WO2023272610A1 - Dye kit - Google Patents

Dye kit Download PDF

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Publication number
WO2023272610A1
WO2023272610A1 PCT/CN2021/103696 CN2021103696W WO2023272610A1 WO 2023272610 A1 WO2023272610 A1 WO 2023272610A1 CN 2021103696 W CN2021103696 W CN 2021103696W WO 2023272610 A1 WO2023272610 A1 WO 2023272610A1
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WIPO (PCT)
Prior art keywords
alkyl
dye
composition
pyrazolidine
weight
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PCT/CN2021/103696
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English (en)
French (fr)
Inventor
Feiyu Zhang
Aziz Fadli
Zhibing Liu
Agathe LAHAYE
Jingmiao MA
Original Assignee
L'oreal
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Application filed by L'oreal filed Critical L'oreal
Priority to CN202180100134.9A priority Critical patent/CN117615746A/zh
Priority to PCT/CN2021/103696 priority patent/WO2023272610A1/en
Priority to CN202180100135.3A priority patent/CN117597104A/zh
Priority to PCT/CN2021/109548 priority patent/WO2023272863A1/en
Priority to FR2108681A priority patent/FR3124721A1/fr
Priority to FR2108977A priority patent/FR3124711A1/fr
Publication of WO2023272610A1 publication Critical patent/WO2023272610A1/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits

Definitions

  • the present invention relates to a dye kit for dyeing, especially for dyeing keratin fibers, in particular human keratin fibers, e.g., hair.
  • Dyes are widely used for various applications and fields, such as printing, paper, fabrics, cosmetics, medical science, paint, and others.
  • a rapid dyeing may be desirable.
  • a slow dyeing may be desirable.
  • a slow dyeing may result in a “revocable” effect of dyeing, allowing modifying or canceling certain undesired dyeing.
  • the dyeing product can comprise both at least one oxidative dye and at least one oxidant.
  • the oxidative dye and the oxidant may be placed respectively in a multi-compartment package, and are mixed together immediately before use.
  • the inventors have now discovered that the use of a specific retardant in a dye composition makes it possible to obtain a composition which can overcome the above drawbacks, especially reducing or even substantially avoiding of undesired stain by dye to a non-target position.
  • One subject of the present invention is thus a dye kit, comprising:
  • R 1 and R 2 are each independently H, hydroxyl, unsubstituted or substituted C1-C30 alkyl, unsubstituted or substituted C2-C30 alkenyl, cycloalkyl, unsaturated heterocyclic group, heterocyclic group or epoxylalkyl such as C1-C10 alkyl or halogen substituted C1-C10 alkyl, preferably C1-C6 alkyl or halogen substituted C1-C6 alkyl, C3-C10 alkenyl, C3-C10 cycloalkyl, C3-C10 unsaturated heterocyclic group, C3-C10 heterocyclic alkyl, or C3-C10 alkoxy; and R 3 is H, or unsubstituted or halogen substituted C1-C10 alkyl, C3-C10 cycloalkyl, C3-C10 heterocyclic alkyl, or C3-C10 alkoxy, such as C1-C6 alkyl
  • the pyrazolidine-3, 5-dione compound of formula (1) is placed together with the dyeing composition B) , or in a chamber separate from the dyeing composition B) .
  • the dyeing composition b) may be any conventional one useful for dyeing for various applications, such as printing, paper, fabrics, cosmetics, medical science, paint, and others.
  • the dyeing composition B may in turn comprise:
  • a colorant composition I) comprising:
  • a developer composition II) comprising:
  • the pyrazolidine-3, 5-dione compound of formula (1) is placed in the composition I) .
  • the present invention thus provides use of a pyrazolidine-3, 5-dione compound of formula (1) , used as a retardant, for slowing down reactions of dye or intermediates thereof.
  • the present invention also provides use of a pyrazolidine-3, 5-dione compound of formula (1) for reducing stain of a dye.
  • the present invention also provides use of a composition for reducing stain of a dye, wherein the composition comprises a pyrazolidine-3, 5-dione compound of formula (1) .
  • the present invention also relates to a process for dyeing, e.g., dyeing keratin fibers, in particular human keratin fibers such as the hair, using the dyeing composition B) according to the invention.
  • the present invention also relates to a process for reducing stain of dyeing, e.g., dyeing keratin fibers such as the hair, using the dyeing composition B) according to the invention.
  • the present invention also relates to a process of slowing down reactions of dye or intermediates thereof, characterized in mixing a pyrazolidine-3, 5-dione compound of formula (1) with the dye.
  • a pyrazolidine-3, 5-dione compound of formula (1) is mixed with the dye before application of the dye, or the pyrazolidine-3, 5-dione compound of formula (1) is applied to the position to which the dye has been applied for less than 10 minutes, less than 5 minutes, or less than 3 minutes.
  • Fig. 1 shows the stainless performances of the mixtures according to Example 3.
  • the “keratin fiber” according to the present invention is the hair, eyelashes, eyebrows, or body hair.
  • the keratin fiber according to the present invention is hair.
  • the term “retardant” means an agent capable of slowing down reactions of dye or intermediates thereof, such as the reactions with developer, e.g., an oxidation reaction therebetween.
  • reducing the stain refers to the reduction of stain occurring in undesired areas, such as hands, face, scalp, ears, rinsing water, towels, floor, and the like.
  • the effect lasts at least 5 minutes after the dyeing of the hair, more particularly 10 minutes, or preferably 15 minutes, or 20 minutes.
  • One subject of the present invention is to provide a dye kit, comprising the component of:
  • R 1 and R 2 are each independently H, hydroxyl, unsubstituted or substituted C1-C30 alkyl, unsubstituted or substituted C2-C30 alkenyl, cycloalkyl, unsaturated heterocyclic group, heterocyclic group or alkoxy, such as C1-C10 alkyl or halogen substituted C1-C10 alkyl, preferably C1-C6 alkyl or halogen substituted C1-C6 alky, C3-C10 alkenyl, C3-C10 cycloalkyl, C3-C10 heterocyclic alkyl, or C3-C10 epoxylalkyl; and R 3 is H, or unsubstituted or halogen substituted C1-C10 alkyl, C3-C10 cycloalkyl, C3-C10 unsaturated heterocyclic group, C3-C10 heterocyclic alkyl, or C3-C10 alkoxy, such as C1-C6 alkyl
  • the present invention provides a dye kit, comprising the components of:
  • the present invention provides a dye kit, comprising the components of:
  • a dyeing composition B) comprising:
  • a colorant composition I) comprising the components of:
  • a developer composition II) comprising the components of:
  • the dye kit of the invention is intended to be used in a process for dyeing keratin fibers.
