Bleaching media containing photosensitizers

Abstract

The presently claimed invention relates to a bleaching medium comprising at least one phenanone capable of generating singlet oxygen, at least one persulfate, at least one basifying agent and at least one source of hydrogen peroxide, and to a method for bleaching the hair using said bleaching medium.

Description

Technical Field

[0001] The currently claimed invention relates to a bleaching 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 of bleaching hair using said bleaching medium. Background Technology

[0002] Hair bleaching is a well-established technique in the hair care industry. Hair bleaching involves applying an oxidizing agent to the hair over a period of time to effectively achieve a 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. Applying hydrogen peroxide to the hair under alkaline pH conditions gradually lightens the hair color by oxidizing the melanin that gives it its color.

[0003] To enhance the bleaching effect of peroxide solutions, persulfate-based preparations can be incorporated as "synergists." Sodium persulfate, potassium persulfate, or ammonium persulfate are supplied in powder form and are mixed with hydrogen peroxide solution before use. The mixed product is then applied to the hair for a period of time to effectively achieve the desired lighter hair color.

[0004] Currently, hair bleaching agents are most commonly available in two-component kits. One component contains an aqueous hydrogen peroxide composition, and the second component contains a powdered bleaching composition containing persulfate and an alkaline agent. When the two components are mixed, the alkaline agent acts as an accelerator for the bleaching process. This powdered bleaching composition can be used alone or in combination with the aqueous hydrogen peroxide composition for bleaching hair. Hydrogen peroxide and persulfate are highly reactive when combined, and in addition to hydrogen and sodium sulfide, nascent oxygen is formed. This nascent oxygen greatly promotes the oxidation and bleaching of melanin in the hair.

[0005] Unfortunately, the process of bleaching hair not only lightens the hair color, but also alters the perceived hair tone, resulting in an effect often described as off-color or brassy. In other words, bleached hair appears more orange compared to untreated hair of a similar color.

[0006] Soft hair is an enviable quality, crucial to the overall feel and appearance of healthy, well-cared-for hair. Soft hair is generally easier to manage, easier to style, and feels pleasantly soft, enhancing both personal appearance and comfort. Soft hair is often a sign of good hydration and care, indicating smooth and well-organized cuticles with reduced friction and tangles. This characteristic is particularly beneficial as it reduces breakage and split ends, making hair stronger and more resilient over time.

[0007] US 9,895,299 B2 describes a method for bleaching or dyeing keratin fibers, comprising the steps of applying a composition containing one or more chemical oxidants and irradiating the hair with ultraviolet-visible light.

[0008] US 4,792,341 discloses a method and apparatus for artificially bleaching or lightening hair by exposing it to strong artificial light radiation.

[0009] EP 451 261 B1 describes a method for bleaching hair under light, wherein 10 to 120 g of an agent is applied to the hair and left on for up to 80 minutes, said agent being a solution, emulsion, or gel and containing at least one photosensitizer and a compound capable of providing hydrogen radicals. The hair is then irradiated with visible light and / or ultraviolet light.

[0010] None of the existing technical references disclose the use of photosensitizers that generate singlet oxygen to bleach hair.

[0011] There is a need to provide hairstylists and consumers with a bleaching medium that effectively bleaches hair while reducing color casts and maintaining a level of damage comparable to or lower than that of conventional bleaching techniques.

[0012] Therefore, one object of the currently claimed invention is to provide a bleaching medium composition that effectively bleachs hair while reducing discoloration and maintaining a level of damage comparable to or lower than that of conventional bleaching techniques. Summary of the Invention

[0013] Surprisingly, it was found that adding at least one photosensitizer capable of generating singlet oxygen to a bleaching medium containing at least one persulfate, at least one alkalizing agent, and at least one source of hydrogen peroxide can reduce the degree of color cast, thereby effectively formulating a hair bleaching medium that can effectively bleach hair while reducing or maintaining the degree of damage to hair caused by conventional bleaching techniques, as evidenced by lower combing force and help to make hair soft.

[0014] Therefore, in one aspect, the currently claimed invention relates to a bleaching medium comprising:

[0015] (A) At least one photosensitizer capable of generating singlet oxygen, said photosensitizer being at least one phenalenone.

[0016] (B) At least one persulfate,

[0017] (C) at least one alkalizing agent, and

[0018] (E) At least one source of hydrogen peroxide.

[0019] In another aspect, the currently claimed invention relates to a method for bleaching hair, which includes at least the following steps:

[0020] a) Apply bleaching medium to the hair to obtain covered hair.

[0021] b) Exposing the covered hair to electromagnetic radiation with a wavelength 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.

[0022] c) Rinse the bleaching medium off the covered hair, and

[0023] d) Optionally dry the bleached hair.

[0024] In another aspect, the currently claimed invention relates to the use of at least one naphthaleneacetone for bleaching hair by generating singlet oxygen.

[0025] In another aspect, the currently claimed invention relates to a naphthalene ketone in which an organic moiety is substituted at the 2 position of the naphthalene ketone ring, said organic moiety being substituted by at least one positively charged nitrogen atom and / or at least one neutral, protonable nitrogen atom and at least one negatively charged functional group.

[0026] Other objects, advantages, and applications of the currently claimed invention will become apparent to those skilled in the art from the following detailed description. Detailed Implementation

[0027] The following detailed description is exemplary in nature only and is not intended to limit the invention currently claimed or its application and use. Furthermore, it is not intended to be bound by any theory presented in the foregoing technical field, background art, summary of the invention, or the following detailed description.

[0028] The terms “comprising,” “comprises,” and “comprised of” as used herein are synonymous with “including,” “includes,” “containing,” and “contains,” and have an inclusive or open-ended meaning, not excluding additional unlisted members, elements, or method steps. It should be understood that the terms “comprising,” “comprises,” and “comprised of” as used herein include the terms “consisting of,” “consists,” and “consists of.”

[0029] Furthermore, the terms “(a)”, “(b)”, “(c)”, “(d)”, etc., used in the specification and claims are used to distinguish similar elements and are not necessarily used to describe an order or chronological order. It should be understood that such terms are interchangeable where appropriate, and embodiments of the subject matter described herein can operate in orders other than those described or shown herein. Where terms “(A)”, “(B)”, and “(C)”, or “(a)”, “(b)”, “(c)”, “(d)”, “(i)”, “(ii)”, etc., relate to steps of a method, use, or analysis, there is no temporal or time interval continuity between these steps; that is, the steps may be performed simultaneously, or there may be time intervals of seconds, minutes, hours, days, weeks, months, or even years between these steps, unless otherwise stated in the foregoing or hereinafter.

[0030] When used with respect to weight ratios or weight percentages, the term "about" should be understood to mean a range of ±10%. For example, about 1% by weight of a compound means a weight percentage ranging from 0.9% to 1.1%. For example, about 2.5% by weight of a compound means a weight percentage ranging from 2.25% to 2.75%.

[0031] The different aspects of the subject matter are defined in more detail in the following paragraphs. Unless explicitly stated otherwise, each aspect so defined may be combined with any other aspect or combination thereof. In particular, any feature indicated as preferred or advantageous may be combined with any other feature indicated as preferred or advantageous.

[0032] The terms "an embodiment" or "preferred embodiment" used in this specification mean that a specific feature, structure, or characteristic described in connection with the embodiment is included in at least one embodiment of the currently claimed invention. Therefore, the phrases "in an embodiment" or "in a preferred embodiment" appearing in different places in this specification do not necessarily refer to the same embodiment, but may refer to different embodiments of the currently claimed invention. Furthermore, in one or more embodiments, features, structures, or characteristics can be combined in any suitable manner, as will be apparent to those skilled in the art based on this disclosure. Moreover, while some embodiments described herein include certain features, other features included in other embodiments are not included, but combinations of features from different embodiments are intended to be within the scope of the subject matter and form different embodiments, as will be understood by those skilled in the art. For example, in the appended claims, any claimed embodiment can be used in any combination.

[0033] Furthermore, the range defined throughout the specification also includes end values; that is, the range of 1 to 10 means that both 1 and 10 are included in the range. For the avoidance of doubt, the applicant shall enjoy any equivalents under applicable law.

[0034] For the purposes of the presently claimed invention, '% by weight' or 'wt.%' as used in the presently claimed invention refers to the total weight of the bleaching medium. Furthermore, as stated herein, the sum of the weight % of all compounds in each component is 100% by weight.

[0035] Unless expressly excluded or otherwise limited, every document referenced herein, including any cross-referenced or related patents or applications, is incorporated herein in its entirety by reference. Reference to any document does not constitute an admission that it is prior art to any invention disclosed or claimed herein, or that it, alone or in any combination with any other one or more references, teaches, suggests, or discloses any such invention. Furthermore, if any meaning or definition of a term in this document conflicts with any meaning or definition of the same term in any document incorporated by reference, the meaning or definition given to the term in this document shall prevail.

[0036] The measurement techniques described above and herein are well known to those skilled in the art and therefore do not limit the invention currently claimed.

[0037] "User" or "consumer" refers to the person who prepares the hair treatment composition. For example, the user may be a professional hairstylist working in a beauty salon and is not the same person as the subject applying the composition to their hair, or the user may be the same person applying the composition to their hair. Mixing can be done in a bowl or bottle, or even by a mixer placed between the stored individual composition and the point where it is dispensed for use. While two-component bleaching media are the most common on the market, other bleaching media using three or more components also exist.

[0038] "Brightening effect" (or "brightening power") refers to the degree of lightening of natural hair pigment melanin caused by bleaching with the bleaching medium of the currently claimed invention. The degree of brightening provided by different hair treatment compositions can be compared by using a sample of naturally dark human hair (e.g., dark hair from a Chinese individual) and measuring the color change achieved after application of the composition. The color change can be measured using known parameters such as L*a*b* values. The L* value, or so-called dL* value (derived from L*a*b*), is measured on a given dark hair sample treated with one composition under the same experimental conditions. 最终 -L* 初始 When a composition is given a higher value than another composition, it can be said that the composition provides a stronger brightening effect than the other composition. Grade 2 (which may be used interchangeably with "semi-permanent" or "tone color" in this document) and Grade 3 (which may be used interchangeably with "permanent") are commonly used in the hair coloring industry to distinguish compositions with medium and high brightening effects.

