available example of which is Clearogel™ CS11 from Michel Mercier Products Inc (Mountainside NJ)

(in) Gums Other water-soluble polymers useful herein include materials which are primarily derived from natural sources Nonlimiting examples of these gums include materials selected from the group consisting of acacia agar algin algmic acid, ammonium alginate, amylopectin, calcium algmate calcium carrageenan, carnitine, carrageenan, dextrin, gelatin, gellan gum, guar gum guar hydroxypropyltπmonium chloride, hyaluroinic acid, hydroxypropyl chitosan hydroxypropyl guar, karaya gum, kelp, locust bean gum, natto gum, potassium alginate, potassium carrageenan, propylene glycol alginate, sclerotium gum, sodium carboyxmethyl dextran, sodium carrageenan, tragacanth gum, xanthan gum, and mixtures thereof.

Other water-soluble polymers include those disclosed in U S Patent 4,387,107, Klein et al., issued June 7, 1983 and "Encyclopedia of Polymer and Thickeners for Cosmetics," R.Y. Lochhead and W R Fron, eds , Cosmetics & Toiletries, vol. 108, pp. 95-135 (May 1993), the disclosures of which are herein incorporated by reference. C. Hydrophilic liquid carrier The composition of the present invention contains a hydrophilic liquid carrier (HLC). Preferably, the composition contains from about 1 % to about 99% of HLC, more preferably from about 20% to about 95% The HLC includes water and one or more water soluble or dispersible ingredients

Suitable HLC includes conventional or otherwise known carriers that are dermatologically acceptable semi-solid or liquid fillers, diluents, solvents, extenders and the like HLC should also be physically and chemically compatible with the essential components described herein, and should not unduly impair stability, efficacy or other use benefits associated with the compositions of the present invention HLC also should be capable of being commingled in a manner such that there is no interaction which would substantially reduce the efficacy of the composition under ordinary use situations.

The type of HLC utilized in the present invention depends on the type of product form desired for the composition The topical compositions useful in the present invention may be made into a wide variety of product forms such as are known in the art. These include, but are not limited to, lotions, gels, sprays, and pastes (e.g., semi-solid or liquid make-up, including foundations). These product forms may include several types of carriers including, but not limited to, solutions, emulsions (oil-in-water or water-in-oil), gels, and liposomes Preferred HLC can contain a dermatologically acceptable, non-aqueous hydrophilic diluent. Nonlimiting examples of hydrophilic diluents are polyhydric alcohols such as low molecular weight monovalent alcohols (/ e , C-_| - Cβ) and low molecular weight glycols and polyols including propylene glycol, butylene glycol, hexylene glycol, dipropylene glycol, polyethylene glycol (e g , Molecular Weight 200-1000 g/mole), polypropylene glycol (e.g , Molecular Weight 425- 2025 g/mole), glycerol, 1 ,2,4-butanetriol, 1 ,2,6-hexanetriol, and combinations thereof.

D Additional Agent

The composition of the present invention may further contain an additional agent. Concentrations of the additional agent, preferably, are from about 1 % to about 99%>, more preferably from about 20% to about 95%

The additional agent useful herein includes a hydrophobic component or an amphiphilic surfactant, and mixtures thereof.

1. Hydrophobic Component Hydrophobic components useful in the present invention include a Iipid, oil, oily or other hydrophobic component

Preferably, the composition contains from about 1 % to about 98% of the hydrophobic component, more preferably from about 1 % to about 50%, and still more preferably from about 1 % to about 30%. The hydrophobic component may be derived from animals, plants, or petroleum and may be natural or synthetic (e.g., man-made). Preferred hydrophobic components are substantially water- insoluble. Preferred hydrophobic components are those having a melting point of about 40°C or less under about one atmosphere of pressure.

