Glycidyl ester and associated method, composition, and product

Abstract

The invention provides a compound of the formula (i) wherein a is from 0 to 4, and b is from 1 to 4, provided that the sum of a and b is at least 2, and R is alkyl. The invention also provides methods for treating hair with an effective amount of a compound of Formula I, and compositions and products containing an effective amount of the compound.

Description

GLYCIDYL ESTER AND ASSOCIATED METHOD, COMPOSITION, AND PRODUCTCROSS-REFERENCE TO RELATED APPLICATIONS

[0001] This patent application claims the benefit of U.S. Provisional Application No. 63 / 572,775, filed April 1, 2024, which is incorporated herein by reference in its entirety.BACKGROUND OF THE INVENTION

[0002] Human hair is regularly exposed to conditions that are damaging to the structure and integrity of hair fibers. Notably, many widely used cosmetic processes that are intended to alter the hair such as, for example, bleaching / lightening, relaxing, permanent coloring, permanent waving, and keratin smoothing procedures, involve treating the hair with strong oxidants, alkaline reagents, reducing agents and / or aldehyde compounds, which may be damaging to hair fibers. Regular exposure to surfactants and detergents, such as those found in commercial shampoos, also may damage hair fibers. Human hair is also subjected to mechanical stresses such as, e.g., combing, brushing, and heat styling, which can damage hair fibers over time. Certain environmental conditions such as, e.g., exposure to sunlight and oxygen, also may be damaging to hair fibers.

[0003] Bleaching or lightening in a broader sense involves the lightening or decolorizing of hair. In technical terms, bleaching / lightening involves an oxidation process carried at an alkaline pH, e.g., pH 9.5-11. This process is generally employed either to lighten hair or to prepare hair for a coloring process when a lighter shade is preferred over the natural one. A common procedure involves lightening fibers in small bunches throughout the head to give a special affect. The result is hair with a higher tonal level than the natural one. Hair lightening is generally evaluated on a tonal scale from a level 1, which is black hair to a level 10, which is lightest blond hair.

[0004] Virtually all modern bleaching / lightening processes involve oxidation. This process gives lighter shades, resulting in white or blond hair depending on the application time and the strength of oxidant, typically a hydrogen peroxide solution or lotion, also known as a developer. Modern-day bleaching processes are very damaging to hair with respect to its loss of elasticity / strength, decrease in fiber moisture, fiber friction, loss of hair lipids, loss of hair shine, loss of hair proteins due to chipping away of cuticles, loss in fiber weight, and increase in fiber porosity. To change brown or medium brown hair to blonde, hair is typically bleached twice with powder lightener and 20 or 30 volume developer (6 to 9.0% hydrogenperoxide) to blonde shade. This bleaching process is considered to be a double process, and is extremely damaging to hair in terms of loss of elasticity and tensile strength, moisture loss, increased porosity, and split ends.

[0005] Hair straightening or relaxing is a permanent process in which hair is typically treated with a cream containing one or more alkali metal hydroxides, or guanidine hydroxide, for a period of 15 to 20 minutes. Hair straightening or relaxing typically converts about one- third of cystine bonds of hair to lanthionine bonds and consequently, the curly hair becomes permanently straight. This process typically results in the loss of 40-60% of tensile strength, significant moisture loss, and significant increase in the porosity of hair.

[0006] Permanent hair coloring is a reactive process in which, typically, a mixture of hydrogen peroxide and one or more oxidative dyes are applied to hair for a period of 30-45 minutes to alter the original color of the hair significantly. In such oxidative dyes, reducing agents such as sodium sulfite or sodium metabisulfite are also typically used to stabilize the dyeing creams from air oxidation. The mixture of oxidative dyes and hydrogen peroxide typically reduces hair fiber elasticity 5-15% depending upon the dye and the amount of oxidant, e.g., hydrogen peroxide, used in the process.

[0007] Permanent waving typically involves treating straight, wavy, or curly hair fibers with one or more reducing agents such as, e.g., ammonium thioglycolate or cysteamine hydrochloride, and then wrapping the treated hair around rollers / curlers to attain a desired hair shape. The fibers are then oxidized using, e.g., a 2.0 % hydrogen peroxide solution or 10.0% solution of sodium bromate. After the oxidation step, the rollers / curlers are removed, and a desired curly / wavy shape is attained. In this process, some of the cystine (disulfide) bonds in the hair fibers are reduced to cysteine, and then oxidized back to cystine. However, all of the reduced bonds may not convert back to cystine, thus causing hair damage, often resulting in a 20-25% loss of elasticity.

[0008] Keratin smoothing treatments often involve treating wavy / curly hair fibers with a solution of formaldehyde / methylene glycol, glyoxylic acid, or glyoxylol carbocysteine for 20-30 minutes, followed by blow drying and flat ironing using high temperatures such as, e.g., 230° C, and, e.g., 7 passes with a flat iron. When glyoxylic acid or glyoxylol carbocysteine is used, the hair is typically rinsed, blow dried, and flat ironed. The curly hair fibers become straight, shiny, and humidity resistant upon completion of the process. However, such keratin smoothing processes typically result in the loss of 15-20% of hair elasticity.

[0009] Combing, brushing, and blow-drying also may cause damage to hair, especially for wavy (Type 3) and curly (Type 4) hair. During these processes, the hair is often combed repeatedly, pulled by applying considerable force, and its surface rubbed constantly against the teeth of the comb or bristles of the brush. Additionally, heat is often applied, e.g., during blow-dying, which causes thermal damage to the hair and drives out inherent moisture from the hair.

[0010] Accordingly, there is a need for compounds, compositions, methods, and products for treating hair, e.g., to increase hair strength and / or elasticity, or to mitigate hair damage associated with exposure to conditions or treatments that are damaging to hair, particularly hair altering procedures such as, e.g., lightening / bleaching, relaxing, permanent coloring procedures, permanent waving, and keratin smoothing treatments. The present invention provides such compounds, compositions, methods, and products.BRIEF SUMMARY OF THE INVENTION

[0011] The invention provides a compound of the formula:wherein a is from 0 to 4, and b is from 1 to 4, provided that the sum of a and b is at least 2, and R is alkyl. In some embodiments, the compound of Formula I may include esters of fatty acids, for example, wherein R is a C11-C21 alkyl, wherein R is a C15-C21 alkyl, or wherein R is a C17-C21 alkyl. Embodiments of the invention also include, for example, a compound of Formula I, wherein a is from 1 to 4, b is from 1 to 4, and R is alkyl. Such embodiments may include, for example, a compound of Formula I, wherein a is from 1 to 4, b is from 1 to 4, and the compound of Formula I is a fatty acid ester, for example, a compound of Formula I, wherein a is from 1 to 4, b is from 1 to 4, and R is a C11-C21 alkyl; a compound of Formula I, wherein a is from 1 to 4, b is from 1 to 4, and R is a C15-C21 alkyl; or a compound of Formula I, wherein a is from 1 to 4, b is from 1 to 4, and R is a C17-C21 alkyl.

[0012] Embodiments of the invention additionally may include a compound of Formula I, wherein a is from 1 to 2, b is from 1 to 4, and R is alkyl. Such embodiments may include, for example, a compound of Formula I, wherein a is from 1 to 2, b is from 1 to 4, and the compound of Formula I is a fatty acid ester, e.g., a compound of Formula I, wherein a is from 1 to 2, b is from 1 to 4, and R is a C11-C21 alkyl; a compound of Formula I, wherein a is from 1 to 2, b is from 1 to 4, and R is a C15-C21 alkyl; or a compound of Formula I, wherein a is from 1 to 2, b is from 1 to 4, and R is a C17-C21 alkyl.

[0013] Embodiments of the invention further may include a compound of Formula la:Formula la wherein a is from 1 to 2, b is from 1 to 2, and R is alkyl as defined herein. Such embodiments may include, for example, a compound of Formula la, which is an ester of a fatty acid, e.g., a compound of Formula la, wherein R is a C11-C21 alkyl, a compound of Formula la, wherein R is a C15-C21 alkyl, or a compound of Formula la, wherein R is a C17- C21 alkyl.

[0014] Embodiments of the invention further may include a compound of Formula la, wherein R is a C17-C21 alkyl, e.g., a C17 alkyl, a C19 alkyl, a C21 alkyl, or the like. Examples of such embodiments include the compounds depicted below in Formulae lb and Ic:Formula lb wherein a is from 1 to 2, b is from 1 to 2, and the sum of a and b is 3, andwherein a is from 1 to 2, b is from Ito 2, and the sum of a and b is 3.

[0015] The invention also provides a method for treating hair, which includes contacting hair with an effective amount of a compound of Formula I. The method of the invention may be used for improving the quality of hair fibers, e.g., by increasing strength and / or elasticity of hair, and / or by increasing the resistance of hair to breakage. The method of the invention may be used for protecting hair from or repairing damage caused by a hair altering procedure, e.g., bleaching / lightening, straightening / relaxing, oxidative dying, permanent hair coloring, permanent waving, or keratin smoothing treatments, or damage caused by other factors, e.g., combing, brushing, blow-drying, or potentially damaging environmental conditions. The method may include protecting the hair from such damage prophylactically, e.g., before exposure to a potentially damaging procedure or condition, and / or therapeutically, e.g., during or after exposure to a potentially damaging procedure or condition. The method further may include reducing the likelihood, extent, degree, or severity of damage associated with exposure to such procedures or conditions, and / or repairing hair damaged from exposure to such procedures or conditions, e.g., by improving the structural integrity of, strengthening, or increasing the elasticity of hair fibers, thereby mending or repairing the hair fibers.

