A dye composition comprising a combination of two plant extracts of Lausonia inermis

Abstract

The present invention relates to a dye composition comprising a combination of two extracts of Lawsonia inermis and a method for preparing the same. Furthermore, the present invention relates to a cosmetic use of said composition for dyeing keratin fibers. Finally, the present invention relates to a cosmetic method for dyeing keratin fibers comprising the application of said composition.

Description

Technology Field

[0001] The present invention relates to two natural dyes, specifically Lausoniina Inermis ( Lawsonia inermis The present invention relates to a dye composition comprising a combination of two extracts of ). Furthermore, the present invention relates to a cosmetic use of said composition for dyeing keratin fibers. Finally, the present invention relates to a cosmetic method for dyeing keratin fibers comprising the application of said composition. Background Technology

[0002] Methods for dyeing hair involve oxidative or permanent dyes. These chemical dyeing methods implement one or more oxidative dye precursors, usually one or more oxidative bases combined with one or more optional couplers.

[0003] These oxidation bases are colorless or faintly colored compounds that allow access through an oxidative condensation process to colored species trapped within hair fibers when combined with the oxidizing product.

[0004] However, oxidative dyes are known to cause skin problems. Furthermore, oxidative dyes are endocrine disruptors that have a negative impact on the environment and have been proven to cause cancer and allergies.

[0005] In addition, colored molecules and dyes may be natural compounds derived from plants or trees.

[0006] Commonly called henna Lausoniina Inermis ( Lawsonia inermisIt belongs to the family Lythraceae. This shrub can reach a size of 6 meters and grows naturally in the tropical and subtropical regions of Africa and Asia. In the oldest individuals, it has gray bark, dense branching, and branches with square thorns. The leaves grow opposite each other and are simple as a single mass. Fragrant white or red flowers cluster in the form of large pyramidal conical inflorescences 25 cm long.

[0007] Henna leaves, which produce an orange hue, have been used for over 5,000 years to dye hair and skin or to dye fabrics.

[0008] Their dye properties are caused by lauson (2-hydroxy-1,4-naphthoquinone), which reacts with keratin present in the skin or nails through the Michelson addition reaction.

[0009]

[0010] However, it is difficult to achieve the full range of hair shades, from gold to dark gold and even black, with henna alone.

[0011] Other plants have also been described specifically for dyeing hair or other keratinous materials, as sources of extracts or powders for dyeing. However, each plant produces a specific color.

[0012] Furthermore, the combination of various plant extracts carries the risk of inducing undesirable interactions in pigments or extract compounds. These interactions may be color issues, such as dye abnormalities, or dermatological side effects.

[0013] Furthermore, it is difficult to provide shades covering the entire color range, ranging from gold to dark gold and even black, using only plant extracts or powders without clearly unsuitable hair, and therefore the use of henna extract as a base is numerically limited.

[0014] It is even more difficult to use a single plant source to produce dye compositions that allow for the acquisition of a wide range of dyes, from gold to dark gold. This is highly desirable, simplifies the procurement of plant materials, and justifies the production of extracts and dye compositions on an industrial scale.

[0015] In the field of hair dyes, the inventors describe tone-on-tone dyes, or permanent or non-permanent dyes, the latter generally using more hydrogen peroxide and alkaline chemicals.

[0016] Generally, color-adjusting dyes are used to enhance or strengthen the hair's natural color, creating highlights and a rich shine.

[0017] Therefore, this is selected from color tones that are the same as or darker than natural hair for a long time.

[0018] In the field of permanent or non-permanent hair dyes, it is desirable for the dye to resist hair washing.

[0019] When henna is used, it produces a copper or red color through the use of a somewhat standardized extract. This is the case as described above, and obtaining a wide range of colors using a dye composition based solely on henna has not been described. The problem to be solved

[0020] The present invention relates to both color-changing dyes and permanent dyes.

[0021] In conclusion, it is practically necessary to develop a color-modifying or permanent dye approach that limits the number of plant extracts, simplifies the formulation, and avoids interactions and non-compatibility, while allowing the application of hair dyes from natural products, specifically henna, to the entire range of hair colors, specifically to gray hair. Specifically, it is necessary to develop and provide a dye composition based on a single plant source that covers a range of shades.

[0022] Specifically, the present invention is a dye composition,

[0023] - It is natural and free of animal products, that is, based on dye active ingredients from plants, microorganisms, or microalgae;

[0024] - The exposure time for dyeing hair is advantageously short, less than 1 hour;

[0025] - Preferably, it is possible with a single application, including hair dyeing;

[0026] - Preferably organic and extremely plant-based (vegan);

[0027] - Hair dye maintains good color after multiple washes, including 10, or advantageously 15, hair washes.

[0028] The goal is to provide a dye composition.

[0029] In addition, there is an attempt to find a permanent hair dye that avoids the use of hydrogen peroxide and alkaline chemicals.

[0030] Moreover, it is desirable to be able to achieve all desired colors.

[0031] Accordingly, the inventors of the present invention have developed a dye composition based on a combination of two henna extracts while achieving a wide range of colors. Specifically, for use in the hair field, the composition covers the entire shade range from black to very light gold.

[0032] Thus, the inventors of the present invention have developed a dye composition based on a combination of two henna extracts that allows for the achievement of a dual purpose, including a wide range of colors. Specifically, for use in the hair field, the composition has a very wide range of shades while using a single source of plant raw materials.

[0033] The present invention relates to a method for preparing a dye composition, specifically a method for preparing a cosmetic dye composition for dyeing keratin fibers, wherein

[0034] - 7% to 60% by weight of Lausone based on the total weight of the dried extract including Lausoniina Inermis ( Lawsonia inermis A step of providing an aerial fraction extract A of ), wherein the lauson is clearly generated from the enzymatic hydrolysis of a glycosylated lauson derivative such as a henoside; and

[0035] - Based on the total weight of the dried extract, less than 0.6 wt% of lausone, at least 15 wt% of phenolic compounds, and at least 60 wt% of sugar compounds including polysaccharides including Lausoniina Inermis Step of providing aerial partial extract B of;

[0036] - A step of mixing extract A and extract B; and

[0037] - Step of obtaining a dye composition

[0038] It concerns a method including.

[0039] In addition, the present invention relates to a dye composition obtained by the disclosed method and its use for dyeing keratin fibers.

[0040] In addition, the present invention relates to a method for dyeing human keratin fibers, wherein

[0041] (a) a step of providing the dye composition disclosed herein in powder form;

[0042] (b) a step of preparing a water-soluble composition by adding and mixing water, specifically water, to the powder of step (a) at a temperature of 20°C to 98°C;

[0043] (c) a step of applying to keratin fibers and optionally treating the fibers while heating them;

[0044] (d) rinsing step; and

[0045] (e) Optionally, a step to repeat steps (c) and (d).

[0046] It concerns a method including.

[0047] Further aspects of the present invention are incorporated by reference in the claims and / or described herein. means of solving the problem

[0048] The present invention relates to a method for preparing a dye composition, specifically a method for preparing a cosmetic dye composition for dyeing keratin fibers, wherein

[0049] - 7% to 60% by weight of Lausone based on the total weight of the dried extract including Lausoniina Inermis A step of providing an aerial fraction extract A, wherein the lauson is clearly generated from the enzymatic hydrolysis of a glycosylated lauson derivative such as a henoside; and

[0050] - Based on the total weight of the dried extract, less than 0.6 wt% of lauson, at least 15 wt% of phenolic compounds, and at least 60 wt% of sugar compounds including polysaccharides (e.g., mucilage), specifically 60 wt% to 80 wt% including Lausoniina Inermis Step of providing aerial partial extract B of;

[0051] - A step of mixing extract A and extract B; and

[0052] - Step of obtaining a dye composition

[0053] It concerns a method including.

[0054] In addition, the present invention relates to a dye composition obtained by the method disclosed herein.

[0055] definition

[0056] The following terms have the following meanings when used herein.

[0057] "Plant extract" refers to a product extracted from a plant, regardless of whether it is the whole plant, aerial parts, underground parts, flowers, or fruits. Extraction may consist of simple compression or may involve the use of an extraction solvent. While different types of solvents may be considered specifically in the case of henna extract A, advantageously, it is water, aqueous alcoholic solvents, or alcoholic solvents.

[0058] The present invention attempts to establish a synthetic route that is more environmentally friendly and allows the active ingredient thus obtained to be claimed to be natural. Accordingly, the solvent(s) used in the present invention are preferably natural solvents and / or solvents of natural origin, derived from renewable resources as opposed to fossil resources, and advantageously, such solvents are obtainable by an environmentally respectful process. The extract thus obtained is a natural extract and / or is of natural origin derived from renewable resources as opposed to fossil resources.

[0059] "Dry extract" refers to an extract that contains no extraction solvent or medium, or contains only insignificant trace amounts thereof. Such a dry extract is, in this way, a plant, specifically in the case of henna extract A. Lausoniina Inermis It includes only substances derived from.

[0060] "Standardized extract" refers to an extract having a specific content for at least one dye component of a plant extract. Standardized extracts are typically obtained by adding an inert carrier to the plant extract in an amount that may vary for each batch.

[0061] The above "carrier" must be inert with respect to the extract and its components. It does not interact with either the extract or its components, more specifically with lauson, contributes to the protection of the extract, and ensures that the final content of the active extract or molecule is standardized.

[0062] The carrier can be selected from propanediol, pentanediol, glycerin, propylene glycol, methyl THF, and amyl alcohol.

[0063] The carrier may also be selected from sugar and polysaccharide derivatives such as fructose, glucose, saccharose, maltodextrin, cellulose derivatives, starch (e.g., corn, wheat, or rice starch), agar, gum, and mucilage; and polyols such as mannitol, sorbitol, xylitol, etc.

[0064] The carrier is preferably a natural carrier and / or has a natural origin from renewable resources as opposed to fossil resources, and advantageously, these carriers can be obtained by an environment-respecting process.

[0065] "Standardized dry extract" refers to a standardized extract that contains no extraction solvent or only insignificant trace amounts thereof.

[0066] "Powder" refers to a product in the form of fine particles having an average particle size of 0.1 μm to 250 μm, specifically 1 μm to 250 μm. Such fine particles can be obtained by grinding. Grinding can be performed by any suitable means that allows for the reduction and acquisition of the size of fine particles as mentioned above.

[0067] Advantageously, the powder according to the present invention is a dry, pulverulent product with little moisture. The powder according to the present invention is soluble in water or easily dispersible in water, and can be used to obtain a water-soluble or water-alcoholic liquid composition comprising 20% ​​to 60% by weight, more specifically 30% to 50% by weight, and more specifically about 40% by weight of the dry material based on the weight of the dry material.

[0068] "Plant powder" means a pure natural product originating from plants, including dried fruits, that is ground by crushing or any other mechanical means, regardless of whether it is the whole plant, aerial parts, underground parts, flowers, or fruits.

[0069] "Aerial part" means a part of a plant above the ground, for example, leaves, stems, flowers, seeds, and branches, specifically leaves, branches, and stems or a mixture thereof, preferably leaves, branches, or a mixture thereof.

[0070] "Glycosylated lauson derivatives" are also called glycosides or heterosides and refer to any compound of the following general chemical formula (I):

[0071]

[0072] Here, R1, R2 and R3 are independently sugars such as H or glucose, at least one of R1 to R3 is different from H, and hydrolysis of the glycosidic bond(s) induces the formation of an aglycone that undergoes a self-oxidation reaction to form a lauson.

[0073] Specifically, henosides A, B, and C are glycosylated lausone derivatives.

[0074] "Enzymatic hydrolysis" is endogenous Lausoniina Inermis Enzymes or enzymes derived from an endogenous source, preferably endogenous Lausoniina InermisIt refers to a hydrolysis reaction catalyzed by an enzyme that may be an enzyme, and said enzyme is a glycosidase such as β-glycosidase and [Gallo et al. ], its action is understood to induce the cleavage of glycosidic bonds in glycosylated lausone derivatives.

[0075] The term "stable over time" is disclosed herein Lausoniina Inermis With respect to the extract, it means that the quantified amount of lauson initially present in the extract is not reduced to less than 50%, advantageously less than 40%, specifically less than 30%, advantageously less than 20%, clearly less than 15%, and advantageously less than 10% within one month at room temperature (15°C to 25°C) and 60% relative humidity (RH), and is protected from light. Room temperature values ​​are defined in the European Pharmacopoeia.

[0076] The stability of extract A as disclosed herein may also be evaluated under so-called accelerated stability conditions. These conditions are a temperature of 40°C (±2) and RH of 75% (±5). The lausone content of the extract is "stable over time" under accelerated stability conditions if the amount of lausone initially present in the extract does not decrease to less than 50%, advantageously less than 40%, preferably less than 30%, specifically less than 20%, clearly less than 15%, and advantageously less than 10% within one month.

[0077] "Neutral pH" means a pH range of 6.5 to 7.5, specifically about pH 7.

[0078] "Acidic pH" means pH less than 7, favorably less than 6.5, and more favorably less than 6.

[0079] "Weak polarity" refers to a solvent characterized by a dipole moment of less than 2.0 D.

[0080] "Alcohol" is a compound of the chemical formula R4-OH, where R4 is a hydrocarbon group, specifically a (C1-C6) alkyl group or a C4-C12 It refers to a compound having a hydrocarbon group. (C1-C6) Alcohols containing an alkyl group are referred to herein as ≪C1-C6 alcohol≫. (C4-C 12 Alcohols containing hydrocarbon groups are defined herein as ≪C4-C 12 It is referred to as alcohol.

