Cosmetic composition with improved color stability of retinoic acid precursors

Abstract

The present invention relates to a cosmetic composition comprising a functionalized heteroaromatic compound and a retinoic acid precursor. There is a need for an effective method for stabilizing the color stability of a composition comprising a functionalized heteroaromatic compound and a retinoic acid precursor. It has been found that a functionalized heteroaromatic compound and a retinoic acid precursor, in combination with a compatible oil, improves the color stability of the retinoic acid precursor. Thus, the present invention relates to a composition comprising a synergistic combination of a compatible oil with a functionalized heteroaromatic compound and a retinoic acid precursor.

Description

[Technical Field]

[0001] The present invention is in the field of personal care compositions, particularly skin benefit compositions for topical application to human skin. More particularly, the present invention relates to cosmetic compositions containing a retinoic acid precursor in combination with a compatible oil and a functionalized heteroaromatic compound to improve the color stability of the composition. [Background technology]

[0002] Human skin is subject to deterioration due to environmental factors (wind, dry air, sun exposure, pollution, blue light), dermatological conditions, and the normal aging process (chronoaging). Skin damage leads to the development of facial fine lines, wrinkles, yellowing or sallowness, sagging, dehydration, hyperpigmentation, age spots, and other general signs of aging. However, the standard definition of ideal skin currently includes young skin with an even tone and smooth texture. Therefore, there is a great demand for "anti-aging" or "pre-aging" cosmetics that reverse, treat, or delay the visible signs of damaged skin.

[0003] The cosmetic composition containing retinoic acid precursor such as retinol has become very prominent in recent years.Retinol, also known as vitamin A, and many of its ester derivatives and retinoid family members, including retinyl propionate, can be effective in addressing the visible signs of aging skin mentioned above, among other advantages, when applied topically.Despite the advantages of retinoid, when retinoic acid precursor is included in cosmetic composition, the stability of the composition is often difficult.

[0004] Furthermore, many people often turn to cosmetics with whitening effect to achieve the desired even skin.In the industry, there is a constant need for cosmetic whitening agents with enhanced efficacy and stability.Without intending to be bound or limited by theory, it is believed that compositions containing functionalized heteroaromatic compounds, particularly niacinamide and / or nicotinate, are useful for promoting even skin and skin hydration, while reducing the appearance of skin dullness and fine lines, among other benefits.Further examples of whitening agents that can be used for topical application to the skin include resorcinols such as hexylresorcinol, hydroquinone, arbutin and kojic acid.

[0005] However, it can be difficult to obtain a color-stable cosmetic composition containing a retinoic acid precursor. Color instability is a concern because consumers are sensitive to changes in the color appearance of the cosmetic composition they use, especially if they believe that color changes signal a decrease in chemical effectiveness. The color instability of a retinoic acid precursor is nonlinearly positively correlated with the chemical instability of the retinoic acid precursor, but not proportionally or exponentially. The color stability of a composition containing a retinoic acid precursor tends to deteriorate in a shorter time than chemical activity. Trace chemical degradation of a retinoic acid precursor due to exogenous factors, including impurities in the formulation and interactions with other ingredients such as niacinamide, can result in severe color degradation. Therefore, cosmetic compositions that desire to contain both a retinoic acid precursor and a functionalized heteroaromatic compound may experience significant color degradation.

[0006] Therefore, the present inventors have recognized a need to develop cosmetic compositions with improved color stability comprising a retinoic acid precursor and a functionalized heteroaromatic compound. It is therefore an object of the present invention to provide stable cosmetic compositions having a retinoic acid precursor and a compatible oil in combination with a functionalized heteroaromatic compound.

[0007] Additional Information An approach is disclosed for incorporating retinoic acid precursors into functionalized heteroaromatic compounds in the presence of a compatible oil.

[0008] U.S. Pat. Nos. 5,997,890 and 6,001,377 disclose topical compositions useful for providing immediate improvement in skin appearance, including granular materials and active agents for regulating skin condition, preferred options including vitamin B3 compounds and retinoids.

[0009] U.S. Patent Nos. 5,933,998, 5,939,082, 6,150,403, 6,238,678, and 6,217,888 disclose topical compositions for controlling the oily and / or shiny appearance of skin, preferred embodiments of which include a retinoid and a vitamin B3 compound.

[0010] US Patent Nos. 6,224,888 and 6,528,071 relate to cosmetic compositions containing a vitamin B3 compound, an oily liquid emollient, a polar solvent, a solidifying agent, and a colorant.

[0011] US Patent No. 6,183,761 reports a topical composition for regulating skin appearance having a vitamin B3 compound, a polycyclic compound, and an acceptable carrier.

[0012] PCT Application WO 94 / 09756 relates to a composition for topical application to human skin to promote repair of photodamaged skin, comprising retinol or a derivative thereof and a selected skin lightening agent.

[0013] PCT Application WO 98 / 52536 reports skin care compositions with improved skin compatibility containing a retinoid and a preservative ingredient.

[0014] PCT Application WO 99 / 47115 describes skin care compositions containing vitamin B3 compounds and improved carrier systems.

