Hair styling compositions and hair styling processes

FR3159322B3Active Publication Date: 2026-03-13LOREAL SA
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Authority / Receiving Office
FR · FR
Patent Type
Utility models
Current Assignee / Owner
Filing Date
2024-02-21
Publication Date
2026-03-13
Patent Text Reader

Abstract

Hair Styling Compositions and Processes This disclosure relates to hair styling compositions and processes, including: (i) the application of a hair styling composition according to this disclosure to the hair; (ii) the physical manipulation of the hair onto which the hair styling composition is applied into a desired shape; and (iii) without removing the hair styling composition from the hair, the drying of the hair and, optionally, the heating of the hair. The hair styling composition includes: (a) citric acid, one of its salts, or a combination thereof; (b) one or more cyclodextrins, their derivatives, or a combination thereof; (c) one or more water-soluble solvents; (d) one or more cationic guar derivatives; and (e) water.Hair treated with hair-styling products has a desired shape and also exhibits improved fiber alignment, frizz control, and a smooth texture. Figure for the summary: none.
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Description

Title of the invention: Hair shaping compositions and methods of hair shaping FIELD OF DISCLOSURE

[0001] The present disclosure relates to hair styling compositions and methods of styling hair. Hair treated with the compositions exhibits improved fiber alignment, frizz control, and smooth texture. CONTEXT

[0002] Many consumers use cosmetic and care compositions to enhance the appearance of hair, for example, by changing the color, style and / or shape of the hair and / or by imparting various cosmetic properties to the hair, such as shine and conditioning. Hair can become dry or damaged for a variety of reasons, for example, exposure to the elements, poor nutrition, mechanical treatments (e.g., brushing the hair), styling treatments using chemicals, dyeing, heat, nutrition, etc. Even cleansing shampoos can strip the hair of its natural oils causing dryness, which can lead to dullness and frizz.

[0003] Chemical hair treatments include bleaching and coloring treatments to change the color of the hair. Chemical treatments also include processes to permanently change the shape and structure of the hair, for example, by perming, waving, relaxing, or straightening the hair. These chemical treatments often alter the appearance of the hair by changing its physical structure, which inevitably causes some degree of damage to the hair. Environmental factors, such as salt water, sunlight, and heat, are also known to damage hair. Damaged hair is characterized by unnatural changes in the protein structure of individual hair strands or shafts.

[0004] The popularity and use of oils for hair treatment has increased due to their effectiveness and simplicity. Commonly used oils include olive oil, mineral oil, avocado oil, apricot kernel oil, rice bran oil, and coconut oil. However, these treatments can leave the hair feeling greasy. Furthermore, effects are usually not seen until several hours (e.g., 8 hours) of treatment and multiple treatments are usually required, making the treatment time-consuming and laborious.

[0005] Hair damage results in split ends, dryness, hair that breaks easily, and hair that becomes "frizzy" and difficult to style. Because the visible part of the hair is dead, it cannot regenerate itself. Many over-the-counter and salon treatments are claimed to repair damaged hair. These include conditioners, hot oil treatments, hydrolyzed proteins, vitamin formulations, and extracts of exotic fruits, leaves, or roots. However, these treatments provide only limited improvement to the hair. Therefore, hair treatment technologies that can shape, curl, straighten, relax, or style hair without chemically damaging it are desired.

[0006] The need remains to improve the curling, waving, shaping, straightening, smoothing and manageability of hair, for example, to improve hair alignment, reduce unwanted volume (particularly a reduction in frizz) and increase shine.

[0007] Furthermore, the formulation of environmentally friendly cosmetic products, which are designed and developed with environmental issues in mind, is becoming a major objective in an effort to address global challenges. It is, therefore, essential to provide more sustainable compositions, preparation processes and ingredients to address these environmental concerns. In this context, it is important to develop new cosmetic compositions with a better carbon footprint, in particular by promoting the use of renewable raw materials and / or materials with a good naturalness index and / or materials of natural origin and, more particularly, materials of plant origin while reducing the use of compounds of petrochemical origin. SUMMARY OF DISCLOSURE

[0008] The present disclosure relates to hair shaping compositions and methods of shaping and straightening hair, for example, curling hair. Hair treated with the compositions has a desired shape while exhibiting improved fiber alignment, reduced frizz, and a smooth texture. Furthermore, the hair is soft, shiny, conditioned, and has a healthy appearance. The compositions include a combination of citric acid, or a salt thereof, and a cyclodextrin or a derivative thereof. The citric acid, or its salt, and the cyclodextrin, or its derivative, are separately combined with each other, and the cyclodextrin or derivative is dissolved in the citric acid. Thereafter, the combination is incorporated into the hair shaping composition.

[0009] Hair styling compositions typically include: a. citric acid, one of its salts, or one of their combinations; b. one or more cyclodextrins, their derivatives or a combination thereof; c. one or more water-soluble solvents; d. one or more cationic guar derivatives; and e. water.

[0010] Citric acid and its salts provide many benefits to the hair. For example, it acts as an antioxidant, removes buildup and debris from the hair, and improves blood circulation in the scalp, which in turn nourishes the hair follicles and promotes growth. Its acidic pH is also helpful in balancing the pH of the scalp, as many hair care products are alkaline. The citric acid in the present hair shaping composition also interacts with cyclodextrin in a unique way and enhances film formation on the hair, which is further potentiated by heat.

[0011] Cyclodextrins are a family of cyclic oligosaccharides composed of a macrocyclic core of glucose subunits joined by α-1,4 glycosidic linkages. Cyclodextrins are produced from starch by enzymatic conversion. Typical cyclodextrins contain a number of glucose monomers ranging from six to eight units in a core, creating a cone shape, e.g., α(alpha)-cyclodextrin has 6 glucose subunits, β(beta)-cyclodextrin has 7 glucose subunits, and γ(gamma)-cyclodextrin has 8 glucose subunits. Non-limiting examples of cyclodextrins for use in the compositions of the present disclosure include α-cyclodextrin, β-cyclodextrin, γ-cyclodextrin, methyl-α-cyclodextrin, methyl-β-cyclodextrin, methyl-γ-cyclodextrin, and mixtures thereof.

[0012] The weight ratio of citric acid, its salts, or the combination of (a) to cyclodextrin or derivatives of (b) is typically from about 4:1 to about 1:1 ((a):(b)) and / or the molar ratio of citric acid, its salts, or the combination of (a) to cyclodextrin or derivatives of (b) is typically from about 20:1 to about 5:1 ((a):(b)).

[0013] Citric acid, its salts, or a combination of (a) and cyclodextrin, its derivatives, or a combination thereof of (b) are generally combined with each other before being combined with the other ingredient of the hair styling composition. For example, cyclodextrin and / or its derivatives (cyclodextrin component) are preferably dissolved or solubilized in citric acid, a salt thereof, or combinations thereof (citric acid component) to form a solubilized combination of citric acid and cyclodextrin. The combination of the cyclodextrin component and the citric acid component may be heated to facilitate or accelerate the dissolution of the cyclodextrin component in the citric acid component. When the component cyclodextrin is individually dissolved in the citric acid component before being combined with other ingredients of the hair styling compositions, the cyclodextrin / citric acid component provides unique properties to the hair styling composition that differ from the properties that result from combining the cyclodextrin component and the citric acid component with the other ingredients of the composition without first dissolving the cyclodextrin component in the citric acid component.

[0014] Non-limiting examples of water-soluble solvents include C2-C6 monohydric alcohols (e.g., ethanol, isopropyl alcohol, etc.), polyols (polyhydric alcohols), glycerin, glycols (e.g., ethylene glycol, propylene glycol, butylene glycol, pentylene glycol, caprylyl glycol, etc.), and mixtures thereof. Glycerin, also known as glycerol, is a simple triol (C3H8O3). It is a colorless, odorless, and viscous liquid that acts as a natural humectant by attracting moisture from its surroundings.

