Method and formulation for curling hair

Abstract

Disclosed herein are methods and formulations for curling hair, particularly methods, formulations, and kits for curling and / or preventing damage in hair curling. Hair can be curled by treating with a hydroxide-containing agent in combination with one or more active agents, without the need for a thiol group or peroxide-based agent. The active agents can be applied simultaneously with the hydroxide-containing agent to impart curl to the hair. They can be applied as a combined formulation or simultaneously as separate formulations. The active agents and the hydroxide-containing agent can be used together to control the level of curl imparted to the hair as compared to the amount of natural curl, if any, in untreated hair.

Description

Cross-references to related applications

[0001] This application claims priority to U.S. Application No. 15 / 282,795, filed September 30, 2016, which claims priority to U.S. Provisional Application Serial No. 62 / 361,366, filed July 12, 2016, and U.S. Provisional Application Serial No. 62 / 380,020, filed August 26, 2016, the disclosure of which is incorporated herein by reference in its entirety. Technical Field

[0002] This invention generally relates to formulations and methods for curling hair, and particularly for imparting and controlling the level of curl in hair. Background Technology

[0003] Hair is composed of many long, parallel chains of amino acids. These amino acid chains or polymers are linked together by 1) hydrogen bonds, 2) salt bridges between acid and base groups, and 3) disulfide bonds.

[0004] At alkaline pH levels, disulfide bonds in hair can be broken (Dombrink et al., *ChemMatters*, 1983, p. 8). For example, alkaline straighteners contain hydroxide ions that attack disulfide bonds. The breaking of disulfide bonds using alkaline straighteners achieves hair straightening by altering the relative positions of polypeptide chains. The straightening process is accomplished by rinsing the hair and / or applying a neutralizing agent.

[0005] While alkaline straighteners and other alkaline straighteners are very effective at straightening and straightening hair, they can lead to reduced hair strength and potential hair loss due to breakage.

[0006] In addition, it is well known that alkaline straighteners and alkaline hair straighteners cannot be used for perming.

[0007] Traditional perming involves using a thiol-based reducing agent, followed by a second oxidation step using hydrogen peroxide to set the hair. These thiol-based reducing agents have an unpleasant odor, and if not properly rinsed between steps, they can cause hair breakage.

[0008] Therefore, there is a need for hair curling formulations and treatments that can provide improved conditioning effects to hair when it is curled. Specifically, there is a need to provide curled hair with a lasting feeling of moisture, smoothness, and manageability control.

[0009] Hair curling agents and treatments that can adjust or select the level of curl imparted to the hair are also needed.

[0010] There is also a need for hair curling agents and treatments that can be applied to the hair as a single formulation.

[0011] Additionally, hair curling agents without foul-smelling thiols or related odors are required.

[0012] Therefore, one object of the present invention is to provide a curling preparation and a curling method for repairing and / or enhancing the improvement of curly hair.

[0013] Another object of the present invention is to provide a curling formulation and method that can be used to adjust or select the level of curl imparted to hair.

[0014] Another object of the present invention is to provide a hair curling formulation and treatment agent that can be applied to hair as a single formulation, and a formulation without a foul thiol odor. Summary of the Invention

[0015] Formulations, kits, and methods for curling hair are described, comprising using a hydroxide-containing reagent or a formulation thereof in combination with an active agent or a formulation thereof. The formulations, kits, and methods can also be used to control the level of curl imparted to the hair during the curling process. In some embodiments, the formulation for curling hair can be applied once or multiple times after the hair curling treatment to alter the level of curl in the hair.

[0016] The methods described herein comprise steps for hair reshaping before, during, or after applying any formulation containing one or more surfactants and / or one or more hydroxide-containing reagents.

[0017] This article describes surfactant formulations containing one or more compounds that interact with keratin through one or more binding events (e.g., absorption, binding, etc.) and may also react with one or more nucleophiles (e.g., thiols) in hair. As used herein, “binding” refers to the formation of covalent, ionic, or hydrogen bonds. Surfactant formulations may also provide improved conditioning and provide a lasting feeling of moisture and smoothness without making hair greasy, improve appearance (e.g., shine), increase dry strength (tensile strength), make hair easier to comb when wet or dry, reduce hair breakage, or reduce frizz, or any combination thereof.

[0018] Traditional methods of curling hair do not use alkaline or base-based or hydroxide-containing agents, which are known hair straighteners / curling agents and may cause reduced hair strength and potential hair loss due to breakage. The curling methods disclosed herein are applicable to hair activators combined with hydroxide-containing agents (or formulations thereof). These methods curl hair and repair damage to the curled hair. Furthermore, the curling methods described herein provide improved hair styling methods, for example, during hair curling treatments.

[0019] It is believed that using one or more surfactants can not only control the level of curl imparted to the hair during the hair curling process, but also further prevent damage caused by hydroxide-containing agents applied to the hair.

[0020] During the hair curling process or treatment, a combination formulation containing an active agent and one or more hydroxide-containing agents is applied to the hair. Alternatively, during the hair curling process or treatment, the active agent formulation is applied simultaneously with a formulation containing one or more hydroxide-containing agents. The simultaneous addition of the active agent and the hydroxide-containing agent can be used to adjust or control the level of curl imparted to the hair during the curling process. The level of curl imparted can depend on the amount of active agent used, which can be expressed as the weight ratio of the amount of active agent present in the formulation applied to the hair during the hair curling process to the amount of hydroxide-containing agent present in the formulation applied to the hair. Preferably, the formulations are applied simultaneously; optionally, they are mixed just before application to form a combination formulation. Alternatively, the active agent and the hydroxide-containing agent can be provided as a single, premixed combination formulation.

[0021] The pH of the combination formulation is preferably at least about 9.5, more preferably at least about 10.5. In some embodiments, the pH of the combination formulation is about 11 or higher. In some embodiments, the pH of the combination formulation is about 10 or higher. When the formulation is mixed during use, the amount of active agent used is preferably such that it will not lower the pH of the combination formulation to below about 9.5, more preferably not to below about 10.5.

[0022] The weight ratio of the hydroxide-containing reagent formulation to the surfactant formulation can be in the range of about 10:1 to about 1:5; 5:1 to 1:5; 4:1 to 1:4; or 3:1 to 1:3. In some embodiments, the weight ratio of the hydroxide-containing reagent formulation to the surfactant formulation is in the range of about 10:1 to about 1:1; 5:1 to 1:1; 4:1 to 1:1; or 3:1 to 1:1. In some instances, the weight ratio is about 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4 or 1:5 or within about 10% of these ratios, preferably about 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4 or 1:5 or within about 10% of these ratios.

[0023] In some other embodiments, the surfactant formulation may be applied to the hair immediately or shortly thereafter (e.g., within 1-5 minutes) after applying the hydroxide-containing reagent or its formulation.

[0024] The curl imparted to hair following the curling treatment methods defined herein (referred to herein as “imparted curl”) can remain for a period of time without noticeable change or substantially without noticeable change. The treated hair retains its curl when subjected to conditions (e.g., one or more washing cycles) that would not be retained under these conditions without the treatment according to the methods described herein.

[0025] In some embodiments, after about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, 25, 30, 35, 40, 45, or 50 or more cleaning cycles, the percentage reduction in curl is less than about 5%, 10%, 15%, 20%, or 50% of the imparted curl. In some embodiments, after about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, 25, 30, 35, 40, 45, or 50 or more cleaning cycles, the curl remains unchanged or substantially unchanged. Detailed Implementation

[0026] I. Definition The numerical ranges revealed in this paper individually disclose each possible number within that range, as well as any subranges and combinations thereof. For example, the carbon range (i.e., C1-C) 10 The aim is to reveal each possible carbon value individually and / or the subranges included within it. For example, C1-C 10 The carbon length range reveals C1, C2, C3, C4, C5, C6, C7, C8, C9 and C 10 The ranges also reveal subranges encompassed within them, such as C2-C9, C3-C8, C1-C5, etc. Similarly, integer value ranges of 1-10 reveal individual values ​​of 1, 2, 3, 4, 5, 6, 7, 8, and 10, as well as subranges encompassed within them. Furthermore, concentration ranges or weight percentage ranges, such as formulations of 1% to 2% (by weight), reveal individual values ​​and their fractions (e.g., 1%, 1.1%, 1.2%, 1.32%, 1.48%, etc.), as well as subranges encompassed within them.

[0027] The term "hair" refers to one or more individual hairs, as well as the natural components of hair, such as oils from the body. Hair can also refer to virgin hair or processed hair, such as hair that has been exposed to hair curling or straightening agents.

[0028] For example, the “effective amount” of an active agent as described herein refers to the amount of active agent in a formulation that, when applied as part of a desired hair treatment, achieves the desired results, such as the desired level of curl, smoothness, little or no breakage, excellent or good feel, and / or a healthy appearance (by visual inspection).

[0029] "Cosmetic acceptable" means that compounds, materials, and formulations suitable for use in contact with human and animal tissues, within the bounds of reasonable medical judgment, without excessive toxicity, irritation, allergic reactions, or other problems or complications commensurate with a reasonable benefit / risk ratio. More specifically, cosmetic acceptable means materials, compounds, or formulations suitable for contact with skin, scalp, or hair. Cosmetic acceptable materials are known to those skilled in the art.

[0030] As used in this article, "shampoo" generally refers to a liquid or semi-solid preparation applied to the hair that contains detergents or soaps for cleaning the hair.

[0031] As used in this article, "conditioner" generally refers to a preparation (e.g., liquid, cream, lotion, gel, semi-solid) applied to the hair to soften it, make it smooth, and / or change its shine.

[0032] As used in this article, “reshaping” generally refers to deformation, such as mechanical deformation of hair, including but not limited to curling, braiding, and / or twisting. However, hair reshaping is not intended to refer to deformation that results in straightening or straightening of hair.

[0033] The terms "analog" and "derivative" are used interchangeably herein and refer to compounds having the same core as the parent compound but differing from the parent compound in terms of bond order, the absence or presence of one or more atoms and / or groups of atoms, and combinations thereof. A derivative may differ from the parent compound, for example, in the presence of one or more substituents on the core, which may contain one or more atoms, functional groups, or substructures. Generally, it is conceivable that derivatives are formed from the parent compound, at least theoretically, via chemical and / or physical processes.

[0034] The terms “electrophilic group” and “electrophilic group” are used interchangeably and refer to one or more functional groups or portions that have an affinity for or attract electrons.

[0035] As used herein, a “Michael acceptor” is a type of electrophilic group or moiety that participates in a nucleophilic addition reaction. A Michael acceptor can be or may contain an α,β-unsaturated carbonyl group or moiety, such as a ketone. Other Michael acceptors contain π bonds, such as double or triple bonds conjugated with other electron-withdrawing groups containing π bonds, such as nitro, nitrile, and carboxylic acid or aryl groups.

[0036] As used herein, “alkyl” refers to a free radical of a saturated or unsaturated aliphatic group, including straight-chain alkyl, alkenyl, or ynyl groups; branched-chain alkyl, alkenyl, or ynyl groups; cycloalkyl, cycloalkenyl, or cycloynyl (alicyclic) groups; alkyl-substituted cycloalkyl, cycloalkenyl, or cycloynyl groups; and cycloalkyl-substituted alkyl, alkenyl, or ynyl groups. Unless otherwise stated, straight-chain or branched alkyl groups have 30 or fewer carbon atoms in their backbone (e.g., for straight-chain C1-C1 alkyl groups). 30 For C3-C branches 30 More preferably, it has 20 or fewer carbon atoms, even more preferably 12 or fewer carbon atoms, and most preferably 8 or fewer carbon atoms. In some embodiments, the chain has 1-6 carbon atoms. Similarly, preferred cycloalkyl groups have 3-10 carbon atoms in their ring structure, more preferably 5, 6, or 7 carbon atoms in the ring structure. The ranges provided above include all values ​​between the minimum and maximum values.

[0037] The term "alkyl" includes both "unsubstituted alkyl" and "substituted alkyl," the latter referring to an alkyl moiety having one or more substituents that have replaced hydrogen on one or more carbons of a hydrocarbon skeleton. These substituents include, but are not limited to, halogens, hydroxyl groups, carbonyl groups (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), thiocarbonyl groups (e.g., thioesters, thioacetic acids, or thiocarbamates), alkoxy groups, phosphoryl groups, phosphate groups, phosphonates, hypophosphonates, amino groups, amide groups, amidine groups, imine groups, cyano groups, nitro groups, azide groups, hydrogen sulfide groups, alkyl sulfide groups, sulfate groups, sulfonate groups, aminosulfonyl groups, sulfonamide groups, sulfonyl groups, heterocyclic groups, aralkyl groups, or aromatic or heteroaromatic moieties.

[0038] Unless otherwise specified, "lower alkyl" as used herein refers to an alkyl group as defined above, but having one to ten carbon atoms, more preferably one to six carbon atoms, in its skeletal structure. Similarly, "lower alkenyl" and "lower alkynyl" have similar chain lengths. Preferred alkyl groups are lower alkyl groups.

[0039] The alkyl group may also contain one or more heteroatoms within the carbon skeleton. Examples include oxygen, nitrogen, sulfur, and combinations thereof. In some embodiments, the alkyl group contains one to four heteroatoms.

[0040] As used herein, "alkenyl" and "alkynyl" refer to the presence of one or more double or triple bonds of similar length (e.g., C2-C). 30 ) and possible unsaturated aliphatic groups that substitute for the alkyl groups mentioned above.

[0041] As used herein, “aryl” refers to a 5-, 6-, or 7-membered aromatic ring. This ring can be a carbocyclic, heterocyclic, fused carbocyclic, fused heterocyclic, bicyclic, or biheterocyclic system, optionally substituted with an alkyl group as described above. More broadly, as used herein, “Ar” comprises a 5-, 6-, or 7-membered monocyclic aromatic group that may contain zero to four heteroatoms. Examples include, but are not limited to, benzene, pyrrole, furan, thiophene, imidazole, oxazole, thiazole, triazole, pyrazole, pyridine, pyrazine, pyridazine, and pyrimidine. Those aryl groups having heteroatoms in their ring structure may also be referred to as “heteroaryl,” “aryl heterocycle,” or “heteroaromatic compound.” Aromatic rings may be substituted at one or more ring positions with substituents as described above, such as halogens, azides, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, alkoxy, amino, nitro, hydrothioyl, imino, amide, phosphonate, hypophosphonate, carbonyl, carboxyl, silyl, ether, alkylthio, sulfonyl, sulfonamide, ketone, aldehyde, ester, heterocyclic, aromatic or heteroaromatic moiety, -CF3, and -CN. The term "Ar" also includes polycyclic systems having two or more rings, wherein two or more carbons are shared by two adjacent rings (the rings are "fused rings"), wherein at least one ring is an aromatic ring, for example, the other ring may be cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, and / or heterocyclic, or both rings may be aromatic rings.

[0042] As used herein, "alkylaryl" refers to an alkyl group that has been replaced by an aryl group (e.g., an aromatic or heteroaromatic group).