[0039] Hair softness is determined by several factors, including the hair's moisture content, the condition of the hair cuticle, and the presence of natural oils or applied conditioning agents. Objective measurements of hair softness can be performed using various techniques, such as tactile assessments by trained evaluators, mechanical tests for flexibility and malleability, and advanced imaging methods for assessing the surface smoothness of hair fibers. Furthermore, consumer perception studies typically involve panelists rating hair softness after using a specific product, providing valuable insights into how different formulations affect this key quality attribute.

[0040] The following materials are used in embodiments of the currently claimed invention. The currently claimed invention is described with reference to non-limiting embodiments. The listed components are preferred features of the currently claimed invention, as well as other preferred but non-limiting features.

[0041] The measurement techniques described above and herein are well known to those skilled in the art and therefore do not limit the invention currently claimed.

[0042] In one aspect, the currently claimed invention relates to a bleaching medium comprising:

[0043] (A) At least one photosensitizer capable of generating singlet oxygen, said photosensitizer being at least one naphthaleneacetone.

[0044] (B) At least one persulfate,

[0045] (C) at least one alkalizing agent, and

[0046] (E) At least one source of hydrogen peroxide.

[0047] In the context of the currently claimed invention, the term "photosensitizer" refers to a compound that absorbs electromagnetic radiation, preferably visible light, ultraviolet light, and / or infrared light, and thus produces singlet oxygen.

[0048] In one embodiment, the bleaching medium comprises at least one second photosensitizer (A2) capable of generating singlet oxygen, preferably selected from the group consisting of: curcumin, flavin, riboflavin, phenoxazine, phenothiazine, phthalocyanine, naphthylphthalocyanine, xanthan, chlorophyll A, chlorophyll B, porphyrin, coumarin, pyrene, perylene, acridine orange, and tetrapyrrole.

[0049] Naphthalene benzophenones are 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.

[0050] In one embodiment, the naphthione is an unsubstituted naphthione or a naphthione substituted with at least one organic moiety, preferably a naphthione where at least one organic moiety is substituted at the 2 position of the naphthione ring, wherein the at least one organic moiety is 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.

[0051] In one embodiment, suitable flavins are disclosed in EP 2 723 342 A1, EP 2 723 743 A1, EP 2723 742 A1 and US 2019 / 0111168 A1.

[0052] In one embodiment, suitable curcumin is disclosed in US 2019 / 0111168 A1. Suitable curcumin derivatives and their preparation are also described in CA 2 888 140 A1, and suitable curcumin-3,5-diketone derivatives and their preparation are similarly described in EP 2 698 368 A1.

[0053] In one embodiment, phenoxazine is preferably nile blue.

[0054] In one embodiment, the phenothiazine is preferably selected from the group consisting of methylene blue, toluidine blue, 1,9-dimethylmethylene blue, and methylene green.

[0055] In one embodiment, phthalocyanine is preferably selected from the group consisting of zinc phthalocyanine, aluminum phthalocyanine, zinc phthalocyanine tetrasulfonate, and zinc tetra(p-trimethylammonium)phthalocyanine chloride.

[0056] In one embodiment, zeatin is preferably selected from the group consisting of: pyronin G, eosin B, eosin Y, and rose Bengal.

[0057] In one embodiment, the porphyrin is preferably selected from the group consisting of: 5,10,15,20-tetra(1-methyl-4-pyridinium)porphyrin-tetra(p-toluenesulfonate) and tetra(p-trimethylammoniumphenyl)porphyrin chloride.

[0058] In one embodiment, tetrapyrrole is preferably selected from the group consisting of: dihydroporphyrin, dihydroporphyrin E6, and chlorophyll.

[0059] In one embodiment, when exposed to electromagnetic radiation with wavelengths 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, at least one naphthalene-benzophenone (A) preferably generates singlet oxygen. The most suitable wavelength for the photosensitizer to generate singlet oxygen is selected based on the specific chemical properties of the photosensitizer.

[0060] In one embodiment, at least one naphthaleneacetone (A) is preferably present in an amount ranging from ≥0.01% by weight to ≤10.0% by weight, more preferably in an amount ranging from ≥0.10% by weight to ≤8.0% by weight, more preferably in an amount ranging from ≥0.15% by weight to ≤5.0% by weight, and most preferably in an amount ranging from ≥0.20% by weight to ≤3.0% by weight, based on the total weight of the bleaching medium.

[0061] In one embodiment, at least one naphthaleneacetone (A) is preferably dissolved in at least one polar solvent before being blended with the other components of the bleaching medium.

[0062] The ability of a solvent to dissolve a given substance (e.g., naphthalene-2-benzophenone) can be readily assessed by considering parameters according to the "Hansen system," described in "Hansen Solubility Parameters - A Users Handbook" (2000) published by CRC Press. According to the Hansen system, a solvent or solvent mixture can be described by three solubility parameters: δd (dispersion parameter), δp (polarity parameter), and δh (hydrogen bonding parameter).

[0063] In a preferred embodiment, at least one polar solvent is selected from the group consisting of: alkyl esters of fatty acids, such as methyl esters, ethyl esters, and isopropyl esters of fatty acids, such as methyl oleate, methyl palmitate, methyl laurate, isopropyl myristate, or isopropyl palmitate; alcohols, such as ethoxydiethylene glycol, 2-methoxyethanol, or 1-methoxy-2-propanol; and dimethyl sulfoxide and 1-methyl-2-pyrrolidone.

[0064] In a preferred embodiment, at least one polar solvent has a strength of δd ≥ 15.0 to ≤ 20.0 (MPa). 1 / 2 δp ≥ 2.0 to ≤ 28.0 (MPa) 1 / 2 and δh ≥ 5.0 to ≤ 13.0 (MPa) 1 / 2 The Hansen solubility parameter within the specified range.

[0065] In one embodiment, at least one solvent is preferably present in an amount ranging from ≥0.5% by weight to ≤5.0% by weight, and more preferably from ≥0.5% by weight to ≤2.0% by weight, based on the total weight of the bleaching medium.

[0066] The bleaching medium contains at least one persulfate (B). In one embodiment, the at least one persulfate (B) is selected from the group consisting of alkaline earth metal persulfates, alkali metal persulfates, and ammonium persulfate, which exhibits oxidizing activity, i.e., generates 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, the at least one persulfate (B) is preferably selected from the group consisting of ammonium persulfate, sodium persulfate, and potassium persulfate. Persulfates are generally present in particulate form with an average particle size ranging from ≥0.1 μm to ≤200 μm.

[0067] In one embodiment, at least one component (B) is preferably present in an amount ranging from ≥3.0% by weight to ≤30% by weight, more preferably from ≥5.0% by weight to ≤25% by weight, and even more preferably from ≥7.0% by weight to ≤20% by weight, based on the total weight of the bleaching medium.

[0068] 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 with at least one hydroxyl group. Preferred alkanolamines are selected from the group consisting of: monoethanolamine, 3-aminoprop-1-ol, 2-amino-1-propanol, 4-aminobut-1-ol, 5-aminopent-1-ol, 1-aminoprop-2-ol, 1-aminobut-2-ol, 1-aminopent-2-ol, 1-aminopent-3-ol, 1-aminopent-4-ol, 3-amino-2-methylprop-1-ol, 1-amino-2-methylprop-2-ol, 3-aminoprop-1,2-diol, and 2-amino-2-methylprop-1,3-diol.

[0069] In another embodiment, the bleaching medium contains other alkalizing agents, particularly inorganic alkalizing agents. The inorganic alkalizing agents considered 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.

[0070] In one embodiment, the bleaching medium comprises at least one alkalizing agent (C), which is sodium silicate.

[0071] In another embodiment, at least one component (C) is present in an amount ranging from ≥3.0 wt% to ≤20 wt%, preferably from ≥4.0 wt% to ≤15 wt%, and more preferably from ≥5.0 wt% to ≤12 wt%, based on the total weight of the bleaching medium. At least one component (C), such as sodium silicate, is an alkaline salt that provides an aqueous alkaline pH when the bleaching medium according to the currently claimed invention is mixed with an aqueous medium.

[0072] Because persulfate and hydrogen peroxide are relatively stable in acidic media, they may need to be activated at a neutral to alkaline pH to obtain sufficient formulation. Therefore, it is common practice to add at least one alkalizing agent (C), such as an alkali metal silicate and / or ammonium silicate, to the bleaching medium. Alkaline pH is an activating factor that enables oxidation by combining an oxidizing agent such as hydrogen peroxide with persulfate.

[0073] In one embodiment, the bleaching medium according to the currently claimed invention preferably comprises at least one additive (D) selected from the group consisting of: sources of carbonate, bicarbonate, or carbamate ions; aluminosilicates; surfactants; chelating agents; thickeners; fillers; amino acids; hydrolyzed proteins; fatty substances; saturated acyclic terpenes having 10 to 40 carbon atoms; C3-C20 monocarboxylic acids and C3-C10 dicarboxylic acids or tricarboxylic acids.

[0074] In another embodiment, at least one additive (D) is preferably present in an amount ranging from ≥2.0 wt% to ≤30 wt%, more preferably from ≥3.0 wt% to ≤25 wt%, even more preferably from ≥4.0 wt% to ≤20 wt%, even more preferably from ≥4.0 wt% to ≤18 wt%, most preferably from ≥4.0 wt% to ≤17 wt%, and particularly from ≥4.0 wt% to ≤15 wt%, based on the total weight of the bleaching medium.

[0075] In one embodiment, the source of carbonate, bicarbonate, or carbamate ions is preferably selected from the group consisting of sodium, potassium, guanidine, arginine, lithium, calcium, magnesium, barium, and ammonium salts of carbonate, carbamate, and bicarbonate ions. In another embodiment, the source of at least one carbonate, bicarbonate, or carbamate ion is preferably present in an amount ranging from ≥1.0 wt% to ≤10.0 wt%, more preferably from ≥2.0 wt% to ≤8.0 wt%, and even more preferably from ≥2.0 wt% to ≤6.0 wt%, based on the total weight of the bleaching medium. The source of carbonate, bicarbonate, or carbamate ions is a solid alkaline salt that provides an aqueous alkaline pH when the bleaching medium is combined with an aqueous medium.

[0076] In one embodiment, the aluminosilicate is preferably sodium aluminosilicate. In another embodiment, the aluminosilicate is preferably present in an amount ranging from ≥3.0 wt% to ≤15 wt%, more preferably from ≥4.0 wt% to ≤12 wt%, and even more preferably from ≥4.0 wt% to ≤10.0 wt%, based on the total weight of the bleaching medium.