[0015] None of the above additional information describes the specific combination of retinoic acid, a functionalized heteroaromatic compound, and a compatible oil to achieve a cosmetic composition with improved color stability used for anti-aging or pre-aging and skin lightening benefits, as disclosed in the presently claimed invention. [Prior art documents] [Patent documents]

[0016] [Patent Document 1] U.S. Patent No. 5,997,890 [Patent Document 2] U.S. Patent No. 6,001,377 [Patent Document 3] U.S. Patent No. 5,933,998 [Patent Document 4] U.S. Patent No. 5,939,082 [Patent Document 5] U.S. Patent No. 6,150,403 [Patent Document 6] U.S. Patent No. 6,238,678 [Patent Document 7] U.S. Patent No. 6,217,888 [Patent Document 8] U.S. Patent No. 6,224,888 [Patent Document 9] U.S. Patent No. 6,528,071 [Patent Document 10] U.S. Patent No. 6,183,761 [Patent Document 11] International Publication No. 94 / 09756 [Patent Document 12] International Publication No. 98 / 52536 [Patent Document 13] International Publication No. 99 / 47115 Summary of the Invention

[0017] The present inventors have shown that the use of a retinoic acid precursor, as well as a functionalized heteroaromatic compound with a compatible oil, enhances the color stability of compositions formulated with the retinoic acid precursor.

[0018] Thus, in a first aspect, the present invention relates to a cosmetic composition comprising a retinoic acid precursor, a functionalized heteroaromatic compound, and a compatible oil, which surprisingly improves the color stability of the composition.

[0019] In a second aspect, the present invention relates to a method of treating skin in need of treatment, comprising the step of topically applying a cosmetic composition onto the skin in need of treatment.

[0020] Cosmetic compositions prepared in accordance with the present invention have unexpectedly been discovered to provide good stability, color stability, anti-aging and whitening benefits.

[0021] All other aspects of the present invention will become more readily apparent in light of the following detailed description and examples.

[0022] For the avoidance of doubt, the term "comprising" is meant to encompass unspecified elements, whether functionally significant or non-critical, without limitation to any stated elements. Thus, the listed steps, elements, or options need not be exhaustive. Whenever the words "including" or "having" are used, these terms are meant to be equivalent to "comprising" as defined above.

[0023] As used herein, the term "skin" includes the skin of the face, neck, chest, back, arms, armpits, buttocks, hands, legs, and scalp. As used herein, a skin benefit agent means (a) improving a facial or body characteristic after topical application, such as skin properties, (b) providing a benefit thereto, or (c) including both (a) and (b) ingredients. Personal care compositions are compositions for topical application and include lotions, creams, gels, serums, pump or aerosol sprays, balms, deodorants, antiperspirants, nail treatments, cleansing compositions, and makeup. In a particularly preferred embodiment, the compositions of the present invention are leave-on compositions, and the skin benefit agent is a retinoic acid precursor compound. As used herein, the terms "retinoid" and "retinoic acid precursor" refer to all natural and / or synthetic analogs of vitamin A or its derivatives that have biological activity similar to that of vitamin A in human skin. The term "derivative(s)" used with respect to an ingredient herein refers to functional group substitutions on the compound. As used herein, the term "functionalized" means that the compound has at least one functional group substituent on the compound, including acyl, hydroxy, alkoxy, carboxamido (amide), carboxyl, or carboalkoxy (ester) substituents. "HLB" stands for hydrophilic-lipophilic balance of a surfactant and is used to measure the degree to which a surfactant is hydrophilic or lipophilic and is widely used in the art. As used herein, color-stable refers to a cosmetic composition having a ΔE of 10 or less based on the L*, a*, and b* color differences based on the CIELAB color space model obtained with a Hunter Lab spectrophotometer. Generally, a ΔE of 10 or less is acceptable, a ΔE between 10 and 20 is negotiable, and a ΔE of >20 is unacceptable. For b* values, the value represents the blue-yellow component of the object's color, with negative (-) values ​​representing a shift toward the blue space and positive (+) values ​​representing a shift toward the yellow space. A b* value of 0 represents a true neutral gray value. As used herein, the term "compatible" refers to oils having a Hansen Total Solubility Parameter value within the range of 13 to 26. The Hansen Total Solubility Parameter is the sum of the three Hansen parameters, namely, δ d(defines the energy from dispersion forces between molecules), δ p (defines the energy from dipole-dipole intermolecular forces between molecules), and δ h (which defines the energy from hydrogen bonds between molecules) is determined based on δ d The values ​​are obtained according to the CRC Handbook of Solubility Parameters and other Cohesion Parameters, Second Edition by Allan FM Barton.

[0024] Except in the examples, or where expressly stated otherwise, all numbers herein indicating amounts of ingredients may be understood to be modified by the word "about." All amounts are by total weight of the composition unless otherwise specified. DETAILED DESCRIPTION OF THE INVENTION

[0025] The compositions of the present invention contain a retinoic acid precursor, which typically comprises a retinyl ester, retinol, retinal or a mixture thereof, preferably retinal, a retinyl ester or a mixture thereof. Examples of retinyl esters suitable for use in the present invention include, but are not limited to, retinyl palmitate, retinyl formate, retinyl acetate, retinyl propionate, retinyl butyrate, retinyl valerate, retinyl isovalerate, retinyl hexanoate, retinyl heptanoate, retinyl octanoate, retinyl nonanoate, retinyl decanoate, retinyl undecanoate, retinyl taurate, retinyl tridecanoate, retinyl myristate, retinyl pentadecanoate, retinyl heptadecanoate, retinyl stearate, retinyl isostearate, retinyl nonadecanoate, retinyl arachidonate, retinyl behenate, retinyl linoleate, and retinyl oleate.Preferred esters for use in the present invention are selected from retinyl palmitate, retinyl acetate, retinyl propionate, and mixtures thereof. Also preferred are retinyl linoleate and retinyl oleate. In a particularly preferred embodiment, the retinoic acid precursor is retinyl propionate. The retinoic acid precursor is used in the compositions of the present invention in an amount of 0.001 to 10%, preferably 0.01 to 1%, and most preferably 0.01 to 0.5% by weight of the cosmetic composition.