[0081] "Chlorinated solvent" means an alkane in which some or all of the hydrogen atoms are substituted with chlorine atoms, that is, a saturated hydrocarbon containing 1 to 6 carbon atoms, specifically 1 to 3 carbon atoms.

[0082] "Ketone" means a compound of the chemical formula R5-CO-R6, where R5 and R6 are the same or different (C1-C6) alkyl groups.

[0083] "Ether" means a compound of the chemical formula R7-O-R8, where R7 and R8 are the same or different (C1-C6) alkyl groups.

[0084] The chemical formula for "ester" is R9-COO-R 10 As a compound of, R9 and R 10 It refers to compounds having (C1-C6) alkyl groups that may be identical or different. Esters are specifically acetates, i.e., CH3COO-R 10 It can be a compound.

[0085] "(C1-C6) alkyl" groups refer to saturated, linear, or branched hydrocarbon chains advantageously comprising 1 to 6, preferably 1 to 4, carbon atoms. Examples include methyl, ethyl, propyl, butyl, isobutyl, sec-butyl, ter-butyl, pentyl, or hexyl groups.

[0086] C4-C 12 "Hydrocarbon chain" refers to a linear or branched, saturated or unsaturated, preferably saturated hydrocarbon chain comprising 4 to 12, preferably 4 to 8, carbon atoms. "C4-C 12Examples of “hydrocarbon chains” include butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl, including any positional isomers, but are not limited thereto.

[0087] "Saturated or unsaturated hydrocarbons" refer to compounds composed uniquely of hydrogen and carbon atoms.

[0088] "Keratin fibers" refers to keratin present in the epidermis and outer layer, such as skin, hair, eyelashes, and eyebrows, specifically in hair.

[0089] "Cosmetically acceptable" means useful in the manufacture of cosmetic compositions, generally safe, non-toxic, biologically or otherwise desirable, and clearly acceptable for cosmetic use by topical application on keratin fibers, specifically hair and scalp.

[0090] "Cosmetically acceptable excipients" means excipients containing ingredients suitable for formulating cosmetic compositions, such as creams, lotions, shampoos, and emulsions, or for application on keratin fibers, specifically on hair.

[0091] Henna Extract A

[0092] The dye composition of the present invention comprises at least one specific henna extract referred herein as "Extract A".

[0093] This extract A is characterized by a high lauson content.

[0094] Accordingly, extract A contains 7% to 60% by weight of lausone based on the total weight of the dry extract. This lausone content is advantageously stable over time, even under accelerated stability conditions.

[0095] In some embodiments, the lauson content of extract A is protected from light and is not reduced to less than 50%, advantageously less than 40%, specifically less than 30%, advantageously less than 20%, more advantageously less than 10% within 3 months at room temperature (15°C to 25°C) and 60% relative humidity (RH).

[0096] Advantageously, the lauson content of extract A is protected from light and is not reduced to less than 50%, advantageously less than 40%, specifically less than 30%, advantageously less than 20%, and more advantageously less than 10% within 6 months at room temperature (15°C to 25°C) and 60% relative humidity (RH).

[0097] Preferably, the lauson content of extract A is protected from light so that it does not decrease to less than 50%, advantageously less than 40%, specifically less than 30%, advantageously less than 20%, and more advantageously less than 10% within 12 months at room temperature (15°C to 25°C) and 60% relative humidity (RH).

[0098] Advantageously, the lauson content of extract A does not decrease to less than 50%, advantageously less than 40%, specifically less than 30%, advantageously less than 20%, and more advantageously less than 10% within 3 months at a temperature of 40°C (±2) and RH of 75% (±5).

[0099] Specifically, the lauson content of extract A does not decrease to less than 50%, advantageously less than 40%, specifically less than 30%, advantageously less than 20%, and more advantageously less than 10% within 6 months at a temperature of 40°C (±2) and RH of 75% (±5).

[0100] Therefore, unlike many commercially available henna extracts which have a low lauson content and which rapidly decrease over time due to the condensation of various compounds containing amino groups, specifically proteins, peptides, or amino acids, extract A disclosed herein contains a high and stable amount of lauson.

[0101] The lauson in Extract A is typically produced from the enzymatic hydrolysis of glycosylated lauson derivatives, such as henosides. A method for preparing this extract is described herein.

[0102] Extract A may additionally contain luteolin, apigenin, and 2,3,4,6-tetrahydroxyacetophenone.

[0103] In some implementations, Lausoniina Inermis As aerial part extract A, 7% to 60% by weight of Lausone based on the total weight of the dry extract Extract A, which includes lauson, is produced from the enzymatic hydrolysis of a glycosylated lauson derivative such as henoside, and which may further include luteolin, apigenin, and 2,3,4,6-tetrahydroxyacetophenone, can be prepared according to the process as described herein.

[0104] Extract A may additionally be characterized by one or more of the following advantageous features, advantageously all of them:

[0105] - Extract A contains 7% to 50% by weight or 10% to 50% by weight, specifically 15% to 40% by weight, based on the total weight of the dried extract. It comprises. Advantageously, extract A contains at least 7% by weight of lauson, advantageously at least 10% by weight, at least 15% by weight, preferably at least 20% by weight, and more advantageously at least 25% by weight, based on the total weight of the dry extract. Including, the percentage is expressed based on the total weight of the dried extract (prior to the resulting addition of any dried carrier). The lausone content can be determined according to the HPLC assay method described after the Examples section (Method 1).

[0106] - Extract A does not contain 2% by weight or more, preferably 1.5% by weight or more, or clearly 1% by weight or more of protein, peptide, or amino acid based on the total weight of the dry extract, and advantageously contains 0% by weight to 1% by weight or 0.1% by weight to 1% by weight of protein, peptide, or amino acid based on the total weight of the dry extract. Free protein, peptide, and amino acid may be detected by ninhydrin spectrophotometry according to the method described after the Examples section (Method 2).

[0107] - Extract A contains less than 25% by weight of chlorophyll, specifically chlorophyll a and / or chlorophyll b, based on the total weight of the dry extract, or less than 20% by weight, advantageously less than 10% by weight, based on the weight of the dry extract. In some embodiments, Extract A does not contain 5% by weight or more, preferably 2% by weight or more, of chlorophyll based on the total weight of the dry extract. In some embodiments, Extract A does not contain chlorophyll. Chlorophyll may be tested by a gravimetric method according to the method described after the Examples section (Method 3).

[0108] - Extract A contains 1% to 40% by weight, advantageously 2% to 30% by weight, of phenolic compounds based on the total weight of the dry extract. The phenolic compound content can be determined by spectrophotometry according to the method described herein after the section on examples (Method 4).

[0109] - Extract A does not contain 5% by weight or more of sugars based on the total weight of the dried extract, and advantageously contains 0.1% to 5% by weight, more advantageously 0.5% to 5% by weight. The sugar content can be determined by a calorimetric assay using dinitrosalicylic acid (Method 5).

[0110] - Extract A contains phenolic compounds such as gallic acid, coumaric acid (specifically, para-coumaric acid), 2,3,4,6-tetrahydroxyacetophenone, and 2,3,5-trihydroxyacetophenone; flavonoids such as luteolin, apigenin, catechin, 3',4',5,7-tetrahydroxyflavanone, and 3',5,7-trihydroxy-4'-methylflavone; sterols such as β-sitosterol; and triterpenes such as lupeol. and / or their heterosides, e.g., ralioside, myrciaphenol A, 1,2-dihydroxy-4-O-glycosyloxynaphthalene (also called 4-O-β-D-glucopyranoside), luteolin-4'-O-glucoside, apigenin-7-O-β-glucoside, luteolin-3'-O-glucoside, apigenin-4'-O-β-glucoside, and luteolin-6-C-neoheciferidoidide further comprise. In some embodiments, extract A comprises phenolic compounds such as gallic acid, coumaric acid (specifically, para-coumaric acid), 2,3,4,6-tetrahydroxyacetophenone, and 3,4,5-trihydroxyacetophenone; Flavonoids such as luteolin, apigenin, catechin, 3',4',5,7-tetrahydroxyflavanone, and 3',5,7-trihydroxy-4'-methylflavone; and / or their heterosides, e.g., ralioside, myrciaphenol A, 1,2-dihydroxy-4-O-glycosyloxynaphthalene, luteolin-4'-O-glucoside, apigenin-7-O-β-glucoside, luteolin-3'-O-glucoside, apigenin-4'-O-β-glucoside and luteolin-6-C-neoheciferidoid.

[0111] - Extract A further comprises 2,3,4,6-tetrahydroxyacetophenone and optionally 3,4,5-trihydroxyacetophenone and / or 1,2-dihydroxy-4-O-glycosyloxynaphthalene.

[0112] - Extract A additionally contains coumaric acid, specifically para-coumaric acid.

[0113] - Extract A further contains 3,4,5-trihydroxyacetophenone and / or 1,2-dihydroxy-4-O-glycosyloxynaphthalene.

[0114] - Extract A further comprises glycosylated luteolin, specifically luteolin-6-C-neohesperidose.

[0115] Flavonoids such as luteolin and apigenin have free radical scavenging and antioxidant effects [Romanov et al. , [Neoplasma 2001, 48(2): 104-107], as well as possessing many interesting biological properties such as anti-inflammatory activity, which, combined with the ability to absorb UV rays, confers the ability to provide protection from UV irradiation [Saewan et al. , [JAPS 2013, 3(9): 129-141]. Although hair photoprotection is not a commonly targeted topic, the chemical effects of UV irradiation and their impact on the hair shaft should not be overlooked [Draelos, Dermatol. Clin. 2006, 24: 81-84]. Therefore, the presence of compounds with photoprotective effects in cosmetic compositions intended for hair dyeing is particularly interesting.

[0116] Luteolin and apigenin are also widely known natural dyes that can be used to color hair and fabrics.

[0117] In addition, apigenin has been identified as a hair growth promoter [Huh et al. Arch. Dermatol. Res. 2009, 301: 381-385].

[0118] In addition, polyphenols such as 2,3,4,6-tetrahydroxyacetophenone and para - Phenolic acids such as coumaric acid have antioxidant and photoprotective properties [Nichols et al. , Arch. Dermatol. Res. 2010, 302: 71-83]. Extract A also Lausonia Inermis The aerial part of, specifically Lausonia Inermis It may contain any compound naturally present in the leaves and / or branches.

[0119] In some embodiments, the extract A disclosed herein may be in the form of a dry extract, advantageously in the form of a powder with a particle size clearly less than 250 μm.

[0120] In some embodiments, the extract A disclosed herein may be in the form of a standardized extract AN, specifically a standardized dried extract AN. The standardized extract AN, specifically the standardized dried extract AN is Laosonia Inermis It includes aerial part extract A and a carrier.

[0121] Accordingly, in some embodiments, particularly advantageously when the dye composition is a cosmetic composition, said composition comprises a standardized extract AN, specifically a standardized dried extract AN, obtained by adding an inert carrier to extract A as disclosed herein to standardize the lauson content of the extract. In other words, the dye composition of the present invention comprises extract A and an inert carrier as disclosed herein, and extract A and the inert carrier form a standardized extract AN, specifically a standardized dried extract AN.

[0122] Standardized extract AN is characterized by one or more of the following advantageous features, preferably all of them (percentages are expressed as weights based on the total weight of standardized extract AN):

[0123] - Standardized extract AN contains 0.6% to 1.4% by weight of lausone, advantageously 1% to 1.3% by weight, specifically about 1.3% by weight;

[0124] - The inert carrier is protein-free;

[0125] - The inert carrier is cosmetically acceptable;

[0126] - The carrier is selected from the group consisting of propanediol, pentanediol, glycerin, propylene glycol, methyl THF, and amyl alcohol, or the carrier is selected from the group consisting of fructose, glucose, saccharose, maltodextrin, cellulose derivatives, starch (e.g., corn, wheat, or rice starch), sugar or polysaccharide derivatives such as agar, gum, and mucilage, and polyols such as mannitol, sorbitol, xylitol, etc.;

[0127] - Standardized extract AN contains luteolin, apigenin, and 2,3,4,6-tetrahydroxyacetophenone;

[0128] - Standardized extract AN contains 3,4,5-trihydroxyacetophenone and / or 1,2-dihydroxy-4-O-glycosyloxynaphthalene;

[0129] - Standardized extract AN contains coumaric acid, specifically para-coumaric acid;

[0130] - Standardized extract AN contains the compounds previously listed for extract A;

[0131] - Standardized dry extract AN contains 0.2% to 3.0% by weight of a phenolic compound;

[0132] - Standardized dry extract AN contains glycosylated luteolin, specifically luteolin-6-C-neohesperidoid;

[0133] - Standardized dry extract AN contains 0.05% to 1.0% by weight of luteolin;

[0134] - Standardized dry extract AN contains 0.01% to 0.5% by weight of apigenin;

[0135] - Standardized dry extract AN contains 0.01% by weight to 0.1% by weight of coumaric acid, specifically para-coumaric acid;

[0136] - Standardized dry extract AN contains 0.05% to 1.0% by weight of 2,3,4,6-tetrahydroxyacetophenone;

[0137] - The standardized dry extract does not contain protein, peptide, or amino acid in an amount of 0.2% by weight or more based on the weight of the protein, peptide, or amino acid, but advantageously contains 0% by weight to 0.2% or more, and advantageously contains 0.1% by weight to 0.2% by weight;

[0138] - Standardized dry extract AN does not contain chlorophyll;

[0139] - Standardized dry extract AN does not contain 0.5% by weight or more of sugar compounds based on weight, and advantageously contains 0.01% to 0.5% by weight, and advantageously 0.05% to 0.5% by weight;

[0140] - Standardized dry extract AN complies with stability specifications, including under previously defined accelerated conditions for henna extract A;

[0141] - Standardized dry extract AN contains at least 80% by weight of a carrier, advantageously at least 90% by weight, clearly at least 92% by weight, specifically at least 95% by weight.