[0016] The method of the invention may be used, e.g., for mitigating / preventing or repairing hair damage caused by procedures that utilize oxidants or strongly alkaline reagents, e.g., hair lightening / bleaching agents, hair relaxing agents, oxidative hair dyeing or permanent coloring agents, permanent waiving agents, or smoothing agents. In some embodiments, the method includes mitigating / preventing or repairing hair damage associated with oxidative lightening or bleaching agents, relaxing agents, or oxidative dyeing or permanent coloring agents. The compound of Formula I may be applied to the hair before, concurrently / during, or following the application of such agents to the hair, and may be applied in any suitable form, e.g., in a substantially pure form or in the form of a suitable composition, e.g., solution, emulsion, cream, lotion, foam, gel, paste, solid, semi-solid, etc. If desired, the hair altering agent may be combined with an effective amount of a compound of Formula I (to form a composition) before application to the hair.

[0017] The invention additionally provides a composition comprising a carrier and an effective amount a compound of Formula I. The composition may include any suitable concentration of the compound of Formula I, e.g., from about 0.01 wt.% to about 25 wt.% of the compound of Formula I, and may further include, for example, one or more diluents, dispersants, emulsifiers, surfactants, and the like, in any suitable concentration, e.g., as described herein. The composition additionally may include one or more hair altering agents that may be damaging to hair fibers, for example, oxidative hair lightening / bleaching agents, hair relaxing agents, oxidative hair dyeing or permanent coloring agents, permanent waving agents, smoothing agents, and the like. The composition of the invention may exist in any suitable form, e.g., solution, emulsion, cream, lotion, foam, gel, paste, solid, semi-solid, and the like, and may be applied to the hair in any suitable manner, e.g., manually, with an applicator, by spraying, etc.

[0018] The composition of the invention may be formulated as an emulsion containing an effective amount of the compound of Formula I and a suitable vehicle, for example, an aqueous liquid vehicle such as, e.g., water. Emulsions of the invention, e.g., aqueous emulsions of the invention, may include one or more dispersants, diluents, emulsifiers, and / or surfactants to promote the formation of and / or to stabilize the emulsion, and may include any suitable concentration of a compound of Formula I, e.g., as described herein. Compositions of the invention also may be formulated as a micro-emulsions or nano-emulsions.

[0019] The composition of the invention may be combined with one or more hair altering agents, e.g., before the hair altering agent is applied to the hair and / or when the hair alteringagent is applied to the hair. For example, an effective amount of a compound of Formula I may be combined with one or more oxidative hair lightening / bleaching agents, one or more hair relaxing agents, or one or more oxidative hair dyeing or permanent coloring agents, to form the composition. Such compositions may be used in hair altering procedures, and may be prepared, e.g., by combining an effective amount of a compound of Formula I with the hair altering agent before application to the hair, or by combining such components when the agent is applied to the hair.

[0020] The invention further provides a product, which includes an effective amount of a compound of Formula I, and instructions for applying the compound to the hair. The product of the invention may include a compound of Formula I formulated in a composition, e.g., in combination with a carrier as described herein. The product may further include a hair care or hair altering agent, combined with or contained separately from a compound of Formula I, and instructions for applying the hair altering agent and compound of Formula I to the hair. The hair altering agent may include one or more hair altering agents that may be damaging to hair fibers, e.g., oxidative hair lightening agents, hair relaxing agents, and / or oxidative hair dyeing or permanent coloring agents. The instructions may include instructions for applying a compound of Formula I before, during, or after application of a hair altering agent to the hair.DETAILED DESCRIPTION OF THE INVENTION

[0021] The invention provides a compound of the formula:wherein a is from 0 to 4, and b is from 1 to 4, provided that the sum of a and b is at least 2, and R is alkyl. The compound of the invention may be described as an esterified polyglycerol wherein one or more of the secondary hydroxyls are functionalized with glycidyl (epoxy-substituted methyl) substituents. The term “alkyl” as used herein includesany suitable saturated or unsaturated, linear or branched alkyl substituent, for example, a Ci- C40 alkyl (i.e., a saturated or unsaturated, linear or branched alkyl substituent having 1-40 carbon atoms), C1-C39 alkyl, C1-C38 alkyl, C1-C37 alkyl, C1-C36 alkyl, C1-C35 alkyl, C1-C34 alkyl, C1-C33 alkyl, C1-C32 alkyl, C1-C31 alkyl, C1-C30 alkyl, C1-C29 alkyl, C1-C28 alkyl, Ci- C27 alkyl, C1-C26 alkyl, C1-C25 alkyl, C1-C24 alkyl, C1-C23 alkyl, C1-C22 alkyl, C1-C21 alkyl, C1-C20 alkyl, C1-C19 alkyl, C1-C18 alkyl, C1-C17 alkyl, C1-C16 alkyl, C1-C15 alkyl, C1-C14 alkyl, C1-C13 alkyl, C1-C12 alkyl, C1-C11 alkyl, C1-C10 alkyl, C1-C9 alkyl, Ci-C8alkyl, C1-C7 alkyl, C1-C6 alkyl, C1-C5 alkyl, C5-C40 alkyl, C5-C30 alkyl, C5-C25 alkyl, C5-C20 alkyl, C6-C4o alkyl, C6-C30 alkyl, C6-C25 alkyl, C6-C20 alkyl, C7-C40 alkyl, C7-C30 alkyl, C7-C25 alkyl, C7- C20 alkyl, C8-C40 alkyl, C8-C30 alkyl, C8-C25 alkyl, C8-C20 alkyl, C9-C40 alkyl, C9-C30 alkyl, C9-C25 alkyl, C9-C20 alkyl, C10-C40 alkyl, C10-C30 alkyl, C10-C25 alkyl, C10-C20 alkyl, C11-C40 alkyl, C11-C30 alkyl, C11-C25 alkyl, C11-C20 alkyl, C12-C40 alkyl, C12-C30 alkyl, C12-C25 alkyl, C12-C20 alkyl, C13-C40 alkyl, C13-C30 alkyl, C13-C25 alkyl, C13-C20 alkyl, C14-C40 alkyl, C14-C30 alkyl, C14-C25 alkyl, C14-C20 alkyl, C15-C40 alkyl, C15-C30 alkyl, C15-C25 alkyl, C15-C20 alkyl, and the like.

[0022] In some embodiments, the ester component of the compound of Formula I includes a fatty acid ester. Such embodiments may include, for example, a compound of Formula I, wherein R is a C11-C21 alkyl; a compound of Formula I, wherein R is a C15-C21 alkyl; or a compound of Formula I, wherein R is a C17-C21 alkyl. For example, the compound of Formula I may include esters of undecylic acid (undecanoic acid, wherein R is a C10 n- alkyl), lauric acid (dodecanoic acid, wherein R is a C11 / / -alkyl), tridecylic acid (tridecanoic acid, wherein R is a C12 / / -alkyl), myristic acid (tetradecanoic acid, wherein R is a C13 n- alkyl), pentadecylic acid (pentadecanoic acid, wherein R is a C14 n-alkyl), palmitic acid (hexadecanoic acid, wherein R is a C15 / / -alkyl), palmitoleic acid (wherein R is a C15 unsaturated alkyl), margaric acid (heptadecanoic acid, wherein R is a Ci6 / / -alkyl), isostearic acid (wherein R is a C17 branched alkyl), stearic acid (octadecanoic acid, wherein R is a C17 / / -alkyl), oleic acid (wherein R is a C17 unsaturated alkyl), linoleic acid (wherein R is a C17 unsaturated alkyl), a-linolenic acid (wherein R is a C17 unsaturated alkyl), y-linolenic acid (wherein R is a C17 unsaturated alkyl), stearidonic acid (wherein R is a C17 unsaturated alkyl), vaccenic acid (wherein R is a C17 unsaturated alkyl), nonadecylic acid (nonadecanoic acid, wherein R is a Cis / / -alkyl), arachidic acid (icosanoic acid, wherein R is a C19 / / -alkyl), eicosapentaenoic acid (wherein R is a C19 unsaturated alkyl), arachidonic acid (wherein R is a C19 unsaturated alkyl), gondoic acid (wherein R is a C19 unsaturated alkyl), heneicosylic acid(heneicosanoic acid, wherein R is a C20 w-alkyl), behenic acid (docosanoic acid, wherein R is a C21 w-alkyl), docosatetraenoicacid (wherein R is a C21 unsaturated alkyl), cervonic acid (wherein R is a C21 unsaturated alkyl), erucic acid (wherein R is a C21 unsaturated alkyl), and the like.

[0023] In some embodiments, the invention provides is a compound of Formula I, wherein a is from 1 to 4, b is from 1 to 4, and R is alkyl. Such embodiments may include a compound of Formula I, wherein a is from 1 to 4, b is from 1 to 4, and the compound of Formula I is a fatty acid ester, for example, a compound of Formula I, wherein a is from 1 to 4, b is from 1 to 4, and R is a C11-C21 alkyl; a compound of Formula I, wherein a is from 1 to 4, b is from 1 to 4, and R is a C15-C21 alkyl; or a compound of Formula I, wherein a is from 1 to 4, b is from 1 to 4, and R is a C17-C21 alkyl. Such embodiments also may include, for example, a compound of Formula I, wherein a is from 1 to 4, b is from 1 to 4, and R is a C11- C21 saturated alkyl; a compound of Formula I, wherein a is from 1 to 4, b is from 1 to 4, and R is a C15-C21 saturated alkyl; or a compound of Formula I, wherein a is from 1 to 4, b is from 1 to 4, and R is a C17-C21 saturated alkyl.