A wide variety of suitable hydrophobic components are known and may be used herein and numerous examples can be found in Sagarin, Cosmetics. Science and Technology. 2nd Edition, Vol. 1 , pp. 32-43 (1972) Nonlimiting examples of suitable hydrophobic components include mineral oil, petrolatum, C7-C40 straight and branched hydrocarbons, C-1 -C30 alcohol esters, glyceπdes alkylene glycol esters, propoxylated and ethoxylated derivatives, sugar ester, vegetable oils and hydrogenated vegetable oils, animal fats and oils, and C4- C20 alkyl ethers of polypropylene glycols, C1 -C20 carboxylic acid esters of polypropylene glycols, and di-Cs-C3o alkyl ethers. Examples of hydrophobic components useful herein are set forth in U.S. Patent 5,306,514, Letton et al_., issued April 26, 1994; Merck Index, Tenth Edition, Entry 7048, p 1033 (1983)_, and International Cosmetic Ingredient Dictionary, Fifth Edition, vol 1 , p 415-417 (1993).

2. Surfactant A surfactant useful herein, preferably, is capable of forming smectic lyotropic crystals in product or when the product is being applied to the skin at ambient or elevated temperatures. Once application of the product to the skin has been completed, liquid crystals may not be identifiable on the skin surface or stratum corneum. Preferably, the surfactant is capable of forming liquid crystals at a temperature from about 20°C to about 40°C

The surfactant useful herein can include any of wide variety nonionic, cationic, anionic, zwitterionic, and amphoteπc surfactant, preferably nonionic surfactant. The concentration of amphiphilic surfactant is preferably present at a level of from about 0.1 % to about 20%, preferably from about 0 1 % to about

10%.

Examples of surfactants useful herein are set forth in W097/28785, Tanner et al., issued August 14, 1998. E. Functional Optional component

The compositions of the present invention may include a wide variety of optional components that perform one or more functions useful in the applications. Preferably, any optional ingredients should be dermatologically acceptable. The optional ingredient should be physically and chemically compatible with the essential components described herein, and should not unduly impair stability, efficacy or other use benefits associated with the compositions of the present invention. Preferred optional ingredients are capable of being commingled in a manner such that there is no interaction which would substantially reduce the efficacy of the composition under ordinary use situations.

Nonexclusive examples of such materials are described in Harry's Cosmeticology, 7th Ed., Harry & Wilkinson (Hill Publishers, London 1982); in Pharmaceutical Dosage Forms- Disperse Systems; Lieberman, Rieger & Banker, Vols. 1 (1988) & 2 (1989); Marcel Decker, Inc , in The Chemistry and Manufacture of Cosmetics. 2nd. Ed., deNavarre (Van Nostrand 1962-1965), and in The Handbook of Cosmetic Science and Technology. 1 st Ed., Knowlton & Pearce (Elsevier 1993).

Preferred optional components include sunscreens or sunblocks, anti- oxidant/radical scavenger, anti-inflammatory agent, antimicrobial agents, chelating agent, and mixtures thereof.

1. Sunscreen and Sunblock Sunscreen and sunblock generally prevent excessive scaling and texture changes of the stratum corneum by exposure of ultraviolet light and may be added to the present invention Suitable sunscreens and sunblocks may be organic or inorganic. A wide variety of conventional sunscreens and sunblocks are suitable for use herein. See, U.S. Patent 5,087,445, Haffey et al, issued February 11 , 1992; U.S. Patent 5,073,372, Turner et al, issued December 17, 1991 , U S Patent 5,073,371 , Turner et al., issued December 17, 1991 , and Segaπn, et al, at Chapter VIII, pages 189 et seq., of Cosmetics Science and Technology (1972), which discloses numerous suitable sunscreens and sunblocks Preferred among those sunscreens and sunblocks which are useful in the compositions are those selected from 2-ethylhexyl-p-methoxycinnamate (commercially available as PARSOL MCX), butylmethoxydibenzoyl-methane, 2-hydroxy-4-methoxybenzo- phenone, 2-phenylbenzimidazole-5-sulfonic acid, octyldimethyl-p-aminobenzoic acid, octocrylene, 2-ethylhexyl N,N-dimethyl-p-amιnobenzoate, p-aminobenzoic acid, 2-phenylbenzimidazole-5-sulfonic acid, octocrylene, oxybenzone, homomenthyl salicylate, octyl salicylate, 4,4'-methoxy-f-butyldibenzoylmethane, 4-isopropyl dibenzoylmethane, 3-benzylidene camphor, 3-(4-methylbenzylιdene) camphor, titanium dioxide, zinc oxide, silica, iron oxide, Eusolex^{I M} 6300, Octocrylene, Parsol 1789, and mixtures thereof.