[0142] In some implementations, Lausonia Inermis The standardized dry extract AN contains 0.6% to 1.4% by weight of lauson based on the total weight of the dry extract, and additionally contains luteolin, apigenin, and 2,3,4,6-tetrahydroxyacetophenone.

[0143] In some implementations, Lausoniina Inermis The standardized dry extract AN is based on the total weight of the dry extract

[0144] - 0.05 wt% to 1.0 wt% of luteolin;

[0145] - 0.01 wt% to 0.5 wt% of apigenin; and

[0146] - Contains 0.01 wt% to 1 wt% or 0.05 wt% to 1.0 wt% of 2,3,4,6-tetrahydroxyacetophenone.

[0147] Preferably, the standardized dry extract AN is in the form of a dry extract, advantageously in the form of a powder with a particle size clearly less than 250 μm.

[0148] Preparation of Extract A

[0149] Lausonia Inermis The quantification of lauson found in a free state in leaves is actually very low, so having high lauson content Lausonia Inermis The preparation of extracts can be cumbersome.

[0150] In plants, lausons exist predominantly in the form of heterosides [Gallo et al. Rev. Bras. Pharmacogn. 2014, 23: 133-140; COLIPA No. C169, 2013].

[0151] Henosides A, B, and C were clearly identified as monoglycosylated lausone derivatives.

[0152] The hydrolysis of these precursors and the subsequent self-oxidation of the aglycone produced induce the formation of lauson according to the reaction scheme shown below.

[0153]

[0154] Therefore, numerous announced Lausonia Inermis The extraction process includes a hydrolysis step of the henoside using an acidic medium at a pH typically in the range of pH 1 to 3.

[0155] The inventors of the present invention have obtained an extract containing a high content of lauson by performing enzymatic hydrolysis of a glycosylated lauson derivative. Lausonia Inermis An extraction process was developed. The above extract is distinguished by its stability over time.

[0156] Therefore, to my advantage, Lausoniina Inermis Aerial part extract A of

[0157] (a) Lausoniina Inermis In order to enzymatically hydrolyze, in part or in whole, the glycosylated lauson derivative, such as the henoside initially present in the aerial portion of, Lausoniina Inermis A step of immersing an aerial portion of in water with a pH range of 4 to 8 to provide an aqueous solution containing lauson;

[0158] (b) a step of adding an organic solvent to the solution obtained from step (a) to provide a water-soluble phase and an organic phase, wherein the organic solvent is C4 to C 12 A step selected from linear or branched alcohols or solvents having less than 10% by weight, advantageously less than 5% by weight, miscibility with water at 25°C;

[0159] (c) a step of recovering the organic phase recovered from step (b); and

[0160] (d) A step of concentrating the organic phase recovered from step (c) to provide a concentrated lauson extract A.

[0161] It is obtained by a process including.

[0162] Specifically, the immersion in step (a) Lausoniina Inermis The aerial part is a leaf, a branch, or a mixture thereof. The leaf may be fresh or dried, preferably dried.

[0163] Step (a) is preferably carried out at a temperature of 20°C to 60°C or 20°C to 50°C, specifically 25°C to 45°C, more specifically in the range of 30°C to 45°C, typically about 40°C.

[0164] Step (a) is understood to be carried out at a pH at which the enzymes or enzymes catalyzing the hydrolysis of the glycosylated lauson derivative can function. Specifically, step (a) is carried out at a pH of 4 to 8, preferably 5 to 7.5, advantageously 5.5 to 7.5, typically in a neutral pH range.

[0165] Lausoniina Inermis The aerial portion of is typically immersed for 15 minutes to 2 hours, preferably 15 minutes to 1 hour, advantageously for about 30 minutes.

[0166] In some embodiments, step (a) is performed under stirring for 15 minutes to 2 hours, preferably 15 minutes to 1 hour, advantageously about 30 minutes.

[0167] Lausoniina Inermis The aerial part of is typically Lausoniina Inermis It is immersed in a volume of water that is 2 to 15 times, advantageously 5 to 15 times, more advantageously 6 to 10 times, typically 10 times or more, the weight of the air portion. For example, the process is 100 g of Lausoniina Inermis When performed on the aerial portion of, the volume of water used in step (a) may be 200 mL to 1,500 mL or 500 mL to 1,500 mL, advantageously in the range of 600 mL to 1,000 mL, typically 1,000 mL.

[0168] In some embodiments, a pectinase-type enzyme may be added in step (a).

[0169] In some embodiments, an organic solvent is added directly to the aqueous solution obtained in step (a). Next, the aqueous solution contains plant material and a precipitated product. In these embodiments, it should be understood that the organic solvent is added directly to the aqueous solution obtained in step (a), that is, no filtration step is performed between step (a) and step (b).

[0170] In some embodiments, the process is Lausoniina Inermis The process includes a filtration step between step (a) and step (b) for separating the aerial portion of from an aqueous solution containing lauson. Alternatively, in some embodiments, the process Lausoniina Inermis It includes a filtration step between step (c) and step (d) for separating the aerial portion of from the organic phase recovered / collected in step (c).

[0171] Next, an organic solvent is added to the aqueous solution obtained in step (a). The aqueous solution contains plant material and precipitated material. It should be understood that the organic solvent is added directly to the aqueous solution obtained in step (a), that is, no filtration step is performed between step (a) and step (b).

[0172] Step (b) can be performed in batches or continuously.

[0173] In some specific batch implementations, step (b) of the process is the following three sub-steps

[0174] (b.1) A step of adding an organic solvent to the aqueous solution obtained in step (a);

[0175] (b.2) a step of stirring the solution obtained in step (b.1) for 15 minutes to 2 hours, specifically for 15 minutes to 1 hour, typically for about 30 minutes; and

[0176] (b.3) A step of emptying the mixture obtained in step (b.2) until two distinct phases, namely a water-soluble phase and an organic phase, are obtained.

[0177] Includes

[0178] Therefore, the progression of sub-steps (b.1), (b.2), and (b.3) induces the formation of a water-soluble phase and an organic phase.

[0179] During step (b), specifically during step (b.1), the volume of organic solvent added is such that the volume ratio of the organic solvent added during step (b) to the water used during step (a) is 0.25 to 2, clearly 0.5 to 2, clearly 0.8 to 1.5, specifically 1 to 1.3.

[0180] In some embodiments, the organic solvent added during step (b) of the process disclosed herein, specifically during step (b.1), is a weakly polar solvent. Although weakly polar, the organic solvent is understood to dissolve lausone. Accordingly, the solubility of lausone in the organic solvent added in step (b), specifically in step (b.1), is 70 wt% or more at 25°C, clearly 80 wt% or more, advantageously 90 wt% or more, and the percentage is expressed based on the total weight of lausone present in the aqueous solution containing lausone obtained from step (a).

[0181] In some embodiments, the organic solvent added during step (b) of the process disclosed herein, specifically during step (b.1), is selected from the group consisting of C1 to C6 alcohols, chlorinated solvents, ketones, ethers, esters, and mixtures thereof that satisfy the following criteria:

[0182] - The miscibility of water in the above organic solvent is less than 10 weight% at 25°C, advantageously less than 5 weight%, and

[0183] - The miscibility of the above organic solvent in water is less than 10 weight% at 25°C, advantageously less than 5 weight%.

[0184] Specifically, the organic solvent may be selected from the group consisting of C1 to C6 alkyl acetates such as n-amyl alcohol, dichloromethane, chloroform, methyl isobutyl ketone, diethyl ether, diisopropyl ether, dibutyl ether, methyl ter-butyl ether, ethyl acetate, isopropyl acetate, butyl acetate, isoamyl acetate, and mixtures thereof.

[0185] In some embodiments, the organic solvent added in step (b), specifically during step (b.1), is preferably a mixture of C1 to C6 alkyl acetates or C1 to C6 alkyl acetates selected from ethyl acetate, isopropyl acetate, butyl acetate, isoamyl acetate, and any mixture thereof. Preferably, the organic solvent is isopropyl acetate.

[0186] In some embodiments, the organic solvent added in step (b) is C4 to C 12 It is a linear or branched alcohol, preferably a C4 to C8 linear or branched alcohol. Advantageously, the organic solvent is provided as a biological source.

[0187] Advantageously, the organic solvent is selected from the group consisting of n-butanol, sec-butanol, isobutanol, and any mixture thereof, C4 to C 12 It is a linear or branched alcohol, more specifically n-butanol.

[0188] C4 to C 12Unlike esters such as ethyl or isopropyl acetate or certain ketones (specifically, acetone), alcohols have the advantage of not decomposing during recycling operations. Additionally, the presence of residues in the recycled solvent does not cause any implementation problems. In conclusion, this type of solvent facilitates the recycling of solvents at an industrial level.

[0189] Step (c) consists of the recovery of the organic phase obtained in step (a).

[0190] It is possible to repeat step (b) on the organic phase obtained from the previous iteration of step (b). The new organic phase obtained in this way is then recovered (repeated step (c)) and combined with the one generated from the previous iteration of step (b).

[0191] Accordingly, in the modification process, step (d) consists of repeating step (b) several times and step (d') concentrating the combination of organic phases recovered from the subsequent step (c).

[0192] In some embodiments, the process may include an additional step (e) of drying the lauson concentrate extract obtained from step (d). At the end of step (e), the obtained lauson concentrate extract is a dried extract.

[0193] The drying step (e) may be carried out according to methods widely known to those skilled in the art. Specifically, the drying step may be carried out by a pallet dryer, vacuum drying, atomization, microwave, zeodration, or freeze-drying.

[0194] In some embodiments, the process may include a step (c') of adding a carrier between step (c) and step (d), and step (d) proceeds to the drying step (e). At the end of step (e), the obtained Lauson concentrated extract is a standardized dried extract.

[0195] According to some preferred embodiments, the process does not include any step of changing the pH of the aqueous solution or aqueous phase by adding an acid or a base.

[0196] According to some preferred embodiments, the process further includes a step of extracting pigment, also called a decolorization step.

[0197] The pigment extracted during the bleaching step is clearly chlorophyll. However, lauson is understood to be the pigment part that the bleaching step is intended to remove.

[0198] The pigment extraction step can be carried out using an organic solvent that clearly does not dissolve lauson well. Accordingly, the solubility of lauson in the organic solvent used in the decolorization step is less than 15% by weight at 25°C, clearly less than 10% by weight, and advantageously less than 5% by weight, and the percentage is expressed based on the total weight of lauson contained in the extract or solution undergoing the decolorization step.

[0199] Preferably, lauson is not soluble in the organic solvent used in the pigment extraction step.

[0200] Advantageously, the organic solvent is a saturated or unsaturated hydrocarbon. Specifically, the saturated hydrocarbon may be selected from pentane, hexane, heptane, nonane, decane, cyclohexane, and mixtures thereof. The unsaturated hydrocarbon may clearly be benzene.

[0201] Preferably, the extraction step of pigments such as chlorophyll is carried out using heptane.

[0202] The pigment extraction step performed using an organic solvent may consist of liquid-liquid or liquid-solid extraction.

[0203] When this is a liquid-liquid extraction, the above step is inserted between step (a) and step (b) of the disclosed process.

[0204] Advantageously, the decolorization step of liquid-liquid extraction using an organic solvent consists of the following four substeps:

[0205] (i) A step of adding the organic solvent to the aqueous solution obtained from step (a);

[0206] (ii) a stirring step of the solution obtained from step (i), wherein the stirring duration is 15 minutes to 2 hours, specifically 15 minutes to 1 hour, and typically about 30 minutes;

[0207] (iii) a step of emptying the mixture obtained from step (ii) until two distinct phases, namely a water-soluble phase and an organic phase, are obtained; and

[0208] (iv) Removal step of organic phase

[0209] Includes

[0210] Next, step (b) of the process is carried out on the aqueous solution produced from step (iii).

[0211] When this step is liquid-solid extraction, the process proceeds to the drying step (e). Liquid-solid extraction can be carried out according to methods widely known to those skilled in the art.

[0212] Alternatively, the decolorization step can be performed using supercritical CO2 with or without adding a co-solvent to the dry extract. Chlorophyll is captured by supercritical CO2. The residue is the decolorized dry extract.

[0213] Lausoniina Inermis Aerial part extract B of

[0214] The dye composition of the present invention comprises a second specific henna extract referred herein as “Extract B”. Extract A and Extract B are combined to provide a dye composition.

[0215] This extract B is characterized by a low lauson content.

[0216] Accordingly, extract B contains less than 0.6 wt% of lausone based on the weight of the dry extract, advantageously less than 0.5 wt% based on the total weight of the dry extract, more advantageously less than 0.4 wt%, for example, 0 wt% to 0.6 wt%, specifically 0.05 wt% to 0.6 wt%, more specifically 0.1 wt% to 0.5 wt%. Specifically 0.1 wt% to 0.4 wt%, more preferably about 0.2 wt%.

[0217] The lauson content can be determined according to the HPLC assay method described in the following example (Method 1).

