Cosmetic compositions with enhanced color stability for retinoic acid precursors

Abstract

The present invention relates to a cosmetic composition containing a functionalized heteroaromatic compound and a retinoic acid precursor. An effective method for stabilizing the color stability of a composition containing a functionalized heteroaromatic compound and a retinoic acid precursor is desired. It has been determined that the combination of a functionalized heteroaromatic compound and a retinoic acid precursor with a compatible oil provides improved color stability of the retinoic acid precursor. Therefore, 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; in particular, skin benefit compositions for topical application to human skin. More specifically, the present invention relates to cosmetic compositions containing a retinoic acid precursor and a compatible oil and a functionalized heteroaromatic compound to provide improved color stability of the composition. Background Art

[0002] Human skin deteriorates due to environmental factors (wind, dry air, sun, pollution, blue light), skin disorders, and the normal aging process (chronological aging). Damaged skin can lead to facial fine lines, wrinkles, yellowing or sallowness, sagging, dehydration, hyperpigmentation, age spots, and general signs of aging. However, the standard definition of ideal skin includes youthful skin with an even tone and smooth texture. Therefore, the demand for "anti-aging" or "pre-aging" cosmetics that reverse, treat or delay the visible signs of damaged skin has grown significantly.

[0003] In recent years, cosmetic compositions containing retinoic acid precursors such as retinol have become quite prominent. When applied topically, retinol, also known as vitamin A, and its many ester derivatives and members of the retinoid family, including, for example, retinyl propionate, are effective in addressing the visible signs of aging skin noted above, among other benefits. Despite the benefits of retinoids, the inclusion of retinoic acid precursors in cosmetic compositions often results in compositions that are difficult to stabilize.

[0004] In addition, many people often look for cosmetics with skin lightening benefits for ideal uniform skin. There is always a need in the industry for cosmetic skin lightening agents with enhanced efficacy and stability. Without being bound or limited by theory, it is believed that, among other benefits, compositions containing functionalized heteroaromatic compounds, particularly niacinamide and / or nicotinic acid salts, can be used to promote uniform skin and skin hydration while reducing the appearance of dull skin and fine lines. Other examples of skin lightening agents that can be used for topical application to the skin include resorcinols such as hexylresorcinol, hydroquinone, arbutin and kojic acid.

[0005] However, it may be challenging to obtain color-stable cosmetic compositions containing retinoic acid precursors. Color instability is worrisome because consumers are sensitive to changes in the color appearance of the cosmetic compositions they use, especially where color changes may be perceived as indicating degradation of chemical efficacy. The color instability of retinoic acid precursors is positively correlated with the chemical instability of retinoic acid precursors in a nonlinear manner, but not in a proportional or exponential manner. The color stability of compositions containing retinoic acid precursors deteriorates in a shorter period of time than the chemical activity. Due to external factors, including impurities in the formulation and interactions with other ingredients such as niacinamide, trace amounts of chemical degradation in retinoic acid precursors can lead to substantial degradation of color. Therefore, it is desirable that cosmetic compositions containing both retinoic acid precursors and functionalized heteroaromatic compounds may face significant color degradation.

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

[0007] Additional Information

[0008] Efforts to combine retinoic acid precursors with functionalized heteroaromatic compounds in the presence of compatible oils have been disclosed.

[0009] US Patent Nos. 5,997,890 and 6,001,377 disclose topical compositions useful for providing an immediate improvement in the appearance of the skin, the topical compositions containing a particulate material and actives for regulating skin condition, preferred options including vitamin B3 compounds and retinoids.

[0010] US Patent Nos. 5,933,998, 5,939,082, 6,150,403, 6,238,678 and 6,217,888 disclose topical compositions for regulating the oiliness and / or shiny appearance of the skin, wherein preferred embodiments contain a retinoid and a vitamin B3 compound.

[0011] US Patent Nos. 6,224,888 and 6,528,071 relate to cosmetic compositions comprising a vitamin B3 compound, an oily liquid emollient, a polar solvent, a solidifying agent, and a colorant.

[0012] US Patent No. 6,183,761 reports a topical composition for regulating the appearance of skin having a vitamin B3 compound, a polycyclic compound, and an acceptable carrier.

[0013] PCT application WO 94 / 09756 relates to a composition for topical application to human skin to promote the repair of photodamaged skin comprising retinol or a derivative thereof and a selected skin lightening agent.

[0014] PCT application WO 98 / 52536 reports skin care compositions with improved skin compatibility which contain a retinoid and a preservative component.

[0015] PCT Application WO 99 / 47115 describes skin care compositions comprising vitamin B3 compounds and an improved carrier system.