  • a subject of the invention is thus a process of dyeing keratin fibers, which consists in mixing the colorant composition I) with the composition II) of the dyeing composition B) immediately before use to obtain a dye mixture, optionally adding a pyrazolidine-3, 5-dione compound of formula (1) into the dye mixture, and applying to the keratin fibers the dye kit of the invention.
  • a pyrazolidine-3, 5-dione compound of formula (1) can be added directly into the colorant composition I) .
  • the dye kit according to the present invention comprises a pyrazolidine-3, 5-dione compound of formula (1) :
  • R 1 and R 2 are each independently H, hydroxyl, unsubstituted or substituted C1-C30 alkyl, unsubstituted or substituted C2-C30 alkenyl, cycloalkyl, unsaturated heterocyclic group, heterocyclic group or alkoxy, such as C1-C10 alkyl or halogen substituted C1-C10 alkyl, preferably C1-C6 alkyl or halogen substituted C1-C6 alky, C3-C10 alkenyl, C3-C10 cycloalkyl, C3-C10 heterocyclic alkyl, or C3-C10 epoxylalkyl; and R 3 is H, or unsubstituted or halogen substituted C1-C10 alkyl, C3-C10 cycloalkyl, C3-C10 unsaturated heterocyclic group, C3-C10 heterocyclic alkyl, or C3-C10 alkoxy, such as C1-C6 alkyl
  • R 1 and R 2 are each lower alkyl, such as C1-C6 alkyl, or C1-C4 alkyl.
  • R 1 and R 2 can be same alkyl, such as being each methyl, ethyl, propyl or butyl.
  • R 3 may be H.
  • the examples of pyrazolidine-3, 5-dione compound of formula (1) may comprise 1, 2-dimethyl-pyrazolidine-3, 5-dione, 1, 2-diethyl-pyrazolidine-3, 5-dione, 1, 2-dipropyl-pyrazolidine-3, 5-dione and 1, 2-dibutyl-pyrazolidine-3, 5-dione.
  • the pyrazolidine-3, 5-dione compound of formula (1) in accordance with the invention are generally present in amounts ranging from 0.001%to 25%, by weight, or 0.0001%to 10%by weight, or preferably from 0.005%to 5%by weight, or particularly from 0.01%to 3%by weight, by weight relative to the total weight of the kit.
  • Dye kit comprising component A)
  • the dye kit comprising component A) according to the present invention may be useful for dyeing for various applications, such as printing, paper, fabrics, cosmetics, medical science, paint, and others.
  • the dye kit according to the present invention may be used to form an undyed area/pattern or lighter dyed area/pattern for an article, such as fabric or paper product, to be dyed.
  • component A) of the dye kit may be used to coat an area to be undyed or draw a pattern desired on the article. textile during which the colorant direct us to draw correctly. Then, the dye of the dye kit is applied to dye the article. By controlling the time period, a washing step is then applied to the article. Accordingly, the area coated by the component A) is not dyed or only slightly dyed.
  • the dye kit may comprise a washable colorant, especially for the case an artificial dyeing is to be carried out.
  • a washable colorant especially for the case an artificial dyeing is to be carried out.
  • those skilled can firstly mix the washable colorant with the component A) .
  • the mixture obtained is used to draw a pattern of bird on the textile during which the colorant direct the user to draw correctly. Then, the washing step described above is carried.
  • the dye kit according to the present invention may contain the component A) at different concentrations in two or more chambers, wherein chamber 1 comprises a first concentration of component A) ; and chamber 2 comprising a second concentration of component A) .
  • the different concentrations of component A) will result in reaction/dyeing time of dyes. Then, when the dyed subject is rinsed, a gradient of color may be formed.
  • the dye kit according to the present invention may comprise:
  • the time window may be less than 10 minutes, less than 5 minutes, or less than 3 minutes.
  • the specification may be placed together with the component A) in a same package, or may be placed or provided separate from the component A) , as long as the combination of the component A) and the specification can provide the indication and guide to rinse the undesirably dyed area.
  • the inventor has surprisingly discovered that the pyrazolidine-3, 5-dione compound of formula (1) can be used as a retardant to slow down reactions of dye or intermediates thereof, e.g., the oxidative dye i) useful in the composition I) .
  • the pyrazolidine-3, 5-dione compound of formula (1) acts mainly on the reaction of the dye. Accordingly, for the dye kit, the pyrazolidine-3, 5-dione compound of formula (1) can be added directly into the dyeing composition B) , e.g., as a mixture with the colorant composition I) ; or can be added into an independent chamber, e.g., in the form of a pyrazolidine-3, 5-dione composition comprising the pyrazolidine-3, 5-dione compound of formula (1) , separate from the dyeing composition B) .
  • the pyrazolidine-3, 5-dione composition can comprise any component known in the field of cosmetics benefiting the stability of the pyrazolidine-3, 5-dione compound of formula (1) .
  • a dyeing composition B) may be comprised in the dye kit of the present invention.
  • the dyeing composition B) placed in the kit according to the present invention may comprise a colorant composition I) and a developer composition II) .
  • the colorant composition I) and the developer composition II) can be used at a ratio by weight of 1: 3 to 3: 1, preferably 1: 2 to 2: 1, or preferably 2: 3 to 1: 1.
  • the dyeing composition B) placed in the kit according to the present invention comprises a colorant composition I) .
  • the colorant composition I) of the composition B) according to the present invention can comprise at least one oxidative dye (s) .
  • the colorant composition I) according to the invention comprises one or more oxidative dyes for use as component i) .
  • oxidative dyes that may be used in the present invention are generally chosen from oxidation bases, preferably combined with one or more couplers.
  • the oxidative dye (s) comprise one or more oxidation bases.
  • the oxidation bases may be chosen especially from para-phenylenediamines, bis (phenyl) alkylenediamines, para-aminophenols, ortho-aminophenols, heterocyclic bases, and the addition salts thereof, and mixtures thereof.
  • para-phenylenediamines an unsubstituted para-phenylenediamine or a para-phenylenediamine substituted with 1 or 2 C1-C4 alkyl is preferred.
