Decolorizing media containing phenalenone

Abstract

The present invention relates to a decolorizing medium comprising at least one phenalenone capable of generating singlet oxygen, at least one persulfate, at least one alkalizing agent, and at least one hydrogen peroxide source, and a method for decolorizing hair using the decolorizing medium.

Description

[Technical Field]

[0001] The present invention relates to a decolorizing medium comprising at least one photosensitizer capable of generating singlet oxygen, at least one persulfate, at least one alkalizing agent, and at least one hydrogen peroxide source, and a method for decolorizing hair using the decolorizing medium. [Background technology]

[0002] Hair bleaching is an established technique in the hair cosmetics industry. Hair bleaching involves applying an oxidizing agent to the hair for a period of time that is effective in achieving the desired lighter hair color. Typically, a hydrogen peroxide solution with a concentration ranging from 1 to 12% by weight is used as the oxidizing agent. Hydrogen peroxide is applied to the hair under alkaline pH conditions, gradually lightening the hair color by oxidizing the melanin that gives the hair its color.

[0003] To enhance the lightening efficiency of peroxide solutions, persulfate formulations can be incorporated as "boosters." Sodium persulfate, potassium persulfate, or ammonium persulfate are supplied in powder form and mixed with the hydrogen peroxide solution before use. The mixed product is then applied to the hair for a period of time effective in achieving the desired lighter hair shade.

[0004] Currently, hair bleach is most commonly seen in the form of a two-component kit. One component comprises an aqueous hydrogen peroxide composition, and the second component comprises a powder bleaching composition containing a persulfate and an alkaline agent, which act as accelerators for the bleaching process when the two components are combined. This powder bleaching composition may be used alone or in combination with the aqueous hydrogen peroxide composition to bleach hair. When hydrogen peroxide and persulfate are combined, they are highly reactive, forming nascent oxygen in addition to hydrogen and sodium sulfide. Nascent oxygen greatly accelerates the oxidation and bleaching of melanin in the hair.

[0005] Unfortunately, the process of bleaching hair not only lightens the hair but also causes a perceived change in hair color tone, which is often described as discoloration or blastiness, resulting in the hair appearing more orange compared to untreated hair of similar lightness.

[0006] Hair softness is a highly desirable attribute and contributes significantly to the overall feel and appearance of healthy, well-cared-for hair. Soft hair is generally easy to manage, easy to style, and feels pleasant to the touch, improving the aesthetics and comfort of the individual. Hair softness is often an indicator of sufficient hydration and proper conditioning, showing that the hair cuticles are smooth and regularly aligned, reducing friction and tangling. This characteristic is particularly beneficial because it reduces breakage and split ends, and can make hair stronger and more resilient over time.

[0007] US9,895,299B2 describes a process for decolorizing or dyeing keratin fibers, comprising the steps of applying a composition containing one or more chemical oxidizing agents and irradiating the hair with UV visible light.

[0008] US4,792,341 discloses a method and apparatus for artificially bleaching or lightening hair by exposing it to strong radiation from artificial light.

[0009] EP451261B1 describes a method for bleaching hair under the influence of light. In this method, 10 to 120 g of a drug, which is either a solution, emulsion, or gel and contains at least one photosensitizer and a compound capable of providing hydrogen radicals, is applied to the hair and left on the hair for up to 80 minutes. The hair is then exposed to visible light and / or ultraviolet light.

[0010] None of the prior art references disclose the use of a photosensitizer that generates singlet oxygen for hair bleaching.

[0011] There is a need to provide stylists and customers with a bleaching medium that effectively bleaches hair while reducing the level of color fading and maintaining a level of damage equivalent to or lower than conventional bleaching techniques.

[0012] Therefore, the object of the present invention is to provide a decolorizing medium that effectively decolorizes hair while reducing the level of color fading and maintaining a level of damage equivalent to or lower than that of conventional decolorizing techniques. [Overview of the project]

[0013] Surprisingly, adding at least one photosensitizer capable of generating singlet oxygen to a decolorizing medium containing at least one persulfate, at least one alkalizing agent, and at least one hydrogen peroxide source can effectively formulate a hair decolorizing medium that decolorizes hair effectively while contributing to hair softness, thereby reducing or maintaining the level of hair damage caused by conventional decolorizing techniques, as supported by lower combability.

[0014] Therefore, in one aspect, the present invention relates to a decolorizing medium. This decolorizing medium is (A) at least one photosensitizer capable of generating singlet oxygen which is at least one phenalenone, (B) at least one persulfate, (C) at least one alkalizing agent, (E) comprising at least one hydrogen peroxide source.

[0015] In another aspect, the present invention relates to a method for bleaching hair, the method being at least a) A step of applying a decolorizing medium to the hair to obtain coated hair, b) exposing the coated hair to electromagnetic radiation having wavelengths within the range of 230 nm or more and 1000 nm or less, preferably within the range of 380 nm or more and 1000 nm or less, more preferably within the range of 380 nm or more and 780 nm or less, even more preferably within the range of 380 nm or more and 490 nm or less, and most preferably within the range of 390 nm or more and 430 nm or less; c) rinsing the decolorizing medium from the coated hair; d) optionally, drying the decolorized hair.

[0016] In another aspect, the present invention relates to the use of at least one phenalenone for decolorizing hair by generating singlet oxygen.

[0017] In another aspect, the present invention relates to a phenalenone substituted at the 2-position of the phenalenone ring with one organic moiety. This organic moiety is substituted with at least one positively charged nitrogen atom and / or at least one neutral protonatable nitrogen atom, and at least one negatively charged functional group.

[0018] Other objects, advantages and uses of the present invention will become apparent to those skilled in the art from the following detailed description.

Best Mode for Carrying Out the Invention

[0019] The following detailed description is merely exemplary in nature and is not intended to limit the present invention or its applications and uses. Further, there is no intention to be bound by any theory presented in the foregoing technical field, background art, summary, or the following detailed description.

[0020] As used herein, the terms “to include,” “to include,” and “to consist of” are synonymous with “to include,” “to contain,” or “to contain,” and are inclusive or unrestricted, and do not exclude any additional, undescribed members, elements, or method steps. As used herein, the terms “to include,” “to contain,” and “to consist of” are understood to include “to consist of,” “to comprise,” and “to comprise.”

[0021] Furthermore, terms such as “(a)”, “(b)”, “(c)”, and “(d)” in the specification and claims are used to distinguish similar elements and are not necessarily used to describe a sequence or chronological order. The terms used in this manner are interchangeable under appropriate circumstances, and it is understood that embodiments of the subject matter described herein may operate in sequences other than those described or illustrated herein. Where terms such as “(A)”, “(B)”, “(C)” or “(a)”, “(b)”, “(c)”, “(d)”, “(i)”, and “(ii)” relate to a method, use, or steps of an assay, there is no consistency in time or time intervals between steps. That is, unless otherwise indicated in this application as described above or below in this specification, steps may be performed simultaneously, or there may be time intervals of seconds, minutes, hours, days, weeks, months, or even years between such steps.

[0022] The term "approximately" should be understood to mean a range of ±10% when used in relation to weight ratios or weight percentages. For example, if the weight percentage of a compound is approximately 1%, it means that the weight percentage is within the range of 0.9 to 1.1%. For example, if the weight percentage of a compound is approximately 2.5%, it means that the weight percentage is within the range of 2.25 to 2.75%.

[0023] The following sections provide more detailed definitions of various aspects of the subject matter. Each of these defined aspects may be combined with other aspects unless explicitly stated otherwise. In particular, any feature shown as desirable or advantageous may be combined with any other feature shown as desirable or advantageous.

[0024] Throughout this specification, when we refer to "one embodiment" or "preferred embodiment," we mean that a particular feature, structure, or characteristic described in relation to that embodiment is included in at least one embodiment of the present invention. Therefore, where the phrases "in one embodiment" or "in a preferred embodiment" appear in various places throughout this specification, they may not all refer to the same embodiment, but rather to different embodiments of the present invention. Furthermore, features, structures, or characteristics may be combined in any suitable manner in one or more embodiments, as will be apparent to those skilled in the art from this disclosure. Moreover, some embodiments described herein include some features included in other embodiments, while others do not; however, combinations of features from different embodiments are within the scope of the subject matter and form different embodiments, as will be understood to those skilled in the art. For example, in the appended claims, any of the claimed embodiments may be used in any combination.

[0025] Furthermore, the ranges defined throughout this specification include extreme values; that is, the range from 1 to 10 implies that both 1 and 10 are included within that range. To avoid any doubt, the applicant shall have rights to any equivalent in accordance with applicable law.

[0026] For the purposes of the present invention, "weight percent" or "wt.%" as used herein refers to the total weight of the decolorizing medium. Furthermore, as described herein, the sum of the wt.% of all compounds in each component is 100 wt.%.

[0027] All documents cited herein, including cross-references or related patents or applications, are incorporated herein by reference in their entirety unless expressly excluded or limited. No citation of any document constitutes prior art with respect to any invention disclosed or claimed herein, nor does it authorize teaching, suggesting, or disclosing such invention, either by itself or in combination with other references. Furthermore, in the event of any conflict between the meaning or definition of a term in this document and the meaning or definition of the same term in a document incorporated by reference, the meaning or definition assigned to the term herein shall prevail.

[0028] The preceding text of this specification and the measurement techniques described herein are well known to those skilled in the art and therefore do not limit the present invention.

[0029] "User" or "customer" means the person who prepares the hair treatment composition. The user may be, for example, a professional hairstylist working in a salon, and may be different from or the same person to whom the composition is applied. Mixing may be done in a bowl, in a bottle, or via a mixer placed between the place where the individual compositions are stored and the place where they are dispensed for use. Two-component decolorizing media are the most commonly seen on the market, but others use three or more components.

[0030] "Lift (or lifting power)" refers to the amount of improvement in hair lightness resulting from the decolorization of natural hair pigment melanin using the decolorizing medium of the present invention. The amount of lift provided by different hair treatment compositions can be compared by measuring the change in color obtained after application of the composition to a sample of natural human black hair (e.g., black hair of a Chinese individual). The change in color can be measured using well-known parameters such as L*a*b* values. A certain composition yields an L* value or so-called dL* value (L* final -L* initialIf the value (given by) is higher than that of other compositions, it can be said that it gives a higher lift than another composition. The naming of Level 2 (as used herein synonymously with “demi-permanent” or “tone-on-tone”) and Level 3 (as used herein synonymously with “permanent”) is commonly used in the hair color industry to distinguish between medium-lift and high-lift formulations.