[0218] Extract B contains phenolic compounds such as tannins, phloroglucinol derivatives, naphthoquinone derivatives, flavonoids, and combinations thereof.

[0219] Specifically, the phenol compound may be selected from gallic acid, coumaric acid, and / or heterosides of these compounds and combinations thereof, specifically gallic acid.

[0220] Specifically, phloroglucinol derivatives are selected from heterosides of these derivatives such as 2,3,4,6-tetrahydroxyacetophenone, 1,3,6,7-tetrahydroxyxanthone, phloroglucinone, myrciaphenone A, ralioside and / or polygoacetophenosside, and combinations thereof.

[0221] Specifically, naphthoquinone derivatives are selected from heterosides of such derivatives, such as isonaphthazarin and / or 1,2,4-trihydroxynaphthalene-1-O-glucoside, and combinations thereof.

[0222] Specifically, the flavonoid derivative is selected from luteolin and / or heterosides of such derivatives, such as luteolin-4'-O-glucoside, luteolin-7-O-glucoside, and combinations thereof.

[0223] In some embodiments, the phenolic compound of extract B is

[0224] - Tannin, specifically hydrolyzable tannin, more specifically garlic tannin;

[0225] - Galsan;

[0226] - Luteolin and their heterosides, specifically their glycosylated derivatives;

[0227] - Apigenin;

[0228] - 2,3,4,6-tetrahydroxyacetophenone; and

[0229] - 1,3,6,7-tetrahydroxyxantone

[0230] Includes

[0231] In some embodiments, the phenolic compound of extract B is

[0232] - Gallic acid, coumaric acid and / or heterosides of these derivatives and combinations thereof;

[0233] - Tannin, specifically garlic tannin;

[0234] - Phloroglucinol derivatives such as 2,3,4,6-tetrahydroxyacetophenone; and

[0235] - Flavonoid derivatives such as luteolin, apigenin, and / or heterosides of these derivatives, and combinations thereof

[0236] It is selected from a group consisting of.

[0237] In some embodiments, extract B is characterized by a luteolin content of 0.05% to 0.5% by weight, specifically 0.1% to 0.3% by weight, based on the total weight of the dried extract.

[0238] In some embodiments, extract B is characterized by an apigenin content of 0.01% to 0.75% by weight, specifically 0.05% to 0.5% by weight, based on the total weight of the dried extract.

[0239] In some embodiments, extract B is characterized by a 2,3,4,6-tetrahydroxyacetophenone content of 0.01% to 0.5% by weight, specifically 0.02% to 0.1% by weight, based on the total weight of the dried extract.

[0240] In some embodiments, extract B is characterized by a gallic acid content of 0.05% to 0.5% by weight, specifically 0.1% to 0.3% by weight, based on the total weight of the dried extract.

[0241] The quantitative amount of the phenolic compound contained in extract B is at least 10% by weight, specifically at least 15% by weight, based on the total weight of the dried extract. Specifically, extract B contains 10% to 35% by weight, advantageously 15% to 35% by weight, and more advantageously 15% to 30% by weight of the phenolic compound based on the total weight of the dried extract.

[0242] The content of phenolic compounds is expressed by referring to the content of pyrogallol (Method 4).

[0243] Extract B contains a large amount of sugar-type compounds, and based on the total weight of the dry extract, contains at least 60% by weight, advantageously at least 65% by weight, more advantageously at least 70% by weight, for example 60% to 80% by weight, specifically 70% to 75% by weight of sugar compounds including polysaccharides.

[0244] Sugar compounds may further include monosaccharides, disaccharides, and combinations thereof. Specifically, polysaccharides are dominant by weight, i.e., typically constitute 50% by weight or more, advantageously 60% by weight or more, more advantageously 80% by weight or more, and much more advantageously 90% by weight or more of all sugars present in the extract.

[0245] Specifically, extract B may include mucilage as a polysaccharide.

[0246] Mucilage is a plant-based substance composed of polysaccharides or proteoglycans that swells upon contact with water and sometimes has a sticky, viscous consistency similar to gelatin.

[0247] Mucilages are compounds with a large, somewhat branched polymeric structure composed of various different sugar units or uronic acid units (uronic acid is a carboxylic acid derived from sugar). They are highly hydrophilic and can form gels by trapping water (and other molecules) in cage-like structures.

[0248] The sugar compound content can be determined by a calorimetric assay using dinitrosalicylic acid (Method 5).

[0249] Extract B may additionally contain organic acid(s). The content of the organic acid(s) may be at least 2% by weight, advantageously at least 3% by weight, advantageously at least 4% by weight, for example, 2% to 8% by weight of organic acid(s), specifically 4% to 8% by weight, based on the total weight of the dried extract.

[0250] The organic acid of extract B clearly comprises a hydroxyl acid, that is, a hydrocarbon compound having at least one carboxylic acid -COOH function and at least one alcohol -OH function, and advantageously at least one alcohol function is present at the alpha position of the carboxylic acid function (i.e., held by a carbon atom adjacent to the carbon atom having the carboxylic acid function). The organic acid of extract B, specifically the carboxylic acid, is an alkyl chain having 4 to 8 carbon atoms, advantageously linear, branched, or cyclic, and 4 to 6 carbon atoms. Specifically, the carboxylic acid is selected from the group consisting of succinic acid, ascorbic acid, malic acid, and combinations thereof. Organic acids such as malic acid, succinic acid, and ascorbic acid can be clearly identified by HPLC by known enzymatic or spectrophotometric methods available to those skilled in the art (Method 6).

[0251] These organic acids contribute to promoting the attachment of lauson to keratin fibers.

[0252] In addition, these organic acids impart a specific shine to the hair colored in this way and contribute to moisturizing the fibers.

[0253] In addition, lactone in extract B can generally be found in an amount of less than 10% by weight based on the total weight of the dry extract.

[0254] Extract B may contain protein compounds such as peptides, amino acids, or proteins in an amount ranging from 5% to 10% by weight based on the weight of the dry extract.

[0255] Extract B may be further characterized by one or more of the following advantageous features, advantageously all of them (percentages are expressed in weight based on the total weight of dry extract B):

[0256] - Extract B contains less than 0.6 wt%, advantageously less than 0.5 wt%, more advantageously less than 0.4 wt%, for example, 0 wt% to 0.6 wt% of lausone;

[0257] - Extract B contains at least 15% by weight of phenolic compounds, specifically tannins;

[0258] - Extract B advantageously contains gallic acid in an amount ranging from 0.1% to 0.3% by weight;

[0259] - Extract B advantageously contains 2,3,4,6-tetrahydroxyacetophenone in an amount ranging from 0.02 wt% to 0.1 wt%;

[0260] - Extract B advantageously contains luteolin in an amount ranging from 0.1% to 0.3% by weight;

[0261] - Extract B advantageously contains apigenin in an amount ranging from 0.05% by weight to 0.5% by weight;

[0262] - Extract B contains 1,3,6,7-tetrahydroxyxanthone;

[0263] - Extract B comprises 60% to 80% by weight of polysaccharides, predominantly mucilaginous, which are sugar compounds;

[0264] - Extract B contains 2% to 8% by weight of organic acids including malic acid, succinic acid, and ascorbic acid.

[0265] In some embodiments, extract B may be in a dry form, advantageously in a powder form with a particle size clearly less than 250 μm.

[0266] These extracts B combined with extract A are

[0267] - Expanding the color range to specifically approximate the color chart pursued in hair coloring;

[0268] - Improving the attachment of extract A to fibers, specifically keratin fibers;

[0269] - Keratin fibers, especially those that add shine to hair

[0270] Allows.

[0271] Process for obtaining extract B

[0272] As the applicant Lausonia Inermis A process was developed to obtain extract B from which it is possible to obtain an extract rich in compounds such as the phenolic compounds and sugar compounds described below, which exhibit a weak dyeing effect due to the low lauson content but can obtain dyeing effects and advantages for keratin fibers.

[0273] The present invention reflects an attempt to establish a synthetic route that is more environmentally friendly and allows the active ingredient thus obtained to be claimed to be natural.

[0274] Therefore, to your advantage Lausoniina Inermis Aerial part extract B is an extract obtained by water-soluble, water-alcoholic, or alcoholic extraction.

[0275] Henna extract B can be obtained from crushed leaves by water-soluble extraction at room temperature or high temperature, which may be in the range of 20°C to 180°C, under atmospheric pressure or supercritical pressure. After liquid-liquid separation, the filtrate is sterilized by a standard sterilization method (pasteurization, rapid pasteurization, etc.) and then dried and concentrated by a standard drying method known to those skilled in the art (vacuum drying, freeze-drying, microwave, etc.).

[0276] Advantageously, a water-miscible alcohol, specifically ethanol or ter-butanol, preferably ethanol, can be added prior to liquid-liquid separation to facilitate the filtration and dissolution of weakly polar compounds.

[0277] Extraction can be performed by different techniques, specifically so-called "eco-friendly" techniques, for example at atmospheric pressure (possibly, ultrasound, microwave, filtration, maceration, boiling, etc.) or high pressure, specifically using water in a subcritical state with or without an auxiliary solvent such as ethanol, at a temperature of 20°C to 250°C.

[0278] In some implementations, Laosonia Inermis Aerial part extract B of

[0279] (a) Laosonia Inermis A step of mixing the aerial portion, specifically the crushed leaves, specifically in water in which the plant / water w / v ratio is 1 / 2 to 1 / 10, advantageously 1 / 4 to 1 / 8;

[0280] (b) a step of stirring the mixture at a temperature in the range of 30℃ to 50℃;

[0281] (c) optionally, a step of adding an alcohol such as ethanol;

[0282] (d) a step of recovering the liquid phase by stirring; and

[0283] (e) A step of concentrating the liquid phase obtained in step (d) to obtain extract B.

[0284] It is an extract obtained by a method including

[0285] Specifically, the immersion in step (a) Laosonia Inermis The aerial portion is a mixture of leaves, branches, or both, which may be fresh or dried, preferably dried, and is preferably finely ground.

[0286] In a specific embodiment, a pectinase-type enzyme may be added in step (a).

[0287] Advantageously, stirring can be carried out by any method widely known to those skilled in the art.

[0288] Likewise, the water-soluble or water-alcoholic liquid phase can be recovered by any liquid-solid separation technique known to those skilled in the art, such as filtration, centrifugation, or decanting.

[0289] The duration of stirring is advantageously between 15 minutes and 2 hours, specifically between 15 minutes and 1 hour, and advantageously about 30 minutes.

[0290] The volume of alcohol added during step (b) is such that, in the applicable case, the resulting mixture contains 30% to 90% v / v alcohol, advantageously 30% to 80% v / v alcohol.

[0291] In addition to facilitating the extraction of hydrophilic compounds, alcohols such as ethanol sterilize mixtures and remove contaminants.

[0292] Additionally, alternatively, the conditional step (c) of adding an alcohol such as ethanol may be replaced by an alternative and equivalent decontamination and / or sterilization step known to those skilled in the art, such as heating using steam injection or microwave treatment, or any other suitable decontamination treatment.

[0293] In one embodiment, the method may include an additional step (f) of drying the extract obtained from step (e). At the end of step (f), the obtained extract B is a dried extract. The drying step (f) may be carried out according to methods widely known to those skilled in the art. Specifically, the drying step may be carried out by a paddle dryer, vacuum drying, atomization, microwave, zeodration, or freeze-drying.

[0294] Alternatively, extract B is

[0295] (a) Lausoniina Inermis In order for glycosylated lauson derivatives, such as henosides, initially present in the aerial portion of, to be partially or entirely hydrolyzed, Lausoniina Inermis A step of immersing the aerial portion of in water in a pH range of 4 to 8 to induce the production of an aqueous solution containing lauson;

[0296] (b) A step of adding an organic solvent to the aqueous solution obtained at the end of step (a) to induce the formation of an aqueous phase and an organic phase, wherein the organic solvent is C4 to C 12 A step selected from linear or branched alcohols, or a solvent having less than 10% by weight, advantageously less than 5% by weight, miscibility with water at 25°C;

[0297] (c') A step of recovering the water-soluble phase obtained at the end of step (b); and

[0298] (d') A step of concentrating the water-soluble phase recovered at the end of step (c') to obtain a low-lauson extract B.

[0299] It can be obtained depending on.

[0300] Therefore, extract B can be obtained by a method of carrying out steps (a) and (b) of the previously described method for obtaining extract A. However, the subsequently recovered phase is a water-soluble phase.

[0301] Advantageously, steps (a) and (b) are as previously described for the method of obtaining extract A.

[0302] Step (c') consists of water-soluble recovery and concentration to obtain extract B.

[0303] Additionally, the method may include a decontamination and / or sterilization step between step (c') and step (d') by any technique known to those skilled in the art, such as heating using steam injection or microwave treatment, or any other suitable decontamination treatment.

[0304] In one embodiment, the method may include an additional step (e') of drying the low-lauson extract obtained from step (d'). At the end of step (e'), the obtained low-lauson extract is a dried extract. The drying step (e') may be carried out according to methods widely known to those skilled in the art. Specifically, the drying step may be carried out by a paddle dryer, vacuum drying, atomization, microwave, zeodration, or freeze-drying.

[0305] A mixture of henna extract A and henna extract B

[0306] The henna extract A and henna extract B disclosed herein are mixed to provide the dye composition of the present invention. Surprisingly, the weight ratio of one to the other will have an effect on the obtained dye, and thus it is possible to access a wide color spectrum by changing this ratio. The two henna extracts A and B allow for obtaining a shade palette in both color and reflection (hue).