[0043] As used herein, "heterocycle" refers to a cyclic free radical linked by a single or double ring of carbon or nitrogen atoms containing 3-10 ring atoms, preferably 5-6 ring atoms, containing carbon and one to four heteroatoms, each selected from non-peroxide oxygen, sulfur, and N (Y), wherein Y is absent or H, O, (C 1-4 The alkyl, phenyl, or benzyl group, optionally containing one or more double or triple bonds, and optionally substituted with one or more substituents. The term "heterocycle" also encompasses substituted and unsubstituted heteroaryl rings. Examples of heterocycles include, but are not limited to, benzimidazolyl, benzofuranyl, benzothiofuranyl, benzothiophene, benzooxazolyl, benzooxazolinyl, benzothiazolyl, benzotriazolyl, benzotetrazole, benzoisooxazolyl, benzoisothiazolyl, benzimidazolinyl, carbazole, 4aH-carbazole, carbolinyl, benzodihydropyranyl, benzopyranyl, borazolinyl, decahydroquinolinyl, 2 H 6 H-1,5,2-Dithiazinyl, dihydrofurano[2,3-b]tetrahydrofuran, furanyl, furazanyl, imidazoalkyl, imidazolinyl, imidazolyl, 1H-indazoleyl, indolenyl, indololinyl, indolazinyl, indolyl, 3H-indolyl, indigo acyl, isobenzofuranyl, isobenzodihydropyranyl, isoindazoleyl, isoindololinyl, isoindolyl, isoquinolinyl, isothiazolyl, isoxazolyl, methylene Oxadiazolyl, morpholinyl, naphthidyl, octahydroisoquinolinyl, oxadiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-diazolyl, oxazolylalkyl, oxazolyl, hydroxyindolyl, pyrimidinyl, phenanthridine, phenanthrololinyl, phenazinyl, phenothiazinyl, phenothiazinyl, phthalazinyl, piperazinyl, piperidinyl, piperidinoneyl, 4-piperidinoneyl Piperyl, pteridinyl, purinyl, pyranyl, pyrazinyl, pyrazolylylene, pyrazolinyl, pyrazolyl, pyridazinyl, pyridoxazole, pyridinium, pyridinyl, pyrimidinyl, pyrrolidinyl, pyrrolinyl, 2H-pyrrolidinyl, pyrrolidinyl, quinazolinyl, quinolinyl, 4H-quinazinyl, quinoxalinyl, quininecycloyl, tetrahydrofuran The group includes tetrahydroisoquinolinyl, tetrahydroquinolinyl, tetrazolyl, 6H-1,2,5-thiadiazinyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, thianyl, thiazolyl, thienyl, thienothiazolyl, thienooxazolyl, thienoimidazolyl, thiophenyl, and xanthonyl.

[0044] As used herein, “heteroaryl” refers to a monocyclic aromatic ring containing five or six ring atoms, comprising carbon and one, two, three, or four heteroatoms selected from non-peroxide oxygen, sulfur, and N (Y), wherein Y is absent or is H, O, (C1-C8) alkyl, phenyl, or benzyl. Non-limiting examples of heteroaryl groups include furanyl, imidazolyl, triazolyl, triazinyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, pyrroleyl, pyrazinyl, tetrazolyl, pyridinyl (or its N-oxide), thiophene, pyrimidinyl (or its N-oxide), indolyl, isoquinolinyl (or its N-oxide), quinolinyl (or its N-oxide), etc. The term “heteroaryl” can also include radicals of ortho-fused bicyclic heterocycles of about eight to ten ring atoms derived therefrom, derivatives derived by fusion with propylene, trimethylene, or tetramethylene diradicals. Examples of heteroaryl groups include, but are not limited to, furanyl, imidazolyl, triazolyl, triazinyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, pyrroleyl, pyrazinyl, tetrazolyl, pyridyl (or its N-oxide), thiophenyl, pyrimidinyl (or its N-oxide), indolyl, isoquinolinyl (or its N-oxide), quinolinyl (or its N-oxide), etc.

[0045] As used in this article, "halogen" refers to fluorine, chlorine, bromine, or iodine.

[0046] As used herein, the term "substituted" refers to all permitted substituents in the compounds described herein. In the broadest sense, permitted substituents include acyclic and cyclic, branched and unbranched, carbocyclic and heterocyclic, aromatic and non-aromatic substituents of organic compounds. Illustrative substituents include, but are not limited to, halogens, hydroxyl groups, or any other organic group containing any number of carbon atoms (preferably 1-14 carbon atoms), and optionally include one or more heteroatoms (e.g., oxygen, sulfur, or nitrogen groups) in the form of straight-chain, branched, or cyclic structures. Representative substituents include alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, phenyl, substituted phenyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, halogen, hydroxyl, alkoxy, substituted alkoxy, phenoxy, substituted phenoxy, aryloxy, substituted aryloxy, alkylthio, substituted alkylthio, phenylthio, substituted phenylthio, arylthio, substituted arylthio, cyano, isocyano, substituted isocyano, carbonyl, substituted carbonyl, carboxyl, substituted carboxyl, amino, substituted amino, amide, substituted amide, sulfonyl, substituted sulfonyl, sulfonic acid, phosphoryl, substituted phosphoryl, phosphonyl, substituted phosphonyl, polyaryl, substituted polyaryl, C3-C 20 Cyclic, substituted C3-C 20 Rings, heterocycles, substituted heterocycles, amino acids, peptides, and polypeptide groups.

[0047] Heteroatoms, such as nitrogen, may have hydrogen substituents and / or any permitted substituents in the organic compounds described herein that satisfy the valence state of the heteroatoms. It should be understood that “substitution” or “substituted” implies the condition that such substitution is consistent with the permitted valence states of the substituted atom and the substituent, and that the substitution produces a stable compound, i.e., a compound that does not spontaneously undergo transformation (e.g., by rearrangement, cyclization, elimination, etc.).

[0048] As used in this article, "polymer" refers to a molecule containing more than 10 monomer units.

[0049] As used herein, “water-soluble” generally means that at least 50, 75, 100, 125, 150, 200, 225 or 250 g can be dissolved in 1 L of water at 25°C.

[0050] As used herein, "hydroxide-containing reagent" generally refers to hydroxide-containing compounds commonly used in current hair straightening formulations, such as lye or other hydroxide-containing compounds (e.g., ammonium hydroxide). When these hydroxide-containing compounds are present in hair curling formulations, hydroxide ions produce formulations with high pH values, such as a pH range of 10 to 14, preferably a pH range of 12 to 14.

[0051] The terms “alkali reagent” or “base reagent” are used interchangeably in this document and refer to alkali metal hydroxides (e.g., sodium hydroxide and / or potassium hydroxide).

[0052] As used herein, a "thiol-containing reagent" means a reagent containing at least one thiol moiety. Exemplary thiol-containing reagents include, for example, thioglycolic acid, thiolactic acid, thioglycerol, or mercaptopropionic acid or a salt thereof, thioglycerin or a derivative thereof.

[0053] As used herein, "peroxide-based reagent" refers to a reagent containing at least one peroxide group. An exemplary peroxide-based reagent is hydrogen peroxide.

[0054] II. Active ingredient formulations This document discloses a method for using a surfactant formulation in combination with a hydroxide-containing agent or a formulation thereof for curling hair. Furthermore, when used during the curling process / treatment, the surfactant formulation can be used to control, select, or adjust the level of curl imparted to the hair compared to its natural state. The level of curl imparted depends on the amount of one or more surfactants applied, which can be expressed as the weight ratio of the weight of one or more surfactants (or the weight of the surfactant formulation) to the weight of the hydroxide-containing agent. Additionally, the inclusion of one or more surfactants can reduce hair breakage and damage during the curling process.

[0055] The formulation contains one or more active agents (also referred to herein as “compounds” or “active agents”) that may be combined with one or more cosmetically acceptable carriers and / or excipients that are considered safe and effective for application to human hair and / or human scalp and can be applied to an individual’s hair without causing undesirable biological side effects such as burns, itching and / or redness, or similar adverse reactions.

[0056] The amount of active agent present in the formulation is typically from about 0.05 wt% to about 25 wt% of the formulation, for example, from about 0.1 wt% to about 10 wt%, from about 0.1 wt% to 4 wt%, or from about 0.5 wt% to 3 wt%. Generally, the amount of active agent present in the formulation can be from about 0.5 wt% to about 5 wt% of the formulation.

[0057] At a temperature of about 25-30°C (preferably about 25°C), the surfactant is stable in aqueous solution (pH 3 to 8, preferably pH 3 to 5) for at least 2, 3, 4, 5, 6, 8, 9, 10, 11, or 12 months or longer. As used herein, “stable” with respect to shelf life means that at least 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, or 95% of the surfactant remains unchanged within the specified time period.

[0058] Active agent formulations typically do not contain strong bases, such as nitrogenous bases (e.g., guanidine, amidine, or their derivatives).

[0059] A. Surfactant The surfactant contains at least one reactive moiety capable of reacting with and forming a bond with a nucleophile, such as a thiol or amine. The surfactant optionally contains a linking group. The surfactant may contain one or more acidic groups, such as carboxylic acids, sulfonic acids, or phosphonic acids.

[0060] Unbound by theory, it is believed that the reactive portion forms stable (e.g., hydrolyzed stable) bonds upon reaction with nucleophilic substances (e.g., thiol groups) on the hair follicle. The term "stable" as used with respect to bonds formed in the hair follicle means that the bonds remain intact for at least one week, two weeks, three weeks, four weeks, one month, or two months or longer when exposed to water (pH 3 to 8, preferably pH 3 to 5) at temperatures ranging from about 5°C to about 100°C, about 20°C to about 75°C, more preferably about 20°C to about 50°C, about 25°C to about 40°C, or about 25°C to about 30°C, more preferably about 25°C.

[0061] Preferably, the reaction between the reactive moiety and the thiol occurs at room temperature, for example, from about 15°C to about 35°C, more preferably from about 20°C to about 30°C, and more preferably from about 22°C to about 27°C.

[0062] 1. Surfactants defined by Formula I In some embodiments, the surfactant has a structure according to Formula I:

[0063] Formula I in A, B, C, and D are reactive components containing one or more charges. R is a linking group containing two or more charges, wherein the charges are opposite to those on the reactive moiety, wherein n = 1-100, preferably n = 1-10, more preferably n = 1; each occurrence of p, q, r and s is independently an integer from 0 to 25, preferably 0 to 10, more preferably 0 to 2. The sum of p + q + r + s is equal to or greater than 2.

[0064] The reactive moiety can be present on any atom of the linking group. In some embodiments, the reactive moiety is the same. In some embodiments, one or more of the reactive moiety are different.

[0065] In some embodiments, the reactive portion is negatively charged, and the linking group has a positively charged portion. In other embodiments, the reactive portion is positively charged, and the linking group has a negatively charged portion. Typically, although stoichiometric imbalances may exist, the sum of the charges on the surfactant of Formula I is zero.

[0066] The reactive portion of the surfactant in Formula I is preferably linked via a linking group R. As used herein, the linking group R refers to one or more multifunctional substances, such as bifunctional, trifunctional, tetrafunctional, etc., which can be used to ionically bind two or more reactive portions without interfering with the reactive properties of the surfactant. The reactive portion can be linked to any part of the linking group R.

[0067] a. Linking group R In a preferred embodiment, n = 1 in Formula I, and the linking group R is not a polymer. The linking group R can be a single atom, such as a heteroatom (e.g., O or S), a group of atoms, such as a functional group (e.g., amine, -C(=O)-, -CH2-), or multiple groups of atoms, such as an alkylene chain. Suitable linking groups include, but are not limited to, oxygen, sulfur, carbon, boron, nitrogen, alkoxy, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, heteroaryl, ether, amine, and oligomers.

[0068] The linking group R is optionally and independently substituted by one or more substituents, which include hydrogen, halogen, cyano, alkoxy, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, heteroaryl, amine, hydroxyl, formyl, acyl, carboxylic acid (-COOH), and -C(O)R. 1 -C(O)OR 1 Carboxylate (-COO-), primary amides (e.g., -CONH2), secondary amides, -C(O)NR 1 R 2 -NR 1 R 2 -NR 1 S(O)2R 2 -NR 1 C(O)R 2 -S(O)2R 2 -SR 1 and -S(O)2NR 1 R 2 , sulfinyl group (e.g., -SOR) 1 ) and sulfonyl groups (e.g., -SOOR) 1 ); where R 1 and R 2 Each can be independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocycloalkyl, and heteroaryl; wherein R 1 and R 2 Each may optionally be independently substituted by one or more substituents selected from the group consisting of: halogen, hydroxyl, cyano, nitro, amino, alkylamino, dialkylamino, alkyl optionally substituted by one or more halogens or alkoxy or aryloxy groups, aryl optionally substituted by one or more halogens or alkoxy or alkyl or trihaloalkyl groups, heterocyclic alkyl optionally substituted by aryl or heteroaryl or =O groups, or alkyl optionally substituted by hydroxyl groups, cycloalkyl optionally substituted by hydroxyl groups, heteroaryl optionally substituted by one or more halogens or alkoxy or alkyl or trihaloalkyl groups, haloalkyl, hydroxyalkyl, carboxyl, alkoxy, aryloxy, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, and dialkylaminocarbonyl.

[0069] In some embodiments, the linking group R can be alkoxy, ether, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, heteroaryl, or amine.

[0070] b. Active agents according to Formula I An active agent according to Formula I contains at least two reactive moieties capable of reacting with nucleophiles (e.g., thiols or amines) to form covalent bonds. For example, the reactive moieties can react with thiol groups in hair to form stable covalent bonds. The reactive moieties are typically electrophilic moieties capable of forming salts with linking groups. Alternatively, the reactive moieties may be capable of reacting with free radicals.

[0071] An surfactant according to Formula I contains at least two reactive moieties. However, an surfactant may contain three, four, five, six or more reactive moieties.

[0072] When the reactive portion comes into contact with thiol groups in the hair, the reaction between the reactive portion and the thiol groups can be initiated at room temperature and pressure. In some embodiments, the reaction may require an initiator, such as heat, a catalyst, alkaline conditions, or a free radical initiator. The reaction rate between the reactive portion and the thiol can be increased by changing the temperature, pH, and / or by adding one or more excipients (e.g., a catalyst); however, this is generally not necessary.

[0073] Two or more reactive portions on the surfactant may be identical. In some embodiments, two or more reactive portions are different.

[0074] In some embodiments, the reactive portion is capable of undergoing a conjugated addition reaction. The reactive portion may independently be or contain a Michael acceptor, a succinimide-containing group, a maleimide-containing group, acrylonitrile, a benzoxazinone derivative, vinyl sulfone, vinyl sulfoxide imide, vinyl sulfonate, vinyl phosphonate, benzoxazinone, isocyanate, epoxide, an electrophilic portion containing a leaving group, an electrophilic thiol acceptor, acrylic acid or acrylate ions, methacrylic acid or methacrylate ions, styrene groups, acrylamide groups, methacrylamide groups, maleate ions, fumarate ions, itaconic acid ions, vinyl ether groups, allyl ether groups, allyl ester groups, vinyl ester groups, sulfonate ions, phosphonate ions, sulfoxide groups, sulfonamide groups, sulfinimide groups, sulfonamide groups, sulfonamide groups, or sulfonamide amide groups.

