Solubilizer for functional active compounds

Abstract

A photoprotective topical composition comprising: (i) at least one functional active; and (ii) at least one solubilizing compound having the structure of Formula I: #imgabs0# wherein R is C 5 ‑C 10 Cycloalkyl or straight or branched chain alkylcycloalkyl, wherein the ring size is C 5 ‑C 7 ; R 1 , R 2 and R 3 Each independently selected from H and straight or branched C 1 ‑C 4 Alkyl, provided that R 1 , R 2 , R 3 wherein at least two of the solubilizing compounds are H; wherein the solubilizing compound is present in an amount effective to dissolve the functional active. Also disclosed is a method of treating skin, lips, nails, hair, ears, eyelashes, eyebrows and / or scalp with an effective amount of the composition.

Description

Technical Field

[0001] The present application relates to topical compositions, more particularly, to photoprotective compositions comprising (i) at least one functional active; and (ii) at least one solubilizing compound, wherein the composition is visually clear, odorless, and freeze-thaw stable. Background Art

[0002] The appearance and health of the skin are constantly affected by a variety of factors, including, for example, humidity, UV rays, cosmetics, aging, disease, stress, smoking and dietary habits, each of which can cause various skin changes. In addition, certain changes that occur in the skin are characteristic of aging or exposure to sunlight, many of which are reflected in changes in the structure of the skin in particular. The main clinical signs of skin aging, in particular, the appearance of fine lines and deep wrinkles, each of which can increase with age. Both chronological aging of the skin and photoaging of the skin, due to exposure of the skin to sunlight, UV radiation and other forms of actinic radiation, can cause wrinkles.

[0003] It is well known that solar radiation between 290 and 400 nm is harmful to organic matter, including human skin. In particular, radiation with a wavelength between 290 and 320 nm, the so-called UV-B region, is associated with the occurrence of erythema and sunburn, the severity of which depends on the duration of exposure. In addition, it has been determined that radiation between 320 and 400 nm, the so-called UV-A, which is associated with skin tanning, can cause changes and significant damage to the skin, especially in the case of sensitive skin, or in the case of continuous exposure to radiation. It has been shown that UV-A radiation, in addition to causing damage to elastin and collagen (as a result of which skin aging), can also be the cause of some phototoxic and photoallergic reactions. Moreover, the presence of UV-A can also enhance the harmful effects of UV-B.

[0004] Many commercial products (e.g., personal care, sunscreen, pharmaceutical, agricultural and industrial compositions) containing active or functional compounds are available. These active or functional compounds generally require solubilization in the form of solutions, emulsions or dispersions in aqueous or non-aqueous form. For example, products containing aromatic compounds such as avobenzone ( 517) and / or benzophenone-3( 567)) Sunscreen formulations containing active UVA / UVB absorbing ingredients require solubilization to prevent crystallization. Several such solubilizers are known, for example, ethyl benzoate and C 12 -C 15 Alkyl benzoate (Finosolve TN; Witconol APM, produced and sold by Witco). However, the former compound is a strong irritant, and the latter is just a poor solvent for avobenzone and benzophenone-3.

[0005] U.S. Patent Nos. 7,166,275 and 7,691,363, assigned to ISP Investments Inc., disclose compositions of active or functional organic compounds dissolved in phenethyl esters, which are aryl carboxylic acid esters of 2-phenylethanol. The phenethyl esters may be 2-phenylethyl benzoate, 2-phenylethyl toluate, or 2-phenylethyl phthalate. The active or functional organic compound may be a solid organic compound, for example, a personal care, cosmetic, sunscreen, pharmaceutical, agricultural, or industrial compound. Preferred actives include active sunscreen ingredients, for example, UVA and / or UVB sunscreens (such as avobenzone and / or benzophenone-3). X-Tend sold by Ashland Specialty Ingredients TM 226, is an ester of 2-phenylethanol and benzoic acid. It has a high solubilizing capacity for solid organic sunscreens such as oxybenzone and avobenzone and has gained wide commercial acceptance. It exhibits excellent skin feel and also increases the critical wavelength and UVA / UVB ratio of some formulations. It can also be used to enhance the gloss of hair sprays, shine sprays or styling creams. It is a colorless to pale yellow liquid with a faint rose odor.

[0006] US Patent No. 7,785,573 assigned to ISP Investments Inc. discloses solubilization by esters of aromatic alcohols such as phenethyl alcohol, benzyl alcohol or substituted benzyl alcohols with alkyl or cycloalkyl carboxylic acids, or by carbonates of the aromatic alcohols with alkyl or cycloalkyl carbonic acids.

[0007] U.S. Patent No. 7,364,721 assigned to L'Oreal discloses cosmetic compositions including active or functional organic compounds solubilized by safe and effective organic solvents such as aryl carboxylic acid esters of 2-phenylethanol (eg, 2-phenylethyl benzoate, 2-phenylethyl toluate, or di-2-phenylethyl phthalate).

[0008] Despite the solutions proposed by the above patents and other approaches described in the public literature, there remains a need for effective cosmetic or dermatological compositions to reduce skin damage caused by exposure to UV radiation.

[0009] Therefore, it is desirable to provide improved cosmetic or dermatological compositions having better solubilizing compounds (capable of dissolving functional or organic compounds used therein, particularly at low temperatures) while having greater regulatory acceptability and consumer acceptability, such as reduced irritation or hypoallergenicity, odorless (no pungent odor) and / or colorless, causing less inconvenience to the user.

[0010] Therefore, the main object of the present application is to provide a photoprotective composition that can eliminate or reduce undesirable properties such as instability, irritation, allergy, pungent odor, color and other related problems. SUMMARY OF THE INVENTION

[0012] In one aspect, the present application provides a photoprotective topical composition comprising (i) at least one functional active; and (ii) at least one solubilizing compound having Formula I:

[0013]

[0014] Where R is C5-C 10 Cycloalkyl or linear or branched alkylcycloalkyl, wherein the ring size is C5-C7; R1, R2 and R3 are each independently selected from H and linear or branched C1-C4 alkyl, provided that at least two of R1, R2, R3 are H; wherein the solubilizing compound is present in an amount effective to dissolve the functional active.

[0015] On the other hand, the present application provides a solubilizing compound (or solubilizer) selected from 2-cyclohexyl toluate, 3-cyclohexyl toluate, 4-cyclohexyl toluate, 3-cyclohexylmethyl toluate, 3-cyclopentyl toluate, 3-cycloheptyl toluate and combinations thereof, present in an amount of about 0.1% wt. / wt. to about 70% wt. / wt., preferably 0.1% wt. / wt. to about 50% wt. / wt. of the total photoprotective topical composition.

[0016] In another aspect, the present application provides a photoprotective topical composition formulated as an oil-in-water emulsion, a water-in-oil emulsion, an oil-water-oil emulsion, a water-oil-water emulsion, a water-in-silicone emulsion, an oil solution, a lipid fusion, a hydroalcoholic gel, an anhydrous formulation, an anhydrous spray, an anhydrous gel, an anhydrous xerogel, an aqueous gel, a gel-cream SPF 20, an SPF 30 cream, an alcoholic solution, a hydroalcoholic solution, an emulsion, a lotion, a powder, a stick, a roll-on, a spray, a wipe, a wax, a mousse, an aerosol, a cream, a patch, a pomade, a pump spray, a solution, a towelette, a paste, a powder or a spray.

[0017] In yet another aspect, the present application provides a method for cosmetic treatment or care of the skin, lips, nails, hair, ears, eyelashes, eyebrows and / or scalp, comprising topically applying thereto an effective amount of the photoprotective topical composition of the present application.

[0018] In yet another aspect, the present application provides a method for photoprotecting exposed and / or unexposed skin, nails, hair, lips, ears, eyebrows, eyelashes and / or scalp from the damaging effects of ultraviolet (UV) radiation, which comprises topically applying thereto an effective amount of the cosmetic / dermatological composition of the present application.

[0019] In yet another aspect, the present application provides a photoprotective topical sunscreen composition for UV protection of human skin and / or hair, comprising: (a) from about 1% wt. / wt. to about 70% wt. / wt. of at least one active sunscreen agent; (b) from about 0.1% wt. / wt. to about 50% wt. / wt. of at least one solubilizing compound selected from 3-cyclohexyl toluate, 4-cyclohexyl toluate, or a combination thereof; and (c) from about 1% wt. / wt. to about 80% wt. / wt. of at least one topically-applicable, cosmetically or dermatologically acceptable carrier. BRIEF DESCRIPTION OF THE DRAWINGS

[0021] Further embodiments of the present invention can be understood with reference to the accompanying drawings.

[0022] Figure 1 Consumer odor evaluations of prior art and invention C12-15 alkyl benzoates are shown.

[0023] Figure 2 Shown is the solubility of sunscreen agents in cyclohexyl toluate and phenethyl benzoate of the present invention at 25°C.

[0024] Figure 3 Shown is the solubility of sunscreen agents in cyclohexyl toluate and C12-15 alkyl benzoate at 25°C.