Also particularly useful in the compositions are sunscreens and sunblocks such as those disclosed in U.S. Patent 4,937,370, Sabatel , issued on June 26, 1990, and U.S. Patent 4,999,186, Sabatelli, issued on March 12, 1991 The sunscreens and sunblocks disclosed therein have, in a single molecule, two distinct chromophore moieties which exhibit different ultraviolet radiation absorption spectra. One of the chromophore moieties absorbs predominantly in the UVB radiation range and the other absorbs strongly in the UVA radiation range. These sunscreens and sunblocks provide higher efficacy, broader UV absorption, lower skin penetration and longer lasting efficacy relative to conventional sunscreens and sunblocks. Preferred sunscreens and sunblocks include those selected from butylmethoxydibenzoylmethane, 2-ethylhexyl-p- methoxycinnamate, phenyl benzimidazole sulfonic acid, octocrylene, 4-N,N-(2- ethylhexyl)methylaminobenzoic acid ester of 2,4-dihydroxybenzophenone, 4- N,N-(2-ethylhexyl)methylaminobenzoic acid ester with 4- hydroxydibenzoy I methane, 4-N,N- (2-ethylhexyl)methylaminobenzoic acid ester of 2-hydroxy-4-(2-hydroxyethoxy)benzophenone, 4-N,N-(2-ethylhexyl)- methylaminobenzoic acid ester of 4-(2-hydroxyethoxy)dιbenzoylmethane

A safe and effective amount of the sunscreens and sunblocks is used, typically from about 0.5% to about 20%, more typically from about 2% to about 10%. Exact amounts will vary depending upon the sunscreen chosen and the desired Sun Protection Factor (SPF). SPF is a commonly used measure of photoprotection of a sunscreen against erythema. See Federal Register, Vol 43, No. 166, pp. 38206-38269, August 25, 1978. A sunscreen or sunblock herein may also be added to improve the skin, particularly to enhance their resistance to being washed off by water, or rubbed off. Preferred sunscreens and sunblocks which will provide this benefit are a copolymer of ethylene and acrylic acid. Compositions comprising this copolymer are disclosed in U.S. Patent 4,663,157, Brock, issued May 5, 1987 2. Anti-Oxidants/Radical Scavengers Anti-oxidant/radical scavengers are especially useful for providing protection against UV radiation which can cause increased scaling or texture changes in the stratum corneum and against other environmental agents which can cause skin damage

A safe and effective amount of an anti-oxidant/radical scavenger may be added to the compositions of the subject invention, preferably from about 0 1 % to about 10%, more preferably from about 1 % to about 5 %

Anti-oxidants/radical scavengers such as ascorbic acid (vitamin C) and its salts, ascorbyl esters of fatty acids, ascorbic acid derivatives (/ e , magnesium ascorbyl phosphate), tocopherol (vitamin E), tocopherol sorbate, tocopherol acetate, other esters of tocopherol, butylated hydroxy benzoic acids and their salts, 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (commercially available under the tradename Trolox®), gallic acid and its alkyl esters, especially propyl gallate, uric acid and its salts and alkyl esters, sorbic acid and its salts, amines {i.e., N,N-diethylhydroxylamιne, amino-guanidine), sulfhydryl compounds {i.e., glutathione), dihydroxy fumanc acid and its salts, lycine pidolate, arginine pilolate, nordihydroguaiaretic acid, bioflavonoids, lysine, methionine, proline, superoxide dismutase, silymaπn, tea extracts, grape skin/seed extracts, melanin, and rosemary extracts may be used. Preferred anti- oxidants/radical scavengers are selected from tocopherol sorbate and other esters of tocopherol, more preferably tocopherol sorbate For example, the use of tocopherol sorbate in topical compositions and applicable to the present invention is described in U.S. Patent 4,847,071 , Bissett et al, issued on July 11 , 1989. 3. Anti-Inflammatory Agents Anti-inflammatory agents enhance the skin appearance benefits, by for example, contribution of uniformity and acceptable skin tone and/or color.

The composition of the present invention contains a safe and effective amount of the anti-inflammatory agent, preferably from about 0 1 % to about 10%, more preferably from about 0.5% to about 5%.