[0015] Cationic guar derivatives include modified cationic guar, hydroxypropyl guar, and alkyl guar, including cationic hydroxypropyl guar, and salts thereof. A typical cationic functional group in these cationic guar derivatives is trimethylamino(2-hydroxyl)propyl, with a counterion such as a halide (e.g., chloride, fluoride, bromide, iodide), sulfate, or methyl sulfate. Non-limiting examples of cationic guar derivatives include cationically modified alkylated carboxylated polymers such as methyl and ethyl carboxymethyl guar and cationic hydroxypropyl guar, including cationic hydroxypropyl guar.

[0016] The hair shaping compositions are aqueous compositions containing significant amounts of water. In addition to water, the compositions optionally include one or more water-soluble solvents other than glycerin. Non-limiting examples of water-soluble solvents include C2-C6 monohydric alcohols (e.g., ethanol, isopropyl alcohol, etc.), polyols (polyhydric alcohols), glycols (e.g., ethylene glycol, propylene glycol, butylene glycol, pentylene glycol, caprylyl glycol, etc.), and mixtures thereof. In various embodiments, at least one of the one or more water-soluble solvents is glycerin, a glycol (e.g., ethylene glycol, propylene glycol, butylene glycol, pentylene glycol, caprylyl glycol, etc.), or mixtures thereof.

[0017] The pH of the hair styling compositions is typically acidic, for example, from about 3 to about 6.5, preferably from about 3 to about 6, more preferably from about 3 to about 5.

[0018] The hair styling composition may optionally include one or more miscellaneous ingredients, for example one or more preservatives, perfumes, pH adjusters, salts, chelating agents, buffers, antioxidants, flavonoids, vitamins, amino acids, botanical extracts, UV filtering agents, peptides, proteins, protein hydrolysates and / or isolates, fillers (e.g., organic and / or inorganic fillers such as talc, calcium carbonate, silica, special materials, etc.), emollients, composition colorants or mixtures thereof.

[0019] Methods of shaping hair using the hair shaping compositions include: i. applying a hair styling composition of the present disclosure to hair; ii. the physical manipulation of the hair to which the hair shaping composition is applied to give the hair a desired shape; iii. without rinsing the hair styling composition, drying the hair and iv. optionally, heating the hair, wherein the heating of the hair may optionally be carried out after a pause time.

[0020] The hair shaping composition is applied to the hair and the hair is physically manipulated to achieve a desired shape. For example, the hair may be rolled on curlers to curl it, the hair may be combed, brushed or pulled, for example, with the fingers and hands, to curl or straighten it. In addition, a round brush may be used to roll the hair while drying it to form curls or waves in the hair. The hair shaping composition may be massaged or distributed throughout the hair with an individual hand, a comb or brush may be used to distribute the hair shaping composition evenly throughout the hair.

[0021] The hair is physically manipulated into a desired shape. For example, to curl the hair, the hair may be wound onto curlers. Once the hair is manipulated into a desired shape, the hair is dried while being held in the desired shape. For example, damp or wet hair to which the hair-shaping composition is applied may be wound around curlers and dried while being wound around the curlers. The hair may dry naturally under ambient conditions, for example, at a temperature of about 25°C. Once dry, the hair may be removed from the curlers. The hair may optionally be treated with a heat treatment (a thermal treatment) to dry and / or to shape the hair. A thermal treatment is not required, but in various embodiments, a thermal treatment is preferred.

[0022] The heat treatment may be preceded by a dwell time. A "dwell time" is a time delay between applying the hair-styling composition to the hair and treating the hair with a heat treatment. For example, the hair-styling composition may be applied to the hair, after which a dwell time is practiced before treating the hair with a heat treatment. The dwell time begins after the hair-styling composition has been applied to the hair before the hair is dry. After the dwell time, the hair is treated with a heat treatment, for example, with blow-drying or a hot iron such as a curling iron or flat iron at a temperature of about 140°C to about 220°C.The heat treatment may be used to assist in drying the hair and assist in shaping the hair or the heat treatment may be applied to the hair after the hair has dried, for example, after a leave-on time. The leave-on time may vary, but is generally from about 1 minute to about 2 hours. In a preferred embodiment, the hair is treated with a hair shaping composition and after a leave-on time of from about 1 minute to about 1 hour, the hair is treated with a heat treatment, wherein the heat treatment is preferably a treatment with a hot iron, such as a curling iron or a flat iron. The hair may dry naturally during the leave-on time or be blow-dried. Brief description of the drawings

[0023] An implementation of the present technology is described, by way of example only, with reference to the accompanying figures, in which:

[0024] [Fig-1] [Fig.l]shows the holding of curls of hair strands treated with a inventive composition or a control after 5 minutes, 30 minutes, 24 hours, 24 hours and 96 hours in an 80% relative humidity chamber at 23°C.

[0025] [Fig.2] [Fig.2] compares the curl length of hair strands treated with an inventive composition or a control after 5 minutes, 30 minutes, 24 hours, 24 hours and 96 hours in an 80% relative humidity chamber at 23°C.

[0026] [Fig.3] [Fig.3] shows the holding of curls of hair strands treated with a inventive composition or a control and a curling iron after 5 minutes, 30 minutes, 24 hours, 24 hours and 96 hours in an 80% relative humidity chamber at 23°C.

[0027] [Fig.4] [Fig.4] compares the curl length of hair strands treated with an inventive composition or a control and a curling iron after 5 minutes, 30 minutes, 24 hours, 24 hours and 96 hours in an 80% relative humidity chamber at 23°C.

[0028] It should be understood that the various aspects are not limited to the arrangements and instrumentality shown in the drawings. DETAILED DESCRIPTION OF THE INVENTION

[0029] The present disclosure relates to hair shaping compositions and methods of shaping hair. Hair treated according to the disclosure has a desired shape and exhibits improved fiber alignment, reduced frizz, and a smooth texture. The shaping effect may be enhanced by heat, for example, with a hot iron, but heating is not necessary. Whether heat is used or not, the hair shape is long-lasting and durable, even in high humidity conditions.

[0030] The hair shaping composition typically includes: a. about 1 to about 8% by weight of citric acid, a salt thereof, or a combination thereof; b. about 0.5 to about 5% by weight of one or more cyclodextrins, their derivatives, or a combination thereof;

[0031] wherein a combined total amount of (a) and (b) is about 2 to about 12% by weight; a. about 0.1 to about 5% by weight of glycerin; b. about 0.1 to about 8% by weight of one or more guar derivatives cationic; and c. about 70 to 96% by weight of water;

[0032] wherein all weight percentages are based on a total weight of the composition.

[0033] The hair shaping composition is used in methods of shaping hair. The manner in which the hair is shaped is not limited. However, in various embodiments, the hair shaping composition is used to curl the hair. In various embodiments, the hair shaping composition is used to straighten the hair. Methods of shaping hair include: i. applying to hair a hair styling composition according to the present disclosure; ii. the physical manipulation of the hair to which the hair shaping composition is applied to achieve a desired shape; and iii. without removing the hair styling composition, drying the hair and, optionally, treating the hair with a heat treatment, wherein the heat treatment is optionally preceded by a pause time. a. Citric acid and its salts#

[0034] The total amount of citric acid, its salts, or a combination thereof will vary. However, in various embodiments, the hair styling composition includes about 1 to about 8% by weight of citric acid, its salts, or a combination thereof, based on a total weight of the composition.In other embodiments, the hair shaping composition includes about 1 to about 6 wt. %, about 1 to about 4 wt. %, about 1 to about 3 wt. %, about 2 to about 8 wt. %, about 2 to about 6 wt. %, about 2 to about 5 wt. %, about 2 to about 4 wt. %, about 2 to about 3 wt. %, about 2.5 to about 8 wt. %, about 2.5 to about 6 wt. %, about 2.5 to about 5 wt. %, about 2.5 to about 4 wt. %, about 2.5 to about 3 wt. %, or about 1, about 1.5, about 2, about 2.5, about 3, about 3.5, about 4, about 4.5, or about 5 wt. % of citric acid, its salts, or a combination thereof, based on a weight total composition. . a. Cyclodextrin and derivatives#

[0035] Hair styling compositions include one or more cyclodextrins or their derivatives. As used herein, the term "cyclodextrins" includes carboxylic acid salts, whether or not expressly indicated. Cyclodextrins are a family of cyclic oligosaccharides composed of a macrocyclic core of glucose subunits joined by α-1,4 glycosidic linkages.

