Hair care agent, in particular temporary or oxidative hair dye, containing water-insoluble lignin particles

Abstract

The present invention relates to an agent for treating keratin fibres, in particular human hair, comprising ultrafine water-insoluble lignin particles and a carrier substance. The invention also relates to an agent for temporarily dyeing keratin fibres in the additional presence of colour pigments and to the use for selected hair dyeing methods. The invention ultimately relates to a method for temporarily changing the colour and shape of hair using the agent according to the invention. The present invention also relates to an oxidation dye for dyeing keratin fibres, in particular human hair, containing coupler components and developer components in a cosmetically acceptable carrier, wherein at least one lignin in the form of water-insoluble lignin particles is contained as the coupler component, which lignin particles have an average particle size D50 of 100 nm to 100 µm. The invention also relates to a method for dyeing keratin fibres using the oxidation dye according to the invention. The invention also relates to the use of water-insoluble lignin particles as the coupler component in an oxidation dye for dyeing keratin fibres.

Description

[0001] P93087WO August 11, 2025

[0002] Viering, Jentschura & Partner mbB

[0003] Hair care products, in particular temporary or oxidative hair dyes, containing water-insoluble lignin particles

[0004] The present invention relates to a composition for treating keratinous fibers, in particular human hair, comprising ultrafine water-insoluble lignin particles and a carrier substance. The invention further relates to a composition for temporarily dyeing keratinous fibers in the additional presence of color pigments and its use in selected hair coloring processes. The invention further relates to a method for temporarily coloring and reshaping hair using the composition according to the invention. The present invention also relates to an oxidation dye containing water-insoluble lignin particles as a coupler component. The invention further relates to a method for dyeing keratinous fibers using the oxidation dye according to the invention. Finally, the invention relates to the use of water-insoluble lignin particles as a coupler component in an oxidation dye for dyeing keratinous fibers.

[0005] Background of the invention

[0006] The cosmetic treatment of skin and hair is an important part of personal hygiene. Today, human hair is treated in a variety of ways with hair cosmetic preparations. These include cleansing the hair with shampoos, conditioning and regenerating it with conditioners and treatments, as well as bleaching, coloring, and styling the hair with dyes, tints, perming solutions, and styling products. Products for changing or toning the color of the hair and hair styling play a particularly important role.

[0007] Hair is frequently dyed with synthetic dyes to enhance its appearance or as a fashion statement. Hair coloring is one of the oldest cosmetic procedures, reflecting an ongoing desire to alter one's natural hair color. As a result, hair dye manufacturing has evolved into a multinational, multibillion-dollar industry over the past few decades. The majority of revenue (approximately 90%) comes from the sale of permanent hair coloring products, which owe their popularity to their long-lasting effects, ease of use, and versatility, allowing for the creation of virtually any color.

[0008] Due to the increasing aging and graying of the world's population, the demand for these products has risen rapidly, a trend that is likely to continue in the future. P93087WO August 11, 2025

[0009] Viering, Jentschura & Partner mbB

[0010] The methods used in hair coloring have unique characteristics that distinguish them from, for example, textile dyeing. Since it is a process performed on the human head, the hair must not be colored above 40°C, the coloring time typically does not exceed approximately 40 minutes, and the liquid-to-fiber ratio (1-2:1) is low. In this case, the ratio refers to the volume of the wet hair coloring solution compared to the weight of the hair to which it is applied.

[0011] The coloring must not impair the natural texture or shine of the hair, nor stain the scalp. If the color is to be long-lasting and not just temporary, it must be resistant to air, light, friction, sweat, and chlorinated water, and must not be affected by other hair treatments. Crucially, the coloring process must be toxicologically safe. Human hair grows an average of approximately 0.3 mm per day, with the growth cycle lasting about 7 years before the hair falls out. Therefore, the use of the term "permanent" to describe the longest-lasting hair coloring effect is limited by this characteristic, as a new treatment is required every 4 to 6 weeks to cover new growth.

[0012] Depending on the desired result, a professional hairstylist knows various coloring systems for changing hair color. For permanent, intense colorations with good colorfastness and gray coverage, oxidation dyes are primarily used. These dyes typically contain oxidation dye precursors, so-called developer components and coupler components, which react with oxidizing agents such as hydrogen peroxide to form the actual dyes. Oxidation dyes are characterized by very long-lasting color results.

[0013] The developer components usually consist of primary aromatic amines with an additional free or substituted hydroxy or amino group located in the para or ortho position, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives, as well as 2,4,5,6-tetraaminopyrimidine and its derivatives.

[0014] Specific examples include p-phenylenediamine, p-toluenediamine, 2,4,5,6-tetraaminopyrimidine, p-aminophenol, N,N-bis(2-hydroxyethyl)-p-phenylenediamine, 2-(2,5-diaminophenyl)-ethanol, 2-(2,5-diaminophenoxy)-ethanol, 1-phenyl-3-carboxyamido-4- P93087WO 11 August 2025

[0015] Viering, Jentschura & Partner mbB amino-pyrazolone-5, 4-amino-3-methylphenol, 2-aminomethyl-4-aminophenol, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, 2,5,6-triamino-4-hydroxypyrimidine and 1 ,3-N,N'-Bis(2-hydroxyethyl)-N,N'-bis(4-aminophenyl)-diamino-propan-2-ol.

[0016] The coupler components typically used are m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones, and m-aminophenols. Particularly suitable coupler substances include 1-naphthol, 1,5-, 2,7-, and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 1-phenyl-3-methyl-pyrazolone-5, 2,4-dichloro-3-aminophenol, 1,3-bis-(2,4-diaminophenoxy)propane, 2-chlororesorcinol, 4-chlororesorcinol, 2-chloro-6-methyl-3-aminophenol, 2-methylresorcinol, 5-methylresorcinol, and 2-methyl-4-chloro-5-aminophenol.

[0017] Good oxidative dye precursors should primarily meet the following requirements: During oxidative coupling, they must produce the desired color nuances with sufficient intensity and fastness. Furthermore, they must have good adhesion to the fiber, and in the case of human hair, in particular, there should be no noticeable differences between damaged and newly grown hair (equalizing ability). They should be resistant to light, heat, perspiration, friction, and the effects of chemical reducing agents, such as permanent wave solutions. Finally, if used as a hair dye, they should not excessively stain the scalp, and above all, they should be toxicologically and dermatologically safe.Furthermore, the achieved coloring through bleaching should be easily removable from the hair if it does not meet the individual wishes of the person and needs to be reversed.

[0018] It is generally not possible to achieve a natural-looking hair color using only a single developer component or a specific coupler / developer combination. Therefore, in practice, combinations of different developer and / or coupler components are typically used. Consequently, there is a constant need for new, improved dye components that are also safe from a toxicological and dermatological perspective.

[0019] However, modern fashion trends also demand color effects that remain on the hair for a short period of time and are subsequently washed out. P93087WO August 11, 2025

[0020] Viering, Jentschura & Partner mbB states that direct dyes cannot be completely removed from the hair with a single shampoo. Direct dyes diffuse more or less strongly into the hair fiber and persist there for several shampoos; therefore, this class of dye is not well suited for completely removing the color effect.

[0021] For temporary hair color changes, the use of color pigments is common. Color pigments are generally understood to be insoluble, coloring substances. These are present in the coloring formula as small, undissolved particles; these particles simply adhere to the outside of the hair fiber. They remain there until the next shampooing and can be completely removed by shampooing. Various products of this type are available on the market under names such as hair chalk and hair mascara.

[0022] Since hair chalk and hair mascara can be removed by shampooing, they are generally designed as leave-on products. It is particularly advantageous for users of a leave-on product if they can simultaneously achieve a temporary hair style along with the temporary color change. Temporary styles include curls, straightening, backcombing, or styling products. These temporary styles can be achieved using styling products such as hairsprays, waxes, gels, mousse, blow-dryers, styling creams, volumizing powders, and so on.

[0023] Temporary shaping is also referred to as hair styling or styling; shaping agents are also referred to as styling agents.

[0024] Products that allow simultaneous coloring and shaping are already known from the prior art. For example, WO 99 / 20230 A2 describes hair mascara products containing pigments together with nonionic polymers and high-melting-point waxes.

[0025] WO 2014 / 146818 A1 also reveals styling products with pigments characterized by the presence of solid fatty alcohols and waxes.

[0026] The fat and wax components in these products are primarily used to adjust the drying time, giving the consumer the feeling of dry hair, while the mascara applied to the hair retains some residual moisture, keeping the hairstyle manageable and combable. P93087WO August 11, 2025

[0027] Viering, Jentschura & Partner mbB

[0028] However, with leave-in products, a common problem is that the hair is often weighed down by the presence of oils. This creates the visual impression of "greasy hair," and the hold of these products is comparatively poor. Therefore, there is still room for improvement in both coloring and styling products.

[0029] Many conventional hair dyes also contain ingredients that are problematic for health, which can be absorbed into the body through the skin, especially the scalp, and can lead to negative side effects.

[0030] Therefore, especially with temporary hair care products, hair dyes based on natural ingredients are desirable, as they avoid such negative side effects as much as possible. However, conventional hair dyes based on natural pigments often contain inferior ingredients, are frequently not certified, have unsatisfactory and insufficient color effect and coverage, and are usually inadequate in application and handling.

[0031] These problems often deter users. In particular, difficulties with second colorings, excessively long processing times, poor consistency of the hair dye, and an uneven color result are common complaints, often leading to the use of hair dyes based on synthetic rather than natural ingredients, with the previously discussed health problems being consciously accepted as a lesser evil.

[0032] Therefore, there is a need for new hair care and hair coloring products with beneficial properties and, especially in the case of temporary hair coloring products, that these are based on natural ingredients.

[0033] The present invention is based on the objective of improving the state of the art or offering an alternative to it.

[0034] These and other objectives of the present invention can be achieved by a means for treating keratinous fibers as described in the present invention and defined in the claims, or by an oxidation dye for dyeing keratinous fibers as described in the present invention and defined in the claims. P93087WO August 11, 2025

[0035] Viering, Jentschura & Partner mbB

[0036] Advantageous embodiments of the invention are defined in the corresponding dependent claims.

[0037] Summary of the invention

[0038] According to a first aspect of the present invention, the stated problem is solved by a means for the treatment of keratinous fibers, in particular human hair, comprising:

[0039] (a) Lignin in the form of water-insoluble lignin particles having a mean particle size D50 of 100 nm to 100 pm, preferably of 5 to 30 pm and particularly preferably of 10 to 15 pm; and

[0040] (b) at least one particle-shaped carrier material that is solid under normal conditions or at least one liquid or semi-solid carrier material.

[0041] Surprisingly, it has been shown that these tasks can be solved by using water-insoluble lignin particles in combination with a similarly particulate carrier or a liquid or semi-solid carrier.

[0042] The first essential component of the invention is the agent for treating keratinous fibers, which contains lignin in the form of water-insoluble lignin particles with a mean particle size D50 of 100 nm to 100 pm.

[0043] These lignin particles show surprisingly good adhesion to keratin fibers and especially human hair, thus allowing the product to be used as a so-called "leave on" or "leave in" hair treatment product.

[0044] With a size greater than 100 nm, the particles are not considered to be among the nanomaterials that pose a health risk.

[0045] In their experiments, the inventors surprisingly found that the lignin, together with a carrier substance (and the optionally included inorganic and organic color pigments), adheres to both undamaged and damaged hair through a physical interaction and is abrasion-resistant when the inventive coloring is fixed by a few sprays of hairspray, treatment with hair glow, shine spray or a biopolymer solution or spray solution.

[0046] The composition according to the invention for treating keratinous fibers, particularly when used as a temporary hair dye, can be easily fixed by biopolymers acting as film formers. These can be found in P93087WO 11 August 2025

[0047] Viering, Jentschura & Partner mbB recommends that the hair treatment product be included or applied subsequently, preferably by spraying. The use of galactomannans such as tara gum, xanthan gum, fenugreek gum, guar gum, konjac gum, carob gum, cassia gum, locust bean gum, agar-agar, dextrins, gelatin, gellan gum, succinoglycan gum, scleroglucan, tragacanth, gum arabic, pectins, carrageenans, alginic acid and / or salts of alginic acid, and combinations thereof, has proven advantageous. These also act as an anti-pollution protection for the hair, insofar as they reduce the adhesion of environmental particles such as fine dust or pollen. Tara gum (Caesalpinia spinosa gum), xanthan gum, or a combination thereof is particularly preferred.

[0048] The lignin particles predominantly used according to the invention are also hydrophobic on the surface, like undamaged hair. Damaged hair becomes increasingly hydrophilic due to the loss of 18-methyleicosanoic acid (18-MEA) and the formation of cysteic acid. Therefore, lignin particles with moderate hydrophobicity or more hydrophilic properties can also be used for damaged hair. The relative hydrophobicity or relative hydrophilicity of lignin depends on the type of lignin-containing raw material source, i.e., on the chemical composition of the lignin in wood, straw, or grasses, the residual cellulose and hemicellulose content, and the processing method.

[0049] Due to their ability to absorb UV rays, the lignin particles can act as a sunscreen for the hair and the underlying skin areas and can also enhance the UV filtering effect of other UV filters contained within (so-called SPF booster effect).

[0050] Lignin is a free radical scavenger and antioxidant with antimicrobial properties, thus contributing to the protection of hair and scalp. Furthermore, lignin can bind lipophilic substances such as fats and oils, making it beneficial for oily hair and scalp.

[0051] Within the scope of the invention, it has surprisingly been shown that lignin particles with the particle size according to the invention can exhibit particularly advantageous properties for hair treatment products. Among other things, these products for treating keratin fibers exhibit good application and spreadability and a pleasant hair feel, resulting in a comfortable hair texture and maintaining shine and dry combability. P93087WO August 11, 2025

[0052] Viering, Jentschura & Partner mbB

[0053] In particular, a very good consistency of the texture and spreadability of the dyed hair and a very good shine and conditioning effect are achieved.

[0054] Lignin is the largest natural, renewable source of aromatic compounds. However, the lignin produced in paper mills is currently hardly used as a material, but is mostly burned for energy production. The lignin used in this invention comes primarily from biorefineries for ethanol production or is derived from residual wood.

[0055] Depending on the starting material (hardwood, softwood, grasses), lignin particles possess varying degrees of inherent color and can therefore be used as temporary dyes. The different lignin particles or colloidal lignin particles used according to the invention have a yellowish-brown, reddish-brown, and brown inherent color. A wide range of different colors can be achieved by adding further color pigments.

[0056] Lignin particles can be produced without the use of strong acids / bases and without the use of solvents, thus representing a natural and environmentally friendly ingredient with known positive properties, which is biodegradable and an alternative to fossil chemicals such as microplastics.

[0057] The second component of the agent for treating keratinous fibers contains at least one solid, particulate carrier or at least one liquid or semi-solid carrier.

[0058] This substance serves as an inert carrier for the lignin particles and, when a solid, particulate carrier is used, ideally has better flow properties than lignin in the common powdered bulk material. Lignin particles with a certain surface roughness, applied to the hair without an inert carrier, can lead to a rather woody feel and static electricity, which can cause undesirable frizz and flyaway. The adhesion of lignin particles to the hair also results in film formation, leading to a desired increase in volume of the treated hair strands. The inert carrier prevents static electricity, the woody effect, and the frizz and flyaway effect. It ideally has good adhesion to hair and, additionally, advantageously possesses hydrophobic and oil-adsorbing properties.However, hydrophilic carriers are also compatible with lignin. The volume-enlarging P93087WO 11 August 2025.

[0059] Viering, Jentschura & Partner mbB

[0060] The effect of a silicone-free volumizing powder is retained when combining the lignin particles with the inert carrier substance.

[0061] Furthermore, the agent for treating keratinous fibers, when used as a temporary dye, can achieve good coloring, significant volume when using the hair dye according to the invention, excellent hair structure, and very good washability and removal of the hair dye according to the invention. It is particularly noteworthy that the hair treatment agent can be applied quickly and easily to dry hair, resulting in so-called instant coloring, in which the existing hair color, even in medium and dark hair colors, can be lightened by the agent according to the invention without the use of oxidative hair dyes. The hair treatment agent can therefore be used as a trial hair color by individuals who are still undecided before a permanent change of hair color, in order to temporarily test the coloring. A temporary second coloring is also easily possible with the hair treatment agent.

[0062] As has been shown, the hair treatment product according to the invention is widely applicable: It can be used for both hair care and hair coloring.

[0063] It can also be combined with known ingredients for hair treatment products and thus specifically adapted to the respective application.

[0064] The invention in detail

[0065] The agent for treating keratinous fibers, as described in the first aspect, contains lignin in the form of water-insoluble lignin particles, with a mean particle size D50 of between 100 nm and 100 pm. According to this defined particle size, the lignin particles are present as a powder or, in the case of colloidal lignin particles, as an aqueous dispersion.

[0066] It is preferred to use either lignin particles with a mean particle size D50 of 5 pm to 100 pm, preferably with a particle size distribution D90 of less than 25 pm, or colloidal lignin particles with a mean particle size of 100 to 500 nm. A combination of these two lignin particle types is also possible.

[0067] Colloidal lignin particles are defined as lignin particles that, as an aqueous dispersion, form a colloidal solution due to the uniform distribution of the particles. P93087WO August 11, 2025

[0068] Viering, Jentschura & Partner mbB

[0069] The colloidal lignin particles preferably represent water-insoluble, sulfur-free lignin particles.

[0070] These particles are preferably obtained from an organosolv lignin. Methods for their production are described, for example, in WO 2020 / 000008 A1.

[0071] It has been shown that lignin particles of this size are both easy to process and exhibit beneficial adhesion to the hair fibers. Hair texture, shine, and combability are preserved by the particles.

[0072] The inventive agent for treating keratinous fibers is particularly suitable for fine, smooth, thick, smooth, wavy, brittle, curly, very curly, permed and frizzy hair (Afro hair), for oily, normal or dry hair, as well as for beard hair, eyelashes and eyebrows, for hair that looks weighed down by a normal hair mascara or for which this is not applicable, and which does not need to be combed when using the inventive agent suitable for the hair type.

[0073] The agent according to the invention for the treatment of keratinous fibers is also suitable as a pretreatment for dry haircuts when bactericidal and fungicidal active ingredients are added, ensuring that a hygienically perfect haircut can be carried out even without washing the hair.

[0074] The properties of lignin can vary considerably and depend on the plant source and the isolation method. Depending on the plant source and isolation method, the lignin particles are soluble in different solvents. According to the invention, the lignin particles are water-insoluble.

[0075] Materials are considered “water-insoluble” if, when 100 g of the material is mixed with 100 g of deionized water and filtered at 20 °C under atmospheric pressure through a filter with a pore size of 0.2 pm to recover the liquid filtrate, after evaporation of 100 g of the liquid filtrate at 95 to 100 °C and ambient pressure, less than or equal to 0.1 g of recovered solid is obtained.

[0076] Furthermore, the agent for treating keratinous fibers contains at least one particle-shaped carrier substance that is solid under normal conditions, or at least one liquid or semi-solid carrier substance. The carrier substance serves the purpose of ensuring that the P93087WO 11 August 2025

[0077] Viering, Jentschura & Partner mbB

[0078] Lignin particles adhere to the hair surface together with the carrier substance in the form of physical adhesion.

[0079] Surprisingly, the amount and type of carrier substance can be used to regulate hair texture, volume, and dyeability. It has also been found that the carrier substance prevents static electricity from building up in the hair due to the lignin particles. Furthermore, the carrier substance content can regulate the moisture content and overall quality of the formula during prolonged storage.

[0080] In a preferred embodiment, the solid carrier material is an inert carrier material. An inert carrier material is one that, under normal conditions, does not react with the lignin and other ingredients commonly used in hair cosmetics as potential reaction partners, or reacts only to a negligible extent.

[0081] Under normal conditions, this refers to a standard temperature of 25°C and a standard pressure of 1.013 bar.

[0082] The two essential components of the aspect, lignin particles and solid carrier material, are preferably present in a homogeneous mixture.

[0083] The two essential components of the aspect, lignin particles and liquid carrier, are preferably present as a dispersion in a finely divided mixture of the lignin particles in the liquid solvent, which is preferably an aqueous solvent.

[0084] In one embodiment, the liquid carrier is a solvent selected from the group consisting of water, alcohol, oil, or a mixture thereof. In a preferred embodiment, the liquid carrier is an aqueous or alcoholic solution.

[0085] The two essential components of the aspect, lignin particles and semi-solid carrier, are preferably present as a dispersion in a finely divided mixture of the lignin particles in the semi-solid formulation, which is preferably a thickened aqueous solvent, a semi-solid lipophilic preparation or an emulsion.

[0086] In one embodiment, the semi-solid carrier is an aqueous or alcoholic solution thickened with a thickening agent, resulting in a highly viscous solution up to P93087WO 11 August 2025

[0087] Viering, Jentschura & Partner mbB results in a gelatinous mixture. In another preferred embodiment, the semi-solid carrier substance is a so-called hair butter, a leave-in hair mask, or an emulsion.

[0088] In a preferred embodiment, the lignin particles consist of lignin with a proportion of 75 to 95 wt.% and cellulose and hemicellulose with a proportion of 5 to 25 wt.%.

[0089] In one embodiment, the lignin particles contained in the composition according to the invention for treating keratinous fibers have a cellulose and hemicellulose or C5 and C6 monosaccharide content of less than 10% by weight. Depending on the starting material and isolation method, these sugars originate from the plant-based starting material and / or from the enzymatic treatment of the material, which is carried out in particular by a cellulase. It has been shown that a total C5 / C6 monosaccharide content of less than 10% significantly reduces the stickiness of the lignin.

[0090] Prominent C5 monosaccharides are arabinose and xylose, and prominent C6 monosaccharides are glucose, mannose, and galactose, so that the content of C5 and C6 monosaccharides can be approximately characterized by adding the contents of the five aforementioned sugars.

[0091] In another embodiment, the lignin particles have a bulk density of 425 to 500 kg / m³. 3 Bulk density is the ratio of a material's mass to its volume, including the pores within the grains and the spaces between them. Bulk density depends primarily on the size and shape of the individual particles. As the particle diameter decreases, the bulk density also changes.

[0092] In one embodiment, the lignin particles have a knock density of 500 to 550 kg / m³. 3When determining the tap density, a powder bed is compacted by impacts. After at least 1250 impacts, the final volume is considered reached. The ratio of bulk density to tap density indicates how much a powder can be compacted, i.e., how strong the resistance is to forming a densest packing. This reveals something about how well the powder particles slide past each other or how much this relative movement is hindered—for example, by the particle shape.

[0093] In another embodiment, the lignin particles have a shear stress of 100 to 250 Pa. P93087WO August 11, 2025

[0094] Viering, Jentschura & Partner mbB

[0095] In one embodiment, the lignin particles have a contact friction angle of 30.0° to 35.0°, preferably of 30.5° to 32.5°.

[0096] In one embodiment, the lignin particles have a Carr index of 13.0 to 19.5. This gives the particles advantageous flow properties.

[0097] In another embodiment, the lignin particles have a flow index ff c from 5.0 to 18.0. This means the particles exhibit advantageous flow behavior.

[0098] In one embodiment, the lignin particles have a moisture content of less than 5 wt.% and preferably less than 3.5 wt.%.

[0099] In another embodiment, the lignin particles have a specific surface area (BET) of 0.5 to 100 m². 2 / g, preferably from 0.5 to 50 m 2 / g, especially preferably from 0.5 to 35 m 2 / g and especially preferably from 0.5 to 10 m 2 / g, determined according to DIN 66131 (with nitrogen).

[0100] In a preferred embodiment, the lignin contained in the agent for treating keratinous fibers is deodorized lignin. "Deodorized lignin" is understood to mean lignin whose content of odor-causing compounds has been significantly reduced. For this purpose, the lignin is subjected to a deodorization process.

[0101] The term "deodorization" refers to a reduction in the proportion of odor-causing compounds. Odor-causing compounds are generally volatile organic compounds (VOCs), which can be perceived by smell or detected through measurements in the gas phase. Specifically, VOCs are understood here to be volatile organic compounds that exhibit a high vapor pressure even at ambient temperature and can therefore readily diffuse from the substrate into the atmosphere. In the following, VOCs are understood to be organic components with a boiling point of 50–260 °C. Examples of VOCs are guaiacol and reduced organic sulfur compounds such as dimethyl disulfide and dimethyl trisulfide.The term "lignin deodorization" therefore refers to the reduction of the proportion of odor-causing volatile organic compounds (VOCs) or residues thereof derived from lignin. Deodorization leads to a reduction in the mass-based proportion of volatile organic compounds (VOCs) in the lignin substrate by at least 50%, preferably at least 60%, 70%, 80% or at least 90%, particularly P93087WO 11 August 2025.

[0102] Viering, Jentschura & Partner mbB preferably by at least 95%, 96%, 97%, 98% or 99%. Methods for determining the proportion of volatile organic compounds (VOCs) in a lignin-containing substrate are familiar to those skilled in the art.

[0103] In a preferred embodiment, the lignin contained in the agent for treating keratinous fibers has been enzymatically pretreated with cellulase, so that the content of cellulose and C5 / C6 monosaccharides has been greatly reduced.

[0104] Enzymes and enzymatic treatment methods for cellulase treatment are familiar to experts. One example is the cellulase Cellic® CTec2 from Novonesis A / S (Denmark), which has an optimum reaction temperature of pH 5 and a temperature of 45 to 50°C. Preferably, the lignin-containing substrate undergoes multiple, i.e., at least two, enzymatic treatments with cellulase during pretreatment.

[0105] The term "lignin-containing substrate" refers to a material or mixture of materials that contains lignin. Examples of lignin-containing substrates include wood, straw, bagasse, bran, grass, etc. The lignin-containing substrate can also be a pre-treated substrate, such as waste from the sulfate or kraft processes commonly used in papermaking, or waste from lignin-containing substrates treated with organic aqueous solvents (organosolv process). In connection with such waste, the terms "Kraft lignin," "organosolv" lignin, or hydrolysis lignin are also used. Lignocellulose-containing biomass also falls under the term "lignin-containing substrate." This refers to a material in which lignin is embedded in a framework formed from hemicelluloses and, primarily, cellulose.

[0106] In a preferred embodiment, the water-insoluble lignin is selected from the group consisting of natural lignin, Klason lignin, Kraft lignin, hydrolyzed lignin, ground wood lignin, soda lignin, organosolv lignin and aquasolv lignin, colloidal lignin and mixtures thereof.

[0107] Natural lignin is the lignin found in plant tissues and is also referred to as native lignin.

[0108] Klason lignin is the acid-insoluble lignin content of natural lignin. It is obtained by pre-hydrolysis of natural lignin in H₂SO₄, hydrolysis of the mixture at high temperatures. P93087WO 11 August 2025

[0109] Viering, Jentschura & Partner mbB

[0110] The retentate is obtained by temperature and filtration. It contains Klason lignin. The Klason process is known to those skilled in the art.

[0111] Hydrolyzed lignin is obtained by refluxing lignin or lignocellulose with HCl in a dioxane / water solution. This treatment leads to the degradation of lignin, forming significant amounts of arylpropanes, and the majority of the acidolysis monomers originate from the arylglycerol-β-aryl ether structure.

[0112] Ground wood lignin (MWL), also known as Björkman lignin, is obtained by grinding wood flour in a ball mill, either dry or in the presence of non-swelling solvents such as toluene, which destroys the cell structure of the wood. A portion of the lignin can be recovered from the suspension by extraction with a dioxane-water mixture. The Björkman process is known to those skilled in the art.

[0113] Kraft lignin is the lignin obtained through the Kraft process, also known as the Kraft pulp or sulfate process. This process converts wood into wood pulp, which consists of nearly pure cellulose fibers, the main component of paper, and is well-known to those skilled in the art. In the Kraft process, wood chips are treated with a hot mixture of water, sodium hydroxide (NaOH), and sodium sulfide (Na₂S), known as white liquor, which breaks the bonds between lignin, hemicellulose, and cellulose. The technology comprises several mechanical and chemical steps.

[0114] Soda lignin is produced using the soda process, in which fibrous wood material is heated in a pressure reactor at high temperature in the presence of sodium hydroxide, also known as cooking liquor. During this process, the lignin is separated from the cellulose and suspended in the liquid phase, known as black liquor. The black liquor therefore contains both lignin and sodium hydroxide and is referred to as soda lignin.

[0115] Organosolv lignin is obtained through the organosolv process. In this process, lignin is extracted from lignocellulosic biomass using organic solvents, typically in combination with an acidic catalyst. Organosolv lignin contains no sulfur or sulfonate groups and has a molecular weight of approximately 1000 to 2000 g / mol.

[0116] In a particularly preferred embodiment, the lignin is an aquasolv lignin. An aquasolv lignin is understood to be a lignin that is a P93087WO 11 August 2025

[0117] Viering, Jentschura & Partner mbB

[0118] The product was subjected to hot water extraction. A major advantage of this process is that it eliminates the need for aggressive solvents and chemical additives, which significantly simplifies its use in cosmetic applications.

[0119] Hot water extraction refers to a thermal treatment using water at a temperature above 100 °C and a pressure above the vapor pressure of water at that temperature. Examples include temperatures of 100–250 °C at pressures of 1–50 bar, for example, a temperature of 200 °C at a pressure of 30 bar. Where the terms "hot water hydrolysis" or "hot water pretreatment" are also used here, they are synonymous with the term "hot water extraction" as described above.

[0120] Colloidal lignin is obtained by processing wood residues into organosolv-extracted lignin and then converting this into an aqueous dispersion of colloidal lignin particles with a particle size of approximately 100–500 nm through filtration and precipitation steps. A corresponding process is disclosed in WO 2020 / 000008 A1.