[0026] It is often desirable to include a functionalized heteroaromatic compound in cosmetic compositions containing retinoic acid precursors based on skin benefits. However, it has been discovered that further combining a composition containing a retinoic acid precursor with a functionalized heteroaromatic compound exacerbates the color instability of the retinoic acid precursor, manifesting as a deeper yellow discoloration of the composition—a challenge that the present invention may help to overcome. The cosmetic compositions of the present invention include a functionalized heteroaromatic compound in addition to the retinoic acid precursor. The functionalized heteroaromatic compound is preferably a carboxylic acid-functionalized heteroaromatic compound. The carboxylic acid-functionalized heteroaromatic compound may be any cosmetically acceptable nicotinic acid, picolinic acid, or a derivative or mixture thereof, preferably nicotinic acid, niacinamide, nicotinate, picolinic acid, picolinamide, or a mixture thereof, more preferably niacinamide, picolinamide, or a mixture thereof. The amount of the functionalized heteroaromatic compound is typically about 0.01-10%, preferably about 0.05-7%, more preferably about 0.1-5% (by weight) of the cosmetic composition.

[0027] It has now been unexpectedly discovered that the use of a compatible oil in a composition comprising a retinoic acid precursor and a functionalized heteroaromatic compound can contribute to improved color stability when compared to a control in the same vehicle. The Hansen total solubility parameter (δ d Oils having a δ saturation value in the range of 13 to 26, preferably 15 to 25, are most compatible and therefore suitable for use in such cosmetic compositions. Illustrative examples of oils suitable for use in the present invention include isopropyl myristate (δ d =17.5), caprylic / capric triglyceride (δ d =18.9), isopropyl palmitate (δ d =17.2), benzyl alcohol (δ d=24.7). Illustrative, but non-limiting, examples are sunflower seed oil, cotton oil, canola oil, grape seed oil, soybean oil, castor oil, borage oil, olive oil, jojoba oil, and mixtures thereof. Mono- and diglycerides may also be useful. Illustrative of these categories are glyceryl monostearate and glyceryl distearate. Compatible oils are used in the compositions of the present invention in amounts of 13-30%, preferably 14-28%, and most preferably 15-25% by weight of the composition.

[0028] Color stability is determined using a LabScan XE instrument (Hunter Associates Laboratory, Inc., Reston, Virginia). The LabScan XE measures color data. Samples at different storage stages contained in vials or measurement cells are loaded into the LabScan XE measurement port. According to the measurement procedure specified in the associated instrument menu and computer software, color (a*, b*, and L*) is measured and calculated to obtain color change data (ΔE) values. b* is a scale in the blue-yellow space based on the CIELAB color space model, where an increase in the b* value indicates an increase in the yellow component and a decrease in the b* value indicates an increase in the blue component.

[0029] It has also been unexpectedly discovered that compositions made in accordance with the present invention provide good stability and color stability of the composition itself, as well as anti-aging and whitening benefits when applied to the skin.

[0030] The cosmetic composition of the present invention may also contain a cosmetically acceptable vehicle to act as a diluent, dispersant, or carrier for the skin benefit agent in the composition to facilitate its distribution when the composition is applied to the skin. This cosmetically acceptable vehicle may be aqueous, anhydrous, or emulsion. An oily carrier in the presence of water and an emulsifier forms an emulsified system as a carrier. Preferably, the composition is aqueous or emulsion, particularly a water-in-oil or oil-in-water emulsion, preferentially an oil-in-water emulsion. The cosmetic composition is usually in the form of, but not limited to, a cream or lotion.

[0031] Suitable carriers for use in the present invention include water, seawater, rosewater (e.g., Rose Damascena flower water), tea (e.g., Camellia Sinensis leaf water), Aloe Barbadensis (Aloe Vera) leaf juice, witch hazel (e.g., Hamamelis Virginiana extract), lavender water (e.g., Lavendula Angustifolia flower water), and grape water (e.g., Vitis Vinifera fruit water and Vitis Vinifera juice). In a most preferred embodiment, water is the carrier. The amount of water may range, preferably, from 5 to 85%, more preferably from 15 to 75%, and most preferably from 30 to 70%, by weight of the cosmetic composition, including all ranges subsumed therein. The cosmetically acceptable vehicle can form the balance of the composition in the absence of other cosmetic adjuvants. In addition to water, suitable carrier classes include, but are not limited to, silicones, polyhydric alcohols, fatty acids, hydrocarbons, triglycerides, waxes, and thickeners.

[0032] It is within the scope of the present invention to include silicones, which can be classified as volatile or non-volatile. The amount can range, for example, from 0.01 to 25%, more preferably from 0.1 to 20% (by weight) of the cosmetic composition. In one embodiment of the present invention, 0.01 to 2% (by weight) of silicone is included in the composition without significantly affecting the sensory properties. As used herein, the term "volatile" refers to a material that has a measurable vapor pressure at ambient temperature. Volatile silicone oils are preferably selected from cyclic (cyclomethicone) or linear polydimethylsiloxanes containing 3 to 9, preferably 4 to 5, silicon atoms.