[0077] In one embodiment, the bleaching medium according to the currently claimed invention preferably comprises a surfactant, more preferably an anionic surfactant, selected from the group consisting of salts of the following compounds (such as basic salts, e.g., sodium salts, ammonium salts, amine salts, amino alkoxides, 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, α-olefin sulfonates, alkane sulfonates; alkyl sulfosuccinates, alkyl ether sulfosuccinates, alkyl amide sulfosuccinates; alkyl sulfosuccinates; alkyl sulfoacetates; alkyl ether phosphates; acyl sarcosinates; acyl hydroxyethyl sulfonates; N-acyl taurates; and mixtures thereof. The alkyl or acyl groups of all these various compounds, for example, contain 8 to 24 carbon atoms, and the aryl groups are selected, for example, from phenyl and benzyl groups. Weak anionic surfactants, such as alkyl-D-galactoside uronic 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, such as those containing 2 to 50 ethylene oxide groups, and mixtures thereof, may also be used. Anionic derivatives of polysaccharides, such as carboxyl ethers of alkyl polyglucosides, may also be used.

[0078] In one embodiment, the surfactant is preferably present in an amount ranging from ≥1.0 wt% to ≤9.0 wt%, more preferably from ≥1.0 wt% to ≤5.0 wt%, and even more preferably from ≥1.0 wt% to ≤4.0 wt%, based on the total weight of the bleaching medium.

[0079] In one embodiment, the bleaching medium according to the currently claimed invention comprises an anionic surfactant, preferably selected from the group consisting of alkali metal and alkaline earth metal salts of laurate, myristate, palmitate, stearate or behenate, more preferably selected from the group consisting of sodium and potassium salts of laurate, palmitate or stearate.

[0080] In one embodiment, the bleaching medium preferably comprises a surfactant selected from the group consisting of nonionic surfactants, amphoteric or zwitterionic surfactants and cationic surfactants.

[0081] In one embodiment, the nonionic surfactant is selected from the group consisting of: fatty alcohol polyethylene glycol ethers, alkylphenol polyethylene glycol ethers, fatty acid polyethylene glycol esters, fatty acid amide polyethylene glycol ethers, fatty amine polyethylene glycol ethers, alkoxylated triglycerides, optionally partially oxidized alkyl (alken) oligoglycosides or alkyl (alken) polyglycosides or glucuronic acid derivatives, fatty acid-N-alkyl glucamides, protein hydrolysates (especially wheat-based plant products), polyol fatty acid esters, sugar esters, dehydrated sorbitol esters, polysorbate esters, and amine oxides.

[0082] Amphoteric surfactants are surfactants whose molecules contain at least one quaternary ammonium group and at least one -COO group. (-) or -SO3 (-) Surfactant compounds with functional groups. Particularly suitable zwitterionic surfactants are so-called betaines, such as N-alkyl-N,N-dimethylglycinine ammonium, for example cocoalkyldimethylglycinine ammonium, N-acylaminopropyl-N,N-dimethylglycinine ammonium, for example cocoylaminopropyldimethylglycinine ammonium, and 2-alkyl-3-carboxymethyl-3-hydroxyethylimidazoline and cocoylaminoethylhydroxyethylcarboxymethylglycinine salts containing 8 to 18 carbon atoms in the alkyl or acyl group.

[0083] Amphoteric surfactants are surfactant compounds that, in addition to C8 to C18 alkyl or acyl groups, contain at least one free amino group and at least one -COOH or -SO3H group in their molecule and are capable of forming an inner salt. Examples of suitable amphoteric surfactants are 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 to 18 carbon atoms in their alkyl groups.

[0084] Particularly suitable cationic surfactants are quaternary ammonium compounds, preferably ammonium halides, and more particularly ammonium chloride and ammonium bromide, such as alkyltrimethylammonium chloride, dialkyldimethylammonium chloride and trialkylmethylammonium chloride, for example cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and trioctylmethylammonium chloride.

[0085] Hydrogen peroxide readily decomposes upon contact with heavy metals such as iron, copper, and manganese, and may quickly become ineffective. This drawback is typically eliminated by incorporating chelating agents into the formulation. In one embodiment, the bleaching medium contains a chelating agent, preferably selected from the group consisting of: ethylenediaminetetraacetic acid (EDTA), ethylenediamine-N,N'-disuccinic acid (EDDS), ethylenediamine-N,N'-diglutarate (EDDG), 2-hydroxypropyldiamine-N,N'-disuccinic acid (HPDDS), N,N-dicarboxymethyl glutamate (GLDA), methylglycine-N,N'-diacetic acid (MGDA), glycamide-N,N'-disuccinic acid (GADS), ethylenediamine-N-N'-bis(o-hydroxyphenylacetic acid) (EDDHA), and dimethylglucosamine (DM). G), N-(1-carboxyethyl)iminodiacetic acid, methylglycine N,N-diacetic acid, diethylenetriaminepentaacetic acid (DTPA), ethylenedisulfonylalanine (EDC), N,N′-bis(2-hydroxybenzyl)ethylenediamine-N,N'-diacetic acid (HBED), ethylenediaminetris(methylenephosphonate), tetramethylethylenediamine (TMEDA), N,N,N′,N′-tetraethylethylenediamine (TEEDA), and their salts, more preferably, the chelating agent is selected from the group consisting of ethylenediaminetetraacetic acid (EDTA), ethylenediamine-N,N'-disuccinic acid (EDDS), and their salts. In the context of chelating agents, "the salts thereof" means all salts containing the same functional structure as the chelating agents they refer to, and includes 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 monoethanol ammonium salts, diethanol ammonium salts, triethanol ammonium salts, and mixtures thereof.

[0086] In one embodiment, the chelating agent is preferably present in an amount ranging from ≥0.1% by weight to ≤3.0% by weight, more preferably from ≥0.2% by weight to ≤2.0% by weight, and even more preferably from ≥0.3% by weight to ≤1.5% by weight, based on the total weight of the bleaching medium.

[0087] The bleaching medium according to the currently claimed invention preferably comprises at least one thickener. The thickener is typically water-soluble and imparts the desired semi-fluid to paste consistency to the bleaching medium. Typical thickeners include, but are not limited to, synthetic water-soluble polymers and naturally derived water-soluble polymers. In one embodiment, the bleaching medium according to the currently claimed invention comprises a thickener preferably selected from the group consisting of: cellulose derivatives, polyacrylic acid, acrylate copolymers, polysaccharide gums, xanthan gum, starch, guar gum, starch derivatives, alginate, and diallyl dimethylammonium acrylate polymers; more preferably selected from the group consisting of xanthan gum, starch, and alginate.

[0088] Exemplary embodiments of water-soluble synthetic polymer thickeners include polyvinylpyrrolidone, polyacrylic acid, polyacrylamide, non-crosslinked poly-2-acrylamidopropanesulfonic acid, acid-crosslinked poly-2-acrylamido-2-methylpropanesulfonic acid, and crosslinked poly-2-acrylamido-2-methylpropanesulfonic acid neutralized by an ammonia moiety. Further exemplary embodiments of synthetic water-soluble thickeners include those such as non-crosslinked poly-2-acrylamido-2-methylpropanesulfonic acid combined with hydroxyalkyl cellulose ethers or with poly(ethylene oxide). Examples of water-soluble thickeners derived from natural sources include, but are not limited to, polymers comprising at least one sugar unit. Exemplary examples of naturally derived thickeners include, but are not limited to, nonionic guar gum, semi-synthetic guar gum modified with C1-C6 hydroxyalkyl groups; microbial-derived biopolysaccharide gums, such as stearin or xanthan gum; gums derived from plant exudates, such as gum arabic, gum agar, gum arabic, gum arabic, astragalus gum, carrageenan, agar, and carob gum; pectin; alginate; starch, including, for example, rice starch, corn starch, potato starch, rapeseed starch, cassava starch, and their hydrolyzed derivatives; hydroxyalkyl (C1-C6) cellulose and carboxylalkyl (C1-C6) cellulose. Examples of water-soluble cellulose thickeners include, but are not limited to, hydroxyalkyl (C1-C6) cellulose, such as hydroxyethyl cellulose.

[0089] In one embodiment, the thickener is preferably present in an amount ranging from ≥0.5% by weight to ≤5.0% by weight, more preferably from ≥0.5% by weight to ≤6.0% by weight, and even more preferably from ≥1.0% by weight to ≤4.0% by weight, based on the total weight of the bleaching medium.

[0090] In one embodiment, the bleaching medium according to the currently claimed invention comprises a filler selected from the group consisting of kaolin, chlorophyllite clay, and sepiolite clay. In one embodiment, the filler is preferably present in an amount ranging from ≥0.5 wt% to ≤10.0 wt%, more preferably from ≥1.0 wt% to ≤8.0 wt%, and even more preferably from ≥1.0 wt% to ≤6.0 wt%, based on the total weight of the bleaching medium.

[0091] In one embodiment, the bleaching 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; more preferably, at least one amino acid selected from the group consisting of alanine, glycine, valine, and arginine; most preferably, at least one amino acid is alanine, glycine, valine, or arginine. In a preferred embodiment, the bleaching medium does not contain other amino acids. The at least one amino acid present in the bleaching medium of the currently claimed invention has oxidative stability in the bleaching medium, i.e., at least one amino acid is not oxidized by one of nucleophilic oxidation, electrophilic oxidation, or free radical oxidation reactions in the bleaching medium, or is oxidized only to a very small extent. In one embodiment, at least one amino acid is preferably obtained from a natural source, more preferably, at least one amino acid is obtained from a plant source.

[0092] In one embodiment, the amino acids are preferably present in an amount ranging from ≥0.05% by weight to ≤2.0% by weight, more preferably from ≥0.1% by weight to ≤1.5% by weight, even more preferably from ≥0.1% by weight to ≤1.3% by weight, and even more preferably from ≥0.1% by weight to ≤1.0% by weight, based on the total weight of the bleaching medium.

[0093] In one embodiment, the bleaching medium preferably comprises hydrolyzed proteins, 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, FKRestore, FK Protect Plus, and ProSina. TM .