[0031] Hair softness is determined by several factors, including the hair's moisture content, the condition of the cuticle layer, and the presence of natural oils or conditioning agents. Objective measurement of hair softness can be performed using various techniques, such as tactile evaluation by trained raters, mechanical tests for flexibility and stretchability, and advanced imaging methods to assess the smoothness of the hair fiber surface. Furthermore, consumer perception research often involves panelists who evaluate hair softness after using specific products, providing valuable insights into how different formulations affect this important quality attribute.

[0032] The following materials are used in embodiments of the present invention. The present invention is described using non-limiting embodiments. The listed components are preferred features of the present invention, as well as other preferred but non-limiting features.

[0033] The preceding text of this specification and the measurement techniques described herein are well known to those skilled in the art and therefore do not limit the present invention.

[0034] In one embodiment, the present invention relates to a decolorizing medium. This decolorizing medium is (A) at least one photosensitizer capable of generating singlet oxygen which is at least one phenalenone, (B) at least one persulfate, (C) at least one alkalizing agent, (E) comprising at least one hydrogen peroxide source.

[0035] In the context of the present invention, the term "photosensitizer" refers to a compound that absorbs electromagnetic radiation, preferably visible light, ultraviolet light, and / or infrared light, thereby producing singlet oxygen.

[0036] In one embodiment, the decolorizing medium preferably comprises at least one second photosensitizer capable of generating singlet oxygen (A2) selected from the group consisting of curcumin, flavin, riboflavin, phenoxazine, phenothiazine, phthalocyanine, naphthalocyanine, xanthene, chlorophyll A, chlorophyll B, porphyrin, coumarin, pyrene, perylene, acridine orange, and tetrapyrrole.

[0037] Phenalenone is known to produce singlet oxygen (see, for example, J. Photochem. Photobiol. A: Chem, 79 (1994) 11-17 and New J. Chem., 1999, 23, 85-93).

[0038] In one embodiment, the phenalenone is an unsubstituted phenalenone, preferably substituted with at least one organic moiety at the 2-position of the phenalenone ring. This organic moiety is substituted with at least one positively charged nitrogen atom and / or at least one neutral, protonable nitrogen atom, as well as at least one negatively charged functional group.

[0039] In one embodiment, suitable flavins are disclosed in EP2723342A1, EP2723743A1, EP2723742A1, and US2019 / 0111168A1.

[0040] In one embodiment, a suitable curcumin is disclosed in US2019 / 0111168A1. A suitable curcumin derivative and its preparation are also described in CA2888140A1, and a suitable curcumin-3,5-dione derivative and its preparation are similarly described in EP2698368A1.

[0041] In one embodiment, phenoxazine is preferably Nile blue.

[0042] In one embodiment, the phenothiazine is preferably selected from the group consisting of methylene blue, toluidine blue, 1,9-dimethylmethylene blue, and methylene green.

[0043] In one embodiment, the phthalocyanine is preferably selected from the group consisting of zinc phthalocyanine, aluminum phthalocyanine, zinc phthalocyanine tetrasulfonate, and tetrakis(p-trimethylammonium)phthalocyanine zinc chloride.

[0044] In one embodiment, xanthene is preferably selected from the group consisting of pyronin G, eosin B, eosin Y, and rose bengal.

[0045] In one embodiment, the porphyrin is preferably selected from the group consisting of 5,10,15,20-tetrakis(1-methyl-4-pyridinio)porphyrin-tetra(p-toluenesulfonate) and tetrakis(p-trimethylammoniumphenyl)porphyrin chloride.

[0046] In one embodiment, the tetrapyrrole is preferably selected from the group consisting of chlorin, chlorin e6, and bacteriochlorin.

[0047] In one embodiment, at least one phenalenone (A) generates singlet oxygen when exposed to electromagnetic radiation having wavelengths preferably in the range of 230 nm to 1000 nm, preferably in the range of 380 nm to 1000 nm, more preferably in the range of 380 nm to 780 nm, even more preferably in the range of 380 nm to 490 nm, and most preferably in the range of 390 nm to 430 nm. The wavelength most suitable for the photosensitizer to generate singlet oxygen is selected based on the specific chemical properties of the photosensitizer.

[0048] In one embodiment, at least one phenalenone (A) is present in an amount preferably between 0.01 wt.% and 10.0 wt.% of the total weight of the decolorizing medium, preferably between 0.10 wt.% and 8.0 wt.% of the total weight, more preferably between 0.15 wt.% and 5.0 wt.% of the total weight, and most preferably between 0.20 wt.% and 3.0 wt.% of the total weight.

[0049] In one embodiment, at least one phenalenone (A) is preferably dissolved in at least one polar solvent before being mixed with other components of the decolorizing medium.

[0050] The ability of a solvent to dissolve a given substance, such as phenalenone, may be conveniently evaluated by parameter considerations according to the "Hansen system." These parameter considerations are described in the "Hansen Solubility Parameters - A Users Handbook," published by CRC Press (2000). According to the Hansen system, a solvent or solvent mixture may be described by three solubility parameters: δd (dispersion parameter), δp (polarity parameter), and δh (hydrogen bonding parameter).

[0051] In preferred embodiments, at least one polar solvent is selected from the group consisting of alkyl esters of fatty acids (such as methyl esters of fatty acids and ethyl esters of fatty acids), isopropyl esters of fatty acids (such as methyl oleate, methyl palmitate, methyl laurate, isopropyl myristate, or isopropyl palmitate), alcohols (such as ethoxydiglycol, 2-methoxyethanol, or 1-methoxy-2-propanol), dimethyl sulfoxides, and 1-methyl-2-pyrrolidone.

[0052] In a preferred embodiment, at least one polar solvent has a δd of 15.0 to 20.0 (MPa). 1 / 2 δp is between 2.0 and 28.0 (MPa) 1 / 2 , and δh is between 5.0 and 13.0 (MPa) 1 / 2It has a Hansen solubility parameter within the range.

[0053] In one embodiment, at least one solvent is present in an amount preferably between 0.5 wt.% and 5.0 wt.% and preferably between 0.5 wt.% and 2.0 wt.% based on the total weight of the decolorizing medium.

[0054] The decolorizing medium contains at least one persulfate (B). In one embodiment, at least one persulfate (B) is selected from the group consisting of alkaline earth metal persulfates, alkali metal persulfates, and ammonium persulfate, which exhibit oxidative activity, i.e., generate reactive oxygen species, when combined with an aqueous composition containing hydrogen peroxide. Examples of alkali metal persulfates include lithium persulfate, sodium persulfate, potassium persulfate, and cesium persulfate. Examples of alkaline earth metal salts include magnesium persulfate and calcium persulfate. In one embodiment, at least one persulfate (B) is preferably selected from the group consisting of ammonium persulfate, sodium persulfate, and potassium persulfate. The persulfate generally exists in the form of particles with an average particle diameter in the range of 0.1 μm to 200 μm.

[0055] In one embodiment, at least one component (B) is present in an amount preferably in the range of 3.0 wt.% to 30 wt.% based on the total weight of the decolorizing medium, more preferably in the range of 5.0 wt.% to 25 wt.% and even more preferably in the range of 7.0 wt.% to 20 wt.%.

[0056] In a preferred embodiment, at least one alkalizing agent (C) is selected from the group consisting of ammonia, alkanolamines, and inorganic alkalizing agents. In a preferred embodiment, the alkanolamine is selected from primary amines having a C2-C6 alkyl base supporting at least one hydroxyl group. Preferred alkanolamines are selected from the group consisting of monoethanolamine, 3-aminopropan-1-ol, 2-amino-1-propanol, 4-aminobutan-1-ol, 5-aminopentan-1-ol, 1-aminopropan-2-ol, 1-aminobutan-2-ol, 1-aminopentan-2-ol, 1-aminopentan-3-ol, 1-aminopentan-4-ol, 3-amino-2-methylpropan-1-ol, 1-amino-2-methylpropan-2-ol, 3-aminopropan-1,2-diol, and 2-amino-2-methylpropan-1,3-diol.

[0057] In another embodiment, the decolorizing medium contains other alkalizing agents, particularly inorganic alkalizing agents. Inorganic alkalizing agents usable as assumed herein are preferably selected from the group consisting of sodium hydroxide, potassium hydroxide, calcium hydroxide, barium hydroxide, sodium phosphate, potassium phosphate, alkali metal silicates, alkali metal metasilicates, alkaline earth metal silicates, alkaline earth metal metasilicates, sodium carbonate, and potassium carbonate. In a preferred embodiment, the inorganic alkalizing agent is selected from the group consisting of sodium silicate and sodium metasilicate.

[0058] In one embodiment, the decolorizing medium comprises at least one alkalizing agent (C), which is sodium silicate.

[0059] In another embodiment, at least one component (C) is present in an amount of 3.0 wt.% to 20 wt.%, preferably 4.0 wt.% to 15 wt.% and more preferably 5.0 wt.% to 12 wt.% based on the total weight of the decolorizing medium. At least one component (C), such as sodium silicate, is an alkali salt that imparts an aqueous basic pH when the decolorizing medium according to the present invention is combined with an aqueous medium.

[0060] Since persulfates and hydrogen peroxide are relatively stable in acidic media, it may be necessary to activate them at a neutral to basic pH to obtain the appropriate formulation. Therefore, it is common practice to add at least one alkalizing agent (C), such as an alkaline alkali metal silicate and / or ammonium silicate, to the decolorizing medium. Basic pH is an activating factor that allows oxidation by an oxidizing agent, such as hydrogen peroxide combined with persulfates.

[0061] In one embodiment, the decolorizing medium according to the present invention preferably comprises at least one additive (D). This additive (D) is selected from the group consisting of a source of carbonate ions, or bicarbonate ions, or carbamate ions; aluminosilicates; surfactants; chelating agents; thickeners; fillers; amino acids; hydrolyzed proteins; fatty substances; saturated acyclic terpanes having 10 to 40 carbon atoms; C3 to C20 monocarboxylic acids; and C3 to C10 dicarboxylic acids or tricarboxylic acids.

[0062] In another embodiment, at least one additive (D) is present in an amount preferably in the range of 2.0 wt.% to 30 wt.% based on the total weight of the decolorizing medium, more preferably in the range of 3.0 wt.% to 25 wt.%, even more preferably in the range of 4.0 wt.% to 20 wt.%, even more preferably in the range of 4.0 wt.% to 18 wt.%, most preferably in the range of 4.0 wt.% to 17 wt.%, and particularly in the range of 4.0 wt.% to 15 wt.% based on the total weight of the decolorizing medium.