Preferably, the anti-inflammatory agent includes a steroidal anti- inflammatory agent and an non-steroidal anti-inflammatory agent. Preferred steroidal anti-inflammatory for use is hydrocortisone. The variety of compounds encompassed by this group are well-known to those skilled in the art. For detailed disclosure of the chemical structure, synthesis, side effects, etc. of non-steroidal anti-inflammatory agents, reference may be had to standard texts, including Anti-inflammatory and Anti-Rheumatic Drugs. K. D. Rainsford, Vol. Mil, CRC Press, Boca Raton, (1985), and Anti- inflammatory Agents, Chemistry and Pharmacology. 1 , R. A Scherrer, et al , Academic Press, New York (1974), each incorporated herein by reference

Specific non-steroidal anti-inflammatory agents useful in the composition invention include, but are not limited to:

(i) the oxicams, such as piroxicam, isoxicam, tenoxicam, sudoxicam, and CP-14,304;

(ii) the salicylates, such as aspirin, disalcid, benorylate, trilisate, safapryn, solprin, diflunisal, and fendosal;

(iii) the acetic acid derivatives, such as diclofenac, fenclofenac, indomethacin, sulindac, tolmetin, isoxepac, furofenac, tiopinac, zidometacin, acematacin, fentiazac, zomepirac, clindanac, oxepinac, felbinac, and ketorolac;

(iv) the fenamates, such as mefenamic, meclofenamic, flufenamic, niflumic, and tolfenamic acids;

(v) the propionic acid derivatives, such as ibuprofen, naproxen, benoxaprofen, flurbiprofen, ketoprofen, fenoprofen, fenbufen, indopropfen, pirprofen, carprofen, oxaprozin, pranoprofen, miroprofen, tioxaprofen, suprofen, alminoprofen, and tiaprofenic; and

(vi) the pyrazoles, such as phenylbutazone, oxyphenbutazone, feprazone, azapropazone, and trimethazone. Mixtures of these non-steroidal anti-inflammatory agents may also be employed, as well as the dermatologically acceptable salts and esters of these agents.

Finally, so-called "natural" anti-inflammatory agents are useful in methods of the present invention. Such agents may suitably be obtained as an extract by suitable physical and/or chemical isolation from natural sources (/ e , plants, fungi, by-products of microorganisms). For example, alpha bisabolol, aloe vera, Manjistha (extracted from plants in the genus Rubia. particularly Rubia Cordifolia), and Guggal (extracted from plants in the genus Commiphora, particularly Commiphora Mukul), kola extract, chamomile, and sea whip extract, may be used.

Additional anti-inflammatory agents useful herein include compounds of the Licorice (the plant genus/species Glvcyrrhiza qlabra) family, including glycyrrhetic acid, glycyrrhizic acid, and derivatives thereof (e g , salts and esters). Suitable salts of the foregoing compounds include metal and ammonium salts. Suitable esters include C2-24 saturated or unsaturated esters of the acids, preferably C-|o^_24_> ^more preferably Ci6^_24 Specific examples of the foregoing include oil soluble licorice extract, the glycyrrhizic and glycyrrhetic acids themselves, monoammonium glycyrrhizinate, monopotassium glycyrrhizinate, dipotassium glycyrrhizinate, 1-beta-glycyrrhetιc acid, stearyl glycyrrhetinate, and 3-stearyloxy-glycyrrhetinic acid, and disodium 3-succιnyloxy-beta- glycyrrhetinate. Stearyl glycyrrhetinate is preferred

4. Antimicrobial Agent For the purpose of the present invention, "antimicrobial agents" means a compound capable of destroying microbes, preventing the development of microbes or preventing the pathogenic action of microbes. Antimicrobal agents are useful, for example, in controlling acne Preferred antimicrobial agents useful in the present invention are benzoyl peroxide, erythromycin, tetracycline, clindamycin, azelaic acid, sulfur resorcinol phenoxyethanol, and Irgasan™ DP 300 (Ciba Geigy Corp , U S A ) A safe and effective amount of an antimicrobial agent may be added to compositions of the present invention, preferably from about 0.001 % to about 10%, more preferably from about 0.01 % to about 5%, still more preferably from about 0 05% to about 2%.