[0094] In one embodiment, the bleaching medium according to the currently claimed invention comprises C3-C20 monocarboxylic acids, preferably selected from the group consisting of: propionic acid, butyric acid, valeric acid, isovaleric acid, hexanoic acid, isohexanoic acid, heptanoic acid, isohexanoic 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.

[0095] In one embodiment, the C3-C20 monocarboxylic acid is preferably present in an amount ranging from ≥0.05% by weight to ≤2.0% by weight, more preferably from ≥0.1% by weight to ≤1.5% by weight, even more preferably from ≥0.1% by weight to ≤1.3% by weight, and even more preferably from ≥0.1% by weight to ≤1.0% by weight, based on the total weight of the bleaching medium.

[0096] In one embodiment, the bleaching medium according to the currently claimed invention comprises C3-C10 dicarboxylic acids or tricarboxylic acids, preferably selected from the group consisting of: propanedioic 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.

[0097] In one embodiment, C3-C10 dicarboxylic acid or tricarboxylic acid is preferably present in an amount ranging from ≥0.05% by weight to ≤2.0% by weight, more preferably from ≥0.1% by weight to ≤1.5% by weight, even more preferably from ≥0.1% by weight to ≤1.3% by weight, and even more preferably from ≥0.1% by weight to ≤1.0% by weight, based on the total weight of the bleaching medium.

[0098] In one embodiment, the bleaching medium according to the currently claimed invention comprises at least one fatty substance selected from the group consisting of: liquid hydrocarbons, nonsiloxane oils of animal, plant, mineral or synthetic origin, fatty alcohols, fatty acid esters and / or fatty alcohol esters, nonsiloxane waxes, siloxanes and saturated acyclic terpenes.

[0099] More specifically, liquid hydrocarbons are selected from the following group:

[0100] - Straight-chain or branched, optionally cyclic C6-C16 alkanes, such as hexane, undecane, dodecane, tridecane, and isochain alkanes, such as isohexadecane, isododecane, and isodecane.

[0101] - Straight-chain or branched hydrocarbons of mineral, animal or synthetic origin having more than 16 carbon atoms, such as volatile or non-volatile liquid paraffins and their derivatives, petrolatum, liquid petrolatum, polydecene and hydrogenated polyisobutylene, such as Parleam®.

[0102] In a preferred embodiment of the currently claimed invention, the liquid hydrocarbon is selected from the group consisting of volatile or non-volatile liquid paraffin and liquid petrolatum.

[0103] In another embodiment of the currently claimed invention, the bleaching medium of the currently claimed invention comprises an adipose substance in an amount ranging from ≥1.0% by weight to ≤20.0% by weight based on the total weight of the bleaching medium.

[0104] In one embodiment, the bleaching medium of the currently claimed invention comprises at least one saturated acyclic terpene, which is a monoterpene, sesquiterpene, diterpene, triterpene, or tetraterpene. In another embodiment, the at least one saturated acyclic terpene is selected from the group consisting of 2,6-dimethyloctane, 2,6,10,15,19-pentamethyleicosane, farnesane, phytane, squalane, isosqualane, neosqualane, and lycopene. In yet another embodiment, the at least one saturated acyclic terpene is selected from the group consisting of squalane, isosqualane, and neosqualane; preferably, the at least one saturated acyclic terpene is squalane.

[0105] As used herein, “squalane” refers to an oil, also known as 2,6,10,15,19,23-hexamethyltetracosane. In one embodiment, squalane is a synthetic squalane obtained through chemical synthesis or a semi-synthetic squalane obtained by reducing 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.

[0106] In yet another embodiment, based on the total weight of the bleaching medium, at least one saturated acyclic terpene having 10 to 40 carbon atoms is preferably present in an amount ranging from ≥0.1 wt% to ≤15.0 wt%, more preferably from ≥0.5 wt% to ≤14.0 wt%, even more preferably from ≥0.5 wt% to ≤5.0 wt%, even more preferably from ≥1.0 wt% to ≤4.0 wt%, most preferably from ≥1.0 wt% to ≤3.0 wt%, and particularly from ≥1.0 wt% to ≤2.0 wt%.

[0107] In one embodiment, the bleaching 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 preferably present in an amount ranging from ≥1.0% by weight to ≤12% by weight, more preferably from ≥2.0% by weight to ≤6.0% by weight, based on the total weight of the bleaching medium.

[0108] In one embodiment, the bleaching medium according to the currently claimed invention comprises

[0109] (A) at least one naphthalene-based benzophenone, ≥0.5% by weight to ≤3.0% by weight

[0110] (B) At least one persulfate, ranging from ≥3.0% by weight to ≤30% by weight.

[0111] (C) At least one alkalizing agent, ranging from ≥3.0% by weight to ≤20% by weight.

[0112] (D) at least one additive (D) of ≥4.0% by weight to ≤25% by weight, selected from the group consisting of: sources of carbonate, bicarbonate, or carbamate ions; aluminosilicates; surfactants; chelating agents; thickeners; fillers; amino acids; hydrolyzed proteins; fatty substances; saturated acyclic terpenes having 10 to 40 carbon atoms; C3-C20 monocarboxylic acids and C3-C10 dicarboxylic acids or tricarboxylic acids; and

[0113] (E) at least one hydrogen peroxide source (E) in the range of ≥1.0 wt% to ≤12 wt%, preferably in the range of ≥2.0 wt% to ≤6.0 wt%, preferably hydrogen peroxide.

[0114] In one embodiment, the bleaching medium according to the currently claimed invention comprises

[0115] (A) at least one naphthalene-based benzophenone, ≥0.2% by weight to ≤3.0% by weight

[0116] (B) At least one persulfate, ranging from ≥3.0% by weight to ≤30% by weight.

[0117] (C) At least one alkalizing agent, ranging from ≥3.0% by weight to ≤20% by weight.

[0118] (D) at least one additive (D) from ≥4.0% by weight to ≤25% by weight, selected from the group consisting of: sources of carbonate, bicarbonate, or carbamate ions; aluminosilicates; surfactants; chelating agents; thickeners; fillers; amino acids; hydrolyzed proteins; fatty substances; saturated acyclic terpenes having 10 to 40 carbon atoms; C3-C20 monocarboxylic acids and C3-C10 dicarboxylic acids or tricarboxylic acids.

[0119] (E) ≥2.0 wt% to ≤6.0 wt% hydrogen peroxide, and

[0120] At least one polar solvent, comprising ≥0.5% by weight to ≤5.0% by weight, wherein the at least one polar solvent has a strength of δd ≥15.0 to ≤20.0 (MPa). 1 / 2 δp ≥ 2.0 to ≤ 28.0 (MPa) 1 / 2 and δh ≥ 5.0 to ≤ 13.0 (MPa) 1 / 2 Hansen solubility parameters within the specified range.

[0121] In one embodiment, the bleaching medium of the currently claimed invention is prepared by mixing bleaching 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), wherein at least one component (A) may be present in the bleaching powder or the aqueous medium, or at least one component (A) may be added to the bleaching powder or the aqueous medium. In one embodiment, the bleaching powder is preferably prepared by dispersing all compounds present in particulate form, i.e., at least one persulfate (B) and at least one alkalizing agent (C), in a fatty substance under mechanical action, wherein the other liquid components of the bleaching powder have been pre-dispersed or pre-mixed in the fatty substance.

[0122] In another embodiment, the bleaching powder is preferably prepared by extrusion, by introducing the liquid and solid phases of the bleaching powder into an extruder, and then mixing all components at a temperature of ≤25°C using a co-rotating twin-screw system including conveying and blending components.

[0123] Bleaching powder is used in combination with oxygen donors such as hydrogen peroxide to bleach hair.

[0124] Therefore, in another aspect, the currently claimed invention relates to a method for bleaching hair, which includes at least the following steps:

[0125] a) Apply the bleaching medium as described herein to dry or wet hair to obtain covered hair.

[0126] b) Exposing the covered hair to electromagnetic radiation with a wavelength 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.

[0127] c) Rinse the bleaching medium off the covered hair, and

[0128] d) Optionally dry the bleached hair.

[0129] In one embodiment, steps a) to d) can be repeated multiple times, for example, 2 or 3 times.

[0130] The bleaching medium is preferably applied to the hair using any number of application devices, with the main purpose of depositing the bleaching medium onto the hair in a small and dense manner to achieve the desired bleaching effect.

[0131] In one embodiment, the electromagnetic radiation is preferably generated 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.

[0132] In one embodiment, the energy density of the electromagnetic radiation is preferably ≥1 mW / cm². 2 Up to ≤70 mW / cm 2 Within the range, preferably ≥10 mW / cm 2 Up to ≤50 mW / cm 2 Within the range, or even more preferably within ≥20 mW / cm 2 Up to ≤40 mW / cm 2 Within the range.

[0133] In one embodiment, the pH of the bleaching medium is ≤7.0. The acidic pH ensures the stability of hydrogen peroxide in the bleaching medium. Preferably, the pH is 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 bleaching 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.

[0134] Oxidative hair dye compositions are typically sold in kits containing individually packaged components, such as in separate containers, for example, a dye or coloring component containing a dye coupling agent and a precursor; an aqueous hydrogen peroxide component; and a bleaching medium containing an alkalizing agent and persulfate. Therefore, in another aspect, the currently claimed invention also relates to a kit comprising i) an individually packaged oxidative component containing hydrogen peroxide; ii) an individually packaged coloring component containing at least one dye coupling agent and at least one dye precursor; and iii) an individually packaged bleaching medium as described herein.

[0135] In one embodiment, hair is bleached by applying a bleaching medium as described herein, and then dyed by applying a dyeing component comprising at least one dye coupling agent and at least one dye precursor. This combination of procedures allows for the use of lower amounts of dye coupling agent and dye precursor compared to procedures that include conventional bleaching and dyeing techniques.

[0136] In one embodiment, the dye precursor is selected from the group consisting of: toluene-2,5-diamine, p-phenylenediamine, n-phenyl-p-phenylenediamine, N,N-bis(2-hydroxyethyl)-p-phenylenediamine, hydroxyethyl-p-phenylenediamine sulfate, hydroxypropyl bis(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-2-hydroxyphenyl)methane, tetraaminopyrimidine, 2,5,6-triamino-4-pyrimidinol, 4,5-diamino-1-(2-hydroxyethyl)pyrazole, 2,3-diaminodihydroxypyrazolopyrazolone dimethylsulfonate, 4,5-diamino-1-hexylpyrazole, hydroxypropyl-p-phenylenediamine, dimethylpiperazine-onylaminopyrazolopyridine chloride hydrochloride, methylimidazolium-onylpropyl-p-phenylenediamine, hydroxyethoxyaminopyrazolopyridine, and salts thereof. Preferably, the oxidizing primary 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.