  • examples that may be mentioned include para-phenylenediamine, 2-chloro-para-phenylenediamine, 2-methyl-para-phenylenediamine, 2, 3-dimethyl-para-phenylenediamine, 2, 6-dimethyl-para-phenylenediamine, 2, 6-diethyl-para-phenylenediamine, 2, 5-dimethyl-para-phenylenediamine.
  • para-phenylenediamines may also be used, for example, N, N-dimethyl-para-phenylenediamine, N, N-diethyl-para-phenylenediamine, N, N-dipropyl-para-phenylenediamine, 4-amino-N, N-diethyl-3-methylaniline, N, N-bis ( ⁇ -hydroxyethyl) -para-phenylenediamine, 4-N, N-bis ( ⁇ -hydroxyethyl) amino-2-methylaniline, 4-N, N–bis ( ⁇ -hydroxyethyl) amino-2-chloroaniline, 2- ⁇ -hydroxyethyl-para-phenylenediamine, 2-fluoro-para-phenylenediamine, 2-isopropyl-para-phenylenediamine, N- ( ⁇ -hydroxypropyl) -para-phenylenediamine, 2-hydroxymethyl-para-phenylenediamine, N, N-dimethyl-3-methyl-
  • the bis (phenyl) alkylenediamines examples include N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4'-aminophenyl) -1, 3-diaminopropanol, N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4'-aminophenyl) ethylenediamine, N, N'-bis (4-aminophenyl) tetramethylenediamine, N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4-aminophenyl) tetramethylenediamine, N, N'-bis (4-methylaminophenyl) tetramethylenediamine, N, N'-bis (ethyl) -N, N'-bis (4'-amino-3'-methylphenyl) ethylenediamine, 1, 8-bis (2, 5-diaminophenoxy)
  • para-aminophenols an unsubstituted para-aminophenol or a para-aminophenol substituted with 1 or 2 C1-C4 alkyl is preferred.
  • examples that may be mentioned include para-aminophenol, 4-amino-3-methylphenol, and 4-amino-2-methylphenol.
  • para-phenylenediamines may also be used, for example, 4-amino-3-fluorophenol, 4-amino-3-chlorophenol, 4-amino-3-hydroxymethylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2- ( ⁇ -hydroxyethyl-aminomethyl) phenol and 4-amino-2-fluorophenol, and the addition salts thereof with an acid.
  • 4-amino-3-fluorophenol 4-amino-3-chlorophenol, 4-amino-3-hydroxymethylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2- ( ⁇ -hydroxyethyl-aminomethyl) phenol and 4-amino-2-fluorophenol, and the addition salts thereof with an acid.
  • ortho-aminophenols examples that may be mentioned include 2-aminophenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol and 5-acetamido-2-aminophenol, and the addition salts thereof.
  • heterocyclic bases examples that may be mentioned include pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.
  • pyridine derivatives that may be mentioned are the compounds described, for example, in patents GB 1 026 978 and GB 1 153 196, for instance 2, 5-diaminopyridine, 2- (4-methoxyphenyl) amino-3-aminopyridine and 3, 4-diaminopyridine, and the addition salts thereof.
  • pyridine oxidation bases that are useful in the present invention are the 3-aminopyrazolo [1, 5-a] pyridine oxidation bases or the addition salts thereof described, for example, in patent application FR 2 801 308.
  • Examples that may be mentioned include pyrazolo [1, 5-a] pyrid-3-ylamine, 2- (acetylamino) pyrazolo [1, 5-a] pyrid-3-ylamine, 2- (morpholin-4-yl) pyrazolo [1, 5-a] pyrid-3-ylamine, 3-aminopyrazolo [1, 5-a] pyridine-2-carboxylic acid, 2-methoxypyrazolo [1, 5-a] pyrid-3-ylamine, (3-aminopyrazolo [1, 5-a] pyrid-7-yl) methanol, 2- (3-aminopyrazolo [1, 5-a] pyrid-5-yl) ethanol, 2- (3-aminopyrazolo
  • pyrimidine derivatives that may be mentioned are the compounds described, for example, in the patents DE 2359399; JP 88-169571; JP 05-63124; EP 0770375 or patent application WO 96/15765, such as 2, 4, 5, 6-tetraaminopyrimidine, 4-hydroxy-2, 5, 6-triaminopyrimidine, 2-hydroxy-4, 5, 6-triaminopyrimidine, 2, 4-dihydroxy-5, 6-diaminopyrimidine, 2, 5, 6-triaminopyrimidine and the addition salts thereof and the tautomeric forms thereof, when a tautomeric equilibrium exists.
  • pyrazole derivatives that may be mentioned are the compounds described in patents DE 3843892 and DE 4133957 and patent applications WO 94/08969, WO 94/08970, FR-A-2 733 749 and DE 195 43 988, for instance 4, 5-diaminopyrazole, 4, 5-diamino-1-methylpyrazole, 4, 5-diamino-1- ( ⁇ -hydroxyethyl) pyrazole, 3, 4-diaminopyrazole, 4, 5-diamino-1- (4'-chlorobenzyl) pyrazole, 4, 5-diamino-1, 3-dimethylpyrazole, 4, 5-diamino-3-methyl-1-phenylpyrazole, 4, 5-diamino-1-methyl-3-phenylpyrazole, 4-amino-1, 3-dimethyl-5-hydrazinopyrazole, 1-benzyl-4, 5-diamino-3-methylpyrazole, 4, 5-diamino
  • 4,5-diaminopyrazoles will preferably be used, e.g., 4, 5-diamino-1-hydroxy C1-C4 alkylpyrazole, and even more preferentially 4, 5-diamino-1- ( ⁇ -hydroxyethyl) pyrazole and/or a salt thereof, especially a sulphate thereof.
  • the oxidative dye (s) may also comprise one or more couplers, which may be chosen from those conventionally used for the dyeing of keratin fibers.
  • meta-phenylenediamines meta-aminophenols, meta-diphenols, naphthalene-based couplers, heterocyclic couplers, and also the addition salts thereof, and mixtures thereof.