[0121] In a particularly preferred embodiment, the following four types of lignin particles can be used as the lignin component of the agent according to the invention for the treatment of keratinous fibers:

[0122] 1. Lignin particles produced from birch (Betula pendula) using the Aquasolv process and cellulase treatment, followed by spray drying, and exhibiting the following properties: a. Consisting of 75-95 wt% lignin, 5-25 wt% hemicellulose / cellulose; b. Total sugar content of xylose, glucose, mannose, galactose, arabinose of less than 10 wt%; c. Mean particle size D50 between 10 and 15 pm and D90 less than 25 pm; d. pH value between 5 and 7; e. Viscosity (10% in water) less than 100 mPas; f. Low polarity,

[0123] Such lignin particles are available, for example, as LignoBase Cool BE25 from the company Lignopure (Hamburg, Germany). P93087WO August 11, 2025

[0124] Viering, Jentschura & Partner mbB

[0125] 2. Lignin particles produced from Scots pine (Pinus sylvestris) and spruce (Piceas abies) using the Aquasolv process and cellulase treatment, followed by spray drying, and exhibiting the following properties: a. Consisting of 75-95 wt% lignin, 5-25 wt% hemicellulose / cellulose; b. Total sugar content of xylose, glucose, mannose, galactose, and arabinose of less than 10 wt%; c. Mean particle size D50 between 10 and 15 pm and D90 less than 25 pm; d. pH value between 4.5 and 6.5; e. Viscosity (10% in water) less than 100 mPas; f. Medium polarity.

[0126] Such lignin particles are available, for example, as LignoBase Neutral PS25 from the company Lignopure (Hamburg, Germany).

[0127] 3. Lignin particles produced by alkaline pulping (soda pulping) of wheat straw (Triticum aestivum L.) and bamboo grass (Saccharum bengalense) followed by spray drying, exhibiting the following properties: a. Sulfate-free lignin consisting of 75-95 wt% lignin, 5-25 wt% hemicellulose / cellulose; b. Total sugar content of xylose, glucose, mannose, galactose, arabinose of less than 10 wt%; c. Mean particle size D50 between 10 and 15 pm and D90 less than 25 pm; d. pH value between 3.0 and 5.0; e. Viscosity (10% in water) less than 100 mPas; f. High polarity.

[0128] Lignin particles of this type are available, for example, as LignoBase Warm WS25 from the company Lignopure (Hamburg, Germany).

[0129] 4. Dispersion of colloidal lignin particles produced from birch (Betula pendula) by organosolv extraction with subsequent filtration and precipitation steps, and with the following properties: a. Sulfate-free lignin; b. Mean particle size D50 between 100 and 500 nm; c. Polydispersity index of less than 0.5; d. pH value between 3.0 and 6.0.

[0130] Such a dispersion is available, for example, as LignoGuard Aqua 20 from Lignovations GmbH (Klosterneuberg, Austria). P93087WO August 11, 2025

[0131] Viering, Jentschura & Partner mbB

[0132] Lignin particles of the aforementioned type 1 (e.g., LignoBase Cool BE25) are particularly preferred for temporary staining, as it has been shown that lignin particles with low polarity achieve the best staining of keratinous fibers. The other types of lignin particles mentioned also achieve good staining of keratinous fibers, either alone or in combination with type 1.

[0133] In the composition according to the invention for treating keratinous fibers, the lignin particles are contained in a weight fraction of 0.1 to 99.9 wt.%, preferably 2 to 80 wt.%, particularly preferably 5 to 70 wt.%, and especially preferably 10 to 65 wt.%, in each case based on the total weight of the ready-to-use composition. The lignin particles can, for example, be contained in a weight fraction of 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, or 70 wt.%.

[0134] It has been shown that in powdered and / or suspended ready-to-use keratin fiber treatment products, lignin concentrations between 10 and 65% are advantageous for adhesion and coloring, without making the hair feel too woody, as is the case with higher lignin concentrations, and without compromising the color result, especially when using additional pigments. When lignin is used in hair treatment products containing additional optional ingredients, 1 to 5% is sufficient for an SPF booster effect, but 2% and more lignin, if necessary in combination with colored pigments, provides sufficient coloring of the keratin fibers in very light hair. At significantly higher lignin concentrations, such as those found in ready-to-use keratin fiber treatment products in powder or pressed form, only very small amounts of the product are required, e.g.,less than 5% of the weight of the hair strand to achieve coloring.

[0135] If the lignin particles used according to the invention are present in a formulation such as a leave-in hair mask, which is optionally prepared by mixing the powdered ready-to-use color with a leave-in hair mask shortly before application by the hairdresser or user, the aforementioned low concentrations of 2% to 5% can already be used for coloring suitable light or bleached hair.

[0136] Hair coloring tests on light blonde strands (Kerling International Hair Factory, Backnang, color 11 / 0) have surprisingly shown that ready-to-use products for P93087WO 11 August 2025

[0137] Viering, Jentschura & Partner mbB

[0138] Treatment of keratinous fibers containing 2% of the lignin according to the invention can produce a nuance towards honey-blonde or ash-blonde shades.

[0139] In one embodiment, the at least one particle-shaped carrier material, which is solid under normal conditions, has a particle size of 5 nm to 100 pm, preferably of 0.1 to 60 pm and particularly preferably of 1 to 50 pm.

[0140] In a preferred embodiment of the invention, this carrier material is selected from optionally modified starches (e.g., from maize, rice, potatoes, tapioca, wheat, barley, amaranth) and starch derivatives, which are optionally pregelatinized, in particular starch derivatives of the type AGENAFLO® OS 9051 (aluminum starch octenylsuccinate), hydrophobically modified waxy maize starch of the type AGENAFLO® 9050 and hydrophobically modified tapioca starch AGENAFLO® TS, cellulose and cellulose derivatives, cyclodextrins, maltodextrins, lactose, silicon dioxide, amorphous silicas, in particular precipitated silicas, particularly preferably pyrogenic silicas, e.g.available under the trade name Aerosil®, spherical polyalkylsesquisiloxane particles (especially Aerosil® R972 and Aerosil® 200V from Evonik), silica gels, talc, kaolin, mica, nepheline, perlite, phlogopite, synthetic fluorophlogopite, clays, especially bentonites, aluminum oxide, magnesium aluminum silicates, magnesium stearate, boron nitride, lactoglobulin derivatives, e.g. sodium C8-16-isoalkylsuccinyl lactoglobulin sulfonate, available from Brooks Industries as the trade product Biopol® OE, glass powders, organic polymer powders, especially polyolefins, polycarbonates, polyurethanes, polylactides, polyhydroxybutyrates, polyamides, etc. B. Nylon, polyesters, polystyrenes, polyacrylates, (meth)acrylate or (meth)acrylate vinylidene copolymers, which may be cross-linked, or silicones, as well as mixtures of these substances.

[0141] Polymer powders based on a polymethacrylate copolymer, which can be used as carriers according to the invention, are available, for example, as the commercial product Polytrap® 6603 (Dow Corning). Polymer powders based on polyamides can also be used as carriers, such as those available from Elf Atochem under the name Orgasol® 1002 (polyamide-6) and Orgasol® 2002 (polyamide-12). Other carriers can be polymer powders such as cross-linked polymethacrylates and polymethyl methacrylates (from Sensient Beauty, in particular Covabead LH 85), etc. B. the products of the Micropearl® M, Micropearl® 305 and Micropearl® 310 series from SEPPIC, Covabead from Sensient Beauty or Plastic Powder A from NIKKOL), styrene-divinylbenzene copolymers (e.g. Plastic Powder FP from NIKKOL), polyethylene and polypropylene powders (e.g. P93087WO 11 August 2025

[0142] Viering, Jentschura & Partner mbB

[0143] ACCUREL® EP 400 from AKZO) or silicone polymers (e.g. Silicone Powder X2-1605 from Dow Corning).

[0144] Particularly preferred carrier materials are selected from water-insoluble fillers, in particular amorphous silicas, especially precipitated silicas, especially pyrogenic silicas, starch and starch derivatives, talc, kaolin, mica, nepheline, pearlite, phlogopite, synthetic fluorphlogopite, clays, especially bentonites, magnesium aluminum silicates, and organic polymer powders. Amorphous silicas, especially precipitated silicas, especially pyrogenic silicas, starch and starch derivatives, talc, kaolin, mica, nepheline, pearlite, phlogopite, synthetic fluorphlogopite, and clays, especially bentonites, are particularly preferred, with talc, starch, and modified starch being especially noteworthy due to their outstanding properties. It is important in this context that the carrier material used, in the case of talc, is absolutely asbestos-free and has the lowest possible proportion of particularly small particles.Due to asbestos concerns, talc has already been replaced with cornstarch in many body powders. Starches and their derivatives are particularly preferred for products labeled "talc-free" and for vegan natural cosmetics.

[0145] In one embodiment, the carrier material is present in a weight fraction of 0.1 to 99.9 wt.%, preferably 20 to 98 wt.%, particularly preferably 30 to 95 wt.%, and especially preferably 35 to 90 wt.%, in each case based on the total weight of the ready-to-use agent for treating keratinous fibers. The carrier material can, for example, be present in a weight fraction of 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, or 98 wt.%.

[0146] In a further embodiment, the agent for treating keratinous fibers additionally contains an active ingredient, excipient, or additive selected from the group consisting of absorbents, antimicrobial substances; antioxidants; antiperspirants, antifoaming agents; anti-dandruff agents; antistatic agents; binders; chelating agents, co-emulsifiers, deodorizing agents; emollients; emulsifiers, emulsion stabilizers; enzymes; humectants; film formers; preservatives; corrosion inhibitors; solvents; pH regulators; reducing agents; thickeners; surfactants; hair-conditioning compounds such as cetrimonium chloride, esterquats, alkylmethicone, and amodimethicone; fiber-improving agents; protein hydrolysates of animal and / or plant origin; and plant extracts. Consistency enhancers such as sugar esters, polyol esters P93087WO 11 August 2025

[0147] Viering, Jentschura & Partner mbB and polyolalkyl ethers; clay minerals, fats and oils modified with quaternary ammonium compounds; swelling and penetration agents; pearlescent agents such as ethylene glycol mono- and distearate as well as PEG-3 distearate; styling polymers; rheological additives; natural and / or synthetic waxes; cosmetic active ingredients such as panthenol, pantolactone and niacinamide; bactericides; fungicides; germicides; odor complexing substances; water repellents; fragrances; and UV protection substances, and combinations thereof.

[0148] The selection of these additional substances will be made by a person skilled in the art according to the desired properties of the agents for treating keratinous fibers. Regarding further optional components and the quantities of these components used, explicit reference is made to the relevant handbooks known to those skilled in the art. The additional active ingredients, excipients, and additives are preferably used in the agents for treating keratinous fibers according to the invention in quantities of 0.0001 to 25 wt.%, and in particular 0.0005 to 15 wt.%, based on the total weight of the respective agents.

[0149] Further preferred compositions for the treatment of keratinous fibers according to the invention are characterized in that they contain at least one anti-dandruff agent. Particularly preferred anti-dandruff agents are selected from piroctone olamine, zinc pyrithione, ketoconazole, ciclopirox, selenium disulfide, propanediol caprylate, and climbazole. According to the invention, particularly preferred benefit compositions are characterized in that they contain at least one anti-dandruff agent in a total amount of 0.01–5 wt.%, preferably 0.1–2 wt.%, and particularly preferably 0.4–1 wt.% based on the benefit composition.

[0150] Preferred ingredients of the compositions according to the invention for treating keratin fibers, in particular cosmetic compositions for treating keratin fibers, can be defined by their function. Naturally, some ingredients may also be multifunctional. Preferred ingredients of the compositions according to the invention for treating keratin fibers, preferably cosmetic products, may be: a) Absorbents and adsorbents: These preferably have the function of absorbing water- and / or oil-soluble dissolved or finely dispersed substances; P93087WO 11 August 2025

[0151] Viering, Jentschura & Partner mbB b) Antimicrobial substances: These can be added to products to generally reduce the activity of microorganisms, e.g., on the scalp and hair; c) Antioxidants: These are intended to prevent oxygen-induced reactions such as oxidation and thus extend the shelf life of the products, i.e., maintain the quality of the products; d) Antiperspirants: These are preferably used in cosmetics and reduce perspiration; e) Antifoaming agents: These can be added, e.g., to eliminate foam during manufacturing or to reduce the tendency of finished products to produce excessive foam; f) Anti-dandruff agents: These are primarily used in hair care products, as they can counteract dandruff formation; g) Antistatic agents: These are, for example, detangling agents in hair care products.They generally reduce the electrostatic charge of objects, such as the surface of hair. This makes hair significantly easier to comb; h) Binders: These ensure, for example, the cohesion of powder- and powder-containing products, such as cosmetic preparations; i) Chelating agents: These are added to cosmetic products, for example, so that they form complexes with metal ions in order to manipulate the stability and / or appearance of the products; j) Deodorants / antiperspirants: These can help prevent or reduce the development of unpleasant body odors. They can mask such odors and, if necessary, reduce perspiration; k) Emollients: In cosmetics, for example, these have the function of making the skin supple and smooth.Emollients according to the present invention are advantageously natural vegetable oils and / or synthetic triglycerides, substances from the group of esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids of a chain length of 3 to 30 C atoms and saturated and / or unsaturated, branched and / or unbranched alcohols of a P93087WO 11 August 2025.

[0152] Viering, Jentschura & Partner mbB

[0153] Chain lengths of 3 to 30 carbon atoms, as well as from the group of esters of aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 3 to 30 carbon atoms. Such ester oils can then advantageously be selected from the group of isopropyl palmitate, isopropyl stearate, n-butyl stearate, n-hexyl laurate, isooctyl stearate, isononyl stearate, isononyl isononanoate, 2-ethylhexyl palmitate, 2-hexyldecyl stearate, 2-octyldodecyl palmitate, erucylerucate, as well as synthetic, semi-synthetic, and natural mixtures of such esters, such as jojoba oil. Examples of commonly used emollients, which usually also act as occlusives and / or humectants, are natural vegetable oils, synthetic triglycerides, lanolin, mineral oil and other hydrocarbons, petrolatum, fats, shea butter, cocoa butter, waxes, fatty acid esters such as cetearyl isononanoate, decyl cocoate, oleylerucate, 2-ethylhexyl stearate, isocetyl stearate.further dioctyl ethers and dicaprylyl carbonate; l) Emulsion stabilizers: These can further support the emulsification process (see emulsifiers and co-emulsifiers) and thus further improve the stability and shelf life of the product. Examples include aluminum stearate, magnesium stearate, cetyl alcohol, cetearyl alcohol, behenyl alcohol, and glyceryl stearate; m) Humectants: These can contribute to maintaining or restoring skin moisture and counteract skin dehydration; n) Film formers: These are able to create a protective, stabilizing film on surfaces, such as hair or nails, for example, in cosmetic products; o) Preservatives: These are added to cosmetic products, for example, to protect them from the harmful effects of microorganisms (bacteria, fungi, yeasts) and thus prevent spoilage; p) Corrosion inhibitors: These can, for example,to prevent corrosion of parts treated with the inventive agent for treating keratinous fibers; q) solvents (anhydrous): They can, for example, form the basis for liquid cosmetic preparations, but also be a component of solid products; P93087WO 11 August 2025.

[0154] Viering, Jentschura & Partner mbB r) pH regulators / buffer substances: These can be used, for example, in cosmetics to adjust or stabilize a desired pH value; s) swelling and penetration agents: These are able to cause swelling of the skin or hair or improved penetration of active ingredients; t) reducing agents: These are able to change the chemical properties of another substance through redox processes; u) rheological additives: These are able to change the flow behavior and viscosity of cosmetics; v) styling polymers: They can be used to shape and hold hairstyles; w) surfactants: They can be used to cleanse skin and hair; x) emulsifiers: These make it possible to combine immiscible liquid components, such as oil and water, into a stable mixture (emulsion). Examples of emulsifiers are CETEARETH-20, CETEARYL GLUCOSIDE, CETYL PEG / PPG-10 / 1 DIMETHICONE,GLYCERYL OLEAT, GLYCERYL OLEAT SE, GLYCERYL STEARAT, GLYCERYL STEARAT SE, GLYCOL STEARAT SE, LANOLIN, LECITHIN, PEG-120 METHYL GLUCOSE DIOLEAT, PEG-18 GLYCERYL OLEAT / COCOAT, PEG-20 GLYCERYL STEARAT, PEG-40 gehärtetes Rizinusöl, PEG-40 STEARAT, PEG-7 GLYCERYL COCOAT, PEG-7 gehärtetes Rizinusöl, POLYGLYCERYL-3 DIISOSTEARAT, POLYGLYCERYL-3 METHYLGLUCOSE DISTEARAT, POLYGLYCERYL-3 POLYRICINOLEAT, POLYGLYCERYL-4 CAPRYLAT, POLYSORBAT 20, POTASSIUM CETYL PHOSPHAT, Kalium STEARAT, Natrium C12-13 PARETH SULFAT, Natriumstearat, SORBITAN LAURAT, SORBITAN OLEAT, SORBITAN STEARAT, STEARETH-2, STEARETH-21 , Stearinsäure, Saccharose LAURAT, Saccharose MYRISTAT, Saccharose RICINOLEAT, TRICETEARETH-4 PHOSPHAT, Sorbitan Laurat, Polyglyceryl-4 Laurat, Dilauryl Citrat, Glyceryl Citrat / Lactat / Linoleat / Oleat, Polyglyceryl-4 Cocoat Polyglyceryl-3 Caprat (und) Glyceryl Caprylat, Glyceryl Citrat / Lactat / Linoleat / Oleat, Glyceryl Oleate Citrat, Natrium Cocoyl Glutamat,Lauryl Glucoside (and) Polyglyceryl-2 Dipolyhydroxystearate (and) Glycerin, Polyglyceryl-6 Stearate (and) Polyglyceryl-6 Behenate, Polyglyceryl-2 Dipolyhydroxystearate, Polyglyceryl-4 Diisostearate / Polyhydroxystearate / Sebacate, Polyglyceryl-6 Polyhydroxystearate (and) Polyglycyceryl-6 Polyricinoleate, Polyglyceryl-4 diisostearate / polyhydroxystearate / sebacate; polyglyceryl-3 oleate; Diisostearoyl Polyglyceryl-3 Dimer Dilinoleate. P93087WO August 11, 2025,

[0155] Viering, Jentschura & Partner mbB

[0156] The composition according to the invention for treating keratinous fibers may preferably contain one or more antimicrobial agents or preservatives and / or multifunctional agents. Preservatives are those preservative substances that are authorized for use in cosmetic products in accordance with the German Cosmetics Regulation and Regulation (EC) No. 1223 / 2009 on cosmetic products for use in cosmetic products in Europe.

[0157] If the composition according to the invention for treating keratinous fibers contains at least one preservative or antimicrobial or multifunctional agent, then the at least one preservative or antimicrobial or multifunctional agent is present in the composition according to the invention with a total content of 0.0001 to 8.0 wt.%, preferably 0.0005 to 4.0 wt.%, particularly preferably 0.001 to 2.0 wt.%, and most preferably 0.1 to 1 wt.%, in the composition according to the invention for treating keratinous fibers, based on the total composition of the composition.

[0158] Antimicrobial agents or preservatives are classified according to their antimicrobial spectrum and mechanism of action as bacteriostatics and bactericides, fungistatics and fungicides, etc. Within the scope of the invention, the terms antimicrobial effect and antimicrobial agent have their customary meanings. Suitable antimicrobial agents are preferably selected from the groups of alcohols, aldehydes, antimicrobial acids or their salts, antimicrobial aromatics, carboxylic acid esters, acid amides, aliphatic diols, phenols, phenol derivatives, diphenyls, diphenylalkanes, urea derivatives, oxygen and nitrogen acetals and formals, benzamidines, isothiazolines, quaternary ammonium compounds, antimicrobial surfactants, and any mixtures of the aforementioned substances.

[0159] The antimicrobial active ingredient is preferably selected from 1,3-propanediol, methylpropanediol, 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol, ethylhexylglycerin, hexoxypropane-1,2-diol, heptoxypropane-1,2-diol, octoxypropane-1,2-diol, 3-benzyloxypropane-1,2-diol, 3-phenylethoxypropane-1,2-diol, 3-phenylpropyloxypropane-1,2-diol, 3-methylbenzyloxypropane-1,2-diol, 3-phenylpropanol, 1,2-decanediol, glyceryl caprylate, hydroxyacetophenone, triethyl citrate, tropolone, o-cymen-5-ol. Undecylenic acid, caprylhydroxamic acid, propionic acid, dehydroacetic acid (3-acetyl-6-methyl-2H-pyran-2,4(3H)-dione), anisic acid, anisate, levulinic acid, levulinate, o-phenylphenol. The following may be used as preservatives, which are particularly advantageous: 2- P93087WO 11 August 2025

[0160] Viering, Jentschura & Partner mbB

[0161] Phenoxyethanol, methylparaben, ethylparaben, propylparaben, butylparaben, benzyl alcohol, sorbic acid and / or salts of sorbic acid, for example potassium sorbate, benzoic acid and / or salts of benzoic acid, for example sodium benzoate, salicylic acid and / or salts of salicylic acid, for example sodium salicylate, and the corresponding salts of preservatives, as well as any mixtures thereof, may be used. Furthermore, natural antimicrobial agents of plant origin (e.g., from spices or herbs), animal origin, and microbial origin are suitable.Preferably, antimicrobial surfactant quaternary compounds, a natural antimicrobial agent of plant origin and / or a natural antimicrobial agent of animal origin, most preferably at least one natural antimicrobial agent of plant origin from the group comprising caffeine, theobromine, and theophylline, as well as thymol, and / or at least one natural antimicrobial agent of animal origin from the group comprising enzymes such as milk protein, lysozyme, and lactoperoxidase, and / or at least one antimicrobial surfactant quaternary compound with an ammonium, sulfonium, or phosphonium residue, may be used. Substances of microbial origin, so-called bacteriocins, may also be used. Glycine, glycine derivatives, formic acid, and peroxides are particularly preferred.

[0162] According to a further preferred embodiment, the composition for treating keratinous fibers according to the invention can contain at least one fragrance. The fragrance can be contained within the composition for treating keratinous fibers, or it can be applied directly to the hair as a substrate. Particularly preferred according to the invention are fragrances containing:

[0163] (a) almond-like odor, such preferably as benzaldehyde, pentanal, heptenal, 5-methylfurfural, methylbutanal, furfural and / or acetophenone or

[0164] (b) apple-like odor, such preferably (S)-(+)-ethyl 2-methylbutanoate, diethyl malonate, ethyl butyrate, geranyl butyrate, geranyl isopentanoate, isobutyl acetate, linalyl isopentanoate, (E)-β-damascone, heptyl 2-methylbutyrate, methyl 3-methylbutanoate, 2-hexenal pentyl methylbutyrate, ethyl methyl butyrate and / or methyl 2-methylbutanoate or

[0165] (c) apple peel odor, such preferably ethyl hexanoate, hexyl butanoate and / or hexyl hexanoate or

[0166] (d) apricot-like odor such as preferably y-undecalactone or P93087WO 11 August 2025

[0167] Viering, Jentschura & Partner mbB

[0168] (e) banana-like odor, such preferably isobutyl acetate, isoamyl acetate, hexenyl acetate and / or pentyl butanoate or

[0169] (f) bitter almond-like odor such as preferably 4-acetyltoluene or

[0170] (g) blackcurrant-like odor such as preferably mercaptomethylpentanone and / or methoxymethylbutanethiol or

[0171] (h) citrus-like odor such as preferably linalyl pentanoate, heptanal, linalyl isopentanoate, dodecanal, linalyl formate, ap-dimethylstyrene, p-cymenol, nonanal, β-cubeben, (Z)-limonene oxide, cis-6-ethenyltetrahydro-2,2,6-trimethylpyran-3-ol, cis-pyranoid linalool oxide, dihydrolinalool, 6(10)-dihydromyrcenol, dihydromyrcenol, β-famesene, (Z)-β-farnesene, (Z)-ocimene, (E)-limonene oxide, dihydroterpinyl acetate, (+)-limonene, (epoxymethylbutyl)-methylfuran and / or p-cymene or

[0172] (i) cocoa-like odor such as preferably dimethylpyrazine, butyl methyl butyrate and / or methylbutanal or

[0173] (j) coconut-like odor, such as preferably γ-octalactone, γ-nonalactone, methyl laurate,

[0174] Tetradecanol, methyl nonanoate, (3S,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one, 5-butyl-dihydro-4-methyl-2(3H)-furanone, ethyl undecanoate and / or δ-decalactone or

[0175] (k) creamy odor such as preferably diethyl acetal, 3-hydroxy-2-butanone, 2,3-pentadione and / or 4-heptenal or

[0176] (l) flower-like odor such as preferably benzyl alcohol, phenylacetic acid, tridecanal, p-anisyl alcohol, hexanol, (E,E)-farnesylacetone, methyl geranate, trans-crotonaldehyde, tetradecyl aldehyde, methyl anthranilate, linalool oxide, epoxylinalool, phytol, 10-epi-y-eudesmol, nerol oxide, Ethyl dihydrocinnamate, y-dodecalactone, hexadecanol, 4-mercapto-4-methyl-2-pentanol, (Z)-ocimene, cetyl alcohol, nerolidol, ethyl (E)-cinnamate, elemicin, pinocarveol, a-bisabolol, (2R,4R)-Tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran, (E)-isoelemicin, Methyl 2-methylpropanoate, trimethylphenylbutenone, 2-methylanisole, ß-farnesol, (E)-isoeugenol, nitrophenylethane, ethyl vanillate, 6-methoxyeugenol, linalool, ß-lonone, trimethylphenylbutenone, ethyl benzoate, phenylethyl benzoate; Isoeugenol and / or acetophenone or

[0177] (m) Fresh odor preferably such as methyl hexanoate, undecanone, (Z)-limonene oxide, benzyl acetate, ethyl hydroxyhexanoate, isopropyl hexanoate, pentadecanal, β-elemene, α- P93087WO 11 August 2025

[0178] Viering, Jentschura & Partner mbB

[0179] Zingiberene, (E)-limonene oxide, (E)-p-mentha-2,8-dien-1-ol, menthone, piperitone, (E)-3-hexenol and / or carveol or

[0180] (n) Fruity odor similar to ethylphenyl acetate, geranyl valerate, γ-heptalactone,

[0181] Ethyl propionate, diethyl acetal, geranyl butyrate, ethyl heptylate, ethyl octanoate,

[0182] Methylhexanoate, Dimethylheptenal, Pentanone, Ethyl 3-methylbutanoate, Geranylisovalerate, lobutylacetate, Ethoxypropanol, Methyl-2-butenal, Methylnonanedione, Linalylacetate,

[0183] Methyl geranate, limonene oxide, hydrocinnamon alcohol, diethyl succinate, ethyl hexanoate,

[0184] Ehylmethylpyrazine, neryletate, citronellyl butyrate, hexyl acetate, nonyl acetate, butyl methylbutyrate, pentenal, isopentyldimethylpyrazine, p-menth-1-en-9-ol, hexadecanone, octyl acetate, y-dodecalactone, epoxy-ß-ionone, ethyl octenoate, ethyl isohexanoate, isobornyl propionate, Cedrenol, p-menth-1-en-9-yl acetate, cadinadiene, (Z)-3-hexenylhexanoate, ethyl cyclohexanoate, 4-methylthio-2-butanone, 3,5-octadienone, methylcyclohexanecarboxylate, 2-pentylthiophene, a-ocimene, butanediol, ethyl valerate, pentanol, isopiperitone, butyl octanoate, ethyl vanillate, methyl butanoate, 2-Methylbutyl acetate, propylhexanoate, butylhexanoate, isopropyl butanoate, spathulenol, butanol, o-dodecalactone, methylquinoxaline, sesquiphellandrene, 2-hexenol, ethyl benzoates, isopropyl benzoate, ethyl lactate and / or citronellyl isobutyrate or

[0185] (o) geranium-like odor, such preferably geraniol, (E,Z)-2,4-nonadienal, octadienone and / or o-xylene or

[0186] (p) grape-like odor such as preferably ethyl decanoate and / or hexanone or

[0187] (q) grapefruit-like odor such as preferably (+)-5,6-Dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one and / or p-menthenthiol or

[0188] (r) grassy odor such as preferably 2-ethylpyridine, 2,6-dimethylnaphthalene, hexanal and / or (Z)-3-hexenol or

[0189] (s) green note, preferably 2-ethylhexanol, 6-decenal, dimethylheptenal, hexanol, heptanol, methyl-2-butenal, hexyloctanoate, nonanoic acid, undecanone, methyl geranate, isobornyl formate, butanal, octanal, nonanal, epoxy-2-decenal, cis-linalool, Pyranoxide, nonanol, y-dimethylallyl alcohol, (Z)-2-penten-1-ol, (Z)-3-hexenyl butanoate, isobutylthiazole, (E)-2-nonenal, 2-dodecenal, (Z)-4-decenal, 2-octenal, 2-hepten-1-al, bicyclogermacrene, 2-octenal, a-thujene, (Z)-ß-farnesene, (-)-y-elemene, 2,4-Octadienal, fucoserrate, hexenyl acetate, geranylacetone, valencene, ß-eudesmol, 1-hexenol, (E)-2-undecenal, artemisiaketone, viridiflorol, 2,6-nonadienal, trimethylphenylbutenone, 2,4-nonadienal, P93087WO August 11, 2025

[0190] Viering, Jentschura & Partner mbB

[0191] Butyl isothiocyanate, 2-pentanol, elemol, 2-hexenal, 3-hexenal, (+)-(£)-limonene oxide, cis-isocitral, dimethyloctadienal, bornyl formate, bornyl isovalerate, isobutyraldehyde, 2,4-hexadienal, trimethylphenylbutenone, nonanone, (E)-2-hexenal, (+)-cis-rose oxide, menthone, coumarin, (epoxymethylbutyl)-methylfuran, 2-hexenol, (E)-2-hexenol and / or carvyl acetate or