[0033] Nonvolatile silicones useful in the composition include polyalkyl siloxanes, polyalkylaryl siloxanes, and polyether siloxane copolymers. Essentially nonvolatile polyalkyl siloxanes useful herein include, for example, polyalkyl siloxanes having a viscosity of about 5×10 at 25° C. -6 From 0.1m 2 Polydimethylsiloxanes having a viscosity of 1 / s are also suitable for use in the cosmetic compositions of the present invention. Emulsifying and non-emulsifying silicone elastomers are also suitable for use in the cosmetic compositions of the present invention.

[0034] Conventional humectants, generally polyhydric alcohol-type materials, can be used in the present invention. Typical polyhydric alcohols include glycerol (i.e., glycerine or glycerin), propylene glycol, dipropylene glycol, polypropylene glycol, polyethylene glycol, sorbitol, hydroxypropyl sorbitol, hexylene glycol, 1,3-butylene glycol, isoprene glycol, 1,2,6-hexanetriol, ethoxylated glycerol, propoxylated glycerol, and mixtures thereof. Glycerin, propylene glycol, or mixtures thereof are most preferred. The amount of humectant used can range from 0.1 to 25%, preferably from 0.5 to 20%, and more preferably from 1 to 15% by weight of the cosmetic composition.

[0035] Retinoid boosters can also be useful ingredients, such as fatty acids and their derivatives, to incorporate for use in the compositions of the present invention. As described in several U.S. patents to Granger et al. (U.S. Pat. Nos. 5,759,556, 5,756,109, 5,747,051, 5,716,627, 5,811,110, 5,536,740, 5,747,051, 5,599,548, 5,955,092, 5,885,595, 5,759,556, 5,693,330, 7,959,913, 8,226,933, and 8,409,550), the term "retinoid booster" is used collectively to refer to compounds that have been shown to enhance the enzymatic conversion of retinyl esters and retinol to retinoic acid as part of the natural retinol metabolic process in the epidermis of the skin. Boosters, alone or in combination with other booster compounds, serve to enhance the effectiveness of retinoic acid precursors. The term "fat" refers to carbon chain lengths ranging from 10 to 30 carbon atoms. Illustrative of this category are pelargonic acid, lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, hydroxystearic acid, oleic acid, linoleic acid, ricinoleic acid, arachidic acid, behenic acid, erucic acid, and combinations thereof.Preferred derivatives of such fatty acids include fatty alcohols such as cetyl, lauryl, myristyl, palmitic, cetearyl, stearyl, and oleyl alcohol; fatty esters such as 2-ethyl-hexyl myristate, isopropyl stearate and isostearyl palmitate, triisopropyl trilinoleate and trilauryl citrate, lauryl palmitate, myristyl lactate, oleyl eurcate, and stearyl oleate, coco-caprylate / caprate (a blend of coco-caprylate and coco-caprate), propylene glycol myristyl ether acetate, diisopropyl adipate, and cetyl octanoate; and fatty amides such as cocamide monoethanolamide (CMEA), castor oil monoethanolamide, linoleoyl monoethanolamide (LAMEA), palmitamide monoethanolamide, and linoleamide diethanolamide. Other illustrative, but non-limiting, examples of such booster compounds include carotenoids, flavonoids, cyclic and acyclic fragrances, antifungals (e.g., bifonazole, climbazole, clotrimazole, econazole, ketoconazole, miconazole), phospholipid analogs, urea, phosphatiylethanolamine, phosphatidylcholine, sphingomyelin, natural dyes (e.g., coumarin), quinolines, isoquinolines, metyrapone, and mixtures thereof. In one embodiment of the present invention, a fatty acid, a fatty alcohol, a fatty amide, climbazole, or a mixture thereof can be used as a retinoid booster. In a particularly preferred embodiment of the present invention, 12-hydroxystearic acid, cetyl alcohol, cetearyl alcohol, CMEA, LAMEA, climbazole, or a mixture thereof is used as a retinoid booster. When used, 0.01 to 5% by weight of the retinoid booster compound is present in the composition.

[0036] Waxes and wax esters are also suitable for use in the compositions of the present invention. These waxes include animal-derived waxes or animal by-products (e.g., beeswax, spermaceti, China wax, wool wax, shellac wax), plant-derived waxes (e.g., tribehenin wax, carnauba wax, candelilla wax, bayberry wax, jojoba wax, orange wax, rice bran wax, sunflower wax, castor wax, soy wax), mineral waxes (e.g., montan wax, ceresin wax, ozokerite), and synthetic derivatives of natural waxes. The amount of wax or wax ester used can range from 0.01 to 10%, preferably 0.1 to 8% (by weight) of the composition.

[0037] Hydrocarbons may be included in the cosmetic compositions of the present invention. Suitable hydrocarbons may include mineral oil, petrolatum, and polyalphaolefins. Preferred examples of volatile hydrocarbons include polydecanes such as isodecane and isododecane, and C7-C8 to C8 olefins. 12 -C 15 Isoparaffins are included.