  • unsubstituted meta-aminophenol or a meta-aminophenol substituted with 1 or 2 C1-C4 alkyl unsubstituted meta-diphenol or a meta-diphenol substituted with 1 or 2 C1-C4 alkyl
  • diamino-phenols or unsubstituted hydroxyindoles
  • an amino substituted hydroxypyridine or hydroxybenzomorpholine
  • Examples that may be mentioned include 1-hydroxy-3-aminobenzene, 1-methyl-2-hydroxy-4-aminobenzene, 1, 3-dihydroxybenzene, 1, 3-dihydroxy-2-methylbenzene, 5-amino-6-chloro-o-methylphenol, 2-methyl-5-hydroxyethylaminophenol, 4-chloro-1, 3-dihydroxybenzene, 2, 4-diamino-1- ( ⁇ -hydroxyethyloxy) benzene, 2-amino-4- ( ⁇ -hydroxyethylamino) -1-methoxybenzene, 1, 3-diaminobenzene, 1, 3-bis (2, 4-diaminophenoxy) propane, 3-ureidoaniline, 3-ureido-1-dimethylaminobenzene, sesamol, 1- ⁇ -hydroxyethylamino-3, 4-methylenedioxybenzene, ⁇ -naphthol, 2-methyl-1-naphthol, 6-hydroxyindole, 4-hydroxyind
  • addition salts of the oxidation bases and couplers that may be used within the context of the invention are especially chosen from the addition salts with an acid such as the hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates.
  • an acid such as the hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates.
  • examples comprise unsubstituted para-phenylenediamine or a para-phenylenediamine substituted with 1 or 2 C1-C4 alkyl.
  • examples comprise an unsubstituted para-aminophenol or a para-aminophenol substituted with 1 or 2 C1-C4 alkyl, in particular an unsubstituted para-aminophenol.
  • examples comprise 4, 5-diaminopyrazoles will preferably be used, e.g., 4, 5-diamino-1-hydroxy C1-C4 alkylpyrazole, or a salt thereof.
  • the unsubstituted para-aminophenol or a para-aminophenol substituted with 1 or 2 C1-C4 alkyl is particularly mentioned.
  • unsubstituted meta-aminophenol or a meta-aminophenol substituted with 1 or 2 C1-C4 alkyl unsubstituted meta-diphenol or a meta-diphenol substituted with 1 or 2 C1-C4 alkyl, diamino-phenols, or unsubstituted hydroxyindoles, an amino substituted hydroxypyridine, or hydroxybenzomorpholine can be preferably used.
  • an oxidation base according to the third exemplary embodiment for oxidation base is used, it is preferably used in combination with an amino substituted hydroxypyridine as a coupler.
  • the oxidation base (s) may advantageously represent from 0.0001%to 20%by weight, preferably from 0.01%to 10%by weight and better still from 0.1%to 5%by weight, relative to the total weight of the composition I) .
  • the coupler (s) may advantageously represent from 0.0001%to 20%by weight, and preferably from 0.001%to 10%by weight, or from 0.01%to 5%by weight, relative to the total weight of the composition I) .
  • the colorant composition I) can optionally comprise an antioxidant.
  • the antioxidants used may include natural exogenous phytochemical antioxidants such as phenols and carotenoids.
  • the antioxidant can include flavonoids.
  • Flavonoids constitute a large class of more than 5,000 polyphenolic phytochemicals with antioxidant properties that act by direct free radical scavenging. Flavonoids have anti-inflammatory, antibacterial, antiviral, anti-allergic, anti-mutagenic, anti-thrombotic, anti-tumor and vasodilating effects and these methods of action can also be used to prevent, alleviate or eliminate oxidative damage from dental instruments. Flavonoids also exhibit chelation properties with metal ions and can mitigate oxidative damage from metal ions by chelating ions. The formation and stability of flavonoid-metal chelate is dependent on the function of the structure. Flavonoids having a catechol moiety and having a hydrogen bond between the hydroxyl groups at the 5-position and the 3-position have chelation properties.
  • Vitamin C and derivatives can be used, including ascorbic acid, erythorbic acid, or derivatives thereof, e.g., sodium ascorbate/erythorbate and the fat-soluble ester tetrahexyl decyl ascorbate/erythorbate and ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl glucoside, glucosamine ascorbate, ascorbyl acetate, and the like.
  • ascorbic acid erythorbic acid, or derivatives thereof, e.g., sodium ascorbate/erythorbate and the fat-soluble ester tetrahexyl decyl ascorbate/erythorbate and ascorbyl palmitate
  • magnesium ascorbyl phosphate ascorbyl glucoside
  • glucosamine ascorbate ascorbyl acetate
  • Sesamum indicum or lignan may also be added. Sesame and its lignans (fibrous compounds associated with sesame) act as antioxidants. Sesame seed lignan significantly enhances vitamin E activity.
  • antioxidants which may be incorporated into the compositions of the present invention include tocopherols (e.g., d-alpha-tocopherol, d-beta-tocopherol, d-gamma-tocopherol, d-delta-tocopherol) , tocotrienol Phenol (eg d- ⁇ -tocotrienol, d- ⁇ -tocotrienol, d- ⁇ -tocotrienol, d- ⁇ -tocotrienol) and vitamin E ( ⁇ -tocopheryl acetate) ) .
  • tocopherols e.g., d-alpha-tocopherol, d-beta-tocopherol, d-gamma-tocopherol, d-delta-tocopherol
  • tocotrienol Phenol eg d- ⁇ -tocotrienol, d- ⁇ -tocotrienol, d- ⁇ -tocotrienol,
  • the tocotrienol-rich vitamin E preparation can be obtained by fractionating the vitamin E preparation to remove a portion of the biophenol and recovering the higher concentrated tocotrienol product.
  • Useful tocotrienols are natural products isolated, for example, from wheat germ oil, grain or palm oil using high performance liquid chromatography or from barley, distiller's grains or oats by alcohol extraction and/or molecular distillation.
  • the term "tocotrienol" as used herein includes a tocotrienol-rich fraction obtained from these natural products as well as a pure compound. Increased glutathione peroxidase activity protects the skin from oxidative damage.
  • carotenoids especially lutein types
  • lutein-type carotenoids include molecules such as lutein, canthaxantin, cryptoxanthin, zeaxanthin and astaxanthin.
  • Lutein compounds protect compounds such as vitamin A, vitamin E and other carotenoids.
  • the flavonoid may be a flavanone (a derivative of 2, 3-dihydro-2-phenylbenzopyran-4-one) .
  • Flavanones include: scutellarin, eriodictin, hesperetin, hesperidin, sylvestre, isosakuranetin, naringenin, naringin, pinocin, tangrin (poncirin) ) , sakuranetin, sakura glycosides and 7-O-methyl ergophenol (Sterubin) .