[0192] (t) Green tea-like odor, preferably (-)-Cubenol or

[0193] (u) herbal odor, preferably octanone, hexyl octanoate, caryophyllene oxide, methylbutenol, safranal, benzyl benzoate, bornyl butyrate, hexyl acetate, β-bisabolol, piperitol, β-selinene, α-cubeben, p-menth-l-en-9-ol, 1,5,9,9-tetramethyl-12-oxabicyclododeca-4,7-diene, T-muurolol, (-)-cubenol, levomenol, ocimene, α-thujene, p-menth-1-en-9-yl acetate, dehydrocarveol, artemisia alcohol, γ-muurolene, hydroxypentanone, (Z)-ocimene, β-elemene, β-cadinol, (E)-β-ocimene, (Z)-dihydrocarvone, α-cadinol, Calamene, (Z)-Piperitol, Lavandulol, β-Bourbonene, (Z)-3-Hexenyl-2-methylbutanoate, 4-(1-Methylethyl)-benzenemethanol, Artemisia ketone, Methyl-2-butenol, Heptanol, (E)-Dihydrocarvone, p-2-Menthen-1-ol, α-Curcumene, Spathulenol, Sesquiphellandrene, Citronellyl valerate, Bornyl isovalerate, 1,5-Octadien-3-ol, Methyl benzoate, 2,3,4,5-Tetrahydroanisole and / or Hydroxycalamene or

[0194] (v) honey-like odor, preferably ethyl cinnamate, β-phenethyl acetate, phenylacetic acid, phenylethanal, methyl anthranilate, cinnamic acid, β-damascenone, ethyl (E) cinnamate, 2-phenylethyl alcohol, citronellyl valerate, phenylethyl benzoate and / or eugenol or

[0195] (w) hyacinth-like odor, preferably hotrienol or

[0196] (x) jasmine-like odor, preferably methyl jasmonate, methyl dihydroepijasmonate and / or methylepijasmonate or

[0197] (y) lavender-like odor, preferably linalyl valerate and / or linalool or

[0198] (z) lemon-like odor, preferably neral, octanal, o-3-carene, limonene, geranial, 4-mercapto-4-methyl-2-pentanol, citral, 2,3-dehydro-1,8-cineol and / or α-terpinene or

[0199] (aa) lily-like odor, preferably dodecanal or

[0200] (bb) magnolia-like odor, preferably geranylacetone or P93087WO 11 August 2025

[0201] Viering, Jentschura & Partner mbB

[0202] (cc) tangerine-like odor, preferably undecanol or

[0203] (dd) melon-like odor, preferably dimethylheptenal or

[0204] (ee) Mint-like odor, preferably menthone, ethyl salicylate, p-anisaldehyde, 2,4,5,7a-tetrahydro-3,6-dimethylbenzofuran, epoxy-p-menthene, geranial, (methylbutenyl)-methylfuran, dihydrocarvyl acetate, β-cyclocitral, 1,8-cineole, β-phellandrene, methylpentanone, (+)-limonene, dihydrocarveol, (-)-carvone, (E)-p-mentha-2,8-dien-1-ol, isopulegyl acetate, piperitone, 2,3-dehydro-1,8-cineole, α-terpineol, DL-carvone and / or α-phellandrene or

[0205] (ff) nutty odor, preferably 5-methyl-(E)-2-hepten-4-one, γ-heptalactone, 2-acetylpyrrole, 3-octen-2-one, dihydromethylcyclopentapyrazine, acetylthiazole, 2-octenal, 2,4-heptadienal, 3-octenone, hydroxypentanone, octanol, dimethylpyrazine, methylquinoxaline and / or acetylpyrroline or

[0206] (gg) orange-like odor, preferably methyl octanoate, undecanone, decyl alcohol, limonene and / or 2-decenal or

[0207] (hh) orange peel-like odor, preferably decanal and / or β-carene or

[0208] (ii) peach-like odor, preferably γ-nonalactone, (Z)-6-dodecene-γ-lactone, β-decalactone, R-β-decenolactone, hexylhexanoate, 5-octanolide, γ-decalactone and / or β-undecalactone or

[0209] (jj) peppermint-like odor, preferably methyl salicylate and / or 1-menthol or

[0210] (kk) pine-like odor, preferably ap-dimethylstyrene, β-pinene, bornyl benzoate, β-terpinene, dihydroterpinyl acetate and / or α-pinene or

[0211] (II) pineapple-like odor, preferably propyl butyrate, propyl propanoate and / or ethyl acetate or

[0212] (mm) plum-like odor, preferably benzyl butanoate, or

[0213] (nn) raspberry-like odor, preferably β-ionone or

[0214] (oo) rose-like odor, preferably β-phenethyl acetate, 2-ethylhexanol, geranyl valerate, geranyl acetate, citronellol, geraniol, geranyl butyrate, geranyl isovalerate, citronellyl butyrate, citronellyl acetate, isogeraniol, tetrahydro-4-methyl-2-(2-methyl-1- P93087WO 11 August 2025

[0215] Viering, Jentschura & Partner mbB propenyl)-2,5-cis-2H-pyran, isogeraniol, 2-phenylethyl alcohol, citronellyl valerate and / or citronellyl isobutyrate, or

[0216] (pp) Green mint-like odor, preferably carvyl acetate and / or carveol, or

[0217] (qq) strawberry-like odor, preferably hexyl methyl butyrate, methyl cinnamate, Pentenal, methyl cinnamate or

[0218] (rr) sweetish odor, preferably benzyl alcohol, ethyl phenyl acetate, tridecanal, nerol, methyl hexanoate, linalyl isovalerate, undecanaldehyde, caryophyllene oxide, linalyl acetate, safranal, uncineol, phenylethanal, p-anisaldehyde, eudesmol, ethyl methylpyrazine, citronellyl butyrate, 4-methyl-3-penten-2-one, nonyl acetate, 10-epi-y-eudesmol, β-bisabolol, (Z)-6-dodecen-γ-lactone, β-famesene, 2-dodecenal, γ-dodecalactone, epoxy-β-ionone, 2-undecenal, styrene glycol, methylfuraneol, (-)-cis-rose oxide, (E)-β-ocimene, dimethyl methoxyfuranone, 1,8-cineole, Ethylbenzaldehyde, 2-pentylthiophene, o-farnesene, methionol, 7-methoxycoumarin, (Z)-3-hexenyl-2-methylbutanoate, o-aminoacetophenone, viridiflorol, isopiperitone, ß-sinensal, ethyl vanillate, methyl butanoate, p-methoxystyrene, 6-methoxyeugenol, 4-hexanolide, δ-dodecalactone, sesquiphellandrene, diethyl malate, linalyl butyrate, guaiacol, coumarin, methyl benzoate, isopropyl benzoate, safrole, durene, γ-butyrolactone, ethyl isobutyrate and / or furfural or

[0219] (ss) Vanilla-like odor, preferably vanillin, methyl vanillate, acetovanilla and / or ethyl vanillate or

[0220] (tt) watermelon-like odor, preferably 2,4-nonadienal or

[0221] (uu) wood-like odor, preferably a-muurolene, cadina-1,4-dien-3-ol, isocaryophyllene, eudesmol, a-lonone, bornyl butyrate, (E)-a-bergamotene, linalool oxide, ethylpyrazine, 10-epi-y-eudesmol, germacrene B, trans-sabinene hydrate, dihydrolinalool, Isodihydrocarveol, ß-farnesene, ß-sesquiphellandrene, ö-elemene, a-calacoren, epoxy-ß-ionone, germacrene D, bicyclogermacrene, alloaromadendrene, a-thujene, oxo-ß-lonone, (-)-y-elemene, y-muurolene, sabinene, a-guaiene, a-copaene, y-cadinene, nerolidol, ß-eudesmol, a-cadinol, δ-cadinene, 4,5-dimethoxy-6-(2-propenyl)-1,3-benzodioxole, [1ar-(1aalpha,4aalpha,7alpha,

[0222] 7abeta,7balpha)]-Decahydro-1 , 1 ,7-trimethyl-4-methylene-1 H-cycloprop[e]azulene, α-Gurjunene, Guaiol, α-Farnesene, γ-Selinene, 4-(1-Methylethyl)-benzenemethanol, Perillene, Elemol, α-Humulene, β-Caryophyllene and / or β-Guaiene or

[0223] (vv) cotton-like odor (Cotton touch (Symrise) or Coton (Cosnaderm) or P93087WO 11 August 2025

[0224] Viering, Jentschura & Partner mbB

[0225] (ww) smell of coffee, espresso or cappuccino or

[0226] (xx) Mixtures of the above.

[0227] In a further preferred embodiment of the invention, the odorants are contained in derivatized form, from which they are released in a time-delayed manner upon application with water. Particularly preferred odorant derivatives for this purpose are silicon compounds, as disclosed in US 3215719, GB 2041964 A and GB 2319527 A, and especially silicic acid esters, as disclosed in US 20040072704 A1, DE 10 2004 028 018 A1 and DE 102005059935 A1. However, other odorant derivatives that release odorant molecules through hydrolysis or other reaction mechanisms are also preferred according to the invention.

[0228] In a further preferred embodiment according to the invention, the odorants are contained in encapsulated form, from which they are released in a time-delayed manner when used with water and / or when the agent according to the invention is mechanically applied to treat keratinous fibers.

[0229] According to the invention, it may be particularly preferred to use at least one unencapsulated and non-derivatized fragrance ingredient in combination with at least one encapsulated and / or at least one derivatized fragrance ingredient. This enables a staggered release of different fragrance ingredients over time and an exceptional fragrance experience for the consumer.

[0230] In a preferred embodiment, the composition according to the invention for treating keratinous fibers contains certain minimum values ​​of perfume oil, namely at least 0.00001 wt.%, advantageously at least 0.0001 wt.%, considerably advantageously at least 0.001 wt.%, advantageously at least 0.01 wt.%, further advantageously at least 0.1 wt.%, even more advantageously at least 0.2 wt.%, very advantageously at least 0.3 wt.%, and particularly advantageously at least 0.4 wt.% of perfume oil, based on the Benefit composition.

[0231] In a particularly preferred embodiment, the composition according to the invention for treating keratinous fibers contains the perfume oil(s) in a carried or encapsulated form. Talc, starches, celluloses, maltodextrin, and cyclodextrins are particularly preferred as (powdered) carriers for perfume oils. According to a further preferred embodiment, the composition according to the invention for treating P93087WO 11 August 2025

[0232] Viering, Jentschura & Partner mbB states that the keratin fibers are free of perfume oil. This is particularly recommended for consumers prone to allergies.

[0233] Further preferred agents according to the invention for the treatment of keratinous fibers are characterized in that the agent for the treatment of keratinous fibers contains at least one antioxidant.

[0234] Preferred antioxidants are selected from the group consisting of imidazole and imidazole derivatives (e.g., urocanic acid), D,L-carnosine, D-camosine, L-carnosine and their derivatives (e.g., anserine), carotenoids, carotenes (e.g., α-carotene, β-carotene, lycopene) and their derivatives, lipoic acid and its derivatives (e.g., dihydrolipoic acid), aurothioglucose, propylthiouracil, and other thio compounds (e.g., thioglycerol, thiosorbitol, thioglycolic acid, thioredoxin, glutathione, cysteine, cystine, cystamine, and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl, lauryl, palmitoyl, oleyl, γ-linoleyl, Cholesteryl and glyceryl esters) and their salts, dilaurylthiodipropionate, distearylthiodipropionate, thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (e.g.Buthionine sulfoximines, homocysteine ​​sulfoximine, buthionine sulfones, penta-, hexa-, heptathionine sulfoximine) in very low tolerable doses (e.g., pmol / kg to pmol / kg), bile acids, bile extracts, gallic acid esters (e.g., propyl, octyl, and dodecyl gallate), 6,7-disubstituted 2,2-dialkyl chromans or chromenes, in particular 4-dihydro-7-methoxy-2,2-dimethyl-2H-1-benzopyran-6-ol, flavonoids, catechins, bilirubin, biliverdin, and their derivatives, folic acid and its derivatives, hydroquinone and its derivatives (7R arbutin), ubiquinone and ubiquinol, and their derivatives, vitamin C and its derivatives (e.g., ascorbyl palmitate, -stearate, -dipalmitate, -acetate, Mg-ascorbyl phosphate, sodium and magnesium ascorbate, disodium ascorbyl phosphate and -sulfate, potassium ascorbyl tocopheryl phosphate, chitosanascorbate), isoascorbic acid and its derivatives, tocopherols and their derivatives (e.g.Tocopheryl acetate, linoleate, oleate and succinate, tocophereth-5, tocophereth-10, tocophereth-12, tocophereth-18, tocophereth-50, tocophersolane), tocotrienols and their derivatives, in particular tocotrienol esters, vitamin A and derivatives, in particular esters, e.g., vitamin A palmitate, coniferyl benzoate of benzoin resin, rutin, rutinic acid and their derivatives, disodium rutinyl disulfate, kojic acid, chitosan glycolate and salicylate, butylhydroxytoluene, butylhydroxyanisole, nordihydroguaiac resinic acid, nordihydroguaiac acid and trihydroxybutyrophenone. P93087WO 11 August 2025.

[0235] Viering, Jentschura & Partner mbB

[0236] The total amount of the at least one antioxidant in the compositions according to the invention for the treatment of keratinous fibers is preferably 0.001 - 10 wt.%, particularly preferably 0.05 - 5 wt.% and extraordinarily preferably 0.1 - 2 wt.%, in each case based on the total weight of the ready-to-use composition for the treatment of keratinous fibers.

[0237] The agent according to the invention for the treatment of keratinous fibers can additionally contain a clay mineral modified with quaternary ammonium compounds.

[0238] The clay minerals modified with quaternary ammonium compounds are able to suspend and stabilize any color pigments also contained in an alcoholic carrier medium, effectively preventing the color pigments from clumping or conglomerating at the bottom of the application vessel even after long transport and storage periods.

[0239] Clay minerals, as defined in the invention, are minerals belonging to the group of phyllosilicates (layer silicates or sheet silicates) and band silicates. Clay minerals typically occur in the form of small, mostly plate-shaped crystals (0 <2 pm).

[0240] The clay minerals modified with quaternary ammonium compounds are either colorless or white and are used in the form of colorless or white powders or gels. These modified clay minerals are therefore not suitable for achieving a color effect on keratin materials, but rather serve as lipophilic thickening agents to suspend the actual color pigments. Consequently, the modified clay minerals in this group are explicitly not classified as color pigments.

[0241] The silicate structure of clay minerals is characterized by sequences of tetrahedral and octahedral layers. Clay minerals with a sequence of one tetrahedral layer followed by one octahedral layer are called two-layer clay minerals or 1:1 minerals. An example of a 1:1 clay mineral according to the invention is kaolinite. The average composition of kaolinite is given as Ah[(OH)₄ / Si₂O₅] or Al₂O₃ ■ 2 SiO₂ ■ 2 H₂O. Clay minerals with structures consisting of one octahedral layer and two tetrahedral layers are called three-layer minerals, or 2:1 minerals. Examples include illite, the smectites, glauconite, and vermiculite.

[0242] Illite is a mica-like three-layer clay mineral with the average composition Ko,7Mo,i + (AI,Fe 3+ )i,7(Mg,Fe 2+ ) 0 ' 3 [Si3,5Alo,50io(OH)2]. P93087WO August 11, 2025

[0243] Viering, Jentschura & Partner mbB

[0244] Smectites belong to the phyllosilicates and are three-layer clay minerals (2:1 layer silicates) in which a central layer of octahedrally coordinated cations is sandwiched between two layers of [(Si,Al)O4] tetrahedra. Numerous substitutions occur in the octahedral layer; it can contain, in addition to mostly predominant Al, ⁻¹⁰⁺⁻¹ ... 3+ (Montmorillonite), Mg 2+ (Saponite) or Fe 3+ (Nontronite) or cations such as Zn 2+ (Sauconit), Ni 2+ (Nickel-S.) and Li + (Hectorite) contained; in the tetrahedral layer, silicon can be partially replaced by Al 3+ (e.g., in the case of Beidellit) and also Fe 3+ (in the case of nontronite) are replaced. These substitutions result in an imbalance in the charge balance, which is compensated for by exchangeable cations, usually sodium, calcium, and potassium, and sometimes magnesium ions, between the layered packages.

[0245] Glauconite is an intensely green, monoclinic, hydrated potassium-iron-aluminum silicate belonging to the clay minerals, containing 2-15% K2O and a high Fe content. 3+ / Fe 2+ -Relationship.

[0246] Vermiculite is a clay mineral belonging to the three-layer (2:1) phyllosilicates; approximately (Mg,Al,Fe)3[ (Si,Al)40io(OH)2]Mg x (H2O) n , with 0.9 > x > 0.6. The silicon in the tetrahedral layers can be partially replaced by Al 3+ and Fe 3+ The magnesium in the octahedral layers can be partially replaced by Al 3+ , Fe 3+ , subordinate also Fe 2+, be replaced; furthermore, vermiculite can contain Ti, Ni, Cr, Zn, and Mn as trace elements. The negative charge x of the three-layer packages of 0.9 > x > 0.6 per formula unit is balanced by cations incorporated between the layer packages, which are readily exchangeable with each other and with Rb, Cs, Li, NH4, and organic compounds, primarily Mg, but also Ca, Na, and K. Oxidations of Fe 2+ to Fe 3+ The addition of protons to the octahedral sites leads to a reduction in the interlayer charge. The layer charge can also be reduced directly by the addition of protons to structural OH groups.

[0247] Sepiolite (known as meerschaum; chemical formula Mg4SieOi5(OH)2 x 6 H2O) is a clay mineral with a fibrous structure.

[0248] Palygorskite is a magnesium-rich, phyllosilicate, three-layer clay mineral with a fibrous structure. It contains more aluminum and less magnesium than the similar sepiolite. The fibrous structure in palygorskite (known as mountain leather; chemical formula (Mg,Al)₂Si₄O₆(OH)₄H₂O) is formed by papyrus-like or fibrous magnesium silicates, which are classified as phyllosilicates. However, they differ from other phyllosilicates by the absence of continuous octahedral layers. P93087WO August 11, 2025

[0249] Viering, Jentschura & Partner mbB

[0250] Montmorillonite, for which the molecular formula Ah[(OH)2 / Si4Oio] - n H2O or Al2O3 - 4 SiC>2 - H2O - n H2O is given, belongs to the clay minerals of the smectite group. Montmorillonite crystallizes in the monoclinic-pseudohexagonal form.

[0251] Saponite is a swelling, monoclinic clay mineral belonging to the smectites, in which the octahedral layers in the structure consist almost exclusively of Mg. 2+ -, Fe 2+ and Fe 3+ -ions are occupied. A negative charge of x < 0.6 per O (OH)2 in the tetrahedral layers is balanced by cations between the layer packs. By incorporating columns of polyoxo cations, e.g., Ali3 7+ {via polyhydroxo cations [Ali3O4(OH)24(H2O)i2] 7+} (so-called pillared columns) create interlamellar pores.

[0252] Hectorites belong to the smectites and have the approximate chemical formula M + 0.3(Mg2.7Lio.3) [Si4O (OH)2], wherein M + mostly Na + represents.

[0253] Bentonites are clays and rocks that contain smectites, especially montmorillonite, as their main minerals.

[0254] The “raw” bentonites are either calcium bentonites (referred to as Fuller earths in Great Britain) or sodium bentonites (also known as Wyoming bentonites).

[0255] In these clay minerals, the layered packages can be shifted relatively easily against each other, resulting in the plate-like structure typical of many clay minerals. Ions, water molecules, and other substances (such as quaternary ammonium compounds) can be incorporated between the layered packages, which can lead to a widening of the layer intervals (swelling).

[0256] Synthetically produced smectites are also suitable according to the invention.

[0257] Clay minerals that are particularly suitable for modification with quaternary ammonium compounds may be selected from montmorillonite, sepiolite, palygorskite, vermiculite, glauconite, hectorite, saponite, beidellite, nontronite, sauconite, bentonite and stevensite.

[0258] Particularly preferred clay minerals within the meaning of the present invention may be selected from montmorillonite and sepiolite.

[0259] In a further particularly preferred embodiment, a means according to the invention for treating keratinous fibers is characterized in that it contains at least one clay mineral modified with quaternary ammonium compounds, wherein the clay mineral is selected from the group consisting of montmorillonite, sepiolite, hectorite, P93087WO 11 August 2025

[0260] Viering, Jentschura & Partner mbB

[0261] Palygorskite, vermiculite, glauconite, saponite, beidellite, nontronite, sauconite, bentonite and stevensite, especially preferably selected from montmorillonite and sepiolite.

[0262] The clay minerals are each treated or modified with quaternary ammonium compounds.

[0263] Suitable quaternary ammonium compounds for treating clay minerals, as well as methods for treating clay minerals with such compounds, are known. Clay minerals modified with quaternary ammonium compounds are described in German patent application DE 102017222 725 A1, to which explicit reference is made.

[0264] Further preferred agents for the treatment of keratinous fibers according to the invention are characterized in that they contain at least one plant extract.

[0265] According to the invention, preferred plant extracts are usually produced by extraction from the whole plant, but in some cases also exclusively from flowers and / or leaves and / or seeds and / or other parts of the plant.Particularly preferred according to the invention are extracts from the meristem, i.e., the dividing meristematic tissue of plants, and from specific plants such as green tea, witch hazel, chamomile, calendula, pansy, peony, aloe vera, dittany, rockrose, horse chestnut, sage, willow bark, cinnamon tree, chrysanthemums, oak bark, nettle, hops, burdock root, horsetail, hawthorn, linden blossoms, almonds, spruce needles, sandalwood, juniper, coconut, kiwi, guava, lime, mango, apricot, wheat, melon, orange, grapefruit, avocado, rosemary, birch, beech shoots, mallow, meadowsweet, yarrow, wild thyme, thyme, lemon balm, restharrow, marshmallow (Althaea), mallow (Malva sylvestris), violet, blackcurrant leaves, and coltsfoot. Cinquefoil, ginseng, ginger root, and sweet potato. Algae extracts can also be used to advantage.The algal extracts used according to the invention are derived from green algae, brown algae, red algae, or blue-green algae (cyanobacteria). The algae used for extraction can be of natural origin or obtained through biotechnological processes and, if desired, modified from their natural form. The modification of the organisms can be achieved through genetic engineering, breeding, or cultivation in media enriched with selected nutrients. Preferred algal extracts are derived from kelp, blue-green algae, the green alga Codium tomentosum, and the brown alga Fucus vesiculosus. A particularly preferred algal extract is derived from P93087WO 11 August 2025.

[0266] Viering, Jentschura & Partner mbB

[0267] Blue-green algae of the species Spirulina, cultivated in a magnesium-enriched medium.

[0268] The extracts can be obtained by pressing the plants or individual plant parts. They can also be obtained using extraction agents. Water, alcohols, and mixtures thereof can be used as extraction agents for the production of the aforementioned plant extracts. Among the alcohols, lower alcohols such as ethanol and isopropanol, but especially polyhydric alcohols such as ethylene glycol, propylene glycol, and butylene glycol, are preferred, both as the sole extraction agent and in mixtures with water. Plant extracts based on water / propylene glycol in a ratio of 1:10 to 10:1 have proven particularly suitable. According to the invention, steam distillation is among the preferred extraction methods.

[0269] According to the invention, the plant extracts can be used in pure, dried form as well as in diluted or dissolved form. When used in diluted or dissolved form, they typically contain approximately 2–80% by weight of active substance and an anhydrous solvent, for example, anhydrous alcohols and / or glycols or, particularly preferably, at least one oil. Depending on the choice of solvent, it may be preferable to stabilize the plant extract by adding a solubilizer. Suitable solubilizers include, for example, ethoxylation products of optionally hydrogenated vegetable and animal oils, as well as PEG-free polyglycerol esters of medium-chain and long-chain fatty acids. Preferred solubilizers are ethoxylated mono-, di-, and triglycerides of C8-22 fatty acids with 4 to 50 ethylene oxide units, e.g.,hydrogenated ethoxylated castor oil, olive oil ethoxylate, almond oil ethoxylate, mink oil ethoxylate, polyoxyethylene glycol capryL / capric acid glycerides, polyoxyethylene glycerol monolaurate, polyoxyethylene glycol coconut fatty acid glycerides and polyglycerol esters such as polyglyceryl-6 caprylate, polyglyceryl-3 cocoate, polyglyceryl-4 caprate, polyglyceryl-6 ricinoleate, Polyglyceryl-3 Caprate / Caprylate / Succinate and Propylene Glycol.

[0270] Furthermore, it may be preferred to use mixtures of several, in particular two, three or four different plant extracts in the composition according to the invention for treating keratinous fibers. The use of dried, powdered plant extracts is particularly preferred. P93087WO August 11, 2025

[0271] Viering, Jentschura & Partner mbB

[0272] In one embodiment, the agent for treating keratinous fibers is a leave-in or leave-on treatment. This refers to hair treatment agents that are not immediately washed out after application, but remain temporarily in the hair.

[0273] In a preferred embodiment, the agent for treating keratinous fibers is selected from the group consisting of hairspray, hair conditioner, hair rinse, hairspray, hair treatment, hair tonic, heat protectant spray, styling powder, hair fibers, root concealer spray, concealer mascara, instant volumizing powder, mascara, eyebrow pencils, gels, mascaras and powders and brow fillers, products for taming baby hair and for scalp and beard care, color powder, pressed color powder, hair glow, styling balm, curl cream, hair mousse, hair gel, texture clay, gel wax, texturizing hair stick, pomade, 2-in-1 beard and hair pomade, hair styling cream, hair butter, hair wax, hair mask, 4-in-1 hair mask, hair oil, scalp care products in the sense of skinification of hair care, salon hair care and leave-on conditioner.

[0274] The well-known hair fibers consist of microfibers and are sprinkled on, distributed with the fingers, and fixed with hairspray. They stay in place during sports, perspiration, and in all kinds of weather. In contrast, the hair fibers according to the invention, made with lignin, are microfiber-free and therefore also microplastic-free, protect hair and scalp from UV radiation, and have an antioxidant effect.

[0275] As a UV-protective volumizing powder, the use of lignin eliminates the need for other ingredients such as silica silylate, PEGs, preservatives, perfumes or allergenic fragrances.

[0276] In the prior art, volumizing powders are known that contain at least silica silylate. A small amount of these is rubbed between the palms of the hands and then distributed and styled through the hair from roots to ends. This creates immediate volume. UV protection is not included. The volumizing powder according to the invention, containing lignin, does not contain silica silylate, preservatives such as sodium benzoate, or allergenic fragrances. Surprisingly, it was found that the feel of the hair is better and more pleasant, especially for fine hair, than with volumizing powders currently on the market.

[0277] In one embodiment, the lignin-containing agent can be used to treat keratinous fibers in the eyebrow area as a UV-protective eyebrow powder. - P93087WO 11 August 2025

[0278] Viering, Jentschura & Partner mbB paste, -mascara, -gel or as a so-called "brow filer" and in the area of ​​the eyelashes as eyelash mascara.

[0279] In the state of the art, for example, the Asam Magie Finish Perfect Brow Powder Kit Medium is a brow powder known to contain Tale, Mica, cornstarch and, among other things, three iron oxides.

[0280] Current eyebrow powders and mascaras do not contain UV protection. Dark eyebrows and dark eyelashes can become reddish or blonder / lighter in the sun.

[0281] Lignin particles and preparations containing them provide color, volume, and UV protection. According to the invention, keratin fiber treatments protect eyebrows and eyelashes from fading or discoloration in the sun, add volume, and fill in gaps in the eyebrows. Just as with head and beard hair, colored eyebrows and eyelashes are also possible. The eyebrow products according to the invention are applied with an eyebrow brush and distributed with an eyebrow spoolie. If necessary, the powdered product can be fixed with a water-based gel containing biopolymers, preferably with Caesalpinia spinosa gum (Tara gum), or applied from a suspension. Mascara containing lignin particles or colloidal lignin particles is applied with a brush.

[0282] The inventive agent for treating keratin fibers can also be used for baby hairs at the roots. The same applies as for eyebrow powder and mascara. The inventive agent for treating keratin fibers is applied with a small brush. It can be used with existing hair color ranging from dark blonde to dark brown or red, or any other bright hair color.

[0283] The agent according to the invention for the treatment of keratinous fibers can also be used as a silicone-free base lamination spray.

[0284] In the prior art, patching sprays such as "Magie Retouch Sofort" are known to contain isobutane, ethyl trisiloxane, CI 77491, CI 77492, CI 77499 / iron oxides, trimethylsiloxy-silicate, triethoxycaprylylsilane, and methyl trimethicone. (FIL C179939 / 1) (L'Oreal) and thus several silicones. This product is not abrasion-resistant. P93087WO August 11, 2025

[0285] Viering, Jentschura & Partner mbB

[0286] The temporary hair color according to the invention, which contains not only lignin particles but also color pigments, is sprayed onto the roots from an ethanolic suspension or as an aerosol and, if necessary, fixed in abrasion-resistant manner with hairspray, hair glow or with an aqueous spray solution containing biopolymers, preferably containing Caesalpinia Spinosa Gum (Tara Gum).

[0287] The agent according to the invention for the treatment of keratinous fibers can also be used as a concealing mascara with lignin without silicones.

[0288] Current state of the art includes concealing mascaras such as Magic Retouch (L'Oreal), which contain triethoxycaprylylsilane, dimethicone, amodimethicone, and three iron oxides: CI 77491, CI 77492, and CI 77499. Thanks to the film-forming properties of natural hair dyes on the hair, lignin-based hair mascaras can be formulated without silicones and, unlike silicone-based mascaras, possess UV-protective properties.

[0289] Other hair styling and hair care products with lignin for UV protection and natural color, and temporarily colored hair styling and hair care products with lignin:

[0290] UV protection for hair has so far only been seen in hairsprays (aerosols) on the market, according to current technology. Hairsprays with UV protection exist that contain organic, soluble UV filters.

[0291] These filter substances can leave a sticky feeling on skin and hair. If they are not photostable, breakdown products are formed. Inorganic UV filters such as titanium dioxide and zinc oxide leave a white cast on skin and hair and are therefore unsuitable for use on hair, or only suitable in combination with lignin. Furthermore, both filters are the subject of ongoing debate regarding nanoparticles. Lignin, on the other hand, as a macromolecule, offers UV protection, antioxidant properties, is non-sticky, does not leave a white cast, is photostable, and does not constitute nanoparticles.

[0292] Lignin and the color preparations according to the invention are applicable in hair styling spray, mousse, powder, gel, wax, cream, pomade, 2-in-1 pomade (beard and hair), texture clay for matte finish, texturizing hair stick, shine gel wax, matte finish, curl cream, styling balm, shine spray, hair conditioning oil, hair butter and in leave-in hair masks.