[0036] Cyclodextrins that may be used include those of the formula:

[0037] in which: • R is chosen from H, CH3 or a hydroxypropyl group, and • n goes from 6 to 8.

[0038] For example, in embodiments where R = H, the cyclodextrin may be α-cyclodextrin (n = 6), β-cyclodextrin (n = 7), or γ-cyclodextrin (n = 8). For example, α-cyclodextrin sold by WACKER under the name CAVAMAX W6 PHARMA, β-cyclodextrin sold by WACKER under the name CAVAMAX W7 PHARMA, or γ-cyclodextrin sold by WACKER under the name CAVAMAX W8 PHARMA may be used.

[0039] In other embodiments where R = CH3, the cyclodextrin may be a methyl-cyclodextrin, such as methyl-α-cyclodextrin (n = 6), methyl-β-cyclodextrin (n = 7) or methyl-γ-cyclodextrin (n = 8). For example, methyl-β-cyclodextrin sold by the company WACKER under the name CAVASOL W7 may be chosen.

[0040] In various embodiments, the at least one cyclodextrin may comprise a mixture of cyclodextrins and / or derivatives thereof. For example, the at least one cyclodextrin may be a mixture of α-cyclodextrin, β-cyclodextrin and / or γ-cyclodextrin. In another embodiment, the at least one cyclodextrin includes β-cyclodextrin. In yet another embodiment, the cyclodextrin is only β-cyclodextrin, and no other cyclodextrin or derivative thereof is present in the composition.

[0041] In one embodiment, the hair shaping compositions according to the present disclosure include B-cyclodextrin in an amount ranging from about 0.1% to about 10%, such as from 0.2% to about 8%, from about 0.3% to about 7%, from about 0.4% to about 6%, from about 1% to about 10%, from about 1% to about 8%, from about 1% to about 5%, from about 1% to about 3% by weight, based on the total weight of the hair shaping composition.

[0042] The total amount of cyclodextrin in the hair shaping compositions will vary. However, in various embodiments, the hair shaping composition includes about 0.5 to about 5% by weight of cyclodextrin, based on a total weight of the composition.In other embodiments, the hair shaping composition comprises 0.5 to about 4 wt.%, about 0.5 to about 3 wt.%, about 0.5 to about 2 wt.%, about 1 to about 5 wt.%, about 1 to about 4 wt.%, about 1 to about 3 wt.%, about 1 to about 2 wt.%, about 1.5 to about 5 wt.%, about 1.5 to about 4 wt.%, about 1.5 to about 3 wt.%, about 1.5 to about 2 wt.%, about 0.5 wt.%, about 1 wt.%, about 1.25 wt.%, about 1.5 wt.%, about 2 wt.%, about 2.5 wt.%, about 3 wt.%, about 3.5 wt.%, about 4 wt.%, about 4.5 wt.% or about 5 wt.%, relative to to a total weight of the composition. .

[0043] Combination of citric acid / salts and cyclodextrin

[0044] The total combined amount of the citric acid, its salts, or the combination of (a) and the cyclodextrin or derivatives of (b) will vary. However, in various embodiments, the total combined amount of the citric acid, its salts, or the combination of (a) and the cyclodextrin and derivatives of (b) is from about 1 to about 12% by weight, based on a total weight of the hair styling composition. In other embodiments, the total combined amount of the citric acid, its salts, or the combination of (a) and the cyclodextrin and derivatives of (b) is from about 1 to about 12% by weight, based on a total weight of the hair styling composition. citric acid, its salts or the combination of (a) and cyclodextrin and derivatives of (b) is about 1 to about 10% by weight, about 1 to about 8% by weight, about 1 to about 6% by weight, about 1 to about 5% by weight, about 2 to about 12% by weight, about 2 to about 10% by weight, about 2 to about 8% by weight, about 2 to about 6% by weight, about 2 to about 5% by weight, about 3 to about 12% by weight, about 3 to about 10% by weight, about 3 to about 8% by weight, about 3 to about 6% by weight, about 3 to about 5% by weight, or about 1% by weight, 2% by weight, 3% by weight, 4% by weight weight, 5% by weight, 6% by weight, 7% by weight or 8% by weight, relative to a total weight of the hair shaping composition.

[0045] The weight ratio of citric acid, its salts, or the combination of (a) to cyclodextrin or derivatives of (b) will vary. However, in various embodiments, the citric acid, its salts, or the combination of (a) to cyclodextrin or derivatives of (b) are in a weight ratio of about 8:1 to about 1:2 ((a):(b)). In other embodiments, the citric acid, its salts, or a combination of (a) to cyclodextrin or derivatives of (b) are in a weight ratio of about 6:1 to about 1:2, about 5:2 to about 1:2, about 4:1 to about 1:2, about 3:1 to about 1:2; from about 2:1 to about 1:2, from about 8:1 to about 1:1, from about 6:1 to about 1:1, from about 5:1 to about 1:1, from about 4:1 to about 1:1, from about 3:1 to about 1:1, from about 2:1 to about 1:1, from about 1.2:1, about 1.3:1, about 1.4:1, about 1.5:1, about 1.6:1 or about 1.8:1 ((a):(b)).

[0046] The molar ratio between citric acid, its salts or the combination of (a) and cyclodextrin or derivatives of (b) will vary. However, in various embodiments, citric acid, its salts, or the combination of (a) and cyclodextrin or derivatives of (b) are in a molar ratio of about 20:1 to about 3:1. In other embodiments, the citric acid, its salts, or a combination of (a) and the cyclodextrin or derivatives of (b) are in a molar ratio of about 18:1 to about 3:1, about 15:1 to about 3:1, about 20:1 to about 5:1, about 18:1 to about 5:1, about 15:1 to about 5:1, about 20:1 to about 8:1, about 18:1 to about 8:1, about 15:1 to about 8:1, about 20:1 to about 10:1, about 18:1 to about 10:1, about 15:1 to about 10:1, about 14:1 to about 13:1, or about 12:1 to about 11:1.

[0047] In various embodiments, citric acid, its salts, or the combination of (a) and the cyclodextrin of (b) are combined with each other before being added to the hair styling compositions of the present disclosure. For example, the cyclodextrin is preferably solubilized in citric acid to form a solubilized combination of citric acid and cyclodextrin. The combination may be heated to facilitate or accelerate dissolution of the cyclodextrin. The solubility of Cyclodextrin in water is not always ideal. Therefore, combining cyclodextrin with citric acid and dissolving the cyclodextrin in citric acid before adding the combination with other components of the hair styling composition can be beneficial. a. Water-soluble solvent#

[0048] The term "water-soluble organic solvent" is interchangeable with the terms "water-soluble solvent" and "water-miscible solvent" and means a compound that is liquid at 25°C and atmospheric pressure (760 mmHg), and has a solubility of at least 50% in water under these conditions. In some cases, water-soluble solvents have a solubility of at least 60%, 70%, 80% or 90%. Non-limiting examples of water-soluble solvents include, for example, organic solvents selected from glycerin, alcohols (e.g., C1-8, C1-4 alcohols), polyols (polyhydric alcohols), glycols and a mixture thereof.

[0049] Non-limiting examples of water-soluble organic solvents. Non-limiting examples of water-soluble organic solvents include, for example, organic solvents selected from alcohols (e.g., C 10 , C 15 , or C 14 alcohols), polyols (polyhydric alcohols), glycols, and a mixture thereof. Non-limiting examples of monoalcohols and polyols include ethyl alcohol, isopropyl alcohol, propyl alcohol, benzyl alcohol and phenylethyl alcohol, or glycols or glycol ethers such as, for example, monomethyl, monoethyl and monobutyl ethers of ethylene glycol, propylene glycol or their ethers such as, for example, monomethyl ether of propylene glycol, butylene glycol, hexylene glycol, dipropylene glycol, as well as alkyl ethers of diethylene glycol, for example, monoethyl ether or monobutyl ether of diethylene glycol.Other suitable examples of organic solvents are ethylene glycol, propylene glycol, butylene glycol, hexylene glycol and propane diol.