[0075] In a preferred embodiment, when present, each of the reactive portions A, B, C, and / or D independently contains a portion selected from the group consisting of: vinyl sulfone, acrylate ion, methacrylate ion, styrene group, acrylamide group, methacrylamide group, maleate ion, fumarate ion, and itaconic acid ion. Furthermore, in a preferred embodiment, n = 1, and the linking group R is not a polymer. Optionally, all reactive portions are identical. For example, in some embodiments, all reactive portions are maleate ions.

[0076] In some embodiments, the active agent according to Formula I has one of the following structures: or .

[0077] The active agent according to Formula I is further described in U.S. Patent No. 9,095,518, the disclosure of which is incorporated herein by reference.

[0078] 2. Surfactants defined by Formula II In some other embodiments, the active agent is a multifunctional compound containing ionizable functional groups capable of forming ionic bonds and functional groups capable of forming covalent bonds with nucleophiles (e.g., thiols or amines).

[0079] Surfactants can have the following formula II:

[0080] Formula II Wherein Z is a linking group or is absent, m and n are each independently selected from 1 to 6, provided that m + n is at least 2, B is a functional group capable of forming a covalent bond with a thiol or amine group, and A is an ionizable functional group. Preferably, the linking group Z is not a polymer. Optionally, the activator is a simple salt of formula II.

[0081] Suitable ionizable functional groups (group A) include, but are not limited to, acidic groups, such as carboxylic acids, sulfonic acids, and phosphonic acids, and basic groups, such as amines.

[0082] Suitable functional groups (group B) capable of forming covalent bonds with nucleophiles (e.g., thiols or amines) include, but are not limited to, Michael acceptors, alkyl halides, or sulfonates. Exemplary active agents according to Formula II may contain thiol-reactive functional groups, such as group B, as shown in the following sections: , , , , , or ; Where R is independently selected from hydrogen, C 1-6 Alkyl, aryl, or ionizable functional groups; Z' is oxygen (O), NH, or absent; and G is carbon (C) and g is 1, or G is sulfur (S) and g is 2. In a preferred embodiment, Z is a linking group or absent, the linking group is not a polymer, and group B is a functional group capable of forming a covalent bond with a thiol or amine group, group B being independently selected from the group consisting of: , and

[0083] R, Z', G, and g are as defined above.

[0084] a. Linking group Z of Formula II When present, the linking group Z can be or may contain alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, or heteroaryl groups. One or more carbon atoms in the alkyl, alkenyl, cycloalkyl, cycloalkenyl, and aryl groups may be replaced by heteroatoms to produce, for example, ether- or alkylamine-containing linking groups.

[0085] The linking group Z can be replaced by one or more substituents, which can be the same or different, and include hydrogen, halogen, cyano, alkoxy, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, heteroaryl, amine, hydroxyl, oxo, formyl, acyl, carboxylic acid (-COOH), and -C(O)R. 1 -C(O)OR 1 Carboxylates (-COO-), primary amides (e.g., -CONH2), secondary amides, -C(O)NR 1 R 2 -NR 1 R 2 -NR 1 S(O)2R 2 -NR 1 C(O)R 2 -S(O)2R 2 -SR 1 and -S(O)2NR 1 R 2 sulfinyl groups (e.g., -SOR) 1 ) and sulfonyl groups (e.g., -SOOR) 1 ); where R 1 and R 2 Each can be independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocycloalkyl, and heteroaryl; wherein R 1 and R 2Each may optionally be independently substituted by one or more substituents selected from the group consisting of: halogen, hydroxyl, oxo, cyano, nitro, amino, alkylamino, dialkylamino, alkyl optionally substituted with one or more halogens or alkoxy or aryloxy groups, aryl optionally substituted with one or more halogens or alkoxy or alkyl or trihaloalkyl groups, heterocyclic alkyl optionally substituted with aryl or heteroaryl or oxo, or alkyl optionally substituted with hydroxyl, cycloalkyl optionally substituted with hydroxyl, heteroaryl optionally substituted with one or more halogens or alkoxy or alkyl or trihaloalkyl groups, haloalkyl, hydroxyalkyl, carboxyl, alkoxy, aryloxy, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, and dialkylaminocarbonyl.

[0086] In some preferred embodiments, the linking group Z is C 1-10 The alkyl group may be unsubstituted or substituted once or multiple times with oxo, hydroxyl, carboxyl, amide, or amino groups. Preferably, the linking group Z is C. 1-4 Alkyl groups. Alkyl groups can be straight-chain or branched. Alkyl groups can also be interrupted once or multiple times by heteroatoms selected from oxygen, sulfur, and nitrogen. An example of a dicarboxylic acid with heteroatom interruption is thiodipropionic acid. In other embodiments, the alkyl group may contain one or more double or triple bonds.

[0087] In some embodiments, the active agent according to Formula II has one of the following structures: , , or

[0088] Or simply salts of these structures.

[0089] As used herein, the term "simple salt" refers to a salt formed by an ionized agent of formula II and a counterionic group having a charge opposite to that of the ionizable functional group A. In a preferred embodiment, the simple salt comprises only one agent and one counterionic group. The counterionic group may be a suitable ionized metal or an optionally substituted C1-C moiety covalently bonded to the ionized portion. 10 C1-C8 or C1-C6 alkyl, C2-C 10 C2-C8 or C2-C6 alkenyl, or C2-C 10 C2-C8 or C2-C6 alkynyl counterionic groups. For example, if the ionizable functional group A has a negative charge (e.g., -C(O)O). - If the counterionic group has a positive charge (e.g., an ammonium group), then the counterionic group has a positive charge. C1-C 10 C1-C8 or C1-C6 alkyl, C2-C 10C2-C8 or C2-C6 alkenyl, or C2-C 10 The C2-C8 or C2-C6 alkynyl counterion group can be substituted once or multiple times with substituents as defined above regarding the linking group Z. Optionally substituted C3-C... 10 The C3-C8 or C3-C6 alkyl counterionic group can be straight-chain, branched, or cyclic. C1-C 10 C1-C8 or C1-C6 alkyl, C2-C 10 C2-C8 or C2-C6 alkenyl, or C2-C 10 The C2-C8 or C2-C6 alkynyl counterion group may also be interrupted once or multiple times along the skeleton by heteroatoms selected from oxygen, sulfur, and / or nitrogen. In some embodiments, the counterion group does not contain a carbon-carbon double bond. In some other embodiments, the molecular weight of the counterion group is less than about 200 g / mol, 150 g / mol, 125 g / mol, 100 g / mol, 100 g / mol, 90 g / mol, 80 g / mol, 70 g / mol, 60 g / mol, 50 g / mol, 40 g / mol, 30 g / mol, or 20 g / mol.

[0090] Exemplary counterionic groups include, but are not limited to, sodium ions, potassium ions, ammonium ethanol, and allyl ammonium.

[0091] 3. Surfactants defined by Formula III In some embodiments, when the active agent of Formula II is a simple salt, it may have the structure of Formula III:

[0092] Formula III Where Z is a linking group or is absent, m and n are each an independent integer selected from 1 to 6, provided that m + n is at least 2, B is a functional group capable of forming a covalent bond with a nucleophile (e.g., a thiol or amine group), A is an ionizable functional group as defined above, and C is an ionic group that is also capable of forming a covalent bond with a thiol and has a charge opposite to that of the ionizable group A. Group C is ionicly bonded (indicated by the dashed line) to group A. For ionic group C, o is an independent integer value selected from 1 to 6 such that the sum of the charges of group C and ionizable group A is zero. Preferably, the linking group Z is not a polymer.

[0093] In the surfactant of Formula III, group C is an ionic group that is ionicly bonded to the ionizable group A and can also form a covalent bond with a thiol. Group C can be a Michael acceptor, a succinimide-containing group, a maleimide-containing group, acrylonitrile, a benzoxazinone derivative, vinyl sulfone, vinyl sulfoxide imide, vinyl sulfonate, vinyl phosphonate, benzoxazinone, isocyanate, epoxide, an electrophilic moiety containing a leaving group, an electrophilic thiol acceptor, acrylic acid or acrylate ions, methacrylic acid or methacrylate ions, styrene groups, acrylamide groups, methacrylamide groups, maleate ions, fumarate ions, itaconic acid ions, vinyl ether groups, allyl ether groups, allyl ester groups, vinyl ester groups, sulfonate ions, phosphonate ions, sulfoxide groups, sulfonamide groups, sulfinimide groups, sulfonamide groups, sulfonamide groups, or sulfonamide amide groups. For example, group C can be allylammonium or 2-(methacryloyloxy)ethyl-1-ammonium.

[0094] The active agent according to Formula III may contain a thiol reactive functional group, which reacts with a nucleophile (e.g., a thiol) as group B. Exemplary thiol reactive functional groups include, but are not limited to, those shown in the following portions: , , , , , or ; Where R is independently selected from hydrogen, C 1-6 Alkyl, aryl, or ionizable functional groups; Z' is oxygen (O), NH, or absent; and G is carbon (C) and g is 1, or G is sulfur (S) and g is 2. In a preferred embodiment, Z is a linking group or absent, the linking group is not a polymer, and group B is a functional group capable of forming a covalent bond with a thiol or amine group, group B being independently selected from the group consisting of: , and

[0095] R, Z', G, and g are as defined above.

[0096] a. The linking group Z of Formula III When present, the linking group Z can be or may contain alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, or heteroaryl groups. One or more carbon atoms in the alkyl, alkenyl, cycloalkyl, cycloalkenyl, and aryl groups may be replaced by heteroatoms to produce, for example, ether- or alkylamine-containing linking groups.

[0097] The linking group Z may optionally be substituted with one or more substituents, which may be the same or different, and include hydrogen, halogen, cyano, alkoxy, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, heteroaryl, amine, hydroxyl, oxo, formyl, acyl, carboxylic acid (-COOH), -C(O)R 1 -C(O)OR 1 Carboxylates (-COO-), primary amides (e.g., -CONH2), secondary amides, -C(O)NR 1 R 2 -NR 1 R 2 -NR 1 S(O)2R 2 -NR 1 C(O)R 2 -S(O)2R 2 -SR 1 and -S(O)2NR 1 R 2 sulfinyl groups (e.g., -SOR) 1 ) and sulfonyl groups (e.g., -SOOR) 1 ); where R 1 and R 2 Each can be independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocycloalkyl, and heteroaryl; wherein R 1 and R 2 Each may optionally be independently substituted by one or more substituents selected from the group consisting of: halogen, hydroxyl, oxo, cyano, nitro, amino, alkylamino, dialkylamino, alkyl optionally substituted with one or more halogens or alkoxy or aryloxy groups, aryl optionally substituted with one or more halogens or alkoxy or alkyl or trihaloalkyl groups, heterocyclic alkyl optionally substituted with aryl or heteroaryl or oxo, or alkyl optionally substituted with hydroxyl, cycloalkyl optionally substituted with hydroxyl, heteroaryl optionally substituted with one or more halogens or alkoxy or alkyl or trihaloalkyl groups, haloalkyl, hydroxyalkyl, carboxyl, alkoxy, aryloxy, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, and dialkylaminocarbonyl.

[0098] In some preferred embodiments, the linking group Z is C 1-10 The alkyl group may be unsubstituted or substituted once or multiple times with oxo, hydroxyl, carboxyl, amide, or amino groups. Preferably, the linking group Z is C. 1-4 Alkyl groups. Alkyl groups can be straight-chain or branched. Alkyl groups can also be interrupted once or multiple times by heteroatoms selected from oxygen, sulfur, and nitrogen. An example of a dicarboxylic acid with heteroatom interruption is thiodipropionic acid. In other embodiments, the alkyl group may contain one or more double or triple bonds.

[0099] In some embodiments, the active agent of Formula III has one of the following structures: or .

[0100] B. Excipients Active ingredient formulations typically contain one or more cosmetically acceptable excipients. Cosmetically acceptable excipients include, but are not limited to, water, preservatives, antioxidants, chelating agents, sunscreens, vitamins, dyes, hair dyes, proteins, amino acids, natural extracts (e.g., plant extracts), moisturizers, fragrances, perfumes, oils, emollients, lubricants, butters, penetrants, thickeners, viscosity modifiers, polymers, resins, hair fixatives, film-forming agents, surfactants, cleansing agents, emulsifiers, opacifiers, volatiles, aerosols, liquid mediators, carriers, salts, pH adjusters (e.g., citric acid), neutralizers, buffers, hair conditioners, antistatic agents, anti-frizz agents, anti-dandruff agents, absorbents, and combinations thereof.

[0101] In some embodiments, the active agent formulation contains no thickener or substantially no thickener (i.e., viscous agent).

[0102] The formulation may contain one or more cosmetically acceptable excipients. In some forms, the formulation contains an active agent, water, and optionally a preservative and / or fragrance.

[0103] Formulations intended for curling hair during or immediately after application of a hydroxide-containing formulation can be in any suitable physical form. Suitable forms include, but are not limited to, liquids, lotions, emulsions, mousses, sprays, gels, creams, shampoos, conditioners, etc., of low to medium viscosity. Depending on the form of the formulation (e.g., liquid, spray, cream), the formulation may or may not contain suitable excipients (e.g., those listed above).

[0104] The amount of excipients acceptable for cosmetics is generally from about 10 wt% to about 99.99 wt% of the formulation, preferably from about 40 wt% to about 99 wt%, and more preferably from about 80 wt% to about 99 wt%.