[0293] Aerosol and ethanolic sprays, hair mousse or sprayable multiphase preparations can be produced, various types of hydrogels and styling gels with polymers, emulsions and microemulsions, gel waxes, texture clay, P93087WO August 11, 2025

[0294] Viering, Jentschura & Partner mbB

[0295] Balms, hair masks and single-phase hydrophobic preparations such as hair oils, hair butters, pomades or waxes.

[0296] In an alternative embodiment, applications in the rinse-off segment are also possible, such as scalp scrub products, conditioners, shampoos, in 2-in-1 shampoos, as well as in solid shampoos and dry shampoos.

[0297] In a preferred embodiment, the agent for treating keratinous fibers is an agent for dyeing keratinous fibers, in particular human hair.

[0298] Since the lignin particles have an inherent coloration that varies depending on the starting material and ranges from light brown to brown, the agent for treating keratinous fibers can achieve hair coloring even without the addition of color pigments.

[0299] In a preferred embodiment, the agent for treating keratinous fibers additionally comprises at least one color pigment selected from natural pigments, organic pigments, colored metal oxides, metal hydroxides, metal oxide hydrates, silicates, metal sulfides, complex metal cyanides, metal sulfates, bronze pigments, and / or colored pigments based on silica, mica, or mica, coated with at least one metal oxide and / or a metal oxychloride. In a particularly preferred embodiment, the agent additionally comprises at least one color pigment from the group consisting of dryflux pigments, in which a very thin and homogeneous carbon layer is applied to the platelets of the pearlescent pigments, resulting in an extremely uniform appearance, and color travel pigments, which, as interference pigments, exhibit multiple iridescent color effects.

[0300] This allows for a wide range of color schemes.

[0301] Color pigments are generally understood to be insoluble, coloring substances. These are present in the coloring formulation in the form of small particles; these particles simply adhere to the outside of the hair fiber. They remain there until the next shampooing and can be completely removed by shampooing. Various products of this type are available on the market under the names hair mascara and hair chalk. P93087WO August 11, 2025

[0302] Viering, Jentschura & Partner mbB

[0303] Within the scope of the first three aspects of the invention, "pigments" or "color pigments" are, according to their use in temporary hair coloring, insoluble, coloring substances that enable coloring through physical adhesion to the keratin fibers. The "pigments" or "color pigments" of the first three aspects are expressly not oxidative dyes or their corresponding oxidative dye precursors such as developer components or coupler components. In permanent oxidative coloring, the developer components, under the influence of oxidizing agents or photooxygen, react with each other or with one or more coupler components to form the actual dyes.

[0304] In products for treating keratinous fibers, the color pigments are present in the form of small, undissolved particles that do not diffuse into the hair fiber, but are deposited on the outer wall of the keratin fiber under the influence of the lignin particles and are held there by a film of lignin particles.

[0305] The object of the present invention was to provide a versatile agent that enables the temporary color change of hair. The agent should be formulated so that it can be applied as a powder or pressed powder using a brush, as a suspension using a sponge, via a brush, and also by means of a spray application. Application as a hair mascara, hair butter, hair texturizing and conditioning cream, or leave-in hair mask is also preferred and should be selected according to the hair type. The color change should be simple and cause minimal damage, and should be completely removed from the hair by washing. Until the next hair wash, however, the product on the hair should be extremely resistant to external influences, i.e.,Neither rubbing against textiles nor combing should reveal any color loss or other product delamination. At the same time, hair colored in this way should have a soft feel, not be weighed down, not feel hard or greasy, and should not visually appear oily.

[0306] Surprisingly, it has been shown that these tasks can be solved by a carrier material in combination with color pigments when these are used with special water-insoluble lignin particles that are characterized by a small, defined particle size.

[0307] Suitable color pigments can be of organic and / or inorganic origin. P93087WO August 11, 2025

[0308] Viering, Jentschura & Partner mbB

[0309] Due to their excellent resistance to light, weather, and / or temperature, the use of inorganic color pigments is particularly preferred in the process according to the invention. The preferred average particle size of the color pigments—preferably inorganic—is 0.1 pm to 1 mm, more preferably 0.5 pm to 750 pm, and particularly 10 pm to 500 pm.

[0310] Preferred color pigments are selected from inorganic pigments, which can be of synthetic or natural origin. Inorganic color pigments of natural origin can be derived, for example, from chalk, ochre, umber, green earth, sapphire, burnt sienna, or graphite. Other inorganic color pigments that can be used include black pigments such as carbon black (CI 77266), iron oxide black, colored pigments such as ultramarine or iron oxide red, as well as fluorescent or phosphorescent pigments.

[0311] Particularly suitable are colored metal oxides, hydroxides and oxide hydrates, mixed-phase pigments, sulfur-containing silicates, silicates, metal sulfides, complex metal cyanides, metal sulfates, chromates and / or molybdates. Especially preferred color pigments are black iron oxide (CI 77499), yellow iron oxide (CI 77492), red and brown iron oxide (CI 77491), manganese violet (CI 77742), ultramarine (sodium aluminum sulfosilicates, CI 77007, Pigment Blue 29), chromium oxide hydrate (CI 77289), iron blue (ferric ferrocyanide, CI 77510), sapphire and / or carmine (cochineal).

[0312] Particularly preferred color pigments according to the invention are colored pearlescent pigments. These are typically based on silica, mica, and / or mica and can be coated with one or more metal oxides from the group consisting of titanium dioxide (CI 77891), black iron oxide (CI 77499), yellow iron oxide (CI 77492), red and / or brown iron oxide (CI 77491, CI 77499), manganese violet (CI 77742), ultramarine (sodium aluminum sulfosilicates, CI 77007, Pigment Blue 29), chromium oxide hydrate (CI 77289), chromium oxide (CI 77288), and / or iron blue (ferric ferrocyanide, CI 77510). Micas belong to the layered silicates. The most important representatives of these silicates are muscovite, phlogopite, paragonite, biotite, lepidolite, and margarite. To produce pearlescent pigments in combination with metal oxides, the mica, predominantly muscovite or phlogopite, is coated with a metal oxide.

[0313] As an alternative to natural mica, synthetic mica coated with one or more metal oxides can also be used as a pearlescent pigment. Such suitable pearlescent pigments based on natural mica are described in P93087WO dated August 11, 2025.

[0314] Viering, Jentschura & Partner mbB

[0315] The patent application WO 2005 / 065632 A1, to which explicit reference is made, describes particularly preferred pearlescent pigments based on natural or synthetic mica and coated with one or more of the aforementioned metal oxides. The color of the respective pigments can be varied by varying the thickness of the metal oxide layer(s).

[0316] In a further particularly preferred embodiment, a means according to the invention for treating keratinous fibers is characterized in that it contains at least one inorganic color pigment as a color pigment, which is selected from colored metal oxides, metal hydroxides, metal oxide hydrates, silicates, metal sulfides, complex metal cyanides, metal sulfates, bronze pigments and / or from colored pigments based on fluorphlogopite, silica, mica or mica, which are coated with at least one metal oxide and / or a metal oxychloride.In a particularly preferred embodiment, the composition contains at least one color pigment, a silica coated with a defined layer of iron oxide, a pigment from the group of dryflux pigments in which a very thin and homogeneous carbon layer is applied to the platelets of the pearlescent pigments, resulting in an extremely uniform appearance, and color travel pigments, which, as interference pigments, exhibit multiple iridescent color effects. These pigments are available with the INCI names mica, titanium dioxide (CI 77891), silica, carbon, tin oxide; titanium dioxide (CI 77891), mica, silica, carbon; and silica, CI 77491.

[0317] In a further particularly preferred embodiment, a composition according to the invention for treating keratinous fibers is characterized in that it contains at least one colored pigment based on silica, mica or mica as a color pigment, which is coated with one or more metal oxides from the group consisting of titanium dioxide (CI 77891), black iron oxide (CI 77499), yellow iron oxide (CI 77492), red and / or brown iron oxide (CI 77491, CI 77499), manganese violet (CI 77742), ultramarine (sodium aluminum sulfosilicates, CI 77007, Pigment Blue 29), chromium oxide hydrate (CI 77289), chromium oxide (CI 77288) and / or iron blue (ferric ferrocyanide, CI 77510).In a further particularly preferred embodiment, the composition contains at least one color pigment, a silica coated with a defined layer of iron oxide, a pigment from the group of dryflux pigments in which a very thin and homogeneous carbon layer is applied to the platelets of the pearlescent pigments, resulting in an extremely uniform appearance, and color travel pigments, which, as interference pigments, exhibit multiple iridescent color effects. These pigments are available with INCI P93087WO (dated August 11, 2025).

[0318] Viering, Jentschura & Partner mbB

[0319] Ingredients: Mica, titanium dioxide (CI 77891), silica, carbon, tin oxide; titanium dioxide (CI 77891), mica, silica, carbon; silica, CI 77491.

[0320] The color effects of the aforementioned pigments are particularly advantageous and clear when a refined coating technology is used that allows silica to be coated with a defined layer of iron oxide. In the Dryflux technology, a defined, fine, and very thin and homogeneous carbon layer is applied to the dry, powdery base substrate in a fluidized bed reactor. This technology makes it possible to produce stable, intensely colored effects in blue, green, and turquoise tones, as well as Color Travel pigments with a holographic green-blue color effect (see SOFW Journal 6, 4-8, (2024)).

[0321] Examples of particularly suitable color pigments are available commercially under the trade names Rona®, Colorona®, Dichrona®, Ronaflair®, Ronaflux®, Timiron® and Xirona® from Merck Electronics, Ariabel® and Unipure® from Sensient Beauty, Prestige® and Sumicos® from Sudarshan Europe BV, SynCrystal® from Eckart Effect Pigments (Eckardt GmbH in Germany), and SunSHINE® from Sun Chemical.

[0322] Ganz besonders bevorzugte Farbigmente mit der Handelsbezeichnung Colorona® sind beispielsweise: Colorona Copper, Merck, MICA, CI 77491 (IRON OXIDES), Colorona Passion Orange, Merck, Mica, CI 77491 (Iron Oxides), Alumina, Colorona Patina Silver, Merck, MICA, CI 77499 (IRON OXIDES), CI 77891 (TITANIUM DIOXIDE), Colorona RY, Merck, CI 77891 (TITANIUM DIOXIDE), MICA, CI 75470 (CARMINE), Colorona Oriental Beige, Merck, MICA, CI 77891 (TITANIUM DIOXIDE), CI 77491 (IRON OXIDES), Colorona Dark Blue, Merck, MICA, TITANIUM DIOXIDE, FERRIC FERROCYANIDE, Colorona Chameleon, Merck, CI 77491 (IRON OXIDES), MICA, Colorona Aborigine Amber, Merck, MICA, CI 77499 (IRON OXIDES), CI 77891 (TITANIUM DIOXIDE), Colorona Blackstar Blue, Merck, CI 77499 (IRON OXIDES), MICA, Colorona Patagonian Purple, Merck, MICA, CI 77491 (IRON OXIDES), CI 77891 (TITANIUM DIOXIDE), CI 77510 (FERRIC FERROCYANIDE), Colorona Red Brown, Merck, MICA, CI 77491 (IRON OXIDES), CI 77891 (TITANIUM DIOXIDE), Colorona Russet, Merck,CI 77491 (TITANIUM DIOXIDE), MICA, CI 77891 (IRON OXIDES), Colorona Imperial Red, Merck, MICA, TITANIUM DIOXIDE (CI 77891), D&C RED NO. 30 (CI 73360), Colorona Majestic Green, Merck, CI 77891 (TITANIUM DIOXIDE), MICA, CI 77288 (CHROMIUM OXIDE GREENS), Colorona Light Blue, Merck, MICA, TITANIUM DIOXIDE (CI 77891), FERRIC FERROCYANIDE (Cl 77510), Colorona Red Gold, Merck, MICA, Cl 77891 (TITANIUM DIOXIDE), Cl 77491 P93087WO 11. August 2025,

[0323] Viering, Jentschura & Partner mbB

[0324] (IRON OXIDES), Colorona Gold Plus MP 25, Merck, MICA, TITANIUM DIOXIDE (CI 77891), IRON OXIDES (CI 77491), Colorona Carmine Red, Merck, MICA, TITANIUM DIOXIDE, CARMINE, Colorona Blackstar Green, Merck, MICA, CI 77499 (IRON OXIDES), Colorona Bordeaux, Merck, MICA, CI 77491 (IRON OXIDES), Colorona Bronze, Merck, MICA, CI 77491 (IRON OXIDES), Colorona Bronze Fine, Merck, MICA, CI 77491 (IRON OXIDES), Colorona Fine Gold MP 20, Merck, MICA, CI 77891 (TITANIUM DIOXIDE), CI 77491 (IRON OXIDES), Colorona Sienna Fine, Merck, CI 77491 (IRON OXIDES), MICA, Colorona Sienna, Merck, MICA, CI 77491 (IRON OXIDES), Colorona Precious Gold, Merck, Mica, CI 77891 (Titanium dioxide), Silica, Cl 77491 (Iron oxides), Tin oxide, Colorona Sun Gold Sparkle MP 29, Merck, MICA, TITANIUM DIOXIDE, IRON OXIDES, MICA, Cl 77891 , Cl 77491 (EU), Colorona Mica Black, Merck, Cl 77499 (Iron oxides), Mica, Cl 77891 (Titanium dioxide), Colorona Bright Gold, Merck, Mica, Cl 77891 (Titanium dioxide), Cl 77491 (Iron oxides),Colorona Blackstar Gold, Merck, MICA, Cl 77499 (IRON OXIDES).,

[0325] Weiterhin besonders bevorzugte Farbpigmente mit der Handelsbezeichung Xirona® sind beispielsweise: Xirona Le Coeur, Merck, Silica, CI 77491 , Xirona Le Rouge, Merck, Iron Oxides, Silica, Xirona Carribean Blue, Merck, Mica, CI 77891 , Silica, Xirona Golden Sky, Merck, Silica, CI 77891 , Tin Oxide, Xirona Magie Mauve, Merck, Silica, CI 77891 , Tin Oxide, Xirona Moonlight Sparks, Merck, Calcium Aluminum Borosilicate, Silica, Cl 77891 , Tin Oxide, Xirona Nordic Sunset, Merck, Silica, Cl 77891 , Tin Oxide, Xirona Volcanic Fire, Merck, Silica, Cl 77891 , Tin Oxide, Xirona Volcanic Sparks, Merck, Calcium Aluminum Borosilicate, Silica, Cl 77891 , Tin Oxide.

[0326] Other particularly preferred color pigments with the trade name Ronaflux® include, for example: Ronaflux Specular Blue, Merck, Titanium Dioxide (CI 77891), Mica, Silica, Carbon; Ronaflux Specular Green, Merck, Titanium Dioxide (CI 77891), Mica, Silica, Carbon; Ronaflux Peacock, Merck, Mica, Titanium Dioxide (CI 77891), Silica, Carbon, Tin Oxide; Ronaflux Foxy Red, Merck, Silica, Iron Oxides, Carbon; Ronaflux Specular Silver, Merck, Mica, Titanium Dioxide (CI 77891), Carbon.

[0327] Weiterhin besonders bevorzugte Farbpigmente mit der Handelsbezeichnung SynCrystal® sind: SynCrystal Gold, Eckart, Synthetic Fluorphlogopite, Titanium Dioxide, Tin Oxide, SynCrystal Garnet, Eckart, Synthetic Fluorphlogopite, Iron Oxides, Tin Oxide, SynCrystal Jade, Eckart, Synthetic Fluorphlogopite, Titanium Dioxide, Iron Oxides, Ferric Ferrocyanide, Tin Oxide, SynCrystal Sapphire, Eckart, Synthetic Fluorphlogopite, Titanium Dioxide, Ferric Ferrocyanide, Tin Oxide, SynCrystal Very Berry, Eckart, Synthetic Fluorphlogopite, Iron Oxides, Titanium Dioxide, SynCrystal Soft Bronze, Eckardt, Synthetic P93087WO 11. August 2025

[0328] Viering, Jentschura & Partner mbB

[0329] Fluorphlogopite, Iron Oxides, SynCrystal Soft Black, Eckardt, Synthetic Fluorphlogopite, Iron Oxides.

[0330] Other particularly preferred color pigments with the trade name Unipure® include, for example: Unipure Red LC 381 EM, Sensient, CI 77491 (Iron Oxides), Silica; Unipure Brown LC 889, Sensient, Iron Oxides (77491), Iron Oxides (CI 77499); Unipure Black LC 989 EM, Sensient, CI 77499 (Iron Oxides), Silica; Unipure Yellow LC 182 EM, Sensient, CI 77492 (Iron Oxides), Silica.

[0331] In a further embodiment, the agent according to the invention for treating keratinous fibers can also contain one or more color-imparting compounds from the group of organic pigments.

[0332] The organic pigments according to the invention are correspondingly insoluble organic dyes or color lakes, which may be selected, for example, from the group consisting of nitroso, nitro, azo, xanthene, anthraquinone, isoindolinone, isoindolin, quinacridone, perinone, perylene, phthalocyanine, diketopyrrolopyrrole, indigo, thioindigo, dioxazine, and / or triarylmethane compounds.

[0333] Particularly suitable organic pigments include, for example, carmine, quinacridone, phthalocyanine, sorghum (dyer's millet), blue pigments with the Color Index numbers CI 42090, CI 69800, CI 69825, CI 73000, CI 74100, CI 74160, yellow pigments with the Color Index numbers C1 11680, C1 11710, C1 15985, C1 19140, CI 20040, CI 21100, CI 21108, CI 47000, CI 47005, green pigments with the Color Index numbers CI 61565, CI 61570, CI 74260, and orange pigments with the Color Index numbers CI 11725, CI 15510, CI 45370, CI 71105, red pigments with the color index numbers CI 12085, CI 12120, CI 12370, CI 12420, CI 12490, CI 14700, CI 15525, CI 15580, CI 15620, CI 15630, CI 15800, CI 15850, CI 15865, CI 15880, C17200, CI 26100, CI 45380, CI 45410, CI 58000, CI 73360, CI 73915 and / or CI 75470.

[0334] In a further particularly preferred embodiment, a composition according to the invention for treating keratinous fibers is characterized in that it contains at least one organic pigment, preferably selected from the group consisting of carmine, quinacridone, phthalocyanine, sorghum (dyer's millet), blue pigments with the color index numbers CI 42090, CI 69800, CI 69825, CI 73000, CI 74100, CI 74160, yellow pigments with the color index numbers C1 11680, C1 11710, C1 15985, C1 19140, CI 20040, CI 21100, CI 21108, CI 47000, CI 47005, and green pigments with the color index numbers P93087WO. (August 11, 2025)

[0335] Viering, Jentschura & Partner mbB

[0336] CI 61565, CI 61570, CI 74260, orange pigments with the color index numbers C11725, C15510, CI 45370, CI 71105, red pigments with the color index numbers CI 12085, CI 12120, CI 12370, CI 12420, CI 12490, CI 14700, CI 15525, CI 15580, CI 15620, C15630, CI 15800, CI 15850, CI 15865, CI 15880, CI 17200, CI 26100, CI 45380, CI 45410, CI 58000, CI 73360, CI 73915 and / or CI 75470.

[0337] The organic pigment can also be a paint lake. For the purposes of this invention, the term "paint lake" refers to particles comprising a layer of absorbed dyes, wherein the particle-dye unit is insoluble under the aforementioned conditions. These particles can be, for example, inorganic substrates such as aluminum, silica, calcium borosilicate, calcium aluminum borosilicate, or even aluminum itself.

[0338] For example, alizarin lacquer can be used as a colored lacquer.

[0339] Due to their excellent light and temperature resistance, the use of the aforementioned pigments in the composition according to the invention for treating keratinous fibers is particularly preferred. Furthermore, it is preferred if the pigments used have a specific particle size.

[0340] The mean particle size D50 can be determined, for example, using dynamic light scattering (DLS).

[0341] In an alternative embodiment, the color pigment can be a natural pigment. This is preferably selected from the group consisting of red henna, neutral henna, black henna, chamomile flower, sandalwood, black tea, green tea, buckthorn bark, sage, logwood, madder root, catechu, sedre, alkanet root, turmeric root, walnut shell, walnut leaves, senna leaves, indigo and / or cochineal.

[0342] In another embodiment, the color pigment can be an organic pigment selected from the group consisting of insoluble organic dyes or color lakes. These are preferably selected from the group consisting of nitroso, nitro, azo, xanthene, anthraquinone, isoindolinone, isoindolin, quinacridone, perinone, perylene, phthalocyanine, diketopyrrolopyrrole, indigo, thioindigo, dioxazine, and / or triarylmethane compounds. P93087WO August 11, 2025

[0343] Viering, Jentschura & Partner mbB

[0344] Particularly suitable organic pigments include, for example, carmine, quinacridone, phthalocyanine, sorghum (dyer's millet), blue pigments with the Color Index numbers CI 42090, CI 69800, CI 69825, CI 73000, CI 74100, CI 74160, yellow pigments with the Color Index numbers C1 11680, C1 11710, C1 15985, C1 19140, CI 20040, CI 21100, CI 21108, CI 47000, CI 47005, green pigments with the Color Index numbers CI 61565, CI 61570, CI 74260, and orange pigments with the Color Index numbers CI 11725, CI 15510, CI 45370, CI 71105, red pigments with the color index numbers CI 12085, CI 12120, CI 12370, CI 12420, CI 12490, CI 14700, CI 15525, CI 15580, CI 15620, CI 15630, CI 15800, CI 15850, CI 15865, CI 15880, C17200, CI 26100, CI 45380, CI 45410, CI 58000, CI 73360, CI 73915 and / or CI 75470.

[0345] In a further particularly preferred embodiment, the organic pigment is selected from the group consisting of carmine, quinacridone, phthalocyanine, sorghum (dyer's millet), blue pigments with the color index numbers CI 42090, CI 69800, CI 69825, CI 73000, CI 74100, CI 74160, yellow pigments with the color index numbers CI 11680, CI 11710, CI 15985, CI 19140, CI 20040, CI 21100, CI 21108, CI 47000, CI 47005, green pigments with the color index numbers CI 61565, CI 61570, CI 74260, and orange pigments with the color index numbers CI 11725, CI 15510, CI 45370, CI 71105, red pigments with the color index numbers C1 12085, C1 12120, C1 12370, C1 12420, C1 12490, CI 14700, CI 15525, CI 15580, CI 15620, C15630, CI 15800, CI 15850, CI 15865, CI 15880, C1 17200, CI 26100, CI 45380, CI 45410, CI 58000, CI 73360, CI 73915 and / or CI 75470.

[0346] Depending on the desired color change on the keratin fiber, the color pigment(s) can be used in varying quantities. Generally, the more color pigment used, the greater the degree of color change. However, beyond a certain amount, the adhesion of the pigments to the keratin fiber reaches a limit, after which it is no longer possible to increase the degree of color change by further increasing the amount of pigment used.

[0347] In this context, it has been found that when lignin particles are used—especially the aforementioned preferred and particularly preferred representatives—a film can be formed on the keratin fiber, which allows the color pigments to adhere to the keratin fiber in particularly large quantities. The inventive agents for treating keratin fibers can therefore contain the color pigments in a total amount of 0 to 60.0 wt%, preferably 1.0 to 50.0 wt%, more preferably 5.0 to 43.0 wt%, and particularly preferably 10 to 35 wt%. P93087WO August 11, 2025

[0348] Viering, Jentschura & Partner mbB

[0349] The compositions according to the invention for treating keratinous fibers can be formulated, for example, as a powder, a pressed powder, a stick, a suspension, a gel, a foamable gel, a lotion, a cream, a hair butter, a leave-in hair mask, a spray, an aerosol, or a pump foam. Depending on the application method, they are therefore preferably filled into a tube, a powder compact, a container, a bottle, a can, a pressurized container, or a container with a pump-spray applicator.

[0350] When the products are applied in powder form, as a hair gel, hair mask, or spray, the pigments can be applied particularly evenly to the keratin fibers. Therefore, formulations such as powder, pressed powder, leave-in hair mask, hair gel, hair butter, styling cream, hair oil, aerosol, or pump spray are especially preferred.

[0351] In the aforementioned preferred embodiment, the means according to the invention for treating keratinous fibers comprises a pressure vessel.

[0352] When applied in the form of a powder, a pressed powder, a hair gel, a leave-in hair mask, a hair butter, a styling cream, a hair oil, a pump spray or in the form of an aerosol spray, the user can brush or spray the inventive agents for the treatment of keratinous fibers directly onto dry hair and thus create the desired temporary color change.

[0353] Here, the user can first style their hair – for example, by combing, backcombing, or using a curling iron – and then spray on the inventive agent for treating keratin fibers. It is also possible to first apply or spray on the inventive agent for treating keratin fibers and then, or during this process, style the hair using the aforementioned methods. A second object of the present invention is therefore a method for temporarily coloring and changing the shape of hair, wherein an agent of the first object of the invention, which is formulated as a powder, a pressed powder, a hair gel, a leave-in hair mask, a hair butter, a styling cream, a hair oil, a pump spray, or an aerosol spray, is brushed or sprayed onto dry hair, and the hair is styled before or during application. P93087WO 11.August 2025.

[0354] Viering, Jentschura & Partner mbB

[0355] In a second aspect, the invention relates to the use of the agent according to the invention for the treatment of keratinous fibers in temporary dyes for human hair for intensive coloring, improvement of grey coverage, equalization, color intensity and / or durability of the dyes.

[0356] For this application, the hair coloring agent can be in any preparation form known to professionals. Preferably, it is selected from the group consisting of color fixative, color blow-dry lotion, color blow-dry foam, color rinse, color gel, color butter, or color cream.

[0357] In a third aspect, the invention relates to a method for the temporary coloring and shaping of hair, wherein the inventive agent for the treatment of keratinous fibers, which preferably contains at least one color pigment such as lignin particles, and which is formulated in the form of a powder, a pressed powder, a hair gel, a leave-in hair mask, a hair butter, a styling cream, a hair oil, a pump spray or aerosol sprays, is applied or sprayed onto dry hair and the hair is styled before or during the application.

[0358] According to a fourth aspect of the present invention, the stated problem is solved by providing an oxidation dye for dyeing keratinous fibers, in particular human hair, containing coupler components and developer components in a cosmetically acceptable carrier, wherein the coupler component is at least one lignin in the form of water-insoluble lignin particles having a mean particle size D50 of 100 nm to 100 pm.

[0359] In contrast to the first three aspects, this aspect provides an oxidation dye that can be used to achieve permanent coloring, especially of human hair.

[0360] Surprisingly, it has been shown that these tasks can be solved by using water-insoluble lignin particles as a coupler component in combination with the usual developer components.

[0361] The first essential component of the invention is lignin in the form of water-insoluble lignin particles, which have a mean particle size D50 of 100 nm to 100 pm. P93087WO 11 August 2025

[0362] Viering, Jentschura & Partner mbB

[0363] Lignin, as a polymeric molecule, does not penetrate deeply into the hair, but the lignin particles exhibit surprisingly good adhesion to keratin fibers, and especially to human hair. Coupling to the developer components leads to film formation on the hair surface.

[0364] With a size greater than 100 nm, the particles are not considered to be among the nanomaterials that pose a health risk. In fact, lignin, unlike the usual developer and coupler components of oxidative hair dyes, is harmless to health.

[0365] Due to their ability to increase the absorption of UV rays, lignin particles can act as a sunscreen booster for the hair and the underlying skin areas by enhancing the UV filtering effect of other UV filters contained within (so-called SPF booster effect).

[0366] Lignin is a free radical scavenger and antioxidant with antimicrobial properties, thus contributing to the protection of hair and scalp. Furthermore, lignin can bind lipophilic substances such as fats and oils, making it beneficial for oily hair and scalp.

[0367] Within the scope of the invention, it has surprisingly been shown that lignin particles with the particle size according to the invention can exhibit particularly advantageous properties for the oxidation dye. Among other things, these agents exhibit good application and spreadability and a pleasant feel in the hair, resulting in a comfortable hair texture and maintaining shine and dry combability.

[0368] In particular, a very good, uniform consistency of texture and spreadability of the colored hair is achieved, as well as a very good shine and conditioning effect.

[0369] Lignin is the largest natural, renewable source of aromatic compounds. However, the lignin produced in paper mills is currently hardly used as a material, but is mostly burned for energy production. The lignin used in this invention comes primarily from biorefineries for ethanol production or is derived from residual wood.

[0370] Depending on the starting material (hardwood, softwood, grasses), lignin particles possess varying degrees of inherent color and can therefore be used as coloring coupler components. The different lignin particles or colloidal lignin particles used according to the invention have a yellowish-brown color. P93087WO August 11, 2025

[0371] Viering, Jentschura & Partner mbB offers a reddish-brown and brown intrinsic color. A wide range of different colors can be achieved by adding further color pigments.

[0372] Lignin particles can be produced without the use of strong acids / bases and without the use of solvents, thus representing a natural and environmentally friendly ingredient with known positive properties, which is biodegradable and an alternative to fossil chemicals such as microplastics.

[0373] The oxidation dye according to the invention can also be combined with the known ingredients and in particular with known developer and coupler components and thus be specifically adapted to the respective application.

[0374] The oxidation dye, according to the fourth aspect, contains lignin in the form of water-insoluble lignin particles, with a mean particle size D50 of between 100 nm and 100 pm. According to this defined particle size, the lignin particles are present as a powder or, in the case of colloidal lignin particles, as an aqueous dispersion.

[0375] It is preferred to use either lignin particles with a mean particle size D50 of 5 pm to 100 pm, preferably with a particle size distribution D90 of less than 25 pm, or colloidal lignin particles with a mean particle size of 100 to 500 nm. A combination of these two lignin particle types is also possible.

[0376] Colloidal lignin particles are understood to be lignin particles which, as an aqueous dispersion, form a colloidal solution due to the uniform distribution of the particles.

[0377] The colloidal lignin particles preferably represent water-insoluble, sulfur-free lignin particles.

[0378] These particles are preferably obtained from an organosolv lignin. Methods for their production are described, for example, in WO 2020 / 000008 A1.

[0379] It has been shown that lignin particles of this size are both easy to process and exhibit beneficial adhesion to the hair fibers. Hair texture, shine, and combability are preserved by the particles.