[0016] None of the above additional information describes the specific combination of retinoic acid and functionalized heteroaromatic compounds with compatible oils to obtain cosmetic compositions with improved color stability for anti-aging or pre-aging and skin lightening benefits as disclosed in the presently claimed invention. Summary of the invention

[0017] The present inventors have determined that the use of a functionalized heteroaromatic compound with a compatible oil in addition to the use of a retinoic acid precursor enhances the color stability of compositions formulated with the retinoic acid precursor.

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

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

[0020] It has been unexpectedly discovered that cosmetic compositions prepared according to the present invention provide good stability, color stability, anti-aging and skin lightening benefits.

[0021] All other aspects of the invention will become more apparent after consideration of the following detailed description and examples.

[0022] For the avoidance of doubt, the word "comprising" is not meant to limit any stated elements, but rather to include unspecified elements of major or minor functional importance. Therefore, the listed steps, elements or options are not necessarily exhaustive. Whenever the words "including" or "having" are used, these words are meant to be equivalent to "comprising" as defined above.

[0023] As used herein, the term "skin" includes skin on the face, neck, chest, back, arms, armpits, arms, hands, legs, and scalp. As used herein, skin benefit agents refer to components that include components that (a) improve facial or body features such as skin features after topical application, (b) are beneficial to facial or body features such as skin features, or (c): (a) and (b) both. Personal care compositions are compositions for topical application, and include emulsions, creams, gels, essences, pumps or aerosol sprays, ointments, deodorants, antiperspirants, nail care agents, washing compositions, and facial cosmetics. In a particularly preferred embodiment, the composition of the present invention is a wash-free composition, and the skin benefit agent is a retinoic acid precursor compound. As used herein, the terms "retinoids" and "retinoic acid precursors" refer to all natural and / or synthetic analogs of vitamin A, or derivatives thereof having biological activity similar to vitamin A in human skin. The term "one or more derivatives" as used herein with reference to an ingredient refers to a functional group substitution on the compound. As used herein, the term "functionalized" refers to a compound having at least one functional substituent on the compound, including an acyl, hydroxyl, alkoxy, carboxamide (amide) group, carboxyl or alkoxycarbonyl (ester) substituent. "HLB" stands for the hydrophilicity-lipophilicity balance of the surfactant, which is used to measure the degree of hydrophilicity or lipophilicity of the surfactant and is widely used in the art. As used herein, maintaining color stability describes a cosmetic composition having a ΔE of ten (10) or less based on the L*, a* and b* color differences based on the CIELAB color space model obtained on a Hunter Lab spectrophotometer. In general, ΔE≤10 is acceptable, ΔE between 10 and 20 is negotiable, and ΔE>20 is unacceptable. For b* values, the value represents the blue-yellow component of the object color, where negative (-) values ​​represent movement into the blue space, while positive (+) values ​​represent movement into 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 in the range of 13 to 26. The Hansen Total Solubility Parameter is determined based on three Hansen parameters, namely, δ t (defined as the energy from the intermolecular dispersion forces), δ p (defined as the energy from the intermolecular dipole-dipole intermolecular forces) and δ n (Definition of the energy from intermolecular hydrogen bonds). t Values ​​were obtained according to the CRC Handbook of Solubility Parameters and other Cohesion Parameters, 2nd edition, by Allan FM Barton.

[0024] Except in the examples, or where otherwise explicitly indicated, all numbers in this specification expressing amounts of material are to be understood as modified by the word “about.” Unless otherwise indicated, all amounts are by weight of the total composition. DETAILED DESCRIPTION OF THE INVENTION

[0026] The composition of the present invention contains retinoic acid precursor, which generally includes retinyl ester, retinol, retinal or their mixture, preferably retinal, retinyl ester or their mixture.The example of retinyl ester applicable to the present invention includes but is not limited to: retinyl palmitate, retinyl formate, retinyl acetate, retinyl propionate, retinyl butyrate, retinyl valerate, retinyl isovalerate, retinyl caproate, retinyl enanthate, retinyl octanoate, retinyl nonanoate, retinyl decanoate, retinyl undecanoate, retinyl taurine, retinyl tridecanoate, retinyl myristate, retinyl pentadecanoate, retinyl heptadecanoate, retinyl stearate, retinyl isostearate, retinyl nonadecanoate, retinyl arachidonic acid, retinyl behenate, retinyl linoleate and retinyl oleate.Preferred ester for the present invention is selected from retinyl palmitate, retinyl acetate, retinyl propionate and its mixture. Retinyl linoleate and retinyl oleate are also preferred. In a particularly preferred embodiment, the retinoic acid precursor is retinyl propionate. The retinoic acid precursor is used in the composition of the present invention in an amount of 0.001 to 10%, preferably 0.01 to 1%, most preferably 0.01 to 0.5% by weight of the cosmetic composition.