[0050] Other non-limiting examples of water-soluble organic solvents include alkanediols (polyhydric alcohols) such as 1,2,6-hexanetriol, trimethylolpropane, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol, dipropylene glycol, 2-butene-1,4-diol, 2-ethyl-1,3-hexanediol, 2-methyl-2,4-pentanediol, (caprylyl glycol), 1,2-hexanediol, 1,2-pentanediol and 4-methyl-1,2-pentanediol; alkyl alcohols having 1 to 4 carbon atoms such as ethanol, methanol, butanol, propanol and isopropanol; glycol ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monomethyl ether acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, ethylene glycol mono-iso-propyl ether, diethylene glycol mono-isopropyl ether, ethylene glycol mono-n-butyl ether, ethylene glycol mono-t-butyl ether, diethylene glycol mono-t-butyl ether, 1-methyl-l-methoxybutanol, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-t-butyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-isopropyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether and dipropylene glycol mono-isopropyl ether; 2-pyrrolidone, N-methyl-2-pyrrolidone, l,3-dimethyl-2-imidazolidinone, formamide, acetamide, dimethyl sulfoxide, sorbit, sorbitan, acetin, diacetin, triacetin, sulfolane and a mixture thereof.

[0051] Polyhydric alcohols are useful. Examples of polyhydric alcohols include ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, 1,3-butanediol, 2,3-butanediol, 1,4-butanediol, 3-methyl-1,3-butanediol, 1,5-pentanediol, tetraethylene glycol, 1,6-hexanediol, 2-methyl-2,4-pentanediol, polyethylene glycol, 1,2,4-butanetriol, 1,2,6-hexanetriol and a mixture thereof. Polyol compounds may also be used. Non-limiting examples include aliphatic diols, such as 2-ethyl-2-methyl-1,3-propanediol, 3,3-dimethyl-1,2-butanediol, 2,2-diethyl-1,3-propanediol, 2-methyl-2-propyl-1,3-propanediol, 2,4-dimethyl-2,4-pentanediol, 2,5-dimethyl-2,5-hexanediol, 5-hexene-1,2-diol and 2-ethyl-1,3-hexanediol and a mixture thereof.

[0052] In a preferred embodiment, the hair smoothing composition includes one or more glycols selected from propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, caprylyl glycol, dipropylene glycol and mixtures thereof.

[0053] In a preferred embodiment, the hair smoothing composition includes glycerin.

[0054] The amount of water-soluble solvents in the hair-styling compositions will vary. However, the total amount of one or more water-soluble solvents may be from about 0.1 to about 20% by weight, based on the total weight of the hair-straightening composition. In other embodiments, the hair-styling composition comprises from about 0.1 to about 15% by weight, from about 0.1 to about 10% by weight, from about 0.1 to about 5% by weight, from about 1 to about 20% by weight, from about 1 to about 15% by weight, from about 1 to about 10% by weight, from about 1 to about 5% by weight, based on the total weight of the hair-styling composition.

[0055] In other embodiments, the hair shaping composition includes from about 0.1 to about 5% by weight of one or more water-soluble solvents, based on the total weight of the hair shaping composition. In other embodiments, the hair shaping composition comprises from about 0.1 to about 4% by weight, from about 0.1 to about 3% by weight, from about 0.1 to about 2% by weight, from about 0.2 to about 5% by weight, from about 0.2 to about 4% by weight, from about 0.2 to about 3% by weight, from about 0.2 to about 2% by weight, from about 0.5 to about 5% by weight, from about 0.5 to about 4% by weight, from about 0.5 to about 3% by weight, from about 0.5 to about 2% by weight, from about 0.8 to about 5% by weight, from about 0.8 to about 4% by weight, from about 0.5 to about 3% by weight, from about 0.8 to about 2% by weight of one or more water-soluble solvents, based on the weight total hair styling composition.

[0056] In still other embodiments, the hair shaping composition includes from about 0.1 to about 5% by weight of glycerin, based on the total weight of the hair shaping composition. In other embodiments, the hair shaping composition includes from about 0.1 to about 4 wt%, from about 0.1 to about 3 wt%, from about 0.1 to about 2 wt%, from about 0.2 to about 5 wt%, from about 0.2 to about 4 wt%, from about 0.2 to about 3 wt%, from about 0.2 to about 2 wt%, from about 0.5 to about 5 wt%, from about 0.5 to about 4 wt%, from about 0.5 to about 3 wt%, from about 0.5 to about 2 wt%, from about 0.8 to about 5 wt%, from about 0.8 to about 4 wt%, from about 0.5 to about 3 wt%, from about 0.8 to about 2 wt% of glycerin, relative to the total weight of the hair styling composition. has. Cationic guar derivatives#

[0057] Cationic guar derivatives include cationically substituted galactomannan gum (guar) derivatives. The guar molecule itself is a straight-chain mannan branched at regular intervals with single-membered galactose units on alternating mannose units. The mannose units are linked together by means of [3(1-4) glycosidic linkages. The branching of the galactose is by means of an α(1-6) linkage. Cationic derivatives of guar gums are obtained by reaction between the hydroxyl groups of the polygalactomannan and reactive quaternary ammonium compounds. The degree of substitution of the cationic groups on the guar structure must be sufficient to provide a desired cationic charge density. Quaternary ammonium compounds suitable for use in the formation of cationic guar polymers include those conforming to the general formula (XII): R 1 (XII) Z”

[0058]

[0059]

[0060]

[0061]

[0062] in which R1, R2 and R3 are methyl or ethyl groups; R4 is either an epoxyalkyl group of the general formula (XIII): (XIII) or R4 is a halohydrin group of the general formula (XIV): X-CH2-CH-R5— <xiv>< / xiv> OH in which R5 is C1-C3 alkylene; X is chlorine or bromine and Z is an anion such as Cl-, Br-, I- or HSO4-. Cationic guar polymers (cationic derivatives of guar gum) formed from the reagents described above are represented by the general formula (XV): Q1 (XV)

[0063] wherein R is guar gum. Preferably, the cationic guar polymer is guar hydroxypropyltrimethylammonium chloride, which may be more specifically represented by the general formula (XVI): OH

[0064] Suitable cationic guar derivatives have cationic charge densities of at least about 1.25 meq / gm, preferably at least about 1.5 meq / gm, more preferably at least about 1.7 meq / gm, even more preferably at least about 1.8 meq / gm, even more preferably at least about 2.0 meq / gm, and even more preferably at least about 2.3 meq / gm, but preferably also less than about 7 meq / gm, more preferably less than about 5 meq / gm, even more preferably less than about 4.5 meq / gm. The "cationic charge density" of a cationic guar derivative, as that term is used herein, refers to the ratio of the number of positive charges on a monomeric unit of which the polymer is composed to the molecular weight of said monomeric unit. The cationic charge density multiplied by the molecular weight of the polymer determines the number of positively charged sites on a given polymer chain.

[0065] Any anionic counterions may be used in combination with the cationic guars so long as the cationic guars remain soluble in water, in the hair styling composition, or in a coacervate phase of the hair styling composition, and so long as the counterions are physically and chemically compatible with the essential components of the hair styling composition or do not otherwise unduly impair the performance, stability, or aesthetics of the product. Non-limiting examples of such counterions include: halides (e.g., chloride, fluoride, bromide, iodide), sulfate, methyl sulfate, and mixtures thereof.

[0066] Non-limiting examples of cationic guar derivatives include cationic hydroxyethyl guar, cationic hydroxypropyl guar, cationic hydroxybutyl guar, cationic carboxymethyl guar, cationic carboxylpropyl guar, cationic carboxybutyl guar, carboxymethylhydroxypropyl guar, hydroxypropyltrimonium guar chloride, and hydroxypropyltrimonium hydroxypropyl guar chloride.