[0380] The oxidation dye according to the invention is particularly suitable for fine, smooth, thick, smooth, wavy, brittle, curly, very curly, permed and frizzy hair. P93087WO 11 August 2025

[0381] Viering, Jentschura & Partner mbB

[0382] (Afro hair) as well as for beard hair, eyelashes and eyebrows, as the antioxidant effect of lignin provides protection for the dyed hair.

[0383] The properties of lignin can vary considerably and depend on the plant source and the isolation method. Depending on the plant source and isolation method, the lignin particles are soluble in different solvents. According to the invention, the lignin particles are water-insoluble.

[0384] Materials are considered “water-insoluble” if, when 100 g of the material is mixed with 100 g of deionized water and filtered at 20 °C under atmospheric pressure through a filter with a pore size of 0.2 pm to recover the liquid filtrate, after evaporation of 100 g of the liquid filtrate at 95 to 100 °C and ambient pressure, less than or equal to 0.1 g of recovered solid is obtained.

[0385] Furthermore, the oxidation dye according to the invention contains at least one developer component.

[0386] The two essential components of the aspect, lignin particles and developer component, are preferably present as a dispersion in a finely divided mixture of the lignin particles in the liquid solvent, which is preferably an aqueous, alcoholic or hydroalcoholic solvent.

[0387] The lignin particles can consist of lignin with a content of 75 to 95 wt% and cellulose and hemicellulose with a content of 5 to 25 wt%.

[0388] In one embodiment, the lignin particles contained in the oxidation dye according to the invention have a cellulose and hemicellulose or C5 and C6 monosaccharide content of less than 10% by weight. Depending on the starting material and isolation method, these sugars originate from the plant-based starting material and / or the enzymatic treatment of the material, which is carried out in particular by cellulase. It has been shown that a total C5 / C6 monosaccharide content of less than 10% significantly reduces the stickiness of the lignin.

[0389] Prominent C5 monosaccharides are arabinose and xylose, and prominent C6 monosaccharides are glucose, mannose, and galactose, so that the content of C5 and C6 monosaccharides can be approximately characterized by adding the contents of the five aforementioned sugars. P93087WO 11 August 2025

[0390] Viering, Jentschura & Partner mbB

[0391] In another embodiment, the lignin particles have a bulk density of 425 to 500 kg / m³. 3 Bulk density is the ratio of a material's mass to its volume, including the pores within the grains and the spaces between them. Bulk density depends primarily on the size of the individual particles. As the particle diameter decreases, the bulk density also changes.

[0392] In one embodiment, the lignin particles have a knock density of 500 to 550 kg / m³. 3When determining the tap density, a powder bed is compacted by impacts. After at least 1250 impacts, the final volume is considered reached. The ratio of bulk density to tap density indicates how much a powder can be compacted, i.e., how strong the resistance is to forming a densest packing. This reveals something about how well the powder particles slide past each other or how much this relative movement is hindered—for example, by the particle shape.

[0393] In another embodiment, the lignin particles have a shear stress of 100 to 250 Pa.

[0394] In one embodiment, the lignin particles have a contact friction angle of 30.0° to 35.0°, preferably of 30.5° to 32.5°.

[0395] In one embodiment, the lignin particles have a Carr index of 13.0 to 19.5. This gives the particles advantageous flow properties.

[0396] In another embodiment, the lignin particles have a flow index ff c from 5.0 to 18.0. This means the particles exhibit advantageous flow behavior.

[0397] In one embodiment, the lignin particles have a moisture content of less than 5 wt.% and preferably less than 3.5 wt.%.

[0398] In another embodiment, the lignin particles have a specific surface area (BET) of 0.5 to 100 m². 2 / g, preferably from 0.5 to 50 m 2 / g, especially preferably from 0.5 to 35 m 2 / g and especially preferably from 0.5 to 10 m 2 / g, determined according to DIN 66131 (with nitrogen).

[0399] In a preferred embodiment, the lignin contained in the oxidation dye is GS lignin and / or HGS lignin. These lignin types are preferably produced from hardwood, grasses, or monocotyledonous plants. P93087WO August 11, 2025

[0400] Viering, Jentschura & Partner mbB

[0401] Lignin is a high-molecular-weight, branched biopolymer composed of three aromatic building blocks: coniferyl alcohol (G), p-coumarin alcohol (H), and sinapyl alcohol (S). The lignin content and composition vary depending on the plant species.

[0402] Advantageous within the scope of the present invention is a high content of H units, i.e., of p-coumarin alcohol with two free ortho positions (positions 3 and 5 in the following figure), as well as as many free phenolic hydroxyl groups as possible. The second most advantageous is a high content of G units (coniferyl alcohol) with one free ortho position (at 5). p-Cumaryl alcohol (H) Coniferyl alcohol (G) Sinapyl alcohol (S).

[0403] Lignin from different wood and plant species differs in the proportions of alcohols and their derived phenyl groups: Coniferous lignin contains predominantly coniferyl units (approximately 90 percent), which possess a guaiacyl group (3-methoxy-4-hydroxyphenyl residue) and is therefore called G-lignin. Hardwood lignin contains varying proportions of guaiacyl groups and sinapyl units, which contain a syringyl group (3,5-methoxy-4-hydroxyphenyl residue). The syringyl content can range from 5 to 65 percent; the resulting lignins are called GS-lignin. The lignin of partially lignified grasses and other monocots is characterized by a high proportion of approximately 15 to 35 percent coumaryl elements, which form para-hydroxyphenylpropane and, together with a syringyl content of the same amount and a guaiacyl content of 50 to 70 percent, form the HGS lignins.

[0404] In a preferred embodiment, the lignin contained in the oxidation dye is deodorized lignin. "Deodorized lignin" is understood to mean lignin whose content of odor-causing compounds has been significantly reduced. For this purpose, the lignin is subjected to a deodorization process. P93087WO August 11, 2025

[0405] Viering, Jentschura & Partner mbB

[0406] The term "deodorization" refers to a reduction in the proportion of odor-causing compounds. Odor-causing compounds are generally volatile organic compounds (VOCs), which can be perceived by smell or detected through measurements in the gas phase. Specifically, VOCs are understood here to be volatile organic compounds that exhibit a high vapor pressure even at ambient temperature and can therefore readily diffuse from the substrate into the atmosphere. In the following, VOCs are understood to be organic components with a boiling point of 50–260 °C. Examples of VOCs are guaiacol and reduced organic sulfur compounds such as dimethyl disulfide and dimethyl trisulfide.The term "lignin deodorization" therefore refers to the reduction of the proportion of odor-causing volatile organic compounds (VOCs) or residues thereof derived from lignin. Deodorization leads to a reduction in the mass-based proportion of volatile organic compounds (VOCs) in the lignin substrate by at least 50%, preferably at least 60%, 70%, 80%, or at least 90%, and particularly preferably by at least 95%, 96%, 97%, 98%, or 99%. Methods for determining the proportion of volatile organic compounds (VOCs) in a lignin-containing substrate are familiar to those skilled in the art.

[0407] In a preferred embodiment, the lignin contained in the oxidation dye has been enzymatically pretreated with cellulase, so that the content of cellulose and C5 / C6 monosaccharides has been greatly reduced.

[0408] Enzymes and enzymatic treatment methods for cellulase treatment are familiar to experts. One example is the cellulase Cellic® CTec2 from Novonesis A / S (Denmark), which has an optimum reaction temperature of pH 5 and a temperature of 45 to 50°C. Preferably, the lignin-containing substrate undergoes multiple, i.e., at least two, enzymatic treatments with cellulase during pretreatment.

[0409] The term "lignin-containing substrate" refers to a material or mixture of materials that contains lignin. Examples of lignin-containing substrates include wood, straw, bagasse, bran, grass, etc. The lignin-containing substrate may also be a pre-treated substrate, such as waste from the sulfate or kraft processes commonly used in papermaking, or waste from lignin-containing substrates treated with organic aqueous solvents (organosolv process). The term "Kraft lignin" is also used in connection with such waste. (P93087WO 11 August 2025)

[0410] Viering, Jentschura & Partner mbB

[0411] The term "organosolv" lignin, also known as hydrolysis lignin, is used. Lignocellulose-containing biomass also falls under the category of "lignin-containing substrate." This refers to a material in which lignin is embedded in a framework formed from hemicelluloses and, primarily, cellulose.

[0412] In a preferred embodiment, the water-insoluble lignin is selected from the group consisting of natural lignin, Klason lignin, Kraft lignin, hydrolyzed lignin, ground wood lignin, soda lignin, organosolv lignin and aquasolv lignin, colloidal lignin and mixtures thereof.

[0413] Natural lignin is the lignin found in plant tissues and is also referred to as native lignin.

[0414] Klason lignin is the acid-insoluble lignin component of natural lignin. It is obtained by pre-hydrolysis of natural lignin in H₂SO₄, hydrolysis of the mixture at high temperatures, and filtration. The retentate contains the Klason lignin. The Klason process is known to those skilled in the art.

[0415] Hydrolyzed lignin is obtained by refluxing lignin or lignocellulose with HCl in a dioxane / water solution. This treatment leads to the degradation of lignin, forming significant amounts of arylpropanes, and the majority of the acidolysis monomers originate from the arylglycerol-β-aryl ether structure.

[0416] Ground wood lignin (MWL), also known as Björkman lignin, is obtained by grinding wood flour in a ball mill, either dry or in the presence of non-swelling solvents such as toluene, which destroys the cell structure of the wood. A portion of the lignin can be recovered from the suspension by extraction with a dioxane-water mixture. The Björkman process is known to those skilled in the art.

[0417] Kraft lignin is the lignin obtained through the Kraft process, also known as the Kraft pulp or sulfate process. This process converts wood into wood pulp, which consists of nearly pure cellulose fibers, the main component of paper, and is well-known to those skilled in the art. In the Kraft process, wood chips are treated with a hot mixture of water, sodium hydroxide (NaOH), and sodium sulfide (Na₂S), called white liquor, which breaks the bonds between lignin, hemicellulose, and cellulose. The technology involves several mechanical and chemical steps. P93087WO August 11, 2025

[0418] Viering, Jentschura & Partner mbB

[0419] Soda lignin is produced using the soda process, in which fibrous wood material is heated in a pressure reactor at high temperature in the presence of sodium hydroxide, also known as cooking liquor. During this process, the lignin is separated from the cellulose and suspended in the liquid phase, known as black liquor. The black liquor therefore contains both lignin and sodium hydroxide and is referred to as soda lignin.

[0420] Organosolv lignin is obtained through the organosolv process. In this process, lignin is extracted from lignocellulosic biomass using organic solvents, typically in combination with an acidic catalyst. Organosolv lignin contains no sulfur or sulfonate groups and has a molecular weight of approximately 1000 to 2000 g / mol.

[0421] In a particularly preferred embodiment, the lignin is an aquasolv lignin. An aquasolv lignin is defined as a lignin that has undergone hot water extraction. A major advantage of this process is that it eliminates the need for aggressive solvents and chemical additives, which significantly facilitates its use in cosmetic applications.

[0422] Hot water extraction refers to a thermal treatment using water at a temperature above 100 °C and a pressure above the vapor pressure of water at that temperature. Examples include temperatures of 100–250 °C at pressures of 1–50 bar, for example, a temperature of 200 °C at a pressure of 30 bar. Where the terms "hot water hydrolysis" or "hot water pretreatment" are also used here, they are synonymous with the term "hot water extraction" as described above.

[0423] Colloidal lignin is obtained by processing wood residues into organosolv-extracted lignin and then converting this into an aqueous dispersion of colloidal lignin particles with a particle size of approximately 100–500 nm through filtration and precipitation steps. A corresponding process is disclosed in WO 2020 / 000008 A1.

[0424] In a particularly preferred embodiment, the following four types of lignin particles can be used as the lignin component of the oxidation dye according to the invention: P93087WO 11 August 2025

[0425] Viering, Jentschura & Partner mbB

[0426] 1. Lignin particles produced from birch (Betula pendula) using the Aquasolv process and cellulase treatment, followed by spray drying, and exhibiting the following properties: a. Consisting of 75-95 wt% lignin, 5-25 wt% hemicellulose / cellulose; b. Total sugar content of xylose, glucose, mannose, galactose, arabinose of less than 10 wt%; c. Mean particle size D50 between 10 and 15 pm and D90 less than 25 pm; d. pH value between 5 and 7; e. Viscosity (10% in water) less than 100 mPas; f. Low polarity,

[0427] Such lignin particles are available, for example, as LignoBase Cool BE25 from the company Lignopure (Hamburg, Germany).

[0428] 2. Lignin particles produced from Scots pine (Pinus sylvestris) and spruce (Piceas abies) using the Aquasolv process and cellulase treatment, followed by spray drying, and exhibiting the following properties: a. Consisting of 75-95 wt% lignin, 5-25 wt% hemicellulose / cellulose; b. Total sugar content of xylose, glucose, mannose, galactose, and arabinose of less than 10 wt%; c. Mean particle size D50 between 10 and 15 pm and D90 less than 25 pm; d. pH value between 4.5 and 6.5; e. Viscosity (10% in water) less than 100 mPas; f. Medium polarity.

[0429] Such lignin particles are available, for example, as LignoBase Neutral PS25 from the company Lignopure (Hamburg, Germany).

[0430] 3. Lignin particles produced by alkaline pulping (soda pulping) of wheat straw (Triticum aestivum L.) and bamboo grass (Saccharum bengalense) followed by spray drying, with the following properties: a. Sulfate-free lignin consisting of 75-95 wt% lignin, 5-25 wt% hemicellulose / cellulose; b. Total content of the sugars xylose, glucose, mannose, galactose, arabinose of less than 10 wt%; c. Mean particle size D50 between 10 and 15 pm and D90 less than 25 pm; d. pH value between 3.0 and 5.0; e. Viscosity (10% in water) less than 100 mPas; P93087WO 11 August 2025

[0431] Viering, Jentschura & Partner mbB f. High polarity.

[0432] Lignin particles of this type are available, for example, as LignoBase Warm WS25 from the company Lignopure (Hamburg, Germany).

[0433] 4. Dispersion of colloidal lignin particles produced from birch (Betula pendula) by organosolv extraction with subsequent filtration and precipitation steps, and with the following properties: a. Sulfate-free lignin; b. Mean particle size D50 between 100 and 500 nm; c. Polydispersity index of less than 0.5; d. pH value between 3.0 and 6.0.

[0434] Such a dispersion is available, for example, as LignoGuard Aqua 20 from the company Lignovations GmbH (Klosterneuberg, Austria).

[0435] In the oxidation dye according to the invention, the lignin particles are present in a weight fraction of 0.1 to 99.9 wt.%, preferably 2 to 70 wt.%, particularly preferably 5 to 50 wt.%, and especially preferably 10 to 35 wt.%, in each case based on the total weight of the ready-to-use oxidation dye. The lignin particles can, for example, be present in a weight fraction of 1, 2, 3, 4,

[0436] May contain 5, 6, 7, 8, 9, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, or 65% by weight.

[0437] It has been shown that in ready-to-use oxidative dyes, lignin concentrations between 5 and 40 wt% are particularly advantageous for adhesion and coloring, without the hair becoming too woody at higher lignin concentrations and the color result being too weak.

[0438] Developer components

[0439] The developer components typically used are primary aromatic amines with an additional free or substituted hydroxy or amino group located in the para or ortho position, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazole derivatives, as well as 2,4,5,6-tetraaminopyrimidine and its derivatives.

[0440] According to the invention, it may be preferred to use a p-phenylenediamine derivative or one of its physiologically acceptable salts as the developer component. p-phenylenediamine derivatives of the formula (Ent1): P93087WO 11 August 2025 are particularly preferred.

[0441] Viering, Jentschura & Partner mbB where

[0442] G 1 stands for a hydrogen atom, a Ci to C4 alkyl group, a Ci to C4 monohydroxyalkyl group, a C2 to C4 polyhydroxyalkyl group, a (Ci to C4) alkoxy (Ci to C4) alkyl group, a 4'-aminophenyl group or a Ci to C4 alkyl group substituted with a nitrogen-containing group, a phenyl group or a 4'-aminophenyl group;

[0443] G 2stands for a hydrogen atom, a Ci to C4 alkyl group, a Ci to C4 monohydroxyalkyl group, a C2 to C4 polyhydroxyalkyl group, a (Ci to C4) alkoxy (Ci to C4) alkyl group or a Ci to C4 alkyl group substituted with a nitrogen-containing group;

[0444] G 3 stands for a hydrogen atom, a halogen atom such as a chlorine, bromine, iodine or fluorine atom, a Ci to C4 alkyl group, a Ci to C4 monohydroxyalkyl group, a C2 to C4 polyhydroxyalkyl group, a Ci to C4 hydroxyalkoxy group, a Ci to C4 acetylaminoalkoxy group, a Ci to C4 mesylaminoalkoxy group or a Ci to C4 carbamoylaminoalkoxy group;

[0445] G 4 stands for a hydrogen atom, a halogen atom, or a Ci to C4 alkyl group, or if G 3 and G 4 When positioned ortho to each other, they can together form a bridging α,γ-alkylenedioxo group, such as an ethylenedioxy group.

[0446] Examples of the C1 to C4 alkyl groups mentioned as substituents in the compounds according to the invention are the groups methyl, ethyl, propyl, isopropyl, and butyl. Ethyl and methyl are preferred alkyl groups. Preferred C1 to C4 alkoxy groups according to the invention are, for example, a methoxy or an ethoxy group. Furthermore, preferred examples of a C1 to C4 hydroxyalkyl group include a hydroxymethyl, a 2-hydroxyethyl, a 3-hydroxypropyl, or a 4-hydroxybutyl group. A 2-hydroxyethyl group is particularly preferred. A particularly preferred C2 to C4 polyhydroxyalkyl group is the 1,2-dihydroxyethyl group. Examples of halogen atoms P93087WO August 11, 2025

[0447] According to the invention, Viering, Jentschura & Partner mbB use F, CI, or Br atoms; Cl atoms are particularly preferred. The other terms used are derived from the definitions given herein. Examples of nitrogen-containing groups of formula (Ent1) are, in particular, amino groups, Ci to C4 monoalkylamino groups, Ci to C4 dialkylamino groups, Ci to C4 trialkylammonium groups, Ci to C4 monohydroxyalkylamino groups, imidazolinium, and ammonium.

[0448] Particularly preferred p-phenylenediamines of formula (Ent1) are selected from p-phenylenediamine, p-toluenediamine, 2-chloro-p-phenylenediamine, 2,3-dimethyl-p-phenylenediamine, 2,6-dimethyl-p-phenylenediamine, 2,6-diethyl-p-phenylenediamine, 2,5-dimethyl-p-phenylenediamine, N,N-dimethyl-p-phenylenediamine, N,N-diethyl-p-phenylenediamine, N,N-dipropyl-p-phenylenediamine, 4-amino-3-methyl-(N,N-diethyl)aniline, N,N-bis-(β-hydroxyethyl)-p-phenylenediamine, 4-N,N-bis-(β-hydroxyethyl)amino-2-methylaniline, 4-N,N-bis-(ß-hydroxyethyl)amino-2-chloroaniline, 2-(ß-hydroxyethyl)-p-phenylenediamine, 2-(a,ß-dihydroxyethyl)-p-phenylenediamine, 2-fluoro-p-phenylenediamine, 2-isopropyl-p-phenylenediamine, N-(ß-hydroxypropyl)-p-phenylenediamine, 2-Hydroxymethyl-p-phenylenediamine, N,N-dimethyl-3-methyl-p-phenylenediamine, N,N-(ethyl,ß-hydroxyethyl)-p-phenylenediamine, N-(ß,Y-dihydroxypropyl)-p-phenylenediamine, N-(4'-aminophenyl)-p-phenylenediamine, N-phenyl-p-phenylenediamine, 2-(ß-Hydroxyethyloxy)-p-phenylenediamine,2-(β-Acetylaminoethyloxy)-p-phenylenediamine, N-(β-Methoxyethyl)-p-phenylenediamine and 5,8-Diaminobenzo-1,4-dioxane and their physiologically acceptable salts.

[0449] According to the invention, particularly preferred p-phenylenediamine derivatives of formula (Ent1) are p-phenylenediamine, p-toluenediamine, 2-(β-hydroxyethyl)-p-phenylenediamine, 2-(α,β-dihydroxyethyl)-p-phenylenediamine and N,N-bis-(β-hydroxyethyl)-p-phenylenediamine.

[0450] According to the invention, it may further be preferred to use as a developer component compounds which contain at least two aromatic cores substituted with amino and / or hydroxyl groups.

[0451] Among the dinuclear developer components that can be used in the oxidation dye according to the invention, the compounds corresponding to the following formula (Ent2) and their physiologically acceptable salts can be mentioned in particular: P93087WO 11 August 2025

[0452] Viering, Jentschura & Partner mbB where:

[0453] Z 1 and Z 2 independently represent a hydroxyl or NH2 residue, which may be substituted by a Ci to C4 alkyl residue, by a Ci to C4 hydroxyalkyl residue and / or by a bridging Y, or which may be part of a bridging ring system; the bridging Y represents an alkylene group with 1 to 14 carbon atoms, such as a linear or branched alkylene chain or an alkylene ring, which may be interrupted or terminated by one or more nitrogen-containing groups and / or one or more heteroatoms such as oxygen, sulfur or nitrogen atoms, and may possibly be substituted by one or more hydroxyl or Ci to Cs alkoxy residues, or a direct bond.

[0454] G 5 and G 6stand independently for a hydrogen or halogen atom, a Ci to C4 alkyl group, a Ci to C4 monohydroxyalkyl group, a C2 to C4 polyhydroxyalkyl group, a Ci to C4 aminoalkyl group, or a direct connection for bridging Y,

[0455] G 7 , G 8 , G 9 , G 10 , G 11 and G 12 stand independently for a hydrogen atom, a direct bond to the bridge Y or a Ci to C4 alkyl group, with the stipulations that the compounds of formula (Ent2) contain only one bridge Y per molecule and the compounds of formula (Ent2) contain at least one amino group which carries at least one hydrogen atom.

[0456] The substituents used in formula (Ent2) are defined according to the invention analogously to the above statements. P93087WO 11 August 2025

[0457] Viering, Jentschura & Partner mbB

[0458] Preferred dinuclear developer components of formula (Ent2) are in particular: N,N'-Bis-(β-hydroxyethyl)-N,N'-bis-(4'-aminophenyl)-1,3-diamino-propan-2-ol, N,N'-Bis-(β-hydroxyethyl)-N,N'-bis-(4'-aminophenyl)-ethylenediamine, N,N'-Bis-(4-aminophenyl)-tetramethylenediamine, N,N'-Bis-(β-hydroxyethyl)-N,N'-bis-(4-aminophenyl)-tetramethylenediamine, N,N'-Bis-(4-methyl-aminophenyl)-tetramethylenediamine, N,N'-Diethyl-N,N'-bis-(4'-amino-3'-methylphenyl)-ethylenediamine, Bis-(2-hydroxy-5-aminophenyl)-methane, 1,3-Bis-(2,5- diaminophenoxy)-propan-2-ol, N,N'-Bis-(4'-aminophenyl)-1 ,4-diazacycloheptane, N,N'-Bis- (2-hydroxy-5-aminobenzyl)-piperazine, N-(4'-Aminophenyl)-p-phenylenediamine and 1 ,10-Bis- (2',5'-diaminophenyl)-1 ,4,7,10-tetraoxadecane and their physiologically acceptable salts.

[0459] Particularly preferred dinuclear developer components of formula (Ent2) are N,N'-Bis-(β-hydroxyethyl)-N,N'-bis-(4'-aminophenyl)-1,3-diamino-propan-2-ol, Bis-(2-hydroxy-5-aminophenyl)-methane, 1,3-Bis-(2,5-diaminophenoxy)-propan-2-ol, N,N'-Bis-(4'-aminophenyl)-1,4-diazacycloheptane and 1,10-Bis-(2',5'-diaminophenyl)-1,4,7,10-tetraoxadecane or one of their physiologically acceptable salts.

[0460] Furthermore, according to the invention, it may be preferred to use a p-aminophenol derivative or one of its physiologically acceptable salts as the developer component. p-Aminophenol derivatives of formula (Ent3) are particularly preferred: where:

[0461] G 13stands for a hydrogen atom, a halogen atom, a Ci to C4 alkyl group, a Ci to C4 monohydroxyalkyl group, a C2 to C4 polyhydroxyalkyl group, a (Ci to C4) alkoxy-(Ci to C4) alkyl group, a Ci to C4 aminoalkyl group, a hydroxy-(Ci to C4) alkylamino group, a Ci to C4 hydroxyalkoxy group, a Ci to C4 hydroxyalkyl-(Ci to C4) aminoalkyl group, or a (Di-Ci to C4 alkylamino)-(Ci to C4) alkyl group, and

[0462] G 14 stands for a hydrogen or halogen atom, a Ci to C4 alkyl group, a C1 to C4 monohydroxyalkyl group, a C2 to C4 polyhydroxyalkyl group, a (Ci to C4)- P93087WO 11 August 2025

[0463] Viering, Jentschura & Partner mbB

[0464] an alkoxy (Ci- to C4) alkyl group, a Ci- to C minoalkyl group, or a Ci- to C4 cyanoalkyl group,

[0465] G 15stands for hydrogen, a Ci to C4 alkyl group, a Ci to C4 monohydroxyalkyl group, a C2 to C4 polyhydroxyalkyl group, a phenyl group or a benzyl group, and

[0466] G 16 stands for hydrogen or a halogen atom.

[0467] The substituents used in formula (Ent3) are defined according to the invention analogously to the above statements.

[0468] Preferred p-aminophenols of formula (Ent3) are in particular p-aminophenol, N-methyl-p-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 2-hydroxymethylamino-4-aminophenol, 4-amino-3-hydroxymethylphenol, 4-amino-2-(n-hydroxyethoxy)phenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2-(β-hydroxyethyl-aminomethyl)phenol, 4-amino-2-(α,β-dihydroxyethyl)phenol, 4-amino-2-fluorophenol, 4-amino-2-chlorophenol, 4-amino-2,6-dichlorophenol, 4-amino-2-(diethyl-aminomethyl)phenol and their physiologically acceptable salts.

[0469] Particularly preferred compounds of formula (Ent3) are p-Aminophenol, 4-Amino-3-methylphenol, 4-Amino-2-aminomethylphenol, 4-Amino-2-(a,β-dihydroxyethyl)-phenol and 4-Amino-2-(diethyl-aminomethyl)-phenol.

[0470] Furthermore, the developer component can be selected from o-aminophenol and its derivatives, such as 2-amino-4-methylphenol, 2-amino-5-methylphenol or 2-amino-4-chlorophenol.

[0471] Furthermore, the developer component can be selected from heterocyclic developer components, such as the pyridine, pyrimidine, pyrazole, pyrazole-pyrimidine derivatives and their physiologically compatible salts.

[0472] Preferred pyridine derivatives are, in particular, the compounds described in patents GB 1026978 and GB1153196, such as 2,5-diaminopyridine, 2-(4'-methoxyphenyl)amino-3-aminopyridine, 2,3-diamino-6-methoxypyridine, 2-(β-methoxyethyl)amino-3-amino-6-methoxypyridine, and 3,4-diaminopyridine. P93087WO August 11, 2025

[0473] Viering, Jentschura & Partner mbB

[0474] Preferred pyrimidine derivatives are in particular the compounds described in German patent DE 2 359 399, Japanese patent application JP 02019576 A2 or in patent application WO 96 / 15765 A1, such as 2,4,5,6-tetraaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2-dimethylamino-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6-triaminopyrimidine. Preferred pyrazole derivatives are in particular the compounds described in patents DE 3 843 892, DE 4 133 957 and patent applications WO 94 / 08969, WO 94 / 08970, EP 0 740 931 and DE 195 43 988, such as 4,5-diamino-1-methylpyrazole, 4,5-diamino-1-(β-hydroxyethyl)pyrazole, 3,4-diaminopyrazole, 4,5-diamino-1-(4'-chlorobenzyl)pyrazole, 4,5-diamino-1,3-dimethylpyrazole, 4,5-diamino-3-methyl-1-phenylpyrazole, 4,5-diamino-1-methyl-3-phenylpyrazole, 4-amino-1,3-dimethyl-5-hydrazinopyrazole, 1 -Benzyl-4,5-diamino-3-methylpyrazole, 4, 5-diamino-3-tert.-butyl-1-methylpyrazole, 4,5-diamino-1-tert-butyl-3-methylpyrazole, 4,5-diamino-1-(ß-hydroxyethyl)-3-methylpyrazole, 4,5-diamino-1-ethyl-3-methylpyrazole, 4,5-diamino-1-ethyl-3-(4'-methoxyphenyl)pyrazole, 4,5-diamino-1-ethyl-3-hydroxymethylpyrazole, 4, 5-diamino-3-hydroxymethyl-1-methylpyrazole, 4,5-diamino-3-hydroxymethyl-1-isopropylpyrazole, 4,5-diamino-3-methyl-1-isopropylpyrazole, 4-amino-5-(y-aminoethyl)amino-1,3-dimethylpyrazole, 3,4,5-triaminopyrazole, 1-methyl-3,4,5- triaminopyrazole, 3,5-diamino-1-methyl-4-methylaminopyrazole and 3,5-diamino-4-(ß-hydroxyethyl)amino-1-methylpyrazole.