[0024] In some embodiments, the invention provides a compound of Formula I, wherein a is from 1 to 2, b is from 1 to 4, and R is alkyl. Such embodiments may include a compound of Formula I, wherein a is from 1 to 2, b is from 1 to 4, and the compound of Formula I is a fatty acid ester, for example, a compound of Formula I, wherein a is from 1 to 2, b is from 1 to 4, and R is a C11-C21 alkyl; a compound of Formula I, wherein a is from 1 to 2, b is from 1 to 4, and R is a C15-C21 alkyl; or a compound of Formula I, wherein a is from 1 to 2, b is from 1 to 4, and R is a C17-C21 alkyl. Such embodiments also may include, for example, a compound of Formula I, wherein a is from 1 to 2, b is from 1 to 4, and R is a C11-C21 saturated alkyl; a compound of Formula I, wherein a is from 1 to 2, b is from 1 to 4, and R is a C15-C21 saturated alkyl; or a compound of Formula I, wherein a is from 1 to 2, b is from 1 to 4, and R is a C17-C21 saturated alkyl.

[0025] In some embodiments, the invention provides a compound of Formula la:wherein a is from 1 to 2, b is from 1 to 2, and R is alkyl as defined herein. Such embodiments may include, for example, a compound of Formula la, which is a fatty acid ester, for example, a compound of Formula la, wherein R is a C11-C21 alkyl, e.g., a C11-C21 saturated alkyl; a compound of Formula la, wherein R is a C15-C21 alkyl, e.g., a C15-C21 saturated alkyl; or a compound of Formula la, wherein R is a C17-C21 alkyl, e.g., a C17-C21 saturated alkyl.

[0026] In some embodiments, the invention provides a compound of Formula la, wherein R is a C17-C21 alkyl, e.g., a C17 alkyl, a C19 alkyl, a C21 alkyl, or the like. Examples of such embodiments may include the compounds depicted below in Formula lb and Formula Ic:wherein a is from 1 to 2, b is from 1 to 2, and the sum of a and b is 3, andFormula Ic wherein a is from 1 to 2, b is from Ito 2, and the sum of a and b is 3.

[0027] The compound of the invention was surprisingly and unexpectedly found to be highly effective in treating and particularly in mending hair, e.g., by increasing hair strength / elasticity and / or by increasing the resistance of hair to breakage, e.g., from mechanical stress. The compound of the invention was even found to be effective in treating “virgin” hair, with no previous exposure to a hair altering chemical process, as well as hair that has been treated with one or more hair altering chemical processes. The compound of the invention was, thus, surprisingly and unexpectedly found to be highly effective in treating hair generally, e.g., by increasing natural fiber strength / elasticity and / or resistance to breakage generally, and / or, e.g., by mending hair and / or protecting hair from damage associated with hair altering chemical procedures such as, e.g., bleaching / lightening, straightening / relaxing, permanent hair coloring, permanent waving, and keratin smoothing treatments, or other factors, e.g., combing, brushing, blow-drying, and exposure to the sun, heat, elements, etc., thereby improving, preserving, and / or restoring desirable hair fiber properties. Without wishing to be bound by any particular theory, it is believed that the compound of the invention, possibly via the epoxide substituents, may react with broken disulfide (-S-S-) bonds, amino groups, or carboxyl (-COOH) groups of the polypeptide side chains of hair fibers in such a way that strengthens hair fibers in terms of increasing their structural integrity, elasticity / strength, and / or resistance to breakage.

[0028] The compound of the invention may be prepared by reacting the desired esterified polyglycerol with l,3-dichloro-2-propanol or epichlorohydrin in an amount sufficient to produce the compound of Formula I. Thus, the compound of Formula I generally may be prepared, for example, by reacting a suitably esterified polyglycerol with 1,3- dichloropropanol as depicted below in Scheme 1 :Scheme 1 wherein a, b, and R are as defined herein. Similarly, by way of example, the compound of Formula lb may be prepared by reacting polyglycerol-3 diisostearate (CAS No. 66082-42-6) with 1,3-dichloropropanol as depicted below in Scheme 2:Polyglyceryl-3 diisostearateFormula lbScheme 2 wherein a is from 1 to 2, and b is from 1-2, provided that the sum of a and b is 3.

[0029] The present invention also provides a method for treating hair by contacting the hair with an effective amount of a compound of Formula I to treat the hair. As used herein, “treating” refers to improving the quality of hair fibers in any measurable way including, e.g., increasing the strength of hair, e.g., increasing the elasticity of hair, increasing the tensile strength of hair, increasing the resistance of hair to breakage, reducing split ends, making hair fibers less brittle, increasing moisture retention in hair fibers, reducing the porosity of hair fibers, and the like, and combinations thereof. Treating may include, for example, increasing the resistance of hair to damage associated with one or more hair altering procedures that may be damaging to the hair, e.g., bleaching / lightening, straightening / relaxing, permanent hair coloring, permanent waving, keratin smoothing treatments, and the like, as well as increasing the resistance of hair to damage associated with other factors, e.g., combing, brushing, blow-drying, and exposure to the sun, heat, elements, etc. Treating also may include, e.g., protecting the hair from such damage prophylactically, e.g., by applying an effective amount of the compound of Formula I before exposure of the hair to a procedure orcondition that may damage hair, and therapeutically, e.g., by applying an effective amount of the compound of Formula I during or after exposure of the hair to a procedure or condition that may damage hair. Treating further may include, e.g., reducing the likelihood, extent, degree, or severity of damage associated with exposure to such procedures or conditions, and / or repairing hair damaged from exposure to such procedures or conditions, e.g., by improving the structural integrity of hair fibers, strengthening hair fibers, or increasing the elasticity of hair fibers, thereby repairing or mending hair damage caused by such procedures or conditions.

[0030] As used herein, “effective amount” includes any amount of the compound of Formula I that, when applied, is sufficient for treating the hair as described herein, including, e.g., improving the quality of hair fibers in any measurable way, e.g., increasing the strength of hair, e.g., increasing the elasticity of hair, increasing the resistance of hair to breakage, and the like, and combinations thereof. An effective amount also includes an amount that is effective for mitigating hair damage associated with exposure to procedures or conditions that may damaging to hair fibers, e.g., including procedures or conditions that may cause disulfide bond breakage. In some embodiments, the effective amount may include an amount effective for reducing the likelihood, extent, degree, or severity of damage associated with exposure to such procedures conditions, and / or an amount effective for repairing damaged hair, e.g., improving the structural integrity of, strengthening, improving the elasticity of, and / or mending hair damaged by exposure to such procedures or conditions. The method of the invention may be used, e.g., for treating hair damage caused by a hair altering process that is capable of damaging hair fibers. Examples of such hair altering processes may include, e.g., procedures that utilize oxidants and / or strongly alkaline reagents that may be damaging to hair, e.g., hair lightening / bleaching procedures, hair relaxing procedures, hair dyeing procedures, permanent coloring, permanent waiving, smoothing, and the like.

[0031] The method of the invention includes treating hair with an effective amount of a compound of Formula I before the hair is subjected to one or more hair altering procedures or conditions that may be damaging to the hair, e.g., as described herein (e.g., as a pretreatment), or both before and after such procedures or exposure to such conditions. The method of the invention also includes treating hair with an effective amount of a compound of Formula I during and / or after the hair is subjected to one or more hair altering procedures that may damage the hair, e.g., as described herein. The method of the invention further includes treating hair generally with an effective amount of a compound of Formula I,including “virgin” hair which has not been or will not be subjected to a potentially damaging hair altering procedure or otherwise exposed to potentially damaging environmental conditions.

[0032] The method of the invention thus may include preventing and / or repairing / mending hair damage associated with an oxidative hair lightening / bleaching agent. For example, an effective amount of a compound of Formula I may be applied to the hair before, concurrently, or following application of the oxidative hair lightening / bleaching agent to the hair, including both before and after the procedure. If desired, the compound of Formula I and oxidative hair lightening / bleaching agent may be combined together to form a hair lightening / bleaching composition containing an effective amount of the compound of Formula I, before application to the hair.

[0033] The method of the invention also may include preventing and / or repairing / mending hair damage associated with a hair relaxing agent. For example, an effective amount of a compound of Formula I may be applied to the hair before, concurrently, or following application of the hair relaxing agent to the hair, including both before and after the procedure. If desired, the compound of Formula I and hair relaxing agent may be combined together to form a hair relaxing composition containing an effective amount of the compound of Formula I, before application to the hair.

[0034] The method of the invention further may include preventing and / or repairing hair damage associated with an oxidative hair dyeing or permanent coloring agent. For example, an effective amount of the compound of Formula I may be applied to the hair before, concurrently, or following application of the oxidative hair dyeing or permanent coloring agent to the hair, including before and after the procedure. If desired, the compound of Formula I and oxidative hair dyeing or permanent coloring agent may be combined together, to form an oxidative hair dyeing or permanent coloring composition containing an effective amount of the compound of Formula I, before application to the hair.

[0035] The compound of formula I may be applied to the hair in any suitable form, e.g., in a substantially pure form (if the properties of the compound allow for such application) or in the form of a suitable composition, e.g., a solution, an emulsion, a cream, a lotion, a foam, a gel, a paste, a solid composition (e.g., powder), a semi-solid composition, and the like. The compound or composition of the invention may be applied to hair in any suitable manner, e.g., manually, by way of an applicator, by spraying, etc.