5. Chelators For the purpose of the present invention, "chelating agent" reacts for removing a metal ion from a system by forming a complex so that the metal ion cannot readily participate in or catalyze chemical reactions The inclusion of a chelating agent is especially useful for providing protection against UV radiation which can contribute to excessive scaling or skin texture changes and against other environmental agents which can cause skin damage A safe and effective amount of a chelating agent may be added to the compositions of the present invention, preferably from about 0 1 % to about 10% more preferably from about 1 % to about 5% Exemplary chelators that are useful herein are disclosed in U S Patent 5,487,884, Bissett et al, issued January 30 1996; PCT application 91/16035 and 91/16034, Bush et al, published October 31 , 1995. Preferred chelators are fuπldioxime and derivatives thereof 6 Other components

Other than the above optional components, the composition of the present invention include preservatives and preservative enhancers such as water- soluble or solubi zable preservatives including Germall 115, methyl, ethyl, propyl and butyl esters of hydroxybenzoic acid, benzyl alcohol, EDTA, Bronopol (2- bromo-2-nitropropane-1 ,3-diol) and phenoxypropanol, skin lightening/evenness agents including kojic acid, arbutin, ascorbic acid and derivatives thereof and described in PCT Application number U.S. 95/07432, Hillebrand, filed on June 12, 1995; WO95/23780, Kvalnes et al, published September 8, 1995, skin- conditioning agents; skin penetration enhancing agents, skin protectants, skin soothing agents; skin healing agents, ultraviolet light absorbers or scattering agents, sequestrants, anti-acne agents, anti-androgens, depilation agents keratolytic agents/ desquamation agents/ exfo ants such as salicylic acid panthenol moisturizer such as D-panthenol, soluble or colloidally-soluble moisturizing agents such as hyaluronic acid and starch-grafted sodium polyacrylates such as Sanwet™ IM-1000, IM-1500 and IM-2500 available from Celanese Superabsorbent Materials, Portsmith, VA, USA and described in US Patent 4,076,663; proteins and polypeptides and derivatives thereof organic hydroxy acids, vitamins and derivatives thereof such as vitamin A (e g retmoid which are commercially available from a number of sources, for example, Sigma Chemical Company (St. Louis, MO), and Boerhinger Mannheim (Indianapolis IN) and described in U.S Patent 4,677,120, Parish et al , issued Jun 30, 1987, U S Patent 4,885,311 , Parish et al , issued Dec 5, 1989, U S Patent 5,049,584, Purcell et al., issued Sep. 17, 1991 , U.S Patent 5,124,356, Purcell et al , issued Jun. 23, 1992; and Reissue Patent 34,075, Purcell et al , issued Sep 22 1992) vitamin B3 (e.g., nicotinic acid esters and derivatives of niacinamide, commercially available from a number of sources, for example, the Sigma Chemical Company (St. Louis, MO); ICN Biomedicals, Inc (Irvin, CA) and Aldπch Chemical Company (Milwaukee, Wl) and as described by W Wenner, "The Reaction of L-Ascorbic and D-lsoascorbic Acid with Nicotinic Acid and Its Amide", J. Organic Chemistry, Vol. 14, 22-26 (1949), vitamin C, vitamin E and vitamin K; drug astringents; external analgesics, film formers, absorbents including oil absorbents such as clays and polymeric absorbents, abrasives, anticaking agents; antifoaming agents, binders, biological additives, bulking agents; coloring agents; perfumes, essential oils, and solubilizers thereof, natural extracts; compounds which stimulate collagen production F. General Experimental Procedure

0.75 ml of the test materials is applied to 50 cm² of the depilated back of the guinea pig. The treated guinea pigs are exposed to 150 - 200 of female mosquitoes (Aedes aegypti) in a cage for a determined time (for example, 4 and 8 hours).

After the exposure, the number of mosquito biting sites is counted by a LDF (Laser Dopplar Flowmetry) using a template of acetate sheet having 20 holes (2 cm apart, covering approx. 50 cm²) as a site marker for measurement Measurements are before and after exposure at the specific sites and at the mosquito bite sites. The result is expressed as numbers of bites and the PU (arbitrary perfusion units). The PU value of untreated shaven guinea pig is used as control.