[0105] 1. Surfactants Surfactants are surfactants that reduce the surface tension of water and allow formulations to glide or slide across hair. Surfactants can also include detergents and soaps. Surfactants can be amphoteric, anionic, or cationic. Suitable surfactants that can be used in formulations include, but are not limited to, 3-aminopropanesulfonic acid, amygdalinamide, amygdalinamide-propyl betaine, amygdalinamide-propylamine oxide, hydrogenated aluminum tallow glutamate, aluminum lanolinate, aminoethyl sulfate, aminopropyl lauryl glutamine, and C...12-15 Alkyl ammonium sulfate, C 12-15 Alkyl alcohol polyether ammonium sulfate, C 12-16 Alkyl ammonium sulfate, C 9-10 Ammonium perfluoroalkyl sulfonate, ammonium octyl ether sulfate, ammonium octyl ether-3 sulfate, ammonium monoglyceride sulfate, ammonium sulfate, ammonium isothiosulfate, ammonium cocoyl sarcosinate, ammonium cumene sulfonate, ammonium dimethyl polysiloxane copolyol sulfate, ammonium dodecylbenzene sulfonate, ammonium isostearate, ammonium lauryl ether sulfate, ammonium lauryl ether-12 sulfate, ammonium lauryl ether-5 sulfate, ammonium lauryl ether-6 carboxylate, ammonium lauryl ether-7 sulfate, ammonium lauryl ether-8 carboxylate, ammonium lauryl ether-9 sulfate, ammonium lauroyl sarcosinate, ammonium lauryl sulfate, ammonium lauryl sulfosuccinate, ammonium myristyl ether sulfate, ammonium myristyl sulfate, ammonium nonyl styrene-30 sulfate, ammonium nonyl styrene-4 sulfate, ammonium oleate, ammonium palm kernel sulfate, polyacrylic acid Ammonium, ammonium stearate, tall oil fatty acid ammonium, ammonium xylenesulfonate, ammonium xylenesulfonate, isostearyl gelatin / keratin amino acid / lysine hydroxypropyltrimethylammonium chloride AMP salt, isostearyl hydrolyzed collagen AMP salt, wild almond oil PEG-6 ester, wild almond oleamide, wild almond oleamide aminopropyl betaine, peanut alcohol polyether-20, avocado oleamide, avocado oleamide aminopropyl betaine, babassu oleamide, babassu oleamide aminopropyl betaine, babassu oleamide aminopropyl betaine, behenylbenzyl dimethyl ammonium chloride, behenamide, behenamide, behenamide aminopropyl betaine, behenamine oxide, sodium lauryl ether sulfate, sodium lauryl sulfate, polyoxyether of lauryl alcohol or cetearyl alcohol polyether-20, or combinations thereof.

[0106] Suitable anionic surfactants include, but are not limited to, those containing carboxylate, sulfonate, and sulfate ions. Examples of anionic surfactants include long-chain alkyl sulfonates such as sodium, potassium, ammonium, and alkyl aryl sulfonates, such as sodium dodecylbenzene sulfonate; dialkyl sulfosuccinates such as sodium dodecylbenzene sulfonate; dialkyl sulfosuccinates such as bis(2-ethylthio)-sulfosuccinate; and alkyl sulfates such as sodium lauryl sulfate. Cationic surfactants include, but are not limited to, quaternary ammonium compounds such as benzalkonium chloride, benzyl chloride, cetrimonium bromide, stearyl dimethyl benzyl ammonium chloride, polyoxyethylene, and cocoamine. Examples of nonionic surfactants include ethylene glycol monostearate, propylene glycol myristate, glyceryl monostearate, glyceryl stearate, polyglycerol-4-oleate, sorbitol acylate, sucrose acylate, PEG-150 laurate, PEG-400 monolaurate, polyoxyethylene monolaurate, polysorbate, polyoxyethylene octylphenyl ether, PEG-1000 cetyl ether, polyoxyethylene tridecyl ether, polypropylene glycol butyl ether, and poloxamer. ®401. Stearoyl monoisopropanolamide and polyoxyethylene hydrogenated tallow amide. Examples of amphoteric surfactants include sodium N-dodecyl-β-alanine, sodium N-lauryl-β-iminodipropionate, myristoyl amphoteric acetate, lauryl betaine, and lauryl sulfobetaine.

[0107] The formulation may contain more than one surfactant.

[0108] Optionally, the surfactant content is from about 0.1% to about 15% of the weight of the formulation, preferably from about 1% to about 10% of the weight of the formulation.

[0109] 2. Moisturizer Emollients are materials used to prevent skin from becoming moist or irritated, soften the skin, soothe the skin, apply to the skin, lubricate the skin, moisturize the skin, protect the skin, and / or cleanse the skin. Suitable emollients for use in formulations include, but are not limited to, siloxane compounds (e.g., polydimethylsiloxane, cyclodimethylsiloxane, polydimethylsiloxane copolyol or mixtures of cyclopentadiene and polydimethylsiloxane / vinyldimethylsiloxane crosspolymers, cyclopentadiene polysiloxane), polyols (e.g., sorbitol, glycerin, propylene glycol, ethylene glycol, polyethylene glycol, octyl glycol, polypropylene glycol, 1,3-butanediol, hexanediol, isopentyl glycol, xylitol); ethylhexyl palmitate; triglycerides (e.g., caprylic / capric triglycerides); and fatty acid esters (e.g., cetearyl isononanoate or cetyl palmitate). In one specific embodiment, the emollient is polydimethylsiloxane, amide-polydimethylsiloxane, polydimethylsiloxane alcohol, cyclopentasiloxane, polydimethylsiloxane PEG-7 panthenol potassium phosphate, or a combination thereof. The formulation may contain more than one emollient.

[0110] Optionally, the content of the emollient is from about 0.5% to about 15% of the weight of the formulation, preferably from about 1% to about 10% of the weight of the formulation.

[0111] 3. Emulsifiers The formulation may also contain one or more emulsifiers. Suitable emulsifiers include, but are not limited to, copolymers of unsaturated esters and styrene sulfonate monomers, cetearyl alcohol, glyceryl esters, polyoxyethylene glycol ether of cetearyl alcohol, stearic acid, polysorbate-20, cetearyl alcohol polyether-20, lecithin, ethylene glycol stearate, polysorbate-60, or polysorbate-80, or combinations thereof. The formulation may contain more than one emulsifier.

[0112] Optionally, the content of the emulsifier is from about 0.05% to about 15% of the weight of the formulation, preferably from about 0.1% to about 10% of the weight of the formulation.

[0113] 4. Preservatives The formulation may contain one or more preservatives to prevent the growth of microorganisms in the formulation. Suitable preservatives include, but are not limited to, glycerol-containing compounds (e.g., glycerol or ethylhexylglycerol or phenoxyethanol), benzyl alcohol, parabens (methylparaben, ethylparaben, propylparaben, butylparaben, isobutylparaben, etc.), sodium benzoate, ethylenediaminetetraacetic acid (EDTA), potassium sorbate and / or grapefruit seed extract, or combinations thereof. The formulation may contain more than one preservative. Other preservatives known in the cosmetics industry include salicylic acid, DMDM ​​hydantoin, formaldehyde, chlorphenesin, triclosan, imidazolidinyl urea, diazolidinyl urea, sorbic acid, methylisothiazolinone, sodium dehydroacetate, dehydroacetic acid, quaternary ammonium salt-15, silachlor, zinc pyrithione, sodium metabisulfite, 2-bromo-2-nitropropane, chlorhexidine digluconate, polyaminopropyl biguanide, benzalkonium chloride, sodium sulfite, sodium salicylate, citric acid, neem oil, essential oils (various), lactic acid, and vitamin E (tocopherol).

[0114] Optionally, the preservative content is from about 0.1% to about 5% of the weight of the formulation, preferably from about 0.3% to about 3% of the weight of the formulation. Preferably, the formulation does not contain parabens.

[0115] 5. Conditioning agents The formulation may contain one or more conditioning agents. Suitable conditioning agents include, but are not limited to, siloxane reagents (e.g., siloxane quaternary ammonium salt-8), panthenol, hydrolyzed wheat and / or soy protein, amino acids (e.g., wheat amino acids), rice bran wax, meadowfoam seed oil, mango seed oil, grape seed oil, jojoba seed oil, sweet almond oil, hydroxyethyl behenylaminopropyl dimethyl ammonium chloride, aloe vera leaf extract, aloe vera leaf juice, phytanetriol, panthenol, retinyl palmitate, behenyltrimethylammonium sulfate, cyclopentasiloxane, quaternary ammonium salt-91, stearoylaminopropyl dimethylamine, and combinations thereof.

[0116] Optionally, the content of the conditioning agent is from about 0.01% to about 5% of the weight of the preparation, preferably from about 0.05% to about 3% of the weight of the preparation.

[0117] 6. Diluent As used herein, a diluent refers to a substance that dilutes the active agent. Water is a preferred diluent. Formulations typically contain more than one percent (wt) of water, preferably more than five percent (wt) of water, more preferably more than 50% (wt) of water, and most preferably more than 80% (wt) of water. Alcohols, such as ethanol and isopropanol, may be used at low concentrations (about 0.5% by weight of the formulation) to enhance hair or skin penetration and / or reduce odor.

[0118] 7. Viscosity modifier The formulations described herein are preferably low-viscosity formulations, possessing the fluidity of a liquid that flows easily at standard temperature and pressure, such as properties similar to water or milk. Optionally, the formulations may have a more viscous viscosity but still flow at standard temperature and pressure, such as a viscosity similar to shampoo.

[0119] The formulation optionally contains one or more viscosity modifiers. In some embodiments, the activator formulation and / or combination formulation contains no or substantially no thickener (i.e., viscous agent). As used herein, “substantially no” means that the formulation contains less than about 5%, 4%, 3%, 2%, or 1% of one or more thickeners. In some embodiments, the activator formulation contains less than about 1% of one or more thickeners. Thickeners include, but are not limited to, viscous liquids (e.g., polyethylene glycol), semi-synthetic polymers (e.g., semi-synthetic cellulose derivatives), synthetic polymers (e.g., carbomer, poloxamer, and polyethyleneimine (e.g., PEI-10)), naturally occurring polymers (e.g., gum arabic, tragacanth, alginate (e.g., sodium alginate), carrageenan), alcohols (e.g., cetyl alcohol), plant gums (e.g., xanthan gum), petrolatum, waxes, particulate-associated colloids (e.g., bentonite, colloidal silica, and microcrystalline cellulose), surfactants (e.g., PPG-2 hydroxyethyl coconut oil / isostearylamide), emulsifiers (e.g., distearate polyether-75 IPDI), and salts (e.g., sodium chloride), and combinations thereof.

[0120] 8. Antioxidants The formulation may contain one or more antioxidants. Examples include, but are not limited to, tocopherol, BHT, ascorbic acid, tea extract, ascorbyl palmitate, magnesium ascorbate phosphate, carotenoids, resveratrol, triethyl citrate, arbutin, kojic acid, tetrahexyldecyl ascorbate, superoxide dismutase, zinc, sodium metabisulfite, lycopene, ubiquinone, and combinations thereof.

[0121] 9. Emulsifiers The formulation may contain one or more emulsifiers. Emulsifiers are added to the formulation to give it an emulsified appearance. Suitable emulsifiers include, but are not limited to, polyethylene distearate and ethoxylated fatty alcohols.

[0122] C. Properties of surfactant formulations 1. Cream In some embodiments, the active agent formulation may be in the form of a cream. Creams typically contain an active agent of Formula I, II, or III in a suitable carrier. Creams may contain a combination of active agents. Active agents may be included at any suitable concentration. Typical concentrations of active agents in creams range from small amounts, such as about 0.05 wt% to about 25 wt% of the formulation, for example, about 0.1 wt% to about 10 wt%, about 0.1 wt% to 4 wt%, or about 0.5 wt% to 3 wt%. Typically, the amount of active agent present in the formulation may be about 0.5 wt% to about 5 wt% of the formulation. Preferably, the cream contains active agents at concentrations ranging from 0.1% (wt) to 5% (wt), more preferably from 0.1% wt to 3% (wt). While higher concentrations of active agents may be present in the cream, they are generally not required to obtain the desired results.

[0123] In addition, creams may contain oils, hair conditioners, and / or thickeners. Creams may also contain fragrances, plant extracts, and / or surfactants. Creams may be packaged in tubes, drums, bottles, or other suitable containers.

[0124] When an active agent formulation in cream form is combined with a hydroxide-containing formulation (e.g., mixed to form a combination formulation or applied to the hair simultaneously), no precipitates containing metal ions are formed.

[0125] 2. Liquid surfactant formulations In some embodiments, a liquid surfactant formulation is provided, which, upon use, is mixed with a second formulation containing a hydroxide-containing reagent to provide a combined formulation for curling hair. In these embodiments, the liquid surfactant formulation may contain any suitable concentration of surfactant, typically a diluent, in a suitable carrier, as described above. The liquid surfactant formulation may contain a combination of surfactants. The concentration of surfactant is adapted, as needed, to provide a combined formulation with an appropriate final volume and final concentration of surfactant.

[0126] For example, liquid surfactant formulations may contain surfactants at concentrations ranging from about 0.05 wt% to about 25 wt% of the formulation, such as about 0.1 wt% to about 10 wt%, about 0.1 wt% to 4 wt%, or about 0.5 wt% to 3 wt%. Typically, the amount of surfactant present in the formulation may be from about 0.5 wt% to about 5 wt% of the formulation. In a preferred embodiment, the liquid surfactant formulation contains about 5% (wt) to 20% (wt) of surfactant. Preferably, the surfactant-containing formulation is odorless.

[0127] a. Concentration of surfactant In some embodiments, a first active agent formulation is provided, which may contain one or more active agents according to Formula I, Formula II, and / or Formula III, typically containing about 0.1 to about 50 wt% of one or more active agents described herein. The active agent formulation may contain about 0.1 to about 30 wt%, about 0.1 to about 20 wt%, about 0.1 to about 10 wt%, about 0.1 to about 10 wt%, or about 0.5 to 5 wt% of one or more active agents described herein. The active agent formulation is typically in an aqueous solution and optionally contains other suitable ingredients and / or excipients. The active agent formulation is preferably a liquid active agent formulation. In some embodiments, the active agent formulation is preferably not in cream form. The active agent formulation may be mixed with a hydroxide-containing formulation to form a combined formulation as described below.

[0128] In some embodiments, such as when the active agent is diaminopropyl diethylene glycol dimaleate, the active agent formulation may contain about 0.1 to about 30 wt%, about 0.1 to about 20 wt%, about 0.1 to about 10 wt%, about 0.1 to about 10 wt%, or about 0.5 to 5 wt% of diaminopropyl diethylene glycol dimaleate. Optionally, the active agent formulation contains about 0.5 to about 10 wt%, about 1 to about 9 wt%, about 2 to about 8 wt%, about 2 to about 6 wt%, about 2.5 to about 6 wt%, about 3 to about 5.5 wt%, or about 3 to about 5 wt% of diaminopropyl diethylene glycol dimaleate.

[0129] In some embodiments, such as when the active agent is maleic acid or a simple salt thereof, the active agent formulation may contain about 0.1 to about 30 wt%, about 0.1 to about 20 wt%, about 0.1 to about 10 wt%, about 0.1 to about 10 wt%, or about 0.5% to 5 wt% of maleic acid or a simple salt thereof. Optionally, the active agent formulation contains about 0.5 to about 10 wt%, about 0.5 to about 9 wt%, about 1 to about 8 wt%, about 1 to about 7 wt%, about 1 to about 6 wt%, about 1 to about 3 wt%, or about 1 to about 2 wt% of maleic acid or a simple salt thereof.

[0130] In some embodiments, a second surfactant formulation may be provided, which may be further applied to the hair after the curling treatment as described herein. The second surfactant formulation may contain the same surfactant as the first surfactant formulation, or it may contain a different surfactant than the surfactant in the first surfactant formulation. The second surfactant formulation may contain the same or a different surfactant concentration as the surfactant concentration in the first surfactant formulation. The second surfactant formulation typically contains about 0.1 to 50 wt% of one or more surfactants described herein. The surfactant formulation may contain about 0.1 to about 30 wt%, about 0.1 to about 20 wt%, about 0.1 to about 10 wt%, about 0.1 to about 10 wt%, or about 0.5 to 5 wt% of one or more surfactants described herein.