[0036] The present invention additionally provides a composition comprising a carrier and an effective amount of at least one compound of Formula I as described herein. The composition of the invention may include, e.g., as part of or in combination with the carrier, any suitable component(s) used in hair, cosmetic, and / or pharmaceutical product formulations, including hair care or hair altering products, e.g., one or more dispersants, emulsifiers, surfactants, oxidative hair lightening or bleaching agents, hair relaxing agents, oxidative hair dyeing or permanent hair coloring agents, permanent waving agents, smoothing agents, conditioners, shampoos, moisturizers, excipients, diluents, vehicles, additives, fillers, texturing agents, pigments, dyes, coloring agents, fragrances, and the like, and combinations thereof. The carrier thus may include one or more suitable diluents, excipients, vehicles, additives, fillers, texturing agents, pigments, dyes, coloring agents, and the like, including one or more known excipients, diluents, vehicles, additives, fillers, texturing agents, pigments, dyes, coloring agents, etc., which are used in formulating hair, cosmetic, and / or pharmaceutical products, to achieve a desired form or other desired properties using formulation methods that are known in the art.

[0037] In some embodiments, the composition of the invention may include one or more hair altering agents that may be damaging to hair fibers. Such hair altering agents may include, for example, oxidative hair lightening / bleaching agents, hair relaxing agents, oxidative hair dyeing or permanent coloring agents, permanent waving agents, smoothing agents, and the like, as described herein. In some embodiments, the carrier used in the composition of the invention may contain a fluid, e.g., a liquid vehicle. In some embodiments, the liquid vehicle may include an aqueous liquid vehicle such as, for example, water, water containing one or more aqueous co-solvents, water containing one or more aqueous solutes, or the like. The solubility or affinity of the compound of Formula I with respect to water may potentially impact how one of ordinary skill in the art may approach formulating the compound in an aqueous liquid vehicle. The compound of Formula I need not be water soluble in order to be formulated in an aqueous vehicle, and need not be water soluble or otherwise in the form of a solution in order to be effective for purposes of the invention. As such, the compound of Formula I may be sparingly soluble in water or water insoluble and still be effective for purposes of the present invention.

[0038] The composition of the invention may include the compound of Formula I in any suitable concentration. For example, the composition of the invention may include the compound of Formula I at a concentration of, e.g., from about 0.01 wt.% to about 25 wt.%,from about 0.01 wt.% to about 20 wt.%, from about 0.01 wt.% to about 15 wt.%, from about 0.01 wt.% to about 10 wt.%, from about 0.01 wt.% to about 5 wt.%, from about 0.01 wt.% to about 4 wt.%, from about 0.01 wt.% to about 3 wt.%, from about 0.01 wt.% to about 2 wt.%, from about 0.01 wt.% to about 1 wt.%, from about 0.05 wt.% to about 25 wt.%, from about 0.05 wt.% to about 20 wt.%, from about 0.05 wt.% to about 15 wt.%, from about 0.05 wt.% to about 10 wt.%, from about 0.05 wt.% to about 5 wt.%, from about 0.05 wt.% to about 4 wt.%, from about 0.05 wt.% to about 3 wt.%, from about 0.05 wt.% to about 2 wt.%, from about 0.05 wt.% to about 1 wt.%, from about 0.1 wt.% to about 25 wt.%, from about 0.1 wt.% to about 20 wt.%, from about 0.1 wt.% to about 15 wt.%, from about 0.1 wt.% to about 10 wt.%, from about 0.1 wt.% to about 5 wt.%, from about 0.1 wt.% to about 4 wt.%, from about 0.1 wt.% to about 3 wt.%, from about 0.1 wt.% to about 2 wt.%, and from about 0.1 wt.% to about 1 wt.%. In some embodiments, the composition of the invention includes from about 0.1 wt.% to about 2 wt.%, e.g., about 0.2 wt.%, about 0.3 wt.%, about 0.4 wt.%, about 0.5 wt.%, about 0.6 wt.%, about 0.7 wt.%, about 0.8 wt.%, about 0.9 wt.%, about 1 wt.%, about 1.1 wt.%, about 1.2 wt.%, about 1.3 wt.%, about 1.4 wt.%, about 1.5 wt.%, about 1.6 wt.%, about 1.7 wt.%, about 1.8 wt.%, or about 1.9 wt.%, of the compound of Formula I.

[0039] The composition of the invention also may include, for example, one or more dispersants, emulsifiers, and / or surfactants such as, for example, sulfates of fatty alcohols, e.g., sodium lauryl sulfate, ammonium lauryl sulfate, and the like, fatty acid esters, e.g., sodium lauroyl lactylate, sodium lauroyl glutamate, and the like, polyols, e.g., propylene glycol, glycerin, and the like, polyols, e.g., polypropylene glycols, polyethylene glycols, and the like, emulsifying waxes, nonionic surfactants, e.g., Polychol 15, and the like, and combinations thereof. The composition of the invention may include one or more dispersants, emulsifiers, and / or surfactants in any suitable concentration. For example, the composition of the invention may include from about 0.01 wt.% to about 15 wt.%, e.g., from about 0.01 wt.% to about 10 wt.%, from about 0.01 wt.% to about 9 wt.%, from about 0.01 wt.% to about 8 wt.%, from about 0.01 wt.% to about 7 wt.%, from about 0.01 wt.% to about 6 wt.%, from about 0.01 wt.% to about 5 wt.%, from about 0.01 wt.% to about 4 wt.%, from about 0.01 wt.% to about 3 wt.%, from about 0.01 wt.% to about 2 wt.%, from about 0.01 wt.% to about 1 wt.%, from about 0.05 wt.% to about 15 wt.%, from about 0.05 wt.% to about 10 wt.%, from about 0.05 wt.% to about 9 wt.%, from about 0.05 wt.% to about 8 wt.%, from about 0.05 wt.% to about 7 wt.%, from about 0.05 wt.% to about 6 wt.%, from about 0.05 wt.% to about 5 wt.%, from about 0.05 wt.% to about 4 wt.%, from about 0.05wt.% to about 3 wt.%, from about 0.05 wt.% to about 2 wt.%, from about 0.05 wt.% to about 1 wt.%, from about 0.1 wt.% to about 15 wt.%, from about 0.1 wt.% to about 10 wt.%, from about 0.1 wt.% to about 9 wt.%, from about 0.1 wt.% to about 8 wt.%, from about 0.1 wt.% to about 7 wt.%, from about 0.1 wt.% to about 6 wt.%, from about 0.1 wt.% to about 5 wt.%, from about 0.1 wt.% to about 4 wt.%, from about 0.1 wt.% to about 3 wt.%, from about 0.1 wt.% to about 2 wt.%, from about 0.1 wt.% to about 1 wt.%, from about 0.5 wt.% to about 15 wt.%, from about 0.5 wt.% to about 10 wt.%, from about 0.5 wt.% to about 9 wt.%, from about 0.5 wt.% to about 8 wt.%, from about 0.5 wt.% to about 7 wt.%, from about 0.5 wt.% to about 6 wt.%, from about 0.5 wt.% to about 5 wt.%, from about 0.5 wt.% to about 4 wt.%, from about 0.5 wt.% to about 3 wt.%, from about 0.5 wt.% to about 2 wt.%, or from about 0.5 wt.% to about 1 wt.% of one or more dispersants, emulsifiers, and / or surfactants.

[0040] The composition of the invention may be applied to the hair in any suitable form, e.g., a solution, an emulsion, a cream, a lotion, a foam, a gel, a paste, a solid composition (e.g., powder), a semi-solid composition, or the like. The composition of the invention may be applied to the hair in any suitable manner, e.g., manually, with an applicator, by spraying, etc.

[0041] In some embodiments, the composition of the invention may be formulated as an emulsion containing an effective amount of the compound of Formula I and a suitable vehicle, for example, an aqueous liquid vehicle, e.g., water. Emulsions of the invention, e.g., aqueous emulsions of the invention, may include one or more dispersants, diluents, emulsifiers, and / or surfactants to promote the formation of and / or to stabilize the emulsion. Suitable dispersants, emulsifiers, and / or surfactants may include, for example, sulfates of fatty alcohols, e.g., sodium lauryl sulfate, ammonium lauryl sulfate, and the like, fatty acid esters, e.g., sodium lauroyl lactylate, sodium lauroyl glutamate, and the like, emulsifying phosphate esters, e.g., dicetyl phosphate and ceteth-10 phosphate, and the like, polyols, e.g., propylene glycol, glycerin, and the like, polyols, e.g., polypropylene glycols, polyethylene glycols, and the like, emulsifying waxes, e.g., nonionic surfactants, e.g., polyoxyalkylene sorbitan esters, e.g., polysorbates, e.g., polysorbate 20, polysorbate 40, polysorbate 60, Polychol 15, and the like, and combinations thereof. The emulsion of the invention may include any suitable concentration of a compound of Formula I, as described herein. The emulsion of the invention may be formulated as a micro-emulsion or nano-emulsion, e.g., as described in WO 2017 / 124061 (Syed et al.).