[0038] Cosmetic compositions prepared according to the present invention may contain one or more thickeners in an amount of 0.05 to 10%, preferably 0.1 to 5%, and more preferably 0.25 to 4% (by weight) of the composition. Useful thickeners include starch, natural and synthetic gums, and polysaccharides, including cellulose. Suitable starches include tapioca starch, corn starch, potato starch, aluminum starch octenyl succinate, and sodium hydroxypropyl starch phosphate. Suitable gums include xanthan, sclerotium, pectin, karaya, arabic, agar, guar, carrageenan, alginate, and combinations thereof. Suitable cellulose-based materials include hydroxypropyl cellulose, hydroxypropyl methylcellulose, ethyl cellulose, and sodium carboxymethylcellulose. Synthetic polymers that function as thickeners, such as polyacrylamide, carbomer, and taurate copolymers, are also suitable for use.

[0039] An emulsifier is preferably present in the cosmetic composition of the present invention. Emulsifiers suitable for use in the present invention have an HLB of 2.5 to 17. When an oil-continuous emulsion is desired, the emulsifier used has an HLB of 2.5 to 7.5, preferably 3 to 6.5, and most preferably 3 to 6, including all ranges subsumed therein. When a water-continuous emulsion is desired, the emulsifier used has an HLB of 8 to 17, preferably 8.5 to 15, and most preferably 9 to 14, including all ranges subsumed therein.

[0040] The total concentration of the emulsifier ranges from 0.1 to 20%, preferably 1 to 10%, and most preferably 1 to 8% (by weight) of the composition, including all ranges subsumed therein. The emulsifier may be selected from the group consisting of anionic, nonionic, cationic, and amphoteric surfactants. Particularly preferred nonionic surfactants are C6 condensed with about 2 to about 100 moles of ethylene oxide or propylene oxide per mole of hydrophobe. 10 -C 20 With fatty alcohol or acid hydrophobe; C2-C condensed with 2 to 20 moles of alkylene oxide 10 Alkylphenols; Mono- and di-fatty acid esters of ethylene glycol; Fatty acid monoglycerides; Sorbitan, mono- and di-C8-C 20 Suitable nonionic emulsifiers include fatty acids; polyoxyethylene sorbitan, and combinations thereof. Alkyl polyglycosides and saccharide fatty amides (e.g., methyl gluconamide) are also suitable nonionic emulsifiers. Still other suitable nonionic surfactants include glyceryl stearate, glycol stearate, and stearamide AMP.

[0041] Preferred anionic emulsifiers include alkyl ether sulfates and sulfonates, alkyl sulfates and sulfonates, alkyl benzene sulfonates, alkyl and dialkyl sulfosuccinates, C8-C 20 Acyl isethionates, C8-C 20 Acylmethyl isethionate, C8-C 20Acylmethyl taurate, C8-C 20 Included are alkyl ether phosphates, alkyl ether carboxylates, and combinations thereof.

[0042] Cationic emulsifiers that can be used include, for example, palmitamidopropyltrimonium chloride, distearyldimonium chloride, diester quaternary ammonium compounds (such as distearoylethyldimonium chloride), and mixtures thereof.

[0043] Useful amphoteric emulsifiers include cocoamidopropyl betaine, C 12 -C 20 Mention may be made of trialkylbetaines, sodium lauroamphoacetate and sodium laurodiamphoeacetate or mixtures thereof.

[0044] Fragrances, fixatives, abrasives, and additional skin benefit agents may optionally be included in the cosmetic compositions of the present invention. Skin benefit agents suitable for use in the present invention are meant to include, but are not limited to, opacifiers, colorants, moisturizers, emollients, occlusive agents, botanical extracts, optical agents, skin lightening agents, anti-inflammatory agents, anti-acne agents, antioxidants, sunscreens, light stabilizers, surfactants, wrinkle reducers, coloring agents, desquamation promoters, exfoliants, mixtures thereof, and the like. Each of these materials may range from 0.05 to 5%, preferably 0.1 to 3% (by weight).

[0045] The cosmetic compositions of the present invention may contain additional vitamins as desired skin benefit agents. Exemplary vitamins are vitamin B2, vitamin B5 (panthenol), vitamin B6, vitamin C, vitamin E, folic acid, and biotin. Vitamin derivatives may also be used. For example, vitamin C derivatives include ascorbyl tetraisopalmitate, magnesium ascorbyl phosphate, and ascorbyl glycoside. Vitamin E derivatives include tocopheryl acetate, tocopheryl palmitate, and tocopheryl linoleate. When present in a cosmetic composition according to the present invention, the total amount of additional vitamins may range from 0.01 to 10%, preferably 0.05 to 7%, and optimally 0.1 to 5% by weight of the cosmetic composition.

[0046] Other additional optional skin benefit agents suitable for use in the compositions of the present invention include minerals and skin nutrients, such as milk; magnesium, calcium, copper, zinc and other metallic components; alpha-hydroxy acids, beta-hydroxy acids, such as salicylic acid and its derivatives (such as 5-octanoylsalicylic acid, heptyloxy-4-salicylic acid, 4-methoxysalicylic acid, etc.); kojic acid; hydroquinone and arbutin; resveratrol; sugar isomers; undecylenoylphenylalanine; resorcinol derivatives (particularly 4-ethylresorcinol, 4-isopropylresorcinol, 4-isopropylresorcinol, 4-isopropylsalicylic acid ... 4-substituted resorcinol derivatives, including 4-hexylresorcinol, 4-cyclopentylresorcinol, 4-cyclohexylresorcinol, and their acylated forms; ceramides (e.g., ceramide 1, ceramide 3, ceramide 3B, and ceramide 6) and pseudoceramides; allantoin; pyroglutamic acid (PCA) salt derivatives, including zinc PCA and sodium PCA; and skin benefit acids and their derivatives (12-hydroxystearic acid; petroselinic acid; conjugated linoleic acid; octadecanoic acid; hyaluronic acid and its salt derivatives); mixtures thereof, and the like. When used, such skin benefit agents may comprise, in total, 0.001 to 12% (by weight) of the cosmetic composition.