[0137] In one embodiment, the dye coupling agent is selected from the group consisting of: 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-ethyl Phenol, 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-naphthodiol, 2,7-naphthodiol, 1-acetoxy-2-methylnaphthol, 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-benzodioxane, indigo, hydroquinone, 4-formyl-1- Methylquinoline-p-toluenesulfonate and its salts. Preferably, the oxidative coupling 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-benzodioxane and its salts.

[0138] In one embodiment, the currently claimed invention relates to the use of at least one naphthaleneacetone for bleaching hair by generating singlet oxygen.

[0139] In one embodiment, the currently claimed invention relates to a naphthalene ketone in which an organic moiety is substituted at the 2 position of the naphthalene ketone ring, said organic moiety being substituted by at least one positively charged nitrogen atom and / or at least one neutral, protonable nitrogen atom and at least one negatively charged functional group (preferably at least one sulfonate group).

[0140] 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 substance.

[0141] A neutral, protonable nitrogen atom is a nitrogen atom that does not carry a net charge but can accept a proton (H⁺) and thus become positively charged.

[0142] Negatively charged functional groups, also known as anionic functional groups, are specific groups of atoms within a molecule that carry a net negative charge due to 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, the sulfonate group S(=O)2-O. - Sulfate group -OS(=O)2-O - Carboxylate group C(=O)-O - and phosphate group PO4 3- .

[0143] 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, saturated or unsaturated heteroalkyl, saturated or unsaturated cycloalkyl, saturated or unsaturated heterocycloalkyl, aryl, and heteroaryl. In each case, the aryl group preferably has at most four, more preferably at most three, and more preferably at most two cyclic rings. In each case, the aryl group further preferably has one ring. In each case, the heteroaryl group preferably has at most four, more preferably at most three, and more preferably at most two cyclic rings. In each case, the heteroaryl group further preferably has one ring.

[0144] In another preferred embodiment, the heteroaryl group has 5 to 20, preferably 5 to 13, more preferably 5 to 7 ring atoms in each case, comprising at least 1 carbon atom and 1 to 4 nitrogen atoms, and optionally 1 or 2 oxygen or sulfur atoms. In another preferred embodiment, the saturated or unsaturated heterocyclic alkyl group has 5 to 20, preferably 5 to 13, more preferably 5 to 7 ring atoms in each case, comprising at least 1 carbon atom and 1 to 4 nitrogen atoms, and optionally 1 or 2 oxygen or sulfur atoms.

[0145] In another preferred embodiment, the saturated or unsaturated alkyl group is selected from the group consisting of: methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, and n-octyl.

[0146] In a preferred embodiment, the naphthalene benzophenone ring is substituted at the 2-position with an organic moiety, said organic moiety being 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 (preferably at least one sulfonate group), selected from the group consisting of:

[0147] ●4-[dimethyl-[(1-oxonaphtho-2-yl)methyl]ammonium]butane-1-sulfonate

[0148] ●[(1-O-Naphthyl-2-yl)methylamino]methanesulfonate sodium salt

[0149] ●Sodium 4-[(1-oxonaphtho-2-yl)methylamino]butane-1-sulfonate

[0150] ●Sodium 2-[(1-oxonaphtho-2-yl)methylamino]ethanesulfonate

[0151] ●Sodium 3-[(1-oxonaphtho-2-yl)methylamino]propane-1-sulfonate

[0152] ●4-[diethyl-[(1-oxonaphtho-2-yl)methyl]ammonyl]butane-1-sulfonate

[0153] ●4-[4-[(E)-(1-oxonaphthyl-2-yl)methyliminomethyl]pyridin-1-onthiol-1-yl]butane-1-sulfonate

[0154] ●4-[3-methyl-2-[(1-oxonyl-2-yl)methylamino]imidazol-1-onthiol-1-yl]butane-1-sulfonate, and

[0155] ●4-[2-[(1-oxonyl-2-yl)methylamino]thiazolyl-3-on-3-yl]butane-1-sulfonate.

[0156] The invention currently claimed is associated with one or more of the following advantages.

[0157] ● Compared to conventionally bleached hair, hair exhibits less color cast when using the bleaching medium of the invention currently claimed for protection.

[0158] ●The bleaching medium of the currently claimed invention can bleach hair more effectively.

[0159] ●When using the bleaching medium of the currently claimed invention, the degree of damage to the hair is similar or less.

[0160] ● Hair feels softer when using a bleaching medium with a currently claimed invention compared to conventionally bleached hair.

[0161] The following list of embodiments is provided to further illustrate the present disclosure, but is not intended to limit the present disclosure to the specific embodiments listed below.

[0162] Example

[0163] 1. A bleaching medium comprising

[0164] (A) At least one photosensitizer capable of producing singlet oxygen.

[0165] (B) at least one persulfate, and

[0166] (C) at least one alkalizing agent, and

[0167] (E) At least one source of hydrogen peroxide.

[0168] 2. The bleaching medium according to Example 1, wherein the at least one photosensitizer (A) capable of generating singlet oxygen is selected from the group consisting of: naphthalene, curcumin, flavin, riboflavin, phenoxazine, phenothiazine, phthalocyanine, naphthyl phthalocyanine, xanthones, chlorophyll A, chlorophyll B, porphyrin, coumarin, pyrene, perylene, acridine orange, and tetrapyrrole.

[0169] 3. The bleaching medium according to Example 2, wherein the naphthalene-benzophenone is selected from naphthalene-benzophenones substituted with at least one organic moiety, wherein the at least one organic moiety is substituted with at least one positively charged nitrogen atom and at least one negatively charged functional group.

[0170] 4. The bleaching medium according to Example 2, wherein the phenoxazine is Nile blue.

[0171] 5. The bleaching medium according to Example 2, wherein the phenothiazine is selected from the group consisting of: methylene blue, toluidine blue, 1,9-dimethylmethylene blue and methylene green.

[0172] 6. The bleaching medium according to Example 2, wherein the phthalocyanine is selected from the group consisting of: zinc phthalocyanine, aluminum phthalocyanine, zinc tetrasulfonate phthalocyanine, and zinc tetra(p-trimethylammonium) phthalocyanine chloride.

[0173] 7. The bleaching medium according to Example 2, wherein the sulfadiazine is selected from the group consisting of: pyronin G, eosin B, eosin Y and Bengal rose red.

[0174] 8. The bleaching medium according to Example 2, wherein the porphyrin is selected from the group consisting of: 5,10,15,20-tetra(1-methyl-4-pyridinium)porphyrin-tetra(p-toluenesulfonate) and tetra(p-trimethylammoniumphenyl)porphyrin chloride.

[0175] 9. The bleaching medium according to Example 2, wherein the tetrapyrrole is selected from the group consisting of dihydroporphyrin, dihydroporphyrin E6 and chlorophyll.

[0176] 10. The bleaching medium according to any one of the foregoing embodiments, wherein when exposed to electromagnetic radiation with a wavelength in the range of ≥230 nm to ≤1000 nm, preferably in the range of ≥380 nm to ≤1000 nm, the at least one photosensitizer (A) capable of generating singlet oxygen generates singlet oxygen.

[0177] 11. The bleaching medium according to any one of the foregoing embodiments, wherein, based on the total weight of the bleaching medium, the at least one component (A) is present in an amount ranging from ≥0.01 wt% to ≤10.0 wt%, preferably in an amount ranging from ≥0.1 wt% to ≤8.0 wt%, more preferably in an amount ranging from ≥0.3 wt% to ≤5.0 wt%, and most preferably in an amount ranging from ≥0.5 wt% to ≤3.0 wt%.

[0178] 12. The bleaching medium according to any one of the foregoing embodiments, wherein the at least one persulfate (B) is selected from the group consisting of ammonium persulfate, sodium persulfate and potassium persulfate.

[0179] 13. The bleaching medium according to any one of the foregoing embodiments, wherein the at least one component (B) is present in an amount ranging from ≥3.0% by weight to ≤30% by weight, preferably from ≥5.0% by weight to ≤25% by weight, and more preferably from ≥7.0% by weight to ≤20% by weight, based on the total weight of the bleaching medium.

[0180] 14. The bleaching medium according to any one of the foregoing embodiments, wherein the at least one alkalizing agent (C) is selected from the group consisting of ammonia, alkanolamine and inorganic alkalizing agents.

[0181] 15. The bleaching medium according to claim 14, wherein the alkanolamine is selected from the group consisting of: monoethanolamine, 3-aminoprop-1-ol, 4-aminobut-1-ol, 5-aminopent-1-ol, 1-aminoprop-2-ol, 2-amino-1-propanol, 1-aminobut-2-ol, 1-aminopent-2-ol, 1-aminopent-3-ol, 1-aminopent-4-ol, 3-amino-2-methylprop-1-ol, 1-amino-2-methylprop-2-ol, 3-aminoprop-1,2-diol, and 2-amino-2-methylprop-1,3-diol.

[0182] 16. The bleaching medium according to claim 14, wherein the inorganic alkalizing agent is 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.

[0183] 17. The bleaching medium according to claim 16, wherein the inorganic alkalizing agent is selected from the group consisting of sodium silicate and sodium metasilicate.

[0184] 18. The bleaching medium according to any one of the foregoing embodiments, wherein the at least one component (C) is present in an amount ranging from ≥3.0% by weight to ≤20% by weight, preferably from ≥4.0% by weight to ≤15% by weight, and preferably from ≥5.0% by weight to ≤12% by weight, based on the total weight of the bleaching medium.

[0185] 19. The bleaching medium according to any one of the foregoing embodiments, 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.

[0186] 20. The bleaching medium according to Example 19, wherein the at least one hydrogen peroxide source (E) is hydrogen peroxide, which is preferably present in the range of ≥1.0% by weight to ≤12% by weight, preferably ≥2.0% by weight to ≤6.0% by weight, based on the total weight of the bleaching medium.