[0027] Based on skin benefits, it is generally desirable to include functionalized heteroaromatic compounds in cosmetic compositions with retinoic acid precursors. However, it has been found that when the composition comprising a retinoic acid precursor is further combined with a functionalized heteroaromatic compound, the color instability of the retinoic acid precursor is exacerbated and manifests as a darker yellow discoloration of the composition, which is a challenge that the present invention can help overcome. In addition to the retinoic acid precursor, the cosmetic composition of the present invention also includes a functionalized heteroaromatic compound. The functionalized heteroaromatic compound is preferably a carboxylic acid functionalized heteroaromatic compound. The carboxylic acid functionalized heteroaromatic compound can be any cosmetically acceptable nicotinic acid, picolinic acid or a derivative or mixture thereof, preferably nicotinic acid, nicotinamide, nicotinic acid salts, picolinic acid, pyridineamide or a mixture thereof, more preferably nicotinamide, pyridineamide or a mixture thereof. By weight of the cosmetic composition, the amount of the functionalized heteroaromatic compound is generally used in an amount of about 0.01 to 10%, preferably about 0.05 to 7%, and more preferably about 0.1 to 5%.

[0028] It has now been unexpectedly determined that the use of a compatible oil in a composition having a retinoic acid precursor and a functionalized heteroaromatic compound can help improve color stability compared to a control of the same vehicle. tOils with a ) value in the range of 13 to 26, preferably in the range of 15 to 25, are most compatible and therefore suitable for use in such cosmetic compositions. Illustrative examples of suitable oils for use in the present invention include isopropyl myristate (δ t =17.5), caprylic / capric triglyceride (δ t =18.9), isopropyl palmitate (δ t =17.2) and benzyl alcohol (δ t =24.7). Illustrative but non-limiting examples are sunflower oil, cottonseed oil, canola oil, grape seed oil, soybean oil, castor oil, borage oil, olive oil, jojoba oil, and mixtures thereof. Monoglycerides and diglycerides may also be useful. Examples of these classes are glyceryl monostearate and glyceryl distearate. Compatible oils are used in the compositions of the present invention in an amount of 13 to 30%, preferably 14 to 28%, and most preferably 15 to 25%, based on the weight of the composition.

[0029] Color stability was 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 measuring cells are loaded onto the LabScan XE measurement port. Color (a*, b*, and L*) are measured and calculated to generate color change data (ΔE) values ​​according to the measurement procedures specified in the associated instrument menu and computer software. b* is a scale based on the blue-yellow color space of the CIELAB color space model, where an increase in b* values ​​indicates an increase in the yellow color component, while a decrease in b* values ​​indicates an increase in the blue color component.

[0030] It has also been unexpectedly discovered that compositions prepared according to the present invention provide good stability and color stability to the composition itself, as well as anti-aging and skin lightening benefits when applied to the skin.

[0031] The cosmetic composition of the present invention may also include a cosmetically acceptable vehicle to be used as a diluent, dispersant or carrier for the skin benefit agent in the composition to promote its distribution when the composition is applied to the skin. Such cosmetically acceptable vehicles may be aqueous, anhydrous or emulsions. Oily carriers may form an emulsion system as a carrier in the presence of water and an emulsifier. Preferably, the composition is aqueous or an emulsion, especially a water-in-oil or an oil-in-water emulsion, preferably an oil-in-water emulsion. The cosmetic composition is typically in the form of, but not limited to, a cream or an emulsion.

[0032] Suitable carriers used in the present invention include water, sea water, rose water (e.g., Damascus rose (Rosa Damascena) flower water), tea (e.g., tea (Camellia Sinensis) leaf water), Aloe Barbadensis (Aloe) leaf juice, witch hazel (e.g., North American witch hazel (Hamamelis Virginiana) extract), lavender water (e.g., lavender (Lavendula Angustifolia) flower water), grape water (e.g., grape (Vitis Vinifera) fruit water and grape juice). In the most preferred embodiment, water is the carrier. Based on the weight of the cosmetic composition and including all ranges contained therein, the amount of water can be preferably 5 to 85%, more preferably 15 to 75%, most preferably 30 to 70%. In the absence of other cosmetic excipients, the cosmetically acceptable vehicle can form the remainder of the composition. In addition to water, suitable carrier categories include, but are not limited to, silicones, polyols, fatty acids, hydrocarbons, triglycerides, waxes and thickeners.