  • the flavonoid may be a dihydroflavonol (a derivative of 3-hydroxy-2, 3-dihydro-2-phenylbenzopyran-4-one) .
  • Flavanols include: taxifolin, Aromadedrin, Chrysandroside A, Chrysandroside B, Xeractinol, astilbin, and flavonol.
  • the flavonoid may be a flavonoid (a derivative of 2-phenylbenzopyran-4-one) .
  • Flavonoids include: Apigenin, luteolin, tangeritin, Chrysin, baicalein, wild baicalein, wogonin, synthetic flavonoids: Diosmin and flavonoids ester.
  • the flavonoid may be a flavonol (a derivative of 3-hydroxy-2-phenylbenzopyran-4-one) .
  • Flavonols include: 3-hydroxyflavone, rhodoxanthin, quercetin, galangin, cotton dermatan, kaempferol, kaempferol, isorhamnetin, mulberry pigment, myricetin, naringin (Natsudaidain) , Muskyl flavonol (Pachypodol) , quercetin, methyl rhamnosin, rhamnetin, azalein, hyperoside, isoquercetin, kaempferol, myricetin, suede Glycosides, Robinin, Rutin, Spiraea, Xanthorhamnin, Amurensin, Icariin and Tracuridine.
  • the flavonoid may be a flavan-3-ol (a derivative of 2-phenyl-3, 4-dihydro-2H-benzopyran-3-ol) .
  • Flavan-3-ol includes: catechin, epicatechin, epigallocatechin, epicatechin gallate, epigallocatechin gallate, epiafzelechin, Fisetinidol, Guibourtinidol, Mesquitol and Robinetinidol.
  • the flavonoid may be a flavan-4-ol (a derivative of 2-phenylchroman-4-ol) .
  • Flavan-4-ols include: Apiforol and Luteoforol.
  • the flavonoid may be an isoflavone (a derivative of 3-phenylbenzopyran-4-one) .
  • Isoflavones include: genistein, daidzein, garbanin A, formononetin, and equol metabolites from daidzein.
  • the antioxidant may be anthocyanin (a derivative of 2-phenylbenzopyranoside cation) .
  • Anthocyanins include: Aurantinidin, cyanidin, delphinidin, Europinidin, Luteolinidin, Pelargonidin, Malvidin, Peonyidin (Peonidin) ) , morning glory pigment (Petunidin) , rose pigment (Rosinidin) and xanthone.
  • the antioxidant may be dihydrochalcone (a derivative of 1, 3-diphenyl-1-propanone) .
  • Dihydrochalcone includes: phloretin, dihydrochalcone phloridin cisplatin, Aspalathin, naringin dihydrochalcone, neohesperidin dihydrochalcone and Nothofagin.
  • the mode of action of the present invention is not limited, but dihydrochalcone can exert an antioxidant effect by reducing active radicals such as active oxygen and reactive nitrogen species.
  • the antioxidant can be anthocyanin.
  • Anthocyanins and their derivatives are antioxidants.
  • Anthocyanins comprise a class of flavonoid compounds responsible for the red, purple and blue colors of many fruits, vegetables, grains and flowers, which are naturally occurring water-soluble compounds.
  • anthocyanins are collagenase inhibitors. Inhibition of collagenase helps prevent and reduce wrinkles caused by skin collagen reduction, increase skin elasticity, and the like.
  • Anthocyanins can be obtained from any part of a variety of plant sources, such as solids, flowers, stems, leaves, roots, bark or seeds.
  • the antioxidant can include one or more betaine. Betatin, similar to anthocyanins, is available from natural sources and is an antioxidant.
  • the antioxidant may be a phenylpropanoid (a derivative of cinnamic acid) .
  • Phenylpropanoids include: cinnamic acid, caffeic acid, ferulic acid, trans-ferulic acid (including its antioxidant pharmacore 2, 6-dihydroxy acetophenome) , 5-hydroxyferic acid, sinapic acid, Coumarin, coniferyl alcohol, sinapyl alcohol, eugenol, Chavicol, baicalein, P-coumaric acid and sinapinic acid.
  • phenylpropanoids can neutralize free radicals.
  • the antioxidant may be chalcone (a derivative of 1, 3-diphenyl-2-propen-1-one) .
  • Chalcone includes: zirconia, Okanin, safflower, Marein, Sophoradin, Xanthohumol, Flavokvain A, Flavokavain B, Flavokavin C and Synthetic Safalcone.
  • the antioxidant may be curcuminoid.
  • Curcuminoids include: curcumin, demethoxycurcumin, bis-demethoxycurcumin, tetrahydrocurcumin, and tetrahydrocurcumin.
  • Curcumin and tetrahydrocurcumin can be derived from the rhizome of turmeric. Tetrahydrocurcumin, a metabolite of curcumin, has been found to be a more potent antioxidant and more stable than curcumin.
  • the antioxidant can be tannin. Tannins include: tannins, Terflavin B, Glucogallin, Dgallic acid, and Quercitannic acid.
  • the antioxidant can be a stilbenoid.
  • the mites include: resveratrol, red sandalwood and paclitaxel.
  • Resveratrol can include, but is not limited to, 3, 5, 4'-trihydroxyindole, 3, 4, 3', 5'-tetrahydroxyindole (cetotriol) , 2, 3', 4, 5'-Tetrahydroxyindole (oxidized resveratrol) , 4, 4'-dihydroxyindole and its alpha and beta glucoside, galactoside and mannoside derivatives.
  • the antioxidant may be coumarin (a derivative of 2H-benzopyran-2-one) .
  • Coumarins include: 4-hydroxycoumarin, umbelliferone, Aesculetin, Herniarin, Auraptene, and dicoumarin.
  • the antioxidant can be a carotenoid.
  • Carotenoids include: beta-carotene, alpha-carotene, gamma-carotene, beta-cryptoxanthin, lycopene, lutein and idebenone.
  • the antioxidant can be a vitamin of a derivative thereof.
  • Vitamins include: retinol, ascorbic acid or erythorbic acid, L-ascorbic acid, tocopherol, tocotrienol and vitamin cofactor: coenzyme Q10.