[0131] The second surfactant may be in liquid or cream form; optionally, the second surfactant is an aqueous solution. Optionally, the second surfactant formulation contains other suitable ingredients and / or excipients.

[0132] III. Hydroxide-containing preparations As used herein, the term "hydroxide-containing preparation" refers to a preparation containing one or more hydroxide-containing reagents. Hydroxide-containing preparations are preferably odorless. Hydroxide-containing preparations are preferably aqueous preparations.

[0133] Hydroxide formulations do not contain thiol-based reducing agents, such as thioglycolic acid, thiolactic acid, thioglycerol, or mercaptopropionic acid or its salts, thioglycerin, or derivatives thereof. In some other embodiments, the hydroxide formulations also do not contain other types of reducing agents, such as sodium bisulfite, ammonium disulfide, dihydrolipoic acid, zinc formaldehyde sulfoxylate, sodium formaldehyde sulfoxylate, sodium metabisulfite, potassium borohydride, or polyethylene glycol-modified thiols and / or hydroquinone.

[0134] Hydroxide-containing formulations and methods for their preparation are known in the art. In preferred embodiments, the hydroxide-containing formulation is a liquid, while commercially available, non-preferred hydroxide-containing formulations are typically in paste form, such as straightening formulations from the following commercial brands: Mizani® Rhelaxer, Design Essentials®, and Dudley's Q®.

[0135] Exemplary hydroxide-containing reagents include, but are not limited to, alkali metal hydroxides, such as sodium hydroxide, lithium hydroxide, calcium hydroxide, and potassium hydroxide. In some other embodiments, the reagent is ammonium hydroxide or guanidine hydroxide. Hydroxide-containing reagents are known to those skilled in the art.

[0136] In a preferred embodiment, the hydroxide-containing formulation is free of any thiol-containing compounds or reagents. Alternatively, the hydroxide-containing formulation is substantially free of any thiol-containing compounds or reagents. As used herein, "substantially free" means that the formulation contains less than about 1 wt%, less than about 0.9 wt%, less than about 0.8 wt%, less than about 0.7 wt%, less than about 0.6 wt%, less than about 0.5 wt%, less than about 0.4 wt%, less than about 0.3 wt%, less than about 0.2 wt%, or less than about 0.1 wt% of any thiol-containing compound or reagent.

[0137] IV. Combination formulations containing surfactants and hydroxide-containing reagents As used herein, the term "combination formulation" refers to a formulation containing one or more hydroxide-containing reagents and one or more of the above-described active agents. Combination formulations are preferably aqueous formulations.

[0138] Combination formulations typically do not contain nitrogenous bases, such as guanidine, amidine, acetamide, or their salts or derivatives.

[0139] In some embodiments, separate active agent formulations and hydroxide-containing formulations are provided, which are mixed upon use to provide a combined formulation.

[0140] In other embodiments, combination formulations are provided (i.e., the active agent and hydroxide-containing reagent are provided as a single formulation).

[0141] 1. Concentration The formulation may contain one or more hydroxide-containing agents at concentrations of about 0.1 to 5% (wt), about 0.1 to 3% (wt), about 0.1 to 2% (wt), or about 0.1 to 1% (wt). In preferred embodiments, the concentration of one or more hydroxide-containing agents in the formulation is about 0.1 wt%, 0.2 wt%, 0.3 wt%, 0.4 wt%, 0.5 wt%, 0.6 wt%, 0.7 wt%, 0.8 wt%, 0.9 wt%, 1.0 wt%, 1.1 wt%, 1.2 wt%, 1.3 wt%, 1.4 wt%, or 1.5 wt%. The concentration of the active agent in the formulation may range from about 0.5% (wt) to about 50% (wt) or greater. In some embodiments, the formulation contains about 0.5% (wt) to 20% (wt) of the active agent. In some embodiments, the combination formulation contains about 0.1 wt%, 0.2 wt%, 0.3 wt%, 0.4 wt%, 0.5 wt%, 0.6 wt%, 0.7 wt%, 0.8 wt%, 0.9 wt%, 1.0 wt%, 1.1 wt%, 1.2 wt%, 1.3 wt%, 1.4 wt%, 1.5 wt%, 1.6 wt%, 1.7 wt%, 1.8 wt%, 1.9 wt%, 2.0 wt%, 2.0 wt%, 2.1 wt%, 2.2 wt%, 2.3 wt%, 2.4 wt%, 2.5 wt%, 2.6 wt%, 2.7 wt%, 2.8 wt%, 2.9 wt%, or 3.0 wt%, or any concentration between the listed active agent concentrations.

[0142] In some embodiments, the formulation contains a molar excess of a hydroxide-containing reagent compared to an active agent having one or more acidic groups. In some other embodiments, the formulation is prepared based on a molar ratio of the amount of the hydroxide-containing reagent to the amount of acidic groups (i.e., carboxylic acids) present in the active agent, wherein the molar ratio may be about 2:1 or 1.5:1. In other embodiments, the molar ratio of the amount of the hydroxide-containing reagent to the amount of acidic groups (i.e., carboxylic acids) may be greater than or less than about 2:1 or 1.5:1, depending on the presence of one or more excipients and / or buffers, which may be acidic or basic and may be present in the formulation.

[0143] 2. Viscosity The formulation may be in liquid form. Preferably, the viscosity of the liquid is less than that of the beauty cream, i.e., less than about 8,000 cP, optionally less than 5,000 cP.

[0144] The viscosity of a combination formulation can be determined using known methods for measuring fluid viscosity. In one non-limiting exemplary method, a Ford cup viscometer can be used to determine the viscosity of a Newtonian fluid according to the test method provided in ASTM D 1200-94. A Ford cup viscometer can also be used to determine the viscosity of a non-Newtonian fluid according to the test method provided in ASTM D 2196. Classical “Newtonian” fluids, as commonly used herein, exhibit viscosity that is substantially independent of shear rate. However, “non-Newtonian fluids” exhibit viscosity that decreases or increases with increasing shear rate, e.g., fluids that are “shear-thinning” or “shear-thickening,” respectively. These and other methods for measuring viscosity are described in Viswanath et al., “Viscosity of Liquids: Theory, Estimation, Experiment, and Data,” Dordrecht: Springer, 2007, Print. Exemplary fluid viscosities measured in centipoises by the viscosity cup method (at 20°C) include water (1 cP), hand cream (8,000 cP), liquid soap (85 cP), and shampoo (3,000-5,000 cP).

[0145] Suitable viscosity ranges for the formulation are approximately 1 to 3,000 cP, 1 to 2,000 cP, 1 to 1,000 cP, 1 to 750 cP, 1 to 500 cP, 1 to 250 cP, 1 to 100 cP, 1 to 90 cP, 1 to 80 cP, 1 to 70 cP, 1 to 60 cP, 1 to 50 cP, 1 to 40 cP, 1 to 30 cP, 1 to 20 cP, or 1 to 10 cP. In some embodiments, the formulation has a viscosity, measured by a viscosity cup viscometer, within 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 20%, or 30% of the viscosity of a reference fluid (e.g., water or shampoo) measured under the same conditions. In a preferred embodiment, the viscosity of the formulation is less than 8,000 cP.

[0146] 3. pH value In some embodiments, the pH of the combination formulation is about 11 or greater. In some embodiments, the pH of the combination formulation is about 10 or greater. In some embodiments, the pH of the combination formulation is about 9.5 or greater, 9.6 or greater, 9.7 or greater, 9.8 or greater, 9.9 or greater, 10.0 or greater, 10.1 or greater, 10.2 or greater, 10.3 or greater, 10.4 or greater, 10.5 or greater, 10.6 or greater, 10.7 or greater, 10.8 or greater, 10.9 or greater, 11.0 or greater, 11.1 or greater, 11.2 or greater, 11.3 or greater, 11.4 or greater, 11.5 or greater, 11.6 or greater, 11.7 or greater, 11.8 or greater, 11.9 or greater, or 12.0 or greater. In some other embodiments, the pH of the combination formulation is about 9.5, 9.6, 9.7, 9.8, 9.9, 10.0, 10.1, 10.2, 10.3, 10.4, 10.5, 10.6, 10.7, 10.8, 10.9, 11.0, 11.1, 11.2, 11.3, 11.4, 11.5, 11.6, 11.7, 11.8, 11.9, or 12.0.

[0147] 4. Tasteless The formulation typically does not contain any unpleasant odor. Preferably, the formulation is odorless. However, if desired, it may contain a fragrance.

[0148] A. A combination curly formulation formed by mixing immediately before application. In some embodiments, a combination formulation is provided, namely a first activator formulation and a second formulation containing a hydroxide-containing reagent, and these formulations are mixed upon use (e.g., by a stylist and / or colorist in a hair salon) to provide a combination formulation for curling hair.

[0149] In some embodiments of the combination formulation, the weight ratio of one or more hydroxide-containing agents to one or more active agents in the combination formulation may range from about 10:1 to about 1:5; 5:1 to 1:5; 4:1 to 1:4; or 3:1 to 1:3. In some embodiments, the weight ratio of one or more hydroxide-containing agents to one or more active agents in the combination formulation ranges from about 10:1 to about 1:1; 5:1 to 1:1; 4:1 to 1:1; or 3:1 to 1:1. In some instances, the weight ratio is about 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, or 1:5, preferably about 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, or 1:5, or within about 10% of these ratios.

[0150] In this combination formulation, the amount of active agent present will not cause the pH value of the combination formulation to decrease to below about 9.5, more preferably, it will not cause the pH value of the combination formulation to decrease to below about 10.5.

[0151] B. Premixed combination curd formulation In some embodiments, a combination formulation is provided containing an active agent and a hydroxide-containing reagent. This combination formulation may be sold as a commercially available formulation (to distributors and / or hair salons) as a premixed curling formulation containing an active agent and a hydroxide-containing reagent.

[0152] In some examples of combination formulations, the weight ratio of one or more hydroxide-containing reagents to one or more active agents in the combination formulation can range from about 10:1 to about 1:5; 5:1 to 1:5; 4:1 to 1:4; or 3:1 to 1:3. In some embodiments, the weight ratio of one or more hydroxide-containing reagents to one or more active agents ranges from about 10:1 to about 1:1; 5:1 to 1:1; 4:1 to 1:1; or 3:1 to 1:1. In some examples, the weight ratio of one or more hydroxide-containing reagents to one or more active agents in the combination formulation is about 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, or 1:5, preferably about 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, or 1:5, or within about 10% of these ratios.

[0153] Premixed formulations can be prepared prior to use and sold as commercially available products to distributors and / or hair salons. Premixed formulations are storable and are storage stable. As used herein, "stable" or "storage stable" means that at least 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, or 95% of the active agent does not degrade over a specific period of time following the formation of the formulation (e.g., at least 6 months, at least 1 year, at least 2 years, at least 3 years). Typically, premixed formulations are optionally stored at room temperature in the absence of light.

[0154] V. Reagent Kit In some embodiments, the kit for curling hair contains an active agent formulation containing an active agent.

[0155] The kit may further contain a second formulation, also referred to herein as a hydroxide-containing formulation. The hydroxide-containing reagent and the surfactant formulation are typically supplied separately, along with instructions for applying both to the hair. For example, instructions may provide instructions for producing a combined formulation by mixing the hydroxide-containing reagent and the surfactant formulation, and then applying the combined formulation to the hair. Alternatively, instructions may provide instructions for simultaneously applying the hydroxide-containing reagent to the hair while applying the surfactant formulation (but not as a premixed combined formulation). Instructions may also include instructions for selecting the desired amount of surfactant to be used, for example by specifying the volume or mass (or range thereof) of the surfactant or surfactant formulation, the desired weight ratio of the surfactant to the hydroxide-containing reagent, and / or the desired weight ratio of the first hydroxide-containing formulation to the second surfactant formulation, in order to control the level of curl imparted to the hair.

[0156] Alternatively, instructions are provided to first apply a hydroxide-containing reagent to the hair, and then apply the surfactant preparation to the hair. The instructions may specify the amount of time that can elapse after applying the hydroxide-containing reagent (i.e., in the range of about one second to about 30 minutes, more preferably within about 60 seconds) and / or the amount of surfactant preparation to be applied, in order to control the level of curl imparted to the hair. The instructions may also specify how to select the desired amount of surfactant to be used, for example by specifying the volume or mass (or range thereof) of the surfactant or surfactant preparation, the desired weight ratio of the surfactant to the hydroxide-containing reagent, and / or the desired weight ratio of the first hydroxide-containing preparation to the second surfactant preparation, in order to control the level of curl imparted to the curled hair.

[0157] In other embodiments, the kit for curling hair contains a combination formulation as described herein.

[0158] The provided instructions may also specify hair reshaping before, during, or after the application of a preparation containing one or more surfactants and / or one or more hydroxide-containing reagents. These instructions detail the use of tools, apparatus, or techniques to reshape hair into a specific shape, followed by removal or dismantling of that specific shape to achieve a desired hairstyle. For example, hair reshaping may involve rolling hair onto rollers, rods, and / or curling irons; or braiding or twisting hair; or combinations thereof. Hair reshaping may include braiding and / or twisting hair, optionally combined with or without any rollers, curling irons, curling rods, and / or other suitable hair styling instruments. Hair reshaping according to the methods described is discussed in further detail below.

[0159] The instructions also include details regarding the setting period for hair after applying one or more of the formulations discussed above, which typically ranges from about 1 to 90 minutes, preferably about 10, 20, 30, or 40 minutes. Details regarding the setting period are discussed further below.

[0160] Instructions may further include details regarding rinsing the hair after the styling period, removing any tools, devices, techniques, and / or braids used to shape the hair during the restyling step, and washing and optionally conditioning the curly hair with shampoo. Details of the above steps are discussed further below.

[0161] The kit described herein may further include shampoos, conditioners, curling irons, perming tools, gloves, applicators, or combinations thereof.

[0162] A. Hydroxide-containing preparations In some embodiments, the kit contains a hydroxide-containing reagent or a formulation thereof containing one or more hydroxide-containing reagents as described above. The hydroxide-containing formulation is typically provided in liquid form in a container. The hydroxide-containing formulation included in the kit is preferably odorless. In some embodiments, the hydroxide-containing formulation may contain a fragrance. Alternatively, the kit may further contain a fragrance that can be added to the hydroxide-containing formulation.

[0163] B. Active ingredient formulations Surfactant formulations contain one or more surfactants as described herein. Suitable surfactant-containing formulations have been discussed above. Surfactant formulations can be in any suitable form. Typically, surfactant formulations are flowable liquids at standard temperatures and pressures, such as low to medium viscosity liquids. Surfactant formulations are provided in suitable containers, depending on the form of the formulation.