[0063] In one embodiment, the source of carbonate ions, or bicarbonate ions, or carbamate ions is preferably selected from the group consisting of carbonate ions, carbamate ions, and sodium salts, potassium salts, guanidine salts, arginine salts, lithium salts, calcium salts, magnesium salts, barium salts, and ammonium salts of bicarbonate ions. In another embodiment, the source of at least one carbonate ion, or bicarbonate ion, or carbamate ion is present in an amount preferably in the range of 1.0 wt.% to 10.0 wt.%, more preferably in the range of 2.0 wt.% to 8.0 wt.%, and even more preferably in the range of 2.0 wt.% to 6.0 wt.%, based on the total weight of the decolorizing medium. The source of carbonate ions, or bicarbonate ions, or carbamate ions is a solid alkali salt that imparts an aqueous basic pH when the decolorizing medium is combined with an aqueous medium.

[0064] In one embodiment, the aluminosilicate is preferably sodium aluminosilicate. In another embodiment, the aluminosilicate is present in an amount preferably in the range of 3.0 wt.% to 15 wt.%, more preferably in the range of 4.0 wt.% to 12 wt.%, and even more preferably in the range of 4.0 wt.% to 10.0 wt.%, based on the total weight of the decolorizing medium.

[0065] In one embodiment, the decolorizing medium according to the present invention preferably comprises a surfactant, more preferably an anionic surfactant. These surfactants are selected from the group consisting of salts of the following compounds (alkali salts, e.g., sodium salts, ammonium salts, amine salts, amino alcohol salts, and magnesium salts): alkyl sulfates, alkyl ether sulfates, alkyl amide ether sulfates, alkyl aryl polyether sulfates, monoglyceride sulfates, alkyl sulfonates, alkyl phosphates, alkyl amide sulfonates, alkyl aryl sulfonates, alpha olefin sulfonates, paraffin sulfonates, alkyl sulfosuccinates, alkyl ether sulfosuccinates, alkyl sulfosuccinates, alkyl sulfoacetic acid esters, alkyl ether phosphates, acyl sarcosinates, acyl isethionates, N-acyl taurates, and mixtures thereof. The alkyl radicals or acyl radicals of these various compounds contain, for example, 8 to 24 carbon atoms, and the aryl radicals are selected from, for example, phenyl groups and benzyl groups. Weak anionic surfactants, such as alkyl-D-galactosidouronic acid and its salts, as well as polyoxyalkylene (C6-C24) alkyl ether carboxylic acids, polyoxyalkylene (C6-C24) alkylaryl ether carboxylic acids, polyoxyalkylene (C6-C24) alkylamide ether carboxylic acids, and their salts (e.g., those containing 2 to 50 ethylene oxide groups), and mixtures thereof may also be used. Anionic derivatives of polysaccharides, such as carboxyalkyl ethers of alkyl polyglucosides, may also be used.

[0066] In one embodiment, the surfactant is present in an amount preferably in the range of 1.0 wt.% to 9.0 wt.% based on the total weight of the decolorizing medium, more preferably in the range of 1.0 wt.% to 5.0 wt.% and even more preferably in the range of 1.0 wt.% to 4.0 wt.%.

[0067] In one embodiment, the decolorizing medium according to the present invention preferably comprises an anionic surfactant selected from the group consisting of alkali metal salts and alkaline earth metal salts of laurate, myristicate, palmitate, stearate, or behenate, and more preferably the anionic surfactant is selected from the group consisting of sodium salts and potassium salts of laurate, palmitate, or stearate.

[0068] In one embodiment, the decolorizing medium preferably includes a surfactant selected from the group consisting of nonionic surfactants, amphoteric or zwitterionic surfactants, and cationic surfactants.

[0069] In one embodiment, the nonionic surfactant is selected from the group consisting of fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, selectively partially oxidized alkyl (alkenyl) oligoglycosides or alkyl (alkenyl) polyglycosides or glucuronic acid derivatives, fatty acid-N-alkylglucamides, protein hydrolysates (especially plant-derived products from wheat), polyol fatty acid esters, sugar esters, sorbitan esters, polysorbates, and amine oxides.

[0070] Amphoteric surfactants contain at least one quaternary ammonium group and at least one -COO group in their molecule. (-) Base or -SO3 (-)These are surfactant compounds containing a group. Particularly suitable amphoteric surfactants are so-called betaines, such as N-alkyl-N,N-dimethylammonium glycinate (e.g., cocoalkyldimethylammonium glycinate), N-acylaminopropyl-N,N-dimethylammonium glycinate (e.g., cocoacylaminopropyldimethylammonium glycinate), 2-alkyl-3-carboxymethyl-3-hydroxyethylimidazoline, and cocoacylaminoethylhydroxyethylcarboxymethyl glycinate, which contain 8 to 18 carbon atoms in an alkyl or acyl group.

[0071] Amphoteric surfactants are surfactant compounds that contain at least one free amino group and at least one -COOH group or -SO3H group in addition to a C8-C18 alkyl or acyl group in their molecule, and are capable of forming intramolecular salts. Suitable examples of amphoteric surfactants include N-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyltaurine, N-alkylsarcosine, 2-alkylaminopropionic acid, and alkylaminoacetic acid, which contain about 8-18 carbon atoms in the alkyl group.

[0072] Particularly suitable cationic surfactants are quaternary ammonium compounds, preferably ammonium halides, and especially chlorides and bromides such as alkyltrimethylammonium chloride, dialkyldimethylammonium chloride, and trialkylmethylammonium chloride, for example, cetyltrimethylammonium chloride, stearyltriethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride, and tricetylmethylammonium chloride.

[0073] Hydrogen peroxide readily decomposes upon contact with heavy metals such as iron, copper, and manganese, and can quickly become ineffective. This drawback is usually overcome by incorporating a chelating agent into the formulation. In one embodiment, the decolorizing medium contains a chelating agent, which is preferably ethylenediaminetetraacetic acid (EDTA), ethylenediamine-N,N'-disuccinic acid (EDDS), ethylenediamine-N,N'-diglutaric acid (EDDG), 2-hydroxypropylenediamine-N,N'-disuccinic acid (HPDDS), N,N-dicarboxymethylglutamic acid (GLDA), methylglycine-N,N-diacetic acid (MGDA), glycinamide-N,N'-disuccinic acid (GADS), or ethylenediamine-N-N'-bis(orthohydroxyphenyl) The chelating agent is selected from the group consisting of ethylenediaminetetraacetic acid (EDDHA), dimethylglucamine (DMG), N-(1-carboxyethyl)iminodiacetic acid, methylglycine N,N-diacetic acid, diethylenetriaminepentaacetic acid (DTPA), ethylenedisysteic acid (EDC), N,N'-bis(2-hydroxybenzyl)ethylenediamine-N,N'-diacetic acid (HBED), ethylenediaminetri(methylenephosphonate), tetramethylethylenediamine (TMEDA), N,N,N',N'-tetraethylethylenediamine (TEEDA), and salts thereof. More preferably, the chelating agent is selected from the group consisting of ethylenediaminetetraacetic acid (EDTA), ethylenediamine-N,N'-disuccinic acid (EDDS), and salts thereof. In the context of chelating agents, "those salts" means all salts that have the same functional structure as the chelating agent it refers to, including alkali metal salts, alkaline earth metal salts, ammonium salts, substituted ammonium salts, and mixtures thereof, or sodium salts, potassium salts, calcium salts, magnesium salts, ammonium salts, and mixtures thereof, or monoethanolammonium salts, diethanolammonium salts, triethanolammonium salts, and mixtures thereof.

[0074] In one embodiment, the chelating agent is present in an amount preferably in the range of 0.1 wt.% to 3.0 wt.% based on the total weight of the decolorizing medium, more preferably in the range of 0.2 wt.% to 2.0 wt.% and even more preferably in the range of 0.3 wt.% to 1.5 wt.%.

[0075] The decolorizing medium according to the present invention preferably comprises at least one thickener. The thickener is typically water-soluble and imparts a desired semi-liquid to paste-like viscosity to the decolorizing medium. Typical thickeners include, but are not limited to, synthetic water-soluble polymers and naturally derived water-soluble polymers. In one embodiment, the decolorizing medium according to the present invention preferably comprises a thickener selected from the group consisting of cellulose derivatives, polyacrylic acid, acrylate copolymers, polysaccharide gums, xanthan gum, starch, guar gum, starch derivatives, alginic acid, and diallyldimethylammonium acrylate polymers, and more preferably selected from the group consisting of xanthan gum, starch, and alginic acid.

[0076] Exemplary embodiments of water-soluble synthetic polymer thickeners include polyvinylpyrrolidone, polyacrylic acid, polyacrylamide, non-crosslinked poly-2-acrylamidepropanesulfonic acid, acid-crosslinked poly-2-acrylamide-2-methylpropanesulfonic acid, and crosslinked poly-2-acrylamide-2-methylpropanesulfonic acid partially neutralized with ammonia. Further exemplary embodiments of synthetic water-soluble thickeners include non-crosslinked poly-2-acrylamide-2-methylpropanesulfonic acid combined with hydroxyalkylcellulose ether or poly(ethylene oxide), etc. Embodiments of water-soluble thickeners derived from natural sources include, but are not limited to, polymers having at least one sugar unit. Exemplary embodiments of naturally derived thickeners include, but are not limited to, nonionic guar gum, semi-synthetic guar gum modified with C1-C6 hydroxyalkyl groups, biopolysaccharide gums of microbial origin (e.g., scleroglucan or xanthan gum), gums derived from plant extracts (e.g., gum arabic, ghati gum, karaya gum, tragacanth gum, carrageenan gum, agar, and carob gum), pectin, alginates, starches (e.g., rice starch, corn starch, potato starch, canola starch, cassava starch and their hydrolyzed derivatives), hydroxyalkyl (C1-C6) cellulose, and carboxyalkyl (C1-C6) cellulose. Embodiments of water-soluble cellulosic thickeners include, but are not limited to, hydroxyalkyl (C1-C6) cellulose such as hydroxyethyl cellulose.

[0077] In one embodiment, the thickening agent is present in an amount preferably in the range of 0.5 wt.% to 5.0 wt.% based on the total weight of the decolorizing medium, more preferably in the range of 0.5 wt.% to 6.0 wt.% and even more preferably in the range of 1.0 wt.% to 4.0 wt.%.