[0033] It is within the scope of the present invention to contain silicones, which can be divided into volatile and non-volatile categories. The amount can be in the range of, for example, 0.01 to 25% by weight, more preferably 0.1 to 20% by weight of the cosmetic composition. In one embodiment of the invention, the composition contains 0.01 to 2% by weight of silicone without a significant effect on the organoleptic properties. As used herein, the term "volatile" refers to those materials that have 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.

[0034] Nonvolatile silicones useful in the composition include polyalkyl siloxanes, polyalkylaryl siloxanes, and polyether siloxane copolymers. Substantially nonvolatile polyalkyl siloxanes useful herein include, for example, those having a viscosity of about 5 x 10 -6 Up to 0.1m 2 Emulsifying and non-emulsifying silicone elastomers are also suitable for use in the cosmetic compositions of the present invention.

[0035] Conventional humectants of the general polyol class of materials may be used in the present invention. Typical polyols include glycerol (i.e., glycerine or glycerin), propylene glycol, dipropylene glycol, polypropylene glycol, polyethylene glycol, sorbitol, hydroxypropyl sorbitol, hexylene glycol, 1,3-butylene glycol, isopentyl glycol, 1,2,6-hexanetriol, ethoxylated glycerol, propoxylated glycerol, and mixtures thereof. The most preferred embodiment includes glycerol, propylene glycol, or mixtures thereof. The amount of humectant used may be anywhere from 0.1 to 25%, preferably 0.5 to 20%, and more preferably 1 to 15%, by weight of the cosmetic composition.

[0036] Retinoid enhancers may also be useful ingredients for incorporation into the compositions of the present invention, such as fatty acids and their derivatives. 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, 5,955092, 5,885,595, 5,759,556, 5,693,330, 7,959,913, 8,226,933, and 8,409,550), the term "retinoid enhancer" is used to collectively refer to compounds that have been identified as enhancing 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. The synergists, alone or in combination with other synergists, help to enhance the efficacy of the retinoic acid precursor. The term "fat" refers to carbon chain lengths of 10 to 30 carbon atoms. Examples 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 alcohol, lauryl alcohol, myristyl alcohol, palmityl alcohol, cetearyl alcohol, stearyl alcohol and oleyl alcohol; fatty esters such as 2-ethylhexyl myristate, isopropyl stearate and isostearyl palmitate, triisopropyl trilinoleate and trilauryl citrate, lauryl palmitate, myristyl lactate, oleyl erucate and stearyl oleate, coco-caprylate / caprate (a blend of coco-caprylate and coco-caprate), propylene glycol myristyl ether acetate, diisopropyl adipate and cetyl caprylate; 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 synergist compounds include carotenoids, flavonoids, cyclic and non-cyclic aromatics, antifungal agents (e.g., bifonazole, climbazole, clotrimazole, econazole, ketoconazole, miconazole), phospholipid analogs, urea, phosphatidylethanolamine, phosphatidylcholine, sphingomyelin, natural colorants (e.g., coumarin), quinoline, isoquinoline, metyrapone, and mixtures thereof. In one embodiment of the present invention, fatty acids, fatty alcohols, fatty amides, climbazole, or mixtures thereof may be used as retinoid synergists. In a particularly preferred embodiment of the present invention, 12-hydroxystearic acid, cetyl alcohol, cetearyl alcohol, CMEA, LAMEA, climbazole, or mixtures thereof are used as retinoid synergists. When used, 0.01 to 5% by weight of the retinoid synergist compound is present in the composition.

[0037] Waxes and wax esters are also suitable for use in the compositions of the present invention. These waxes include animal-derived waxes or those waxes from animal by-products (e.g., beeswax, spermaceti, China wax, wool wax, shellac wax), plant-derived waxes (e.g., behenyl 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, paraffin wax, ozokerite wax), and synthetic derivatives of natural waxes. The amount of waxes and wax esters used may be from 0.01 to 10%, preferably from 0.1 to 8%, by weight of the composition.

[0038] The cosmetic composition of the present invention may optionally contain hydrocarbons. Suitable hydrocarbons may include mineral oil, petrolatum and poly-alpha-olefins. Examples of preferred volatile hydrocarbons include polydecanes such as isodecane and isododecane, and C7-C8 to C 12 -C 15 Isoparaffins.

[0039] The cosmetic composition prepared according to the present invention may optionally contain one or more thickeners at a content level of 0.05 to 10%, preferably 0.1 to 5%, more preferably 0.25 to 4%, by weight of the composition. Useful thickeners include polysaccharides, including starches, natural / synthetic gums, and celluloses. Suitable starches include tapioca starch, corn starch, potato starch, aluminum starch octenyl succinate, and hydroxypropyl starch sodium phosphate. Suitable gums include xanthan gum, sclerotium, pectin, gum karaya, gum arabic, agar, guar gum, carrageenan, alginates, and combinations thereof. Suitable celluloses include hydroxypropyl cellulose, hydroxypropyl methylcellulose, ethyl cellulose, and sodium carboxymethyl cellulose. Synthetic polymers used as thickeners are also suitable for use, including polyacrylamide, carbomer, and taurate copolymers.