[0067] The amount of cationic guar derivative in the hair styling compositions will vary. However, in various embodiments, the hair styling composition includes from about 0.1 to about 8% by weight of cationic guar derivative based on the total weight of the hair styling composition.In other embodiments, the hair shaping composition comprises from about 0.1 to about 5 wt%, from about 0.1 to about 4 wt%, from about 0.1 to about 3 wt%, from about 0.1 to about 2 wt%, from about 0.2 to about 5 wt%, from about 0.2 to about 4 wt%, from about 0.2 to about 3 wt%, from about 0.2 to about 2 wt%, from about 0.5 to about 5 wt%, from about 0.5 to about 4 wt%, from about 0.5 to about 3 wt%, from about 0.5 to about 2 wt%, from about 0.8 to about 5 wt%, from about 0.8 to about 4 wt%, from about 0.5 to about 3 wt%, from about 0.8 to about 2% by weight of the cationic guar derivative, based on the total weight of the hair styling composition. has. Water#

[0068] The total amount of water in the hair shaping compositions will vary. However, in various embodiments, the hair shaping compositions include about 70 to about 96% by weight of water, based on the total weight of the compositions. In other embodiments, the hair shaping composition comprises about 75 to about 96% by weight, about 80 to about 96% by weight, about 85 to about 96% by weight, about 90 to about 96% by weight, about 70 to about 95% by weight, about 75 to about 95% by weight, about 80 to about 95% by weight, about 85 to about 95% by weight, about 90 to about 95% by weight, based on the total weight of the hair shaping composition. Various ingredients

[0069] The compositions optionally include or exclude (or are substantially free of) one or more miscellaneous ingredients. Miscellaneous ingredients are ingredients that are compatible with the compositions and do not disrupt or materially affect the fundamental and novel properties of the compositions. Non-limiting examples of ingredients include preservatives, fragrances, pH adjusters, salts, chelating agents, buffers, antioxidants, flavonoids, vitamins, botanical extracts, UV filtering agents, proteins, protein hydrolysates and / or isolates, fillers (e.g., organic and / or inorganic fillers such as talc, calcium carbonate, silica, etc.), composition colorants, etc. In various embodiments, the miscellaneous ingredients are selected from preservatives, fragrances, pH adjusters, salts, chelating agents, buffers, composition colorants, and mixtures thereof.In the context of this disclosure, a "composition colorant" is a compound that colors the composition but does not have an appreciable coloring effect on the hair. In other words, the composition colorant is included to impart coloring to the composition for aesthetic purposes but is not intended to impart coloring properties to the hair. Hair styling gels, for example, may come in a variety of different colors (e.g., light blue, light pink, etc.), but application of the styling gel to the hair does not visibly change the color of the hair.

[0070] The total amount of the one or more miscellaneous ingredients in the compositions, if any, will vary. However, in various embodiments, the compositions include about 0.1 to about 15% by weight of the one or more miscellaneous ingredients, based on the total weight of the compositions. In other embodiments, the compositions include about 0.1 to about 12% by weight, about 0.1 to about 10% by weight, about 0.1 to about 5% by weight, about 0.5 to about 15% by weight, about 0.5 to about 12% by weight, about 0.5 to about 10% by weight, about 0.5 to about 8% by weight, about 0.5 to about 5% by weight, about 1 to about 15% by weight, about 1 to about 12% by weight, about 1 to about 10% by weight, about 1 to about 8% by weight, about 1 to about 5% by weight, about 2 to about 15% by weight, about 2 to about 12% by weight, about 2 to about 10% by weight, about 2 to about 8% by weight, or about 2 to about 5% by weight, based on the total weight of the compositions. PH

[0071] The pH of the composition will vary. However, the compositions typically have a pH of less than 7 (an acidic pH). In other embodiments, the pH may be from about 2.5 to about 6.5, from about 2.5 to about 6, from about 2.5 to about 5.5, from about 2.5 to about 5, from about 2.5 to about 4.5, from about 2.5 to about 4, from about 3 to about 6.5, from about 3 to about 6, from about 3 to about 5.5, from about 3 to about 5, from about 3 to about 4.5, or from about 3 to about 4. Methods

[0072] As explained throughout the present disclosure, the hair shaping compositions are particularly useful in methods of shaping hair, preferably human hair, particularly human head hair. Treatment with the compositions improves fiber alignment, reduces frizz, and imparts a smooth texture to the hair. The methods typically include applying a hair shaping composition of the present disclosure to the hair. The hair is preferably wet or damp, but the composition can also be applied to dry hair. Applying the compositions to the hair will moisten the hair because the compositions are aqueous (containing a large portion of water).

[0073] The hair shaping composition is distributed throughout the hair, preferably distributed substantially evenly throughout the hair, as a leave-in product, i.e., the hair shaping composition is generally not rinsed from the hair prior to shaping and / or drying the hair. The hair to which the hair shaping composition is applied may be physically smoothed or physically manipulated with a shaping action. For example, a comb or brush may be used to incorporate the hair shaping composition into the hair while simultaneously shaping the hair, i.e., pulling the hair in a manner that smooths the hair.Similarly, hair can be physically manipulated with the hands to spread the hair shaping composition through the hair and the hands can also be used to pull or lay the hair flat to smooth the hair.

[0074] While the hair is being brushed or physically manipulated with a styling action, the hair may dry naturally under ambient conditions. Alternatively, a hair dryer may be used to accelerate the drying of the hair. For example, the hair may be combed or brushed while being blow-dried to simultaneously straighten and dry the hair. The hair dryer may provide heat to the hair and accelerate the styling and drying process. In various embodiments, the hair is heated to a temperature of about 120°C to about 250°C, preferably 140°C to about 250°C, more preferably about 150°C to about 200°C. In various embodiments, once the hair is dry or nearly dry, the hair may be treated with a thermal treatment (heat-treated).For example, the hair may be treated with a hot iron, particularly a flat iron. Typically, the hot iron is passed over the hair at least once, at least twice, at least three times, or more. The hot iron is preferably at a temperature of about 120°C to about 250°C, preferably 140°C to about 250°C, more preferably about 150°C to about 200°C.

[0075] In various embodiments, the method includes a dwell time between applying the hair shaping composition to the hair and a heat treatment. The dwell time begins immediately after applying the hair shaping composition to the hair, while the hair is still damp. The hair may dry naturally during the dwell time, the hair may also be subjected to a drying process to accelerate the drying of the hair, for example, the hair may be dried with a hair dryer, provided that the hair dryer does not heat the hair according to a subsequent heat treatment (heat treatment). After a dwell time, a heat treatment (heat treatment) is applied to the hair.For example, the heat treatment preferably heats the hair to a temperature of about 120°C to about 250°C, preferably 140°C to about 250°C, more preferably about 150°C to about 200°C. A hair dryer may provide the heat treatment provided that the hair dryer heats the hair to the indicated temperatures. In a preferred embodiment, the hot iron is used for the heat treatment, for example, a curling iron or a flat iron, wherein the hot iron heats the hair to a temperature of about 120°C to about 250°C, preferably 140°C to about 250°C, more preferably about 150°C to about 200°C.

[0076] When a break is taken between the application of the hair styling composition and a heat treatment, the break time will vary but is typically about 1 minute to about 2 hours. In other embodiments, the dwell time is about 1 minute to about 1 hour, about 1 minute to about 30 minutes, about 1 minute to about 20 minutes, about 2 minutes to about 2 hours, about 2 minutes to about 1 hour, about 2 minutes to about 30 minutes, about 2 minutes to about 20 minutes, about 5 minutes to about 2 hours, about 5 minutes to about 1 hour, about 5 minutes to about 30 minutes, about 5 minutes to about 20 minutes, about 15 minutes to about 2 hours, about 15 minutes to about 1 hour, or about 15 minutes to about 30 minutes. Exclusions

[0077] Any components positively presented in the present disclosure may be negatively excluded from the claims, for example, a claimed composition may be "free", "essentially free" (or "substantially free") of one or more components that are positively presented in the present disclosure.