[0307] In some embodiments of the method of the present invention, extract A is mixed with extract B according to a B / A weight ratio of 1 or more. According to specific embodiments, the B / A weight ratio may be in the range of 1 to 10 / 1. In this invention, the inventors mean the ratio of dry extracts, and extract A is a standardized dry extract.

[0308] According to an alternative method, extract A may be mixed with extract B according to a B / A weight ratio of less than 1, advantageously in the range of 1 / 10 to 1. In this invention, the inventors mean the ratio of dry extracts, and extract A is a standardized dry extract. According to a specific embodiment, the B / A weight ratio may be in the range of 1 / 10 to 10 / 1, for example, 1 / 8 to 1 / 3. In this invention, the inventors mean the ratio of dry extracts, and extract A is a standardized dry extract.

[0309] Beneficial preparations

[0310] The method according to the present invention may also include the step of providing a beneficial agent, specifically a substrate of a dye, specifically an agent that promotes the attachment of the dye to cellulose fibers and / or keratin fibers.

[0311] The beneficial formulation is preferably in a dry form, advantageously in a powder form with a particle size clearly less than 250 μm.

[0312] In addition, beneficial preparations may be plant extracts or plant powders.

[0313] For example, cinnamon (neutral henna) can be used to promote the attachment of henna extract A to cellulose and / or keratin fibers.

[0314] For example, aloe vera, specifically the juice extract of aloe vera leaves, can be used as a natural mordant, that is, as a compound that promotes the adhesion of dyes. It can also nourish and moisturize keratin fibers and protect them from UV irradiation.

[0315] Additionally, aloe vera contains anthraquinones such as aloin and aloe-emodin, resins, tannins, and polysaccharides. Juice / gel can be extracted from aloe vera leaves that mainly contain water and polysaccharides such as pectin, hemicellulose, glucomannan, acemannan, and mannose derivatives. Such juice / gel may also contain amino acids, lipids, sterols such as lupeol and gampesterol, and enzymes.

[0316] Beneficial agents may be fructans such as inulin for their property of coating keratin fibers.

[0317] composition

[0318] The composition obtained according to the method of the present invention comprises henna extract A and henna extract B. This may further comprise beneficial agents as disclosed herein and / or one or more additional dyes as disclosed herein.

[0319] Advantageously, this may also include the addition of a limited number of dyes, no more than five additional dyes, advantageously three or fewer additional dyes, more advantageously two or fewer additional dyes, and much more advantageously one or fewer additional dyes. In an advantageous embodiment, the composition comprises only henna extract A and henna extract B as dyes.

[0320] Specifically, by combining two extracts derived from the same plant, namely henna, a wide color palette, specifically the entire color palette sought in both color and reflection of hair dyeing, can be obtained using such a limited number of dyes. This numerical limitation reduces the risk of intolerance and non-compliance and is more economical.

[0321] Furthermore, the combination according to the present invention

[0322] - It is natural, free of animal products, that is, based on dye active ingredients derived from plants, microorganisms, or microalgae;

[0323] - The exposure time for dyeing hair is advantageously short, less than 1 hour;

[0324] - Preferably, it is possible with a single application, including hair dyeing;

[0325] - Preferably organic and extremely plant-based;

[0326] - Hair dye maintains good color after multiple washes, including 10, or advantageously 15, hair washes.

[0327] A dye composition is provided.

[0328] In addition, hair dyes that avoid the use of hydrogen peroxide and alkaline chemicals are also sought.

[0329] Specifically, the advantageous combination is

[0330] - Henna extract A, specifically henna extract AN, and henna extract B;

[0331] - Henna extract A, specifically henna extract AN, henna extract B, and logwood powder;

[0332] - Henna extract A, specifically henna extract AN, henna extract B, and sorghum extract;

[0333] - Henna extract A, specifically henna extract AN, henna extract B, and sorghum powder;

[0334] - Henna extract A, specifically henna extract AN, henna extract B, and gardenia extract;

[0335] - Henna extract A, specifically henna extract AN, henna extract B, and gardenia powder;

[0336] - Henna extract A, specifically henna extract AN, henna extract B, and chlorophyllin;

[0337] - Henna extract A, specifically henna extract AN, henna extract B, and Indigofera plant extract; and

[0338] - Henna extract A, specifically henna extract AN, henna extract B, and Indigofera plant powder.

[0339] In a specific embodiment, the dye composition obtained according to the method of the present invention comprises 10% to 90% by weight, specifically 10% to 50% by weight or 50% to 90% by weight of a standardized henna extract AN based on the total weight of the composition. Including, the weight of the standardized extract is expressed as dry extract.

[0340] In a specific embodiment, the dye composition obtained according to the method of the present invention comprises extract B in an amount of 10% to 90% by weight, clearly 10% to 50% by weight or 50% to 90% by weight, based on the total weight of the composition. It includes, and the weight of extract B is expressed as dry extract.

[0341] The extract, specifically henna extract A, can be standardized, and a carrier will be found in the composition.

[0342] The carrier can be clearly selected from propanediol, pentanediol, glycerin, propylene glycol, methyl THF, and amyl alcohol.

[0343] When the dye composition according to the present invention is in powder form, the carrier is preferably selected from fructose, glucose, saccharose, maltodextrin, cellulose derivatives, starch (e.g., corn, wheat, or rice starch), sugar and polysaccharide derivatives such as agar, gum, and mucilage, and polyols such as mannitol, sorbitol, xylitol, etc. Specifically, the carrier is selected from fructose, maltodextrin, and starch, specifically rice starch.

[0344] When the dye composition according to the present invention is in powder form, a person skilled in the art can control the particle size by any method widely known to a person skilled in the art.

[0345] Specifically, the dye composition according to the present invention may be in the form of a powder with a particle size of less than 250 μm.

[0346] The composition may further comprise one or more acceptable excipients, specifically one or more cosmetically acceptable excipients suitable for application on human keratin fibers (as disclosed herein).

[0347] Advantageously, the composition does not have a stabilizer that stabilizes the lauson usually present in henna compositions.

[0348] Advantageously, the dye composition according to the present invention is free of additives or heavy metals, specifically synthetic dyes such as diaminotoluene and diaminobenzene, specifically the most commonly used PPD (para-phenylenediamine) [Wang et al. J. Environ. Anal. Toxicol. 2016, 6(3); Wang et al. J. Chromatogr. B 2011, 879: 1795-1801].

[0349] The dye composition according to the present invention may be a printing ink comprising extract A, extract B, and specifically oil and resin, as well as a suitable excipient selected from mixtures thereof.

[0350] Another dye C

[0351] The dye composition according to the present invention is Lausonia Inermis It may additionally include dye C derived from pigmented plants other than those, or from microorganisms or microalgae.

[0352] Accordingly, the method of the present invention may further include the step of providing dye C as disclosed herein.

[0353] Preferably, dye C is in a dry form, advantageously in a powder form with a particle size clearly less than 250 μm.

[0354] Dye C is Lausonia Inermis It may be a powder of pigmented plants, microorganisms, or microalgae that is not pigmented. In addition, dye C is Lausonia Inermis It may be an extract of pigmented plants, microorganisms, or microalgae that are not pigmented. The extract will almost always be a water-soluble, water-alcoholic, or alcoholic extract.

[0355] Advantageously, dye C is selected from Indigofera plants, plants that are sources of red pigment, plants that are sources of red or purple to black pigment, plants that are sources of yellow pigment, plants that are sources of red to blue-green pigment, plants that are sources of tannin, plants that are sources of chestnut pigment, and combinations thereof. Lausonia Inermis It comes from at least one pigmented plant, not just one.

[0356] Specifically, the Indigofera plant is a true indigo tree ( Indigopera Tintoria ), dye plant knotweed ( Polygonum tintorium or Persicaria tintoria ), dye plant woad ( Isatis tintoria L. ), Kuroupita giannensis (Cannonball Tree), Wild Indigo ( Baptistia Tintoria ), dye plant croton ( Crozophora tintoria ), dye plant oleander ( Laittia Tintoria ), Yoruba Indigo ( Philenoptera cyanesens = Roncocarpus cyanesense ), L. laxiflorus ( Roncocarpus laxiflorus ), Marsdenia Tintoria (Asclepias dacea), China Rainbell ( Strovilantes cucia or Strovilantes plassidipolius It is selected from ) and combinations thereof.

[0357] Advantageously, dye C contains indirubin and / or leucoindigo.

[0358] Advantageously, dye C is an extract of indigo leaves, specifically a water-soluble, water-alcoholic, or alcoholic extract of indigo leaves.

[0359] Advantageously, dye C is an extract of the dye plant knotweed leaves, specifically a water-soluble, water-alcoholic, or alcoholic extract of the dye plant knotweed leaves.

[0360] Advantageously, dye C is an extract of the dye plant woad leaf, specifically a water-soluble, water-alcoholic or alcoholic extract, or powder of the dye plant woad leaf.

[0361] Advantageously, dye C is Kuroupita giannensis Extracts of flowers and / or fruits, specifically Kuroupita giannensis It is a water-soluble, water-alcoholic, or alcoholic extract or powder of flowers and / or fruits.

[0362] Advantageously, dye C is an extract of the whole wild indigo plant, specifically a water-soluble, water-alcoholic, or alcoholic extract of the whole wild indigo plant, or a powder.

[0363] Advantageously, dye C is an extract of the entire dye plant croton, specifically a water-soluble, water-alcoholic or alcoholic extract of the entire dye plant croton, or a powder.

[0364] Advantageously, dye C is an extract of the entire dye plant oleander, specifically a water-soluble, water-alcoholic, or alcoholic extract of the entire dye plant oleander, or a powder.

[0365] Advantageously, dye C is an extract of Yoruba indigo leaves, specifically a water-soluble, water-alcoholic, or alcoholic extract of Yoruba indigo leaves, or a powder.

[0366] Advantageously, dye C is L. laxiflorus Leaf extract, specifically L. laxiflorus It is a water-soluble, water-alcoholic, or alcoholic extract of the leaves, or a powder.

[0367] Advantageously, dye C is Marsdenia Tintoria Extracts from the whole plant, specifically Marsdenia Tintoria It is a water-soluble, water-alcoholic, or alcoholic extract, or powder of the whole plant.

[0368] Advantageously, dye C is an extract of the Chinese reed bell plant, specifically a water-soluble, water-alcoholic or alcoholic extract of the Chinese reed bell plant, or a powder.

[0369] Advantageously, dye C is derived from at least one color-producing plant that is a source of red pigment. Specifically, the plant that is a source of red pigment is selected from sorghum, hibiscus, and combinations thereof.

[0370] Advantageously, dye C contains anthocyanin.

[0371] Advantageously, dye C is a water-soluble extract or water-alcohol extract of an aerial part of sorghum, specifically the stem, or a powder of an aerial part of sorghum, specifically the stem. In the case of the extract, the extraction solvent, advantageously a water-soluble or water-alcohol solvent, is advantageously acidic in pH, advantageously less than pH 6. In the case of the water-alcohol extract, the alcohol is advantageously miscible with water, such as ethanol.

[0372] Advantageously, dye C is a water-soluble extract or water-alcohol extract of hibiscus flowers, specifically dried flowers (carcades), or a powder of hibiscus flowers, specifically dried flowers (carcades). In the case of the extract, the extraction solvent, advantageously a water-soluble or water-alcohol solvent, is advantageously acidic pH, advantageously pH less than 6. In the case of the water-alcohol extract, the alcohol is advantageously miscible with water, such as ethanol.

[0373] Advantageously, dye C is derived from at least one color-producing plant that is a source of red or purple to zesty pigments. Specifically, the plant that is a source of red or purple to zesty pigments is logwood.

[0374] Advantageously, dye C is a water-soluble or water-alcoholic extract of logwood, specifically heartwood, or a powder of logwood, specifically heartwood. In the case of a water-alcoholic extract, the alcohol is advantageously miscible with water, such as ethanol.

[0375] Advantageously, dye C is derived from at least one color-producing plant that is a source of yellow pigment. Specifically, the source of yellow pigment is selected from gardenia, turmeric, saffron, birch, chamomile, reseda, and combinations thereof.

[0376] Advantageously, dye C contains crocin.

[0377] Advantageously, dye C is a water-soluble extract or water-alcoholic extract of gardenia flowers, or a powder of gardenia flowers. Such dye C may be extracted from gardenia as described in International Patent Application No. WO2018162760. Specifically, the gardenia extract or powder contains a crosin fraction in an amount of 0.1% to 10% by weight, preferably 1% to 5% by weight, based on the total weight of the dry extract or dry powder.

[0378] The gardenia extract may be a fluid, water-soluble or water-alcoholic extract, or a dry extract. Specifically, it is a water-soluble extract. The fluid gardenia extract, more specifically the water-soluble or water-alcoholic gardenia extract, is obtained after extraction and liquid-liquid separation and may be in the form of a liquid fraction (somewhat viscous) comprising 20% ​​to 60% of the dry extract, more specifically 30% to 50% of the dry extract, and much more specifically approximately 40% of the dry extract in a water-soluble or water-alcoholic solvent. Additionally, the extract may be in the form of a dry extract once the water-soluble or water-alcoholic solvent evaporates from the fluid extract. Such extracts are typically powdered and have an average particle size of 0.1 μm to 250 μm, specifically 1 μm to 250 μm.

[0379] Advantageously, dye C is a water-soluble extract or water-alcohol extract of turmeric rhizome, or a powder of turmeric rhizome. In the case of the water-alcohol extract, the alcohol is advantageously miscible with water, such as ethanol.