[0025] Figure 4 The solubility of sunscreen agents in cyclohexyl toluate and various esters is shown.

[0026] Figure 5 The solubility of sunscreen agents in cyclohexyl toluate and various esters is shown.

[0027] Figure 6 A solubility comparison in cyclohexyl toluate and C12-15 alkyl benzoate is shown. DETAILED DESCRIPTION OF THE INVENTION

[0029] While the specification concludes with the claims particularly pointing out and distinctly stating what is regarded as the invention, it is anticipated that the present invention will be more readily understood by reading the following detailed description of the invention and by studying the included examples.

[0030] Unless otherwise defined herein, technical terms used in connection with the disclosed and / or claimed inventive concepts shall have the meanings commonly understood by those of ordinary skill in the art. In addition, unless otherwise required by context, singular terms shall include pluralities, and plural terms shall include the singular.

[0031] All patents (published patent applications) and non-patent publications cited in any part of this application are expressly incorporated herein by reference in their entirety to the same extent as if each individual patent or publication was specifically and individually indicated to be incorporated by reference.

[0032] As used in accordance with the present disclosure, the following terms shall be understood to have the following meanings, unless otherwise indicated.

[0033] The use of the word "a" or "an" when used with the term "comprising" means "a", but it is also consistent with the meaning of "one or more", "at least one", and "one or more than one". The use of the term "or" is used to mean "and / or" unless explicitly stated to refer to alternatives only when the alternatives are mutually exclusive, but the present disclosure supports the definition of referring to only the alternative and "and / or".

[0034] All percentages, ratios and proportions used herein are on a weight basis unless otherwise specified.

[0035] As used herein, the words "comprise" (and any form of comprise, such as "comprises" and "comprises"), "have" (and any form of have, such as "have" and "has"), "include" (and any form of include, such as "includes" and "include"), or "contain" (and any form of contain, such as "contains" and "contain") are inclusive or open-ended and do not exclude additional, unreferenced elements or method steps. The term "or combinations thereof" as used herein refers to all permutations and combinations of the items listed before the term. For example, "A, B, C, or combinations thereof" is intended to include at least one of the following: A, B, C, AB, AC, BC, or ABC and, if order is important in the particular context, BA, CA, CB, CBA, BCA, ACB, BAC, or CAB. Continuing with this example, expressly included are combinations containing repetitions of one or more items or terms, such as BB, AAA, MB, BBC, AAABCCCC, CBBAAA, and CABABB, etc. Those skilled in the art will understand that there is generally no limit to the number of items or terms in any combination unless otherwise apparent from the context.

[0036] The terms "preferred", "preferably" and variations thereof refer to embodiments of the invention that provide certain benefits under certain circumstances. However, other embodiments are also preferred under the same or other circumstances. In addition, the recitation of one or more preferred embodiments does not indicate that other embodiments are not useful, and is not intended to exclude other embodiments from the scope of the invention.

[0037] Reference herein to "one embodiment" or "an aspect" or "one form" or "an object" of the present application includes one or more such embodiments, aspects, forms or objects unless the context clearly indicates otherwise.

[0038] The term "each independently selected from" means that when a group occurs more than once in a structure, the group can be independently selected at each of its occurrences.

[0039] The term "alkyl" refers to a monovalent linear or branched C1-C12 radical, optionally with one or more heteroatoms, which may be functionalized or unfunctionalized. 60 In particular, the alkyl group is C1-C 45 groups, and more particularly, C1-C 30 As used herein, the term alkyl refers to a C1-C4 group.

[0040] The term "branched" refers to any molecular structure that is not a straight chain. The term includes branched and hyperbranched structures.

[0041] The term "cosmetically acceptable ingredient" refers to any ingredient / compound or mixture of ingredients / compounds or combination of ingredients / compounds commonly used in personal care compositions to produce some other desired effect.

[0042] As used herein, the term "cosmetic / dermatological composition" is intended to describe compositions for topical application to human skin, including leave-on and wash-off products.

[0043] The terms "effective amount" and "effective use level" refer to a sufficient amount of a functional active agent or solubilizing agent to provide desired performance attributes, stability, efficacy, product aesthetics, and the like.

[0044] The term "hypoallergenic" is to be understood in a broad sense as compounds having reduced irritation and which do not sensitize the skin or hair after topical application.

[0045] The term "odorless" should be understood in a broad sense as the property of a substance not having any special odor or smell.

[0046] The term "freeze-thaw stable" as used herein refers to a stability test in which a test sample is subjected to low temperatures as low as 0° C. and then the sample is thawed to temperatures as high as 95° C. This test describes the ability of a product to remain stable under varying temperature conditions.

[0047] As used herein, the term "functional active" refers to, for example, chemically active, pharmaceutically active or nutritionally active ions, molecules, complexes or polymers. It includes personal care, cosmetic, pharmaceutical and nutritionally active compounds. Preferably, the functional active is a sunscreen containing UVA and / or UVB active organic or mineral photoprotective agents, which are water-soluble or fat-soluble or insoluble in commonly used cosmetic solvents.

[0048] The terms "personal care composition" and "cosmetic" refer to compositions intended for use on or in the human body, such as skin, sun, hair, oral, makeup, eyebrow, eyelash and preservative compositions, including those that alter the color and appearance of the skin and hair.

[0049] The term "pharmaceutical composition" means any composition comprising at least one pharmaceutically active ingredient, as well as any product resulting directly or indirectly from the combination, complexation or aggregation of any two or more ingredients, from the dissociation of one or more ingredients, or from any other type of reaction or interaction of one or more ingredients.

[0050] The term "pharmaceutical active" should be broadly understood to include any active ingredient that is believed to have a therapeutic effect when delivered to an individual in need thereof, and is further regulated by drug regulatory agencies such as CDER, EMEA or TAG, etc. Pharmaceutical active ingredients can be taken orally for systemic effect, or act locally, such as when present in the mouth or on the skin, etc. They can also be delivered through the skin as in a transdermal drug delivery system.

[0051] The term "photoprotective composition" includes cosmetic compositions, personal care compositions, pharmaceutical compositions and / or nutritional compositions.

[0052] As used herein, the term "photoprotection" refers to the ability of a functional active, preferably a sunscreen active, to maintain its integrity when exposed to sunlight when combined with a cycloalkyltoluate-based compound. Photoprotective compositions typically have an SPF (sun protection factor), for example, of at least 6, preferably at least 30, 45, 60 or 100. SPF is formally defined in "A new substrate to measure sunscreen protection factors throughout the ultraviolet spectrum", J. Soc. Cosmet. Chem., 40, 127-133, 1989, which is incorporated herein by reference in its entirety.

[0053] As used herein, the term "photostable" refers to the ability of a molecule to remain intact under radiation.

[0054] The term "skin" as used herein includes the skin on the face, neck, chest, back, abdomen, arms, hands, legs, feet, and scalp.

[0055] As used herein, the term "SPF" refers to the sun protection factor (SPF) - defined as the amount of sun protection factor (SPF) when 2 mg / cm 2 The UVR dose required to produce 1 minimal erythema dose (MED) on protected skin after product application is divided by the UVR required to produce 1 MED on unprotected skin.

[0056] The term "sun care composition" refers to any composition intended for use on the human body for protection against harmful or undesirable radiation from the sun's rays.

[0057] The personal care industry needs improved cosmetic and dermatological compositions, particularly those containing sunscreens or sunscreen actives. One of the greatest technical challenges of sunscreen compositions is to effectively and completely dissolve the functional actives, which are typically lipophilic, while providing protection against harmful UV radiation. The present application provides an effective means to meet the above unmet needs.

[0058] Described herein are photoprotective topical compositions comprising: at least one functional active and at least one cycloalkyltoluate-based solubilizing compound, wherein the solubilizing compound is present in an amount effective to dissolve the functional active. In addition, the photoprotective topical composition is visually clear, odorless, and freeze-thaw stable.

[0059] According to the present invention, there is provided a photoprotective topical composition comprising: (i) at least one functional active; and (ii) at least one solubilizing compound having Formula I:

[0060]

[0061] Where R is C5-C 10 Cycloalkyl or linear or branched alkylcycloalkyl, wherein the ring size is C5-C7; R1, R2 and R3 are H or linear or branched C1-C4 alkyl, provided that at least two of R1, R2 and R3 are H; wherein the solubilizing compound is present in an amount effective to dissolve the functional active.

[0062] Therefore, " effective amount " is the amount of at least one solubilizing compound (or solubilizing agent) required for dissolving at least one functional active. The solubilizing compound of the present application is present in an effective amount of about 0.1%wt. / wt. to about 70%wt. / wt. of the total composition. Other non-limiting ranges of solubilizing compounds include 0.1% to 1%, 1% to 5%, 5% to 10%, 10% to 15%, 15% to 20%, 20% to 25%, 25% to 30%, 30% to 50% or 50% to 70%. However, the preferred range of the solubilizing compound for dissolving at least one functional active is about 5%wt. / wt. to 10%wt. / wt. of the total composition.