[0475] Preferred pyrazolopyrimidine derivatives are in particular the derivatives of the pyrazole-[1,5-a]-pyrimidine of the following formula (Ent4) and its tautomeric forms, provided that a tautomeric equilibrium exists: where:

[0476] G 17 , G 18 , G 19 and G 20Independently of each other, a hydrogen atom, a Ci to C4 alkyl group, an aryl group, a Ci to C4 hydroxyalkyl group, a C2 to C4 polyhydroxyalkyl group, a (Ci to C4) alkoxy-(Ci to C4) alkyl group, a Ci to C4 aminoalkyl group, optionally replaced by an acetyl ureide or a sulfonyl group, stand for a hydrogen atom, a Ci to C4 alkyl group, a (Ci to C4) alkoxy-(Ci to C4) alkyl group, a Ci to C4 aminoalkyl group, optionally replaced by an acetyl ureide or a sulfonyl group. P93087WO 11 August 2025

[0477] Viering, Jentschura & Partner mbB may be protected, a (Ci- to C4)-alkylamino-(Ci- to C4)-alkyl group, a di-[(Ci- to C4)-alkyl]-(Ci- to C4)-aminoalkyl group, wherein the dialkyl groups optionally form a carbon cycle or a heterocycle with 5 or 6 chain members, a Ci- to C4-hydroxyalkyl or a di-(Ci- to C4)-[hydroxyalkyl]-(Ci- to C4)-aminoalkyl group, the X groups independently representing a hydrogen atom, a Ci- to C4-alkyl group, an aryl group, a Ci- to C4-hydroxyalkyl group, a C2- to C4-polyhydroxyalkyl group, a Ci- to C4-aminoalkyl group, a (Ci- to C4)-alkylamino-(Ci- to C4)-alkyl group, a di-[(Ci- to C4)alkyl-(Ci- to C4)aminoalkyl group, wherein the dialkyl groups optionally form a carbon cycle or a heterocycle with 5 or 6 chain links, a Ci- to C4-hydroxyalkyl or a di-(Ci- to C4-hydroxyalkyl)aminoalkyl group, an amino group,a Ci- to C4-alkyl or di-(Ci- to C4-hydroxyalkyl)amino residue, a halogen atom, a carboxylic acid group or a sulfonic acid group, i has the value 0, 1, 2 or 3, p has the value 0 or 1, q has the value 0 or 1 and n has the value 0 or 1 , with the proviso that the sum of p + q is not equal to 0 if p + q equals 2, n has the value 0, and the groups NG, 17 G 18 and NG 19 G 20 The positions (2,3); (5,6); (6,7); (3,5) or (3,7) are occupied if p + q equals 1, n has the value 1, and the groups NG 17 G 18 (or NG) 19 G 20 ) and the group OH occupy positions (2,3); (5,6); (6,7); (3,5) or (3,7).

[0478] The substituents used in formula (Ent4) are defined according to the invention analogously to the above statements.

[0479] If the pyrazole-[1,5-a]-pyrimidine of the formula above (Ent4) contains a hydroxyl group at one of positions 2, 5 or 7 of the ring system, a tautomeric equilibrium exists, which is represented, for example, in the following scheme: P93087WO 11 August 2025

[0480] Viering, Jentschura & Partner mbB

[0481] Among the pyrazole-[1,5-a]-pyrimidines of the above formula (Ent4), the following can be mentioned in particular:

[0482] pyrazole-[1,5-a]-pyrimidine-3,7-diamine;

[0483] 2,5-Dimethyl-pyrazole-[1,5-a]-pyrimidine-3,7-diamine;

[0484] pyrazole-[1,5-a]-pyrimidine-3,5-diamine;

[0485] 2,7-Dimethyl-pyrazole-[1,5-a]-pyrimidine-3,5-diamine;

[0486] 3-Aminopyrazole-[1,5-a]-pyrimidin-7-ol;

[0487] 3-Aminopyrazole-[1,5-a]-pyrimidin-5-ol;

[0488] 2-(3-aminopyrazole-[1,5-a]-pyrimidin-7-ylamino)-ethanol;

[0489] 2-(7-Aminopyrazole-[1,5-a]-pyrimidin-3-ylamino)-ethanol;

[0490] 2-[(3-aminopyrazole-[1,5-a]-pyrimidin-7-yl)-(2-hydroxy-ethyl)amino]-ethanol;

[0491] 2-[(7-Aminopyrazole-[1,5-a]-pyrimidin-3-yl)-(2-hydroxy-ethyl)amino]-ethanol;

[0492] 5,6-Dimethylpyrazole-[1,5-a]-pyrimidine-3,7-diamine;

[0493] 2,6-Dimethylpyrazole-[1,5-a]-pyrimidine-3,7-diamine;

[0494] 3-Amino-7-dimethylamino-2,5-dimethylpyrazole-[1 ,5-a]-pyrimidine; as well as their physiologically acceptable salts and their tautomeric forms when a tautomeric equilibrium exists.

[0495] The pyrazole-[1 ,5-a]-pyrimidines of the above formula (Ent4) can be prepared as described in the literature by cyclization starting from an aminopyrazole or from hydrazine.

[0496] In a further embodiment of the present invention, the oxidation dye can contain at least one precursor of a nature-analogous dye. Preferably, indoles and indolines are used as precursors of nature-analogous dyes, having at least one hydroxyl or amino group, preferably as a substituent on the six-membered ring. These groups can bear further substituents, e.g., in the form of an etherification or esterification of the hydroxyl group or an alkylation of the P93087WO 11 August 2025

[0497] Viering, Jentschura & Partner mbB

[0498] Amino group. In a second preferred embodiment, the oxidation dye contains at least one indole and / or indoline derivative.

[0499] Derivatives of 5,6-dihydroxyindoline of the formula (Villa) are particularly well suited as precursors for natural-analogous hair dyes: (Villa) in which independently of each other

[0500] R 1stands for hydrogen, a C1-C4 alkyl group or a C1-C4 hydroxy alkyl group,

[0501] R 2 stands for hydrogen or a -COOH group, whereby the -COOH group can also exist as a salt with a physiologically acceptable cation,

[0502] R 3 stands for hydrogen or a C1-C4 alkyl group,

[0503] R 4 stands for hydrogen, a C1-C4 alkyl group, or a -CO-R group 6 , in the R 6 stands for a C1-C4 alkyl group, and

[0504] R 5 stands for one of the under R 4 the aforementioned groups, as well as physiologically acceptable salts of these compounds with an organic or inorganic acid.

[0505] Particularly preferred derivatives of indoline are 5,6-dihydroxyindoline, N-methyl-5,6-dihydroxyindoline, N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6-dihydroxyindoline, N-butyl-5,6-dihydroxyindoline, 5,6-dihydroxyindoline-2-carboxylic acid, as well as 6-hydroxyindoline, 6-aminoindoline and 4-aminoindoline.

[0506] Particularly noteworthy within this group are N-methyl-5,6-dihydroxyindoline, N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6-dihydroxyindoline, N-butyl-5,6-dihydroxyindoline, and especially 5,6-dihydroxyindoline. Derivatives of 5,6-dihydroxyindole of formula (Vllib): P93087WO 11 August 2025 are also excellently suited as precursors for natural-analogous hair dyes.

[0507] Viering, Jentschura & Partner mbB (Vlllb) in the independently of each other

[0508] R 1 stands for hydrogen, a Ci-C4 alkyl group or a Ci-C4 hydroxyalkyl group,

[0509] R 2stands for hydrogen or a -COOH group, whereby the -COOH group can also exist as a salt with a physiologically acceptable cation,

[0510] R 3 stands for hydrogen or a Ci-C4 alkyl group,

[0511] R 4 stands for hydrogen, a Ci-C4 alkyl group, or a -CO-R group 6 , in the R 6 stands for a Ci-C4 alkyl group, and

[0512] R 5 stands for one of the groups mentioned under R4, as well as physiologically acceptable salts of these compounds with an organic or inorganic acid.

[0513] Particularly preferred derivatives of indole are 5,6-dihydroxyindole, N-methyl-5,6-dihydroxyindole, N-ethyl-5,6-dihydroxyindole, N-propyl-5,6-dihydroxyindole, N-butyl-5,6-dihydroxyindole, 5,6-dihydroxyindol-2-carboxylic acid, 6-hydroxyindole, 6-aminoindole and 4-aminoindole.

[0514] Of particular note within this group are N-methyl-5,6-dihydroxyindol, N-ethyl-5,6-dihydroxyindol, N-propyl-5,6-dihydroxyindol, N-butyl-5,6-dihydroxyindol and especially 5,6-dihydroxyindol.

[0515] Coupler components

[0516] In a further preferred embodiment, the oxidation dye according to the invention contains at least one further coupler component.

[0517] The coupler components typically used are m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones, and m-aminophenol derivatives. Particularly suitable coupler components include 1-naphthol, 1,5-, 2,7-, and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 1-phenyl-3-methylpyrazolone-5, 2,4-dichloro-3-aminophenol, 1,3-bis-(2',4'-diaminophenoxy)propane, 2-chlororesorcinol, 4-chlororesorcinol, 2-P93087WO 11 August 2025

[0518] Viering, Jentschura & Partner mbB

[0519] Chloro-6-methyl-3-aminophenol, 2-amino-3-hydroxypyridine, 2-methylresorcinol, 5-methylresorcinol and 2-methyl-4-chloro-5-aminophenol.

[0520] Preferred coupler components according to the invention are m-aminophenol and its derivatives such as 5-amino-2-methylphenol, N-cyclopentyl-3-aminophenol, 3-amino-2-chloro-6-methylphenol, 2-hydroxy-4-aminophenoxyethanol, 2,6-dimethyl-3-aminophenol, 3-trifluoroacetylamino-2-chloro-6-methylphenol, 5-amino-4-chloro-2-methylphenol, 5-amino-4-methoxy-2-methylphenol, 5-(2'-hydroxyethyl)amino-2-methylphenol, 3-(diethylamino)phenol, N-cyclopentyl-3-aminophenol, 1,3-dihydroxy-5-(methylamino)benzene, 3-ethylamino-4-methylphenol and 2,4-dichloro-3-aminophenol, o-aminophenol and its derivatives, m-diaminobenzene and its derivatives such as 2,4-Diaminophenoxyethanol, 1,3-Bis-(2',4'-diaminophenoxy)-propane, 1-Methoxy-2-amino-4-(2'-hydroxyethylamino)benzene, 1,3-Bis-(2',4'-diaminophenyl)-propane, 2,6-Bis-(2'-hydroxyethylamino)-1-methylbenzene and 1-Amino-3-bis-(2'-hydroxyethyl)aminobenzene, o-Diaminobenzene and its derivatives such as 3,4-diaminobenzoic acid and 2,3-Diamino-1-methylbenzene, di- or trihydroxybenzene derivatives such as resorcinol, resorcinol monomethyl ether, 2-methylresorcinol, 5-methylresorcinol, 2,5-dimethylresorcinol, 2-chlororesorcinol, 4-chlororesorcinol, pyrogallol and 1,2,4-trihydroxybenzene, pyridine derivatives such as 2,6-dihydroxypyridine, 2-amino-3-hydroxypyridine, 2-amino-5-chloro-3-hydroxypyridine, 3-amino-2-methylamino-6-methoxypyridine, 2,6-dihydroxy-3,4-dimethylpyridine, 2,6-dihydroxy-4-methylpyridine, 2,6-diaminopyridine, 2,3-diamino-6-methoxypyridine and 3,5-diamino-2,6-dimethoxypyridine, Naphthalene derivatives such as 1-naphthol, 2-methyl-1-naphthol, 2-hydroxymethyl-1-naphthol, 2-hydroxyethyl-1-naphthol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 1,8-dihydroxynaphthalene, 2,7- dihydroxynaphthalene and 2,3-dihydroxynaphthalene,

[0521] Morpholine derivatives such as 6-hydroxybenzomorpholine and 6-aminobenzomorpholine, quinoxaline derivatives such as 6-methyl-1,2,3,4-tetrahydroquinoxaline, pyrazole derivatives such as 1-phenyl-3-methylpyrazol-5-one, indole derivatives such as 4-hydroxyindole, 6-hydroxyindole and 7-hydroxyindole, pyrimidine derivatives such as 4,6-diaminopyrimidine, 4-amino-2,6-dihydroxypyrimidine, 2,4-diamino-6-hydroxypyrimidine, 2,4,6-trihydroxypyrimidine, 2- P93087WO 11 August 2025

[0522] Viering, Jentschura & Partner mbB

[0523] Amino-4-methylpyrimidine, 2-amino-4-hydroxy-6-methylpyrimidine and 4,6-dihydroxy-2-methylpyrimidine, or

[0524] Methylenedioxybenzene derivatives such as 1-hydroxy-3,4-methylenedioxybenzene, 1-amino-3,4-methylenedioxybenzene and 1-(2'-hydroxyethyl)amino-3,4-methylenedioxybenzene.

[0525] Particularly preferred coupler components according to the invention are 1-naphthol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 3-aminophenol, 5-amino-2-methylphenol, 2-amino-3-hydroxypyridine, resorcinol, 4-chlororesorcinol, 2-chloro-6-methyl-3-aminophenol, 2-methylresorcinol, 5-methylresorcinol, 2,5-dimethylresorcinol and 2,6-dihydroxy-3,4-dimethylpyridine.

[0526] In a further preferred embodiment, the oxidation dye according to the invention further comprises at least one direct dye.

[0527] Preferred direct dyes used in the oxidation dyes according to the invention are nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols. Preferred direct dyes are those under the international names or trade names HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, HC Yellow 12, Acid Yellow 1, Acid Yellow 10, Acid Yellow 23, Acid Yellow 36, HC Orange 1, Disperse Orange 3, Acid Orange?, HC Red 1, HC Red 3, HC Red 10, HC Red 11, HC Red 13, Acid Red 33, Acid Red 52, HC Red BN, Pigment Red 57:1, HC Blue 2, HC Blue 12, Disperse Blue 3, Acid Blue 7, Acid Green 50, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Acid Violet 43, Disperse Black 9, Acid Black 1, and Acid Black 52 known compounds as well as 1,4- Diamino-2-nitrobenzene, 2-amino-4-nitrophenol, 1,4-bis-(ß-hydroxyethyl)amino-2-nitrobenzene, 3-nitro-4-(ß-hydroxyethyl)aminophenol, 2-(2'-hydroxyethyl)amino-4,6-dinitrophenol,1-(2'-Hydroxyethyl)amino-4-methyl-2-nitrobenzene, 1-Amino-4-(2'-hydroxyethyl)amino-5-chloro-2-nitrobenzene, 4-Amino-3-nitrophenol, 1-(2'-Ureidoethyl)amino-4-nitrobenzene, 4-Amino-2-nitrodiphenylamine-2'-carboxylic acid, 6-Nitro-1,2,3,4-tetrahydroquinoxaline, 2-Hydroxy-1,4-naphthoquinone, picramic acid and its salts, 2-Amino-6-chloro-4-nitrophenol, 4-Ethylamino-3-nitrobenzoic acid and 2-Chloro-6-ethylamino-1-hydroxy-4-nitrobenzene.

[0528] In a preferred embodiment, the oxidation dye according to the invention contains a cationic direct dye. Particularly preferred are P93087WO 11 August 2025

[0529] Viering, Jentschura & Partner mbB

[0530] (a) cationic triphenylmethane dyes, such as Basic Blue 7, Basic Blue 26, Basic Violet 2 and Basic Violet 14,

[0531] (b) aromatic systems substituted with a quaternary nitrogen group, such as Basic Yellow 57, Basic Red 76, Basic Blue 99, Basic Brown 16 and Basic Brown 17, as well as

[0532] (c) Direct-drawing dyes containing a heterocycle having at least one quaternary nitrogen atom, such as those mentioned, for example, in claims 6 to 11 of EP 0 998908 A2, to which explicit reference is made here. Preferred cationic direct-drawing dyes of group (c) are in particular the following compounds: P93087WO August 11, 2025

[0533] Viering, Jentschura & Partner mbB

[0534] The compounds of formulas (DZ1), (DZ3) and (DZ5), also known as Basic Yellow 87, Basic Orange 31 and Basic Red 51, are particularly preferred cationic direct dyes of group (c).

[0535] The cationic direct dyes marketed under the trademark Arianor® are also particularly preferred cationic direct dyes according to the invention. P93087WO August 11, 2025

[0536] Viering, Jentschura & Partner mbB

[0537] The compositions according to this embodiment of the invention preferably contain the direct dyes in an amount of 0.01 to 20 wt.%, based on the total oxidation dye.

[0538] Furthermore, the preparations according to the invention can also contain naturally occurring dyes such as those found, for example, in red henna, neutral henna, black henna, chamomile flower, sandalwood, black tea, buckthorn bark, sage, logwood, madder root, catechu, sedre and alkanna root.

[0539] It is not necessary for the oxidation dye precursors or the direct dyes to each be uniform compounds. Rather, the compositions according to the invention may contain further components in minor quantities due to the manufacturing processes for the individual dyes, provided that these do not adversely affect the dyeing result or must be excluded for other reasons, e.g., toxicological ones.

[0540] With regard to the dyes of this aspect that can be used in the hair dyeing and tinting products according to the invention, further express reference is made to the monograph Ch. Zviak, "The Science of Hair Care", Chapter 7 (pages 248-250; direct dyes) and Chapter 8, pages 264-267; oxidation dye precursors), published as Volume 7 of the series "Dermatology" (editors: C. Culnan and H. Maibach), Marcel Dekker Inc., New York, Basel, 1986, as well as to the Cosmetics Regulation (Regulation (EC) 1223 / 2009) with a positive list (Annex IV).

[0541] The oxidation dyes according to the invention can further contain all active ingredients, additives, and excipients known for such preparations. In many cases, the dyes contain at least one surfactant, whereby in principle anionic, zwitterionic, ampholytic, nonionic, and cationic surfactants are all suitable. However, in many cases, it has proven advantageous to select the surfactants from anionic, zwitterionic, or nonionic surfactants.

[0542] In preparations according to the invention, all anionic surfactants suitable for use on the human body are suitable as anionic surfactants in this respect. These are characterized by a water-soluble anionic group, such as a carboxylate, sulfate, sulfonate, or phosphate group, and a lipophilic alkyl group with approximately 10 to 22 carbon atoms. Additionally, the molecule P93087WO 11 August 2025

[0543] Viering, Jentschura & Partner mbB

[0544] May contain glycol or polyglycol ether groups, ester, ether and amide groups, as well as hydroxyl groups.

[0545] Examples of suitable anionic surfactants are, in the form of sodium, potassium, and ammonium salts, as well as mono-, di-, and trialkanolammonium salts with 2 or 3 carbon atoms in the alkanol group; linear fatty acids with 10 to 22 carbon atoms (soaps); ether carboxylic acids of the formula RO-(CH2-CH2O)x-CH2-COOH, in which R is a linear alkyl group with 10 to 22 carbon atoms and x = 0 or 1 to 16; acyl sarcosides with 10 to 18 carbon atoms in the acyl group; acyl taurides with 10 to 18 carbon atoms in the acyl group; acylisethionates with 10 to 18 carbon atoms in the acyl group; and sulfosuccinic acid mono- and dialkyl esters with 8 to 18 carbon atoms in the alkyl group. Sulfosuccinic acid monoalkyl polyoxyethyl esters with 8 to 18 carbon atoms in the alkyl group and 1 to 6 oxyethyl groups, linear alkanesulfonates with 12 to 18 carbon atoms, linear alpha-olefin sulfonates with 12 to 18 carbon atoms, alpha-sulfofaticial methyl esters of fatty acids with 12 to 18 carbon atoms,Alkyl sulfates and alkyl polyglycol ether sulfates of the formula RO-(CH2-CH2O)x-SO3H, in which R is a preferably linear alkyl group with 10 to 18 C atoms and x = 0 or 1 to 12,

[0546] Mixtures of surfactant hydroxysulfonates according to DE-A-37 25 030, sulfated hydroxyalkyl polyethylene and / or hydroxyalkylene propylene glycol ethers according to DE-A-37 23 354,

[0547] Sulfonates of unsaturated fatty acids with 12 to 24 carbon atoms and 1 to 6 double bonds according to DE-A-39 26 344,

[0548] Esters of tartaric acid and citric acid with alcohols, which are addition products of about 2-15 molecules of ethylene oxide and / or propylene oxide to fatty alcohols with 8 to 22 carbon atoms.

[0549] Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates, and ether carboxylic acids with 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule, and in particular salts of saturated and especially unsaturated Cs-C22 carboxylic acids, such as oleic acid, stearic acid, isostearic acid, and palmitic acid. P93087WO 11 August 2025

[0550] Viering, Jentschura & Partner mbB

[0551] Preferred surfactants continue to be glycolipids such as sophorolipids in lactone and open-chain form, as well as rhamnolipids, mannosylerythritol lipids (MEL), cellobiose lipids (CL) and trehalose lipids (TL).

[0552] Nonionic surfactants contain, as a hydrophilic group, for example, a polyol group, a polyalkylene glycol ether group, or a combination of polyol and polyglycol ether groups. Examples of such compounds are...

[0553] Addition products of 2 to 30 mol of ethylene oxide and / or 0 to 5 mol of propylene oxide to linear fatty alcohols with 8 to 22 carbon atoms, to fatty acids with 12 to 22 carbon atoms and to alkylphenols with 8 to 15 carbon atoms in the alkyl group, Ci2-C22 fatty acid mono- and diesters of addition products of 1 to 30 mol of ethylene oxide to glycerol,

[0554] C2-C22 alkyl mono- and oligoglycosides and their ethoxylated analogues, as well as adsorption products of 5 to 60 mol of ethylene oxide to castor oil and hydrogenated castor oil.

[0555] Preferred nonionic surfactants are alkyl polyglycosides of the general formula R 1 O- (Z)x. These compounds are characterized by the following parameters.

[0556] The alkyl group R 1It contains 6 to 22 carbon atoms and can be either linear or branched. Primary linear and 2-methyl-branched aliphatic residues are preferred. Examples of such alkyl residues are 1-octyl, 1-decyl, 1-lauryl, 1-myristyl, 1-cetyl, and 1-stearyl. 1-octyl, 1-decyl, 1-lauryl, and 1-myristyl are particularly preferred. When using so-called "oxo alcohols" as starting materials, compounds with an odd number of carbon atoms in the alkyl chain predominate.

[0557] The alkyl polyglycosides usable according to the invention can, for example, only contain a specific alkyl group R. 1 These compounds are typically produced from natural fats and oils or mineral oils. In this case, the alkyl groups R are mixtures corresponding to the starting compounds or to the respective processing of these compounds.

[0558] Particularly preferred are those alkyl polyglycosides in which R 1

[0559] - essentially consisting of Cs and Cw alkyl groups,

[0560] - consisting primarily of C12 and C14 alkyl groups,

[0561] - essentially consisting of Cs to Cis alkyl groups or

[0562] - consists essentially of C12 to cis alkyl groups. P93087WO 11 August 2025

[0563] Viering, Jentschura & Partner mbB

[0564] Any mono- or oligosaccharide can be used as the sugar building block Z. Sugars with 5 or 6 carbon atoms, as well as the corresponding oligosaccharides, are typically used. Examples of such sugars are glucose, fructose, galactose, arabinose, ribose, xylose, lyxose, allose, altrose, mannose, gulose, idose, talose, and sucrose. Preferred sugar building blocks are glucose, fructose, galactose, arabinose, and sucrose; glucose is particularly preferred.

[0565] The alkyl polyglycosides usable according to the invention contain on average 1.1 to 5 sugar units. Alkyl polyglycosides with x-values ​​of 1.1 to 1.6 are preferred. Alkyl glycosides with x-values ​​of 1.1 to 1.4 are particularly preferred.

[0566] In addition to their surfactant effect, alkyl glycosides can also serve to improve the fixation of fragrance components on the hair. Therefore, if a longer-lasting effect of the perfume oil on the hair beyond the duration of the hair treatment is desired, a person skilled in the art would preferably use this class of substances as a further ingredient in the preparations according to the invention.

[0567] The alkoxylated homologs of the aforementioned alkyl polyglycosides can also be used according to the invention. These homologs can contain an average of up to 10 ethylene oxide and / or propylene oxide units per alkyl glycoside unit.

[0568] Furthermore, zwitterionic surfactants can be used, particularly as co-surfactants. Zwitterionic surfactants are defined as surface-active compounds that contain at least one quaternary ammonium group and at least one -GOGH or -SO3H group in their molecule. Particularly suitable zwitterionic surfactants include the so-called betaines, such as the N-alkyl-N,N-dimethylammonium glycinates (e.g., cocoalkyl-dimethylammonium glycinate), N-acyl-aminopropyl-N,N-dimethylammonium glycinates (e.g., cocoacylaminopropyl dimethylammonium glycinate), and 2-alkyl-3-carboxylmethyl-3-hydroxyethyl-imidazolines, each with 8 to 18 carbon atoms in the alkyl or acyl group, as well as cocoacylaminoethylhydroxyethylcarboxymethyl glycinate. A preferred zwitterionic surfactant is the fatty acid amide derivative known under the INCI name cocamidopropyl betaine.

[0569] Ampholytic surfactants are also particularly suitable as co-surfactants. Ampholytic surfactants are defined as surface-active compounds that, in addition to a Cs-Cis alkyl or acyl group in the molecule, contain at least one free amino group. P93087WO 11 August 2025

[0570] Viering, Jentschura & Partner mbB and contain at least one -COOH or -SChH group and are capable of forming internal salts. Examples of suitable ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids, and alkylaminoacetic acids, each with approximately 8 to 18 carbon atoms in the alkyl group. Particularly preferred ampholytic surfactants are N-cocosalkylaminopropionate, cocosacylaminoethylaminopropionate, and Ci2-18-acylsarcosine.

[0571] According to the invention, cationic surfactants of the type of quaternary ammonium compounds, esterquats and amidoamines are used in particular.

[0572] Preferred quaternary ammonium compounds are ammonium halides, in particular chlorides and bromides, such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, e.g. cetyltrimethylammonium chloride, stearyltrimethylammonium chloride,

[0573] distearyldimethylammonium chloride, lauryldimethylammonium chloride,

[0574] Lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride, as well as the imidazolium compounds known under the INCI names Quaternium-27 and Quaternium-83. The long alkyl chains of the surfactants mentioned above preferably have 10 to 18 carbon atoms.

[0575] Esterquats are known substances that contain at least one ester group and at least one quaternary ammonium group as a structural element. Preferred esterquats are quaternary ester salts of fatty acids with triethanolamine, quaternary ester salts of fatty acids with diethanolalkylamines, and quaternary ester salts of fatty acids with 1,2-dihydroxypropyldialkylamines. Such products are marketed, for example, under the trademarks Stepantex®, Dehyquart®, and Armocare®.

[0576] The products Armocare® VGH-70, an N,N-bis(2-palmitoyloxyethyl)dimethylammonium chloride, as well as Dehyquart® F-75 and Dehyquart® All-35 are examples of such esterquats.

[0577] Alkylamidoamines are typically produced by the amidation of natural or synthetic fatty acids and fatty acid fractions with dialkylaminoamines. A particularly suitable compound from this group of substances according to the invention is P93087WO 11 August 2025

[0578] Viering, Jentschura & Partner mbB presents stearamidopropyldimethylamine, which is commercially available under the name Tegoamid® S 18.

[0579] Other cationic surfactants that can be used according to the invention are the quaternized protein hydrolysates.

[0580] According to the invention, cationic silicone oils such as the commercially available products Q2-7224 (manufacturer: Dow Corning; a stabilized trimethylsilylamodimethicone), Dow Corning 929 Emulsion (containing a hydroxylamino-modified silicone, also known as amodimethicone), SM-2059 (manufacturer: Momentive Performance Materials), SLM-55067 (manufacturer: Wacker) and Abil®-Quat 3270 and 3272 (manufacturer: Evonik; diquaternary polydimethylsiloxanes, Quaternium-80) are also suitable.

[0581] An example of a quaternary sugar derivative that can be used as a cationic surfactant is the commercial product Glucquat®100, which according to INCI nomenclature is a "Lauryl Methyl Gluceth-10 Hydroxypropyl Dimonium Chloride".

[0582] The compounds with alkyl groups used as surfactants can each be a single, homogeneous substance. However, it is generally preferred to start with native plant or animal raw materials for their production, resulting in mixtures of substances with varying alkyl chain lengths, depending on the specific raw material.

[0583] For surfactants that represent addition products of ethylene and / or propylene oxide to fatty alcohols or derivatives of these addition products, both products with a "normal" homolog distribution and those with a narrowed homolog distribution can be used. A "normal" homolog distribution refers to mixtures of homologs obtained from the reaction of fatty alcohol and alkylene oxide using alkali metals, alkali metal hydroxides, or alkali metal alkoxides as catalysts. Narrowed homolog distributions, on the other hand, are obtained when, for example, hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides, hydroxides, or alkoxides are used as catalysts. The use of products with a narrowed homolog distribution may be preferable.

[0584] Furthermore, the oxidation dyes according to the invention can contain other active ingredients, excipients and additives, such as P93087WO 11 August 2025

[0585] Viering, Jentschura & Partner mbB non-ionic polymers such as vinylpyrrolidone / vinyl acrylate copolymers, polyvinylpyrrolidone and vinylpyrrolidone / vinyl acetate copolymers and polysiloxanes, cationic polymers such as quaternized cellulose ethers, polysiloxanes with quaternary groups, dimethyl diallylammonium chloride polymers, acrylamide-dimethyl diallylammonium chloride copolymers, dimethylamino ethyl methacrylate-vinylpyrrolidone copolymers quaternized with diethyl sulfate, vinylpyrrolidone-imidazolinium methchloride copolymers and quaternized polyvinyl alcohol, zwitterionic and amphoteric polymers such as acrylamidopropyl trimethylammonium chloride / acrylate copolymers and octylacrylamide / methyl methacrylate / tert-butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymer, anionic polymers such as Polyacrylic acids, cross-linked polyacrylic acids, vinyl acetate / crotonic acid copolymers, vinylpyrrolidone / vinyl acrylate copolymers,Vinyl acetate / butyl maleate / isobornyl acrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and acrylic acid / ethyl acrylate / N-tert. butyl acrylamide terpolymers, bio-based styling agents such as hydrolyzed corn starch (Verdessence Maize from BASF), thickeners such as agar-agar, gellan gum, guar gum, alginates, carrageenans, tara gum, xanthan gum, gum arabic, karaya gum, locust bean gum, linseed gum, dextrans, cellulose derivatives, e.g., methylcellulose, hydroxyalkylcellulose, and carboxymethylcellulose, starch fractions and derivatives such as amylose, amylopectin, and dextrins, clays such as bentonite, or fully synthetic hydrocolloids such as polyvinyl alcohol.