[0040] An emulsifier is preferably present in the cosmetic composition of the present invention. Emulsifiers suitable for use in the present invention may have an HLB of 2.5 to 17. When an oil continuous emulsion is desired, the HLB of the emulsifier used may be 2.5 to 7.5, preferably 3 to 6.5, most preferably 3 to 6, including all ranges subsumed therein. When a water continuous emulsion is desired, the HLB of the emulsifier used may be 8 to 17, preferably 8.5 to 15, most preferably 9 to 14, including all ranges subsumed therein.

[0041] The total concentration of the emulsifier may be from 0.1 to 20%, preferably from 1 to 10%, most preferably from 1 to 8%, including all ranges subsumed therein, based on the weight of the composition. The emulsifier may be selected from anionic, nonionic, cationic and amphoteric surfactants. Particularly preferred nonionic surfactants are those having: C 2 O 2 condensed with from about 2 to about 100 moles of ethylene oxide or propylene oxide per mole of hydrophobe. 10 -C 20Fatty alcohol or fatty acid hydrophobe; C2-C 10 Alkylphenols; mono- and di-fatty acid esters of ethylene glycol; fatty acid monoglycerides; sorbitan mono- and di-C8-C 20 Fatty acids; and polyoxyethylene sorbitan and combinations thereof. Alkyl polyglycosides and sugar fatty amides (e.g., methyl glucamide) are also suitable nonionic emulsifiers. Still other preferred nonionic surfactants include glyceryl stearate, ethylene glycol stearate, and stearamide AMP.

[0042] Preferred anionic emulsifiers include alkyl ether sulfates and sulfonates, alkyl sulfates and sulfonates, alkyl benzene sulfonates, alkyl and dialkyl sulfosuccinates, C8-C 20 Acyl isethionate, C8-C 20 Acyl methyl isethionate, C8-C 20 Acyl methyl taurates, C8-C20 alkyl ether phosphates, alkyl ether carboxylates and combinations thereof.

[0043] Cationic emulsifiers that may be used include, for example, palmitamidopropyltrimonium chloride, distearyldimethylammonium chloride, diester quaternary ammonium compounds (eg, distearylethyldimethylammonium chloride), and mixtures thereof.

[0044] Useful amphoteric emulsifiers may include cocamidopropyl betaine, C 12 -C 20 Trialkyl betaine, sodium lauroamphoacetate and sodium lauroyl diamphoacetate or mixtures thereof.

[0045] Fragrance, fixative, abrasive and additional skin benefit agent can be optionally included in the cosmetic composition of the present invention. Skin benefit agent suitable for use in the present invention means including but not limited to sunscreen, colorant, moisturizer, emollient, occlusive agent, plant extract, optical agent, skin lightening agent, anti-inflammatory agent, anti-acne agent, antioxidant, sunscreen, light stabilizer, surfactant, wrinkle reducing agent, colorant, desquamation promoter, exfoliant, mixture thereof, etc. Each of these substances can be 0.05 to 5% by weight, preferably 0.1 to 3% by weight.

[0046] The cosmetic composition of the present invention may include 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. Derivatives of the vitamins may also be used. For example, derivatives of vitamin C include ascorbyl tetraisopalmitate, magnesium ascorbyl phosphate, and ascorbyl glucoside. Derivatives of vitamin E include tocopheryl acetate, tocopheryl palmitate, and tocopheryl linoleate. When present in a cosmetic composition according to the present invention, the total amount of the additional vitamins may be 0.01 to 10%, preferably 0.05 to 7%, and optimally 0.1 to 5%, by weight of the cosmetic composition.

[0047] 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 metal components; alpha-hydroxy acids, beta-hydroxy acids, for example salicylic acid and its derivatives (such as 5-octanoyl salicylic acid, heptyl-4-salicylic acid and 4-methoxysalicylic acid); kojic acid; hydroquinone and arbutin; resveratrol; carbohydrate isomers; undecylenoyl phenylalanine; resorcinol derivatives (particularly 4-substituted resorcinol derivatives, including 4-ethylresorcinol); phenol, 4-isopropylresorcinol, 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 PCA zinc and PCA sodium; and skin benefit agents and their derivatives (12-hydroxystearic acid; celery acid; conjugated linoleic acid; octadecanoic acid; hyaluronic acid and its salt derivatives); mixtures thereof, etc. Such skin benefit agents, when used, together constitute 0.001 to 12% by weight of the cosmetic composition.