[0063] In a preferred embodiment, the application provides at least one solubilizing compound (or solubilizing agent) for dissolving functional actives, wherein the solubilizing compound belongs to the class of cycloalkyltoluates. Non-limiting but preferred solubilizing compounds may be selected from 2-cyclohexyltoluate, 3-cyclohexyltoluate, 4-cyclohexyltoluate, 3-cyclohexylmethyltoluate, 3-cyclopentyltoluate and m-cycloheptyltoluate, alone or in combination. Representative structures of these non-limiting compounds may include:

[0064]

[0065] According to another preferred and non-limiting embodiment, the composition of the present application includes a combination or mixture of cyclohexyl m-toluate (cyclohexyl 3-toluate) and cyclohexyl p-toluate (cyclohexyl 4-toluate) in a ratio of about 70:30 to about 5:95, preferably a ratio of about 10 to about 90. This combination advantageously simplifies the formulation system because it does not require any heating or homogenization before use, and is therefore freeze-thaw stable.

[0066] In another specific and non-limiting embodiment, the present application provides a photoprotective topical composition, wherein the composition is a personal care composition, a cosmetic care composition, a dermatological care composition, a pharmaceutical composition or a nutritional care composition. Preferably, the composition is a personal care composition.

[0067] Non-limiting examples of personal care compositions include sunscreen compositions, facial care compositions, lip care compositions, eye care compositions, skin care compositions, after-sun care compositions, body care compositions, nail care compositions, anti-aging compositions, insect repellents, oral care compositions, deodorant compositions, hair care compositions, conditioning compositions, color cosmetic compositions, color care compositions, self-tanning compositions, and foot care compositions. In another non-limiting embodiment, the personal care composition is a sunscreen composition, more particularly, the sunscreen composition is a highly effective photostabilizing and photoprotective composition.

[0068] In another non-limiting embodiment, the present application provides sunscreen compositions, for example, formulated for application to the lips, hair, face, cheeks, neck, area around the eyes, entire hands and body areas. Additionally, self-tanning compositions are products that color the skin without requiring full sun exposure and are considered within the sunscreen category.

[0069] In yet another specific and non-limiting embodiment, the present application provides a functional active selected from the group consisting of a personal care active, a cosmetic active, a nutritional active, and a pharmaceutical active.

[0070] Thus, the functional actives used in the present application are present in an amount of about 1% wt. / wt. to about 90% wt. / wt. of the total composition. Other non-limiting ranges of functional actives include 1% to 5%, 5% to 10%, 10% to 15%, 15% to 20%, 20% to 25%, or 25% to 30%, 30% to 40%, 40% to 50%, 50% to 60%, 60% to 70%, 70% to 80%, and 80% to 90%.

[0071] In one non-limiting embodiment, preferred functional actives are sunscreen actives, which contain UVA and / or UVB actives and organic or mineral photoprotectants, which are water-soluble, lipid-soluble or insoluble in commonly known cosmetic solvents.

[0072] Non-limiting examples of UV actives include organic and inorganic substances that scatter, absorb and / or reflect radiation with a wavelength of about 100nm to about 400nm. In a special and non-limiting aspect, sunscreen compositions protect against UV-A, UV-B and / or UV-C radiation. UV-A radiation, from about 320nm to about 400nm, has the longest wavelength in the UV spectrum and is therefore the least energetic. UV-A radiation includes UV-A1 (from about 340nm to about 400nm) and UV-A2 (from about 320nm to about 340nm). UV-B radiation has a shorter wavelength, from about 290nm to about 320nm. UV-C radiation has the shortest wavelength from about 200nm to about 290nm. Suitable UV actives (or UV filters) that can be selected to be included in personal care compositions are most likely to depend on local regulations. As is well known, commercially available sunscreens typically contain a combination of multiple sunscreen actives.

[0073] Non-limiting examples of sunscreens (UV actives) useful herein include octyl salicylate; para-aminobenzoic acid, PEG-25 PABA, ethylhexyl dimethyl PABA, pentyl dimethyl PABA, octyl dimethyl PABA, amyl dimethyl PABA, benzophenone-1, benzophenone-2, benzophenone-3, benzophenone-4, benzophenone-5, benzophenone-6, benzophenone-8, benzophenone-9, 2-(2H-benzotriazol-2-yl)-4,6-di-tert-amylphenol, ethyl 2-cyano-3,3-diphenylacrylate, trimethylcyclohexyl salicylate (homo menthylsalicylate), bis-ethylhexyloxyphenol methoxyphenyl triazine (bemotrizinol), (1,2,2,6,6-pentamethyl-4-piperidinyl) sebacate methyl ester, 2-(2H-benzotriazol-2-yl)-4-methylphenol, diethylhexyl butyramido triazone, 4,6-bis-(octylthiomethyl) o-cresol, poly (4-hydroxy-2,2,6,6-tetramethyl-1-piperidinylethanol-alt-1,4-butanedioic acid), red petroleum, octyl cyanoacrylate, isopropyl para-methoxycinnamate Amyl ester, drometrizole, drometrizole trisiloxane, bisoctrizole, 2,4-di-tert-butyl-6-(5-chloro-2H-benzotriazol-2-yl)-phenol, 2-hydroxy-4-octyloxybenzophenone, methyl diisopropylcinnamate, 2-(1,1-dimethylethyl)-6-[[3-(1,1-dimethylethyl)-2-hydroxy-5-methylphenyl]methyl-4-methylphenyl-acrylate, menthyl anthranilate, butyl methoxydibenzoylmethane, 2-ethoxyethyl p-methoxycinnamate, benzylidene camphor Brain sulfonic acid, dimethoxyphenyl-[1-(3,4)]-4,4-dimethyl-1,3-pentanedione, N,N'-hexane-1,6-diylbis-[3-(3,5-di-tert-butyl-4-hydroxyphenylpropionamide)], pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, 2,6-di-tert-butyl-4-[4,6-bis(octylthio)-1,3,5-triazine-2-ylamino]phenol, 2-(2H-benzotriazol-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol, tri Ethanolamine salicylate, diethanolamine p-methoxycinnamate, polysilicone-15, 4-methylbenzylidene camphor, n-phenylaniline, reaction products with 2,4,4-trimethylpentene, (2-ethylhexyl)-2-cyano-3,3-diphenylacrylate, digalloyl trioleate, polyacrylamidomethylbenzylidene camphor, glyceryl ethylhexanoate dimethoxycinnamate, 1,3-bis-[(2'-cyano-3',3'-diphenylacryloyl)oxy]-2,2-bis-{[(2'-cyano-bis-(2,2,6,6-tetramethyl-4-piperidinyl)-sebacate, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, hexamethylenediamine, ethyl 4-bis(hydroxypropyl)aminobenzoate, 6-tert-butyl-2-(5-chloro-2H-benzotriazol-2-yl)-4-methylphenol, 3,3',3″,5,5',5″-hexa-tert-butyl-α-α'-α″ -(Mesitylene-2,4,6-triyl)tri-p-cresol, ethylhexyl dimethoxybenzylidene dioxoimidazolinyl propionate, N,N'-diformyl-N,N'-bis-(2,2,6,6-tetramethyl-4-piperidinyl), 3-benzylidene camphor, terephthalylidene camphor sulfonic acid, camphor benzalkonium methosulfate, bisdisulizole disodium, etocrylene, ferulic acid, 2-(2H-benzotriazol-2-yl)- 4-(1,1,3,3-tetramethylbutyl)-phenol, 4,6-di(dodecylthiomethyl)-o-cresol, β-2-pyranose glucopyranose oxypropyl hydroxybenzophenone, phenylbenzimidazole sulfonic acid, diethylamino hydroxybenzoyl benzoic acid hexyl ester, 3',3'-diphenylacryloyl)oxy]methyl}-propane, ethylhexyl p-methoxycinnamate, avobenzone, camphor benzalkonium methosulfate, phenylbenzimidazole sulfonic acid, terephthalylidene Dicamphor sulfonic acid, benzylidene camphor sulfonic acid, polyacrylamidomethylbenzylidene camphor, ethylhexyl methoxycinnamate, ethylhexyl triazone, diethylhexyl butyramido triazone, 4-methylbenzylidene camphor, 3-benzylidene camphor, methylene-bis-benzotriazolyl tetramethylbutylphenol, disodium phenyl dibenzimidazole tetrasulfonate, bisethylhexyloxyphenol methoxyphenol triazine, polysilicone-15, 2,4,6-tris (4-aminobenzylidene malonate diisobutyl)-s-triazine, inorganic sunscreen selected from titanium dioxide and zinc oxide; micronized or non-micronized mixtures thereof. As described, it is contemplated that these actives may be used in combination. ,

[0074] Sunscreen actives (UV filters) used in the present application may include one or more of the following: Bis-ethylhexyloxyphenol methoxyphenyl triazine (Bemotrizinol) (Escalol TM S UV filter (Ashland), Padimate O (Escalol TM 507 UV filter (Ashland), avobenzone (Escalol TM 517 UV filter (Ashland), Octinoxate (Escalol TM557 UV filter (Ashland), oxybenzone (Escalol TM 567 UV filter (Ashland), Sulisobenzone (Escalol TM 577 UV filter (Ashland), Octisalate (Escalol TM 587 UV filter (Ashland), Homosalate (Escalol TM HMS UV filter (Ashland) and Octocrylene (Escalol TM 597 UV filter (Ashland).