[0164] In some embodiments, the surfactant formulation is provided as two or more separate components. For example, the surfactant may be provided as a dry powder in a sealed package, and the excipient may be provided in a vial or other container. Suitable containers for mixing the surfactant and excipient may be provided.

[0165] The surfactant formulation included in the kit is preferably odorless. In some embodiments, the surfactant formulation may contain a fragrance. Alternatively, the kit may further include a fragrance that can be added to the surfactant formulation.

[0166] C. Combination formulations In some embodiments, the kit contains a premixed combination formulation containing an active agent and a hydroxide-containing reagent, as described above. The combination formulation is stable for at least 6, 7, 8, 9, 10, or 11 months of storage, and optionally stable for at least 1 year or longer.

[0167] The combination formulation is typically provided in liquid form in a container. The combination formulation included in the kit is preferably odorless. In some embodiments, the combination formulation may contain a fragrance. Alternatively, the kit may further include a fragrance that can be added to the combination formulation.

[0168] VI. How to Use This article describes methods for curling hair. Curling methods can be used to give curls to various types of hair, including but not limited to naturally straight hair (e.g., Asian hair, straight Hispanic hair, or straight Caucasian hair), generally wavy hair, and hair that has been previously straightened, dyed, or bleached.

[0169] In some embodiments, the method includes controlling, selecting, or adjusting the level of curl imparted during a hair curling process or treatment (using a hydroxide-containing agent) by controlling the relative amount of the surfactant formulation to the amount of the hydroxide-containing agent formulation.

[0170] In some embodiments, the method for curling hair involves applying a first formulation containing one or more hydroxide-containing agents to the hair and applying a second formulation comprising one or more surfactants of formula I, formula II, and / or formula III to the hair, as described above. According to some embodiments, the application of the first and second formulations is performed simultaneously. For example, the first and second formulations may optionally be mixed to form a combined formulation prior to application, and the combined formulation may be applied to the hair. For example, when the hair to be curled is being styled on a stick or curling iron as needed, one or more hydroxide-containing agents may be added first to the surfactant-containing formulation, or vice versa, to form a single combined formulation, and the combined formulation may be applied to the hair to be curled.

[0171] Preferably, when the first and second formulations are applied simultaneously as a combined formulation, the amount of active agent present in the combined formulation does not lower the pH value of the combined formulation to below about 9.5, and more preferably, does not lower the pH value of the combined formulation to below about 10.5. In other embodiments, when the first and second formulations are applied simultaneously, the amount of active agent in the combined formulation results in a pH value of about 10 or greater, more preferably about 11 or greater. In some embodiments, the pH of the combination formulation is approximately 9.5 or greater, 9.6 or greater, 9.7 or greater, 9.8 or greater, 9.9 or greater, 10.0 or greater, 10.1 or greater, 10.2 or greater, 10.3 or greater, 10.4 or greater, 10.5 or greater, 10.6 or greater, 10.7 or greater, 10.8 or greater, 10.9 or greater, 11.0 or greater, 11.1 or greater, 11.2 or greater, 11.3 or greater, 11.4 or greater, 11.5 or greater, 11.6 or greater, 11.7 or greater, 11.8 or greater, 11.9 or greater, or 12.0 or greater. In some other embodiments, the pH of the combination formulation is about 9.5, 9.6, 9.7, 9.8, 9.9, 10.0, 10.1, 10.2, 10.3, 10.4, 10.5, 10.6, 10.7, 10.8, 10.9, 11.0, 11.1, 11.2, 11.3, 11.4, 11.5, 11.6, 11.7, 11.8, 11.9, or 12.0.

[0172] In some embodiments, the preferred lower end of the pH range of the formulation depends on the type of hair being curled. In a non-limiting example, when Asian hair is curled, the pH of the formulation is preferably not less than about 12. In another non-limiting example, when Caucasian hair is curled, the pH of the formulation is preferably not less than about 10. In other non-limiting examples, when Asian hair is curled, the pH of the formulation is about 11 or greater. In yet another non-limiting example, when Caucasian hair is curled, the pH of the formulation is about 10 or greater.

[0173] Preferably, the curling method is performed at room temperature, and no external heat source is applied during the curling method. In a less preferred embodiment, heating may be applied, for example, during the setting period after the hydroxide- and surfactant-containing formulation has been applied to the hair. Hair heating during the setting period is preferably maintained below about 100°C, about 90°C, about 80°C, about 70°C, about 60°C, or about 50°C. Non-limiting examples of heat sources that may be used during the setting period include, but are not limited to, hair dryers or salon hair dryers.

[0174] After applying the first and second formulations or the combination formulation, rinse the hair after the setting period. Further optionally, a second active agent formulation containing one or more active agents of Formula I, Formula II and / or Formula III may then be applied to the hair (which was previously treated in the first step).

[0175] In some embodiments, the method for curling hair involves applying a first formulation containing one or more hydroxide-containing agents to the hair, followed by applying one or more active agents of Formula I, Formula II and / or Formula III to the hair, as described above.

[0176] In other embodiments, one or more surfactants of Formula I, Formula II, and / or Formula III as described above may be added to a formulation containing one or more hydroxide-containing reagents to form a combined formulation before the formulation is applied to the hair. Typically, the surfactants are added immediately before the combined formulation is applied to the hair for a curling treatment.

[0177] The curling method described herein produces curls in the hair; conversely, applying a hydroxide-containing agent alone to the hair does not produce any curls. Furthermore, compared to treatment agents that do not contain surfactants according to Formula I, Formula II, and / or Formula III, the amount of one or more surfactants in the second formulation combined with the first formulation effectively imparts the desired level of curl to the hair while reducing damage or breakage.

[0178] A. Hair restoration The methods described herein comprise steps for hair reshaping before, during, or after applying any formulation containing one or more surfactants and / or one or more hydroxide-containing reagents.

[0179] Hair reshaping typically involves using tools, devices, or techniques to shape hair into a specific form, followed by removal or dismantling of that form to achieve a desired hairstyle. For example, hair reshaping can involve rolling hair around rollers, rods, and / or curling irons; or braiding or twisting hair; or combinations thereof.

[0180] In some embodiments, hair reshaping involves rolling or around hair on or around a curling roller, curling iron, curling stick, or other suitable hair styling instrument or tool before applying any formulation or combination thereof. The size of the rod, curling iron, curling roller, or other hair styling tool is selected to achieve the desired curl shape and size. Typically, the size of the curls in hair following the methods described herein is larger than the diameter of the rod, curling iron, curling roller, or other hair styling tool used in the reshaping step. For example, the size of the curls formed following the methods described herein can be 2 to 10 times larger than the diameter of the rod, curling iron, curling roller, or other hair styling tool used, optionally 5 to 10 times or 8 to 10 times larger.

[0181] Hair reshaping may involve hair braiding and / or twisting, optionally combined with or without any rollers, curlers, curling irons and / or other suitable hair styling instruments.

[0182] For example, braided or twisted hair will acquire curl due to the braiding or twisting. The hair can be braided or twisted as needed to adjust the size and shape of the curl imparted after applying the curling method described herein. In another example, the hair can be braided or twisted while an active agent formulation, a hydroxide-containing formulation, or a combination thereof as described herein (i.e., wet hair) is being applied to the hair, optionally without any rollers, curling irons, curling sticks, and / or other suitable hair styling instruments. The braided or twisted hair will then acquire curl due to the braiding or twisting. The hair can be braided or twisted as needed to adjust the size and shape of the curl imparted after applying the curling method described herein.

[0183] In a preferred embodiment, the hair is rolled up (e.g., rolled on a curling iron or stick), or braided or twisted, before applying a formulation containing one or more hydroxide-containing reagents and surfactants.

[0184] In non-preferred embodiments, hair may be rolled onto a curling iron or stick, or braided or twisted, after applying a formulation containing one or more hydroxide-containing reagents and surfactants. In these instances, it is preferred that the hair be rolled, braided, or twisted immediately after applying the formulation, at least about 1-15 minutes, more preferably about 1-10 minutes, and most preferably about 1-5 minutes.

[0185] B. Applying a preparation containing one or more hydroxide-containing reagents and surfactants. The surfactant and the hydroxide-containing agent may be applied to the hair simultaneously (e.g., in the form of a combination formulation), or immediately after applying the hydroxide-containing agent (where the hair is not rinsed before applying the second agent), or alternatively, immediately after applying the hydroxide-containing agent at short intervals. As used herein, "short interval" means a period of time ranging from one second to 30 minutes, one minute to 20 minutes, or five minutes to 15 minutes.

[0186] Preferably, the surfactant is applied to the hair simultaneously with one or more hydroxide-containing reagents.

[0187] The surfactant formulation can be applied once, or repeatedly once or multiple times as needed. Preferably, the amount of surfactant formulation applied is sufficient to saturate the hair. The volume of surfactant formulation applied to the hair in each application can be from about 1 to about 200 mL, depending on the length and volume of the hair.

[0188] In some other embodiments, as part of the curling process, a premixed combination formulation containing one or more hydroxide-containing reagents and one or more surfactants is applied to the hair.

[0189] In some embodiments, as part of the curling process, a first formulation containing one or more hydroxide-containing agents and a second formulation containing one or more surfactants are mixed and applied to the hair as a single combined formulation containing both types of agents. Alternatively, the first and second formulations may be applied to the hair simultaneously without a pre-mixing step.

[0190] When the formulation is applied simultaneously, the amount of surfactant used will not lower the pH of the combined formulation to below about 10, and preferably will not lower the pH of the combined formulation to below about 11, and the weight ratio of the hydroxide-containing reagent to the surfactant formulation can range from about 10:1 to about 1:5; 5:1 to 1:5; 4:1 to 1:4; or 3:1 to 1:3. In some embodiments, the weight ratio of the hydroxide-containing reagent to the surfactant formulation ranges from about 10:1 to about 1:1; 5:1 to 1:1; 4:1 to 1:1; or 3:1 to 1:1. In some instances, the weight ratio of the hydroxide-containing reagent formulation to the active agent formulation is about 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4 or 1:5, preferably about 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4 or 1:5, or within about 10% of these ratios.

[0191] When using other hydroxide-containing reagents to obtain similar results, the amount of the second formulation containing the surfactant and the concentration of the surfactant present therein can be varied as needed.

[0192] In a non-preferred embodiment, a commercially available formulation containing one or more hydroxide-containing reagents may be used, typically having a pH of about 11 to 14, representing a difference in hydroxide ion concentration of about 100-fold between the extremes of this range. In this example, the amount of surfactant may vary with the pH of the commercially available straightening formulation used, and, in the presence of a buffer, may be further adjusted according to the buffering capacity of each hydroxide-containing reagent formulation.

[0193] In some embodiments, the first and second formulations may be prepared as a single combination formulation containing one or more hydroxide-containing reagents and active agents of formula I, II and / or III in the weight ratios described above, either at the time of use or immediately before use.

[0194] In some embodiments, the first and second formulations can be prepared as a single combination formulation containing one or more hydroxide-containing reagents and active agents of formula I, II and / or III in the weight ratios described above, and stored prior to use.

[0195] The single-component formulation typically has a pH value of 10 to 14, preferably 11 to 13. According to some embodiments, when prepared as a single aqueous solution or when the first and second formulations are prepared separately and subsequently mixed to form a single-component formulation, the single-component formulation contains about 0.1 to 10 wt% of one or more hydroxide-containing reagents and about 0.05 to 10 wt% of one or more active agents.

[0196] After applying the active agent and hydroxide-containing reagent, the hair is set for a specific period of time (“styling period”), which typically ranges from about 1 to 90 minutes, preferably about 10, 20, 30 or 40 minutes.

[0197] Preferably, the method is performed at room temperature, and no external heat source is applied during the method. In a less preferred embodiment, heating may be applied, for example, during the styling period after the hydroxide-containing reagent and surfactant have been applied to the hair. Hair heating is preferably maintained below about 100°C, about 90°C, about 80°C, about 70°C, about 60°C, or about 50°C. Non-limiting examples of heat sources that may be used during the styling period include, but are not limited to, hair dryers or salon hair dryers.

[0198] C. Removing the preparation from the hair Subsequently, the preparation containing one or more hydroxide-containing reagents and surfactants, or a combination thereof, applied to the hair is rinsed off. The rinsing process typically lasts from about 0.1 to 10 minutes, preferably from about 1 to 5 minutes, and more preferably from about 3 to 5 minutes. If the hair is rinsed before removing or unwinding braids and / or twists from the curling iron, curling iron, or curling rollers, the rinsing time is preferably longer.

[0199] Optionally, remove the curled hair from the sticks / rollers / curling irons or untangle the braids or twists, and then rinse the hair. However, this process usually takes a long time. Therefore, it is often useful when only a small number of sticks, curlers, or rollers are placed in the hair. Optionally, the hair can be rinsed immediately, washed and / or conditioned with shampoo, or subjected to one or more washing cycles, and then allowed to dry (i.e., air dry, pat dry, towel dry, blow dry). Rinsing can be done with water at temperatures from about room temperature (i.e., about 23-25°C) to about 40°C.

[0200] Curly hair can be rinsed after the curling process, washed with shampoo, optionally conditioned, or subjected to one or more washing cycles. Hair can be rinsed immediately after applying the activator formulation (e.g., within 10, 15, 25, 30, 45, 60 seconds (one minute), two, three, four, or five minutes after application) and then washed with shampoo, optionally conditioned, or subjected to one or more washing cycles.

[0201] In some embodiments of the methods described herein, when a formulation containing one or more hydroxide-containing reagents and surfactants is applied simultaneously, the curly hair is rinsed, shampooed, optionally conditioned, or subjected to one or more rinsing cycles approximately 45 minutes after application. In some embodiments of the methods described herein, when a surfactant formulation is applied immediately after application of the hydroxide-containing reagent formulation (i.e., within approximately 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60 seconds (one minute), two, three, four, or five minutes), the curly hair is rinsed, shampooed, optionally conditioned, or subjected to one or more rinsing cycles approximately 15 minutes after application.

[0202] Alternatively, the hair can be rinsed, washed with shampoo, optionally conditioned, or subjected to one or more washing cycles, followed by the application of a surfactant preparation that does not require rinsing after application, and then washed with shampoo, optionally conditioned, or subjected to one or more washing cycles.

[0203] D. Optionally apply the second surfactant formulation to the hair. Optionally, while the hair is still in the roller / rod / curling iron / braid / twisted fabric, a second surfactant formulation comprising one or more surfactants of Formula I, Formula II and / or Formula III may be applied to the treated hair.

[0204] When applied, the optional second active agent formulation is allowed to remain in the hair for about 1 to 30 minutes, more preferably about 1 to 15 minutes.

[0205] Then, remove the curled hair from the curling rollers / curling iron / curling bar / braid / twisted bar and optionally wash it immediately with shampoo, rinse, condition, or undergo one or more washing cycles before letting it air dry (i.e., air dry, blot dry, towel dry, blow dry).