[0042] The composition of the invention may be formulated with one or more hair altering agents, e.g., before the hair altering agent is applied to the hair and / or when the hair altering agent is applied to the hair. For example, the composition of the invention may include an effective amount of a compound of Formula I and one or more oxidative hair lightening / bleaching agents. Such a composition may be used in hair lightening / bleaching procedures, and may be prepared, e.g., by combining an effective amount of a compound of Formula I with an oxidative hair lightening / bleaching agent before application to the hair, or by combining such components when the agent is applied to the hair. Suitable hair lightening / bleaching agents for inclusion in the composition may include, for example, mixtures prepared by combining a persulfate and a peroxide. Suitable persulfates may include, for example, potassium persulfate, ammonium persulfate, and combinations thereof. Suitable peroxides may include, for example, hydrogen peroxide.

[0043] The composition of the invention also may include an effective amount of a compound of Formula I and one or more hair relaxing agents. Such a composition may be used in hair relaxing procedures, and may be prepared, e.g., by combining an effective amount of a compound of Formula I with a hair relaxing agent before application to the hair, or by combining such components when the agent is applied to the hair. Suitable hair relaxing agents for inclusion in the composition may include, for example, mixtures prepared by combining a metal hydroxide and an alkaline salt of guanidine. Metal hydroxides suitable for relaxer systems may include, for example, calcium hydroxide. Alkaline salts of guanidine suitable for relaxer systems may include, for example, guanidine carbonate.

[0044] The composition of the invention further may include an effective amount of a compound of Formula I and one or more oxidative hair dyeing or permanent coloring agents. Such a composition may be used in oxidative dying or permanent coloring procedures, and may be prepared, e.g., by combining an effective amount of a compound of Formula I with an oxidative hair dyeing or permanent coloring agent before application to the hair, or by combining such components when the agent is applied to the hair. Suitable oxidative hair dyeing or permanent coloring agents for inclusion in the composition may include, for example, mixtures prepared by combining a permanent hair dyeing agent with a peroxide. In some embodiments, the composition may include two or more permanent hair dyes. Peroxides suitable for use in oxidative hair dyeing or permanent coloring systems may include, e.g., hydrogen peroxide.

[0045] The composition of the invention may include any suitable concentration of a compound of Formula I, e.g., as described herein. The composition of the invention also may include any suitable concentration of any other component(s) used in the composition, including, e.g., any diluents, dispersants, emulsifiers, surfactants, any hair care products or hair altering agents, e.g., oxidative hair lightening or bleaching agents, hair relaxing agents, oxidative hair dyeing or permanent hair coloring agents, permanent waving agents, smoothing agents, conditioners, shampoos, moisturizers, and the like, and any other components, e.g., excipients, diluents, vehicles, additives, fillers, texturing agents, pigments, dyes, coloring agents, fragrances, and the like, e.g., as described herein.

[0046] The composition of the invention may be applied to the hair in any suitable form, e.g., a solution, an emulsion, a cream, a lotion, a foam, a gel, a paste, a solid composition (e.g., powder), a semi-solid composition, and the like. The composition of the invention may be applied to the hair in any suitable manner, e.g., manually, with an applicator, by spraying, etc.

[0047] The invention further provides a product, which includes an effective amount of at least one compound of Formula I as described herein, and instructions for applying the compound of Formula I to the hair. If desired, the compound of Formula I may be formulated as a composition, e.g., in combination with a carrier, as described herein. The product of the invention may further include a hair care or hair altering agent, combined with or contained separately from a compound of Formula I, and instructions for applying the hair altering agent and a compound of Formula I to the hair. The hair altering agent may include one or more hair altering agents capable of damaging hair fibers. Such hair altering agents may include, for example, oxidative hair lightening agents, hair relaxing agents, and / or oxidative hair dyeing or permanent coloring agents, as described herein. When the product of the invention includes a hair altering agent, the instructions, e.g., for applying a compound of Formula I, for applying the hair altering agent, or both, may include instructions for applying the compound of Formula I before, concurrently, or following application of the hair altering agent to the hair.

[0048] For example, the product of the invention may include one or more hair altering agents and instructions for combining the hair altering agent with an effective amount of a compound of Formula I before application to the hair, or for applying / combining a compound of Formula I when a hair altering agent is applied to the hair. The product of the invention also may include, e.g., a composition containing an effective amount of a compound ofFormula I and one or more hair altering agents, and instructions for applying the composition to the hair. The product of the invention further may include, e.g., a composition containing an effective amount of a compound of Formula I, and instructions for applying the composition to the hair before or after application of the hair altering agent to the hair, including before and after application of the hair altering agent.EXAMPLES

[0049] The following examples further illustrate the invention but should not be construed as in any way limiting its scope.Analytical Methods

[0050] Intermittent Stress Relaxation (ISR) Test

[0051] The ISR test probes the hair with a short pulse of force, which is followed by a longer time of relaxation during which the hair is not subjected to any tension. The force is programmed in such a manner that the instrument extends the hair for 0.10 minute to 0.5% strain and measures the maximum stress generated inside it. Subsequently, the force is dropped to zero and the hair is allowed to relax for the next 0.90 minute. The cycle is repeated ten times. Since the measurement is done for the same section of the same hair fiber twice, before and after the chemical treatment, the changes in stress reflect damage to the elastic strength of hair inflicted by the treatment.

[0052] The ISR test may be performed using a dynamic mechanical analyzer (DMA). The relative strength of chemically treated hair is measured a posteriori following a finalization of the chemical treatment process. The ISR test is conducted twice on the same hair fiber immersed in water; first before the chemical treatment, and subsequently after the treatment. The stress measured at 0.5% strain is compared, and its drop after the chemical treatment is used as a measure of fiber strength after chemical treatment.

[0053] ISR tests were performed using a Discovery DMA (Dynamic Mechanical Analyzer) Model 850 to assess the internal chemical damage of hair via loss in elastic strength of wet hair fibers. The instrument includes a drive motor that provides the static and dynamic or oscillatory force. The drive motor transmits force directly to a rectangular airbearing slide that is also connected to the drive shaft and sample clamp. The compressed air supplied to the air bearings allows the slide to float. The distance or vertical movement of the air-bearing slide during testing is translated to the force required for that specific run. Anoptical encoder is used to measure the displacement during testing based on diffraction patterns of light through gratings (one stationary and one moveable). A furnace provides temperature control required during testing.

[0054] In this test, each single fiber (gauge length = 14.82 mm) is mounted to the submersible fiber specimen clamp containing water. The fiber is stretched to a constant strain or 0.5% of its length (from 14.82 to 14.894 mm length) for 0.1 minute and allowed to recover for 0.90 minute. This process of imposing the strain and allowing it to recover is repeated for a total of 10 cycles. The force is expressed in grams while the area was expressed in denier (a textile terminology defined as weight in grams of 9,000 meters of yams or fibers). The diameter of the hair specimen is measured using the LaserMike® scanning micrometer. The average diameter is recorded as (x + y) / 2, where x is the major axis and y is the minor axis. The amount of stress (g / denier) for each cycle is measured and recorded. An intermittent stress curve may be generated using this device. The ratio of after to before treatment force is calculated and used to assess the internal condition of hair fibers. An index of 1.0 indicates that there was no chemical damage done to the hair. A value less than 1.0 indicates that fibers were internally damaged by the treatment. A value of higher than 1 indicates that fibers were strengthened.

[0055] An advantage of this method over conventional tensile strength tests (fiber stretched to the breakpoint) is that the ISR test is performed within the Hookean region (<2% strain), i.e., a fiber is stretched to a constant elongation of 0.5% strain and same fiber is employed for before and after test. At this specified elongation, it is demonstrated that a chemically untreated hair could be repeatedly stretched without undergoing permanent physical deformation. Measuring the elastic strength of wet hair in the range of 0.5 to about 1% strain is believed to simulate the range of strain applied during a conventional grooming process, such as combing, brushing, styling, and setting of the hair.

[0056] Repeated Brushing Test

[0057] To mimic real life hair fatigue from combing and brushing and hair breakage, a combing / brushing device was constructed to brush hair tresses repeatedly for up to 10,000 times at intervals of 1000 strokes, and the fibers broken upon brushing are counted to decipher the difference / extent of brushing damage caused by repeated brushing of hair. A comparison is made between various treatments with control and treatments with compositions formulated according to the invention.

[0058] The combing / brushing machine includes an arm, which is capable of revolving in circular motion. This arm is equipped with a brush or comb of the choice and in its path a stationary hair tress is attached to another arm. The tresses are combed or brushed at a specific speed with the help of a motorized arm to which a selected comb or brush is attached.

[0059] The device used herein includes a brush, a digital counter (counts the number of brushing strokes), a motor with an attached cylindrical bar from which 2 circular metal plates are mounted to hold the brush / comb, a tress holder and black / white plastic sheet to collect broken fibers. The brushing speed is set at the rate of 52 strokes per minute, which represents the median brushing strokes for twenty (20) women of varying ages and ethnicity based on information acquired in our test salon. A similar to the device is described in WO 2017 / 124061 (Syed, et al.).