[0075] According to a particularly preferred and non-limiting embodiment, the sunscreen active or sunscreen agent is bis-ethylhexyloxyphenol methoxyphenyl triazine, available from Ashland Specialty Ingredients as S is sold. The sunscreen composition may additionally comprise at least one additional UV filter and / or a mineral photoprotectant comprising treated or untreated metal oxide pigments or nanopigments as part of the desired composition. Applicants have found that the solubilizer described herein is particularly useful in dissolving bis-ethylhexyloxyphenol methoxyphenyl triazine, which is known to be difficult to dissolve.

[0076] In another preferred embodiment, the present application discloses a photoprotective topical personal care composition, wherein the composition is visually clear, odorless, and freeze-thaw stable.

[0077] According to one specific embodiment of the present application, the composition is "visually transparent" because the composition can be applied to a substrate and light energy passes through the composition with little or no distortion, so that the substrate can be clearly seen through the composition with the eye. Transparency is measured using methods known to those skilled in the art. In this specification, the measurement of total absorbance is used to demonstrate the level of transparency achieved using various embodiments of the claimed composition.

[0078] According to another specific embodiment of the present application, the composition of the present invention is "odorless" because it was found to be acceptable when a panel of odor evaluation experts conducted a comparative study of sunscreen compositions containing cyclohexyl toluate and bis-ethylhexyloxyphenol methoxyphenyl triazine. Cyclohexyl toluate has been found to have a comparable odor preference and odor acceptance rating to commercially available solubilizer C12-15 alkyl benzoate. Only a low odor was observed even after aging.

[0079] In another specific embodiment, the present application further comprises at least one auxiliary agent or additive or additional ingredient selected from a second polymer for improving water resistance, oils, waxes, solvents, emulsifiers, preservatives, antioxidants, vitamins, perfumes, insect repellents, dyes, pigments, fillers, film formers, buffers, spreaders, pearlescent agents, electrolytes, acids, bases, fatty substances, organic solvents, ionic or nonionic, hydrophilic or lipophilic thickeners, softeners, wetting agents, opacifiers, emollients, fragrances, anionic surfactants, cationic surfactants, nonionic surfactants, zwitterionic surfactants The invention also includes but is not limited to: agents, amphoteric surfactants, active agents, polymers, propellants, antioxidants, anti-free radical agents, alpha-hydroxy acids, humectants, anti-inflammatory agents, colorants, pharmaceutically or dermatologically or cosmetically acceptable excipients, skin care agents or hair care agents, hair styling agents, hair fixatives, structurants, gelling agents, viscosity modifiers, electrolytes, pH modifiers, organosilicone compounds, anti-dandruff agents, defoaming agents, anti-frizzing agents, penetrants, conditioning agents, chelating agents, antimicrobial agents, UV absorbers, natural extracts, carriers, diluents, solvents, pharmaceutical actives, lubricants, combing aids, plasticizers, solubilizers, neutralizers, vapor pressure suppressants, bleaching agents, hydrating agents, cosmetic adjuvants and / or additives, protective agents and mixtures thereof.

[0080] Non-limiting examples of suitable antioxidants and / or anti-free radical protectants include: BHA (tert-butyl-4-hydroxyanisole), BHT (2,6-di-tert-butyl-p-cresol), TBHQ (tert-butylhydroquinone), proanthocyanidin oligomers, flavonoids, tetraaminopiperidine, isoascorbic acid, spermine, cysteine, glutathione, superoxide dismutase, lactoferrin, and mixtures thereof.

[0081] Non-limiting examples of inorganic photoprotective agents are selected from pigments of treated or untreated metal oxides, preferably nanopigments (average size of primary particles: generally 5 nm to 10 nm, preferably 1 nm to 5 nm), the metal oxides being selected from titanium oxide (amorphous or crystalline in the form of rutile and / or anatase), iron oxide, zinc oxide, zirconium oxide or cerium oxide.

[0082] The additional photoprotective agent is typically present in the composition according to the present application in a proportion of 0.01% wt. / wt. to 70% wt. / wt. of the total composition. Other non-limiting ranges of additional photoprotective agents include 0.01% to 1% by weight, 1% to 5% by weight, 5% to 10% by weight, 10% to 15% by weight, 15% to 20% by weight, 20% to 25% by weight, or 25% to 30% by weight, 30% to 40% by weight, 40% to 50% by weight, 50% to 60% by weight, and 60% to 70% by weight of the total composition, preferably 0.01% wt. / wt. to 10% wt. / wt. of the total composition.

[0083] Non-limiting examples of suitable preservatives include: benzoic acid, sorbic acid, dehydroacetic acid, diazolidinyl ureas, imidazolidinyl ureas, salicylic acid, piroctone olamine, DMDM ​​hydantoin, IPBC (iodopropynyl butylcarbamate), triclosan, bronopol, formaldehyde, isothiazolinone, nitrate / nitrite, parabens, phenoxyethanol, potassium sorbate, sodium benzoate, sulfites, sulfur dioxide and mixtures thereof. Preferred preservatives include methylparaben, ethylparaben, propylparaben, phenoxyethanol, benzoic acid and dehydroacetic acid. Non-limiting ranges of preservatives include 0.1% wt. / wt. to 10% wt. / wt. of the total composition weight. Other non-limiting ranges include 0.1 wt % to 2 wt %, 2 wt % to 4 wt %, 4 wt % to 6 wt %, 6 wt % to 8 wt %, or 8 wt % to 10 wt % of the total composition.

[0084] Physiologically and cosmetically acceptable medium can be composed of water, cosmetically acceptable solvent or mixture of water and cosmetically acceptable solvent only, for example, lower alcohol composed of C1 to C4, such as ethanol, isopropanol, tert-butyl alcohol, n-butyl alcohol, alkylene glycol (such as propylene glycol) and glycol ether. Preferred carriers or medium are denatured ethanol, water, propylene glycol, ethanol, trimethylamine and glycerol. The carrier is present in an amount of about 2% wt. / wt. to about 90% wt. / wt. of the total topical composition. Other non-limiting ranges of the carrier include 5% to 10% by weight, 10% to 15% by weight, 15% to 20% by weight, 20% to 25% by weight or 25% to 30% by weight, 30% to 40% by weight, 40% to 50% by weight, 50% to 60% by weight, 60% to 70% by weight, 70% to 80% by weight and 80% to 90% by weight of the total composition.

[0085] The non-limiting examples of suitable vitamins include ascorbic acid (vitamin C), vitamin E, vitamin E acetate, vitamin E phosphate, B vitamins (such as B3 and B5), niacin, vitamin A, derivatives thereof, and mixtures thereof. The non-limiting range of vitamins includes 0.1% to 10% by weight of the total composition. Other non-limiting ranges include 0.1% to 2% by weight, 2% to 4% by weight, 4% to 6% by weight, 6% to 8% by weight, or 8% to 10% by weight of the total composition.

[0086] The non-limiting examples of surfactants include anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants or zwitterionic surfactants. The non-limiting range of surfactants includes 0.1% wt. / wt. to 10% wt. / wt. of the total composition. Other non-limiting ranges include 0.1% to 2% by weight, 2% to 4% by weight, 4% to 6% by weight, 6% to 8% by weight or 8% to 10% by weight of the total composition.

[0087] Non-limiting examples of anionic surfactants used herein include water-soluble salts of alkyl sulfates having 8 to 20 carbon atoms in the alkyl group (e.g., sodium alkyl sulfate) and water-soluble salts of sulfonated fatty acid monoglycerides having 8 to 20 carbon atoms, selected from sarcosinates, taurates, isethionates, sodium lauryl sulfoacetate, sodium laureth carboxylate, sodium dodecylbenzenesulfonate, sodium and potassium lauroyl sarcosine, sodium and potassium myristoyl sarcosine, sodium and potassium palmitoyl sarcosine, sodium and potassium stearoyl sarcosine, and sodium and potassium oleoyl sarcosine. Preferred anionic surfactants are selected from sodium lauryl sulfate (SLS) and sodium coco monoglyceride sulfonate.

[0088] Non-limiting examples of suitable cationic surfactants include derivatives of fatty quaternary ammonium compounds having at least one long alkyl chain containing from about 8 to about 18 carbon atoms, for example, lauryl trimethyl ammonium chloride, cetyl pyridinium chloride, cetyl trimethyl ammonium bromide, diisobutyl phenoxyethyl dimethyl benzyl ammonium chloride, coconut oil alkyl trimethyl ammonium nitrite, cetyl pyridinium fluoride and mixtures thereof. Further suitable are quaternary ammonium fluorides having detergent properties, such as compounds described in U.S. Pat. No. 3,535,421. Certain cationic surfactants are used as bactericides in the compositions disclosed herein.