[0586] Structuring agents such as maleic acid and lactic acid, hair-conditioning compounds such as phospholipids, for example soy lecithin, egg lecithin and cephalins,

[0587] Protein hydrolysates, in particular elastin, collagen, keratin, milk protein, soy protein and wheat protein hydrolysates, their condensation products with fatty acids, as well as quaternized protein hydrolysates, perfume oils, dimethyl isosorbide and cyclodextrins,

[0588] Solvents and solvents such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerin and diethylene glycol, fiber structure-improving agents, in particular mono-, di- and oligosaccharides such as glucose, galactose, fructose, fruit sugar and lactose, quaternary amines such as methyl 1-alkylamidoethyl 2-alkylimidazolinium methosulfate, defoamers such as silicones, dyes for coloring the product, P93087WO 11 August 2025

[0589] Viering, Jentschura & Partner mbB

[0590] Anti-dandruff agents such as piroctone olamines, zinc omadine and climbazole, sunscreens, in particular derivatized benzophenones, cinnamic acid derivatives and triazines, exfoliating agents, pH-adjusting substances such as common acids, in particular food acids and bases, active ingredients such as allantoin, pyrrolidone carboxylic acids and their salts as well as bisabolol, vitamins, provitamins and vitamin precursors, in particular those of groups A, B3, B5, B6, C, E, F and H, plant extracts such as extracts of green tea, oak bark, nettle, witch hazel, hops, chamomile, burdock root, horsetail, hawthorn, linden blossom, almond, aloe vera, pine needle, horse chestnut, sandalwood, juniper, coconut, mango, apricot, lime, wheat, kiwi, melon, orange, grapefruit, sage, rosemary, birch, mallow, Meadowfoam, wild thyme, yarrow, thyme, lemon balm, restharrow, coltsfoot, marshmallow, meristem, ginseng and ginger root, cholesterol, enzymes,Thickening agents such as sugar esters, polyol esters or polyol alkyl ethers,

[0591] Fats and waxes such as shea butter, cocoa butter, beeswax, hydrogenated castor oil, carnauba wax, jojoba wax, and paraffins, fatty acid alkanolamides,

[0592] Complexing agents such as EDTA, NTA, β-alanine diacetic acid and phosphonic acids,

[0593] Swelling and penetrating agents such as glycerin, propylene glycol monoethyl ether, carbonates, hydrogen carbonates, guanidines, ureas, as well as primary, secondary and tertiary phosphates, pearlescent agents such as ethylene glycol mono- and distearate and PEG-3 distearate, pigments, stabilizers for hydrogen peroxide and other oxidizing agents,

[0594] Contains propellants such as propane-butane mixtures, isobutane, N2O, dimethyl ether, CO2 and air, and antioxidants.

[0595] Regarding further optional components and the quantities of these components used, explicit reference is made to the relevant handbooks known to those skilled in the art, e.g., Karlheinz Schrader, Andreas Domsch, Cosmetology, Vols. I-III, Verlag für chemische Industrie, H. Ziolkowsky GmbH, Tannhausen. P93087WO August 11, 2025

[0596] Viering, Jentschura & Partner mbB

[0597] The oxidation dyes according to the invention preferably contain the dye precursors in a suitable aqueous, alcoholic, or aqueous-alcoholic carrier. For the purpose of hair coloring, such carriers are, for example, creams, emulsions, gels, or surfactant-containing foaming solutions, such as shampoos, foam aerosols, or other preparations suitable for application to the hair.

[0598] However, it is also conceivable to integrate the dye precursors into a powdered or tablet-shaped formulation.

[0599] For the purposes of the present invention, aqueous-alcoholic solutions are understood to be aqueous solutions containing 3 to 70 wt% of a Ci-C4 alcohol, in particular ethanol or isopropanol. The oxidation dyes according to the invention may additionally contain further organic solvents, such as methoxybutanol, benzyl alcohol, ethanediol, or 1,2-propylene glycol. All water-soluble organic solvents are preferred.

[0600] The actual oxidative dyeing of the fibers can, in principle, be carried out with atmospheric oxygen. However, a chemical oxidizing agent is preferably used, especially when a lightening effect on human hair is desired in addition to the dyeing. Suitable oxidizing agents include persulfates, chlorites, and, in particular, hydrogen peroxide or its adsorption products with urea, melamine, and sodium borate. According to the invention, however, the oxidative dye can also be applied to the hair together with a catalyst that activates the oxidation of the dye precursors, e.g., by atmospheric oxygen.

[0601] Such catalysts include, for example, metal ions, iodides, quinones, or certain enzymes.

[0602] Suitable metal ions include, for example, Zn 2+ , Cu 2+ , Fe 2+ , Fe 3+ , Mn 2+ , Mn 4+ , Li + , Mg 2+ , Ca 2+ and Al 3+ .

[0603] Suitable enzymes include, for example, peroxidases, which can significantly enhance the effect of small amounts of hydrogen peroxide. Furthermore, enzymes that directly oxidize the oxidation dye precursors with the aid of atmospheric oxygen, such as laccases, or that generate small amounts of hydrogen peroxide in situ and thus biocatalytically activate the oxidation of the dye precursors, are also suitable according to the invention. Particularly suitable catalysts for P93087WO 11 August 2025

[0604] Viering, Jentschura & Partner mbB

[0605] Oxidation of the dye precursors is carried out by the so-called 2-electron oxidoreductases in combination with the specific substrates, e.g.

[0606] Pyranose oxidase and, for example, D-glucose or galactose,

[0607] glucose oxidase and D-glucose,

[0608] Glycerol oxidase and glycerol, pyruvate oxidase and methylpyruvic acid or their salts, alcohol oxidase and alcohol (methanol, ethanol),

[0609] Lactate oxidase and lactic acid and their salts,

[0610] Tyrosinase oxidase and tyrosine,

[0611] Uricase and uric acid or their salts,

[0612] Choline oxidase and choline, amino acid oxidase and amino acids. The actual oxidizing dye is expediently prepared immediately before use by mixing the oxidizing agent preparation with the preparation containing the dye precursors. The resulting ready-to-use hair dye preparation should preferably have a pH value in the range of 6 to 12. Application of the hair dye in a weakly alkaline environment is particularly preferred. The application temperatures can range between 15 and 40°C.

[0613] After a processing time of 5 to 45 minutes, the oxidative dye is removed from the hair by rinsing. Rinsing with shampoo is unnecessary if a carrier containing a high concentration of surfactants, such as a coloring shampoo, was used.

[0614] In a fifth aspect, the invention relates to a method for dyeing keratin fibers, in which the oxidation dye according to the invention is applied to the fibers and rinsed off after a reaction time. The reaction time is preferably 5 to 45 minutes.

[0615] The application temperatures for this embodiment can range between 15 and 40°C. After a reaction time of typically 20 to 30 minutes, the hair dye is removed from the hair by rinsing. Rinsing with shampoo is unnecessary if a carrier containing a high concentration of surfactants, such as a coloring shampoo, was used.

[0616] In a sixth aspect, the invention relates to the use of the water-insoluble lignin particles according to the invention as a coupler component in an oxidation dye for dyeing keratinous fibers, in particular human hair. P93087WO August 11, 2025

[0617] Viering, Jentschura & Partner mbB

[0618] Definitions

[0619] The term "keratin-containing fibers" generally refers to all animal hair, e.g., wool, horsehair, angora hair, furs, feathers, and products or textiles made from them. However, keratin fibers are preferably human hair. In the context of this application, the "agent for dyeing keratin fibers" or the "oxidizing agent for dyeing keratin fibers" is also referred to synonymously as "oxidizing dye," and the "agent for treating keratin fibers" is referred to synonymously as "hair treatment agent."

[0620] The term "lignin" refers to a complex polymer composed of aromatic alcohols as monomers, known as monolignols, which are essentially linked together via ether groups. Monolignols include, for example, phenylpropanoids such as p-coumarin alcohol, coniferyl alcohol, and sinapyl alcohol, which may be methoxylated to varying degrees. Lignin is a component of the secondary cell wall of plants and some algae, where it forms cross-linked macromolecules with molecular weights exceeding 5000 u. Different wood and plant species contain lignins with varying percentages of monolignols. For example, lignin from softwood predominantly contains coniferyl units, which have a guaiacyl residue (3-methoxy-4-hydroxyphenyl group), while lignin from hardwood contains varying proportions of guaiacyl residues and sinapyl units, which have a syringyl residue (3,5-methoxy-4-hydroxyphenyl group).Lignin from grasses contains all three units. Based on its isolation from lignified plant parts, it may still contain residual components of cellulose, hemicellulose, pectin, proteins, and sugars. Due to its isolation from lignified plant parts, where it is complexly linked with other biopolymers such as cellulose and hemicellulose, the lignin still contains significant amounts of hemicellulose and cellulose. Therefore, a lignin according to the invention is understood to be a lignin that may contain between 5 and 25 wt% hemicellulose and cellulose. The lignin content is between 75 and 95 wt%.

[0621] According to the invention, "powder" is the general term for a form of fragmentation of dry solids obtained by comminution, i.e., grinding or crushing in a mortar (pulverizing), milling, or as a result of atomization or freeze-drying. A particularly fine fragmentation is often called atomization or micronization. Powders can behave quite differently physically: in the form of dust or smoke, they resemble P93087WO 11 August 2025

[0622] Viering, Jentschura & Partner mbB

[0623] Powders resemble liquids in their behavior when exposed to gases, in their flow behavior (sand), during pneumatic transport in pipelines, or when bubbling in fluidized beds, and very densely packed powders can exhibit properties of solids (tablets, powder metallurgy products, coal briquettes, etc.). Based on particle size, powders are commonly classified into coarse powders, fine powders, and ultrafine powders; a more precise classification of powdered bulk materials is achieved through their bulk density and sieve analysis. Methods also exist for determining the powder surface area, such as the BET method. The bulk density of powders is determined according to DIN ISO 697: 1984-01 to check their uniformity. Agglomerates are clumps of primary particles, aggregates, or a mixture of both, whose cohesion is so low that they can be broken down using standard methods for manufacturing coatings or printing inks.They are connected to each other in a bridge-like fashion via edges and corners. Their surface area does not differ significantly from the sum of the surface areas of all the particles that make them up (DIN 53206-1: 1972-08). Agglomerates of pigments and fillers form primarily during drying in the course of pigment or filler production.

[0624] A granular aggregate (granulate) is an asymmetrical aggregate of powder particles (whole crystals, crystal fragments, or active ingredient particles). Unlike a pellet, but similar to an agglomerate, it does not exhibit a harmonious geometric shape; the form of a sphere, rod, cylinder, etc., is only approximate and indicative. The surface is usually uneven and jagged, and the mass is often more or less porous. Granulation refers to the conversion of powder particles into granules, which is important, for example, for the packaging of dosage forms in the pharmaceutical, fertilizer, plastics, and detergent industries. Technical applications frequently utilize fluidized bed processes—often referred to today as prills.The determination of the bulk density according to DIN-ISO 697: 1984-01 and the determination of the angle of repose according to DIN ISO 4324: 1983-12 can be used as criteria for the utility value of granules.

[0625] Spray-dried particles also do not have a regular shape. They can contain voids and exhibit a certain degree of surface roughness. This makes them non-ideal bulk materials.

[0626] This application, in aspects 1 to 3, relates to a means for the treatment of keratinous fibers or its use and a process in which the means is used for P93087WO 11 August 2025

[0627] Viering, Jentschura & Partner mbB

[0628] The application is relevant. In aspects 4 to 6, the application relates to an oxidation dye or a process for dyeing using the oxidation dye and the use of water-insoluble lignin particles. If there are any contradictions between the description concerning aspects 1 to 3 and the description concerning aspects 4 to 6, the contradictory statements refer to the nearest aspect. In other words, the statement "Substance X is Y", made within the description of the first aspect, and "Substance X is Z", made within the description of the fourth aspect, would not constitute a contradiction, since the first statement refers to the subject matter of the first aspect and the second statement refers to the subject matter of the fourth aspect.

[0629] Unless explicitly stated otherwise, numerical values ​​given without decimal places refer to the whole value; those given with one decimal place refer to the whole value. For example, 99% means 99.0%.

[0630] The mention of a document in this document does not constitute an admission that said document or its contents are part of the general knowledge of a person skilled in the art.

[0631] Each feature of the invention that is to be present in a particular area or in a particular quantity can be combined in a corresponding embodiment with the other features of that embodiment, wherein the other features can be present in the areas or quantities disclosed herein for said other features.

[0632] All ranges and quantities for a feature of an embodiment can be combined with all ranges and quantities of the other features in that embodiment. Thus, ranges or values ​​that are specified as preferred, more preferred, or most preferred for a feature or component of the invention can be combined with any range or quantity specified for another feature or component of the embodiment, regardless of whether the range or quantity specified for the other element is designated as preferred, more preferred, or most preferred, etc., or is disclosed without such a designation or indication.

[0633] It should be expressly noted that, within the scope of the present patent application, indefinite articles and numerical indications such as "one", "two", etc., are generally to be understood as "at least" indications, i.e., as "at least one...", P93087WO 11 August 2025

[0634] Viering, Jentschura & Partner mbB

[0635] "at least two..." etc., unless it is expressly clear from the context or it is obvious or technically necessary for a person skilled in the art that only "exactly one...", "exactly two..." etc. can be meant.

[0636] The term "comprise," as used herein, is synonymous with "contains" and does not exclude additional, unlisted elements or process steps. According to the present invention, the term "comprise" also includes the terms "essentially consist of" or "consist of," i.e., that "comprise" can be replaced by the other terms in alternative embodiments, wherein "consist of" excludes any element or step not expressly mentioned, and "essentially consist of" allows the inclusion of additional, unmentioned elements or steps that do not substantially affect the essential or fundamental features of the composition or process in question.

[0637] Where a range of numbers is specified herein, that range is continuous and includes both the minimum and maximum values ​​of the range, as well as every value between those minimum and maximum values. Where a range refers to integers, every integer between the minimum and maximum values ​​of such range is included. Where multiple ranges are specified to describe a feature or characteristic, these ranges may be combined. This means that, unless expressly stated otherwise, all ranges disclosed herein are to be understood as including all subranges contained therein. For example, a specified range of "1 to 10" is to be understood as including all subranges between the minimum value of 1 and the maximum value of 10, including the values ​​1 and 10. Examples of subranges of the range 1 to 10 include 1 to 6.1, 3.5 to 7.8, and 5.5 to 10.The disclosed upper and lower limits for quantity, range, and ratio can be combined independently of each other.

[0638] Further advantages, special features and expedient further developments of the invention will become apparent from the dependent claims and the following presentation of preferred embodiments with reference to the illustrations.

[0639] The embodiments shown here are merely examples of the present invention and should therefore not be interpreted as limiting. Alternative embodiments considered by a person skilled in the art are likewise covered by the scope of protection of the present invention. P93087WO August 11, 2025

[0640] Viering, Jentschura & Partner mbB

[0641] Figures

[0642] Fig. 1 shows a scanning electron microscope image of an unstained single hair at 800x magnification (bar = 100 pm).

[0643] Fig. 2 shows in A to D scanning electron micrographs of individual hairs that were dyed with the vegan hair color “Sienna TW warm red” according to embodiment 1, also at 800x magnification (bar = 100 pm).

[0644] Fig. 3 shows in A to D scanning electron micrographs of individual hairs that were dyed with the vegan hair color “Garnet TN Mahogany red” according to embodiment 2, also at 800x magnification (bar = 100 pm).

[0645] Fig. 4 shows the elemental composition based on the results of the EDX analysis for untreated hair (K11 B0), hair dyed with Colorona Sienna (K11 BS) and hair dyed with SynCrystal Garnet (K11 BG).

[0646] Fig. 5 shows in A a scanning electron micrograph of a single hair that was colored with Schwarzkopf Brillance Intensive Red 872 and in B a scanning electron micrograph of a single hair that was colored with the permanent hair color “Copper” according to embodiment 1, at A at 800x magnification (bar = 100 pm) and at B at 2000x magnification (bar = 30 pm).

[0647] Fig. 6 shows the elemental composition based on the results of the EDX analysis for untreated hair (K11 B0), hair colored with Schwarzkopf Brillance Intensive Red 872 (K11 B8) and hair colored according to the invention as per Example 1 (K11 BW).

[0648] Examples of implementation

[0649] 1 ■ Vegan powder hair color Sienna TW warm red P93087WO August 11, 2025

[0650] Viering, Jentschura & Partner mbB

[0651] The individual ingredients are combined in a porcelain mortar and briefly ground until homogeneous, resulting in a homogeneous, mix-stable red powder. It can be quickly and easily applied and distributed onto the hair with a brush, rapidly absorbing the hair surface and forming an even red color on blonde or dark brown European, straight hair. This color can be fixed with a few sprays of conventional hairspray and is completely removed from the hair with a regular shampoo.

[0652] The hair dyed using the present method was analyzed as follows: a) Scanning electron microscopy

[0653] For this purpose, dyed blonde individual hairs were coated with gold vapor and examined in a Hitachi TM 3000 Tabletop SEM scanning electron microscope at 800x magnification. Photographic images of the treated hair are shown in Figures 2A to 2D, where the black bar indicates a size of 100 pm. The different types of pigments can be seen as planar structures of varying sizes (from a few pm to approximately 25 pm) that are bound to the hair surface. Figure 1 shows the SEM image of an untreated blonde individual hair. It has a particle-free surface, and due to the lack of hairspray fixation, the cuticle is also visible as a scaly surface structure. b) Energy-dispersive X-ray spectroscopy (EDX)

[0654] The dyed individual hairs were analyzed for their elemental composition using EDX at selected locations and the Quantax 70 software. The results are shown in the table in Figure 4. Compared to the untreated hair (K11 B0), the temporary dyeing with the pigment Colorona Sienna (sample K11 BS) clearly shows that inorganic elements (metals and silicon) are now also present, originating from talc and the color pigments. Furthermore, a significant increase in oxygen is observed in the dyed samples. This oxygen originates from the inorganic oxides and silicates, as well as from lignin, which has a high oxygen content due to the hydroxyl, methoxy, and oxymethylene groups and ether bridges it contains.

[0655] 2. Vegan Powder Hair Color Garnet TN Mahogany Red P93087WO August 11, 2025

[0656] Viering, Jentschura & Partner mbB

[0657] The individual ingredients are combined in a porcelain mortar and briefly ground until homogeneous, resulting in a homogeneous, stable, mahogany-red powder. It can be quickly and easily applied and distributed with a brush, rapidly absorbing into the hair surface and forming an even mahogany-red color on blonde or dark brown European, straight hair. This color can be fixed with a few sprays of conventional hairspray and is completely removed from the hair with a regular shampoo.

[0658] The hair stained using the present method was analyzed as follows: a) Scanning electron microscopy

[0659] For this purpose, dyed blonde individual hairs were coated with gold vapor and examined in a Hitachi TM 3000 tabletop scanning electron microscope (SEM) at 800x magnification. Photographic images of the treated hair are shown in Figures 3A to 3D, where the black bar indicates a size of 100 pm. The different types of pigments can be seen as planar structures of varying sizes (from a few pm to approximately 25 pm) bound to the hair surface. b) Energy-dispersive X-ray spectroscopy (EDX)

[0660] The dyed individual hairs were analyzed for their elemental composition using EDX at selected locations and the Quantax 70 program. The results are shown in the table in Figure 4. Compared to the untreated hair (K11 B0), the temporary dyeing with the pigment SynCrystal Garnet (sample K11 BG) clearly shows that it now also contains inorganic elements (metals and silicon), which are present in talc and the color pigments P93087WO. August 11, 2025

[0661] Viering, Jentschura & Partner mbB. Furthermore, a significant increase in oxygen content is observed in the stained samples. This originates partly from the inorganic oxides and silicates and partly from lignin, which has a high oxygen content due to the hydroxy, methoxy, and oxymethylene groups and ether bridges it contains.

[0662] The individual ingredients are combined in a porcelain mortar and briefly ground until homogeneous, forming a homogeneous, stable yellow powder. It can be quickly and easily applied and distributed onto the hair with a brush, rapidly absorbing the hair surface and creating an even yellow color on dark brown, straight European hair. This color can be fixed with a few sprays of conventional hairspray and is completely removed from the hair with a regular shampoo.

[0663] 4. Vegan Root Concealer Powder Brown TC P93087WO August 11, 2025

[0664] Viering, Jentschura & Partner mbB

[0665] The individual ingredients are combined in a porcelain mortar and briefly ground until homogeneous, forming a homogeneous, mix-stable, medium-brown powder. It can be quickly and easily applied and distributed with a brush, rapidly absorbing the hair surface and creating an even, medium-brown color on gray or blonde, straight European hair. The root color provides complete gray coverage. This color can be fixed with a few sprays of conventional hairspray and is completely removed by regular shampooing. For the "Dark Brown" variant, the "SynCrystal Soft Autumn Gold" component is omitted.

[0666] 5. Braun TC Root Concealer Pump Spray

[0667] The hair color according to Example 4 is mixed with pentylene glycol, ethanol, and dicaprylyl carbonate and filled into a spray bottle. This creates a dark brown suspension. The bottle is shaken before use. The root concealer pump spray is then applied by spraying it onto the gray roots or a blonde hair strand (heavily bleached blonde hair strands (Kerling International Haarfabrik GmbH, Backnang, Germany, Remis, Color 11 light blonde bleached, free hair length 15 cm)). P93087WO August 11, 2025

[0668] Viering, Jentschura & Partner mbB

[0669] The root-covering pump spray is quickly absorbed into the hair surface, creating an even, medium-brown color on gray or blonde, straight European hair. The root color provides complete gray coverage. This color can be fixed with a few sprays of regular hairspray and is completely removed by shampooing.

[0670] 6. Permanent hair color “Copper”

[0671] The individual ingredients are mixed homogeneously and, as a hair color, result in a reddish-brown, thick mass that is applied to the hair and rinsed out after a reaction time of 30 minutes.

[0672] On heavily bleached blonde hair strands (Kerling International Haarfabrik GmbH, Backnang, Germany, Remis, color 11 light blonde bleached, hair length 15 cm), a change in the red coloration is achieved compared to the original 872. The lignin pigment results in a slight lightening of the hair towards a copper color. With a dilution containing only 20 g of pentane-1,2-diol as an additional ingredient instead of lignin, the coloration is less intense than with the original commercially available color. Hair strands treated with LignoBase Warm WS25 are also easier to comb without conditioner than those colored with 872 alone. One explanation for this is the film formed by the lignin on the hair strand.

[0673] 7. Permanent hair color “light red”

[0674] The individual ingredients are mixed homogeneously to create a thick, reddish-brown hair dye, which is applied to the hair and rinsed out after a processing time of 30 minutes. P93087WO August 11, 2025

[0675] Viering, Jentschura & Partner mbB

[0676] On heavily bleached blonde hair strands (Kerling International Haarfabrik GmbH, Backnang, Germany, Remis, color 11 light blonde bleached, free hair length 15 cm), a change in the red coloration is achieved compared to the original 872. The result is a coloration of the hair by the lignin pigment in the form of a slight lightening in a red variant.

[0677] The ingredients (INCI) of the color cream and developer lotion of Schwarzkopf Brillance Intense Red 872 are as follows:

[0678] Colorcreme: Aqua (Water), Cetearyl Alcohol, Ammonium Hydroxide, Coconut Alcohol, Sodium Laureth Sulfate, Isostearic Acid, 4-Amino-m-Cresol, Sodium Lauryl Glucose Carboxylate, Dimethicone, Bis-Diisopropanolamino-PG-Propyl Dimethicone / Bis-Isobutyl PEG-14 Copolymer, Potassium Hydroxide, 2-Amino-3-Hydroxypyridine, Lauryl Glucoside, 4-Amino-2-Hydroxytoluene, Myristic Acid, Toluene-2,5-Diamine Sulfate, Ceteareth-20, Sodium Sulfite, Parfum (Fragrance), Ceteareth-12, Sodium Chloride, Prunus Armeniaca (Apricot) Kernel Oil, 1-Hydroxyethyl 4,5-Diamino Pyrazole Sulfate, Sodium Silicate, Citric Acid, Etidronic Acid, Ammonium Sulfate, Butyloctanol, Polysorbate 20, Linalool, Ascorbic Acid, Citronellol, Sorbic Acid, Lactic Acid, Sodium Benzoate, Benzyl Alcohol|

[0679] Entwicklerlotion: Aqua (Water), Hydrogen Peroxide, Cetearyl Alcohol, PEG-40 Castor Oil, Disodium Pyrophosphate, Sodium Cetearyl Sulfate, Disodium EDTA, Sodium Benzoate, Phosphoric Acid

[0680] The hair stained using the present method was analyzed as follows: a) Scanning electron microscopy

[0681] For this purpose, dyed individual hairs were coated with gold vapor and examined using a Hitachi TM 3000 Tabletop SEM scanning electron microscope at magnifications of 800x and 2000x. Photographic images of the treated hair are shown in Figures 2A (800x) and 2B (2000x), where the black bar in Figure A at 800x magnification indicates a size of 100 pm and the black bar in Figure B at 2000x magnification indicates a size of 30 pm. Particularly at 2000x magnification in Figure 2B, small white dots of lignin, which are oxidatively bound to the hair surface by the dyeing process, are visible. Inclusions are also visible below the cuticle. P93087WO August 11, 2025

[0682] Viering, Jentschura & Partner mbB

[0683] Figure 1 shows the SEM image of an untreated single hair. It has a particle-free surface, and due to the lack of hair fixation, the cuticle is also visible as a scaly surface structure. b) Energy-dispersive X-ray spectroscopy (EDX)

[0684] The dyed individual hairs were analyzed for their elemental composition using EDX at selected locations and the Quantax 70 program. The results are shown in the table in Figure 3 and are as follows:

[0685] Lignin contains hydroxy, methoxy, and oxymethylene groups, as well as ether bridges, resulting in a higher oxygen content in dyed hair compared to hair dyed with the original Schwarzkopf Brillance 872. Therefore, the carbon-to-oxygen ratio (C / O) is lower when lignin is used as an additional coupling component compared to the original dye and undyed hair. The nitrogen content is highest in undyed hair, and the nitrogen-to-carbon ratio is also highest, as this is where amino acids (keratin) are most prevalent. When hair is dyed with lignin, the nitrogen content is significantly higher compared to the original dye. Thus, there are clear differences between the two dyes, which are also reflected in the different shades.

[0686] 6. Determination of particle size

[0687] The particle size distribution and mean size of the powders were analyzed using a laser diffraction particle size analyzer equipped with a Tornado dry powder system (LS 13320, Beckman Coulter, USA). Fraunhofer theory was used to determine the diameters and size distributions. The particle size measurements are presented as the size distribution, and the mean diameter (D50) is also reported.

[0688] 7. Determination of the proportion of C5 and C6 sugars

[0689] Standard methods for determining C5 and C6 sugars, such as xylose, glucose, mannose, galactose, and arabinose, are familiar to those skilled in the art. These can be quantitatively determined using HPAEC borate (High Performance Anion Exchange Chromatography). Equipment: Dionex Ultimate 3000, Variable Wavelength Detector, Pump HPG-3200A, Pump HPG-3100A, Autosampler, Degasser, Analysis software: Dionex Chromeeon Version 6.80, Stationary phase: Strong anion exchange resin MCI Gel CA08F (Mitsubishi Chemical), packed in an Omnifit empty column 5 x 120 mm (65°C). Mobile P93087WO August 11, 2025

[0690] Viering, Jentschura & Partner mbB

[0691] Phase: Potassium tetraborate buffer (potassium tetraborate / boric acid) 0.7 ml / min gradient elution with A: 0.3 M borate buffer (pH 8.6) B: 0.9 M borate buffer (pH 9.5) and the following elution schedule: 0 min: 90% A, 10% B (0-35 linear gradient); 35 min: 10% A, 90% B; 43 min: 10% A, 90% B (43-49.99 linear gradient); 49.99 min: 90% A, 10% B; 50 min: restart. Post-column derivatization by adding cubicinchoninate solution (bicinquinic acid, sodium carbonate, aspartic acid, and copper sulfate pentahydrate) 0.35 ml / min. Heating to 105°C in a 30m long Teflon coil (0.3 mm iD). Detection is carried out at 560 nm in a UV detector.

[0692] 8. Determination of bulk density and tap density

[0693] The bulk density of the lignin particle powder was measured by placing a specific quantity of lignin powder, which should gradually settle by gravity (without the influence of other forces), into a calibrated cylinder and weighing the powder occupying a specific volume. The tapped density was measured using a tapped density assessor (Copley Scientific Ltd.), specifically the volume a known quantity of powder occupies after tapping when the volume no longer changes (at least 1250 taps).

[0694] 9. Determination of shear stress

[0695] Those skilled in the art are familiar with standard methods for determining shear stress.

[0696] 10. Determination of the contact friction angle

[0697] Standard procedures for determining the contact friction angle are known to those skilled in the art.

[0698] 11. Measurement of flow behavior using the Carr index

[0699] The Carr index was derived from the bulk density and knock density data according to the following equation: 100

[0700] The Carr index provides an indication of the flow properties of the lignin powder; a value >25% indicates good flow properties, while <25% suggests a cohesive powder with poor flow properties. P93087WO August 11, 2025

[0701] Viering, Jentschura & Partner mbB

[0702] 12. Measurement of flow behavior using the Hausner ratio

[0703] The Hausner ratio is also used as an indicator of flowability, with a value of less than 1.20 indicating good flowability, while a value greater than 1.30 indicates poor flowability. The Hausner ratio was calculated using the following equation:

[0704] Bulk density Hausner ratio = — ■ — — — ■ — Knock density

[0705] 13. Measurement of flow behavior using the flowability factor ffc

[0706] Flowability and cohesion were measured using a Jenike shear tester; a detailed description of the methodology can be found in Jaeda et al. 2009 (Master's Thesis, Heinrich Heine University Düsseldorf: "The use of a ring shear tester to evaluate the flowability of pharmaceutical bulk solids"). The ratio ffc (flowability factor) between the consolidation stress Oi and the unrestricted yield strength o c is used for the numerical measurement of flowability; ffc is calculated using the following equation:

[0707] Flowability and cohesion are classified as follows according to Jenike: ffc < 1 - non-flowing, 1 < ffc < 2 - very cohesive, 2 < ffc < 4 - cohesive, 4 < ffc < 10 - slightly flowing, 10 < ffc - free flowing.