[0078] In one embodiment, the decolorizing medium according to the present invention includes a filler selected from the group consisting of kaolin clay, smectite clay, and sepiolite clay. In one embodiment, the bulking agent is present in an amount preferably in the range of 0.5 wt.% to 10.0 wt.% based on the total weight of the decolorizing medium, more preferably in the range of 1.0 wt.% to 8.0 wt.% and even more preferably in the range of 1.0 wt.% to 6.0 wt.% based on the total weight of the decolorizing medium.

[0079] In one embodiment, the decolorizing medium preferably comprises at least one amino acid selected from the group consisting of alanine, glycine, phenylalanine, leucine, valine, isoleucine, glutamic acid, aspartic acid, citrulline, histidine, arginine, lysine, and tyrosine, and more preferably comprises at least one amino acid selected from the group consisting of alanine, glycine, valine, and arginine. Most preferably, the at least one amino acid is alanine, or glycine, or valine, or arginine. In a preferred embodiment, the decolorizing medium does not contain any other amino acids. The at least one amino acid present in the decolorizing medium of the present invention is oxidatively stable in the decolorizing medium. That is, the at least one amino acid is not oxidized, or is only very slightly oxidized, in the decolorizing medium by one of the following reactions: nucleophilic oxidation, electrophilic oxidation, or radical oxidation. In one embodiment, the at least one amino acid is preferably obtained from a natural source, and more preferably, the at least one amino acid is obtained from a plant source.

[0080] In one embodiment, the amino acid is present in an amount preferably in the range of 0.05 wt.% to 2.0 wt.% based on the total weight of the decolorizing medium, more preferably in the range of 0.1 wt.% to 1.5 wt.%, even more preferably in the range of 0.1 wt.% to 1.3 wt.%, and even more preferably in the range of 0.1 wt.% to 1.0 wt.%.

[0081] In one embodiment, the decolorizing medium preferably comprises a hydrolyzed protein selected from the group consisting of hydrolyzed keratin and hydrolyzed plant proteins. Hydrolyzed proteins are commercially available, such as AC Vegan Keratin OS, Nutrilan® Keratin LM, Gluadin® Kera-P LM, KeraMatch® V, FK Repair Ultra, FK Restore, FK Protect Plus, and ProSina TM That is the case.

[0082] In one embodiment, the decolorizing medium according to the present invention comprises a C3-C20 monocarboxylic acid, which is preferably selected from the group consisting of propionic acid, butyric acid, pentanoic acid, isopentanoic acid, hexanoic acid, isohexanoic acid, heptanoic acid, isoheptanoic acid, octanoic acid, isooctanoic acid, nonanoic acid, isononanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, palmitic acid, heptadecanoic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, nonadecanoic acid, and eicosanoic acid.

[0083] In one embodiment, the C3-C20 monocarboxylic acid is present in an amount preferably in the range of 0.05 wt.% to 2.0 wt.% based on the total weight of the decolorizing medium, more preferably in the range of 0.1 wt.% to 1.5 wt.%, even more preferably in the range of 0.1 wt.% to 1.3 wt.%, and even more preferably in the range of 0.1 wt.% to 1.0 wt.%.

[0084] In one embodiment, the decolorizing medium according to the present invention comprises a C3-C10 dicarboxylic acid or tricarboxylic acid, which is preferably selected from the group consisting of tartaric acid, succinic acid, malic acid, maleic acid, citric acid, tartaric acid, adipic acid, glutaric acid, oxalic acid, sebacic acid, glyoxylic acid, malonic acid, and hydroxyglutaric acid.

[0085] In one embodiment, the C3-C10 dicarboxylic acid or tricarboxylic acid is present in an amount preferably in the range of 0.05 wt.% to 2.0 wt.% based on the total weight of the decolorizing medium, more preferably in the range of 0.1 wt.% to 1.5 wt.%, even more preferably in the range of 0.1 wt.% to 1.3 wt.%, and even more preferably in the range of 0.1 wt.% to 1.0 wt.%.

[0086] In one embodiment, the decolorizing medium according to the present invention comprises at least one fatty substance selected from the group consisting of liquid hydrocarbons, non-silicone oils of animal, plant, mineral or synthetic origin, aliphatic alcohols, fatty acid esters and / or aliphatic alcohol esters, non-silicone waxes, silicones, and saturated acyclic terpanes.

[0087] More specifically, liquid hydrocarbons are - Linear or branched, selectively cyclic C6-C16 alkanes (such as hexane, undecane, dodecane, and tridecane), and isoparaffins (such as isohexadecane, isododecane, and isodecane), - Selected from the group consisting of linear or branched hydrocarbons having more than 16 carbon atoms of mineral, animal, or synthetic origin (such as volatile or non-volatile liquid paraffins and their derivatives, petrolatum, liquid petrolatum, polydecene, and hydrogenated polyisobutene such as Parleam®).

[0088] In preferred embodiments of the present invention, the liquid hydrocarbon is selected from the group consisting of volatile or non-volatile liquid paraffins and liquid petrolatum.

[0089] In a further embodiment of the present invention, the decolorizing medium of the present invention contains a fatty substance in an amount between 1.0 wt.% and 20.0 wt.% based on the total weight of the decolorizing medium.

[0090] In one embodiment, the decolorizing medium of the present invention comprises at least one saturated acyclic terpane, which is a monoterpane, sesquiterpane, diterpane, sesterterpane, triterpane, or tetraterpane. In another embodiment, the at least one saturated acyclic terpane is selected from the group consisting of 2,6-dimethyloctane, 2,6,10,15,19-pentamethylicosane, farnesane, phytan, squalane, isosqualane, neosqualane, and lycopane. In yet another embodiment, the at least one saturated acyclic terpane is selected from the group consisting of squalane, isosqualane, and neosqualane, and preferably, the at least one saturated acyclic terpane is squalane.

[0091] As used herein, "squalane" refers to an oil, also known as 2,6,10,15,19,23-hexamethyltetracosane. In one embodiment, squalane is synthetic squalane obtained by chemical synthesis, or semi-synthetic squalane obtained by reduction from naturally occurring squalene. Squalene is found in deep-sea fish such as sharks, or in olive oil, rice bran oil, wheat germ oil, sesame oil, and cottonseed oil. Squalane can also be obtained from sugarcane.

[0092] In yet another embodiment, at least one saturated acyclic terpane having 10 to 40 carbon atoms is present in an amount preferably in the range of 0.1 wt.% to 15.0 wt.%, more preferably in the range of 0.5 wt.% to 14.0 wt.%, even more preferably in the range of 0.5 wt.% to 5.0 wt.%, even more preferably in the range of 1.0 wt.% to 4.0 wt.%, most preferably in the range of 1.0 wt.% to 3.0 wt.%, and particularly in the range of 1.0 wt.% to 2.0 wt.% based on the total weight of the decolorizing medium.

[0093] In one embodiment, the decolorizing medium preferably comprises at least one hydrogen peroxide source (E) selected from the group consisting of hydrogen peroxide, calcium peroxide, urea peroxide, perborate, and percarbonate. The at least one hydrogen peroxide source (E) is preferably hydrogen peroxide and is present in a range of preferably 1.0 wt.% to 12 wt.% and preferably 2.0 wt.% to 6.0 wt.% based on the total weight of the decolorizing medium.

[0094] In one embodiment, the decolorizing medium according to the present invention is (A) At least one phenalenone in an amount of 0.5 wt.% to 3.0 wt.%, (B) At least one persulfate in an amount of 3.0 wt.% or more and 30 wt.% or less, (C) At least one alkalizing agent in an amount of 3.0 wt.% to 20 wt.%, (D) At least one additive (D) selected from the group consisting of carbonate ions, bicarbonate ions, or carbamate ions in an amount of 4.0 wt.% to 25 wt.%, selected from the group consisting of a source of carbonate ions, or bicarbonate ions, or carbamate ions, aluminosilicates, surfactants, chelating agents, thickeners, fillers, amino acids, hydrolyzed proteins, fatty substances, saturated acyclic terpanes having 10 to 40 carbon atoms, C3 to C20 monocarboxylic acids, and C3 to C10 dicarboxylic acids or tricarboxylic acids, (E) comprises at least one hydrogen peroxide source (E) in the range of 1.0 wt.% to 12 wt.%, preferably 2.0 wt.% to 6.0 wt.%, preferably hydrogen peroxide.

[0095] In one embodiment, the decolorizing medium according to the present invention is (A) At least one phenalenone in an amount of 0.2 wt.% to 3.0 wt.%, (B) At least one persulfate in an amount of 3.0 wt.% or more and 30 wt.% or less, (C) At least one alkalizing agent in an amount of 3.0 wt.% to 20 wt.%, (D) A source of carbonate ions, or bicarbonate ions, or carbamate ions, an aluminosilicate, a surfactant, a chelating agent, a thickening agent, a filler, an amino acid, a hydrolyzed protein, a fatty substance, a saturated acyclic terpane having 10 to 40 carbon atoms, a monocarboxylic acid of C3 - C20, and at least one additive (D) selected from the group consisting of a dicarboxylic acid or tricarboxylic acid of C3 - C10, in an amount of 4.0 wt.% or more and 25 wt.% or less. (E) Hydrogen peroxide in an amount of 2.0 wt.% or more and 6.0 wt.% or less, and at least one polar solvent having Hansen solubility parameters in the range of δd being 15.0 or more and 20.0 or less (MPa) 1 / 2 , δp being 2.0 or more and 28.0 or less (MPa) 1 / 2 , and δh being 5.0 or more and 13.0 or less (MPa) 1 / 2 in an amount of 0.5 wt.% or more and 5.0 wt.% or less.

[0096] In one embodiment, the decolorizing medium of the present invention is prepared by mixing a decolorizing powder containing at least one persulfate (B) and at least one alkalizing agent (C) with at least one aqueous medium containing at least one hydrogen peroxide source (E), whereby at least one component (A) can be present in the decolorizing powder or the aqueous medium, or at least one component (A) is added to the decolorizing powder or the aqueous medium. In one embodiment, the decolorizing powder is preferably prepared by dispersing all the compounds present in particulate form, i.e., at least one persulfate (B) and at least one alkalizing agent (C), in a fatty substance in which other liquid components of the decolorizing powder are pre-dispersed or pre-mixed, under mechanical action.