EXAMPLES

The following examples further describe and demonstrate embodiments within the scope of the present invention. The examples are given solely for the purpose of illustration and are not to be construed as limitations of the present invention, as many variations thereof are possible without departing from the spirit and scope of the invention. Where applicable, ingredients are identified by chemical or CTFA name, or otherwise defined below

The compositions shown below can be prepared by any conventional method known in the art. Suitable methods and formulations are as follows

Composition I - II Mist Type

1 Copolymer 958 : 50% ethanol solution of Poly(vιnylpyrro done/ dimethylaminomethyl methacrylate)

2PVPΛ/A S-630 Vinylpyrrohdone/vinyl acetate Copolymer ³ACA : 8-Acetoxycarvotanacetone

The composition I- II is mist made composition made by the following steps: (a) Mix Phase A ingredients until completely dissolved; (b) Separately, dissolve ACA of Phase B completely and add to the mixture of phase A while continuing to mix,

(c) Add water of Phase C to the batch mixture of phases A-B until uniform while continuing to mix; and (d) Mixing is continued until the resulted batch mixture is uniform Composition Clear Gel

⁴Carbopol 954 : Carbomer

The composition III is a Clear Gel made by the following steps.

(a) Mix Phase B ingredients until completely dissolved,

(b) Add Phase C ingredient to the mixture of Phase B until uniform while continuing to mix;

(c) Separately, dissolve ACA until a uniform solution of Phase A is achieved and add to the mixture of Phases B-C while continuing to mix, and

(d) Continue to mix until the batch mixture is uniform

Composition IV UV protect lotion

⁵ Arlacel 165 : Glyceryl Stearate and PEG-100 Stearate

The composition IV is a UV protect lotion made by the following steps

(a) Mix Phase A ingredients at a temperature of about 70-75°C,

(b) Separately, mix Phase B ingredients at a temperature of about 70-75°C until uniform and add to the mixture of Phase A to form a complete emulsion of Phase A-B; (c) Cool the batch mixture of A-B to about 60°C,

(d) Add Phase C ingredient to the batch mixture of phases A-B and mix until uniform;

(e) Separately, mix Phase D ingredients until uniform and add to the batch mixture of phases A-C at about 60°C while continuing to mix, (f) Cool the batch mixture of phases A-D to about 35°C, (g) Separately, mix Phase E ingredients until dissolved completely and add to the batch mixture of phases A-D and continue to cool to about 30°C and (h) Continue to mix until the resulting batch mixture is uniform

The embodiments disclosed and represented by the previous examples have many advantages. For example, compositions containing insect repellent active compounds can be safe to the skin and provide long lasting repellent efficacy. It is understood that the foregoing detailed description of examples and embodiments of the present invention are given merely by way of illustration, and that numerous modifications and variations may become apparent to those skilled in the art without departing from the spirit and scope of the invention; and such apparent modifications and variations are to be included in the scope of the appended claims.

Claims

What is claimed is:

1. A composition comprising:

(a) an active compound having the formula

(b) a water-soluble polymer; and

(c) a hydrophilic liquid carrier, wherein R¹ and R² are independently selected from saturated, straight or branched alkyl group of from 1 to about 10 carbons.

2. The composition of Claim 1 wherein R^"1 and R² are selected from saturated, straight or branched alkyl group of from 1 to about 3 carbons

3. The composition of Claim 2 wherein the water-soluble polymer is selected from the group consisting of a carbonic acid polymer, a polysaccande, and a gum.

4. The composition of Claim 3 wherein the hydrophilic liquid carrier comprises a polyhydric alcohol and water

5. The composition of Claim 4 wherein the composition further comprises a emulsifying agent selected from the group consisting of a hydrophobic component, a surfactant, and mixtures thereof

6. The composition of Claim 5 wherein the composition further comprises optional components selected from the group consisting of sunscreens or sunblocks, anti-oxidant/radical scavenger, anti-inflammatory agents, antimicrobial agents, chelating agents, and mixtures thereof

7. A skin care composition according to the composition of Claim 1 A method for making composition comprising the steps of: (a) adding an active compound having the formula

wherein Rl and R² are independently selected from saturated, straight or branched alkyl group of from 1 to about 10 carbons, to a hydrophilic liquid carrier to make a first mixture;

(b) adding a water-soluble polymer to water to make a second mixture and

(c) mixing the first and second mixtures to form the composition.