  • the antioxidant may be: xanthone, butylated hydroxytoluene, 2, 6-di-tert-butylphenol, 2, 4-dimethyl-6-tert-butylphenol, gallic acid, eugenol, uric acid, ⁇ -lipoic acid, ellagic acid, cichoric acid, chlorogenic acid, rosmarinic acid, salicylic acid, acetylcysteine, S-allylcysteine, pyridone (Barbigerone) , Chebulagic acid, edaravone, ethoxyquin, glutathione, hydroxytyrosol, idebenone, melatonin, N-acetyl serotonin, nordihydroguaiac Acid, Oleotanthal, oleuropein, Paradol, paclitaxel, probucol, propyl gallate, protocatechuic acid, pyrithione, rutin, flax
  • the colorant composition I) can comprise a reducer for use as an antioxidant.
  • useful reducers can comprise, sodium thiosulfate, sodium metabisulfite, thiourea sulfite ammonium, thioglycolic acid (TGA) , thiolactic acid, ammonium thiolactate, mono-carbothioic acid diglycidyl ester, carbothioic ammonium acetate, thioglycerol, dithio glycolic acid, diammonium carbothioic strontium acetate, thio glycolate, carbothioic isooctyl, cysteine, cysteamine, homocysteine, glutathione peptide, thiomalic acid, 2-mercaptopropionic acid, 3-mercaptopropionic acid, thiodiglycol, 2-mercaptoethanol, dithiothreitol, thioxanthine, thiosalicylic acid thiopropionic acid, lipoic acid, N-acetylc
  • Examples of preferred reducers include thioglycolic acid, dithio glycolic acid, thiolactic acid, thiomalic acid, the salts thereof, or a mixture thereof.
  • the antioxidant including the reducer, described above is preferably used according to the invention in an amount which may range from 0.001 to 10%by weight, preferably from 0.1 to 7%by weight, or preferably from 0.5 to 5%by weight, relative to the total weight of the colorant composition I) .
  • the colorant composition I) according to the invention may comprise one or more surfactant (s) , e.g., in particular anionic surfactant and/or non-ionic surfactant.
  • surfactant e.g., in particular anionic surfactant and/or non-ionic surfactant.
  • the colorant composition I) according to the invention may further comprise one or more anionic surfactant (s) .
  • anionic surfactant means a surfactant comprising, as ionic or ionizable groups, only anionic groups. These anionic groups are preferably chosen from the following groups:
  • anionic surfactants that may be used in the colorant composition I) according to the invention, mention may be made of alkyl sulfates, alkyl ether sulfates, alkylamido ether sulfates, alkylaryl polyether sulfates, monoglyceride sulfates, alkylsulfonates, alkylamidesulfonates, alkylarylsulfonates, ⁇ -olefin sulfonates, paraffin sulfonates, alkyl sulfosuccinates, alkyl ether sulfosuccinates, alkylamide sulfosuccinates, alkyl sulfoacetates, acylsarcosinates, acylglutamates, alkyl sulfosuccinamates, acylisethionates and N-acyltaurates, polyglycoside polycarboxylic acid and alkyls
  • These compounds can be oxyethylenated and then preferably comprise from 1 to 50 ethylene oxide units.
  • the salts of C 6 -C 24 alkyl monoesters of polyglycoside-polycarboxylic acids may be chosen from C 6 -C 24 alkyl polyglycoside-citrates, C 6 -C 24 alkyl polyglycoside-tartrates and C 6 -C 24 alkyl polyglycoside-sulfosuccinates.
  • anionic surfactant (s) When the anionic surfactant (s) are in salt form, they may be chosen from alkali metal salts such as the sodium or potassium salt and preferably the sodium salt, ammonium salts, amine salts and in particular amino alcohol salts, or alkaline-earth metal salts such as the magnesium salts.
  • alkali metal salts such as the sodium or potassium salt and preferably the sodium salt, ammonium salts, amine salts and in particular amino alcohol salts, or alkaline-earth metal salts such as the magnesium salts.
  • amino alcohol salts examples include monoethanolamine, diethanolamine and triethanolamine salts, monoisopropanolamine, diisopropanolamine or triisopropanolamine salts, 2-amino-2-methyl-1-propanol salts, 2-amino-2-methyl-1, 3-propanediol salts and tris (hydroxymethyl) aminomethane salts.
  • Alkali metal or alkaline-earth metal salts and in particular sodium or magnesium salts, are preferably used.
  • Preferred anionic surfactants are chosen from (C 6 -C 30 ) alkyl sulfates, (C 6 -C 30 ) alkyl ether sulfates, (C 6 -C 30 ) alkylamido ether sulfates, alkylaryl polyether sulfates and monoglyceride sulphates, all these compounds optionally comprising from 1 to 20 ethylene oxide units; or preferably from (C 12 -C 20 ) alkyl sulphates and (C 12 -C 20 ) alkyl ether sulfates comprising from 2 to 20 ethylene oxide units, e.g., from 1 to 4 ethylene oxide units, especially in the form of alkali metal, ammonium, amino alcohol and alkaline-earth metal salts, or a mixture of these compounds.
  • a polyoxyethylenated sodium lauryl ether sulphate such as sodium lauryl ether sulphate containing 2 or
  • the anionic surfactants of the invention are sulfates, more specifically is chosen from (C 6 -C 30 ) alkyl sulfates, (C 6 -C 30 ) alkyl ether sulfates, (C 6 -C 30 ) alkylamido ether sulfates, alkylaryl polyether sulfates and monoglyceride sulfates, their salts such as alkali salts, such as sodium, and their mixtures.
  • the anionic surfactants of the invention are chosen from (C 6 -C 30 ) alkyl sulfates, (C 6 -C 30 ) alkyl ether sulfates, particularly (C 6 -C 30 ) alkyl ether sulfates such as lauryl ether sulfate, their salts, such as sodium laureth sulfate.
  • the amount of said anionic surfactant (s) in the colorant composition I) according to the invention is 0.01 to 20%by weight, preferably 0.1 to 10%by weight, or preferably 0.1 to 8%by weight, with regard to the total weight of the composition I) .
  • the colorant composition I) according to the invention may further contain one or more non-ionic surfactant (s) .
  • nonionic surfactant (s) that may be used in the compositions are described, for example, in the Handbook of Surfactants by M.R. Porter, published by Blackie&Son (Glasgow and London) , 1991, pp. 116-178.