[0060] All hair tresses, untreated and treated, are brushed multiple times for a total of 10,000 brushing strokes. Twelve (12) hair tresses are used for each group. Broken hair fibers are counted after every 1000 strokes until the completion of 10,000 brushing strokes. The number of broken fibers are collected and recorded. This test is performed in a humidity controlled room, where the relative humidity is set to be 60% at room temperature.EXAMPLE 1

[0061] This example demonstrates a method for preparing an exemplary compound of the invention (Formula lb). Polyglycerol-3 diisostearate is prepared by heating a mixture of polyglycerol-3 (253 g) and isostearic acid (743 g, approximate molar ratio of 2.5 relative to polyglycerol-3) at a temperature of from about 50 °C to about 160 °C over a period about 45 minutes, then continuing to heat the mixture for an additional 7 hours at about 160 °C while distilling off water, to produce a clear yellow liquid, which is then stripped under vacuum for approximately 2 hours, to produce polyglycerol-3 diisostearate as a clear yellow liquid. Polyglycerol-3 diisostearate (800 g, CAS Number 66082-42-6) is combined with 1,3- dichloro-2-propanol (200 g, Colonial Chemical, CAS Number 96-23-1) in a reaction flask equipped with a stir bar and a reflux condenser, and the mixture is heated under reflux for about 6 hours at a temperature of about 100 °C. The resulting product is then stripped under vacuum, allowed to cool to room temperature, and filtered to produce the compound of Formula lb.EXAMPLE 2

[0062] This example demonstrates a method for preparing an exemplary compound of the invention. A mixed ester of polyglycerol-3 is prepared by combining polyglycerol-3 (253 g), stearic acid (360 g, approximate molar ratio of 1.2 relative to polyglycerol-3), and isostearic acid (405 g, approximate molar ratio of 1.3 relative to polyglycerol-3), and heating the mixture at a temperature of from about 60 °C to about 160 °C over a period about 15 minutes. Heating is then continued for an additional 7.5 hours at about 160 °C while distilling off water, and the resulting product is stripped under vacuum to produce a di-stearate / isostearate mixed ester of polyglycerol-3. The mixed ester of polyglycerol-3 is reacted with 1,3- dichloro-2-propanol (Colonial Chemical, CAS Number 96-23-1) as described in Example 1 to produce a compound of the formula:wherein a is from 1-2, b is from 1-2, the sum of a and b is 3, and R' comprises a mixture of (CH2)ieCH3 and (CH2)i4C(CH3)2 alkyl substituents.EXAMPLE 3

[0063] This example demonstrates exemplary emulsions containing a compound of the invention. An emulsion containing 15 wt.% of the compound of Formula lb was prepared using the components describe below in Table 3.1.Table 3,1 (Emulsion 1)

[0064] Emulsion 1 (Table 3.1) was further diluted with water to produce Emulsions 2-4, having reduced concentrations of the compound of Formula lb relative to Emulsion 1. The components of the diluted emulsions are shown below in Table 3.2.Table 3.2 (Emulsions 2-4)

[0065] Emulsion 2 contains approximately 0.60 wt.% of the compound of Formula lb, Emulsion 3 contains approximately 1.00 wt.% of the compound of Formula lb, and Emulsion 4 contains approximately 0.30 wt.% of the compound of Formula lb.EXAMPLE 4

[0066] This example demonstrates exemplary methods for treating hair in accordance with the invention. Emulsions containing the compound of Formula lb were applied to virgin untreated hair, and the elasticities were compared between the untreated fibers and the fibers treated with emulsions of the invention, as follows:1. Wash the hair (Type 1 Hair, IM Hair, Italy) with non-conditioning shampoo2. Pre-test the hair fibers on the DMA using the intermittent stress relaxation test3. Embed the pre-tested hair fibers on a 4g hair tress.4. Apply 0.5 g of Emulsion 2, Emulsion 3, or Emulsion 4.5. Test the stress applied to fibers at 0.50% strain, again after 24 hours, at 100% humidity.

[0067] The strength of untreated fibers and fibers treated with Emulsion 2 are shown below in Table 4.1 (sample size: 27 fibers).Table 4.1

[0068] These results show that the strength of the untreated fibers on average increased 28% after treatment with Emulsion 2 (containing about 0.60 wt.% of a compound of the invention). The means of untreated fibers and treated fibers with Emulsion 2 were compared using paired T-Test and the results showed that the p value is < 0.001, confirming that thefibers treated with a compound of the invention were significantly stronger than untreated fibers (at p < 0.05).

[0069] The strength of untreated fibers and fibers treated with Emulsion 3 are summarized below in Table 4.2 (sample size: 27 fibers).Table 4.2

[0070] These results show that the strength of the untreated fibers on average increased 18% after treatment with Emulsion 3. The fibers treated with Emulsion 3 (containing 1.0 wt.% of a compound of the invention) were significantly stronger than the untreated fibers.

[0071] The strength of untreated fibers and fibers treated with Emulsion 4 are summarized below in Table 4.3 (sample size: 27 fibers; outliers excluded).Table 4.3

[0072] These results show that the strength of the untreated fibers on average increased 25% after treatment with Emulsion 4. The fibers treated with Emulsion 4 (containing 0.30 wt.% of a compound of the invention) were significantly stronger than the untreated fibers.EXAMPLE 5

[0073] This example demonstrates exemplary methods and compositions for treating hair in accordance with the invention. Hair strength following a conventional lightening procedure (control) was compared with hair strength following the lightening procedure in which the lightener composition included a compound of the invention.

[0074] The formulations of the compositions used in the study are described below in Tables 5.1-5.3, as follows:Table 5.1Conventional Powder Lightener (Control)Table 5.2Conventional Hydrogen Peroxide Developer 40 VolumeTable 5.3Conventional Non-conditioning Shampoo

[0075] A control group of hair fibers was treated with conventional powder lightener as described in Table 5.1 and conventional 40-volume developer as shown in Table 5.2 (sample size: 20 fibers). The mixing ratio of the hydrogen peroxide developer (40-volume) and the powder lightener was 2: 1. The application procedure was as follows:1. Pre-test the untreated hair specimens on DMA using the intermittent stress relaxation test, at 100% humidity.2. Embed the pre-tested hair fibers (Caucasian, IMHAIR) on a 4 g of hair tress.3. Apply 16 g of the mixture (1 part of control conventional bleaching powder (Table 4.1) and 2 parts of the control 40 volume developer (Table 5.2) for 50 minutes, while wrapped in aluminum foil at 35° C. The hair to bleach mixture ratio is 1 :4.4. Rinse the hair with tepid water for 3 minutes.5. Apply 5g of non-conditioning shampoo (Table 5.3) for 3 minutes and rinsed for 3 minutes and air-dry fibers, overnight.6. Determine the stress at 0.50% strain as in step 1 and determine the ratio of the stress (force) before and after treatment to determine the ISR.

[0076] The results of the control study are summarized below in Table 5.4.Table 5.4 (Control)

[0077] These results show that the strength of hair fibers in the control study on average retained only 88% of their original elasticity. The hair fibers in the control study exhibited considerable loss of strength after a conventional lightening procedure.

[0078] For the test hair fibers treated according to the invention, the conventional powder lightener was modified by the inclusion of the compound of Formula lb at different concentrations as shown below in Table 5.5.Table 5.5 (Invention)

[0079] For the treatment procedure according to the invention, the conventional developer formula (Table 5.2) was weighed at 60.0 g in a mixing bowl and 30.0 g of Lightener 1, Lightener 2, or Lightener 3 (Table 5.5) were added to the mixing bowl. This mixture was stirred well using an applicator brush until the mixture became smooth. The application procedure was as follows:1. Pre-test the untreated hair specimens on DMA, at 100% humidity, using the intermittent stress relaxation test.2. Embed the pre-tested hair fibers (Caucasian, IMHAIR) on a 4 g of hair tress.3. Apply 16 g of the above mixtures of bleaching powders (Table 5.5; Lightener 1, Lightener 2, or Lightener 3) and Control Developer 40 Volume (Table 5.2), which includes a compound of Formula lb, for 50 minutes to 4 g of hair, while wrapped in aluminum foil, at 35° C. The ratio of hair to bleaching mixture is 1 :4.4. After 50 minutes of processing, rinse hair with water for 3 minutes.5. Apply 5 g of non-conditioning shampoo (Table 5.3) for 3 minutes, rinse for 3 minutes, and air-dry fibers overnight.6. Determine the stress for 0.50% strain at 100% humidity, as in step 1 and determine the ratio of the stress (force) before and after treatment to determine the Index of Stress Relaxation.

[0080] The results of the treatment procedure according to the invention using Lightener 1 (sample size: 27 fibers), Lightener 2 (sample size: 27 fibers), and Lightener 3 (sample size: 25-27 fibers) are summarized below in Tables 5.6-5.8, respectively.Table 5.6 (Invention)Table 5.7 (Invention)Table 5.8 (Invention)

[0081] These results demonstrate that the compound of the invention not only mitigates loss in hair strength normally caused by conventional lightening / bleaching, but also may increase strength considerably enough for the hair to retain and even exceed the strength it had before lightening / bleaching, which is very surprising.EXAMPLE 6

[0082] This example demonstrates exemplary methods and compositions for treating hair in accordance with the invention. Hair strength following a conventional relaxer procedure (control) was compared with hair strength following the procedure in which the relaxer contained a compound of the invention.

[0083] A control group of hair fibers was treated with a non-conditioning formula of Guanidine Hydroxide Relaxer (control), Non-Conditioning Liquid Activator, and NonConditioning Neutralizing Shampoo. A test group of hair fibers was treated using a similar procedure except that the Guanidine Hydroxide Relaxer was modified to include a compound of Formula lb (invention). The ratio of relaxer cream to liquid activator was 3.78: 1.