[0089] Non-limiting examples of suitable nonionic surfactants include: Poloxamers (available from BASF Corporation under the trade name The invention discloses a kind of ethylene oxide condensates of fatty alcohols, polyethylene oxide condensates of alkylphenols, products obtained by condensing ethylene oxide with the reaction products of propylene oxide and ethylenediamine, ethylene oxide condensates of fatty alcohols, long-chain tertiary amine oxides, long-chain tertiary phosphine oxides, long-chain dialkyl sulfoxides and mixtures thereof.

[0090] Non-limiting examples of suitable zwitterionic surfactants include derivatives of betaines and fatty quaternary ammonium compounds, wherein the fatty radical may be linear or branched, and which contain an anionic water-solubilizing group, for example, carboxyl, sulfonate, sulfate, phosphate or phosphonate.

[0091] The non-limiting examples of suitable betaines include: decyl betaine or 2-(N-decyl-N, N-dimethylamino) acetate, coco betaine or 2-(N-cocoyl-N, N-dimethylamino) acetate, myristyl betaine, palmityl betaine, lauryl betaine, cetyl betaine, stearyl betaine and mixtures thereof. Examples of amido betaines are cocoamidoethyl betaine, cocoamidopropyl betaine, lauroamidopropyl betaine and the like. Selected betaines include cocoamidopropyl betaine, such as lauroamidopropyl betaine. Suitable betaine surfactants are disclosed in U.S. Patent No. 5,180,577.

[0092] Non-limiting examples of commercially available surfactants include: (1) alkanolamides, sold under the trade name Amidex TM and Schercomid TM ; Amido-amine, trade name Katemul TM and Schercodine TM ; Amine oxide, trade name Chemoxide TM and Schercamox TM ; Amphoteric surfactant, trade name Chembetaine TM , Schercotaine TM and Schercoteric TM ; Imidazolin, trade name Schercozoline TM ; Pearlescent agent, trade name Quickpearl TM ; Performance concentrates, trade name Sulfochem TM and Chemoryl TM ; Soaps (potassium cocoate and potassium soyaate); specialty ethoxylates sold under the trade name Chemonic TM ; Specialty quats, trade name QuatrexTM and Schercoquat TM ; Sulfate, trade name Sulfochem TM ; and sulfosuccinate, sold by Lubrizol under the trade name Chemccinate TM ; (2) Avaniel, BASF Corp. and (3) Rhodia SLB, Bab, Ultra SI, Ultra and Plaisant. (4)Stepan Company’s Pearl2, Pearl 4, Pearl Series, M-20, PTC, 2CSF, Stepan- GCC, SLL-FB, AM, PB, Alpha- BSS-45, Bio- 804, Stepan- L3, SLL-FB, SSL-CG and CFAS-70.

[0093] Also suitable as surfactants are those described in the book Surfactants in Personal Care Products and Decorative Cosmetics, 3rd edition, 2006, published by CRC. This publication is incorporated herein by reference in its entirety.

[0094] Non-limiting examples of skin conditioning agents include isodecyl neopentanoate, dicaprylyl carbonate, 2-ethylhexyl isononanoate, coco-octanoate caprate, and isodecyl salicylate. Non-limiting ranges of skin conditioning agents include 0.1% wt. / wt. to 10% wt. / wt. of the total composition. Other non-limiting ranges include 0.1% to 2%, 2% to 4%, 4% to 6%, 6% to 8%, or 8% to 10% by weight of the total composition.

[0095] Non-limiting examples of lubricants used herein are selected from cyclopentasiloxane, diisopropyl adipate and isocetyl alcohol. Non-limiting ranges of lubricants include 0.1% wt. / wt. to 10% wt. / wt. of the total composition. Other non-limiting ranges include 0.1% to 2% by weight, 2% to 4% by weight, 4% to 6% by weight, 6% to 8% by weight, or 8% to 10% by weight of the total composition.

[0096] Non-limiting examples of emollients include lauryl lactate, C12-15 alkyl lactate, methyl glucose sesquistearate, and PEG-20 methyl glucose sesquistearate. Non-limiting ranges of emollients include 0.1% wt. / wt. to 10% wt. / wt. of the total composition weight. Other non-limiting ranges include 0.1% to 2% by weight, 2% to 4% by weight, 4% to 6% by weight, 6% to 8% by weight, or 8% to 10% by weight of the total composition.

[0097] The non-limiting examples of suitable silicones include polyalkylsiloxanes, polyarylsiloxanes, polyalkylarylsiloxanes, silicone gums and resins, polyorganosiloxanes modified by organic functional groups and mixtures thereof. Preferred silicones include polymethylsiloxanes, octyl polymethylsiloxanes and cetyl polydimethylsiloxanes. The non-limiting range of silicones includes 0.1% wt. / wt. to 10% wt. / wt. of the total composition. Other non-limiting ranges include 0.1% to 2% by weight, 2% to 4% by weight, 4% to 6% by weight, 6% to 8% by weight or 8% to 10% by weight of the total composition.

[0098] Non-limiting examples of emulsifiers include ethoxylated fatty acids, ethoxylated glycerides, ethoxylated oils, ethoxylated sorbitan esters, fatty esters, PEG esters, and polyglycerol esters. Preferred emulsifiers are glyceryl stearate (and) laureth-23 (1%). Non-limiting ranges of emulsifiers include 0.1% wt. / wt. to 10% wt. / wt. of the total composition. Other non-limiting ranges include 0.1% to 2% by weight, 2% to 4% by weight, 4% to 6% by weight, 6% to 8% by weight, or 8% to 10% by weight of the total composition.

[0099] Non-limiting examples of buffers used in the present application include carbonates, phosphates, bicarbonates, citrates, borates, acetates, anhydrides and succinates of alkali metals or alkaline earth metals, such as sodium phosphate, sodium citrate, sodium borate, sodium acetate, sodium bicarbonate and sodium carbonate. Non-limiting ranges of buffers include 0.1% wt. / wt. to 10% wt. / wt. of the total composition weight. Other non-limiting ranges include 0.1% to 2% by weight, 2% to 4% by weight, 4% to 6% by weight, 6% to 8% by weight or 8% to 10% by weight of the total composition.

[0100] Non-limiting examples of other additives useful herein include Ceteareth-20, Hydrogenated Polydecene (and) Trideceth-6, Cetyl Alcohol, and Caprylyl Methicone to impart a desired feel and smoothness to the product.

[0101] Non-limiting examples of tanning agents or browning agents used in the present application include dihydroxyacetone, isatin, alloxan, ninhydrin, glyceraldehyde, mesotartaric aldehyde, glutaraldehyde, erythrulose, pyrazoline-4,5-dione derivatives, 4,4-dihydroxypyrazoline-5 and its derivatives. Non-limiting ranges of tanning agents or browning agents include 0.1% wt. / wt. to 10% wt. / wt. of the total composition weight. Other non-limiting ranges include 0.1% to 2% by weight, 2% to 4% by weight, 4% to 6% by weight, 6% to 8% by weight, or 8% to 10% by weight of the total composition.

[0102] In another specific embodiment, the application provides a photoprotective topical composition formulated as an oil-in-water emulsion, a water-in-oil emulsion, an oil-water-oil emulsion, a water-oil-water emulsion, a water-in-silicone emulsion, an oil solution, a lipid fusion, a hydroalcoholic gel, an anhydrous formulation, an anhydrous spray, an anhydrous gel, an anhydrous xerogel, an aqueous gel, a gel cream SPF 20, an SPF 30 cream, an alcoholic solution, a hydroalcoholic solution, an emulsion, a lotion, a powder, a stick, a roll-on, a spray, a wipe, a wax, a mousse, an aerosol, a cream, a patch, a pomade, a pump spray, a solution, a towelette, a paste, a powder or a spray.

[0103] Non-limiting examples of skin care formulations of the present application include solutions, oils, lotions, creams, ointments, liquids, gels, solids, W / O emulsions, O / W emulsions, emulsions, suspensions, microemulsions, dispersions, microencapsulated products, sticks, creams, tonics, pastes, mists, reconstitutable products, peels, soaps, aerosols, mousses, waxes, gels, pomades, sprays, putties, lacquers, serums, perms, powders, pencils, flakes, blushers, highlighters, bronzers, concealers and 2-way cake products. The compositions of the present application include skin cleansing compositions, particularly in the form of solutions or gels, for bathing or showering, or makeup removal products.

[0104] The six product categories offered below are included under the skin care grouping.

[0105] Eye Care – Non-limiting eye care product forms include: mascara, eyeliner, eyeshadow, eyelash curler, eyebrow pencil, and eyeliner.