  • nonionic surfactants examples include the following nonionic surfactants:
  • C 8 -C 20 and better still C 10 -C 18 fatty alcohols comprising from 1 to 100 mol of ethylene oxide, preferably from 2 to 50, more particularly from 2 to 40 mol, or even from 3 to 20 mol of ethylene oxide;
  • C 8 -C 30 alkyl (poly) glucosides
  • C 8 -C 30 alkenyl (poly) glucosides, which are optionally oxyalkylenated (0 to 10 oxyalkylene units) and comprising from 1 to 15 glucose units, (C 8 -C 30 ) alkyl (poly) glucoside esters;
  • oxyalkylenated covers, respectively, mono-or poly-oxyalkylenated, oxyethylenated, oxypropylenated and glycerolated compounds, unless specifically mentioned.
  • the oxyalkylene units are more particularly oxyethylene or oxypropylene units, or a combination thereof, preferably oxyethylene units.
  • the number of moles of ethylene oxide and/or propylene oxide preferably ranges from 1 to 250, more particularly from 2 to 100 and better still from 2 to 50; the number of moles of glycerol ranges especially from 1 to 50 and better still from 1 to 10.
  • nonionic surfactants according to the invention do not comprise any oxypropylene units.
  • Examples may comprise especially lauryl alcohol containing 4 mol of ethylene oxide (INCI name: Laureth-4) and lauryl alcohol containing 12 mol of ethylene oxide (INCI name: Laureth-12) .
  • Other examples may comprise OLETH-10, OLETH-30, DECETH-3, DECETH-5 and the like.
  • glycerolated nonionic surfactants use is preferably made of monoglycerolated or polyglycerolated C 8 -C 40 alcohols, comprising from 1 to 50 mol of glycerol and preferably from 1 to 10 mol of glycerol.
  • lauryl alcohol containing 4 mol of glycerol (INCI name: Polyglyceryl-4 Lauryl Ether) , lauryl alcohol containing 1.5 mol of glycerol, oleyl alcohol containing 4 mol of glycerol (INCI name: Polyglyceryl-4 Oleyl Ether) , oleyl alcohol containing 2 mol of glycerol (INCI name: Polyglyceryl-2 Oleyl Ether) , cetearyl alcohol containing 2 mol of glycerol, cetearyl alcohol containing 6 mol of glycerol, oleyl/cetyl alcohol containing 6 mol of glycerol, and octadecanol containing 6 mol of glycerol.
  • glycerolated alcohols it is more particularly preferred to use the C 8 /C 10 alcohol containing 1 mol of glycerol, the C 10 /C 12 alcohol containing 1 mol of glycerol and the C 12 alcohol containing 1.5 mol of glycerol.
  • the nonionic surfactant (s) when they are present in the colorant composition I) according to the invention, are preferably present in a total amount ranging from 0.01 to 1%by weight, with regard to the total weight of the composition.
  • the colorant composition I) according to the invention can advantageously comprise one or more solvent (s) , e.g., water and/or organic solvent.
  • solvent e.g., water and/or organic solvent.
  • the colorant composition I) according to the invention advantageously comprises water, in a content of less than or equal to 40%by weight relative to the total weight of composition I) .
  • the water content in the colorant composition I) according to the invention preferably ranges from 10%to 40%by weight, more preferentially from 15%to 35%by weight, or from 20%to 30%by weight, relative to the total weight of the composition I) .
  • the colorant composition I) according to the invention may also comprise one or more water-soluble organic solvents (solubility of greater than or equal to 5%in water at 25°C and at atmospheric pressure) .
  • water-soluble organic solvents examples include linear or branched and preferably saturated monoalcohols or diols, comprising 2 to 10 carbon atoms, such as ethyl alcohol, isopropyl alcohol, hexylene glycol (2-methyl-2, 4-pentanediol) , neopentyl glycol and 3-methyl-1, 5-pentanediol, butylene glycol, dipropylene glycol and propylene glycol; aromatic alcohols such as phenylethyl alcohol; polyols containing more than two hydroxyl functions, such as glycerol; polyol ethers, for instance ethylene glycol monomethyl, monoethyl and monobutyl ether, propylene glycol or ethers thereof, for instance propylene glycol monomethyl ether; and also diethylene glycol alkyl ethers, especially C 1 -C 4 alkyl ethers, for instance diethylene glycol monoethyl ether or
  • the water-soluble organic solvents when they are present, generally represent between 1%and 20%by weight relative to the total weight of the colorant composition I) according to the invention, and preferably between 3%and 15%by weight, or between 4%and 10%by weight.
  • the colorant composition I) according to the invention may further comprise one or more alkaline agents.
  • the alkaline agent (s) can especially be chosen from aqueous ammonia, alkali metal carbonates or bicarbonates, organic amines with a pKb at 25°C of less than 12, in particular less than 10 and even more advantageously less than 6; from the salts of the amines mentioned previously with acids such as carbonic acid or hydrochloric acid: it should be noted that it is the pKb corresponding to the function of highest basicity.
  • composition I) according to the present invention can be free of or substantially free of aqueous ammonia.
  • the amines are chosen from alkanolamines, in particular comprising a primary, secondary or tertiary amine function, and one or more linear or branched C 1 -C 8 alkyl groups bearing one or more hydroxyl radicals; from oxyethylenated and/or oxypropylenated ethylenediamines, and from amino acids and compounds having the following formula:
  • W is a C 1 -C 6 alkylene residue optionally substituted with a hydroxyl group or a C 1 -C 6 alkyl radical
  • Rx, Ry, Rz and Rt which may be identical or different, represent a hydrogen atom or a C 1 -C 6 alkyl, C 1 -C 6 hydroxyalkyl or C 1 -C 6 aminoalkyl radical.
  • the colorant composition I) according to the invention comprises at least one alkanolamine and/or at least one basic amino acid, more advantageously at least one alkanolamine, such as ethanolamine, or mixtures thereof.
  • the content of alkaline agent (s) ranges from 0.01%to 30%by weight, preferably from 0.1%to 20%by weight, or from 1%to 10%or 5%by weight relative to the total weight of the composition I) . It should be noted that this content is expressed as NH 3 when the alkaline agent is aqueous ammonia.
  • composition I) of the invention is preferably 6-11.
  • the pH can be adjusted by adding acidifying agents, such as hydrochloric acid, (ortho) phosphoric acid, sulfuric acid, boric acid, and also carboxylic acids, for instance acetic acid, lactic acid or citric acid, or sulfonic acids.
  • acidifying agents such as hydrochloric acid, (ortho) phosphoric acid, sulfuric acid, boric acid, and also carboxylic acids, for instance acetic acid, lactic acid or citric acid, or sulfonic acids.
  • Alkaline agents such as those previously mentioned may also be used.