[0078] In various embodiments, the hair styling composition is free or essentially free of anionic surfactants.

[0079] In various embodiments, the hair shaping composition is free or essentially free of polymers, copolymers and crosslinked polymers formed with acrylate or methacrylate monomers, e.g., free or essentially free of polymers and crosslinked polymers of polyacrylic acid and polyacrylate.

[0080] In various embodiments, the hair styling composition is free or essentially free of N-alkyl-2-mercaptoacetamide. In other embodiments, the hair styling composition is free or essentially free of any mercaptoacetamide.

[0081] In various embodiments, the hair shaping composition is free or essentially free of ethylene carbonate. In other embodiments, the hair shaping composition is free or essentially free of linear carbonates, e.g., dimethyl carbonate, diethyl carbonate, etc. In various embodiments, the composition is free or essentially free of cyclic lactones (e.g., valerolactone, caprolactone, pantolactone, meadowlactone, etc.), free or essentially free of heterocyclic molecules (e.g., 2-oxazolidinone, 2-imidazolidinone, etc.), free or essentially free of sulfones (dimethylsulfone, 2,3,4,5-tetrahydrothiophene-1,1-dioxide), and / or free or essentially free of ureas (e.g., urea, ethylene urea, etc.). In still further embodiments, the hair shaping composition is free or essentially free of carbonates. For example, the hair styling composition may be free or essentially free of cyclic carbonates, preferably cyclic carbonates selected from propylene carbonate, dipropylene carbonate, butylene carbonate, 2,3-butylene carbonate, 2,3-pentylene carbonate, pentylene carbonate, ethylene carbonate, glycerol carbonate or a mixture thereof.

[0082] In various embodiments, the hair styling compositions are free or essentially free of polysaccharides other than cyclodextrin and its derivatives and cationic guar derivatives.

[0083] In various embodiments, the hair styling composition is free or essentially free of silicones, including aminofunctionalized silicones such as amodimethicone.

[0084] In other embodiments, the hair styling composition is free or essentially free of monosaccharides and disaccharides. For example, the composition is free or essentially free of ribose, arabinose, glucose, fructose, xylose, sucrose and / or methyl glucoside.

[0085] In various embodiments, the hair styling composition is free or essentially free of formaldehyde, formaldehyde derivatives, formalin, and compounds that produce formaldehyde when heated.

[0086] In other embodiments, the hair styling composition is free or essentially free of thioglycolic acid, thiolactic acid, or salts thereof. Methods of implementation

[0087] In various embodiments, the hair shaping composition comprises or consists of: a. about 1 to about 8% by weight, preferably about 1 to about 6% by weight, more preferably about 2 to about 5% by weight of citric acid, a salt thereof, or a combination thereof; b. about 0.5 to about 5% by weight, preferably about 1 to about 5% by weight, more preferably about 1 to about 3% by weight of one or more cyclodextrins, their derivatives, or a combination thereof;

[0088] wherein a combined total amount of citric acid, a salt thereof, or a combination thereof of (a) and the one or more cyclodextrins, derivatives thereof, or a combination thereof of (b) is from about 2 to about 12% by weight, preferably from about 2 to about 8, more preferably from about 3 to about 6% by weight; and

[0089] wherein preferably (a) and (b) are individually combined with each other to form a composition wherein (b) is dissolved in (a) before being subsequently combined with additional components of the hair treatment composition; a. from about 0.1 to about 5% by weight, preferably from about 0.1 to about 3% by weight, more preferably from about 0.5 to about 2% by weight of one or more water-soluble solvents, wherein preferably the one or more water-soluble solvents are selected from C2-C6 monohydric alcohols (e.g., ethanol, isopropyl alcohol, etc.), polyols (polyhydric alcohols, such as glycerin), glycols (e.g., ethylene glycol, propylene glycol, butylene glycol, pentylene glycol, caprylyl glycol, etc.), and mixtures thereof, wherein, more preferably, at least one of the one or more water-soluble solvents is glycerin; b. about 0.1 to about 8% by weight, preferably about 0.2 to about 5% by weight, more preferably about 0.5 to about 4% by weight of one or more cationic guar derivatives, wherein the one or more cationic guar derivatives are preferably selected from cationic guar derivatives, hydroxyethyl guar, cationic hydroxypropyl guar, cationic hydroxybutyl guar, cationic carboxymethyl guar, cationic carboxypropyl guar, cationic carboxybutyl guar, carboxymethylhydroxypropyl guar, guar hydroxypropyltrimonium chloride and hydroxypropyl guar hydroxypropyltrimonium chloride, preferably wherein the one or more cationic guar derivatives are guar hydroxypropyltrimonium chloride and hydroxypropyl guar hydroxypropyltrimonium chloride or a mixture thereof; c. from about 70 to about 96% by weight, preferably from about 80 to about 95% by weight, more preferably from about 85 to about 95% by weight of water;

[0090] wherein all weight percentages are based on a total weight of the composition. a. optionally, about 0.1 to about 15% by weight, preferably about 0.5 to about 10% by weight, more preferably about 0.5 to about 5% by weight of one or more water-soluble solvents, preferably wherein the one or more water-soluble solvents are selected from C2-C6 monoalcohols, polyols (polyhydric alcohols), glycols or a mixture thereof; b. optionally, from about 0.01 to about 10% by weight, preferably from about 0.1 to about 8% by weight, more preferably from about 1 to about 5% by weight of one or more miscellaneous ingredients, preferably one or more miscellaneous ingredients selected from preservatives, fragrances, pH adjusters, salts, chelating agents, buffers, antioxidants, flavonoids, vitamins, amino acids (e.g., taurine), botanical extracts, UV filtering agents, proteins, protein hydrolysates and / or isolates, fillers (e.g., organic and / or inorganic fillers such as talc, calcium carbonate, silica, particular materials, etc.), emollients, composition colorants, or a mixture thereof;

[0091] wherein all weight percentages are based on a total weight of the composition.

[0092] The pH of the composition may vary. However, in various embodiments, a pH of less than 7 (an acidic pH) is desirable. For example, the pH may be from about 3 to about 6.5, from about 3 to about 6, from about 3 to about 5.5, from about 3 to about 5, from about 3 to about 4.5, from about 3.5 to about 6.5, from about 3.5 to about 6, from about 3.5 to about 5.5, from about 3.5 to about 5, or from about 3.5 to about 4.5.

[0093] In various embodiments, the hair shaping composition comprises, consists essentially of, or consists of: a. about 1 to about 8% by weight, preferably about 1 to about 6% by weight, more preferably about 2 to about 5% by weight of citric acid, a salt thereof, or a combination thereof; b. about 0.5 to about 5% by weight, preferably about 1 to about 5% by weight, more preferably about 1 to about 3% by weight of one or more cyclodextrins, their derivatives, or a combination thereof;

[0094] wherein a combined total amount of the citric acid, a salt thereof, or a combination thereof of (a) and the one or more cyclodextrins, derivatives thereof, or a combination thereof of (b) is from about 2 to about 12% by weight, preferably from about 2 to about 8, more preferably from about 3 to about 6% by weight;

[0095] wherein preferably (a) and (b) are individually combined with each other to form a composition wherein (b) is dissolved in (a) before being subsequently combined with additional components of the hair treatment composition; a. from about 0.1 to about 5% by weight, preferably from about 0.1 to about 3% by weight, more preferably from about 0.5 to about 2% by weight of one or more water-soluble solvents, wherein preferably the one or more water-soluble solvents are selected from C2-C6 monohydric alcohols (e.g., ethanol, isopropyl alcohol, etc.), polyols (polyhydric alcohols, such as glycerin), glycols (e.g., ethylene glycol, propylene glycol, butylene glycol, pentylene glycol, caprylyl glycol, etc.), and mixtures thereof, wherein, more preferably, at least one of the one or more water-soluble solvents is glycerin; b. from about 0.1 to about 8% by weight, preferably from about 0.2 to about 5% by weight, more preferably from about 0.5 to about 4% by weight of guar hydroxypropyltrimonium chloride, hydroxypropyl guar hydroxypropyltrimonium chloride, or a mixture thereof; c. from about 70 to about 96% by weight, preferably from about 80 to about 95% by weight, more preferably from about 85 to about 95% by weight of water;