[0097] In another embodiment, the decolorizing powder is preferably prepared by extrusion by introducing the liquid phase and the solid phase of the decolorizing powder into an extruder and then mixing all the components at a temperature of 25°C or less using a co-rotating twin screw system including a transport means and a mixing means.

[0098] Bleaching powders are used in combination with oxygen donors such as hydrogen peroxide to bleach hair.

[0099] Therefore, in another aspect, the present invention relates to a method for bleaching hair, the method being at least a) The step of applying a decolorizing medium described herein to dry or wet hair to obtain coated hair, b) Exposing the covered hair to electromagnetic radiation having a wavelength in the range of 230 nm to 1000 nm, preferably 380 nm to 1000 nm, more preferably 380 nm to 780 nm, even more preferably 380 nm to 490 nm, and most preferably 390 nm to 430 nm; c) A step of rinsing the decolorizing medium off the coated hair, d) comprising the step of selectively drying the bleached hair.

[0100] In one embodiment, steps a) to d) may be repeated multiple times, for example, two or three times.

[0101] The decolorizing medium is preferably applied to the hair using any number of application devices, primarily for the purpose of applying a small amount of the decolorizing medium to the hair at a high density in order to obtain the desired decolorization result.

[0102] In one embodiment, electromagnetic radiation is preferably produced by a radiation source selected from the group consisting of artificial radiation sources such as UV lamps, IR lamps, fluorescent lamps, light-emitting diodes, and lasers.

[0103] In one embodiment, the energy density of electromagnetic radiation is preferably 1 mW / cm². 2 More than 70mW / cm 2 Within the following range, preferably 10 mW / cm² 2 More than 50mW / cm 2 Within the following range, more preferably 20 mW / cm² 2 More than 40mW / cm 2 It is within the following range.

[0104] In one embodiment, the pH of the decolorizing medium is 7.0 or lower. The acidic pH ensures the stability of hydrogen peroxide in the decolorizing medium. The pH is preferably obtained by adding at least one acidifying agent selected from the group consisting of hydrochloric acid, acetic acid, phosphoric acid, lactic acid, malic acid, and boric acid. The decolorizing medium preferably contains at least one auxiliary agent selected from the group consisting of preservatives, colorants, fragrances, defoamers, hydrogen peroxide stabilizers, and chelating agents such as EDTA and EDDS.

[0105] Oxidative hair dye compositions are typically sold in the form of kits comprising individually packaged components, such as in separate containers, including a dye or hair dye component comprising a dye coupler and a precursor, an aqueous hydrogen peroxide component, and a decolorizing medium comprising an alkalizing agent and a persulfate. In other embodiments, the present invention also relates to a kit comprising i) an individually packaged oxidative component comprising hydrogen peroxide, ii) an individually packaged dye component comprising at least one dye coupler and at least one dye precursor, and iii) an individually packaged decolorizing medium as described herein.

[0106] In one embodiment, hair is decolorized by applying a decolorizing medium described herein, and then dyed by applying a dyeing component comprising at least one dye coupler and at least one dye precursor. This combination of steps allows for the use of smaller amounts of dye coupler and dye precursor compared to procedures involving conventional decolorization and dyeing techniques.

[0107] In one embodiment, the dye precursor is toluene-2,5-diamine, p-phenylenediamine, n-phenyl-p-phenylenediamine, N,N-bis(2-hydroxyethyl)-p-phenylenediamine, hydroxyethyl-p-phenylenediamine sulfate, hydroxypropylbis(n-hydroxyethyl-p-phenylenediamine), 2-methoxymethyl-p-phenylenediamine, 2-chloro-p-phenylenediamine, p-aminophenol, p-methylaminophenol, 4-amino-m-cresol, 6-amino-m-cresol, bis(5-amino- The primary oxidative dye precursor is selected from the group consisting of 2-hydroxyphenyl)methane, tetraaminopyrimidine, 2,5,6-triamino-4-pyrimidinol, 4,5-diamino-1-(2-hydroxyethyl)pyrazole, 2,3-diaminodihydroxypyrazolopyrazolone dimethosulfonate, 4,5-diamino-1-hexylpyrazole, hydroxypropyl-p-phenylenediamine, dimethylpiperazinium-aminopyrazolopyridine chloride hydrochloride, methylimidazolium-propyl-p-phenylenediamine, hydroxyethoxyaminopyrazolopyridine, and salts thereof. Preferably, the primary oxidative dye precursor is selected from the group consisting of toluene-2,5-diamine, 4,5-diamino-1-hexylpyrazole, N,N-bis(2-hydroxyethyl)-p-phenylenediamine, hydroxypropyl-p-phenylenediamine, 2-methoxymethyl-p-phenylenediamine, and salts thereof.

[0108] In one embodiment, the dye coupler is resorcinol, 4-chlororesorcinol, 2-chlororesorcinol, 2-methylresorcinol, m-aminophenol, 4-amino-2-hydroxytoluene, 2-methyl-5-hydroxyethylaminophenol, 3-amino-2,6-dimethylphenol, 3-amino-2,4-dichlorophenol, 5-amino-6-chloro-o-cresol, 5-amino-4-chloro-o-cresol, hydroxybenzomorpholine, 2-amino-5-ethylphenol, 6-amino-m -Cresol, 6-amino-o-cresol, 2,4-diaminophenoxyethanol, 2-amino-4-hydroxyethylaminoanisole, 1,3-bis-(2,4-diaminophenoxy)propane, 2,6-dihydroxyethylaminotoluene, m-phenylenediamine, 2,4-diamino-1,5-di(2-hydroxyethoxybenzene), 1-naphthol, 2-methyl-1-naphthol, 1,5-naphthalenediol, 2,7-naphthalenediol, 1-acetoxy-2-methylnaphthalene, 2,6-dihydroxy- 3,4-dimethylpyridine, 2,6-dimethoxy-3,5-pyridinediamine, 3-amino-6-methoxy-2-(methylamino)-pyridine, 2-amino-3-hydroxypyridine, 2,6-diaminopyridine, dihydroxyindole, 6-hydroxyindole, dihydroxyindoline, phenylmethylpyrazolone, 1,2,4-trihydroxybenzene, 5-((2-hydroxyethyl)amino)-1,3-benzodioxole, isatin, hydroquinone, 4-formyl-1-methylquinolinium-p-toluenes The oxidative coupler dye precursor is selected from the group consisting of hydroxypropyl phosphates and their salts. Preferably, the oxidative coupler dye precursor is selected from the group consisting of resorcinol, 2-methylresorcinol, 4-chlororesorcinol, 2-chlororesorcinol, m-aminophenol, hydroxybenzomorpholine, 2,4-diaminophenoxyethanol, 4-amino-2-hydroxytoluene, 2-methyl-5-hydroxyethylaminophenol, 5-((2-hydroxyethyl)amino)-1,3-benzodioxole and their salts.

[0109] In one embodiment, the present invention relates to the use of at least one phenalenone for decolorizing hair by generating singlet oxygen.

[0110] In one embodiment, the present invention relates to a phenalenone in which the phenalenone ring is substituted with an organic moiety at the 2-position. This organic moiety is substituted with at least one positively charged nitrogen atom and / or at least one neutral and protonable nitrogen atom, and at least one negatively charged functional group, preferably at least one sulfonic acid group.

[0111] A positively charged nitrogen atom refers to a quaternary nitrogen atom, also known as an ammonium ion. This occurs when a nitrogen atom forms four covalent bonds with surrounding atoms or groups, resulting in a positively charged species.

[0112] A neutral, protonable nitrogen atom is one that has no net charge and can be protonated (H + This refers to a nitrogen atom that has the ability to accept (a ion), thereby becoming positively charged.

[0113] Negatively charged functional groups (also called anionic functional groups) are specific groups of atoms that acquire a net negative charge within a molecule by gaining one or more electrons. This negative charge significantly affects the chemical properties and reactivity of the molecule. Examples of such functional groups include, but are not limited to, sulfonic acid groups (S(=O)2-O - ), sulfate group (-OS(=O)2-O - ), carboxyl group (C(=O)-O - ), and phosphate group (PO4 3- ) are some examples.

[0114] Preferably, the organic moiety substituted with at least one positively charged nitrogen atom and / or at least one neutral, protonable nitrogen atom and at least one negatively charged functional group is selected from the group consisting of saturated or unsaturated alkyl radicals, saturated or unsaturated heteroalkyl radicals, saturated or unsaturated cycloalkyl radicals, saturated or unsaturated heterocyclic alkyl radicals, aryl radicals, and heteroaryl radicals. In each case, the aryl radical preferably has up to four, more preferably up to three, and still more preferably up to two fused rings. In each case, the aryl radical more preferably has one ring. In each case, the heteroaryl radical preferably has up to four, more preferably up to three, and still more preferably up to two fused rings. In each case, the heteroaryl radical more preferably has one ring.

[0115] In a more preferred embodiment, the heteroaryl radical in each case has 5 to 20, preferably 5 to 13, and more preferably 5 to 7 ring atoms, each comprising at least one carbon atom, 1 to 4 nitrogen atoms, and selectively 1 or 2 oxygen or sulfur atoms. In a more preferred embodiment, the saturated or unsaturated heterocyclic alkyl radical in each case has 5 to 20, preferably 5 to 13, and more preferably 5 to 7 ring atoms, each comprising at least one carbon atom, 1 to 4 nitrogen atoms, and selectively 1 or 2 oxygen or sulfur atoms.

[0116] In a more preferred embodiment, the saturated or unsaturated alkyl radical in each case is selected from the group consisting of methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, and n-octyl.

[0117] In a preferred embodiment, phenalenone is substituted at the 2-position of the phenalenone ring with an organic moiety substituted with at least one positively charged nitrogen atom and / or at least one neutrally protonable nitrogen atom, and at least one negatively charged functional group, preferably at least one sulfonic acid group. ● 4-[dimethyl-[(1-oxofenalen-2-yl)methyl]ammonio]butane-1-sulfonic acid, ● [(1-oxofenalen-2-yl)methylamino]methanesulfonate sodium, ● 4-[(1-oxofenalen-2-yl)methylamino]butan-1-sulfonate sodium, ● 2-[(1-oxofenalen-2-yl)methylamino]ethanesulfonate sodium, ● 3-[(1-oxofenalen-2-yl)methylamino]propane-1-sulfonate sodium ● 4-[diethyl-[(1-oxofenalen-2-yl)methyl]ammonio]butane-1-sulfonic acid, ● 4-[4-[(E)-(1-oxofenalen-2-yl)methyliminomethyl]pyridine-1-ium-1-yl]butane-1-sulfonic acid ● 4-[3-methyl-2-[(1-oxofenaren-2-yl)methylamino]imidazole-1-ium-1-yl]butane-1-sulfonic acid, and ● Selected from the group consisting of 4-[2-[(1-oxofenaren-2-yl)methylamino]thiazole-3-ium-3-yl]butan-1-sulfonic acid.