[0187] 21. The bleaching medium according to any one of the foregoing embodiments, wherein the bleaching medium comprises at least one additive (D) selected from the group consisting of: sources of carbonate or bicarbonate or carbamate ions, aluminosilicates, surfactants, chelating agents, thickeners, fillers, amino acids, hydrolyzed proteins, fatty substances, saturated acyclic terpenes having 10 to 40 carbon atoms, C3-C20 monocarboxylic acids and C3-C10 dicarboxylic acids or tricarboxylic acids.

[0188] 22. The bleaching medium according to Example 21, wherein the at least one additive (D) is present, based on the total weight of the bleaching medium, in an amount ranging from ≥2.0 wt% to ≤30 wt%, preferably from ≥3.0 wt% to ≤25 wt%, more preferably from ≥4.0 wt% to ≤20 wt%, even more preferably from ≥4.0 wt% to ≤18 wt%, most preferably from ≥4.0 wt% to ≤17 wt%, and particularly from ≥4.0 wt% to ≤15 wt%.

[0189] 23. The bleaching medium according to Example 21, wherein the source of the carbonate ions, bicarbonate ions, or carbamate ions is selected from the group consisting of sodium, potassium, guanidine, arginine, lithium, calcium, magnesium, barium, and ammonium salts of carbonate, carbamate, and bicarbonate ions.

[0190] 24. The bleaching medium according to any one of Examples 21 to 23, wherein the source of the at least one carbonate ion or bicarbonate ion or carbamate ion is present in an amount ranging from ≥1.0 wt% to ≤10.0 wt%, preferably from ≥2.0 wt% to ≤8.0 wt%, based on the total weight of the bleaching medium.

[0191] 25. The bleaching medium according to Example 21, wherein the aluminosilicate is sodium aluminosilicate.

[0192] 26. The bleaching medium according to any one of Examples 21 to 25, wherein the aluminosilicate is present in an amount ranging from ≥3.0% by weight to ≤15% by weight, preferably from ≥4.0% by weight to ≤12% by weight, and more preferably from ≥4.0% by weight to ≤10.0% by weight, based on the total weight of the bleaching medium.

[0193] 27. The bleaching medium according to any one of Examples 21 to 26, wherein the surfactant is selected from the group consisting of alkali metal salts and alkaline earth metal salts of laurate, myristate, palmitate, stearate or behenate.

[0194] 28. The bleaching medium according to any one of Examples 21 to 26, wherein the surfactant is selected from the group consisting of sodium and potassium salts of laurate, palmitate or stearate.

[0195] 29. The bleaching medium according to any one of Examples 21 to 28, wherein the surfactant is present in an amount ranging from ≥1.0 wt% to ≤9.0 wt%, preferably from ≥1.0 wt% to ≤5.0 wt%, and more preferably from ≥1.0 wt% to ≤4.0 wt%, based on the total weight of the bleaching medium.

[0196] 30. The bleaching medium according to any one of Examples 21 to 29, wherein the chelating agent is selected from the group consisting of: ethylenediaminetetraacetic acid (EDTA), ethylenediamine-N,N'-disuccinic acid (EDDS), ethylenediamine-N,N'-diglutarate (EDDG), 2-hydroxypropyldiamine-N,N'-disuccinic acid (HPDDS), N,N-dicarboxymethylglutamic acid (GLDA), glycine-N,N'-disuccinic acid (GADS), ethylenediamine-N-N'-bis(o-hydroxy) EDDHA, dimethylglucosamine (DMG), N-(1-carboxyethyl)iminodiacetic acid, methylglycine N,N-diacetic acid, diethylenetriaminepentaacetic acid (DTPA), ethylenedisulfonylalanine (EDC), N,N'-bis(2-hydroxybenzyl)ethylenediamine-N,N'-diacetic acid (HBED), ethylenediaminetris(methylenephosphonate), tetramethylethylenediamine (TMEDA), N,N,N′,N′-tetraethylethylenediamine (TEEDA), and their salts.

[0197] 31. The bleaching medium according to Example 30, wherein the chelating agent is selected from the group consisting of ethylenediaminetetraacetic acid (EDTA), ethylenediamine-N,N'-disuccinic acid (EDDS), and their salts.

[0198] 32. The bleaching medium according to any one of Examples 21 to 31, wherein the chelating agent is present in an amount ranging from ≥0.1% by weight to ≤3.0% by weight, preferably from ≥0.2% by weight to ≤2.0% by weight, and more preferably from ≥0.3% by weight to ≤1.5% by weight, based on the total weight of the bleaching medium.

[0199] 33. The bleaching medium according to any one of Examples 21 to 32, wherein the thickener is selected from the group consisting of: cellulose derivatives, polyacrylic acid, acrylate copolymers, polysaccharide gums, xanthan gum, starch, guar gum, starch derivatives, alginate, and diallyl dimethylammonium acrylate polymers.

[0200] 34. The bleaching medium according to Example 33, wherein the thickener is selected from the group consisting of xanthan gum, starch and alginate.

[0201] 35. The bleaching medium according to any one of Examples 21 to 34, wherein the thickener is present in an amount ranging from ≥0.5% by weight to ≤5.0% by weight, preferably from ≥0.5% by weight to ≤6.0% by weight, and more preferably from ≥1.0% by weight to ≤4.0% by weight, based on the total weight of the bleaching medium.

[0202] 36. The bleaching medium according to any one of Examples 21 to 35, wherein the filler is selected from the group consisting of kaolin, chlorophyll clay and sepiolite clay.

[0203] 37. The bleaching medium according to any one of Examples 21 to 36, wherein the filler is present in an amount ranging from ≥0.5% by weight to ≤10.0% by weight, preferably from ≥1.0% by weight to ≤8.0% by weight, and more preferably from ≥1.0% by weight to ≤6.0% by weight, based on the total weight of the bleaching medium.

[0204] 38. The bleaching medium according to any one of Examples 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.

[0205] 39. The bleaching medium according to any one of Examples 21 to 38, wherein the amino acid is present in an amount ranging from ≥0.05% by weight to ≤2.0% by weight, preferably from ≥0.1% by weight to ≤1.5% by weight, more preferably from ≥0.1% by weight to ≤1.3% by weight, and even more preferably from ≥0.1% by weight to ≤1.0% by weight, based on the total weight of the bleaching medium.

[0206] 40. The bleaching medium according to any one of Examples 21 to 39, wherein the hydrolyzed protein is selected from the group consisting of hydrolyzed keratin and hydrolyzed plant protein.

[0207] 41. The bleaching medium according to any one of Examples 21 to 40, wherein the C3-C10 dicarboxylic acid or tricarboxylic acid is selected from the group consisting of: propanedioic 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.

[0208] 42. The bleaching medium according to any one of Examples 21 to 41, wherein, based on the total weight of the bleaching medium, each of the C3-C20 monocarboxylic acid, C3-C10 dicarboxylic acid, or tricarboxylic acid is present in an amount ranging from ≥0.05% by weight to ≤2.0% by weight, preferably from ≥0.1% by weight to ≤1.5% by weight, more preferably from ≥0.1% by weight to ≤1.3% by weight, and even more preferably from ≥0.1% by weight to ≤1.0% by weight.

[0209] 43. The bleaching medium according to any one of Examples 21 to 42, wherein the saturated acyclic terpene having 10 to 40 carbon atoms is selected from the group consisting of squalane, isosqualane and neosqualane.

[0210] 44. The bleaching medium according to any one of Examples 1 to 43, comprising

[0211] (A) at least one photosensitizer capable of generating singlet oxygen, from ≥0.5% by weight to ≤3.0% by weight.

[0212] (B) At least one persulfate, ranging from ≥3.0% by weight to ≤30% by weight.

[0213] (C) at least one alkalizing agent of ≥20% to ≤32% by weight, and

[0214] (D) ≥2.0% by weight to ≤25% by weight of at least one additive (D), selected from the group consisting of: sources of carbonate or bicarbonate or carbamate ions, aluminosilicates, surfactants, chelating agents, thickeners, fillers, amino acids, hydrolyzed proteins, fatty substances, saturated acyclic terpenes having 10 to 40 carbon atoms, C3-C20 monocarboxylic acids and C3-C10 dicarboxylic acids or tricarboxylic acids.

[0215] 45. A method for bleaching hair, the method comprising at least the following steps:

[0216] a) Apply the bleaching medium according to any one of Examples 1 to 44 to the hair to obtain covered hair.

[0217] b) Exposing the covered hair to electromagnetic radiation with a wavelength in the range of ≥230 nm to ≤1000 nm, preferably in the range of ≥380 nm to ≤1000 nm.

[0218] c) Rinse the bleaching medium off the covered hair, and

[0219] d) Optionally dry the bleached hair.

[0220] 46. ​​The method according to Example 45, wherein in step b), the covered hair is exposed to electromagnetic radiation for a period of time ranging from ≥1 minute to ≤50 minutes.

[0221] 47. Use of at least one compound for bleaching hair by generating singlet oxygen, said at least one compound being selected from the group consisting of: naphthalene, curcumin, flavin, riboflavin, phenoxazine, phenothiazine, phthalocyanine, naphthylphthalocyanine, xanthones, chlorophyll A, chlorophyll B, porphyrin, coumarin, pyrene, perylene, acridine orange, and tetrapyrrole.

[0222] 48. The use according to Example 47, wherein the at least one compound is selected from naphthalene-benzophenone.

[0223] 49. A naphthalene benzophenone, wherein the 2-position of the naphthalene benzophenone ring is replaced by an organic moiety, said organic moiety being replaced by at least one positively charged nitrogen atom and at least one negatively charged functional group.

[0224] Although the invention currently claimed has been described with reference to specific embodiments thereof, certain modifications and equivalents will be apparent to those skilled in the art and are intended to be included within the scope of the invention currently claimed.

[0225] Example

[0226] The invention currently claimed is described in detail through the following non-limiting working examples. More specifically, the test methods specified below are part of the general disclosure of this application and are not limited to the specific working examples.

[0227] Material

[0228] Potassium persulfate can be purchased from United Initiators, Pullach, Germany.

[0229] ●Alkaline sodium silicate is available from BASF, Ludwigshafen / Rhine, Germany.

[0230] ●Ammonium persulfate can be purchased from Unite Initiator Company in Plach, Germany.

[0231] ●Basic magnesium carbonate is available from Dr. Paul Lohmann, Emmerthal, Germany.

[0232] ● Sodium stearate is available from Matrix Chemie.

[0233] ● Squalane, available from Aprinnova.