[0206] E. The nature of the curled hair after curling treatment Treatments using the curling methods and formulations described herein can improve hair quality (e.g., appearance (e.g., shine) and feel), increase wet and dry strength, and reduce hair breakage, even when the hair undergoes subsequent styling treatments (e.g., coloring or bleaching, or additional curling or straightening treatments (e.g., to change the curl, change the shape of the curl, or change the level of curl (e.g., tighter or looser curls))).

[0207] 1. Reduce damage / hair breakage Hair breakage is a significant problem encountered during typical hair curling treatments (e.g., perming). In this embodiment, hair breakage can be reduced by using the curling method described herein compared to standard curling treatments.

[0208] 2. Maintaining the curl In some embodiments, the curl imparted to the hair can be maintained for at least about 1 to 30 wash cycles, preferably at least about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 20, 30, 40 or 50 wash cycles.

[0209] The amount and shape of the curls imparted are influenced by the size of the curling device or technique (e.g., curler, roller, bar, woven or twisted fabric) used in combination with the application of the first and second formulations described herein.

[0210] The curl imparted to hair after the curling treatment can remain largely unchanged or substantially unchanged for a period ranging from one week to six months, for example, two weeks to four months or one month to three months. In some embodiments, the percentage of curl can remain for at least one week, two weeks, three weeks, four weeks, one month, two months, three months, four months, five months, six months, or longer. The treated hair retains its curl under conditions that would not be retained without the treatment according to the methods described herein, such as rinsing, shampooing, conditioning, or one or more rinsing cycles. As used herein, a “rinsing cycle” refers to hair that has undergone the following process: rinsing after the curling treatment described herein – shampooing – rinsing – conditioning – rinsing. Rinsing can be performed with water at a temperature from about room temperature (i.e., about 23-25°C) to about 40°C.

[0211] In some embodiments, after about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, 25, 30, 35, 40, 45, or 50 or more cleaning cycles, the percentage reduction in curl is less than about 5%, 10%, 15%, or 20% of the imparted curl. In other embodiments, after about 20-50 cleaning cycles, the percentage reduction in curl is less than about 30%, 40%, or 50% of the imparted curl. In some embodiments, after about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, 25, 30, 35, 40, 45 or 50 or more cleaning cycles (preferably two or more cleaning cycles, more preferably at least 5 cleaning cycles), and more preferably after about 5-10 cleaning cycles, the imparted curl is maintained without significant change or substantially without significant change.

[0212] As used herein, "percentage change in curl level" and "percentage change in curl" are used interchangeably and refer to the level of curl maintained over time after a curling treatment (e.g., after one or more washing cycles). A non-limiting exemplary method for determining the percentage change in curl level in hair (e.g., a hair sample) is based on the following formula: Percentage change in curl level = ( L F – L i ) / ( L i ) × 100 Where L F It is the final length of hair after one or more washing cycles or a set period of time, L i This refers to the length of the curled hair after a curling treatment. For example, the curl level (curl percentage) after treatment with surfactants and hydroxide-containing agents can maintain no significant loss of curl after washing, such as a change of approximately 0-50% in the curl level, for example, less than approximately 40%, less than approximately 30%, less than approximately 20%, less than approximately 10%, less than approximately 5%. The change in curl level can be determined after one or more washing cycles, where L... FThis corresponds to the length of the curled hair after a specific number of washing cycles (e.g., after 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, 25, 30, 35, 40, 45, or 50 or more washing cycles). Alternatively, the level of curl imparted after the curling method and the corresponding curl retention after one or more washing cycles can be assessed by visual inspection. Visual inspection is particularly useful when the curled hair has natural curl or was previously curled. Visual inspection can also be used to determine changes in curl characteristics, such as the shape and / or tightness of the curl.

[0213] F. Optional subsequent straightening or curling treatment for changing the level of curl. After performing the hair curling method described herein, the level of curl can be altered by one or more additional curling treatments according to the same method described herein. For example, the curling method can be repeatedly applied to the hair to selectively change the level of curl over a period of time (e.g., daily, weekly, or monthly, or other suitable time intervals). In a non-limiting example, the curling method can be repeated 10, 20, 30, 40, 50, or more times at the aforementioned time intervals. Optionally, after using the hair curling method described herein, the hair can be treated with a straightening process to straighten it immediately thereafter (i.e., within 24 hours of the curling treatment). Further optionally, a subsequent curling method can be applied within 24 hours to curl the hair. This allows people to adjust and change the level of curl in their hair as needed without damaging the hair.

[0214] G. Exemplary usage method In a non-limiting embodiment of the method described herein, hair is wrapped / rolled around one or more curling irons or perming tools. A combination formulation containing one or more hydroxide-containing reagents and surfactants is then applied to the hair. In some embodiments, the combination formulation is applied simultaneously with (but not subsequently) wrapping or rolling the hair around the curling irons or perming tools. Typically, one or more sections of hair are wrapped or rolled around one or more perming tools (e.g., irons). Typically, more than one perming tool or iron is used to provide multiple curls in the hair, typically on all the hair in the head.

[0215] Optionally, wash your hair with shampoo or clarifying shampoo and towel dry it before wrapping / rolling it around the curling iron or curling tool.

[0216] The amount of the preparation applied is preferably enough to saturate the hair on the curling iron or curling tool. The hair is then set for a given period of time (“setting period”). It is preferable that no heating is required during the setting period. The setting period can be approximately 1 to 90 minutes after application of the preparation, preferably approximately 10, 20, 30, or 40 minutes, and even more preferably 30 minutes.

[0217] After the setting period, for example, after 30 minutes, rinse the hair and then remove the curling iron or curling tools from the hair. Alternatively, after the setting period, remove the curling iron or curling tools from the hair and then rinse the hair. Rinsed hair is usually then shampooed and optionally conditioned.

[0218] Example Example 1: Curly hair in Asians Composition of Formulations 1 and 2: Formulation 1 It contains 2 wt% NaOH and 2 wt% diaminopropyl diethylene glycol dimaleate, with the remainder of the formulation consisting of water.

[0219] Formulation 2 It contains 4 wt% diaminopropyl diethylene glycol dimaleate, and the remainder of the formulation consists of water.

[0220] Curling procedure: Prepare immediately before use Formulation 1 Apply the product to an Asian hair sample using the curling rollers and leave it for 20 minutes. Then rinse the hair sample thoroughly with room temperature water for 3 minutes, and then pat dry with a paper towel. Formulation 2 Add to the hair sample and let stand for 20 minutes. Then rinse the hair sample, remove it from the roller, wash and condition with shampoo, and let it air dry.

[0221] Curling result: Compared to the hair before treatment, the hair retains its curl and exhibits a better condition, such as increased smoothness and shine.

[0222] After 20 washing cycles including shampooing and conditioning, curl retention was tested. After 20 washing cycles, curl retention was almost identical to that after the initial treatment.

[0223] Example 2: Curly hair in Asians Composition of Formulations 1 and 2: Formulation 1 It contains 2 wt% NaOH, and the remainder of the preparation consists of water.

[0224] Formulation 2 It contains 4 wt% diaminopropyl diethylene glycol dimaleate, and the remainder of the formulation consists of water.

[0225] Curling procedure: Two Asian hair samples were rolled into a perming roller and then... Formulation 1Process each sample for 20 minutes. Then rinse both hair samples for 3 minutes and blot dry with a paper towel. Then use one sample... Formulation 2 One sample was treated for 20 minutes, and another sample was treated with a 5 wt% acetic acid aqueous solution for 20 minutes. Both samples were then rinsed, removed from the curling rollers, washed and conditioned with shampoo, and allowed to air dry.

[0226] Curling result: Compared to the sample treated according to the conditions listed in Example 1 (above), with Formulation 2 The neutralized hair samples showed that the curl was retained, but they were in a worse condition than before the treatment and were in a significantly inferior state.

[0227] The sample neutralized with acetic acid solution did not retain its curl and was visibly damaged and in a more favorable position than... Formulation 2 The neutralized sample is in a worse state.

[0228] Example 3: The curliness of Caucasian hair Composition of Formulations 1 and 2: Formulation 1 It contains 2 wt% NaOH and 4 wt% diaminopropyl diethylene glycol dimaleate, with the remainder of the formulation consisting of water.

[0229] Formulation 2 It contains 4 wt% diaminopropyl diethylene glycol dimaleate, and the remainder of the formulation consists of water.

[0230] Curling procedure: Prepare immediately before use Formulation 1 Apply the product to Caucasian hair using curling rollers and leave it on for 20 minutes. Then rinse the hair sample thoroughly in room temperature water for 3 minutes and pat dry with a paper towel. Formulation 2 Add to the hair sample and let stand for 20 minutes. Then rinse the hair sample, remove it from the curling rollers, wash and condition with shampoo, and let it air dry.

[0231] Curling result: Compared to the untreated hair, the treated hair retained its curl and exhibited better condition, such as increased smoothness and shine. Curl retention was tested after 10 washing cycles including shampooing and conditioning. After 10 washing cycles, the curl retention was almost identical to that after the initial treatment.

[0232] Example 4: The curliness of Caucasian hair Composition of Formulations 1 and 2: Formulation 1It contains 2.6 wt% NaOH and 4 wt% diaminopropyl diethylene glycol dimaleate, with the remainder of the formulation consisting of water.

[0233] Formulation 2 It contains 3 wt% diaminopropyl diethylene glycol dimaleate, and the remainder of the formulation consists of water and is in the form of a cream.

[0234] Curling procedure: Prepare immediately before use Formulation 1 Apply the product to Caucasian hair using curling rollers and leave it on for 40 minutes. Then rinse the hair sample thoroughly in room temperature water for 3 minutes and pat dry with a paper towel. Formulation 2 Apply to a hair sample and leave for 10 minutes. Then rinse the hair sample, remove it from the curling rollers, wash and condition with shampoo, and let it air dry.

[0235] Curling result: Compared to the untreated hair, the treated hair retained its curl and exhibited better condition, such as increased smoothness and shine. Curl retention was tested after 10 washing cycles including shampooing and conditioning. After 10 washing cycles, the curl retention was almost identical to that after the initial treatment.

[0236] Example 5: Curly hair in Asians Composition of Formulations 1 and 2: Formulation 1 It contains 2.6 wt% NaOH and 2 wt% diaminopropyl diethylene glycol dimaleate, with the remainder of the formulation consisting of water.

[0237] Formulation 2 It contains 3 wt% diaminopropyl diethylene glycol dimaleate, and the remainder of the formulation consists of water and is in the form of a cream.

[0238] Curling procedure: Prepare immediately before use Formulation 1 Apply the product to Asian hair using curling rollers and leave it on for 40 minutes. Then rinse the hair sample thoroughly in room temperature water for 3 minutes and pat dry with a paper towel. Formulation 2 Apply to hair and leave for 10 minutes. Then rinse the hair sample, remove from the roller, wash and condition with shampoo, and let it air dry.

[0239] Curling result: Compared to the untreated hair, the treated hair retained its curl and exhibited better condition, such as increased smoothness and shine. Curl retention was tested after 10 washing cycles including shampooing and conditioning. After 10 washing cycles, the curl retention was almost identical to that after the initial treatment.

[0240] Example 6: The curliness of Caucasian hair Composition of Formulation 1: Formulation 1 It contains 6.6 wt% NaOH and 1.25 wt% diaminopropyl diethylene glycol dimaleate, with the remainder of the formulation consisting of water.

[0241] Curling procedure: Prepare immediately before use Formulation 1 Apply the product to Caucasian hair in the perm rollers and leave it for 40 minutes. Then rinse the hair sample, remove it from the perm rollers, wash and condition it with shampoo, and let it air dry.

[0242] Curling result: Compared to the untreated hair, the treated hair retained its curl and exhibited better condition, such as increased smoothness and shine. Curl retention was tested after 10 washing cycles including shampooing and conditioning. After 10 washing cycles, the curl retention was almost identical to that after the initial treatment.

[0243] Example 7: Curly hair in Asians Composition of Formulation 1: Formulation 1 It contains 6.6 wt% NaOH and 0.77 wt% maleic acid, with the remainder of the formulation consisting of water.

[0244] Curling procedure: Prepare immediately before use Formulation 1 Apply the product to Asian hair in the perm rollers and leave it for 30 minutes. Then rinse the hair sample, remove it from the rollers, wash and condition it with shampoo, and let it air dry.

[0245] Curling result: Compared to the untreated hair, the treated hair retained its curl and exhibited better condition, such as increased smoothness and shine. Curl retention was tested after 10 washing cycles including shampooing and conditioning. After 10 washing cycles, the curl retention was almost identical to that after the initial treatment.

[0246] Example 8: The curliness of Caucasian hair Composition of Formulation 1: Formulation 1 It contains 6.6 wt% NaOH and 0.77 wt% maleic acid, with the remainder of the formulation consisting of water.

[0247] Curling procedure: Prepare immediately before use Formulation 1 Apply the product to Asian hair in the perm rollers and leave it for 30 minutes. Then rinse the hair sample, remove it from the rollers, wash and condition it with shampoo, and let it air dry.

[0248] Curling result: Compared to the untreated hair, the treated hair retained its curl and exhibited better condition, such as increased smoothness and shine. Curl retention was tested after 10 washing cycles including shampooing and conditioning. After 10 washing cycles, the curl retention was almost identical to that after the initial treatment.

[0249] Example 9: The curliness of Caucasian hair Composition of Formulation 1: Formulation 1 It contains 6.6 wt% NaOH and 0.7 wt% methacrylic acid, with the remainder of the formulation consisting of water.

[0250] Curling procedure: Prepare immediately before use Formulation 1 Apply the product to Asian hair in the perm rollers and leave it for 30 minutes. Then rinse the hair sample, remove it from the rollers, wash and condition it with shampoo, and let it air dry.

[0251] Curling result: Compared to the untreated hair, the treated hair retained its curl and exhibited better condition, such as increased smoothness and shine. Curl retention was tested after 10 washing cycles including shampooing and conditioning. After 10 washing cycles, the curl retention was almost identical to that after the initial treatment.

[0252] Example 10: The curliness of Caucasian hair Composition of Formulation 1: Formulation 1 It contains 6.6 wt% NaOH and 0.7 wt% methacrylic acid, with the remainder of the formulation consisting of water.

[0253] Curling procedure: Prepare immediately before use Formulation 1Apply the product to Asian hair in the perm rollers and leave it for 30 minutes. Then rinse the hair sample, remove it from the rollers, wash and condition it with shampoo, and let it air dry.

[0254] Curling result: Compared to the untreated hair, the treated hair retained its curl and exhibited better condition, such as increased smoothness and shine. Curl retention was tested after 10 washing cycles including shampooing and conditioning. After 10 washing cycles, the curl retention was almost identical to that after the initial treatment.

[0255] Example 11: Curl in Caucasian hair without surfactants Composition of Formulation 1: Formulation 1 It contains 6.6 wt% NaOH and 0.7 wt% lactic acid, with the remainder of the formulation consisting of water.

[0256] Curling procedure: Prepare immediately before use Formulation 1 Apply the product to Asian hair in the perm rollers and leave it for 30 minutes. Then rinse the hair sample, remove it from the rollers, wash and condition it with shampoo, and let it air dry.