[0118] The present invention is associated with one or more of the following advantages:

[0119] ● When using the decolorizing medium of the present invention, hair exhibits a lower level of color fading compared to hair decolorized by conventional methods.

[0120] ● The decolorizing medium of the present invention allows for more efficient decolorization of hair.

[0121] ● When using the decolorizing medium of the present invention, the level of damage to the hair is equivalent to or less than that of the present invention.

[0122] ● When using the decolorizing medium of the present invention, the hair becomes softer to the touch compared to hair decolorized by conventional methods.

[0123] A list of embodiments is provided below to further illustrate this disclosure, but it is not intended to limit this disclosure to any particular embodiment listed below.

[0124] Embodiment 1. (A) At least one photosensitizer capable of generating singlet oxygen, (B) at least one persulfate, (C) at least one alkalizing agent, (E) A decolorizing medium comprising at least one hydrogen peroxide source.

[0125] 2. The decolorizing medium according to Embodiment 1, wherein the at least one photosensitizer capable of generating singlet oxygen (A) is selected from the group consisting of phenalenone, curcumin, flavin, riboflavin, phenoxazine, phenothiazine, phthalocyanine, naphthalocyanine, xanthene, chlorophyll A, chlorophyll B, porphyrin, coumarin, pyrene, perylene, acridine orange, and tetrapyrrole.

[0126] 3. The decolorizing medium according to Embodiment 2, wherein the phenalenone is selected from phenalenones substituted with at least one organic moiety substituted with at least one positively charged nitrogen atom and at least one negatively charged functional group.

[0127] 4. The decolorizing medium according to Embodiment 2, wherein the phenoxazine is Nile blue.

[0128] 5. The decolorizing medium according to Embodiment 2, wherein the phenothiazine is selected from the group consisting of methylene blue, toluidine blue, 1,9-dimethylmethylene blue, and methylene green.

[0129] 6. The decolorizing medium according to Embodiment 2, wherein the phthalocyanine is selected from the group consisting of zinc phthalocyanine, aluminum phthalocyanine, zinc phthalocyanine tetrasulfonate, and tetrakis(p-trimethylammonium)phthalocyanine zinc chloride.

[0130] 7. The decolorizing medium according to Embodiment 2, wherein the xanthene is selected from the group consisting of pyronin G, eosin B, eosin Y, and rose bengal.

[0131] 8. The decolorizing medium according to Embodiment 2, wherein the porphyrin is selected from the group consisting of 5,10,15,20-tetrakis(1-methyl-4-pyridinio)porphyrin-tetra(p-toluenesulfonate) and tetrakis(p-trimethylammoniumphenyl)porphyrin chloride.

[0132] 9. The decolorizing medium according to Embodiment 2, wherein the tetrapyrrole is selected from the group consisting of chlorin, chlorin e6, and bacteriochlorin.

[0133] 10. A decolorizing medium according to any one of Embodiments 1 to 9, wherein at least one photosensitizer capable of generating singlet oxygen (A) generates singlet oxygen when exposed to electromagnetic radiation having a wavelength in the range of 230 nm to 1000 nm, preferably in the range of 380 nm to 1000 nm.

[0134] 11. The decolorizing medium according to any one of Embodiments 1 to 10, wherein the at least one component (A) is present in an amount of 0.01 wt.% to 10.0 wt.% based on the total weight of the decolorizing medium, preferably in an amount of 0.1 wt.% to 8.0 wt.%, more preferably in an amount of 0.3 wt.% to 5.0 wt.% and most preferably in an amount of 0.5 wt.% to 3.0 wt.%.

[0135] 12. The decolorizing medium according to any one of Embodiments 1 to 11, wherein the at least one persulfate (B) is selected from the group consisting of ammonium persulfate, sodium persulfate, and potassium persulfate.

[0136] 13. The decolorizing medium according to any one of Embodiments 1 to 12, wherein the at least one component (B) is present in an amount of 3.0 wt.% to 30 wt.% based on the total weight of the decolorizing medium, preferably in the range of 5.0 wt.% to 25 wt.% and more preferably in the range of 7.0 wt.% to 20 wt.%.

[0137] 14. The decolorizing medium according to any one of embodiments 1 to 13, wherein the at least one alkalizing agent (C) is selected from the group consisting of ammonia, alkanolamines, and inorganic alkalizing agents.

[0138] 15. The decolorizing medium according to claim 14, wherein the alkanolamine is selected from the group consisting of monoethanolamine, 3-aminopropan-1-ol, 4-aminobutan-1-ol, 5-aminopentan-1-ol, 1-aminopropan-2-ol, 2-amino-1-propanol, 1-aminobutan-2-ol, 1-aminopentan-2-ol, 1-aminopentan-3-ol, 1-aminopentan-4-ol, 3-amino-2-methylpropan-1-ol, 1-amino-2-methylpropan-2-ol, 3-aminopropan-1,2-diol, and 2-amino-2-methylpropan-1,3-diol.

[0139] 16. The decolorizing medium according to claim 14, wherein the inorganic alkalizing agent is preferably selected from the group consisting of sodium hydroxide, potassium hydroxide, calcium hydroxide, barium hydroxide, sodium phosphate, potassium phosphate, alkali metal silicate, alkali metal metasilicate, alkaline earth metal silicate, alkaline earth metal metasilicate, sodium carbonate, and potassium carbonate.

[0140] 17. The decolorizing medium according to claim 16, wherein the inorganic alkalizing agent is selected from the group consisting of sodium silicate and sodium metasilicate.

[0141] 18. The decolorizing medium according to any one of Embodiments 1 to 17, wherein the at least one component (C) is present in an amount of 3.0 wt.% to 20 wt.% based on the total weight of the decolorizing medium, preferably in the range of 4.0 wt.% to 15 wt.% and preferably in the range of 5.0 wt.% to 12 wt.%.

[0142] 19. The decolorizing medium according to any one of embodiments 1 to 18, wherein the at least one hydrogen peroxide source (E) is selected from the group consisting of hydrogen peroxide, calcium peroxide, urea peroxide, perborate, and percarbonate.

[0143] 20. The decolorizing medium according to Embodiment 19, wherein the at least one hydrogen peroxide source (E) is hydrogen peroxide present in a range of preferably 1.0 wt.% to 12 wt.% and preferably 2.0 wt.% to 6.0 wt.% based on the total weight of the decolorizing medium.

[0144] 21. The decolorizing medium according to any one of Embodiments 1 to 20, comprising at least one additive (D), wherein the additive (D) is selected from the group consisting of carbonate ions, bicarbonate ions, or carbamate ions, aluminosilicates, surfactants, chelating agents, thickeners, fillers, amino acids, hydrolyzed proteins, fatty substances, saturated acyclic terpanes having 10 to 40 carbon atoms, C3 to C20 monocarboxylic acids, and C3 to C10 dicarboxylic acids or tricarboxylic acids.

[0145] 22. The decolorizing medium according to Embodiment 21, wherein the at least one additive (D) is present in an amount of 2.0 wt.% to 30 wt.% based on the total weight of the decolorizing medium, preferably 3.0 wt.% to 25 wt.%, more preferably 4.0 wt.% to 20 wt.%, even more preferably 4.0 wt.% to 18 wt.%, most preferably 4.0 wt.% to 17 wt.%, and particularly 4.0 wt.% to 15 wt.%.

[0146] 23. The decolorizing medium according to Embodiment 21, wherein the source of the carbonate ions, bicarbonate ions, or carbamate ions is selected from the group consisting of carbonate ions, carbamate ions, and sodium salts, potassium salts, guanidine salts, arginine salts, lithium salts, calcium salts, magnesium salts, barium salts, and ammonium salts of bicarbonate ions.

[0147] 24. The decolorizing medium according to any one of embodiments 21 to 23, wherein the source of at least one carbonate ion, bicarbonate ion, or carbamate ion is present in an amount of 1.0 wt.% to 10.0 wt.% based on the total weight of the decolorizing medium, preferably in an amount of 2.0 wt.% to 8.0 wt.%.

[0148] 25. The decolorizing medium according to Embodiment 21, wherein the aluminosilicate is sodium aluminosilicate.

[0149] 26. The decolorizing medium according to any one of embodiments 21 to 25, wherein the aluminosilicate is present in an amount of 3.0 wt.% to 15 wt.% based on the total weight of the decolorizing medium, preferably in the range of 4.0 wt.% to 12 wt.% and more preferably in the range of 4.0 wt.% to 10.0 wt.%.

[0150] 27. The decolorizing medium according to any one of embodiments 21 to 26, wherein the surfactant is selected from the group consisting of alkali metal salts and alkaline earth metal salts of laurate, myristicate, palmitate, stearate, or behenate.

[0151] 28. The decolorizing medium according to any one of embodiments 21 to 26, wherein the surfactant is selected from the group consisting of sodium and potassium salts of laurate, palmitate, or stearate.

[0152] 29. The decolorizing medium according to any one of embodiments 21 to 28, wherein the surfactant is present in an amount of 1.0 wt.% to 9.0 wt.% based on the total weight of the decolorizing medium, preferably in an amount of 1.0 wt.% to 5.0 wt.% and more preferably in an amount of 1.0 wt.% to 4.0 wt.%.

[0153] 30. The chelating agents include ethylenediaminetetraacetic acid (EDTA), ethylenediamine-N,N'-disuccinic acid (EDDS), ethylenediamine-N,N'-diglutaric acid (EDDG), 2-hydroxypropylenediamine-N,N'-disuccinic acid (HPDDS), N,N-dicarboxymethylglutamic acid (GLDA), glycinamide-N,N'-disuccinic acid (GADS), ethylenediamine-N-N'-bis(orthohydroxyphenylacetic acid) (EDDHA), dimethylglucamine (DMG), and N-(1-carb A decolorizing medium according to any one of Embodiments 21 to 29, selected from the group consisting of oxyethyl)iminodiacetic acid, methylglycine N,N-diacetic acid, diethylenetriaminepentaacetic acid (DTPA), ethylenedisysteic acid (EDC), N,N'-bis(2-hydroxybenzyl)ethylenediamine-N,N'-diacetic acid (HBED), ethylenediaminetri(methylenephosphonate), tetramethylethylenediamine (TMEDA), N,N,N',N'-tetraethylethylenediamine (TEEDA), and salts thereof.