[0096] wherein all weight percentages are based on a total weight of the composition. a. optionally, from about 0.1 to about 15% by weight, preferably from about 0.5 to about 10% by weight, more preferably from about 0.5 to about 5% by weight of one or more water-soluble solvents, preferably wherein the one or more water-soluble solvents are selected from C2-C6 monoalcohols, polyols (polyhydric alcohols), glycols or a mixture thereof; and b. optionally, from about 0.01 to about 10% by weight, preferably from about 0.1 to about 8% by weight, more preferably from about 1 to about 5% by weight of one or more miscellaneous ingredients, preferably one or more miscellaneous ingredients selected from preservatives, fragrances, pH adjusters, salts, chelating agents, buffers, antioxidants, flavonoids, vitamins, amino acids (e.g., taurine), botanical extracts, UV filtering agents, proteins, protein hydrolysates and / or isolates, fillers (e.g., organic and / or inorganic fillers such as talc, calcium carbonate, silica, particular materials, etc.), emollients, composition colorants, or a mixture thereof;

[0097] wherein all weight percentages are based on a total weight of the composition.

[0098] The pH of the composition may vary. However, in various embodiments, a pH of less than 7 (an acidic pH) is desirable. For example, the pH may be from about 3 to about 6.5, from about 3 to about 6, from about 3 to about 5.5, from about 3 to about 5, from about 3 to about 4.5, from about 3 to about 4, from about 3.5 to about 6.5, from about 3.5 to about 6, from about 3.5 to about 5.5, from about 3.5 to about 5, or from about 3.5 to about 4.5. EXAMPLES

[0099] An implementation of the present disclosure is provided by means of the following examples. These examples serve to illustrate the technology without being limiting in nature. Example 1 (Compositions)

[0100] [Tableauxl] Inventive Comparative ABCDE (a) Citric acid 2.5 2.5 2.5 2.5 2.5 (b) Cyclodextrin 1.5 1.5 1.5 1.5 1.5 Total (a)+(b) 4 4 4 4 4 Weight ratio 1.7:1 1.7:1 1.7:1 1.7:1 1.7:1 Molecular ratio 10:1 10:1 10:1 10:1 10:1 (c) Glycerin 1 1 1 1 (d) Hydroxypropyl guar hydroxypropyltriammonium chloride 1 1 Guar gum 1 Carrageenan 1 Miscellaneous * < 5 <5 <5 <5 <5 (e) Water 94 95 95 94 94 PH 3 to 4 3 to 4 3 to 4 3 to 4

[0101] * Fillers, pH adjusters, preservatives, botanical extracts, perfumes, buffers, stabilizers, vitamins and / or emollients, etc., e.g. henoxyethanol, sodium hydroxide and acetic acid. Example 2 (Heatless curling performance)

[0102] Strands of straight Caucasian hair were obtained and cleaned with a standard shampoo. After rinsing the shampoo from the hair strands, 0.15 grams (per gram of hair) of inventive composition A or comparative composition BE a were applied to the damp or wet hair strands and the composition was massaged into the hair for approximately 1 minute. The hair in each hair strand was then wound onto a curler. As a control, one strand of hair was washed with the standard shampoo and wound onto a curler. The hair was left to dry on the curlers overnight. The following day, the hair strands were removed from the curlers and placed in a humidity chamber at 23°C and 80% relative humidity and the curl hold and curl length were evaluated at 5 minutes, 30 minutes, 1 hour, 24 hours and 96 hours. The curl hold results are shown in [Fig.l] and the results for curl length are shown in [Fig.2].The data show that in the absence of treatment with inventive composition A, hair shape (i.e., curls) is not maintained. Hair treated with the inventive composition showed a statistically significant improvement in both curl hold and curl length (p < 0.001), as determined by Sigma® Plot 12.0 software using a one-way ANOVA method for all time periods compared to the control and all comparative compositions.

[0103] [Tables2] Curl Hold Statistically significant (p < 0.001) Sigma® Plot 12.0 software using one-way ANOVA 5 min 30 min 1 hour 24 hours 96 hours Control Yes Yes Yes Yes Yes Comparative B Yes Yes Yes Yes Yes Comparative C Yes Yes Yes Yes Yes Comparative D Yes Yes Yes Yes Yes Comparative E Yes Yes Yes Yes Yes

[0104] [Tables3] Loop Length Statistically significant (p < 0.001) Sigma® Plot 12.0 software using one-way ANOVA 5 min 30 min 1 hour 24 hours 96 hours Control Yes Yes Yes Yes Yes Comparative B Yes Yes Yes Yes Yes Comparative C Yes Yes Yes Yes Yes Comparison D Yes Yes Yes Yes Yes Comparison E Yes Yes Yes Yes Yes Example 3 (Curling performance with heat)

[0105] Strands of straight Caucasian hair were obtained and cleaned with a standard shampoo. After rinsing the shampoo from the strands of hair, 0.15 grams (per gram of hair) of inventive composition A or comparative composition BE a were applied to the damp or wet strands of hair and the composition was massaged into the hair for about 1 minute. As a control, one strand of hair was cleaned with the standard shampoo. The strands of hair were then blow-dried for about 2 minutes, until dry. A curling iron was used to curl the dry strands of hair. The hair was wrapped around the curling iron set at a temperature of 180°C for about 20 seconds.After curling, the hair strands were placed in a humidity chamber at 23°C and 80% relative humidity and the curl hold and curl length were assessed at 5 minutes, 30 minutes, 1 hour, 24 hours and 96 hours. The curl hold results are shown in [Fig. 3] and the results for curl length are shown in [Fig. 4]. The data show that in the absence of treatment with inventive composition A, the hair shape (i.e., curls) is not maintained. Hair treated with the inventive composition showed a statistically significant improvement in both curl hold and curl length (p < 0.001) at different time points, as determined by Sigma® Plot 12.0 software using a one-way ANOVA method compared to the control and all comparative compositions.

[0106] [Tables4] Curl Hold Statistically significant (p < 0.001) Sigma® Plot 12.0 software using one-way ANOVA 5 min 30 min 1 hour 24 hours 96 hours Control No No Yes Yes Yes Comparative B No Yes Yes No No Comparative C No No Yes No No Comparative D Yes No Yes No No Comparative E No No Yes No No

[0107] [Tables5] Loop Length Statistically significant (p < 0.001) Sigma® Plot 12.0 software using one-way ANOVA 5 min 30 min 1 hour 24 hours 96 hours Control No Yes Yes Yes Yes Comparative B Yes Yes Yes Yes Yes Comparative C Yes Yes Yes No No Comparative D Yes Yes Yes Yes Yes Comparative E No Yes Yes No No Example 3 (Washing study)

[0108] Strands of straight Caucasian hair (n = 6) were obtained and cleaned with a standard shampoo. After rinsing the shampoo from the strands of hair, 0.15 grams (per gram of hair) of the inventive composition A was applied to the damp or wet strands of hair and the composition was massaged into the hair for approximately 1 minute. The hair from each strand of hair was then wound onto a curler. As a control, one strand of hair was washed with the standard shampoo and wound onto a curler. The strands of hair were allowed to dry on the curlers overnight. The next day, the hair was removed from the curlers, washed with a standard shampoo and placed in a humid chamber at 23°C and 80% relative humidity for 24 hours.After 24 hours in the humidity chamber, the hair strands were tested using a Bass Nova Vision Rumba device to determine frizz volume, curl definition, and curliness. The Rumba device was specifically designed to measure hair fiber orientation and calculate straightness and alignment coefficients. It is commonly used in the cosmetics industry. It is useful for all hair types. The results are shown in the table below.