[0047] A wide variety of plant extracts may be included in the cosmetic compositions of the present invention. The extracts may be soluble in water or oil and carried in a hydrophilic or hydrophobic solvent, respectively. In preferred embodiments, water or ethanol is the extraction solvent. Illustrative examples include extracts from green tea, yarrow, chamomile, licorice, aloe vera, Satsuma mandarin, willow bark, alfalfa, algae, grape seed, witch hazel, sage, thyme, and rosemary, as well as oils derived from sea buckthorn, moringa, argan, avocado, calendula, algae, and marula. Soybean extracts may also be used, particularly when retinol is desired. When used, such extracts are preferably used in a total amount ranging from 0.001 to 12% (by weight) of the cosmetic composition.

[0048] It is within the scope of the present invention that sunscreens and light stabilizers may be included. Sunscreens and light stabilizers that can be used in the compositions of the present invention include materials such as octyl methoxycinnamate (OMK), ethylhexyl salicylate, phenylbenzimidazole sulfonic acid (ensulizole), ethylhexyl p-methoxycinnamate available as Parsol MCX®, avobenzone (butyl methoxydibenzoylmethane) available as Parsol 1789®, and benzophenone-3, also known as oxybenzone. Inorganic sunscreen actives such as finely divided titanium dioxide (preferably having a particle size of less than 150 nm, most preferably less than 100 nm) may also be used, zinc oxide may also be used, and polyethylene and various other polymers are also suitable sunscreens. Other suitable sunscreens include p-aminobenzoic acid (PABA), octyldimethyl-PABA, 2-ethoxyethyl p-methoxycinnamate, benzophenone-1, benzophenone-2, benzophenone-6, benzophenone-8, benzophenone-9, benzophenone-12, homomethyl salicylate, menthyl anthranilate, benzophenone-4, triethanolamine salicylate, terephthalylidene dicamphorsulfonic acid, bisoctriazole, bisethylhexyloxyphenol methoxyphenyl triazine, bisdisulizole disodium, geometricazole trisiloxane, octyl triazone, iscotridinol, polysilicone-15, isopentenyl-4-methoxycinnamate, mixtures thereof, and the like. Octocrylene is also suitable for use. Amounts of sunscreens or light stabilizers when present may generally range from 0.1 to 20%, preferably from 0.5 to 15%, optimally from 0.75 to 10% by weight of the cosmetic composition.

[0049] The cosmetic compositions of the present invention may also contain natural and synthetic antioxidants. Illustrative, non-limiting examples of antioxidants for use in the compositions include butylated hydroxytoluene (BHT), dilauryl thiodipropionate, pentaerythrityl tetradi-t-butylhydroxyhydrocinnamate, and polyphenols. When used in the present invention, the total weight percent of the antioxidants is preferably 0.01-4%, more preferably 0.02-3%, and most preferably 0.05-2%.

[0050] Another optional additive suitable for use includes hemp oil containing 2.5 to 25% (by weight) cannabigerol and / or 0.5 to 10% (by weight) cannabidiol. When used, such oils will comprise 0.0001 to 12% (by weight) of the composition, preferably 0.01 to 5% (by weight) of the cosmetic composition, including all ranges subsumed therein.

[0051] One or more colorants may also be included in the cosmetic compositions of the present invention. Colorants include dyes or pigments of natural or synthetic origin. The dyes selected for use can be organic or inorganic and water-soluble or oil-soluble. Non-limiting examples of water-soluble dyes include, for example, D&C Yellow 8, D&C Yellow 10, D&C Orange 4, D&C Red 6, D&C Red 22, D&C Red 28, D&C Red 33, D&C Green 5, or methylene blue. Oil-soluble dyes include, for example, D&C Red 17, D&C Green 6, β-carotene, D&C Violet 2, D&C Yellow 11, D&C Orange 5, and quinoline yellow. Pigments suitable for use are particularly selected from mineral pigments, organic pigments, lakes, and mixtures thereof known in the art.Illustrative, but non-limiting, examples include mineral pigments such as titanium dioxide, ochre (yellow ochre, red ochre, brown ochre, iron hydroxide), metal oxides (zinc oxide, zirconium oxide, iron oxide, cerium oxide, chromium oxide), manganese violet, ultramarine, chromium hydrate, and ferric blue, or metal powders (aluminum, bronze, or copper powder); organic pigments such as nitroso, nitro, azo, phthalocyanine, diazine, xanthene, pyrene, quinoline, anthraquinone, triphenylmethane, fluoran, quinacridone, metal complexes, isoindolinone, isoindoline, perinone, perylene, diketopyrrolopyrrole, indigo, thioindigo, dioxazine, triphenylmethane, and quinophthalone compounds; and lakes (especially those derived from calcium, barium, aluminum, and strontium salts), such as D&C Red No. 6 Barium Lake, D&C Red No. 7 Calcium Lake, D&C Red Examples of suitable colorants include D&C No. 27 Aluminum Lake, D&C Red No. 28 Aluminum Lake, D&C Red No. 33 Aluminum Lake, FD&C Red No. 40 Aluminum Lake, FD&C Yellow No. 5 Aluminum Lake, FD&C Yellow No. 6 Aluminum Lake, D&C Yellow No. 10 Aluminum Lake, D&C Orange No. 5 Aluminum Lake, and FD&C Blue No. 1 Aluminum Lake. Nacreous materials, such as natural mica coated with metal oxides, bismuth oxychloride, or natural pigments, are also suitable for inclusion in the cosmetic compositions of the present invention. Other suitable colorants include chalk, activated charcoal, and carbon black. When used, the cosmetic composition contains 0.01 to 20%, preferably 0.1 to 15%, and more preferably 0.5 to 10% of the colorant by weight of the cosmetic composition.