[0154] 31. The decolorizing medium according to Embodiment 30, wherein the chelating agent is selected from the group consisting of ethylenediaminetetraacetic acid (EDTA), ethylenediamine-N,N'-disuccinic acid (EDDS), and salts thereof.

[0155] 32. The decolorizing medium according to any one of Embodiments 21 to 31, wherein the chelating agent is present in an amount of 0.1 wt.% to 3.0 wt.% based on the total weight of the decolorizing medium, preferably in the range of 0.2 wt.% to 2.0 wt.% and more preferably in the range of 0.3 wt.% to 1.5 wt.%.

[0156] 33. The decolorizing medium according to any one of Embodiments 21 to 32, wherein the thickening agent is selected from the group consisting of cellulose derivatives, polyacrylic acid, acrylate copolymers, polysaccharide gums, xanthan gum, starch, guar gum, starch derivatives, alginic acid, and diallyldimethylammonium acrylate polymer.

[0157] 34. The decolorizing medium according to Embodiment 33, wherein the thickening agent is selected from the group consisting of xanthan gum, starch, and alginic acid.

[0158] 35. The decolorizing medium according to any one of embodiments 21 to 34, wherein the thickening agent is present in an amount of 0.5 wt.% to 5.0 wt.% based on the total weight of the decolorizing medium, preferably in the range of 0.5 wt.% to 6.0 wt.% and more preferably in the range of 1.0 wt.% to 4.0 wt.%.

[0159] 36. The decolorizing medium according to any one of embodiments 21 to 35, wherein the filler is selected from the group consisting of kaolin clay, smectite clay, and sepiolite clay.

[0160] 37. The decolorizing medium according to any one of embodiments 21 to 36, wherein the filler is present in an amount of 0.5 wt.% to 10.0 wt.% based on the total weight of the decolorizing medium, preferably in the range of 1.0 wt.% to 8.0 wt.% and more preferably in the range of 1.0 wt.% to 6.0 wt.%.

[0161] 38. The decolorizing medium according to any one of Embodiments 21 to 37, wherein the amino acid is selected from the group consisting of alanine, glycine, phenylalanine, leucine, valine, isoleucine, glutamic acid, aspartic acid, citrulline, histidine, arginine, lysine, and tyrosine.

[0162] 39. The decolorizing medium according to any one of embodiments 21 to 38, wherein the amino acid is present in an amount within the range of 0.05 wt.% to 2.0 wt.% based on the total weight of the decolorizing medium, preferably within the range of 0.1 wt.% to 1.5 wt.%, more preferably within the range of 0.1 wt.% to 1.3 wt.%, and even more preferably within the range of 0.1 wt.% to 1.0 wt.%.

[0163] 40. The decolorizing medium according to any one of embodiments 21 to 39, wherein the hydrolyzed protein is selected from the group consisting of hydrolyzed keratin and hydrolyzed plant protein.

[0164] 41. The decolorizing medium according to any one of Embodiments 21 to 40, wherein the C3-C10 dicarboxylic acid or tricarboxylic acid is selected from the group consisting of tartonic acid, succinic acid, malic acid, maleic acid, citric acid, tartaric acid, adipic acid, glutaric acid, oxalic acid, sebacic acid, glyoxylic acid, malonic acid, and hydroxyglutaric acid.

[0165] 42. The decolorizing medium according to any one of Embodiments 21 to 41, wherein the C3-C20 monocarboxylic acid or the C3-C10 dicarboxylic acid or tricarboxylic acid is present in an amount of 0.05 wt.% to 2.0 wt.% based on the total weight of the decolorizing medium, preferably in the range of 0.1 wt.% to 1.5 wt.%, more preferably in the range of 0.1 wt.% to 1.3 wt.%, and even more preferably in the range of 0.1 wt.% to 1.0 wt.%.

[0166] 43. The decolorizing medium according to any one of embodiments 21 to 42, wherein the saturated acyclic terpane having 10 to 40 carbon atoms is selected from the group consisting of squalane, isosqualane, and neosqualane.

[0167] 44. (A) At least one photosensitizer capable of generating singlet oxygen in an amount of 0.5 wt.% to 3.0 wt.%, (B) At least one persulfate in an amount of 3.0 wt.% or more and 30 wt.% or less, (C) At least one alkalizing agent in an amount of 20 wt.% or more and 32 wt.% or less, (D) A decolorizing medium according to any one of Embodiments 1 to 43, comprising 2.0 wt.% to 25 wt.% of a source of carbonate ions, bicarbonate ions, or carbamate ions, aluminosilicate, surfactant, chelating agent, thickener, filler, amino acids, hydrolyzed proteins, fatty substances, saturated acyclic terpanes having 10 to 40 carbon atoms, C3 to C20 monocarboxylic acids, and C3 to C10 dicarboxylic acids or tricarboxylic acids.

[0168] 45. A method for bleaching hair, at least a) A step of applying a decolorizing medium described in any one of Embodiments 1 to 44 to the hair to obtain coated hair, b) Exposing the coated hair to electromagnetic radiation having a wavelength in the range of 230 nm to 1000 nm, preferably in the range of 380 nm to 1000 nm, c) A step of washing the decolorizing medium off the coated hair, d) A method comprising the step of selectively drying the bleached hair.

[0169] 46. ​​The method according to Embodiment 45, wherein the covered hair is exposed to electromagnetic radiation for a period of time between 1 minute and 50 minutes in step b).

[0170] 47. Use of at least one compound selected from the group consisting of phenalenone, curcumin, flavin, riboflavin, phenoxazine, phenothiazine, phthalocyanine, naphthalocyanine, xanthene, chlorophyll A, chlorophyll B, porphyrin, coumarin, pyrene, perylene, acridine orange, and tetrapyrrole to decolorize hair by generating singlet oxygen.

[0171] 48. The use according to Embodiment 47, wherein the at least one compound is selected from the phenalenones.

[0172] 49. A phenalenone substituted at the 2-position of the phenalenone ring with one organic moiety substituted with at least one positively charged nitrogen atom and at least one negatively charged functional group.

[0173] Although the present invention is described in terms of specific embodiments, certain modifications and equivalents will be obvious to those skilled in the art and will be included within the scope of the present invention.

[0174] Examples The present invention will be described in detail by the following non-limiting embodiments. More specifically, the test methods specified below are part of the general disclosure of this application and are not limited to any particular embodiment.

[0175] material ● Potassium persulfate is commercially available from United Initiators (Pulach, Germany).

[0176] ● Alkaline sodium silicate is commercially available from BASF (Ludwigshafen / Rhein, Germany).

[0177] ● Ammonium persulfate is commercially available from United Initiators (Pulach, Germany).

[0178] ● Magnesium carbonate hydroxide is commercially available from Dr. Paul Lohmann GmbH (Emersal, Germany).

[0179] ● Sodium stearate is commercially available from Matrix Chemie.

[0180] ● Squalane is commercially available from Aprinnova.

[0181] ● Xanthan gum is commercially available from KP Kelco (Grossenbrode, Germany).

[0182] ● Algin is commercially available from BASF (Ludwigshafen / Rhein, Germany).

[0183] ● Disodium EDTA is commercially available from BASF (Ludwigshafen / Rhein, Germany).

[0184] ● D,L-malic acid is commercially available from Merck Chemicals GmbH (Darmstadt, Germany).

[0185] ● Mineral oil is commercially available from Panama PetroChem (India).

[0186] Synthesis of phenalenone 1) Synthesis of phenalenone(IV): [ka] Malonic acid (4.0 eq, 53.3 g, 512 mmol) and 1-naphthaldehyde(I) (1.0 eq, 20.0 g, 128 mmol, 17.4 mL) were dissolved in pyridine (70 mL, 3.5 parts by volume) at room temperature, while a catalytic amount of piperidine (0.2 eq, 2.2 g, 26 mmol, 2.5 mL) was added as a base. The reaction mixture was then heated under reflux for 2 hours. The reaction mixture was cooled to room temperature, and a white-beige residue precipitated while adding 250 mL of ice water under vigorous stirring. The yield was further increased while adjusting the pH level to 4 with concentrated hydrochloric acid. The residue was collected by vacuum filtration and washed with ice water to obtain the intermediate (E)-3-(1-naphthyl)prop-2-enoic acid(II) as a slightly beige powder in 93% yield (23.9 g, 119 mmol).

[0187] (E)-3-(1-naphthyl)prop-2-enoic acid(II) (1.0 eq, 3.0 g, 15 mmol) was suspended in dichloromethane (DCM) (30 mL, 10 parts by volume), a catalytic amount of DMF (100 μl) was added, and the mixture was cooled to 0°C. Then, oxalyl chloride (1.5 eq, 2.9 g, 23 mmol, 2.0 mL) was slowly added, and once the addition was complete, the reaction mixture was heated to room temperature with stirring until a clear yellow solution was formed. The reaction mixture was cooled again to 0°C, and aluminum chloride (2.0 eq, 4.0 g, 30 mmol) was added all at once. The reaction mixture was slowly heated to room temperature, and then heated for 4 hours under reflux. After cooling to room temperature, the reaction mixture was filtered, and the solvent was completely evaporated under reduced pressure. The resulting residue was collected in 50 mL of saturated sodium bicarbonate solution and stirred for 30 minutes. The formed precipitate was collected by filtration, washed with water, and dried. The crude product was recrystallized with toluene to obtain pure phenalenone(IV) in 77% yield (2.1 g, 12 mmol).

[0188] 2) Synthesis of substituted phenalenones Phenalenone was converted to 2-(chloromethyl)phenalen-1-one according to the protocol described in Godard et al., ACSO Mega 2020, 5, 28264-28272.