[0380] Advantageously, dye C is a water-soluble extract or an aqueous alcoholic extract of a saffron fragment, or a powder of a saffron fragment. In the case of an aqueous alcoholic extract, the alcohol is advantageously miscible with water, such as ethanol.

[0381] Advantageously, dye C is a water-soluble extract or a water-alcohol extract of birch leaves, or a powder of birch leaves. In the case of the water-alcohol extract, the alcohol is advantageously miscible with water, such as ethanol.

[0382] Advantageously, dye C is a water-soluble or water-alcohol extract of chamomile flowers, particularly the novel variety, or a powder of chamomile flowers, particularly the novel variety. In the case of the water-alcohol extract, the alcohol is advantageously miscible with water, such as ethanol.

[0383] Advantageously, dye C is a water-soluble extract or an aqueous alcoholic extract of Leseda root, or a powder of Leseda root. In the case of the aqueous alcoholic extract, the alcohol is advantageously miscible with water, such as ethanol.

[0384] Advantageously, dye C is derived from at least one color-producing plant that is a source of greenish-blue pigment. Specifically, the source plant of the greenish-blue pigment is selected from elderberry, blueberry, chokeberry, and combinations thereof.

[0385] Advantageously, dye C is a water-soluble extract or a water-alcohol extract of elderberry fruit, or a powder of elderberry fruit. In the case of the water-alcohol extract, the alcohol is advantageously miscible with water, such as ethanol.

[0386] Advantageously, dye C is a water-soluble extract or a water-alcohol extract of blueberry fruit, or a powder of blueberry fruit. In the case of the water-alcohol extract, the alcohol is advantageously miscible with water, such as ethanol.

[0387] Advantageously, dye C is a water-soluble extract or water-alcohol extract of chokeberry fruit, or a powder of chokeberry fruit. In the case of the water-alcohol extract, the alcohol is advantageously miscible with water, such as ethanol.

[0388] Advantageously, dye C is derived from at least one color-producing plant that is a source of tannins. Specifically, the tannin-producing plant is chestnut, Emblica Officinalis It is selected from , pomegranate and combinations thereof.

[0389] In this source, tannin plants are sought to specifically dull the color to gray or dark chestnut.

[0390] Advantageously, dye C contains tannin.

[0391] Advantageously, dye C is a water-soluble extract or a water-alcohol extract of chestnut, or a powder of chestnut. In the case of the water-alcohol extract, the alcohol is advantageously miscible with water, such as ethanol.

[0392] Advantageously, dye C is Emblica Officinalis Water-soluble extract or water-alcoholic extract of the fruit, or Emblica Officinalis It is a powder. In the case of an aqueous alcohol extract, the alcohol is advantageously miscible with water, such as ethanol.

[0393] Advantageously, dye C is a water-soluble extract or water-alcohol extract of pomegranate fruit, particularly the peel, or a powder of pomegranate fruit, particularly the peel. In the case of the water-alcohol extract, the alcohol is advantageously miscible with water, such as ethanol.

[0394] Advantageously, dye C is derived from at least one colorimetric plant that is a source of chestnut shades. Specifically, the plant that is the source of the chestnut pigment is a rhapontic.

[0395] Advantageously, dye C is a water-soluble extract or water-alcoholic extract of Lapontic root, or powder of Lapontic root ( Leum raponticum It is root powder.

[0396] All extracts and powders named above may bear an "organic" label, meaning they do not involve chemical synthesis steps and are obtained by environmentally responsible methods. They may also be referred to as "extreme plant-based."

[0397] In addition, the present invention provides uses for extracts obtained by semi-synthetic or synthetic methods.

[0398] Specifically, dye C could be chlorophyllin. Chlorophyllin is a source of green pigment.

[0399] Chlorophyllin can be obtained by extraction according to a semi-synthetic method involving a chlorophyll saponification step.

[0400] Chlorophyll-enriched plants can be clearly selected from alfalfa, white mulberry, nettle, algae, and combinations thereof.

[0401] Chlorophyll can be extracted from the aerial portion of alfalfa, for example, using organic solvents such as acetone, alcohol, alkanes (hexane or heptane), or supercritical CO2.

[0402] Chlorophyll can be extracted from the aerial parts of white mulberries, for example, using organic solvents such as acetone, alcohol, alkanes (hexane or heptane), or supercritical CO2.

[0403] Chlorophyll can be extracted from the aerial parts of nettle, for example, using organic solvents such as acetone, alcohol, alkanes (hexane or heptane), or supercritical CO2.

[0404] Chlorophyll can be extracted, for example, from the aerial portion of algal thallus using organic solvents such as acetone, alcohol, alkanes (hexane or heptane), or supercritical CO2.

[0405] The composition may contain at least 5% by weight of dye C based on the dry weight of the composition.

[0406] Cosmetic composition

[0407] The composition obtained by the method of the present invention is preferably a cosmetic composition. It can be formulated to be administered via an external local route.

[0408] Cosmetic compositions may be formulated into various forms of products suitable for topical administration, such as creams, emulsions, milks, ointments, lotions, oils, water-soluble or water-alcoholic or glycolic solutions, powders, sprays, shampoos, varnishes, or any other products for external application.

[0409] A cosmetic composition for dyeing advantageously comprises at least one cosmetically acceptable excipient.

[0410] Clearly, the cosmetic compositions of the present invention may also include cosmetically acceptable excipients known to those skilled in the art, selected from surfactants, texture and / or exfoliating agents, preservatives, perfumes, dyes, chemical or mineral UV filters, moisturizing agents, mineral water, pH correctors, etc. Those skilled in the art know how to adapt the formulation of the compositions according to the present invention using general information.

[0411] Specifically, the composition may advantageously comprise at least one acidity correcting agent selected from organic acids, specifically citric acid, acetic acid, carbonates, and bicarbonates, specifically sodium, calcium, or potassium bicarbonates.

[0412] Specifically, the composition may advantageously comprise at least one texture and / or peeling agent selected from polysaccharides such as maltodextrin, fructans such as inulin, bamboo silica cellulose, guar gum, xanthan gum, alginate, carrageenan, locust bean gum, gum arabic, acacia gum, Konjac, and pectin, as well as combinations thereof, and advantageously the composition comprises xanthan gum or a xanthan gum-acacia gum combination. The cellulose may clearly be a cellulose ether such as carboxymethylcellulose or hydroxypropyl methylcellulose.

[0413] Kit or combination product

[0414] The present invention also

[0415] Lausoniina Inermis A component (X) comprising a combination of aerial part extract A and extract B, and a component (Y) comprising at least one cosmetically acceptable excipient

[0416] It relates to a kit or combination product containing

[0417] These excipients are defined as previously for cosmetic compositions and, specifically, may be selected from the group comprising texture and / or peeling agents, acidity correctors, and mixtures thereof.

[0418] Advantageously, the component (Y) is a hair care product selected from the group including shampoos, conditioners, hair balms, hair creams, etc.

[0419] The component (Y) is advantageously in a dry form, clearly a powder.

[0420] Method and Use

[0421] The present invention also specifically relates to the use of a composition obtained according to the method of the present invention for cosmetic dyeing of keratin fibers in humans. In this case, a standardized henna extract AN is preferably used.

[0422] Although the above composition specifically contains a limited number of dyes derived from a single plant, it has been effectively observed that it can nevertheless cover the entire range of colors sought for hair dyes, regardless of pigment adjustment or permanent. The composition of the two henna extracts A and B allows for the acquisition of a shade palette in both color and reflection (tone). Additionally, the dye can be applied more effectively to gray hair.

[0423] Another advantage of the method and composition according to the present invention is that the color obtained on keratin fibers, such as hair, is clearly maintained despite repeated washing.

[0424] Accordingly, advantageously, the dyed keratin fibers do not exhibit a reduction of 8 units or more, advantageously 6 units or more, more advantageously 5 units or more, more even more advantageously 4 units or more, much more advantageously 3 units or more of gloss following 10, advantageously 15, dye-post-wash cycles, and according to the protocol described in the examples, the gloss is dE *It is evaluated by measuring parameters.

[0425] Another advantage of the present invention and the composition according to the present invention is that dyeing is advantageously achieved with a short exposure time of less than one hour for hair dyeing. In addition, hair dyeing can be achieved with a single application.

[0426] In addition, the present invention relates to a cosmetic method for dyeing keratin fibers, comprising the step of applying a water-soluble composition containing a composition according to the present invention onto keratin fibers and optionally proceeding with rinsing thereafter.

[0427] Specifically, clearly, a cosmetic method for dyeing human keratin fibers

[0428] (a) a step of providing a composition according to the present invention specifically in a dry form, clearly in a powder form;

[0429] (b) a step of preparing a water-soluble composition by adding and mixing water, specifically water, to the powder of step (a) at a temperature of 20°C to 98°C;

[0430] (c) a step of applying to keratin fibers and optionally treating the fibers while heating;

[0431] (d) rinsing step; and

[0432] (e) a step that optionally repeats steps (c) and (d).

[0433] Includes

[0434] Advantageously, steps (c) and (d) are not repeated.

[0435] It is observed that a small amount of the composition according to the present invention may be sufficient to dye adult hair with a small amount of water. Traditionally, for natural dyes containing plant powder or extract, it is recommended to mix at least 100g of powder with at least 300g of water, which results in a very thick "compress" that is inconvenient to handle and apply.

[0436] According to the present invention, during step (a), the powder of the composition according to the present invention is provided in an amount of less than 50 g, more advantageously less than 30 g, more advantageously less than 25 g, for example, 15 g to 30 g, advantageously 15 g to 25 g, more advantageously about 20 g.

[0437] During step (b), water is added in an amount sufficient to advantageously produce 100 g to 150 g of composition.

[0438] The water added can be room temperature water or hot water (hot tap water). The temperature of the hot water can be at least 50°C, which is easily obtained from a teapot, advantageously at least 70°C, and even at least 90°C.

[0439] Therefore, 100 g to 150 g of a water-soluble composition is sufficient to obtain a product that can be applied to the hair. The obtained composition is a convenient formulation, unlike the very thick and uncomfortable "compress" of known natural dyes.

[0440] The application step may have an exposure time step prior to the rinsing step, which has already been used for chemical hair dyeing. Specifically, the exposure time step also includes a heating step at a temperature specifically included in 25°C to 65°C, advantageously 30°C to 60°C, specifically 55°C, or specifically 35°C. Alternatively, the exposure time step may be performed at room temperature in the range of 20°C to 30°C without additional heat input and without such a heating step.

[0441] Advantageously, the exposure time is short, that is, less than 1 hour, preferably less than 45 minutes.

[0442] Advantageously, the coating step (c) is performed at a temperature included in 20°C to 55°C for a time included in 15 minutes to 1 hour, more advantageously in 15 minutes to 45 minutes.

[0443] The application step (c) can be performed on dry or wet keratin fiber strands.

[0444] In one embodiment, the dye is a color-adjusting dye.

[0445] Specifically, the dye is a gold dye having reflections and shades that can change from a warm copper color to a cool gold / chestnut color, especially on blonde hair. Advantageously, in this change, the exposure time will be less than 1 hour, preferably less than 45 minutes.

[0446] Specifically, the dye is a dark gold dye having reflections and shades that can change from warm copper to cool gold / chestnut, particularly on reddish-blonde or dark blonde. Advantageously, in this change, the exposure time will be less than 1 hour, preferably less than 45 minutes.

[0447] Alternatively, a cosmetic method for clearly dyeing human keratin fibers

[0448] (a.1) A step of providing extract A according to the present invention, specifically in a dry form, clearly in a powder form, with at least one cosmetically acceptable excipient as previously defined, optionally together with at least one cosmetically acceptable excipient;

[0449] (b.1) A step of preparing a water-soluble composition by adding and mixing a water-soluble composition, particularly water, to the powder of step (a.1) at a temperature of 20°C to 98°C;

[0450] (c.1) A step of applying the composition of step (b.1) onto keratin fibers and optionally treating the fibers while heating them;

[0451] (d.1) Rinsing step;

[0452] (a.2) A step of providing extract B according to the present invention, specifically in a dry form, clearly in a powder form, with at least one cosmetically acceptable excipient as previously defined;

[0453] (b.2) A step of preparing a water-soluble composition by adding and mixing a water-soluble composition, particularly water, to the powder of step (a.2) at a temperature of 20°C to 98°C;

[0454] (c.2) A step of applying the composition of step (b.2) onto keratin fibers and optionally treating the fibers while heating them;

[0455] (d.2) Rinse step; and

[0456] (e) Optionally, but not desirablely, repeating steps (c.1) and (d.1) and / or steps (c.2) and (d.2).

[0457] Includes

[0458] Alternatively, a cosmetic method for clearly dyeing human keratin fibers

[0459] (a.1) A step of providing extract B according to the present invention, specifically in a dry form, clearly in a powder form, with at least one cosmetically acceptable excipient as previously defined, optionally together with at least one cosmetically acceptable excipient;

[0460] (b.1) A step of preparing a water-soluble composition by adding and mixing a water-soluble composition, particularly water, to the powder of step (a.1) at a temperature of 20°C to 98°C;

[0461] (c.1) A step of applying the composition of step (b.1) onto keratin fibers and optionally treating the fibers while heating them;

[0462] (d.1) Rinsing step;

[0463] (a.2) A step of providing extract A according to the present invention, specifically in a dry form, clearly in a powder form, with at least one cosmetically acceptable excipient as previously defined;

[0464] (b.2) A step of preparing a water-soluble composition by adding and mixing a water-soluble composition, particularly water, to the powder of step (a.2) at a temperature of 20°C to 98°C;

[0465] (c.2) A step of applying the composition of step (b.2) onto keratin fibers and optionally treating the fibers while heating them;

[0466] (d.2) Rinse step; and

[0467] (e) Optionally, but not desirablely, repeating steps (c.1) and (d.1) and / or steps (c.2) and (d.2).