[0234] Xanthan gum can be purchased from KP Kelco, Großenbrode, Germany.

[0235] ●Seaweed gel, available from BASF in Ludwigshafen / Rheinland, Germany.

[0236] ●Disodium EDTA is available from BASF in Ludwigshafen / Rheinland, Germany.

[0237] ●D,L-malic acid is available from Merck Chemicals GmbH, Darmstadt, Germany.

[0238] ● Mineral oil, available from Panama PetroChem Ltd., India.

[0239] Synthesis of Naphthyl benzophenone

[0240] 1) Synthesis of naphthalene-4-benzophenone (IV):

[0241]

[0242] Malonic acid (4.0 equivalents, 53.3 g, 512 mmol) and 1-naphthaldehyde (I) (1.0 equivalents, 20.0 g, 128 mmol, 17.4 mL) were dissolved in pyridine (70 mL, 3.5 parts / volume) at room temperature, with a catalytic amount of piperidine added as a base (0.2 equivalents, 2.2 g, 26 mmol, 2.5 mL). The reaction mixture was then heated under reflux for 2 hours. The reaction mixture was cooled to room temperature, and then 250 mL of ice water was added with vigorous stirring, precipitating a white to beige residue. The yield was further increased when the pH was adjusted to 4 with concentrated hydrochloric acid. The residue was collected by vacuum filtration and washed with ice water to give intermediate (E)-3-(1-naphthyl)prop-2-enoic acid (II) as a light beige powder, in a yield of 93% (23.9 g, 119 mmol).

[0243] (E)-3-(1-naphthyl)prop-2-enoic acid (II) (1.0 equivalent, 3.0 g, 15 mmol) was suspended in dichloromethane (DCM) (30 mL, 10 parts / volume), a catalytic amount of DMF (100 μL) was added, and the mixture was cooled to 0 °C. Then, oxalyl chloride (1.5 equivalent, 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 formed. The reaction mixture was cooled to 0 °C again, and aluminum chloride (2.0 equivalent, 4.0 g, 30 mmol) was added in a single batch. The reaction mixture was slowly heated to room temperature and then further heated under reflux for 4 hours. 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 precipitate formed was collected by filtration, washed with water, and dried. The crude product was recrystallized in toluene to give pure naphthalene-4-benzophenone (IV) in 77% yield (2.1 g, 12 mmol).

[0244] 2) Synthesis of substituted naphthalene-phenylene rings

[0245] The scheme described in Godard et al., ACS Omega 2020, 5, 28264-28272, converts naphthalene-1-one to 2-(chloromethyl)naphthalene-1-one.

[0246] 2a) Synthesis of 4-[dimethyl-[(1-oxonaphtho-2-yl)methyl]ammonium]butane-1-sulfonate (VI):

[0247]

[0248] 0.23 g (1.00 mmol) of 2-(chloromethyl)naphthylbenzyl-1-one (V) was dissolved in 2 mL of DMF to form a clear yellow solution and heated to 85 °C. 0.90 g (5.00 mmol) of 4-(dimethylammonium)butane-1-sulfonate was dissolved in 3 mL of DMF and 5 mL of water in a separate container. 4-(dimethylammonium)butane-1-sulfonate is light-sensitive; therefore, the reaction was continued in the dark. The solution containing 4-(dimethylammonium)butane-1-sulfonate was slowly added to the solution of 2-(chloromethyl)naphthylbenzyl-1-one (V) in DMF at 85 °C. The reaction mixture was then further heated to 100 °C with stirring for 24 hours, forming a concentrated, deep yellow solution. The reaction mixture was then cooled to room temperature and diluted with 10 mL of DMF. Excess 4-(dimethylammonium)butane-1-sulfonate precipitated from the solution and was removed by filtration. The filter cake 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 crude precipitate was collected by filtration and further recrystallized with methanol to remove more polar impurities, yielding the desired 4-[dimethyl-[(1-oxonnaphthalene-2-yl)methyl-]ammonium]butane-1-sulfonate (VI) in 50% (0.19 g) yield.

[0249] 2b) Synthesis of 4-[(1-oxonaphtho-2-yl)methylamino]butane-1-sulfonic acid (VIII)

[0250]

[0251] 0.15 g (0.72 mmol) of 2-(aminomethyl)naphthylbenzene-1-one (VII) was dissolved at 50 °C in a mixture containing 4 mL of acetonitrile and 1 mL of methanol to form a clear, slightly reddish solution. 0.10 g (0.75 mmol) of oxothiacyclohexane 2,2-dioxide was added to this solution at 50 °C. The reaction mixture was then further heated to 70 °C for 12 hours. The solvent was evaporated under reduced pressure, and the precipitate formed was collected with 5 mL of diethyl ether and filtered. The residue was then washed with 5 mL of toluene to give the desired 4-[(1-oxonathylbenzene-2-yl)methylamino]butane-1-sulfonic acid (VIII) in 53% (0.13 g) yield.

[0252] 2c) Synthesis of sodium methanesulfonate (IX) [(1-oxonaphtho-2-yl)methylamino]

[0253]

[0254] 0.56 g (2.29 mmol) of 2-(aminomethyl)naphthylbenzyl-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 methanol solution of 2-(aminomethyl)naphthylbenzyl-1-one (VII) at 60 °C. The reaction mixture was then stirred at 60 °C for another 2 hours. The solvent was then carefully evaporated to obtain a deep red slurry, followed by the addition of 5 mL of water and stirring at room temperature. The reaction mixture was then heated to 60 °C, followed by the addition of 1 mL of ethyl acetate. The resulting yellow-orange crystals precipitated from the solution and were collected by filtration. The crystals were ground in a mortar by adding water and acetone. The solids formed were collected by filtration, while another portion of crystals precipitated from the filtrate. The collected solids were combined to give the desired compound [(1-oxonaphthylbenzyl-2-yl)methylamino]sodium methanesulfonate (IX) in a yield of 63% (0.47 g).

[0255] hair

[0256] Caucasian hair strands of 7.0 and 5.0 grade, in the form of strands 10 cm long and 1 cm wide, supplied by Kerling International Haarfabrik GmbH in Backnan, Germany.

[0257] Test methods

[0258] Combing force measurement

[0259] Various external influences, such as certain cosmetic treatments (bleaching, dyeing, perming), weather exposure, and frequent combing and brushing, can affect hair combability due to cuticle damage. Therefore, hair combability is a key parameter for describing hair quality / damage level and / or the effectiveness of conditioning or hair repair treatments. Most methods for determining combability are based on measuring the force required to pull a comb through a hair strand under defined conditions (Reference: CR Robbins, *Chemical and Physical Behavior of Human Hair*, 5th ed., p. 646 onwards, Springer-Verlag, Berlin Heidelberg, 2012. ISBN 978-3-642-25610-3). For this test, an automated device is used, in which the hair strand to be tested is removed from a storage chamber and fixed onto a force gauge. The hair strand is then automatically combed at a constant speed. For each combing action, the combing force is recorded as a function of the combing distance (hair strand length). For comparison purposes, for each product sample, at least three hair strands are combed 20 times each, and the average value is taken. The wet combing force is the average force along the hair strand. The lower the combing force, the better the combing ease.

[0260] Hunter Lab Color Measurement

[0261] The L*a*b* color values ​​obtained in the aforementioned examples were all measured using a Minolta Chromameter II colorimeter. The L value represents brightness (i.e., the higher the L value, the better the brightening effect), the a value is a measure of red content (i.e., the higher the a value, the higher the red content), and the b value is a measure of blue content in the color; the more negative the b value, the higher the blue content.

[0262] FT-IR damage measurement

[0263] Fourier transform infrared spectroscopy (FTIR) was used to assess damage to hair, a method established as suitable for studying the effects of damage to the keratin surface. (Strassburger, J., *Journal of the Soc. Cosmet Chem.*, 36, 61-74 (1985); Joy, M. and Lewis, DM, *International Journal of Cosmet Science*, 13, 249-261 (1991); Signori, V. and Lewis, DM, *International Journal of Cosmet Science*, 19, 1-13 (1997)). In particular, these authors demonstrated that the method is suitable for quantifying the amount of sulfoalanine. Cystine oxidation is generally considered a suitable marker for monitoring the overall oxidation of the keratin portion of the fiber. FT-IR is currently commonly used to measure sulfoalanine units.

[0264] Signori and Lewis (DM, *International Journal of Cosmetic Science*, 19, 1-13 (1997)) demonstrated that FT-IR using a diamond attenuated total internal reflection (ATR) cell is a sensitive and reproducible method for measuring the sulfoalanine content of individual fibers and fiber bundles. Therefore, the method for measuring the sulfoalanine content of multiple fiber bundles and intact hair bundles is based on the FTIR diamond cell ATR method used by Signori and Lewis (1997). A detailed description of the methods used to test different damage inhibitors is as follows:

[0265] The Perkin Elmer Spectrum® 1 Fourier Transform Infrared (FTIR) array, equipped with a diamond attenuated total internal reflection (ATR) cell, was used to measure sulfalanine concentration in mammalian or synthetic hair. In this method, hair bundles of various sizes and colors were used. To minimize variations in contact surface area between readings, the hair bundles were braided (approximately one strand per centimeter). The bleaching method described below was repeated for five cycles to simulate the state of hair after repeated bleaching cycles. After this treatment, four readings were taken for each hair bundle (at 1 / 3 and 2 / 3 of the way down along the bundle on both sides), and the average was calculated. Background values ​​were acquired every four readings using an ATR cell pressure of 1 N / m. The cell was cleaned with ethanol between readings, and contamination was checked using the instrument's monitoring ratio mode. A normalized double derivative analysis procedure was used, as specified by Signori and Lewis in 1997. The raw spectrum was first converted to absorbance and then normalized to 1450 cm⁻¹. -1 The band (characteristic and invariant protein CH2 stretching) was then used. The normalized absorbance was then subjected to two derivative calculations using a 13-point averaging method. The 1040 cm⁻¹ value was then used.-1 1450 cm⁻¹ of absorbance -1 The value of the normalized second derivative is taken as the relative concentration of sulfoalanine. Multiply this number by -1 × 10⁻⁶. 4 To convert it back to the appropriate unit.