[0189] 2a) Synthesis of 4-[dimethyl-[(1-oxofenalen-2-yl)methyl]ammonio]butane-1-sulfonic acid (VI): [ka] 0.23 g (1.00 mmol) of 2-(chloromethyl)phenalen-1-one(V) was dissolved in 2 mL of DMF to form a clear yellow solution, which was heated to 85°C. In a separate container, 0.90 g (5.00 mmol) of 4-(dimethylammonio)butane-1-sulfonic acid was dissolved in 3 mL of DMF and 5 mL of water. Since 4-(dimethylammonio)butane-1-sulfonic acid is highly sensitive to light, the reaction was carried out in the dark. The solution containing 4-(dimethylammonio)butane-1-sulfonic acid was slowly added to the 2-(chloromethyl)phenalen-1-one(V) solution in DMF at 85°C. The reaction mixture was then heated further to 100°C with stirring for 24 hours, resulting in a deep dark yellow solution. The reaction mixture was then cooled to room temperature and diluted with 10 mL of DMF. Excess 4-(dimethylammonio)butane-1-sulfonic acid precipitated from the solution and was removed by filtration. The filtrate was then washed with a small amount of DMF. The filtrate was then evaporated under reduced pressure to approximately 10% of its volume, and cold diethyl ether was added. The precipitated crude product was recovered by filtration and further recrystallized with methanol to remove more polar impurities, yielding the desired 4-[dimethyl-[(1-oxophenalen-2-yl)methyl-]ammonio]butane-1-sulfonic acid (VI) in 50% yield (0.19 g).

[0190] 2b) Synthesis of 4-[(1-oxofenalen-2-yl)methylamino]butane-1-sulfonic acid (VIII) [ka] 0.15 g (0.72 mmol) of 2-(aminomethyl)phenalen-1-one (VII) was dissolved in a mixture of 4 mL of acetonitrile and 1 mL of methanol at 50°C to form a clear red solution. 0.10 g (0.75 mmol) of oxatian 2,2-dioxide was added to this solution at 50°C. The reaction mixture was then heated at 70°C for 12 hours. After evaporating the solvent under reduced pressure, the resulting precipitate was collected with 5 mL of diethyl ether and filtered. The residue was then washed with 5 mL of toluene to obtain the desired 4-[(1-oxophenalen-2-yl)methylamino]butane-1-sulfonic acid (VIII) in 53% yield (0.13 g).

[0191] 2c) Synthesis of sodium [(1-oxofenaren-2-yl)methylamino]methanesulfonate (IX) [ka] 0.56 g (2.29 mmol) of 2-(aminomethyl)phenalen-1-one(VII) was dissolved in 10 mL of methanol. In a separate container, 0.355 g (2.51 mmol) of commercially available sodium methanehydroxysulfonate was dissolved in 1 mL of water. This solution was added to the 2-(aminomethyl)phenalen-1-one(VII) solution in methanol at 60°C. The reaction mixture was then stirred at 60°C for 2 hours. Next, the solvent was carefully evaporated to obtain a dark red slurry, after which 5 mL of water was added and the mixture was stirred at room temperature. Next, the reaction mixture was heated to 60°C and then 1 mL of ethyl acetate was added. The formed yellow-orange crystals precipitated from the solution and were recovered by filtration. The crystals were crushed in a mortar by adding water and acetone. While the formed solid was recovered by filtration, another portion of the crystals precipitated from the filtrate. The recovered solids were combined to obtain the desired compound, sodium [(1-oxophenalen-2-yl)methylamino]methanesulfonic acid (IX), in a yield of 63% (0.47 g).

[0192] hair tuft Level 7.0 and Level 5.0 Caucasian hairpieces (bundles 10cm long and 1cm wide) were supplied by Kerling International Haarfabrik GmbH (Bakhnang, Germany).

[0193] Test method Measurement of comb-through force Various external factors, such as specific cosmetic treatments (bleaching, dyeing, permanent waves), exposure to weather, and frequent combing and brushing, affect the ease of combing due to the deterioration of the hair cuticle. Therefore, the ease of combing hair is a key parameter for describing, on the one hand, the quality / degree of damage of the hair, and on the other hand, the effectiveness of conditioning in each hair repair treatment. The principle of most methods for determining combability is to measure the force with which a comb is pulled through a hair strand under specific conditions (see CR Robbins, Chemical and Physical Behavior of Human Hair, 5th Edition, p.646 ff., Springer-Verlag, Berlin Heidelberg 2012. ISBN 978-3-642-25610-3). In this test, the hair strand under test was taken from a storage room and an automated device fixed to a force gauge was used. The hair strand was automatically combed at a constant speed. For each combing stroke, the combing force was recorded as a function of the distance combed (length of the hair strand). For comparison, each product sample was combed 20 times on at least three strands, and the average value was taken. The combing force for wet hair was the average force along the strand. A lower combing force indicates easier combing.

[0194] Hunter Lab Color Measurement The L*a*b* color values ​​obtained in the above example were measured using a Chromameter II colorimeter supplied by Minolta. The L value represents lightness (higher L value indicates higher lift), the a value represents a measure of red content (higher a value indicates higher red content), and the b value represents a measure of blue content; the higher the blue content, the more negative the b value.

[0195] Damage measurement using FT-IR Hair damage was assessed using FT-IR (Fourier Transform Infrared Spectroscopy), a method established as suitable for studying the effects of keratin surface damage. (Strassburger, J., J.Soc. Cosmet Chem., 36, 61-74 (1985); Joy, M. & Lewis, DM, Int. J. Cosmet. Sci., 13, 249-261 (1991); Signori, V. and Lewis, DM, Int. J. Cosmet. Sci., 19, 1-13 (1997)). In particular, the authors demonstrated that this method is suitable for quantifying the amount of cysteic acid. In general, cystine oxidation is considered a suitable marker for monitoring the overall oxidation of the keratin portion of fibers. In short, the measurement of cysteic acid units by FT-IR has been commonly used.

[0196] Signori and Lewis (DM, Int. J. Cosmet. Sci., 19, 1-13 (1997)) demonstrated that FT-IR using a diamond attenuated total internal reflection (ATR) cell is a highly sensitive and reproducible method for measuring the cysteic acid content of single fibers and bundles. Therefore, the method employed to measure the cysteic acid content of multiple fiber bundles and the entire hairpiece was based on the FTIR diamond ATR cell method adopted by Signori and Lewis (1997). A detailed description of the methods for testing different damage inhibitors follows.

[0197] Cysteic acid concentration in mammalian or synthetic hair was measured using a Perkin Elmer Spectrum® 1 Fourier Transform Infrared (FTIR) configuration with a diamond attenuated total internal reflection (ATR) cell. This method used hairpieces of various sizes and colors. To minimize variations in contact area between readings, the hairpieces were braided (approximately one braid per cm). To simulate the behavior of hair after repeated decolorization cycles, the decolorization method described below was repeated five times. After this treatment, four readings were taken for each hairpiece (the bottom 1 / 3 and 2 / 3 on both sides of the hairpiece), and the average value was calculated. Background was collected after every four readings, and an ATR cell pressure of 1 N / m was employed. Between each reading, the cell was cleaned with ethanol, and contamination was checked using the instrument's monitor ratio mode. A normalized double derivative analysis routine was used, as defined by Signori and Lewis in 1997. The original spectrum was first converted to absorbance, and then converted to 1450 cm⁻¹. -1 The data was normalized to a band (characteristic and invariant protein CH2 stretching). This normalized absorbance was derived twice using 13-point averaging. 1040 cm -1 Absorbance at 1450cm -1 The value of the normalized second derivative was used as the relative concentration of cysteic acid. To convert to the appropriate units, this value was multiplied by -1 × 10⁻¹⁰. 4 We multiplied by it.

[0198] combination A decolorized powder formulation sample was prepared by mixing all dry components in a mixer for 5 minutes at a mixing blade rotation speed of 3.5 rpm. The dust removal component was added drop by drop while the rotation speed was set to 3 rpm. Finally, a homogeneous mixture was ensured by increasing the speed to 3.5 rpm for 6 minutes.

[0199] Table 1 Decolorized Powder Formulation [Table 1]

[0200] Table 2. Examples of oxidizing compositions (6% color developer) [Table 2]

[0201] Table 3 Photosensitizer preparations Unsubstituted phenalenone(IV) 20 mg was dissolved in the following solvents in different amounts. [Table 3]

[0202] Table 4 Hair dye composition [Table 4]

[0203] Bleaching method In the embodiments of the present invention, Welloxon® Perfect 6% or 9% oxidizing formulations containing 6 wt.% or 9 wt.% hydrogen peroxide in an aqueous medium were used, based on the total weight of the product (a color developer from Wella Germany GmbH (Darmstadt, Germany)).

[0204] The decolorization composition was prepared by mixing the decolorization powders listed in Table 1 with a photosensitizer formulation and a commercially available color developer, as described above.

[0205] The performance of each oxidative hair treatment composition was evaluated using the following protocol.

[0206] 1. Three locks of natural white hair were used as described above.

[0207] 2. A decolorizing composition prepared using Welloxon® Perfect 9% and Blondor® was applied.

[0208] 3. Mix 1 part of each bleaching powder with 1.5 parts of the oxidizing composition (Welloxon® Perfect 9%), then apply and distribute evenly over the entire hair section using a brush. Apply 4g of the product to each 1g section of hair.

[0209] 3. The cluster has a frequency of 415 nm and an energy density of 35 mW / cm². 2 They were either exposed to electromagnetic radiation or placed in a 30°C oven for 40 minutes.

[0210] 4. Afterwards, soak the grapes in 4L of water at a temperature of 37±2℃ for 2 minutes. -1 I washed it off.

[0211] 5. Comb the tuft of hair twice (using the coarse side of the comb and the fine side), and then place it between the pre-moistened pieces of paper.

[0212] 6. The combing force was measured three times for each bunch.

[0213] Examples [Table 5]

[0214] The provided examples demonstrate that including both phenalenone IV and IX in the hair treatment process results in higher lift compared to phenalenone-free treatments, as indicated by increased ΔL values. Specifically, the phenalenone-utilized examples (Examples 3, 4, 7, and 8) showed ΔL values ​​in the range of 37.7135 to 43.6275, which is significantly higher than the phenalenone-free control examples (Examples 1, 2, 5, and 6), which showed ΔL values ​​of 36.3245 to 40.208. Furthermore, FTIR measurements show that the resulting damage, as reflected by the ΔFTIR value, is comparable between the phenalenone-containing treatments and the control. For example, the ΔFTIR values ​​of hair treated with phenalenone are in the range of 110.05 to 118.91, while the ΔFTIR values ​​of the control are in the range of 103.11 to 111.53. This demonstrates that phenalenone enhances hair lift without significantly increasing oxidative damage to the keratin structure, as measured by the formation of cysteic acid.

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