[0257] Curling result: After one wash, the treated hair did not retain any noticeable curl, and after three wash cycles, the curl was even less than before the treatment. Compared to before the treatment, the hair was flat, with increased frizz and breakage, and a poor feel.

Claims

1. A method for curling hair, comprising the following steps: (a) An application of a preparation to hair, comprising: One or more hydroxide-containing reagents, wherein the one or more hydroxide-containing reagents are selected from the group consisting of alkali metal hydroxides, guanidine hydroxides, and ammonium hydroxides; and Surfactant of Formula I: Formula I in A, B, C, and D are reactive moieties capable of reacting with thiol groups to form covalent bonds and containing one or more charges, wherein each of A, B, C, and / or D independently contains a moieties selected from the group consisting of: vinyl sulfone, acrylate ion, methacrylate ion, styrene group, acrylamide group, methacrylamide group, maleate ion, fumarate ion, and itaconic acid ion. R is a linking group containing two or more charges, wherein the charges are opposite to those on the reactive moiety, where n = 1, and R is not a polymer. The total charge is 0. The linking group is selected from the group consisting of: alkoxy, ether, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, heteroaryl, and amine; wherein the linking group is optionally independently substituted by one or more substituents, which may be the same or different, including hydrogen, halogen, cyano, alkoxy, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, heteroaryl, amine, hydroxy, formyl, acyl, carboxylic acid, -C(O)R 1 -C(O)OR 1 Carboxyl group, primary amide, secondary amide, -C(O)NR 1 R 2 -NR 1 R 2 -NR 1 S(O)2R 2 -NR 1 C(O)R 2 -S(O)2R 2 -SR 1 and -S(O)2NR 1 R 2 , sulfinyl group and sulfonyl group; wherein R 1 and R 2 Each can be independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocycloalkyl, and heteroaryl; wherein R 1 and R 2 Each may optionally be independently substituted by one or more substituents selected from the group consisting of: halogen, hydroxyl, cyano, nitro, amino, alkylamino, dialkylamino, alkyl optionally substituted with one or more halogens, alkoxy or aryloxy groups, aryl optionally substituted with one or more halogens, alkoxy or alkyl or trihaloalkyl groups, heterocyclic alkyl optionally substituted with aryl or heteroaryl or =O groups, or alkyl optionally substituted with hydroxyl groups, cycloalkyl optionally substituted with hydroxyl groups, heteroaryl optionally substituted with one or more halogens, alkoxy or alkyl or trihaloalkyl groups, haloalkyl, hydroxyalkyl, carboxyl, alkoxy, aryloxy, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl and dialkylaminocarbonyl; and The reactive portion is ionically bonded to the linking group; Each occurrence of p, q, r, and s is independently between 0 and 25, and the sum of p + q + r + s is equal to or greater than 2; or, One or more active agents selected from the group consisting of: , , and , and its simple salts; The formulation has a pH value of 10 or greater and contains less than 1 wt% of a thiol-containing reagent; The formulation comprises 0.1 to 10 wt% of the one or more hydroxide-containing reagents and 0.05 to 10 wt% of the active agent; The formulation described herein does not contain thiol-based reducing agents, such as thioglycolic acid, thiolactic acid, thioglycerol, or mercaptopropionic acid or its salts, or thioglycerol or its derivatives; and does not contain other types of reducing agents, such as sodium bisulfite; and The hydroxide-containing reagent and the surfactant may be applied as a combined formulation or as separate formulations applied simultaneously. (b) Reshaping the hair, wherein steps (a) and (b) effectively curl the hair; and optionally... (c) Applying a second surfactant formulation to the hair, comprising a second surfactant, wherein the second surfactant is Or its simple salt, Or its simple salt, Or its simple salt, Or its simple salt, ,or or mixtures thereof; Step (c) occurs after step (b).

2. The method according to claim 1, wherein the surfactant is: ,or ； Alternatively, the active agent may be selected from the group consisting of: , , and , And its simple salts.

3. The method according to claim 1, wherein the method comprises steps (a) and (b); or the method comprises steps (a), (b) and (c).

4. The method according to claim 1, wherein the formulation contains less than 0.1 wt% of a thiol-containing reagent.

5. The method of claim 1, wherein step (b) occurs before step (a).

6. The method of claim 1, wherein the formulation is a combination formulation, and wherein prior to step (a), a first formulation comprising one or more hydroxide-containing reagents and a second formulation comprising the active agent are mixed to form the combination formulation, wherein the combination formulation has a pH of 10 or greater.

7. The method according to any one of claims 1 to 6, wherein the weight ratio of the one or more hydroxide-containing reagents to the activator is in the range of 5:1 to 1:

5.

8. The method according to any one of claims 1 to 5, wherein after steps (a) and (b), the curling is maintained for at least 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, 25, 30, 35, 40, 45 or 50 cleaning cycles.

9. The method according to claim 1, wherein the one or more hydroxide-containing reagents are alkali metal hydroxides, and wherein the alkali metal hydroxides are selected from the group consisting of sodium hydroxide, lithium hydroxide, and potassium hydroxide.

10. The method according to any one of claims 1 to 6, wherein step (b) comprises winding the hair onto a roller, bar, or curling iron or a combination thereof, weaving or twisting the hair; or a combination thereof.

11. The method of claim 1, wherein the second activator formulation comprises 0.1 wt% to 5 wt% of the second activator.

12. A combination formulation comprising: One or more hydroxide-containing reagents, and Surfactant of Formula I: Formula I in A, B, C, and D are reactive moieties capable of reacting with thiol groups to form covalent bonds and containing one or more charges, wherein each of A, B, C, and / or D independently contains a moieties selected from the group consisting of: vinyl sulfone, acrylate ion, methacrylate ion, styrene group, acrylamide group, methacrylamide group, maleate ion, fumarate ion, and itaconic acid ion. R is a linking group containing two or more charges, wherein the charges are opposite to those on the reactive moiety, where n = 1, and R is not a polymer. The total charge is 0. The linking group is selected from the group consisting of: alkoxy, ether, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, heteroaryl, and amine; wherein the linking group is optionally independently substituted by one or more substituents, which may be the same or different, including hydrogen, halogen, cyano, alkoxy, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, heteroaryl, amine, hydroxy, formyl, acyl, carboxylic acid, -C(O)R 1 -C(O)OR 1 Carboxyl group, primary amide, secondary amide, -C(O)NR 1 R 2 -NR 1 R 2 -NR 1 S(O)2R 2 -NR 1 C(O)R 2 -S(O)2R 2 -SR 1 and -S(O)2NR 1 R 2 , sulfinyl group and sulfonyl group; wherein R 1 and R 2 Each can be independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocycloalkyl, and heteroaryl; wherein R 1 and R 2 Each may optionally be independently substituted by one or more substituents selected from the group consisting of: halogen, hydroxyl, cyano, nitro, amino, alkylamino, dialkylamino, alkyl optionally substituted with one or more halogens, alkoxy or aryloxy groups, aryl optionally substituted with one or more halogens, alkoxy or alkyl or trihaloalkyl groups, heterocyclic alkyl optionally substituted with aryl or heteroaryl or =O groups, or alkyl optionally substituted with hydroxyl groups, cycloalkyl optionally substituted with hydroxyl groups, heteroaryl optionally substituted with one or more halogens, alkoxy or alkyl or trihaloalkyl groups, haloalkyl, hydroxyalkyl, carboxyl, alkoxy, aryloxy, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl and dialkylaminocarbonyl; and The reactive portion is ionically bonded to the linking group; Each occurrence of p, q, r, and s is independent and ranges from 0 to 25, and the sum of p + q + r + s is equal to or greater than 2; Alternatively, one or more active agents selected from the group consisting of: , , and , and its simple salt, The one or more hydroxide-containing reagents mentioned above are selected from the group consisting of: alkali metal hydroxides, guanidine hydroxides, and ammonium hydroxides; The combination formulations described herein do not contain thiol-based reducing agents, such as thioglycolic acid, thiolactic acid, thioglycerol, or mercaptopropionic acid or its salts, or thioglycerol or its derivatives; and do not contain other types of reducing agents, such as sodium bisulfite. The combined formulation has a pH of 10 or greater and contains less than 1 wt% of a thiol-containing reagent; and The formulation comprises 0.1 to 10 wt% of the one or more hydroxide-containing reagents and 0.05 to 10 wt% of the active agent.

13. The combination formulation according to claim 12, wherein the active agent is: ,or ； Alternatively, the active agent may be selected from the group consisting of: , , and , And its simple salts.

14. The combination formulation according to claim 12, wherein the weight ratio of the one or more hydroxide-containing reagents to the active agent is in the range of 5:1 to 1:

5.

15. A reagent kit comprising: (a) A combination formulation comprising one or more hydroxide-containing reagents, and Surfactant of Formula I: Formula I in A, B, C, and D are reactive moieties capable of reacting with thiol groups to form covalent bonds and containing one or more charges, wherein each of A, B, C, and / or D independently contains a moieties selected from the group consisting of: vinyl sulfone, acrylate ion, methacrylate ion, styrene group, acrylamide group, methacrylamide group, maleate ion, fumarate ion, and itaconic acid ion. R is a linking group containing two or more charges, wherein the charges are opposite to those on the reactive moiety, where n = 1, and R is not a polymer. The total charge is 0. The linking group is selected from the group consisting of: alkoxy, ether, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, heteroaryl, and amine; wherein the linking group is optionally independently substituted by one or more substituents, which may be the same or different, including hydrogen, halogen, cyano, alkoxy, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, heteroaryl, amine, hydroxy, formyl, acyl, carboxylic acid, -C(O)R 1 -C(O)OR 1 Carboxyl group, primary amide, secondary amide, -C(O)NR 1 R 2 -NR 1 R 2 -NR 1 S(O)2R 2 -NR 1 C(O)R 2 -S(O)2R 2 -SR 1 and -S(O)2NR 1 R 2 , sulfinyl group and sulfonyl group; wherein R 1 and R 2 Each can be independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocycloalkyl, and heteroaryl; wherein R 1 and R 2 Each may optionally be independently substituted by one or more substituents selected from the group consisting of: halogen, hydroxyl, cyano, nitro, amino, alkylamino, dialkylamino, alkyl optionally substituted with one or more halogens, alkoxy or aryloxy groups, aryl optionally substituted with one or more halogens, alkoxy or alkyl or trihaloalkyl groups, heterocyclic alkyl optionally substituted with aryl or heteroaryl or =O groups, or alkyl optionally substituted with hydroxyl groups, cycloalkyl optionally substituted with hydroxyl groups, heteroaryl optionally substituted with one or more halogens, alkoxy or alkyl or trihaloalkyl groups, haloalkyl, hydroxyalkyl, carboxyl, alkoxy, aryloxy, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl and dialkylaminocarbonyl; and The reactive portion is ionically bonded to the linking group; Each occurrence of p, q, r, and s is independent and ranges from 0 to 25, and the sum of p + q + r + s is equal to or greater than 2; Alternatively, one or more active agents selected from the group consisting of: , , and , and its simple salt, The one or more hydroxide-containing reagents mentioned above are selected from the group consisting of: alkali metal hydroxides, guanidine hydroxides, and ammonium hydroxides; The combination formulations described herein do not contain thiol-based reducing agents, such as thioglycolic acid, thiolactic acid, thioglycerol, or mercaptopropionic acid or its salts, or thioglycerol or its derivatives; and do not contain other types of reducing agents, such as sodium bisulfite. The combined formulation has a pH value of 10 or greater and contains less than 1 wt% of a thiol-containing reagent; The formulation comprises 0.1 to 10 wt% of the one or more hydroxide-containing reagents and 0.05 to 10 wt% of the active agent; and (b) Instructions for curling hair.

16. A reagent kit comprising: (a) A first formulation comprising one or more hydroxide-containing reagents, wherein said one or more hydroxide-containing reagents are selected from the group consisting of alkali metal hydroxides, guanidine hydroxides, and ammonium hydroxides, wherein the first formulation is free of thiol-based reducing agents, such as thioglycolic acid, thiolactic acid, thioglycerol, or mercaptopropionic acid or its salts, or thioglycerol or its derivatives; and free of other types of reducing agents, such as sodium bisulfite; and (b) A second formulation comprising an active agent of formula I: Formula I in A, B, C, and D are reactive moieties capable of reacting with thiol groups to form covalent bonds and containing one or more charges, wherein each of A, B, C, and / or D independently contains a moieties selected from the group consisting of: vinyl sulfone, acrylate ion, methacrylate ion, styrene group, acrylamide group, methacrylamide group, maleate ion, fumarate ion, and itaconic acid ion. R is a linking group containing two or more charges, wherein the charges are opposite to those on the reactive moiety, where n = 1, and R is not a polymer. The total charge is 0. The linking group is selected from the group consisting of: alkoxy, ether, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, heteroaryl, and amine; wherein the linking group is optionally independently substituted by one or more substituents, which may be the same or different, including hydrogen, halogen, cyano, alkoxy, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, heteroaryl, amine, hydroxy, formyl, acyl, carboxylic acid, -C(O)R 1 -C(O)OR 1 Carboxyl group, primary amide, secondary amide, -C(O)NR 1 R 2 -NR 1 R 2 -NR 1 S(O)2R 2 -NR 1 C(O)R 2 -S(O)2R 2 -SR 1 and -S(O)2NR 1 R 2 , sulfinyl group and sulfonyl group; wherein R 1 and R 2 Each can be independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocycloalkyl, and heteroaryl; wherein R 1 and R 2 Each may optionally be independently substituted by one or more substituents selected from the group consisting of: halogen, hydroxyl, cyano, nitro, amino, alkylamino, dialkylamino, alkyl optionally substituted with one or more halogens, alkoxy or aryloxy groups, aryl optionally substituted with one or more halogens, alkoxy or alkyl or trihaloalkyl groups, heterocyclic alkyl optionally substituted with aryl or heteroaryl or =O groups, or alkyl optionally substituted with hydroxyl groups, cycloalkyl optionally substituted with hydroxyl groups, heteroaryl optionally substituted with one or more halogens, alkoxy or alkyl or trihaloalkyl groups, haloalkyl, hydroxyalkyl, carboxyl, alkoxy, aryloxy, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl and dialkylaminocarbonyl; and The reactive portion is ionically bonded to the linking group; Each occurrence of p, q, r, and s is independent and ranges from 0 to 25, and the sum of p + q + r + s is equal to or greater than 2; Alternatively, one or more active agents selected from the group consisting of: , , and , and its simple salts; The first and second formulations contain less than 1 wt% of a thiol-containing reagent; and (c) Instructions for curling hair.

17. The kit according to claim 15 or 16, further comprising shampoo, conditioner, curling iron, perming tool, perfume, gloves, applicator, or a combination thereof.

18. The kit according to claim 15 or 16, wherein the weight ratio of the one or more hydroxide-containing reagents to the active agent is in the range of 5:1 to 1:5.

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