[0048] A wide selection of plant extracts may optionally be included in the cosmetic compositions of the present invention. The extracts may be dissolved in water or oil contained in a solvent that is hydrophilic or hydrophobic, respectively. In preferred embodiments, water or ethanol is the extraction solvent. Illustrative examples include those extracted from green tea, yarrow, chamomile, licorice, aloe, tangerine, willow bark, alfalfa, algae, grape seed, witch hazel, sage, thyme and rosemary, as well as those derived from sea buckthorn, moringa, argan tree, avocado, calendula, seaweed and marula tree. Soybean extracts may be used, especially when it is desired to include retinol. When used, such extracts are preferably used in a total amount of 0.001 to 12% by weight of the cosmetic composition.

[0049] It is within the scope of the present invention to optionally include sunscreens and light stabilizers. Sunscreens and light stabilizers that can be used in the compositions of the present invention include, for example, octyl methoxycinnamate (OMK), ethylhexyl salicylate, phenylbenzimidazole sulfonic acid (Ensulizole), ethylhexyl p-methoxycinnamate (Parsol Avobenzone (butyl methoxydibenzoylmethane) (available from Parsol Materials such as benzophenone-3 (also known as oxybenzone) and benzophenone-3 (obtained from benzophenone) can be used. Inorganic sunscreen actives such as ultrafine titanium dioxide (preferably with a particle size of less than 150 nm, most preferably less than 100 nm) and zinc oxide can be used, and polyethylene and various other polymers are also suitable sunscreen agents. Other sunscreens suitable for use include para-aminobenzoic acid (PABA), octyl dimethyl-PABA, 2-ethoxyethyl p-methoxycinnamate, benzophenone-1, benzophenone-2, benzophenone-6, benzophenone-8, benzophenone-9, benzophenone-12, homomethylsalicylate, aminobenzoic acid amine, benzophenone-4, triethanolamine salicylate, terephthalylidene dicamphor sulfonic acid, bis-octylphenol triazole, bis-ethylhexyloxyphenol methoxyphenyl triazine, disodium phenyl dibenzimidazole tetrasulfonate, drometrizole trisiloxane, octyl triazone, diethylhexyl butyramide triazone (iscotrizinol), polysilicone-15, isopentenyl-4-methoxycinnamate, mixtures thereof, etc. Also suitable for use is octocrylene. 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.

[0050] The cosmetic composition of the present invention may also contain natural and synthetic antioxidants. Illustrative but non-limiting examples of antioxidants used in the composition include butylated hydroxytoluene (BHT), dilauryl thiodipropionate, pentaerythritol tetrakis (di-tert-butyl hydroxyhydrocinnamate) ester and polyphenols. When used, the total weight percentage of antioxidants in the present invention is preferably 0.01 to 4%, more preferably 0.02 to 3%, and most preferably 0.05 to 2%.

[0051] Optionally, one or more colorants may also be included in the cosmetic composition of the present invention. Colorants include dyes or pigments from natural or synthetic sources. The dye selected for use may be organic or inorganic, and may be 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, beta-carotene, D&C Purple 2, D&C Yellow 11, D&C Orange 5, and Quinoline Yellow. Suitable pigments 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, ochres (yellow ochre, red ochre, brown ochre, iron hydroxide), metal oxides (zinc oxide, zirconium oxide, iron oxide, cerium oxide, chromium oxide), manganese violet, ultramarine blue, hydrated chromium and ferric blue, or metal powders (aluminum, bronze or copper powder); organic pigments such as nitroso, nitro, azo, phthalocyanine, dioxazine, xanthene, pyrene, quinoline, anthraquinone, triphenylmethane, fluoran, quinacridone, metal complexes, isoindolinone, isoindolinone, perinone, dinaphthalene Perylene, diketopyrrolopyrrole, indigo, thioindigo, dioxazine, triphenylmethane and quinoline yellow compounds; and lakes (particularly 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 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 F&D Blue No. 1 Aluminum Lake. Mothers of pearl, 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 colorants suitable for use include chalk, activated carbon and carbon black. When used, the cosmetic composition comprises from 0.01 to 20 wt. %, preferably from 0.1 to 15 wt. %, more preferably from 0.5 to 10 wt. % of the colorant relative to the weight of the cosmetic composition.