[0052] Traditional buffers or pH adjusters are also suitable for inclusion in the cosmetic compositions of the present invention. These include common additives such as sodium hydroxide, potassium hydroxide, hydrochloric acid, citric acid, triethanolamine, and aminomethylpropanol. In a preferred embodiment, the pH of the cosmetic compositions of the present invention is 4 to 8, more preferably 4.25 to 7.75, and most preferably 5 to 7.5. The viscosity of the cosmetic compositions of the present invention can be measured at 25°C and a shear rate of 1 s using a strain-controlled parallel plate rheometer commercially available from suppliers such as TA Instruments under the name Discovery. -1 When measured under these conditions, the viscosity is about 1,000 to about 200,000 cps, preferably about 5,000 to about 180,000 cps, and most preferably about 10,000 to about 150,000 cps. Alternatively, the viscosity can be measured using a Brookfield viscometer (speed 20 rpm, spindle 5, helix path off, 25°C for 1 minute). The cosmetic composition of the present invention can be formulated as a lotion having a viscosity of 4,000 to 10,000 mPas, a fluid cream having a viscosity of 10,000 to 20,000 mPas, or a cream having a viscosity of 20,000 to 200,000 mPas or more.

[0053] Preservatives can be incorporated into the compositions of the present invention, if desired, to protect against the growth of potentially harmful microorganisms. Cosmetic chemists are familiar with appropriate preservatives and routinely select them to meet preservative and product stability testing requirements. Preservative systems should be selected taking into consideration the use of the composition and potential incompatibilities between the preservative and other ingredients in the formulation. Illustrative examples of preservatives for the compositions of the present invention include, but are not limited to, iodopropynyl butylcarbamate (IPBC), phenoxyethanol, ethylhexylglycerin, 1,2-octanediol, methylparaben, propylparaben, imidazolidinyl urea, sodium dehydroacetate, propanediol, alkyl esters of parahydroxybenzoic acid, sodium benzoate, benzoic acid, hydroxyacetophenone, DMDM ​​hydantoin derivatives, propionate salts, and various quaternary ammonium compounds. Preservatives are preferably used in amounts ranging from 0.01 to 2% of the composition, including all ranges encompassed therein.

[0054] To prepare the cosmetic compositions of the present invention, the desired ingredients are mixed by conventional methods, in any order, under moderate shear conditions at about 22°C to about 85°C and atmospheric pressure.

[0055] The cosmetic composition of the present invention is a composition suitable for topical application to human skin, including leave-on products and wash-off products.Preferably, this term includes a flowable liquid, especially a moisturizing agent, rather than a cosmetic.Leave-on compositions are most preferred.The term "leave-on" used in relation to the composition herein refers to a composition that is applied to the skin or rubbed onto the skin and left on the skin.

[0056] In another embodiment, the present invention relates to the use of an oil having a Hansen Total Solubility Parameter value in the range of 13 to 26 to stabilize a composition comprising a retinoic acid precursor and a functionalized heteroaromatic compound.

[0057] Many types of packaging can be used to store and deliver the compositions of the present invention. The choice of packaging depends on the personal care end use and the viscosity of the composition itself. As an example, leave-on lotions and creams for skin typically use plastic containers with a dispensing end opening covered by a suitable closure. Conventional closures include flip-top hinged lids, screw caps, and non-aerosol pumps. As another example, suitable packaging for antiperspirants, deodorants, and depilatories includes containers with rollerball applicators at the dispensing end when the composition is fluid and has a lower viscosity. If the composition is in stick form, a container with a push-and-rebound mechanism in which the stick is fixed on a platform toward the dispensing orifice is suitable. If the composition is in aerosol form, a metal can pressurized by a propellant and equipped with a spray nozzle is suitable. Generally, patches, bottles, tubes, rollerball applicators, squeeze containers, or jars with lids are preferred. If plastic is desired, it is preferably post-consumer plastic.

[0058] To facilitate a better understanding of the present invention, it will now be described in the context of certain non-limiting examples. Those skilled in the art will recognize that variations of the present invention that differ from the examples given may be implemented without departing from the teachings of the present invention.

[0059] [Example] All samples were made by mixing the noted ingredients under conditions of moderate shear, from about 22°C to about 85°C, and atmospheric pressure. d Data is collected from the CRC Handbook of Solubility Parameters and Other Cohesion Parameters, Second Edition (by Allan FM Barton).

[0060] [Example 1] A formulation containing 3% niacinamide and 0.3% retinyl propionate [Table 1]

[0061] The above ingredients were combined to prepare the emulsified cosmetic composition of the present invention.

[0062] [Example 2] Additional sample preparations [Table 2]

[0063] Additional cosmetic compositions may be made by combining the above ingredients, consistent with the described invention.