[0106] Lip Care—Non-limiting lip care product forms include: lipsticks, lip balms, lip liners, lip glosses, lip sprays, clear lip bases, tinted lip balms, and multi-purpose color sticks that can also be used on the cheeks and eyes.

[0107] Nail Care - Non-limiting nail care product forms include: nail polishes, nail vamishes, enamels, nail polish removers, home manicure products (such as cuticle softeners and nail strengtheners), and artificial nails.

[0108] Facial Treatments—Non-limiting facial treatment product forms include: creams, lotions, solutions, oils, liquids, peels, scrubs, emulsions, suspensions, microemulsions, microencapsulated products, pastes, rehydratable products, aerosols, mousses, gels, waxes, glues, pomades, sprays, facial wipes, hardeners, lacquers, serums, perms, powders, blushes, highlighters, bronzers, masks, and concealers.

[0109] Body Care - Non-limiting body care product forms include: foams, peels, masks, gels, bars, aerosols, lotions, salts, oils, balls, liquids, powders, peels, pearls, bar soaps, liquid soaps, body washes, cleansers, scrubs, creams, sheets, other bath and shower products, shaving products, waxing products, and disinfectants.

[0110] Foot Care—Non-limiting foot care product forms include: mousses, creams, lotions, powders, liquids, sprays, aerosols, gels, sheets, and scrubs.

[0111] The photoprotective compositions of the present invention are capable of protecting human skin from the harmful effects of solar radiation.

[0112] It is also contemplated that the personal care compositions are used in male and / or female personal grooming and / or hygiene products selected from sanitary napkins, baby diapers, adult diapers, feminine products, incontinence products, and other related products.

[0113] In yet another specific embodiment, the present application provides a photoprotective topical sunscreen composition for UV-light protection of human skin and / or hair, comprising: (a) from about 1% wt. / wt. to about 70% wt. / wt. of at least one active sunscreen; (b) from about 0.1% wt. / wt. to about 50% wt. / wt. of at least one solubilizing compound selected from 3-cyclohexyl toluate, 4-cyclohexyl toluate, or a combination thereof; and (c) from about 1% wt. / wt. to about 80% wt. / wt. of at least one topically-applicable, cosmetically or dermatologically acceptable carrier.

[0114] The sunscreen composition of the present invention may also include a polymer selected from α-olefin / polyvinyl pyrrolidone (Ganex series from Ashland Specialty Ingredients) and vinyl acetate: monobutyl maleate: isobornyl acrylate (Advantage-Plus series from Ashland Specialty Ingredients) for enhancing the performance and feel of the sunscreen composition. The addition of these polymers shows an increased critical wavelength and UVA / UVB absorbance ratio.

[0115] In yet another specific embodiment, the present application provides a method for cosmetic treatment or care of the skin, lips, nails, hair, ears, eyelashes, eyebrows and / or scalp, comprising topically applying thereon an effective amount of a photoprotective topical composition comprising (i) at least one functional active; and (ii) at least one solubilizing compound having Formula I:

[0116]

[0117] Where R is C5-C 10 Cycloalkyl or linear or branched alkylcycloalkyl, wherein the ring size is C5-C7; R1, R2 and R3 are each independently selected from H and linear or branched C1-C4 alkyl, provided that at least two of R1, R2, R3 are H; wherein the solubilizing compound is present in an amount effective to dissolve the functional active.

[0118] In yet another specific embodiment, the present application provides a method for photoprotecting exposed and / or unexposed skin, nails, hair, lips, ears, eyebrows, eyelashes and / or scalp from the damaging effects of UV-radiation, comprising topically applying thereto an effective amount of a cosmetic / dermatological composition comprising: (i) at least one functional active; and (ii) at least one solubilizing compound having Formula I:

[0119]

[0120] Where R is C5-C 10 Cycloalkyl or linear or branched alkylcycloalkyl, wherein the ring size is C5-C7; R1, R2 and R3 are each independently selected from H and linear or branched C1-C4 alkyl, provided that at least two of R1, R2, R3 are H; wherein the solubilizing compound is present in an amount effective to dissolve the functional active.

[0121] In order to further illustrate the present application and its advantages, the following specific examples are given, which should be understood to be exemplary and non-restrictive. In the following examples described, unless otherwise indicated, all parts and percentages are given by weight.

[0122] Example 1: Synthesis of cyclohexyl 3-toluate

[0123] Cyclohexyl 3-toluate is prepared by reacting cyclohexanol with 3-toluic acid in the presence of a catalyst (eg, a Lewis acid catalyst and / or an organic catalyst / inorganic catalyst).

[0124]

[0125] To a dry 2-L, 4-neck round bottom flask equipped with a mechanical stirrer, heating mantle / temperature controller / thermocouple, Dean-Stark separator with reflux condenser and feed port was added 601.0 g (6.0 mol) of warm cyclohexanol at 50-80°C and mixed with 3.3 g of Lewis acid catalyst. The contents of the flask were heated to 80-110°C and 680.8 g (5.0 mol) of 3-toluic acid was added to the flask under stirring. The reaction mixture was heated to 230-232°C and the reaction water was removed. The final reaction mixture with an acid value of ≤1 mg KOH / g was distilled under vacuum. Yield of cyclohexyl 3-toluate: 93%. Purity: 99.6%. Solubility of Escalol S at 25°C: 35% & Solubility of Avobenzone at 25°C: 26%.

[0126] Example 2: Synthesis of 4-cyclohexyl toluate

[0127] Cyclohexyl 4-toluate is prepared by reacting cyclohexanol with 4-toluic acid in the presence of a catalyst (eg, a Lewis acid catalyst and / or an organic catalyst / inorganic catalyst).

[0128]

[0129] The reaction was carried out as described above. 601.0 g (6.0 mol) of warm cyclohexanol, 3.3 g of Lewis acid catalyst and 680.8 g (5.0 mol) of 4-toluic acid were added to a flask. The reaction mixture was heated to 230-232°C and the reaction water was removed. The final reaction mixture with an acid value of 1.1 mg KOH / g was distilled under vacuum. Yield of cyclohexyl 4-toluate: 90%. Purity: 99.7%. Solubility of Escalol S at 25°C: 36% & Solubility of Avobenzone at 25°C: 26%.

[0130] Example 3: Synthesis of cyclohexyl 2-toluate

[0131] Cyclohexyl 2-toluate is prepared by reacting cyclohexanol with 2-toluic acid in the presence of a catalyst (e.g., a Lewis acid catalyst and / or an organic catalyst / inorganic catalyst). A dry 1-L, 4-neck round bottom flask equipped with a mechanical stirrer, a heating mantle / temperature controller / thermocouple, a Dean-Stark separator with a reflux condenser, and a feed port is charged with 300.5 g (3.0 mol) of cyclohexanol, 1.6 g of a Lewis acid catalyst, and 340.4 g (2.5 mol) of 2-toluic acid. The reaction mixture is heated to 230-232° C. and the reaction water is removed. The final reaction mixture having an acid value of 3.6 mg KOH / g is distilled under vacuum. Yield of cyclohexyl 2-toluate: 94%. Purity: 99.4%; solubility of Escalol S at 25° C.: 37%; solubility of avobenzone at 25° C.: 23%.

[0132]

[0133] Example 4: Synthesis of Cyclohexyl Toluate (Mixture of Cyclohexyl 3-Toluate and Cyclohexyl 4-Toluate)

[0134] The cyclohexyl toluate mixture is prepared by reacting cyclohexanol with a mixture of 3-toluic acid and 4-toluic acid in the presence of a catalyst (eg, a Lewis acid catalyst and / or an organic catalyst / inorganic catalyst).

[0135]

[0136] The reaction was carried out as described above. 601.0 g (6.0 mol) of warm cyclohexanol, 3.3 g of Lewis acid catalyst and 680.8 g (5.0 mol) of a mixture of 3-toluic acid and 4-toluic acid were added to a flask. The reaction mixture was heated to 230-232°C and the reaction water was removed. The final reaction mixture with an acid value of <1 mg KOH / g was distilled under vacuum. Yield of cyclohexyl toluate: 94%. Purity: 99.8%. Solubility of Escalol S at 25°C: 36% & Solubility of Avobenzone at 25°C: 25%.

[0137] Example 5: Synthesis of cyclohexylmethyl 3-toluate

[0138] Cyclohexylmethyl 3-toluate is prepared by reacting cyclohexylmethanol with 3-toluic acid in the presence of a catalyst (eg, a Lewis acid catalyst and / or an organic catalyst / inorganic catalyst).

[0139]

[0140] The reaction was carried out as described above. 452.2 g (3.96 mol) of cyclohexylmethanol, 2.3 g of Lewis acid catalyst and 449.3 g (3.3 mol) of 3-toluic acid were added to a flask. The reaction mixture was heated to 230°C and the reaction water was removed. The final reaction mixture with an acid value of <1 mg KOH / g was distilled under vacuum. Yield of cyclohexylmethyl 3-toluate: 93.4%. Purity: 99.6%. Solubility of Escalol S at 25°C: 30% & Solubility of Avobenzone at 25°C: 25%.