[0052] Conventional 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 aminomethyl propanol. In a preferred embodiment, the pH of the cosmetic composition 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 composition of the present invention is from about 1,000 to about 200,000 cp, preferably from about 5,000 to 180,000 cp, and most preferably from about 10,000 to about 150,000 cp, which is a viscosity of 100% t / cm3 at 25°C and 1 s -1The viscosity can be measured under conditions of shear rate using a strain controlled parallel plate rheometer commercially available from suppliers such as TA Instruments under the Discovery name. Alternatively, viscosity can also be measured using a Brookfield viscometer (at a speed of 20 rpm, spindle 5, heliostat off, at 25°C for one (1) minute). The cosmetic composition of the present invention can be formulated as an emulsion with a viscosity of 4,000 to 10,000 mPas, a liquid cream with a viscosity of 10,000 to 20,000 mPas, or a cream with a viscosity of 20,000 to 200,000 mPas or more.

[0053] Preservatives may be incorporated into the compositions of the present invention as needed to prevent the growth of potentially harmful microorganisms. Cosmetic chemists are familiar with suitable preservatives and routinely select them to meet preservative testing and product stability testing. The selection of preservative systems should take into account the use of the composition and possible 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, ethylhexylglycerol, 1,2-octanediol, methylparaben, propylparaben, imidazolidinyl urea, sodium dehydroacetate, propylene glycol, alkyl esters of parahydroxybenzoic acid, sodium benzoate, benzoic acid, parahydroxyacetophenone, DMDM ​​hydantoin derivatives, propionates, and various quaternary ammonium compounds. Preservatives are preferably used in an amount of 0.01 to 2%, including all ranges contained therein, based on the weight of the composition.

[0054] When preparing the cosmetic composition of the present invention, the required ingredients are mixed by conventional methods. The cosmetic composition is prepared by mixing the ingredients in no particular order under moderate shear conditions at about 22°C to about 85°C and atmospheric pressure.

[0055] The cosmetic compositions of the present invention are compositions suitable for topical application to human skin, including leave-on and rinse-off products. Preferably, the term includes fluid liquids, particularly moisturizers rather than makeup products. Most preferred are leave-on compositions. The term "leave-on" as used herein with respect to compositions refers to compositions that are applied or rubbed onto the skin and left thereon.

[0056] In another embodiment, the present invention relates to the use of oils 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] There are many types of packaging that can be used to store and deliver the composition of the present invention. The choice of packaging depends on the end use of personal care and the viscosity of the composition itself. As an example, disposable emulsions and creams for skin are usually used in plastic containers with an opening at the distribution end covered by a suitable closure. Traditional closures include hinged lids, screw caps and non-aerosol pumps with pull-off lids. As another example, if the composition is fluid and has a thinner viscosity, suitable packaging for antiperspirants, deodorants and depilatories includes a container with a roller ball applicator at the distribution end. If the composition is in the form of a stick, a container with a propel-repel mechanism is suitable, wherein the stick is fixed on the platform toward the distribution hole. If the composition is in the form of an aerosol, a metal can pressurized by a propellant and having a nozzle is suitable. Generally, patches, bottles, tubes, roller ball applicators, squeeze containers or wide-mouth bottles with lids are preferred. When plastics are needed, it is preferred to be post-consumer resin.

[0058] The present invention will now be described in the context of the following specific non-limiting examples to facilitate a better understanding of the present invention. One of ordinary skill in the art will recognize that variations of the present invention different from the given embodiments can be implemented without departing from the teachings of the present invention. DETAILED DESCRIPTION

[0059] Example

[0060] All samples were prepared by mixing the above ingredients under conditions of moderate shear, from about 22°C to about 85°C, and atmospheric pressure. t The data were collected from the CRC Handbook of Solubility Parameters and Other Cohesion Parameters, 2nd Edition (Allan F. M Barton).

[0061] Example 1: Formulation containing 3% niacinamide and 0.3% retinyl propionate

[0062] Element weight% water margin glycerin 7.00 Chelating agents 0.10 Thickener 2.00 Niacinamide 3.00 preservative 0.70 Cetyl Alcohol 0.50 Emulsifier 2.50 Antioxidants 0.10 Oil 17 Retinyl Propionate 0.30

[0063] According to the present invention, an emulsion cosmetic composition is prepared by combining the above-mentioned ingredients.

[0064] Example 2: Additional sample formulations

[0065]

[0066] Additional cosmetic compositions can be prepared by combining the above-described ingredients consistent with the present invention.

[0067] Example 3: Color stability with different oil levels

[0068]

[0069] As can be seen from the data, the oil used according to the present invention unexpectedly stabilizes formulations containing 0.3% RP and 3% niacinamide. Formulations containing more than 10% oil produce lower ΔE values ​​over time than formulations containing 5% oil or no oil, with surprisingly excellent color stability occurring at levels of about 17% to 20%.

[0070] Example 4: Color and Chemical Stability of Retinyl Propionate (RP) with Different Oil and Niacinamide Levels

[0071]

[0072]

[0073] All samples in Example 4 were prepared to contain 17% total oil content (by weight) in the composition.