[0708] 14. Measuring the moisture content

[0709] The moisture content of the powdered lignin was measured gravimetrically using a moisture meter (Precisa Gravimetrics AG, Switzerland). In short, 1 g of powder was placed on an aluminum plate and heated to 105 °C with a halogen lamp. The mass loss was recorded until it fell below 1 wt% within 120 s or a maximum of 5 minutes.

[0710] 15. Measurement of the specific surface area (SSO)

[0711] The specific BET surface area was measured according to the BET method in accordance with ISO 9277:2010 using nitrogen after the sample had been exposed to 250 P93087WO for 30 minutes on August 11, 2025.

[0712] Viering, Jentschura & Partner mbB

[0713] The sample had been heated to °C. Before these measurements, the sample was filtered, rinsed, and dried in an oven at 110 °C for at least 12 hours.

[0714] 16. Viscosity Measurement

[0715] To measure the viscosity, a 10 wt% suspension of the lignin particles in water was prepared and measured using the rotational viscometer “ROTASVISC me-vi” (IKA -Werke GmbH & Co. KG, Staufen, Germany) with the standard spindle SP-7 at 100 rpm.

[0716] Types of embodiment:

[0717] 1. Agents for the treatment of keratinous fibers, especially human hair, comprising:

[0718] (a) Lignin in the form of water-insoluble lignin particles having a mean particle size D50 of 100 nm to 100 pm, preferably of 5 to 30 pm and particularly preferably of 10 to 15 pm; and

[0719] (b) at least one particle-shaped carrier material that is solid under normal conditions or at least one liquid or semi-solid carrier material.

[0720] 2. Composition according to embodiment 1, characterized in that the lignin particles consist of lignin with a proportion of 75 to 95 wt.% and cellulose and hemicellulose with a proportion of 5 to 25 wt.%.

[0721] 3. Composition according to embodiment 1 or 2, characterized in that the lignin particles have one or more of the following properties: a. A proportion of C5 and C6 monosaccharides of less than 10 wt.%; b. A bulk density of 425 to 500 kg / m³ 3 c. A density of 500 to 550 kg / m³ 3 d. A shear stress of 100 to 250 Pa; e. A contact friction angle of 30.0° to 35.0°, preferably 30.5° to 32.5°; f. A Carr index of 13.0 to 19.5; g. A flow index ff c from 5.0 to 18.0; h. A moisture content of less than 5 wt% and preferably less than 3.5 wt%; i. A specific surface area (BET) of 0.5 to 100 m² 2 / g, preferably from 0.5 to 50 m 2 / g, especially preferably from 0.5 to 35 m 2 / g and especially preferably from 0.5 to 10 m 2 / g, determined according to DIN 66131 (with nitrogen); P93087WO 11 August 2025

[0722] Viering, Jentschura & Partner mbB j. A pH value of 3 to 7, measured in a 10% aqueous suspension; k. A viscosity of less than 100 mPas, measured in a 10% aqueous suspension.

[0723] 4. A composition according to one of embodiments 1 to 3, characterized in that the lignin is a deodorized lignin and / or has been enzymatically pretreated with cellulase.

[0724] 5. A composition according to one of the preceding embodiments, characterized in that the lignin is a water-soluble or water-insoluble lignin, preferably selected from the group consisting of natural lignin, Klason lignin, hydrolyzed lignin, Kraft lignin, ground wood lignin, soda lignin, organosolv lignin, aquasolv lignin, colloidal lignin and mixtures thereof, wherein the lignin is particularly preferably an aquasolv lignin or soda lignin.

[0725] 6. Composition according to one of the preceding embodiments, characterized in that the lignin particles are contained in a weight fraction of 0.1 to 99.9 wt.%, preferably 2 to 80 wt.%, particularly preferably 5 to 70 wt.%, and especially preferably 10 to 65 wt.%, in each case based on the total weight of the ready-to-use composition.

[0726] 7. Means according to one of the preceding embodiments, characterized in that the at least one particle-shaped carrier material, which is solid under normal conditions, has a particle size of 5 nm to 100 pm.

[0727] 8. A composition according to one of the preceding embodiments, characterized in that the at least one solid, particulate carrier material is selected from the group consisting of optionally modified starches and starch derivatives, cellulose and cellulose derivatives, silicon dioxide, amorphous silicas, talc, kaolin, mica, nepheline, perlite, phlogopite, synthetic fluorophlogopite, clays, in particular bentonites, magnesium aluminum silicates, boron nitride, lactoglobulin derivatives, organic polymer powders, in particular polyolefins, polycarbonates, polyurethanes, polylactides, polyhydroxybutyrates, polyamides, or silicones, as well as mixtures of these substances, wherein the carrier material preferably consists of talc, hydrophobically modified starch or starch, or combinations thereof.

[0728] 9. Means according to one of the preceding embodiments, characterized in that the at least one is solid under normal conditions, P93087WO 11 August 2025

[0729] Viering, Jentschura & Partner mbB contains particulate, inert carrier material in a weight fraction of 0.1 to 99.9 wt.%, preferably 20 to 98 wt.%, particularly preferably 30 to 95 wt.%, and especially preferably 35 to 90 wt.%, in each case based on the total weight of the ready-to-use agent.

[0730] 10. A composition according to one of the preceding embodiments, characterized in that the composition additionally contains an active ingredient, excipient, or additive selected from the group consisting of absorbents, antimicrobial substances such as fungicides or bactericidal agents; antioxidants; antiperspirants, antifoaming agents; anti-dandruff agents; antistatic agents; binders; chelating agents, co-emulsifiers; deodorizing agents; emollients; emulsifiers; emulsion stabilizers; enzymes; humectants; film formers; preservatives; corrosion inhibitors; solvents; pH regulators; reducing agents; thickening agents; surfactants; hair-conditioning compounds such as cetrimonium chloride, esterquats, alkylmethicones, and amodimethicones; fiber-improving agents; protein hydrolysates of animal and / or plant origin; and plant extracts. Concentrated consistency enhancers such as sugar esters, polyol esters and polyol alkyl ethers;Clay minerals modified with quaternary ammonium compounds; fats and oils; swelling and penetration agents; pearlescent agents such as ethylene glycol mono- and distearate as well as PEG-3 distearate; stabilizers; styling polymers; rheological additives; natural and / or synthetic waxes; cosmetic active ingredients such as panthenol, pantolactone and niacinamide; odor complexing agents; water repellents; fragrances; and UV protection substances, and combinations thereof.

[0731] 11. A composition according to one of the preceding embodiments, characterized in that the composition is a leave-in product preferably selected from the group consisting of hairspray, hair conditioner, hair rinse, hairspray, hair treatment, hair tonic, hair stick, heat protectant spray, styling powder, hair fibers, root concealer spray, concealing mascara, mascara, instant volumizing powder, color powder, pressed color powder, eyebrow pencils, gel, mascara and powder and brow filler, products for taming baby hair and for scalp and beard care; hair glow, styling balm, curl cream, hair mousse, hair gel, texture clay, gel wax, pomade, 2-in-1 beard and hair pomade, hair styling cream, hair wax, hair mask, 4-in-1 hair mask, hair oil, P93087WO August 11, 2025

[0732] Viering, Jentschura & Partner mbB

[0733] Hair butter, scalp care products in the sense of skinification of hair care, salon hair care and leave-on conditioner.

[0734] 12. A composition for the temporary coloring of keratinous fibers, in particular human hair, according to one of the preceding embodiments, characterized in that the composition preferably additionally contains at least one color pigment selected from natural pigments, organic pigments, inorganic pigments, colored metal oxides, metal hydroxides, metal oxide hydrates, silicates, metal sulfides, complex metal cyanides, metal sulfates, bronze pigments and / or from colored pigments based on silica, mica or mica, coated with at least one metal oxide and / or a metal oxychloride, as well as colored pigments based on mica and coated with silica, titanium dioxide and, in accordance with Dryflux technology, additionally with carbon, and Color Travel pigments based on mica, coated with metal oxides and carbon.

[0735] 13. A composition for temporarily coloring keratinous fibers, in particular human hair, according to embodiment 12, characterized in that it contains as a color pigment at least one colored pigment based on fluorphlogopite, silica, mica or mica, which is coated with one or more metal oxides from the group consisting of titanium dioxide (CI 77891), black iron oxide (CI 77499), yellow iron oxide (CI 77492), red and / or brown iron oxide (CI 77491, CI 77499), manganese violet (CI 77742), ultramarine (sodium aluminum sulfosilicates, CI 77007, Pigment Blue 29), chromium oxide hydrate (CI 77289), chromium oxide (CI 77288), tin oxide (CI 77861) and / or iron blue (ferric ferrocyanide, CI 77510) as well as colored Pigments based on mica and coated with silica, titanium dioxide (CI 77891) and, according to Dryflux technology, additionally with carbon, and Color Travel pigments based on mica, coated with titanium dioxide (CI 77891), silica,are coated with carbon and tin oxide as well as carbon black (CI 77266).

[0736] 14. A means for temporarily dyeing keratinous fibers, in particular human hair, according to embodiment 12, characterized in that the color pigment is a natural pigment selected from the group consisting of red henna, neutral henna, black henna, chamomile flower, sandalwood, black tea, green tea, buckthorn bark, sage, logwood, madder root, catechu, sedre, alkanet root, turmeric root, walnut shell, walnut leaves, senna leaves, indigo and / or cochineal. P93087WO August 11, 2025

[0737] Viering, Jentschura & Partner mbB

[0738] 15. Means for temporarily coloring keratinous fibers, in particular human hair, according to embodiment 12, characterized in that the color pigment is an organic pigment selected from the group consisting of insoluble organic dyes or color lakes, which are preferably selected from the group of nitroso, nitro, azo, xanthene, anthraquinone, isoindolinone, isoindolin, quinacridone, perinone, perylene, phthalocyanine, diketopyrrolopyrrole, indigo, thioindigo, dioxazine, and / or triarylmethane compounds.

[0739] 16. Composition according to one of the embodiments 12 to 15, characterized in that the color pigment is contained in a weight fraction of 0.1 to 60.0 wt.%, preferably of 1.0 to 50.0 wt.%, particularly preferably of 5.0 to 43 wt.%, and especially preferably of 10 to 35 wt.%, in each case based on the total weight of the ready-to-use composition.

[0740] 17. A composition according to one of the preceding embodiments, characterized in that the composition is available in one of the following formulations: powder, aqueous solution, alcoholic solution, oil, gel, foaming gel, lotion, cream, hair butter, spray, aerosol, pressed powder, stick, suspension, pump foam, hair mascara, eyelash mask and hair mask.

[0741] 18. Use of an agent according to any embodiment 12 to 17 as a temporary dye for human hair for intensive coloring, improvement of grey coverage, equalization, color intensity and / or durability of the dyes.

[0742] 19. Use according to embodiment 18, characterized in that the agent is a color powder, a color fixative, a color blow-dry lotion, a color blow-dry foam, a color rinse, a color gel or a color cream.

[0743] 20. Method for temporarily coloring and changing the shape of hair, wherein a means according to one of embodiments 11 to 17, which is formulated as a powder, pressed powder, leave-in hair mask, hair butter, hair mascara, hair oil, styling cream, pump spray or aerosol spray, is applied or sprayed onto dry hair and the hair is styled before or during application.

[0744] 21. Oxidative dye for dyeing keratinous fibers, especially human hair, containing coupler components and developer components in a cosmetically acceptable carrier, wherein at least one lignin is the coupler component. P93087WO 11 August 2025

[0745] Viering, Jentschura & Partner mbB contains in the form of water-insoluble lignin particles, which have a mean particle size D50 of 100 nm to 100 pm.

[0746] 22. Oxidation dye according to embodiment 21, characterized in that the lignin particles consist of lignin with a proportion of 75 to 95 wt.% and cellulose and hemicellulose with a proportion of 5 to 25 wt.%.

[0747] 23. Oxidation dye according to embodiment 21 or 22, characterized in that the lignin particles have one or more of the following properties: a. A mean particle size D50 of 5 to 30 pm and preferably of 10 to 15 pm; b. A proportion of C5 and C6 monosaccharides of less than 10 wt.%; c. A bulk density of 425 to 500 kg / m³ 3 ; d. A density at knockdown of 500 to 550 kg / m³ 3 e. A shear stress of 100 to 250 Pa; f. A contact friction angle of 30.0° to 35.0°, preferably 30.5° to 32.5°; g. A Carr index of 13.0 to 19.5; h. A flow index ff cfrom 5.0 to 18.0; i. A moisture content of less than 5 wt% and preferably less than 3.5 wt%; j. A specific surface area (BET) of 0.5 to 100 m² 2 / g, preferably from 0.5 to 50 m 2 / g, especially preferably from 0.5 to 35 m 2 / g and especially preferably from 0.5 to 10 m 2 / g, determined according to DIN 66131 (with nitrogen); k. A pH value of 3 to 7, measured in a 10% aqueous suspension; l. A viscosity of less than 100 mPas, measured in a 10% aqueous suspension.

[0748] 24. Oxidation dye according to one of embodiments 21 to 23, characterized in that the lignin is a GS lignin or an HGS lignin, wherein it is preferably isolated from hardwood, grasses or monocotyledonous plants.

[0749] 25. Oxidation dye according to one of embodiments 21 to 24, characterized in that the lignin is a deodorized lignin and / or has been enzymatically pretreated with cellulase.

[0750] 26. Oxidation dye according to one of embodiments 21 to 25, characterized in that the lignin is a water-soluble or water-insoluble lignin, preferably selected from the group consisting of natural lignin, Klason- P93087WO 11 August 2025

[0751] Viering, Jentschura & Partner mbB

[0752] Lignin, hydrolyzed lignin, Kraft lignin, ground wood lignin, soda lignin, organosolv lignin, aquasolv lignin, colloidal lignin and mixtures thereof, wherein the lignin is particularly preferably an aquasolv lignin or ada lignin.

[0753] 27. Oxidation dye according to one of the embodiments 21 to 26, characterized in that the lignin particles are contained in a weight fraction of 0.1 to 99.9 wt.%, preferably of 2 to 70 wt.%, particularly preferably of 5 to 50 wt.%, and particularly preferably of 10 to 35 wt.%, in each case based on the total weight of the ready-to-use agent.

[0754] 28. Oxidation dye according to one of embodiments 21 to 27, characterized in that the developer component is selected from the group consisting of primary aromatic amines with a further free or substituted hydroxy or amino group located in the para- or ortho- position; diaminopyridine derivatives; heterocyclic hydrazones; 4-aminopyrazole derivatives; and 2,4,5,6-tetraaminopyrimidine and its derivatives.

[0755] 29. Oxidation dye according to one of embodiments 21 to 28, characterized in that it contains at least one further coupler component, which is preferably selected from the group consisting of m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenol derivatives.

[0756] 30. Oxidation dye according to embodiment 29, characterized in that the at least one further coupler component is selected from the group consisting of 1-naphthol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 1-phenyl-3-methyl-pyrazolone-5, 2,4-dichloro-3-aminophenol, 1,3-bis-(2',4'-diaminophenoxy)-propane, 2-chlororesorcinol, 4-chlororesorcinol, 2-chloro-6-methyl-3-aminophenol, 2-amino-3-hydroxypyridine, 2-methylresorcinol, 5-methylresorcinol and 2-methyl-4-chloro-5-aminophenol.

[0757] 31. Oxidation dye according to one of embodiments 21 to 30, characterized in that it further contains at least one direct dye.

[0758] 32. Oxidation dye according to embodiment 31, characterized in that the direct dye is cationic.

[0759] 33. Oxidation dye according to one of embodiments 21 to 33, characterized in that it further contains at least one surfactant, preferably P93087WO 11 August 2025

[0760] Viering, Jentschura & Partner mbB selected from the group consisting of anionic, zwitterionic, ampholytic, nonionic and cationic surfactants.

[0761] 34. Method for dyeing keratinous fibers, in which the agent according to one of embodiments 21 to 33 is applied to the fibers and rinsed off after an exposure time.

[0762] 35. Use of water-insoluble lignin particles according to one of embodiments 21 to 26 as a coupler component in an oxidation dye for dyeing keratinous fibers, in particular human hair.

Claims

1. P93087WO August 11, 2025 Viering, Jentschura & Partner mbB Patent claims 1. Agents for the treatment of keratinous fibers, especially human hair, comprising: (a) Lignin in the form of water-insoluble lignin particles having a mean particle size D50 of 100 nm to 100 pm, preferably of 5 to 30 pm and particularly preferably of 10 to 15 pm; and (b) at least one particle-shaped carrier material that is solid under normal conditions or at least one liquid or semi-solid carrier material.

2. Composition according to claim 1, characterized in that the lignin particles consist of lignin with a proportion of 75 to 95 wt.% and cellulose and hemicellulose with a proportion of 5 to 25 wt.%.

3. Composition according to claim 1 or 2, characterized in that the lignin particles have one or more of the following properties: a. A proportion of C5 and C6 monosaccharides of less than 10 wt.%; b. A bulk density of 425 to 500 kg / m³ 3 c. A density of 500 to 550 kg / m³ 3 d. A shear stress of 100 to 250 Pa; e. A contact friction angle of 30.0° to 35.0°, preferably 30.5° to 32.5°; f. A Carr index of 13.0 to 19.5; g. A flow index ff c from 5.0 to 18.0; h. A moisture content of less than 5 wt% and preferably less than 3.5 wt%; i. A specific surface area (BET) of 0.5 to 100 m² 2 / g, preferably from 0.5 to 50 m 2 / g, especially preferably from 0.5 to 35 m 2 / g and especially preferably from 0.5 to 10 m 2 / g, determined according to DIN 66131 (with nitrogen); j. A pH value of 3 to 7, measured in a 10% aqueous suspension; k. A viscosity of less than 100 mPas, measured in a 10% aqueous suspension.

4. Composition according to any one of claims 1 to 3, characterized in that the lignin is a deodorized lignin and / or has been enzymatically pretreated with cellulase.

5. Composition according to any one of the preceding claims, characterized in that the lignin is a water-soluble or water-insoluble lignin, preferably P93087WO August 11, 2025 Viering, Jentschura & Partner mbB selected from the group consisting of natural lignin, Klason lignin, hydrolyzed lignin, Kraft lignin, ground wood lignin, soda lignin, organosolv lignin, aquasolv lignin, colloidal lignin and mixtures thereof, wherein the lignin is particularly preferably an aquasolv lignin or soda lignin.

6. Composition according to one of the preceding claims, characterized in that the lignin particles are contained in a weight fraction of 0.1 to 99.9 wt.%, preferably of 2 to 80 wt.%, particularly preferably of 5 to 70 wt.%, and particularly preferably of 10 to 65 wt.%, in each case based on the total weight of the ready-to-use composition.

7. Composition according to one of the preceding claims, characterized in that the at least one particle-shaped carrier material, which is solid under normal conditions, has a particle size of 5 nm to 100 pm.

8. Composition according to any of the preceding claims, characterized in that the at least one solid, particulate carrier material under normal conditions is selected from the group consisting of optionally modified starches and starch derivatives, cellulose and cellulose derivatives, silicon dioxide, amorphous silicas, talc, kaolin, mica, nepheline, perlite, phlogopite, synthetic fluorophlogopite, clays, in particular bentonites, magnesium aluminum silicates, boron nitride, lactoglobulin derivatives, organic polymer powders, in particular polyolefins, polycarbonates, polyurethanes, polylactides, polyhydroxybutyrates, polyamides, or silicones, as well as mixtures of these substances, wherein the carrier material preferably consists of talc, hydrophobically modified starch or starch, or combinations thereof.

9. Composition according to one of the preceding claims, characterized in that the at least one solid, particulate, inert carrier material under normal conditions is contained in a weight fraction of 0.1 to 99.9 wt.%, preferably 20 to 98 wt.%, particularly preferably 30 to 95 wt.%, and especially preferably 35 to 90 wt.%, in each case based on the total weight of the ready-to-use composition.

10. Composition according to any of the preceding claims, characterized in that the composition additionally contains an active ingredient, excipient or additive selected from the group consisting of absorbents, antimicrobial substances such as fungicides or bactericidal agents; antioxidants; antiperspirants, antifoaming agents; anti-dandruff agents; antistatic agents; binders; chelating agents, co-emulsifiers; P93087WO August 11, 2025 Viering, Jentschura & Partner mbB Deodorants; emollients; emulsifiers; emulsion stabilizers; humectants; film formers; preservatives; Corrosion inhibitors; solvents; pH regulators; reducing agents; thickeners; surfactants; hair conditioning compounds such as cetrimonium chloride, esterquats, alkylmethicones and amodimethicones; fiber structure-improving agents; protein hydrolysates of animal and / or plant origin; plant extracts; consistency enhancers such as sugar esters, polyol esters and polyol alkyl ethers; clay minerals modified with quaternary ammonium compounds; fats and oils; swelling and penetrating agents; pearlescent agents such as ethylene glycol mono- and distearate and PEG-3 distearate; stabilizers; styling polymers; rheological additives; natural and / or synthetic waxes; cosmetic active ingredients such as panthenol, pantolactone and niacinamide; odor complexing agents; hydrophobic agents; fragrances; and UV protection substances, and combinations thereof.

11. A composition according to any of the preceding claims, characterized in that the composition is a leave-in composition, preferably selected from the group consisting of hairspray, hair conditioner, hair rinse, hairspray, hair treatment, hair tonic, hair stick, heat protectant spray, styling powder, hair fibers, root concealer spray, concealer mascara, mascara, instant volumizing powder, color powder, pressed color powder, eyebrow pencils, gel, mascara and powder and brow filler, products for taming baby hair and for scalp and beard care; hair glow, styling balm, curl cream, hair mousse, hair gel, texture clay, gel wax, pomade, 2-in-1 beard and hair pomade, hair styling cream, hair wax, hair mask, 4-in-1 hair mask, hair oil, hair butter, scalp care products in the sense of skinification of hair care, salon hair care and leave-on conditioner.

12. Composition according to any of the preceding claims, characterized in that the composition is a composition for the temporary coloring of keratinous fibers, in particular human hair, wherein the composition preferably additionally contains at least one color pigment selected from natural pigments, organic pigments, inorganic pigments, colored metal oxides, metal hydroxides, metal oxide hydrates, silicates, metal sulfides, complex metal cyanides, metal sulfates, bronze pigments and / or from colored pigments based on silica, mica or mica which are coated with at least one metal oxide and / or a metal oxychloride, as well as colored pigments based on mica P93087WO August 11, 2025 Viering, Jentschura & Partner mbB and coated with silica, titanium dioxide and, in accordance with Dryflux technology, additionally with carbon, and Color Travel pigments based on mica, which are coated with metal oxides and carbon.

13. A composition for temporarily coloring keratinous fibers, in particular human hair, according to claim 12, characterized in that it contains as a color pigment at least one colored pigment based on fluorphlogopite, silica, mica or mica, which is coated with one or more metal oxides from the group consisting of titanium dioxide (CI 77891), black iron oxide (CI 77499), yellow iron oxide (CI 77492), red and / or brown iron oxide (CI 77491, CI 77499), manganese violet (CI 77742), ultramarine (sodium aluminum sulfosilicates, CI 77007, Pigment Blue 29), chromium oxide hydrate (CI 77289), chromium oxide (CI 77288), tin oxide (CI 77861) and / or iron blue (ferric ferrocyanide, CI 77510) as well as colored Pigments based on mica and coated with silica, titanium dioxide (CI 77891) and, according to Dryflux technology, additionally with carbon, and Color Travel pigments based on mica, coated with titanium dioxide (CI 77891), silica,are coated with carbon and tin oxide as well as carbon black (CI 77266).

14. Means for temporarily coloring keratinous fibers, in particular human hair, according to claim 12, characterized in that the color pigment is a natural pigment selected from the group consisting of henna red, henna neutral, henna black, chamomile flower, sandalwood, black tea, green tea, buckthorn bark, sage, logwood, madder root, catechu, sedre, alkanna root, turmeric root, walnut shell, walnut leaves, senna leaves, indigo and / or cochineal.

15. A means for temporarily coloring keratinous fibers, in particular human hair, according to claim 12, characterized in that the color pigment is an organic pigment selected from the group consisting of insoluble organic dyes or color lakes, which are preferably selected from the group consisting of nitroso, nitro, azo, xanthene, anthraquinone, isoindolinone, isoindolin, quinacridone, perinone, perylene, phthalocyanine, diketopyrrolopyrrole, indigo, thioindigo, dioxazine, and / or triarylmethane compounds.

16. Composition according to any one of claims 12 to 15, characterized in that the color pigment is present in a weight fraction of 0.1 to 60.0 wt.%, preferably of 1.0 to 50.0 wt.%, particularly preferably of 5.0 to 43 wt.%, and in particular P93087WO August 11, 2025 Viering, Jentschura & Partner mbB preferably contains 10 to 35% by weight, based on the total weight of the ready-to-use product.

17. Composition according to one of the preceding claims, characterized in that the composition is in one of the following formulations: powder, aqueous solution, oil, gel, foamable gel, lotion, cream, hair butter, spray, aerosol, pressed powder, stick, suspension, pump foam, hair mascara, eyelash mascara and hair mask.

18. Use of an agent according to any one of claims 12 to 17 as a temporary dye for human hair for intensive coloring, improvement of grey coverage, equalization, color intensity and / or durability of the dyes.

19. Use according to claim 18, characterized in that the agent is a color powder, a color fixative, a color blow-dry lotion, a color blow-dry foam, a color rinse, a color gel or a color cream.

20. Method for temporarily coloring and changing the shape of hair, wherein a means according to one of claims 12 to 17, which is formulated as a powder, pressed powder, leave-in hair mask, hair butter, hair mascara, hair oil, styling cream, pump spray or aerosol spray, is applied or sprayed onto dry hair and the hair is styled before or during application.

21. Oxidative dye for dyeing keratinous fibers, especially human hair, containing coupler components and developer components in a cosmetically acceptable carrier, wherein the coupler component is at least one lignin in the form of water-insoluble lignin particles having a mean particle size D50 of 100 nm to 100 pm.

22. Oxidation dye according to claim 21, characterized in that the lignin particles consist of lignin with a proportion of 75 to 95 wt.% and cellulose and hemicellulose with a proportion of 5 to 25 wt.%.

23. Oxidation dye according to claim 21 or 22, characterized in that the lignin particles have one or more of the following properties: a. A mean particle size D50 of 5 to 30 pm and preferably of 10 to 15 pm; P93087WO August 11, 2025 Viering, Jentschura & Partner mbB b. A proportion of C5 and C6 monosaccharides of less than 10 wt.%; c. A bulk density of 425 to 500 kg / m³ 3 ; d. A density at knockdown of 500 to 550 kg / m³ 3 e. A shear stress of 100 to 250 Pa; f. A contact friction angle of 30.0° to 35.0°, preferably 30.5° to 32.5°; g. A Carr index of 13.0 to 19.5; h. A flow index ff cfrom 5.0 to 18.0; i. A moisture content of less than 5 wt% and preferably less than 3.5 wt%; j. A specific surface area (BET) of 0.5 to 100 m² 2 / g, preferably from 0.5 to 50 m 2 / g, especially preferably from 0.5 to 35 m 2 / g and especially preferably from 0.5 to 10 m 2 / g, determined according to DIN 66131 (with nitrogen); k. A pH value of 3 to 7, measured in a 10% aqueous suspension; l. A viscosity of less than 100 mPas, measured in a 10% aqueous suspension.

24. Oxidation dye according to one of claims 21 to 23, characterized in that the lignin is a GS lignin or an HGS lignin, wherein it is preferably isolated from hardwood, grasses or monocotyledonous plants.

25. Oxidation dye according to one of claims 21 to 24, characterized in that the lignin is a deodorized lignin and / or has been enzymatically pretreated with cellulase.

26. Oxidation dye according to one of claims 21 to 25, characterized in that the lignin is a water-soluble or water-insoluble lignin, preferably selected from the group consisting of natural lignin, Klason lignin, hydrolyzed lignin, Kraft lignin, ground wood lignin, soda lignin, organosolv lignin, aquasolv lignin, colloidal lignin and mixtures thereof, wherein the lignin is particularly preferably an aquasolv lignin or soda lignin.

27. Oxidation dye according to one of claims 21 to 26, characterized in that the lignin particles are contained in a weight fraction of 0.1 to 99.9 wt.%, preferably 2 to 70 wt.%, particularly preferably 5 to 50 wt.%, and particularly preferably 10 to 35 wt.%, in each case based on the total weight of the ready-to-use agent.

28. Oxidation dye according to one of claims 21 to 27, characterized in that the developer component is selected from the group P93087WO August 11, 2025 Viering, Jentschura & Partner mbB consisting of primary aromatic amines with an extended, free or substituted hydroxy or amino group located in the para- or ortho- position; diaminopyridine derivatives; heterocyclic hydrazones; 4-aminopyrazole derivatives; and 2,4,5,6-tetraaminopyrimidine and its derivatives.

29. Oxidation dye according to one of claims 21 to 28, characterized in that it contains at least one further coupler component, which is preferably selected from the group consisting of m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenol derivatives.

30. Oxidation dye according to claim 29, characterized in that the at least one further coupler component is selected from the group consisting of 1-naphthol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 1-phenyl-3-methyl-pyrazolone-5, 2,4-dichloro-3-aminophenol, 1,3-bis-(2',4'-diaminophenoxy)-propane, 2-chlororesorcinol, 4-chlororesorcinol, 2-chloro-6-methyl-3-aminophenol, 2-amino-3-hydroxypyridine, 2-methylresorcinol, 5-methylresorcinol and 2-methyl-4-chloro-5-aminophenol.

31. Oxidation dye according to one of claims 21 to 30, characterized in that it further contains at least one direct dye.

32. Oxidation dye according to claim 31, characterized in that the direct dye is cationic.

33. Oxidation dye according to one of claims 21 to 32, characterized in that it further contains at least one surfactant, which is preferably selected from the group consisting of anionic, zwitterionic, ampholytic, nonionic and cationic surfactants.

34. Method for dyeing keratinous fibers, in which the agent according to one of claims 21 to 33 is applied to the fibers and rinsed off after an exposure time.

35. Use of water-insoluble lignin particles according to one of claims 21 to 26 as a coupler component in an oxidation dye for dyeing keratinous fibers, in particular human hair.

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