[0266] preparation

[0267] A bleaching powder formulation sample was prepared by mixing all dry components together in a mixer for 5 minutes, with the mixing blades rotating at 3.5 rpm. The dust-removing component was added dropwise while the rotation speed was set at 3 rpm, and finally increased to 3.5 rpm for 6 minutes to ensure a homogeneous mixture.

[0268] Table 1. Bleaching Powder Formulations

[0269]

[0270] Table 2. Examples of oxidizing compositions (6% color developer)

[0271]

[0272] Table 3. Photosensitizer Formulations.

[0273] 20 mg of unsubstituted naphthylbenzophenone (IV) was dissolved in the following different amounts of solvent.

[0274]

[0275] Table 4. Dyeing Compositions

[0276]

[0277] bleaching method

[0278] In examples of the currently claimed invention, Welloxon® Perfect 6% or 9% oxidation formulation is used, which contains 6% or 9% hydrogen peroxide (a color developer from Wella Germany GmbH, Darmstadt, Germany) in an aqueous medium by weight of the total product.

[0279] As described above, the bleaching composition is prepared by mixing the bleaching powder described in Table 1 with a photosensitizer formulation and a commercially available color developer.

[0280] The following methods were used to evaluate the performance of each oxidative hair treatment composition.

[0281] 1. Use three natural Caucasian hair strands as described above.

[0282] 2. Apply a bleaching composition prepared using Welloxon® Perfect 9% and Blondor®.

[0283] 3. Mix 1 part of each bleaching powder with 1.5 parts of the oxidizing composition (Welloxon® Perfect 9%), then apply to the hairline with a brush and rub evenly. Apply 4 g of product per 1 g of hairline.

[0284] 3. Using a frequency of 415 nm and an energy density of 35 mW / cm² 2 Expose the hair strands to electromagnetic radiation, or place them in a 30°C oven for 40 minutes.

[0285] 4. Then, immerse the hair in water at 37±2℃ for 4 L / min. -1 Rinse for 2 minutes.

[0286] 5. Comb the hair strands twice (on both the coarse and fine teeth of the comb) and place them between the pre-moistened pieces of paper.

[0287] 6. Perform combing force measurements three times for each hair strand.

[0288] Example

[0289]

[0290] *Outside the scope of the currently claimed invention

[0291] The examples provided demonstrate that the addition of naphthoquinone IV or naphthoquinone IX during hair treatment enhances shine compared to treatments without naphthoquinone, as indicated by increased ΔL values. Specifically, the examples using naphthoquinone (Examples 3, 4, 7, and 8) showed ΔL values ​​ranging from 37.7135 to 43.6275, significantly higher than the control examples without naphthoquinone (Examples 1, 2, 5, and 6), which showed ΔL values ​​between 36.3245 and 40.208. Furthermore, FTIR measurements indicated that the damage induced by the naphthoquinone treatment and the control, as reflected by ΔFTIR values, was similar. For example, the ΔFTIR values ​​of naphthoquinone-treated hair ranged from 110.05 to 118.91, while the ΔFTIR values ​​of the control ranged from 103.11 to 111.53. This indicates that naphthalene enhances the shine of hair without significantly increasing oxidative damage to keratin structures, as measured by the formation of sulfoalanine.

Claims

1. A bleaching medium comprising (A) at least one photosensitizer capable of generating singlet oxygen, which is at least one phenalenone, (B) at least one persulfate salt, and (C) at least one alkalizing agent, and (E) at least one source of hydrogen peroxide.

2. The bleaching medium according to claim 1, wherein the bleaching medium further comprises at least one second photosensitizer (A2) capable of generating singlet oxygen, which is selected from the group consisting of curcumin, a flavin, a riboflavin, a phenoxazine, a phenothiazine, a phthalocyanine, a naphthalocyanine, a xanthene, chlorophyll A, chlorophyll B, a porphyrin, a coumarin, a pyrene, a perylene, an acridine orange and a tetrapyrrole.

3. The bleaching medium according to claim 1, wherein the at least one phenalenone is unsubstituted or selected from phenalenones substituted with at least one organic moiety, preferably phenalenones substituted with at least one organic moiety at the 2-position of the phenalenone ring, which at least one 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.

4. The bleaching medium according to claim 2, wherein the phenoxazine is nile blue.

5. The bleaching medium according to claim 2, wherein the phenothiazine is selected from the group consisting of methylene blue, toluidine blue, 1,9-dimethyl methylene blue and methylene green.

6. The bleaching medium according to claim 2, wherein the phthalocyanine is selected from the group consisting of zinc phthalocyanine, aluminum phthalocyanine, zinc tetrasulfonate phthalocyanine and zinc tetra(p-trimethylammonium) phthalocyanine chloride.

7. The bleaching medium according to claim 2, wherein the xanthene is selected from the group consisting of pyronine G, eosin B, eosin Y and rose Bengal.

8. The bleaching medium of claim 2, wherein the porphyrin is selected from the group consisting of 5,10,15,20-tetra(1 -methyl-4-pyridinium) porphyrin-tetra(p-toluenesulfonate) and tetra(p-trimethylammonium phenyl) porphyrin chloride.

9. The bleaching medium of claim 2, wherein the tetrapyrrole is selected from the group consisting of chlorin, chlorin e6 and bacteriochlorin.

10. The bleaching medium according to any one of the preceding claims, wherein the at least one phenalenone 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, more preferably in the range of > 380 nm to < 780 nm, even more preferably in the range of > 380 nm to < 490 nm, most preferably in the range of > 390 nm to < 430 nm.

11. The bleaching medium according to any one of the preceding claims, wherein the at least one component (A) is present in an amount ranging from > 0.01 wt.% to < 10.0 wt.%, based on the total weight of the bleaching medium, preferably in an amount ranging from > 0.10 wt.% to < 8.0 wt.%, more preferably in an amount ranging from > 0.15 wt.% to < 5.0 wt.%, most preferably in an amount ranging from > 0.20 wt.% to < 3.0 wt.%.

12. The bleaching medium according to any one of the preceding claims, wherein the at least one persulfate salt (B) is selected from the group consisting of ammonium persulfate, sodium persulfate and potassium persulfate.

13. The bleaching medium according to any one of the preceding claims, wherein the at least one alkalizing agent (C) is selected from the group consisting of ammonia, alkanolamines and inorganic alkalizing agents.

14. The bleaching medium according to any one of the preceding claims, wherein the at least one source of hydrogen peroxide (E) is selected from the group consisting of hydrogen peroxide, calcium peroxide, urea peroxide, perborate and percarbonate.

15. The bleaching medium according to any one of the preceding claims, wherein the bleaching medium comprises at least one additive (D) selected from the group consisting of a source of carbonate ions or bicarbonate ions or carbamate ions, aluminosilicates, surfactants, chelating agents, thickening agents, fillers, amino acids, hydrolyzed proteins, fatty substances, saturated acyclic terpene alkanes having 10 to 40 carbon atoms, C3-C20 monocarboxylic acids and C3-C10 dicarboxylic or tricarboxylic acids.

16. Bleaching medium according to any one of the preceding claims, wherein the bleaching medium comprises at least one polar solvent having a Hansen solubility parameter in the range of δd≥ 15.0 to ≤ 20.0 (MPa) 1 / 2 , δp≥ 2.0 to ≤ 28.0 (MPa) 1 / 2 and δh≥ 5.0 to ≤ 13.0 (MPa) 1 / 2 .​​​​​​ 17. The bleaching medium according to claim 16, wherein the at least one solvent is selected from the group consisting of methyl laurate, isopropyl myristate, ethoxydiglycol, 2-methoxyethanol, 1-methoxy-2-propanol, dimethyl sulfoxide and 1-methyl-2-pyrrolidone.

18. The bleaching medium according to claim 17 or 18, wherein the at least one solvent is present in an amount ranging from > 0.5 wt.% to < 5.0 wt.%, preferably in an amount ranging from > 0.5 wt.% to < 2.0 wt.%.

19. A method for bleaching hair, the method comprising at least the following steps: a) applying the bleaching medium according to any one of claims 1 to 18 to the hair to obtain covered hair, b) exposing the covered hair to electromagnetic radiation having a wavelength ranging from > 230 nm to < 1000 nm, preferably ranging from > 380 nm to < 1000 nm, more preferably ranging from > 380 nm to < 780 nm, even more preferably ranging from > 380 nm to < 490 nm, most preferably ranging from > 390 nm to < 430 nm, c) rinsing the bleaching medium off the covered hair, and d) optionally drying the bleached hair.

20. The method according to claim 19, wherein the energy density of the electromagnetic radiation is in the range of > 1 mW / cm2to < 70 mW / cm2, preferably in the range of > 10 mW / cm2to < 50 mW / cm2, even more preferably in the range of > 20 mW / cm2to < 40 mW / cm2.

21. Use of at least a perylenone for bleaching hair by generating singlet oxygen.

22. The use according to claim 21, wherein the at least one perylenone is selected from the group consisting of unsubstituted perylenone and perylenone substituted with at least one organic moiety, the at least one organic moiety being 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.

23. A perylenone substituted at the 2-position of the perylenone ring with one organic moiety, the at least one organic moiety being 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.

24. The perylenone according to claim 23, wherein the at least one negatively charged functional group is a sulfonate group.

25. The perylenone according to claim 23 or 24, selected from the group consisting of: • 4-[dimethyl-[(1-oxonaphthalenylene-2-yl)methyl]ammonio]butane-1- sulfonate • [(1-oxonaphthalenylene-2-yl)methylamino]methane sulfonic acid sodium salt • 4-[(1-oxonaphthalenylene-2-yl)methylamino]butane-1-sulfonic acid sodium salt • 2-[(1-oxonaphthalenylene-2-yl)methylamino]ethane sulfonic acid sodium salt • 3-[(1-oxonaphthalenylene-2-yl)methylamino]propane-1-sulfonic acid sodium salt • 4-[diethyl-[(1-oxonaphthalenylene-2-yl)methyl]ammonio]butane-1-sulfonate • 4-[4-[(E)-(1-oxonaphthalenylene-2-yl)methylimino-methyl]pyridin-1-ium-1- yl]butane-1-sulfonate • 4-[3-methyl-2-[(1-oxonaphthalenylene-2-yl)methylamino]imidazol-1-ium-1- yl]butane-1-sulfonate, and • 4-[2-[(1-oxonaphthalenylene-2-yl)methylamino]thiazol-3-ium-3-yl]butane-1- sulfonate.

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