[0074] From the data, it can be seen that increasing levels of niacinamide lead to greater degradation of color over time, resulting in higher ΔE values. The different characteristics of the oily solvents used in the formulation corresponding to different Hansen Solubility Parameter values ​​can lead to significant differences in color and / or chemical stability, where again it can be seen that having ΔE values ​​consistent with the present invention is not as good as the ΔE values ​​of the present invention. t The oil with the value of ΔE produces lower ΔE value (i.e., excellent color stability) over time. For example, both have ΔE within the range of the present invention. t The isopropyl myristate and caprylic / capric triglyceride with a δ value outside the invention range t The values ​​of dimethicone and benzyl alcohol showed greater color stability.

[0075] The column labeled "RP Residual" refers to the chemical efficacy 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 there is still enough bioactive to provide the desired biological function. It is clear that regardless of the type of oil used or the amount of niacinamide in the composition, the amount of RP residual at the end of 12 weeks does not fluctuate greatly from sample to sample.

[0076] Sample 12 contains 1% of the retinoid synergist cetyl alcohol in addition to the formulation used in Sample 6. The results show that although the measurable chemical activity of the retinyl propionate of Sample 12 is superior to that of all other samples and Sample 12 is comparable to Sample 6, Sample 12 surprisingly has lower color stability than Sample 6.

[0077] Example 5: Color stability comparison with competitive products containing RP

[0078]

[0079] For compositions prepared within the scope of the present invention, a comparison of the compositions prepared according to the present invention with a competitive product benchmark containing retinyl propionate as a retinoic acid precursor exhibited significantly lower b* values, indicating less yellowing and therefore less color degradation. The competitive product selected in this example further contained niacinamide and retinol instead of compatible oils.

[0080] Example 6: Comparison of Color Stability of Competitive Products Containing Retinol

[0081]

[0082] For compositions prepared within the scope of the present invention, a comparison of the compositions prepared according to the present invention to a competitive product benchmark containing retinol as a retinoic acid precursor showed significantly lower b* values ​​at 0 and 4 weeks, indicating less yellowing and therefore less color degradation. The competitive product selected in this example contained neither niacinamide or any other functionalized heteroaromatic compound nor a compatible oil.

[0083] Example 7: Color Stability of Competitive Products Containing Retinyl Palmitate

[0084]

[0085] For compositions prepared within the scope of the present invention, a comparison of the compositions prepared according to the present invention to a competitive product benchmark containing retinyl palmitate as a retinoic acid precursor showed significantly lower b* values ​​at the 0 and 4 week time points, indicating less yellowing and therefore less color degradation. The competitive product selected in this example contained neither niacinamide or any other functionalized heteroaromatic compound nor a compatible oil.

Claims

1. A cosmetic composition comprising: (a) a retinoic acid precursor; wherein the retinoic acid precursor is selected from the group consisting of retinol, retinal esters, retinyl esters, and mixtures thereof; and wherein the composition comprises 0.001 to 10% by weight of the retinoic acid precursor or mixtures thereof; (b) a functionalized heteroaromatic compound; wherein the functionalized heteroaromatic compound is a carboxylic acid functionalized heteroaromatic compound; wherein the carboxylic acid functionalized heteroaromatic compound comprises nicotinic acid, picolinic acid, a nicotinate, nicotinamide, pyridineamide, or a mixture thereof; and wherein the composition comprises from 0.01 to 10 weight percent of the functionalized heteroaromatic compound; and (c) an oil, wherein the oil has a Hansen Total Solubility Parameter of 13 to 26, and the oil is selected from the group consisting of isopropyl myristate, isopropyl palmitate, caprylic / capric triglyceride, or mixtures thereof; and wherein the oil comprises 15 to 30 wt % of the composition.

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

3. The cosmetic composition according to claim 1 or 2, wherein the composition comprises 15 to 25% by weight of oil.

4. The cosmetic composition according to claim 1 or 2, wherein the composition further comprises at least one of a sunscreen, a light stabilizer, a skin lightening agent, a wrinkle reducing agent, a colorant, or a mixture thereof.

5. The cosmetic composition according to claim 1 or 2, wherein the composition further comprises a retinoid synergist; and wherein the retinoid synergist comprises 12-hydroxystearic acid, cetyl alcohol, cetearyl alcohol, cocamide monoethanolamide, linoleoyl monoethanolamide, climbazole or a mixture thereof.

6. The cosmetic composition according to claim 1 or 2, wherein the composition further comprises 0.01 to 25 wt% of silicone.

7. The cosmetic composition according to claim 6, wherein the composition further comprises 0.01 to 2 wt% of silicone.

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