[0109] [Tableauxô] Inventive Witness Frizz volume *70.5 cm2 101.9 cm2 Curl definition *45.2 on average Alignment coefficient (l / °) 32.1 (l / °) Wave *16.2° 13.5°

[0110] * Statistically significant (p < 0.05)

[0111] The data shows that the hair strands treated with the composition inventive A exhibited significantly less frizz, had better curl definition, and retained more curl. Results for all three measurements were statistically significant (p < 0.05), as determined by Sigma® Plot 12.0 software using one-way ANOVA analysis.

[0112] Salts referred to throughout the disclosure may include salts having a counterion such as an alkali metal, alkaline earth metal, or ammonium counterion. This list of counterions, however, is not limiting. Suitable counterions for the components described herein are known in the art.

[0113] The expression “one or more” means “at least one” and therefore includes individual components as well as mixtures / combinations.

[0114] The term “plurality” means “more than one” or “two or more”.

[0115] Except in operational examples, or unless otherwise indicated, all numbers expressing quantities of ingredients and / or reaction conditions may be modified in all cases by the term "approximately", meaning to within + / - 5% of the number indicated.

[0116] All percentages, parts and ratios herein are based on the total weight of the compositions of the present invention, unless otherwise indicated.

[0117] Some of the various categories of components identified may overlap. In such cases where an overlap may exist and the composition includes both components (or the composition includes more than two overlapping components), an overlapping compound does not represent more than one component. For example, some compounds may be considered both a nonionic surfactant or emulsifier and a fat component. If a particular composition includes both a nonionic surfactant or emulsifier and a fat compound, a single compound will serve solely as the nonionic surfactant or emulsifier or solely as the fat component (the single compound does not serve as both a nonionic surfactant or emulsifier and a fat component).

[0118] A "rinse-out" product refers to a composition that is rinsed and / or washed from the hair with water after or during application of the composition to the hair, and before drying and / or styling the hair. At least a portion of the composition is removed from the hair during rinsing and / or washing.

[0119] A "leave-in" product refers to a composition that is not rinsed and / or washed out of the hair after or during application of the composition to the hair. The composition remains on the hair during drying and / or throughout styling.

[0120] As used herein, all ranges provided are intended to include each specific range within the given ranges, as well as a combination of intermediate sub-ranges. Thus, a range of 1 to 5 specifically includes 1, 2, 3, 4, and 5, as well than subranges such as 2 to 5, 3 to 5, 2 to 3, 2 to 4, 1 to 4, etc. All ranges and values ​​disclosed herein are inclusive and combinable. For example, any value or point described herein that falls within a range described herein may serve as a minimum or maximum value to derive a subrange, etc.

[0121] The composition of the present case optionally includes one or more surfactants and / or emulsifiers, for example, one or more nonionic, anionic, cationic, and / or amphoteric / zwitterionic surfactants. The terms "surfactants" and "emulsifiers" include salts of the surfactants and emulsifiers even if not explicitly stated. In other words, whenever the disclosure refers to a surfactant or emulsifier, it is intended that salts are also encompassed to the extent that such salts exist, even though the specification may not specifically refer to a salt (or may not refer to a salt in all instances throughout the disclosure), for example, by using language such as "a salt thereof" or "salts thereof." Sodium and potassium are common cations that form salts with surfactants and emulsifiers.However, additional cations such as ammonium ions, or alkanolammonium ions such as monoethanolammonium or triethanolammonium ions, can also form surfactant salts.

[0122] The term "substantially free" or "essentially free" as used herein means that less than about 2% by weight of a specific material is added to a composition, based on the total weight of the compositions. However, the compositions may include less than about 1% by weight, less than about 0.5% by weight, less than about 0.1% by weight, or none of the specified material.

[0123] Any components positively presented in the present disclosure may be negatively excluded from the claims, for example, a claimed composition may be "free", "essentially free" (or "substantially free") of one or more components that are positively presented in the present disclosure.

Claims

Claims

1. A method of shaping hair comprising: (i) applying a hair shaping composition to the hair; (ii) physically manipulating the hair to which the hair shaping composition is applied into a desired shape and (iii) without rinsing the hair shaping composition, drying the hair; wherein the hair shaping composition comprises: (a) about 1 to about 8% by weight of citric acid, a salt thereof, or a combination thereof; (b) about 0.5 to about 5% by weight of one or more cyclodextrins, derivatives thereof, or a combination thereof; wherein a combined total amount of (a) and (b) is about 2 to about 12% by weight; (c) about 0.1 to about 5% by weight of one or more water-soluble solvents; (d) about 0.1 to about 8 weight percent of one or more cationic guar derivatives; and (e) about 70 to about 96 weight percent of water;wherein all weight percentages are based on a total weight of the composition.;

2. The method of claim 1, wherein the hair styling composition has a pH of about 3 to about 6; and / or wherein (a) and (b) are in a weight ratio of about 4:1 to about 1:1 ((a):(b)) and / or a molar ratio of about 20:1 to about 5:1 ((a):(b)).

3. A method according to claims 1 or 2, wherein (a) and (b) are individually combined with each other to form a mixture in which (b) is dissolved in (a); and the mixture is then combined with additional components of the composition.

4. A method according to any one of the preceding claims wherein the one or more cyclodextrins, their derivatives, or a mixture thereof, are selected from α-cyclodextrin, β-cyclodextrin, γ-cyclodextrin, methyl-α-cyclodextrin, methyl-β-cyclodextrin, methyl-γ-cyclodextrin, or mixtures thereof, preferably wherein the one or more cyclodextrins, their derivatives, or one of their mixtures are chosen from B-cyclodextrin, its derivatives, or their mixtures.

5. A method according to any preceding claim, wherein the hair shaping composition further comprises: (f) about 0.1 to about 10% by weight of one or more miscellaneous ingredients, preferably wherein the one or more miscellaneous ingredients are selected from preservatives, fragrances, pH adjusters, salts, chelating agents, buffers, antioxidants, flavonoids, vitamins, amino acids, botanical extracts, UV filtering agents, peptides, proteins, protein hydrolysates and / or isolates, fillers (e.g., organic and / or inorganic fillers such as talc, calcium carbonate, silica, special materials, etc.), emollients, composition colorants, or mixtures thereof.

6. A method according to any preceding claim, wherein the hair-styling composition comprises: (a) about 1 to about 5% by weight of citric acid, a salt thereof, or a combination thereof; (b) about 1 to about 5% by weight of one or more cyclodextrins, derivatives thereof, or a combination thereof, preferably wherein the one or more cyclodextrins, derivatives thereof, or mixtures thereof, are selected from β-cyclodextrin, derivatives thereof, or mixtures thereof; wherein a combined total amount of (a) and (b) is about 2 to about 8% by weight; (c) about 0.5 to about 4% by weight of one or more water-soluble solvents; (d) about 0.5 to about 5% by weight of hydroxypropyl guar hydroxypropyltrimonium chloride; (e) about 70 to about 96% by weight of water; (f) optionally, about 0.1 to about 10% by weight of one or more miscellaneous ingredients;wherein the composition has a pH of about 3 to about 5, (a) and (b) are in a weight ratio of about 4:1 to about 1:1 ((a):(b)) and / or a molar ratio of about 20:1 to about 5:1; and all weight percentages are based on a total weight of the composition.;

7. A method according to any preceding claim, wherein (a) and (b) are individually combined together to form a mixture in which the cyclodextrin is dissolved in citric acid; and the mixture is then combined with additional components of the composition.

8. A method according to any preceding claim, wherein the hair is physically manipulated into curls.

9. A method according to any preceding claim further comprising heating the hair to which the hair styling composition is applied, to a temperature of about 140°C to about 220°C, wherein the heating is optionally preceded by a leave-on time of about 1 minute to about 1 hour.

10. A method according to any preceding claim, comprising drying the hair with a hair dryer and then shaping the hair with a hot iron at a temperature of about 140°C to about 220°C.