[0141] Example 6: Synthesis of cyclopentyl 3-toluate

[0142] The cyclopentyl 3-toluate solubilizing agent is prepared by reacting cyclopentanol with 3-toluic acid in the presence of a catalyst (eg, a Lewis acid catalyst and / or an organic catalyst / inorganic catalyst).

[0143]

[0144] The reaction was carried out as described above. 375.0 g (4.4 mol) of cyclopentanol, 2.5 g of Lewis acid catalyst and 544.6 g (4.0 mol) of 3-toluic acid were added to a flask. The reaction mixture was heated to 220° C. and the reaction water was removed. The final reaction mixture, which had an acid value of 4.5 mg KOH / g, was distilled under vacuum. Yield of cyclopentyl 3-toluate: 92%. Purity: 99.5%. Solubility of Escalol S at 25° C.: 34%; Solubility of Avobenzone at 25° C.: 28%.

[0145] The physical properties of the synthesized cycloalkyl aryl esters are disclosed in Table 1, wherein the physical properties include acid value, American Public Health Association [APHA] color, refractive index and specific gravity.

[0146] Table 1: Properties of synthesized cycloalkyl aryl esters

[0147]

[0148] Example 7: Solubility of various sunscreens in different solubilizing media

[0149] Table 2: Solubility of Sunscreen Actives

[0150]

[0151] As shown in Table 2, the sunscreens show increased solubility when cyclohexyl compounds are used. Compared to X-Tend 226, which is a solubilizer for sunscreen actives in widespread commercial use, S showed more than 1.5-fold increase in solubility in the compounds of the present application.

[0152] Example 8: Comparative Study of Sunscreens with Cycloalkyl Toluates and Other Solubilizing Compounds

[0153] Different samples of the solubilizing compounds of the present invention, cycloalkyl toluate, were combined with available sunscreens Escalol S, Avobenzone, and Oxybenzone at 25°C. Testing showed clear solutions, while the samples were similar to the commercially available sunscreen solubilizer X- 226 and TN shows a crystalline structure. These results are Figure 6 The solubility of cyclohexyl esters in various sunscreen actives such as bis-ethylhexyloxyphenol methoxyphenyl triazine, ethylhexyl triazone, avobenzone & benzophenone-3 was examined in comparison with phenethyl benzoate. It was observed that cyclohexyl esters were the best solubilizers for bis-ethylhexyloxyphenol methoxyphenyl triazine, avobenzone and benzophenone-3 relative to phenethyl benzoate. Figure 2 Compared to sunscreen actives containing C12-15 alkyl benzoate as a solubilizer (which showed a solubility of about 4% to about 15%), sunscreen actives containing cyclohexyl toluate as a solubilizer showed an increased solubility percentage of about 22% to about 33%, as shown in Figure 3Similar results were observed when the sunscreen actives were screened with other esters as solubilizers (selected from phenylethyl benzoate, diisopropyl adipate, C12-15 lactate, ethylhexyl palmitate, dicaprylyl carbonate, C12-15 alkyl benzoate (and) dipropylene glycol dibenzoate (and) PPG 15 stearyl ether benzoate and dipropylene glycol dibenzoate) and compared to sunscreens containing cyclohexyl toluate, as shown in Figure 4 & Figure 5 middle.

[0154] Example 9: Expert Odor Evaluation

[0155]

[0156] The odor of sunscreens with cyclohexyl toluate and bis-ethylhexyloxyphenol methoxyphenyl triazine as solubilizers was tested by a 12-member expert panel and reported a level of odor acceptance results that was appreciable. Odor acceptance and odor preference values ​​as Figure 1 shown.

[0157] Example 10 - Formulation - Solubility Comparison

[0158]

[0159]

[0160] Sample A had cyclohexyl toluate as a solubilizing agent, and sample B had C12-15 alkyl benzoate as a solubilizing agent. When the solubility of both samples was tested, it showed that no crystals were formed in sample A, while sample B showed crystals. The results are shown in FIG. Figure 1 shown.

[0161] Example 11 - Formulation - Anhydrous Spray

[0162]

[0163] Cyclohexyl toluate (5%) was used to prepare an anhydrous spray. A clear yellow liquid was obtained.

[0164] Example 12 - Formulation - Anhydrous Spray

[0165]

[0166] Cyclohexyl toluate (5%) was used to prepare an anhydrous spray. A clear yellow liquid was obtained.

[0167] Example 13 - Formulation - Anhydrous Spray

[0168]

[0169]

[0170] Cyclohexyl toluate (3%) was used to prepare an anhydrous spray. A clear yellow liquid was obtained.

[0171] Example 14 - Formulation - Anhydrous Xerogel

[0172]

[0173] Cyclohexyl toluate (5%) was used to prepare anhydrous xerogel. Viscosity (D1): 30,000-35,000 cps as measured by (Brookfield RVT / TC / 5 rpm / 25°C / 1 min)

[0174] Example 15 - Formulation - Gel Cream SPF 20

[0175]

[0176]

[0177] Cyclohexyl benzyl alcohol (5%) was used to prepare the gel cream.Viscosity (D1): 27,000-33,000 cps measured by (Brookfield RVT / TB / 5 rpm / 25°C / 1 min) at pH 5.75-6.25.

[0178] Example 16 - Formulation - SPF 20 Cream

[0179]

[0180]

[0181] Cyclohexyl toluate (5%) was used to prepare SPF 20 cream.Viscosity (D1): 9000-1000 cps measured by (Brookfield RVT / TB / 10 rpm / 25°C / 1 min) at pH 5.30-5.70.

[0182] Example 17 - Formulation - SPF 30 Cream

[0183]

[0184] Cyclohexyl toluate (5%) was used to prepare SPF 30 cream. Viscosity: 30000-35000 cps measured by (Brookfield RVT / TB / 10 rpm / 25°C / 1 min) at pH 6.00-6.50.

[0185] Although the present invention has been described in detail with reference to certain preferred embodiments, it should be appreciated that the present invention is not limited to those precise embodiments. On the contrary, in view of the present disclosure describing the best current mode for implementing the present invention, many modifications and variations may be made by those skilled in the art without departing from the scope and spirit of the present invention.

Claims

1. A photoprotective topical composition comprising: i. at least one functional active; and ii. at least one solubilizing compound, in: The functional active is a sunscreen active selected from bemotrizinol, avobenzone and benzophenone-3, The solubilizing compound is selected from 2-cyclohexyl toluate, 3-cyclohexyl toluate, 4-cyclohexyl toluate, 3-cyclohexylmethyl toluate, 3-cyclopentyl toluate and combinations thereof, The solubilizing compound is present in an amount effective to dissolve the functional active, wherein the solubilizing compound is present in an amount of 1% wt. / wt. to 15% wt. / wt. of the total photoprotective topical composition, and the functional active is present in an amount of 1% wt. / wt. to 10% wt. / wt. of the total photoprotective topical composition.

2. The composition of claim 1, wherein the solubilizing compound is present in an amount of 1% wt. / wt. to 5% wt. / wt. of the total photoprotective topical composition.

3. The composition of claim 1, wherein the solubilizing compound is present in an amount of 5% wt. / wt. to 10% wt. / wt. of the total photoprotective topical composition.

4. The composition of claim 1, wherein the functional active is present in an amount of 1% wt. / wt. to 5% wt. / wt. of the total photoprotective topical composition.

5. The composition of claim 1, wherein the functional active is present in an amount of 5% wt. / wt. to 10% wt. / wt. of the total photoprotective topical composition.

6. The composition of claim 1, wherein the composition is visually clear and odorless.

7. The composition of claim 1, wherein the solubilizing compound is selected from the group consisting of 3-cyclohexyl toluate, 4-cyclohexyl toluate, and combinations thereof.

8. The composition of claim 1, wherein the photoprotective topical composition is a personal care composition, a pharmaceutical composition, or a nutritional composition.

9. The composition of claim 1, wherein the photoprotective topical composition is a cosmetic care composition.

10. The composition of claim 8, wherein the personal care composition is capable of exhibiting increased UV absorption retention after exposure to UV radiation.

11. The composition of claim 1 wherein the sunscreen active is bis-ethylhexyloxyphenol methoxyphenyl triazine.

12. The composition of claim 1, wherein the composition further comprises a mineral photoprotectant present in an amount of 0.01% wt. / wt. to 70% wt. / wt. of the total composition.

13. The composition according to claim 12, wherein the light protecting agent is a treated or untreated metal oxide pigment or nanopigment selected from treated or untreated titanium oxide, zinc oxide, iron oxide, zirconium oxide, cerium oxide and mixtures thereof.

14. The composition according to claim 1, wherein the composition further comprises at least one agent for artificially tanning and / or browning the skin, which is selected from dihydroxyacetone, isatin, alloxan, ninhydrin, glyceraldehyde, mesotartaric acid aldehyde, glutaraldehyde, erythrulose alone or in combination.