[0084] The formulations of the relaxer cream, liquid activator, and neutralizing shampoo are described below in Tables 6.1-6.3, respectively.Table 6.1Sensitive Scalp Relaxer (control and invention)Table 6.2Conventional Liquid ActivatorTable 6.3Conventional Neutralizing Shampoo

[0085] The treatment procedure was as follows:1. On each 2g of hair tress, 8.0 g mixture of Non-conditioning Sensitive Scalp cream relaxer (Table 6.1, conventional / control or invention) plus Affirm Liquid Activator (Table 6.2) was applied.2. This relaxer cream mixture was left on the hair for 18 minutes.3. The treated fibers were rinsed after 18 minutes and shampooed twice with Non-Conditioning Neutralizing Shampoo (Table 6.3).4. The fibers were then rested overnight and the ISR was determined for the fibers.

[0086] The results of the control (conventional, sample size: 27 fibers) and test samples (invention, sample size: 27 fibers) are summarized below in Tables 6.4 and 6.5, respectively.Table 6.4 (Control)Table 6.5 (Invention)

[0087] These results demonstrate that the compound of the invention substantially mitigates loss in hair strength normally caused by conventional relaxer procedures. The fibers treated with sensitive scalp relaxer containing a compound of the invention exhibited a significant increase in elasticity.EXAMPLE 7

[0088] This example demonstrates an exemplary method of the invention. Hair strength following a conventional lightening procedure on untreated hair (control) was compared with hair strength following the lightening procedure on hair pretreated with a compound of the invention. For the test group, hair fibers were pretreated with 0.25 g, 0.50 g, and 0.75 g of Emulsion 2 (Table 3.2, containing 0.60 wt.% of the compound of Formula lb) per 4 g of hair before lightening (sample size: 27 fibers).

[0089] The application procedure was as follows:1. Wash the hair (Type 1 Hair, IM Hair, Italy) with non-conditioning shampoo.2. Pre-test the hair fibers on the DMA using the intermittent stress relaxation test.3. Embed the pre-tested hair fibers on a 4g hair tress.4. Apply 0.25 g, or 0.50 g, or 0.75 g of Emulsion 2 (Table 3.2), leave for 4 minutes, and dry hair.5. Mix conventional powder bleach (Table 5.1) (10g) with conventional 40- volume developer (Table 5.2) (20g) at 1 :2 ratio.6. Apply 16 g of this mixture to the 4g of hair tress, cover it with foil at 35° C and leave on for 50 minutes7. Shampoo the treated tress with 1 ,33g of conventional non-conditioning Shampoo (Table 5.3) for 3 minutes, rinse for 1 minute, and towel blot.8. Test fibers after 24 hours, at 100% humidity.

[0090] The results for the hair pretreated with 0.25 g, or 0.50 g, and 0.75 g of Emulsion 2 are shown below in Tables 7.1-7.3, respectively.Table 7.1Pretreatment with 0.25 g of Emulsion 2 per 4 g of HairTable 7.2Pretreatment with 0.50 g of Emulsion 2 per 4 g of HairTable 7.3Pretreatment with 0.75 g of Emulsion 2 per 4 g of Hair

[0091] These results demonstrate that pretreatment with a compound of the invention not only mitigates loss in hair strength normally caused by conventional lightening / bleaching, but also may increase strength considerably enough for the hair to retain and even exceed the strength it had before lightening / bleaching, which is very surprising. By contrast, hair fibers in the control study of Example 4 lost considerable strength, retaining on average only 88% of their original elasticity after lightening.EXAMPLE 8

[0092] This example demonstrates an exemplary method of the invention. Hair strength following a conventional permanent coloring procedure on untreated hair (control, sample size: 25 fibers, outliers eliminated) was compared with hair strength following the permanent coloring procedure on hair pretreated with a compound of the invention. For the test group, hair fibers were pretreated with 0.25 g of Emulsion 2 (Table 3.2, containing 0.60 wt.% of the compound of Formula lb) per 4 g of hair before permanent coloring (sample size: 27 fibers).

[0093] The control group was permanently colored using Wella 66 / 46 and Wella Developer 20 Volume (Batch No. 0919811144), for forty-five minutes, and then rinsed with water and shampooed using a Wella Color Protection Shampoo and Wella Conditioner (sample size: 25 fibers, outliers eliminated). The procedure for the control group was as follows:1. Wash the hair (IM Hair, Italy) with non-conditioning shampoo.2. Measure the diameter of the fibers with LaserMike® Optical Micrometer.3. Pre-test the hair fibers on the DMA using the intermittent stress relaxation test.4. Embed the pre-tested hair fibers on a 4 g hair tress.5. Prepare or mix the Wella Permanent Creme Hair Color, 66 / 46 hair color and 20 volume developer, batch no. 0919811144 at 1 : 1 ratio (10 g of color + 10 g of 20 vol. developer).6. Apply 12 g of this mixture to the 4 g of hair tress for 45 minutes.7. Shampoo the treated tress with 1.3 g of Wella Color Protection Shampoo, batch no. 200500 for 3 minutes and rinse for 1 minute and towel blot.8. Condition the hair with 2 g of Wella Conditioner, batch no. 204100 for 15 minutes, rinse with water for 1 minute, towel blot, and air-dry overnight.9. Perform intermittent stress relaxation on the treated hair fibers at 100% humidity.

[0094] The results of the control study are summarized below in Table 8.1.Table 8.1 (control)

[0095] The hair fibers in the control group exhibited a loss of strength, retaining on average only 93% of their original elasticity after permanent coloring.

[0096] The hair in the experimental group was pre-treated with 0.25 g of Emulsion 2 (Table 3.2, containing 0.60 wt.% of the compound of Formula lb) per 4 g of hair before permanent coloring (sample size: 27 fibers). The hair in the experimental group was permanently colored using Wella 66 / 46 and Wella Developer 20 Volume (Batch No. 0919811144), for forty -five minutes, and then rinsed with water and shampooed using a Wella Color Protection Shampoo and Wella Conditioner. The procedure for the experimental (test) group was as follows:1. Wash the hair (IM Hair, Italy) with non-conditioning shampoo.2. Measure the diameter of the fibers with LaserMike® Optical Micrometer.3. Pre-test the hair fibers on the DMA using the intermittent stress relaxation test4. Embed the pre-tested hair fibers on a 4 g hair tress.5. Apply 0.25 g of Emulsion 2 (Table 3.2) and wait until hair tress is completely dried.6. Prepare or mix the Wella Permanent Creme Hair Color, 66 / 46 hair color and 20 volume developer, batch no. 0919811144 at 1 : 1 ratio (10 g of color + 10 g of 20 vol. developer).7. Apply 12 g of this mixture to the 4 g of hair tress for 45 minutes.8. Shampoo the treated tress with 1.3 g of Wella Color Protection Shampoo, batch no. 200500 for 3 minutes, rinse for 1 minute, and towel blot.9. Condition the hair with 2 g of Wella Conditioner, batch no. 204100 for 15 minutes, rinse with water for 1 minute, towel blot, and air-dry overnight.10. Perform intermittent stress relaxation on the treated hair fibers, at 100% humidity.

[0097] The results of the test group are shown below in Table 8.2.Table 8.2 (invention)

[0098] These results demonstrate that pretreatment with compound of the invention not only mitigates loss in hair strength normally caused by permanent coloring, but also may increase strength considerably enough for the hair to retain and even exceed the strength it had before permanent coloring, which is very surprising. By contrast, hair fibers in the control group exhibited a loss in strength, retaining on average only 93% of their original elasticity after permanent coloring.EXAMPLE 9

[0099] This example demonstrates an exemplary method of the invention. Hair strength following a conventional lightening / bleaching procedure on untreated hair (control, sample size: 12 tresses) was compared with hair strength following the permanent coloring procedure on hair pretreated with a compound of the invention. For the test group, hair tresses were treated with 0.375 g of Emulsion 2 (Table 3.2, containing 0.60 wt.% of the compound of Formula lb) per 3 g of hair before and after lightening / bleaching (sample size: 12 tresses).

[0100] The tresses in the control group were lightened using bleaching powder, 30 volume hydrogen peroxide developer for forty-five minutes, and then rinsed with water and shampooed using a non-conditioning shampoo. The procedure used for the control group is as follows:1. Mix the conventional powder bleach (Table 5.1) (30 g) with conventional 30- volume developer (60 g) at 1 :2 ratio and mix well.2. Apply 12 g of this mixture to a 3 g hair tress containing 2500 fibers, cover the tress with aluminum foil and let it sit for 45 minutes at 35° C.3. Remove the foil after 45 minutes, and rinse hair with tepid water for 3 minutes.4. Apply 3 g of non-conditioning shampoo (Table 5.3) for 3 min and then rinse the hair for 1 minute with water at a flow rate of 1 gallon per minute and a water temperature of 33° C.5. Towel blot and air dry the tress.6. Air dry the tresses at 45% RH and equilibrate over night at 45% RH.7. Test the hair using the Repeated Brushing Test described herein, where brushing is done for total of 10,000 strokes, broken fibers are counted every 1000 strokes, and the number broken fibers from each tress at every 1000 strokes is recorded.