[0468] Includes

[0469] These alternative steps are implemented with necessary adjustments in terms of sequence, as previously explained in favor.

[0470] In either step (a.1) or step (a.2), dye C according to the present invention may also be added, and alternatively or additionally, a series of steps (a.3) to (c.3) may be provided with a dye similar to steps (a.1) to (c.1) but not dye C.

[0471] In addition, the present invention relates to a method of tattooing the skin.

[0472] In addition, the present invention relates to a plant-based ink of a dye composition obtained according to the present invention, for use in printing, for example, on paper or cardboard.

[0473] In addition, the present invention aims to provide a fabric dye or furniture colorant comprising a composition according to the present invention.

[0474] Additionally, these dyes or colorants may include one or more additional dye(s) or pigment(s).

[0475] Additionally, the dye or colorant according to the present invention may include any adjuvant known to those skilled in the art who know the method of adapting the dye or colorant formulation according to the present invention using general information.

[0476] In addition, the present invention relates to the use of such dyes or colorants for dyeing fabric fibers or coloring wood fibers.

[0477] Accordingly, the present invention also aims to use the composition according to the present invention for coloring cellulose materials such as fabric fibers, wood fibers, etc.

[0478] The following examples illustrate the present invention. Brief explanation of the drawing

[0479] Figure 1 shows the normalized UHPLC-UV chromatogram of the extract (sample E2) obtained by the process according to Example 1.2. Figure 2 shows the same chromatogram as Figure 1. The filled peaks correspond to the peaks that can be observed in Figure 1, while the solid lines correspond to an enlargement of the chromatogram. Figures 3a, 3b, 3c, 3d, and 3e show lauson, luteolin, apigenin, and para isolated from sample E2. - Shows the UV spectra of coumaric acid and 2,3,4,6-tetrahydroxyacetophenone. Figure 4 shows the normalized UHPLC-UV chromatogram of the extract obtained by the process according to Example 1.4. Figure 5 shows the color difference dE after 10 washes for product I1 (vertical line) or control T1 (horizontal line). * It represents. Specific details for implementing the invention

[0480] Specialization

[0481] (A) Structural Analysis

[0482] Materials and Methods

[0483] Chromatographic separation was performed on a Waters Aquiti UHPLC system equipped with a quaternary pump, automatic sample injector, online degassing unit, automatic temperature-controlled column oven, and DAD detector (200 nm to 500 nm). Vanguard TM An Aquiti UPLC BEH blocking RP18 column (100 mm × 2.1, 1.7 μm) equipped with a pre-column (5 mm × 2.1) was used at 35°C, and the flow rate was set to 0.4 mL / min. The mobile phase consisted of a concentration gradient system of (A) water containing 0.1% formic acid and (B) acetonitrile, and (C) methanol as a washing solvent: 2% to 100% B from 0 to 9 min; 100% B maintained from 9 to 9.55 min; 0% to 100% C from 9.55 to 9.70 min; 100% C maintained from 9.7 to 10.2 min; 0% to 100% B from 10.20 to 10.35 min; Maintain 100% B for 10.35 to 10.85 minutes; 0% to 98% A for 10.85 to 11 minutes; and continue 98% A to 2% for 1 minute to equilibrate the column.

[0484] Compounds were tested using high-performance mass spectrometry, 1D- and 2D-NMR experiments ( 1 H NMR, 13 It was confirmed by 3C NMR, DEPT, COSY, HMBC, HSQC.

[0485] (B) Quantitative Analysis: Experimental Conditions

[0486] Luteolin and apigenin were titrated by analytical HPLC using a C18 column (XBridge 100 C18; 3.5 mm, 150 mm × 4.6 mm) with gradient conditions of H2O / trifluoroacetic acid 0.1% (A) and acetonitrile / trifluoroacetic acid 0.1% (B) as eluents.

[0487] Gradient conditions : t0 min A 18%, B 82%; t1 min: A 18%, B 82%; 10 min: A 50%, B 50%; 10.1 min: A 18%, B 82%.

[0488] UV detection was performed at 340 nm for apigenin and 310 nm for luteolin. The flow rate was 1 mL / min and the temperature was 40℃. Pure luteolin, apigenin, and p-coumarin were used for calibration.

[0489] Example 1: Synthesis of Extract A

[0490] Example 1.1: Isopropyl acetate extract according to the present invention

[0491] 50 g of Lausonia Inermis Uncrushed leaves are extracted with 500 mL of water at 30 to 40°C for 30 minutes. 600 mL of isopropyl acetate is added to this solution. This is mixed for 30 minutes. After decanting, the upper isopropyl acetate phase (480 mL) is recovered, and the water-soluble phase is separated as it is practically free of lauson. The isopropyl acetate phase is filtered and then dried using a rotary evaporator. The residue is the dried henna extract.

[0492] The plant contains 1.5 g of lauson / 100 g of dried plant.

[0493] The isopropyl acetate upper phase contains 80.7% of the potential lauson present in plants.

[0494] The dried henna extract contains 30.2% by weight of lauson, that is, 71% by weight of lauson present in the plant.

[0495] Stability study: Sample stored at 25℃ and 60% relative humidity, protected from light:

[0496] TO: Lausone content = 30.2 wt% of Lausone based on the weight of the dry extract

[0497] T1 month: Lausone content = 29.7% by weight of Lausone based on the weight of the dry extract; no significant loss in the sense of the present invention.

[0498] Example 1.2: Isopropyl acetate extract No. 2 according to the present invention

[0499] 49.5 g of Lausonia Inermis Uncrushed leaves are extracted with 500 mL of water at 30 to 40°C for 30 minutes. 600 mL of isopropyl acetate is added to this solution. This is mixed for 30 minutes. After decanting, the upper isopropyl acetate phase is recovered, filtered over a Buchner (K900), and the residue is rinsed with 50 mL of isopropyl acetate. Next, the resulting solution is dried using a rotary evaporator. The residue is the dried henna extract (Sample E2).

[0500] The dried henna extract (sample E2) contains 30.9% by weight of lauson.

[0501] result

[0502] UHPLC-UV chromatogram

[0503] The obtained UHPLC-UV chromatogram is shown in FIGS. 1 and 2. The peak (solid line in FIG. 2) that can be observed on the magnified view of the chromatogram is associated with the following compound.

[0504]

[0505] UV spectrum

[0506] The UV spectra of the compounds corresponding to peaks 15, 20, 22, 10, and 5 are shown in Figs. 3a, 3b, 3c, 3d, and 3e, respectively.

[0507] (B) Quantitative analysis

[0508] Materials and Methods

[0509] Batch samples

[0510] - LP110: Henna extract AN, ethyl acetate extract standardized to maltodextrin - Industrial scale.

[0511] - ES310: Henna extract AN, ethyl acetate extract standardized to maltodextrin - laboratory scale.

[0512] - JQ137A: Henna extract AN, isopropyl acetate henna extract using fructose - laboratory scale.

[0513] In each of the above standardized extracts, the lauson is equivalent to 1.1% by weight.

[0514] result:

[0515]

[0516]

[0517] Example 1.3: Ethyl acetate standardized dry extract according to the present invention

[0518] 50 g of Lausonia Inermis Uncrushed leaves are extracted with 500 mL of water at 30 to 40°C for 30 minutes. 600 mL of ethyl acetate is added to this solution. This is mixed for 30 minutes. After decanting, the upper ethyl acetate phase is recovered, and the water-soluble phase is removed due to its very low lauson content.

[0519] The lauson content in ethyl acetate is determined by HPLC, and a sufficient amount of maltodextrin is added to obtain a mixture containing 1.3% by weight of lauson, and then freeze-dried.

[0520] The dried henna extract standardized with maltodextrin contains 1.1% by weight of lauson, i.e., an initial lauson content of 71% by weight in the plant.

[0521] Example 1.4: n-butanol extract according to the present invention

[0522] 50 g of Lausonia Inermis Uncrushed leaves are extracted with 6 times the volume of water at 30 to 40°C for 30 minutes. 6 times the volume of n-butanol is added to this solution at room temperature.

[0523] This mixture is stirred for 30 minutes. After decanting, the upper n-butanol phase is recovered, and the water-soluble phase is removed as it is practically free of lauson. The organic phase is passed over water to concentrate it.

[0524] The lausone content in n-butanol is determined by HPLC. A sufficient amount of maltodextrin is added to obtain a mixture containing 1.1% to 1.3% by weight of lausone.

[0525] The concentrate is dried to obtain powder.

[0526] result

[0527] UHPLC-UV chromatogram

[0528] The obtained UHPLC-UV chromatogram is shown in Fig. 5. The observable peaks were associated with the following compounds.

[0529]

[0530] The presence of glycosylated luteolin, specifically luteolin-6-C-neohesperidoside and coumaric acid, is noted.

[0531] Example 2: Synthesis of Extract B

[0532] Example 2.1:

[0533] Crushed Lausonia InermisThe leaves are introduced into a 50 g reactor with 6 times the volume of water. The resulting paste is stirred at 50°C for 30 minutes. Next, 6 times the volume of ethanol is added to this mixture, i.e., to a final alcohol content of 80% v / v, and the mixture is then vigorously shaken for 30 minutes. The entire paste is filtered (over an AF15 filter), the aqueous filtrate is recovered, sterilized, and then concentrated by the evaporation of ethanol. Next, the aqueous concentrate is dried. The dried product corresponds to a dried henna extract (yield 54 wt%).

[0534] The extract obtained in this way (percentages are expressed as weight based on the total weight of the dry extract)

[0535] - Lauson 0.6 wt%;

[0536] - Sugar compounds: 69.9 wt% (total sugar content) (polysaccharide content 59.3 wt%);

[0537] - Apigenin 0.05 wt%;

[0538] - Luteolin 0.17 wt%

[0539] Includes

[0540] Example 2.2:

[0541] Crushed Lausonia Inermis The leaves are introduced into a 50 g reactor with 6 times the volume of water. The resulting paste is stirred at 50°C for 30 minutes. It is then vigorously stirred for an additional 30 minutes. The entire paste is filtered (over an AF15 filter), the aqueous alcohol filtrate is recovered, sterilized at 120°C for 20 minutes, and then concentrated. Next, the aqueous concentrate is dried. The dried product corresponds to a dried henna extract (yield 60 wt%).

[0542] The extract obtained in this way contains 0.4% by weight of lauson as a percentage based on the total weight of the dried extract.

[0543] Example 3: Comparison of characteristic compounds of Extract A and Extract B

[0544] The characteristic compounds of the extract obtained according to Example 1 or Example 2 are reported in the following table, and the percentages are expressed as weight based on the total weight of the dried extract.

[0545]

[0546] nd means not detected, and the compound was not detected during the analysis.

[0547] nm means unmeasured, and the compound was detected during the analysis but not measured.

[0548] Example 4: Evaluation of color retention on human natural gray hair strands after washing

[0549] Extract A according to the present invention (Example 1.2) is mixed with extract B according to the present invention (Example 2.2) in a B / A weight ratio of 1 / 1. This mixture is designated as Product I1. Conventional henna extract is also used as a control (finely ground Lausonia Inermis The leaves (< 250 μm). This powder is called product T1.

[0550] In each case, 10 g of powder was mixed with 40 g of water prior to application onto the hair strands. The two products, I1 and T1, were evaluated for the dye content in the hair after washing. All hair strands underwent up to 10 standard washes using a neutral shampoo.

[0551] For products I1 and T1, respectively, the color of five test hair strands of natural human gray hair, Color 10 (gray hair), was measured using a reflective calorimeter (CR400 chroma meter, Minolta, France). The color parameter, L, measured by this device * a * b * describes hair strand color. The evaluated parameter is L * a * b * Derivatives of, i.e., color difference (dE * )am.

[0552] [Mathematical Formula 1]

[0553]

[0554] L1 here * , a1 * , b1 * is the coordinate in the CIELAB color space established by the 1976 International Commission on the lighting of the first color to be compared, and L2 * , a2 * , b2 * is the coordinate of the second color.

[0555] In this case, the "1" value is the Lab value of the dye strand before washing, and the "2" value is the value obtained after 10 washes.

[0556] Statistical studies determined that the color difference using combination I1 according to the present invention was significantly smaller than that of the control group T1 ( * p < 0,05).

[0557] The results are reported in Figure 5.

[0558] Method 1: Detection of Lauson by HPLC

[0559] This method can be applied to the following.

[0560] A. Detection of Lauson in Extracts

[0561] B. Laosonia Inermis Obtained by acid hydrolysis in the aerial part of Existing in free form or in the form of glycosylated lauson derivatives Total Lauson test and quantification of lauson potential in plants accordingly.

[0562] C. Test for Lauson formed by enzymes

[0563] reagent

[0564] Lausone > 97% (HPLC) Sigma Product Number: H46805

[0565] Dichloromethane for analysis

[0566] Sulfuric acid for analysis.