[0064] [Example 3] Color stability with varying amounts of oil [Table 3]

[0065] As can be seen from the data, oils used in accordance with the present invention unexpectedly stabilize formulations containing 0.3% RP and 3% niacinamide. Formulations containing greater than 10% oil produce lower ΔE values ​​over time than 5% oil or oil-free formulations, with surprisingly good color stability occurring at about 17-20% loading.

[0066] [Example 4] Color and chemical stability of retinyl propionate (RP) with various oil and niacinamide amounts [Table 4]

[0067] All samples in Example 4 were made to contain 17% total oil content (weight percent) in the composition.

[0068] It is noted from the data that increasing the content of niacinamide resulted in more severe degradation of color over time, thereby resulting in higher ΔE values. Different identities of oil-based solvents corresponding to different Hansen Solubility Parameter values ​​used in this formulation can result in significant differences in color and / or chemical stability, consistent with the present invention. d It can again be seen that oils with δ values ​​yield low ΔE values ​​(i.e., excellent color stability) over time. For example, d Isopropyl myristate and caprylic / capric triglyceride having a δ value are outside the scope of the present invention. d It exhibits better color stability compared to dimethicone and benzyl alcohol, which have similar values.

[0069] The column labeled "RP Remaining" refers to the chemical availability of retinyl propionate over time as a direct measure of the level of retinyl propionate after storage and degradation. This measurement is included to ensure that sufficient bioactive material is still present to provide the desired biofunctionality. It is clear that the amount of RP remaining at the end of 12 weeks does not vary significantly from sample to sample, regardless of the type of oil used or the amount of niacinamide in the composition.

[0070] Sample 12 further contains 1% cetyl alcohol, a retinoid booster, on top of the formulation used in Sample 6. The results show that Sample 12 has better measurable retinyl propionate chemical activity than all other samples, but Sample 12 has unexpectedly poorer color stability, comparable to Sample 6.

[0071] [Example 5] Color stability compared to competing products containing RP [Table 5]

[0072] Comparison of compositions made according to the present invention with competitive benchmark products containing retinyl propionic acid as the retinoic acid precursor showed significantly lower b* values, indicating less yellowing and therefore less color degradation for compositions made within the scope of the present invention. The competitive product selected for this example also contained niacinamide and retinol, but no compatible oil.

[0073] [Example 6] Color stability comparison of competing products containing retinol [Table 6]

[0074] Comparison of compositions made in accordance with the present invention with competitive benchmark products containing retinol as the retinoic acid precursor showed significantly lower b* values ​​at 0 and 4 weeks, demonstrating less yellowing and therefore less color degradation for compositions made within the scope of the present invention. The competitive products selected for this example did not contain niacinamide or any other functionalized heteroaromatic compounds, nor did they contain compatible oils.

[0075] [Example 7] Color stability of competitive products containing retinyl palmitate [Table 7]

[0076] Comparison of compositions made in accordance with the present invention with competitive benchmark products containing retinyl palmitate as the retinoic acid precursor showed significantly lower b* values ​​at week 0 and week 4, indicating less yellowing and therefore less color degradation for compositions made within the scope of the present invention. The competitive products selected for this example did not contain niacinamide or any other functionalized heteroaromatic compounds, nor did they contain compatible oils.

Claims

1. A cosmetic composition comprising: (a) a retinoic acid precursor; (b) a functionalized heteroaromatic compound; and (c) an oil, wherein the oil has a Hansen Total Solubility Parameter of 13 to 26, the functionalized heteroaromatic compound comprises a carboxylic acid functionalized heteroaromatic compound, the carboxylic acid functionalized heteroaromatic compound comprises nicotinic acid, picolinic acid, nicotinate, niacinamide, picolinamide, or a mixture thereof, and the oil comprises 15 to 30% (by weight) of the composition; A cosmetic composition comprising:

2. 2. The cosmetic composition of claim 1, wherein the retinoic acid precursor comprises retinol, retinal, a retinyl ester, or a mixture thereof, and further wherein the composition comprises 0.001 to 10% (by weight) of the retinoic acid precursor or a mixture thereof.

3. 10. The cosmetic composition of claim 1, wherein said composition comprises 0.01 to 10% (by weight) of said functionalized heteroaromatic compound.

4. 2. The cosmetic composition according to claim 1, wherein the oil has a Hansen total solubility parameter of 15 to 25.

5. The cosmetic composition of claim 1, wherein the composition comprises 15 to 25% (by weight) oil.

6. 10. The cosmetic composition of claim 1, wherein the oil is isopropyl myristate, isopropyl palmitate, caprylic / capric triglyceride, or a mixture thereof.

7. 10. The cosmetic composition of claim 1, further comprising at least one of a sunscreen, a light stabilizer, a whitening agent, a wrinkle reducing agent, a colorant, or a mixture thereof.

8. The cosmetic composition of claim 1 , wherein the composition further comprises a retinoid booster.

9. 9. The cosmetic composition of claim 8, wherein the retinoid booster comprises 12-hydroxystearic acid, cetyl alcohol, cetearyl alcohol, cocamide monoethanolamide, linoleoyl monoethanolamide, climbazole, or a mixture thereof.

10. The cosmetic composition of claim 1, wherein the composition further comprises 0.01 to 25% (by weight) of silicone.

11. The cosmetic composition of claim 1, wherein the composition further comprises 0.01 to 2% (by weight) of silicone.

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