15. The composition according to claim 1, wherein the composition further comprises at least one adjuvant or additive selected from a second polymer for improving water resistance, a UV active solubilizer, a solvent, an emulsifier, a preservative, an antioxidant, a vitamin, an insect repellent, a wetting agent, a filler, a film former, a stabilizer, a buffer, a spreading agent, a pearlescent agent, an electrolyte, an acid, a base, a fatty substance, a softener, an emulsifier, an emollient, an antifoaming agent, a fragrance, an anionic surfactant, a cationic surfactant, a nonionic surfactant, a zwitterionic surfactant, an amphoteric surfactant, an active agent, a propellant, an acidifier or an alkalizer, an alpha-hydroxy acid, a humectant, a colorant, a pharmaceutically or dermatologically or cosmetically acceptable excipient, and a combination thereof.

16. The composition of claim 1, wherein the composition further comprises at least one adjuvant or additive selected from a second polymer for improving water resistance, a UV active solubilizer, an oil, a wax, a solvent, an emulsifier, a preservative, an antioxidant, a vitamin, an insect repellent, a dye, a pigment, a wetting agent, a filler, a thickener, a film former, a buffer, a spreading agent, a pearlescent agent, an electrolyte, an acid, a base, a softener, an opacifier, a silicone, a defoamer, a fragrance, an anionic surfactant, a cationic surfactant, a nonionic surfactant, a zwitterionic surfactant, an amphoteric surfactant, a propellant, an acidifier or an alkalizer, an alpha-hydroxy acid, a humectant, an anti-inflammatory agent, a pharmaceutically or dermatologically or cosmetically acceptable excipient, and combinations thereof.

17. The composition of claim 16, wherein the thickener is selected from the group consisting of ionic thickeners, nonionic thickeners, hydrophilic thickeners and lipophilic thickeners.

18. The composition of claim 1, wherein the photoprotective topical composition is formulated as a lipid fusion, a hydro-alcoholic gel, an anhydrous formulation, an aqueous gel, a gel-cream SPF 20, an SPF 30 cream, an emulsion, a lotion, a stick, a roll-on, a spray, a wipe, a wax, a mousse, a cream, a patch, a pomade, a solution, a towelette, a paste, or a powder.

19. The composition of claim 1, wherein the photoprotective topical composition is formulated as an oil-in-water emulsion, a water-in-oil emulsion, an oil-water-oil emulsion, a water-oil-water emulsion, a water-in-silicone emulsion, an anhydrous spray, an anhydrous gel, an anhydrous xerogel, an oil solution, an alcoholic solution, a water-alcoholic solution, an aerosol, or a spray.

20. The composition of claim 1, wherein the photoprotective topical composition is formulated as a pump spray.

21. A method for non-therapeutic cosmetic treatment or care of the skin, lips, nails, hair, ears and / or scalp comprising topically applying an effective amount of a photoprotective topical composition comprising (i) at least one functional active; and (ii) at least one solubilizing compound, in: The functional active is a sunscreen active selected from bis-ethylhexyloxyphenol methoxyphenyl triazine, avobenzone and benzophenone-3, The solubilizing compound is selected from 2-cyclohexyl toluate, 3-cyclohexyl toluate, 4-cyclohexyl toluate, 3-cyclohexylmethyl toluate, 3-cyclopentyl toluate and combinations thereof, The solubilizing compound is present in an amount effective to dissolve the functional active, wherein the solubilizing compound is present in an amount of 1% wt. / wt. to 15% wt. / wt. of the total photoprotective topical composition, and the functional active is present in an amount of 1% wt. / wt. to 10% wt. / wt. of the total photoprotective topical composition.

22. The method of claim 21, wherein the hair is eyelashes and / or eyebrows.

23. The method of claim 21, wherein the solubilizing compound is present in an amount of 1% wt. / wt. to 5% wt. / wt. of the total photoprotective topical composition.

24. The method of claim 21, wherein the solubilizing compound is present in an amount of 5% wt. / wt. to 10% wt. / wt. of the total photoprotective topical composition.

25. The method of claim 21, wherein the functional active is present in an amount of 1% wt. / wt. to 5% wt. / wt. of the total photoprotective topical composition.

26. The method of claim 21, wherein the functional active is present in an amount of 5% wt. / wt. to 10% wt. / wt. of the total photoprotective topical composition.

27. A method for the non-therapeutic purpose of photoprotecting exposed and / or unexposed skin, nails, hair, lips, ears and / or scalp from the damaging effects of UV-radiation, comprising topically applying an effective amount of a cosmetic / dermatological composition comprising: (i) at least one functional active, and (ii) at least one solubilizing compound in: The functional active is a sunscreen active selected from bis-ethylhexyloxyphenol methoxyphenyl triazine, avobenzone and benzophenone-3, The solubilizing compound is selected from 2-cyclohexyl toluate, 3-cyclohexyl toluate, 4-cyclohexyl toluate, 3-cyclohexylmethyl toluate, 3-cyclopentyl toluate and combinations thereof, The solubilizing compound is present in an amount effective to solubilize the functional active, wherein the solubilizing compound is present in an amount of 1% wt. / wt. to 15% wt. / wt. of the total composition and the functional active is present in an amount of 1% wt. / wt. to 10% wt. / wt. of the total composition.

28. The method of claim 27, wherein the hair is eyelashes and / or eyebrows.

29. The method of claim 27, wherein the solubilizing compound is present in an amount of 1% wt. / wt. to 5% wt. / wt. of the total photoprotective topical composition.

30. The method of claim 27, wherein the solubilizing compound is present in an amount of 5% wt. / wt. to 10% wt. / wt. of the total photoprotective topical composition.

31. The method of claim 27, wherein the functional active is present in an amount of 1% wt. / wt. to 5% wt. / wt. of the total photoprotective topical composition.

32. The method of claim 27, wherein the functional active is present in an amount of 5% wt. / wt. to 10% wt. / wt. of the total photoprotective topical composition.

33. A photoprotective topical sunscreen composition for UV-light protection of human skin and / or hair comprising: a) 1% wt. / wt. to 10% wt. / wt. of at least one active sunscreen selected from bis-ethylhexyloxyphenol methoxyphenyl triazine, avobenzone and benzophenone-3; b) 1% wt. / wt. to 15% wt. / wt. of at least one solubilizing compound selected from 3-cyclohexyl toluate, 4-cyclohexyl toluate, or a combination thereof; and c) 1% wt. / wt. to 80% wt. / wt. of at least one topically administrable cosmetically or dermatologically acceptable carrier; wherein the solubilizing compound is in an amount effective to dissolve the active sunscreen agent.

34. The composition according to claim 33, wherein the composition further comprises at least one adjuvant or additive selected from a second polymer for improving water resistance, a UV active solubilizer, a solvent, an emulsifier, a preservative, a vitamin, an insect repellent, a wetting agent, a filler, a film former, a stabilizer, a buffer, a spreading agent, a pearlescent agent, an electrolyte, an acid, a base, a fatty substance, a softener, an emulsifier, an emollient, an antifoaming agent, a fragrance, an anionic surfactant, a cationic surfactant, a nonionic surfactant, a zwitterionic surfactant, an amphoteric surfactant, an active agent, a propellant, an acidifier or an alkalizer, an antioxidant, an alpha-hydroxy acid, a humectant, a colorant, a pharmaceutically or dermatologically or cosmetically acceptable excipient, and a combination thereof.

35. The composition of claim 33, wherein the composition further comprises at least one adjuvant or additive selected from a second polymer for improving water resistance, a UV active solubilizer, an oil, a wax, an emulsifier, a preservative, a vitamin, an insect repellent, a dye, a pigment, a wetting agent, a filler, a thickener, a film former, a buffer, a spreading agent, a pearlescent agent, an electrolyte, an acid, a base, an organic solvent, a softener, an opacifier, a silicone, a defoamer, a fragrance, an anionic surfactant, a cationic surfactant, a nonionic surfactant, a zwitterionic surfactant, an amphoteric surfactant, a propellant, an acidifier or an alkalizer, an antioxidant, an alpha-hydroxy acid, a moisturizer, an anti-inflammatory agent, a pharmaceutically or dermatologically or cosmetically acceptable excipient, and combinations thereof.

36. The composition of claim 35, wherein the thickener is selected from the group consisting of ionic thickeners, nonionic thickeners, hydrophilic thickeners, and lipophilic thickeners.

37. The composition of claim 33, wherein the solubilizing compound is present in an amount of 1% wt. / wt. to 5% wt. / wt. of the total photoprotective topical composition.

38. The composition of claim 33, wherein the solubilizing compound is present in an amount of 5% wt. / wt. to 10% wt. / wt. of the total photoprotective topical composition.

39. The composition of claim 33, wherein the active sunscreen is present in an amount of 1% wt. / wt. to 5% wt. / wt. of the total photoprotective topical composition.

40. The composition of claim 33, wherein the active sunscreen is present in an amount of 5% wt. / wt. to 10% wt. / wt. of the total photoprotective topical composition.

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