[0567] Methanol for analysis

[0568] HPLC grade water

[0569] HPLC-grade acetonitrile

[0570] HPLC-grade trifluoroacetic acid

[0571] HPLC conditions

[0572] - Column: XBridge C18, 3.5 μm, 4.6 × 150 mm Waters

[0573] Blast furnace: 40℃

[0574] - Solvent: SA: 0.1% trifluoroacetic acid in water

[0575] SB: 0.1% trifluoroacetic acid in acetonitrile

[0576] - Gradient: T 0 min 40% SA; T 1 min 40% SA; T 10 min 5% SA; T 11 min 5% SA; T 11.1 min 40% SA.

[0577] - Wavelength: λ = 278 nm.

[0578] - Flow rate: 1 mL / min

[0579] - Injection: 10 μL.

[0580] Sample preparation

[0581] In the case of whole or coarsely ground leaves,

[0582] 50 g of leaves are crushed and then filtered through a 0.355 μm sieve.

[0583] In the case of leaf powder,

[0584] Use 50 g of leaf powder equally.

[0585] Preparation of the solution

[0586] * Control group solution

[0587] 0.3 mg / mL of Lauson solution in 1 / 1 methanol / ethanol. Dilute to 1 / 10, 1 / 20, and 1 / 100 in 1 / 1 methanol / ethanol.

[0588] * Test solution

[0589] - Test solution A (Testing for Lausone present in the extract)

[0590] Dissolve 50 mg of the extract in 100 mL of 1 / 1 methanol / ethanol. Dissolve using ultrasound, filter over an acrodisk GFGHP. Inject 10 μL.

[0591] - Test solution B (Total Lauson Test)

[0592] 80 mg of leaf powder is introduced into a volumetric flask. 50 mL of 2N H2SO4 is added. Heat to 97°C for 30 minutes. Add methanol to make 100 mL. Filter the solution over an Acrodisk GF GHP 0.45 μm filter. Inject 10 μL of the filtrate.

[0593] - Test solution C (Test for Lauson formed by enzymes)

[0594] 80 mg of leaf powder is introduced into a volumetric flask. 50 mL of demineralized water is added. It is placed in an ultrasonic bath at 30 to 40°C for 30 minutes. Methanol is added to make 100 mL. The solution is filtered over an Acrodisk GF GHP 0.45 μm filter. 10 μL of the filtrate is injected.

[0595] result

[0596] Using the regression line calculated with the control solution

[0597] A. Lausone content of the extract,

[0598] B. Total lauson content, and / or

[0599] C. Content of lauson formed by the enzyme

[0600] Determines.

[0601] Method 2: Detection of nitrogen-containing compounds (amino acids, proteins)

[0602] Free amino acids and proteins can be detected by ninhydrin spectrophotometry before and after hydrolysis. The results are expressed as a percentage of amino acids based on asparagine.

[0603] Test of total protein and amino acids

[0604] principle

[0605] Calorimetric assay of amino acids using ninhydrin reagent after acid hydrolysis. The result is expressed as the percentage of total amino acids based on asparagine.

[0606] reagent

[0607] * Citrate buffer (pH = 5)

[0608] Dissolve 2.1 g of citric acid in 20 mL of water, add 20 mL of 1 N sodium hydroxide, and adjust the volume to 50 mL using water.

[0609] * Ninhydrin reagent

[0610] 0.08 g of tin (II) chloride (SnCl 2, Dissolve 2H2O in 50 mL of citrate buffer (pH = 5).

[0611] 2 g of ninhydrin is dissolved in 50 mL of ethylene glycol monomethyl ether (EGME).

[0612] Mix the two solutions.

[0613] 6 N hydrochloric acid

[0614] Dilute 1 / 2 of concentrated hydrochloric acid (36%).

[0615] * Diluent

[0616] Mix 100 mL of 1-propanol with 100 mL of water.

[0617] Preparation of solution

[0618] * Manufacturing of the correction range

[0619] Dissolve 17 mg of asparagine in 100 mL of water.

[0620] Preparation of test solution

[0621] Sample to be analyzed ( pe 1 Weigh 30 mg to 200 mg of extract in a rotary screw tube and add 2 mL of 6 N HCl.

[0622] Seal it and leave it at 110°C for approximately 16 hours.

[0623] Neutralize with 3 N sodium hydroxide (turns to methyl red), then add water to make a volume of 20 mL.

[0624] black

[0625]

[0626] Stir and leave in a water bath at 100°C for 20 minutes. Cool in an ice bath. Dilute to 10 mL.

[0627] The absorbance of different samples at 570 nm is measured in comparison to the blank sample.

[0628] calculate

[0629] Construct a calibration curve. From this, the total amino acid concentration expressed as asparagine in the test solution is (Q AAT Estimates the total amino acid content of the extract (T AAT ) is given by the following mathematical formula:

[0630]

[0631] Here, Q in mg / mL units AAT and mg units pe 1 .

[0632] Method 3: Gravimetric measurement of chlorophyll

[0633] The chlorophyll content in the extract can be evaluated by the weight obtained after washing the extract with heptane. 10 times the volume of methanol is added to the extract. After stirring for 15 minutes, the solution is filtered. The supernatant is dried to form a fraction containing chlorophyll.

[0634] Method 4: Spectrophotometric assay of phenol compounds

[0635] The content of phenolic compounds in the extract can be evaluated by spectrophotometry according to the method of European Pharmacopoeia, version 9.0, 2.8.14.

[0636] The solution to be tested is prepared by dissolving 25 mg of extract in 100 mL of water.

[0637] The content of phenolic compounds is expressed by reference to pyrogallol.

[0638] Method 5: Calorimetric verification of sugar compounds before and after hydrolysis

[0639] principle

[0640] Sugar compounds in dinitrosalicylic acid (DNS) are determined by calorimetry in comparison to glucose before and after hydrolysis. The result is expressed as a percentage of sugar compounds compared to glucose.

[0641] reagent

[0642] DNS Reagent: Dissolve 30 g of sodium and potassium ditartrate in 50 mL of water. Add 20 mL of 2 N sodium hydroxide. Dissolve 1 g of dinitrosalicylic acid (DNS) while heating gently. Adjust to 100 mL with water.

[0643] Preparation of solution

[0644] * Manufacturing of the correction range

[0645] Dissolve 5 mg of glucose in 10 mL of water.

[0646] * Preparation of hydrolyzed test solution (total sugar compounds)

[0647] About 1 g of extract ( pe 2 Weigh the amount of ). Add 1 mL of 4 N H2SO4. Heat under reflux for 2 hours. Neutralize with 1 N sodium hydroxide and transfer to a 20 mL volumetric flask. Adjust the volume to 20 mL with water.

[0648] * Preparation of unhydrolyzed test solution (free sugar compounds = monosaccharides)

[0649] Approximately 10 g of extract in a 20 mL volumetric flask ( pe 3 Weigh the ). Adjust the volume to 20 mL with water.

[0650] volume

[0651] Administer the solution according to the following table.

[0652]

[0653] After shaking, place in a water bath at 100°C for 5 minutes. Cool in an ice bath and adjust to 10 mL using water. Measure the absorbance of different samples at 570 nm in comparison to the blank sample.

[0654] calculate

[0655] Create a correction curve.

[0656] Total sugar compounds represented by glucose in the test solution (Q SRT Estimate the concentrations of ) and free sugars (QSRL). Total sugar compounds (T) of the extract SRT The inverse of ) is provided by the following mathematical formula:

[0657]

[0658] Here, Q in mg / mL units SRT and mg units pe 2 .

[0659] Free sugar compounds of the extract (TSRL The inverse of ) is provided by the following mathematical formula:

[0660]

[0661] Here, Q in mg / mL units SRL and mg units pe 3 .

[0662] Method 6: HPLC assay of organic acids

[0663] principle

[0664] HPLC assay of organic acids from plant extracts. The organic acids tested are succinic acid, malic acid, and ascorbic acid.

[0665] Chromatography system

[0666] - Column: Atlantis dc18 5 μm, 5 μm 250 × 4.6 mm Waters or equivalent;

[0667] - Temperature: 25℃;

[0668] - Mobile phase: Solvent A, 50 mM phosphate buffer, pH 2.8; Solvent B, acetonitrile;

[0669] - Gradient: T0 %A: 100%; 7.5 min %A: 100%; 15 min %A: 90%; 16 min %A: 50%; 23 min %A: 50%; 24 min %A: 100%; 40 min %A: 100%;

[0670] - Flow rate: 1 mL / min;

[0671] - λ = 200 at 400 nm (extracted at 214 nm);

[0672] - Injection volume: 5 μL.

[0673] Preparation of solution

[0674] Control solution: Weigh 10 mg of the control and dissolve it in 20 mL of purified water. Perform dilutions of 1 / 5, 1 / 10, and 1 / 20.

[0675] Test solution: Weigh 250 mg of the substance and analyze it in a 20 mL volumetric flask. Adjust with water and, if necessary, develop using ultrasound.

[0676] result

[0677] The chromatograms of the control and test solutions have several characteristic and matching peaks.

[0678] The residence time of the control group is

[0679] - Malsan: 5.5 minutes,

[0680] - Ascorbic acid: 11.7 minutes,

[0681] - Ascorbic acid: 11.7 minutes

[0682] am.

[0683] Create a calibration curve for each control group and estimate the quality of the sample.

Claims

Claim 1 A method for preparing a dye composition comprising: 7% to 60% by weight of lauson, and luteolin, apigenin, and 2,3,4,6-tetrahydroxyacetophenone, based on the total weight of the dried extract. Lausoniina Inermis ( Lawsonia inermis A step of providing an aerial fraction extract A of ), wherein the lausone is produced from the enzymatic hydrolysis of a glycosylated lausone derivative; and- based on the total weight of the dry extract, lausone less than 0.6 wt%, a phenolic compound at least 15 wt%, and a sugar compound including a polysaccharide at least 60 wt% including Lausoniina Inermis A method comprising: providing an aerial portion extract B of; mixing extract A and extract B; and obtaining a dye composition. Claim 2 delete Claim 3 In Article 1, the above Lausoniina Inermis A method in which the aerial partial extract A further comprises coumaric acid. Claim 4 In Article 1, the above Lausoniina Inermis A method in which the aerial portion extract A does not contain 2% by weight or more of protein, peptide, or amino acid based on the total weight of the dry extract. Claim 5 In claim 1, the dye composition is the Lausoniina Inermis Comprising aerial part extract A and a carrier Lausoniina Inermis A method comprising a standardized dry extract AN, wherein the standardized dry extract AN comprises 0.6% to 1.4% by weight of Lauson based on the total weight of the standardized dry extract. Claim 6 In Clause 5, the above Lausoniina Inermis A standardized dry extract AN comprises, based on the total weight of the dry extract: 0.05 wt% to 1.0 wt% of luteolin; 0.01 wt% to 0.5 wt% of apigenin; and 0.01 wt% to 1.0 wt% of 2,3,4,6-tetrahydroxyacetophenone. Claim 7 In Article 1, the above Lausoniina Inermis The aerial partial extract A of (a) above Lausoniina Inermis In order to enzymatically hydrolyze, in part or in whole, the glycosylated lauson derivative initially present in the aerial portion of, the Lausoniina Inermis (b) a step of immersing the aerial portion of in water with a pH range of 4 to 8 to provide an aqueous solution containing lauson; (b) a step of adding an organic solvent to the solution obtained from step (a) to provide an aqueous phase and an organic phase, wherein the organic solvent is C4 to C 12 A method obtained by a process comprising: a step selected from a linear or branched alcohol or a solvent having miscibility with water at less than 10 weight% at 25°C; (c) a step of recovering the organic phase obtained from step (b); and (d) a step of concentrating the organic phase recovered from step (c) to provide the extract A cited in claim 1. Claim 8 In claim 7, step (a) is under the condition that step (a) is carried out at a temperature in the range of 20°C to 60°C; under the condition that step (a) is carried out at a pH in the range of 5 to 7.5; under the condition that step (a) is carried out under stirring for 15 minutes to 2 hours; and under the condition that step (a) immerses the above Lausoniina Inermis A method performed according to at least one of the conditions in which the volume of water is 2 to 15 times greater than the weight of the air portion. Claim 9 A method according to claim 1, wherein the sugar compounds of the extract B further comprise monosaccharides, disaccharides, and combinations thereof. Claim 10 A method according to claim 1, wherein the extract B comprises 2% to 8% by weight of an organic acid based on the total weight of the dried extract B. Claim 11 The method according to claim 1, wherein the phenolic compound of extract B is selected from the group consisting of: gallic acid, coumaric acid and / or heterosides of these compounds and combinations thereof; tannins; phloroglucinol derivatives; and flavonoid derivatives. Claim 12 In claim 1, the extract B is Lausoniina Inermis A method that is a water-soluble, water-alcoholic, or alcoholic extract of Claim 13 A method according to claim 1, wherein the extract A is mixed with the extract B according to a B / A weight ratio of 1 or more, and the extract A is a standardized dry extract. Claim 14 A method according to claim 1, wherein the extract A is mixed with the extract B in a B / A weight ratio of less than 1, and the extract A is a standardized dry extract. Claim 15 A dye composition obtained by the method according to claim 1. Claim 16 A dye composition according to claim 15, further comprising one or more cosmetically acceptable excipients applicable to human keratin fibers. Claim 17 A dye composition used for cosmetic dyeing of human keratin fibers in claim 15. Claim 18 A cosmetic method for dyeing human keratin fibers, comprising: (a) a step of providing a dye composition according to claim 15 in powder form; (b) a step of preparing a water-soluble composition by adding and mixing a water-soluble composition and water at a temperature of 20°C to 98°C to the powder of step (a); (c) a step of applying to keratin fibers; and (d) a step of rinsing.

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