[0101] The results for the test group are provided in Table 9.1.Table 9.1 (control)

[0102] The tresses in the test group were treated with Emulsion 2 (Table 3.2) before and after treating the tresses with the hair lightening mixture, as follows:1. Apply 0.375 g of Emulsion 2 (Table 3.2) to 3 g hair tress containing 2500 fibers, and air-dry hair for 2 hours.2. Mix the conventional powder bleach (Table 5.1) (30 g) with the 30-volume developer (60 g) at 1 :2 ratio and mix well.3. Apply 12 g of this mixture to a 3 g of hair tress, cover the tress with aluminum foil and let it sit for 45 minutes at 35° C.4. Remove the foil after 45 minutes, and rinse hair with tepid water for 3 minutes.5. Apply 3 g of non-conditioning shampoo (Table 5.3) for 3 min and then rinse the hair for 1 minute with water at a flow rate of 1 gallon per minute and a water temperature of 33° C.6. Towel blot the tresses, and apply 0.375 g of Emulsion 2 (Table 3.2) and leave on for 30 minutes.7. Rinse the hair tress for 1 minute with water at a flow rate of 1 gallon per minute and a water temperature of 33° C.8. Air dry the tresses at 45% RH and equilibrate over night at 45% RH.9. Test the hair using the Repeated Brushing Test described herein, where brushing is done for total of 10,000 strokes, broken fibers are counted every 1000 strokes, and the number broken fibers from each tress at every 1000 strokes is recorded.

[0103] The results for the experimental (test) group are provided in Table 9.2.Table 9.2 (invention)

[0104] The tresses treated with a compound of the invention exhibited significantly fewer broken fibers after lightening when brushed for a total of 10,000 brushing strokes at 1,000 stokes per interval. These results demonstrate that the compound of the invention is highly effective in reducing hair breakage.EXAMPLE 10

[0105] This example demonstrates an exemplary method of the invention. Hair strength following treatment with a conventional shampoo (control) was compared with hair strength following treatment with the shampoo containing 0.25 wt.%, 0.50 wt.%, and 0.75 wt.% of the compound of Formula lb (invention). The shampoo formulations used in the study are described below in Table 10.1.Table 10.1 (Shampoo Formulations)

[0106] Hair fiber samples (sample size 27) were treated with the shampoo formulations described in Table 10.1. Hair fiber elasticities were determined before and after treatment with each shampoo. The results of the control study are summarized below in Table 10.2.Table 10.2 (Control)

[0107] The results before and after treatment with Shampoos 1-3 of the invention are summarized below in Tables 10.3, 10.4, and 10.5, respectively.Table 10.3 (Shampoo 1 (invention))Table 10.4 (Shampoo 2 (invention))Table 10.5 (Shampoo 3 (invention))

[0108] These results demonstrate that the shampoo of the invention improved hair strength / elasticity considerably relative to the control (conventional) shampoo.EXAMPLE 11

[0109] This example demonstrates an exemplary method of the invention. Hair strength following treatment with a conventional leave-in conditioner (control) was compared with hair strength following treatment with the conditioner containing 0.125 wt.%, 0.25 wt.%, 0.50 wt.%, 0.75 wt.%, and 1.00 wt.% of the compound of Formula lb (invention). The conditioner formulations used in the study are described below in Table 11.1.Table 11.1 (Conditioner Formulations)

[0110] Hair fiber samples (sample size 27) were treated with the conditioner formulations described in Table 11.1. Hair fiber elasticities were determined before and after treatment with each conditioner. The conditioners used in the study were applied as follows:1. Wash the hair (IM Hair, Italy) with non-conditioning shampoo and dry at room temperature.2. Measure the diameter of the fibers with LaserMike® Optical Micrometer3. Pre-test the hair fibers on the DMA using the intermittent stress relaxation test4. Embed the pre-tested hair fibers on a 4 g hair tress.5. Apply 0.50 g of the Leave-In Conditioners to the 4 g of hair tress and leave on the hair.6. Perform ISR test on the treated hair fibers at 100% humidity.[OHl] The results of the control study are summarized below in Table 11.2.Table 11.2 (Control)

[0112] The results before and after treatment with Conditioners 1-5 of the invention are summarized below in Tables 11.3 through 11.7, respectively.Table 11.3 (Conditioner 1 (invention))Table 11.4 (Conditioner 2 (invention))Table 11.5 (Conditioner s (invention))Table 11.6 (Conditioner 4 (invention))Table 11.7 (Conditioner 5 (invention))

[0113] These results demonstrate that the conditioner of the invention improved hair strength / elasticity considerably relative to the control (conventional) conditioner.

[0114] All references, including publications, patent applications, and patents, cited herein are hereby incorporated by reference to the same extent as if each reference were individually and specifically indicated to be incorporated by reference and were set forth in its entirety herein.

[0115] The use of the terms “a” and “an” and “the” and “at least one” and similar referents in the context of describing the invention (especially in the context of the following claims) are to be construed to cover both the singular and the plural, unless otherwise indicated herein or clearly contradicted by context. The use of the term “at least one” followed by a list of one or more items (for example, “at least one of A and B”) is to be construed to mean one item selected from the listed items (A or B) or any combination of two or more of the listed items (A and B), unless otherwise indicated herein or clearly contradicted by context. The terms “comprising,” “having,” “including,” and “containing” are to be construed as open-ended terms (i.e., meaning “including, but not limited to,”) unless otherwise noted. Recitation of ranges of values herein are merely intended to serve as ashorthand method of referring individually to each separate value falling within the range, unless otherwise indicated herein, and each separate value is incorporated into the specification as if it were individually recited herein. All methods described herein can be performed in any suitable order unless otherwise indicated herein or otherwise clearly contradicted by context. The use of any and all examples, or exemplary language (e.g., “such as”) provided herein, is intended merely to better illuminate the invention and does not pose a limitation on the scope of the invention unless otherwise claimed. No language in the specification should be construed as indicating any non-claimed element as essential to the practice of the invention.

[0116] Preferred embodiments of this invention are described herein. Variations of those preferred embodiments may become apparent to those of ordinary skill in the art upon reading the foregoing description. The inventors expect skilled artisans to employ such variations as appropriate, and the inventors intend for the invention to be practiced in ways not limited to the embodiments specifically described herein. Accordingly, this invention includes all modifications and equivalents of the subject matter recited in the claims appended hereto as permitted by applicable law. Moreover, any combination of the abovedescribed elements in all possible variations thereof is encompassed by the invention unless otherwise indicated herein or otherwise clearly contradicted by context.

Claims

CLAIM(S):wherein a is from 0 to 4, and b is from 1 to 4, provided that the sum of a and b is at least 2, and R is alkyl.

2. The compound of claim 1, wherein R is C11-C21 alkyl.

3. The compound of claim 1, wherein R is C17-C21 alkyl.

4. The compound of any one of claims 1-3, wherein a is from 1 to 4, and b is from 1 to 4.

5. The compound of claim 4, wherein a is from 1 to 2.

6. The compound of claim 5, of the formula:wherein b is from 1 to 2.

7. The compound of claim 6, of the formula:wherein a is from 1 to 2, b is from 1-2, and the sum of a and b is 3, orwherein a is from 1 to 2, b is from 1-2, and the sum of a and b is 3.

8. A method for treating hair, the method comprising contacting hair fibers with an effective amount of the compound of any one of claims 1-7, to treat the hair.

9. The method of claim 8, comprising mending the hair fibers.

10. The method of claim 8, comprising increasing the strength of the hair fibers, increasing the elasticity of the hair fibers, increasing the resistance of hair fibers to breakage, or a combination thereof.

11. The method of claim 8, comprising increasing the resistance of the hair fibers to damage associated with a hair altering procedure that may be damaging to hair.

12. The method of claim 8, comprising increasing the resistance of the hair fibers to damage associated with bleaching, lightening, straightening / relaxing, oxidative dyeing, permanent coloring, permanent waving, or keratin smoothing.

13. The method of claim 8, comprising increasing the resistance of the hair fibers to damage associated with combing, brushing, or blow-drying, or exposure to environmental conditions that may be damaging to hair.

14. The method of claim 8, comprising contacting the hair fibers with an effective amount of the compound before, during, or after a hair altering procedure that may be damaging to hair.

15. The method of claim 8, comprising contacting the hair fibers with an effective amount of the compound before, during, or after combing, brushing, or blow-drying, or exposure to environmental conditions that may be damaging to hair.

16. A composition comprising a carrier and an effective amount of the compound of any one of claims 1-7.

17. The composition of claim 16, comprising one or more diluents, excipients, vehicles, additives, fillers, texturing agents, pigments, dyes, coloring agents, or a combination thereof18. The composition of claim 16, comprising one or more hair altering agents that may be damaging to hair.

19. The composition of claim 16, comprising one or more oxidative hair lightening / bleaching agents, hair relaxing agents, oxidative hair dyeing or permanent coloring agents, permanent waving agents, smoothing agents, or a combination thereof.

20. The composition of claim 16, comprising from about 0.01 wt.% to about 25 wt.% of the compound.

21. The composition of claim 16, comprising from about 0.1 wt.% to about 25 wt.% of the compound.

22. The composition of claim 16, comprising from about 0.1 wt.% to about 10 wt.% of the compound.

23. The composition of claim 16, comprising from about 0.1 wt.% to about 5 wt.% of the compound.

24. The composition of claim 16, in the form of an emulsion.

25. The composition of claim 16, in the form of an aqueous emulsion.

26. The composition of any one of claims 17-25, comprising one or more dispersants, emulsifiers, surfactants, or a combination thereof.

27. A product comprising an effective amount of the compound of any one of claims 1-7, and instructions for applying the compound to the hair.

28. The product of claim 27, further comprising a hair care or hair altering agent.

29. The product of claim 27, further comprising a hair altering agent that may be damaging to hair.

30. The product of claim 30, wherein the hair altering agent comprises one or more oxidative hair lightening agents, hair relaxing agents, oxidative hair dyeing or permanent coloring agents, or a combination thereof.

31. The product of any one of claims 28-30, comprising instructions for applying the compound of Formula I before, during, or following application of the hair care or hair altering agent to the hair.

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