  • the colorant composition I) according to the invention can comprise, moreover, a cosmetically acceptable fatty substance.
  • the fatty substance is free of carboxylic acid groups.
  • fatty substance means organic compounds that are insoluble in water at ordinary temperature (25°C) and at atmospheric pressure (760 mmHg) (solubility of less than 5%, preferably 1%and even more preferentially 0.1%) . They may preferably have in their structure a sequence of at least two siloxane groups or at least one hydrocarbon-based chain comprising at least 6 carbon atoms. In addition, the fatty substances are generally soluble in organic solvents under the same temperature and pressure conditions, for instance chloroform, ethanol, benzene or decamethylcyclo-pentasiloxane.
  • the fatty substances are especially chosen from lower alkanes, fatty alcohols, fatty acid esters, fatty alcohol esters, oils, in particular mineral, plant, animal or synthetic non-silicone oils, non-silicone waxes, and silicones.
  • the fatty alcohols, fatty esters and fatty acids more particularly contain one or more linear or branched, saturated or unsaturated hydrocarbon-based groups comprising 6 to 30 carbon atoms, which is (are) optionally substituted, in particular with one or more hydroxyl groups (in particular 1 to 4) . If they are unsaturated, these compounds may comprise one to three conjugated or unconjugated carbon-carbon double bonds.
  • these alkanes comprise from 6 to 16 carbon atoms and are linear or branched, optionally cyclic.
  • the alkanes may be chosen from hexane and dodecane, isoparaffins such as isohexadecane and isodecane.
  • non-silicone oils that may be used in the composition of the invention, examples that may be mentioned include:
  • oils of plant origin such as liquid fatty acid triglycerides containing from 6 to 30 carbon atoms, for instance heptanoic or octanoic acid triglycerides, or alternatively, for example, sunflower oil, corn oil, soybean oil, marrow oil, grapeseed oil, sesameseed oil, hazelnut oil, apricot oil, macadamia oil, arara oil, castor oil, avocado oil, caprylic/capric acid triglycerides, for instance those sold by the company Stéarineries Dubois or those sold under the names 810, 812 and 818 by the company Dynamit Nobel, jojoba oil and shea butter oil;
  • fluoro oils for instance perfluoromethylcyclopentane and perfluoro-1, 3-dimethylcyclohexane, sold under the names PC1 and PC3 by the company BNFL Fluorochemicals; perfluoro-1, 2-dimethylcyclobutane; perfluoroalkanes such as dodecafluoropentane and tetradecafluorohexane, sold under the names PF and PF by the company 3M, or bromoperfluorooctyl sold under the name by the company Atochem; nonafluoromethoxybutane and nonafluoroethoxyisobutane; perfluoromorpholine derivatives such as 4-trifluoromethyl perfluoromorpholine sold under the name PF by the company 3M.
  • the fatty alcohols that may be used in the composition of the invention are not oxyalkylenated. They are saturated or unsaturated, linear or branched and comprise from 6 to 30 carbon atoms and more particularly from 8 to 30 carbon atoms. Mention may be made of cetyl alcohol, stearyl alcohol and the mixture thereof (cetylstearyl alcohol) , octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, oleyl alcohol or linoleyl alcohol.
  • esters useful are esters of saturated or unsaturated, linear or branched C 1 -C 26 aliphatic mono-or polyacids and of saturated or unsaturated, linear or branched C 1 -C 26 aliphatic mono-or polyalcohols, the total carbon number of the esters being more particularly greater than or equal to 10.
  • dihydroabietyl behenate octyldodecyl behenate; isocetyl behenate; cetyl lactate; C 12 -C 15 alkyl lactate; isostearyl lactate; lauryl lactate; linoleyl lactate; oleyl lactate; (iso) stearyl octanoate; isocetyl octanoate; octyl octanoate; cetyl octanoate; decyl oleate; isocetyl isostearate; isocetyl laurate; isocetyl stearate; isodecyl octanoate; isodecyl oleate; isononyl isononanoate; isostearyl palmitate; methylacetyl ricinoleate; myristyl stearate
  • esters of C 4 -C 22 dicarboxylic or tricarboxylic acids and of C 1 -C 22 alcohols and esters of mono-, di-or tricarboxylic acids and of C 2 -C 26 di-, tri-, tetra-or pentahydroxy alcohols may also be used.
  • diethyl sebacate diisopropyl sebacate; diisopropyl adipate; di-n-propyl adipate; dioctyl adipate; diisostearyl adipate; dioctyl maleate; glyceryl undecylenate; octyldodecyl stearoyl stearate; pentaerythrityl monoricinoleate; pentaerythrityl tetraisononanoate; pentaerythrityl tetrapelargonate; pentaerythrityl tetraisostearate; pentaerythrityl tetraoctanoate; propylene glycol dicaprylate; propylene glycol dicaprate; tridecyl erucate; triisopropyl citrate; triisostearyl citrate; glyceryl trilactate;
  • composition may also comprise, as fatty ester, sugar esters and diesters of C 6 -C 30 and preferably C 12 -C 22 fatty acids.
  • sugar esters and diesters of C 6 -C 30 and preferably C 12 -C 22 fatty acids.
  • sugar esters and diesters of C 6 -C 30 and preferably C 12 -C 22 fatty acids.
  • sugar esters oxygenous hydrocarbon-based compounds containing several alcohol functions, with or without aldehyde or ketone functions, and which comprise at least 4 carbon atoms.
  • sugars may be monosaccharides, oligosaccharides or polysaccharides.
  • suitable sugars include sucrose (or saccharose) , glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose and lactose, and derivatives thereof, especially alkyl derivatives, such as methyl derivatives, for instance methylglucose.
  • the sugar esters of fatty acids may be chosen especially from the group comprising the esters or mixtures of esters of sugars described previously and of linear or branched, saturated or unsaturated C 6 -C 30 and preferably C 12 -C 22 fatty acids. If they are unsaturated, these compounds may comprise one to three conjugated or unconjugated carbon-carbon double bonds.
  • esters according to this variant may also be chosen from mono-, di-, tri-, tetraesters and polyesters, and mixtures thereof.
  • esters may be chosen, for example, from oleates, laurates, palmitates, myristates, behenates, cocoates, stearates, linoleates, linolenates, caprates and arachidonates, or mixtures thereof such as, especially, oleo-palmitate, oleo-stearate and palmito-stearate mixed esters.
  • monoesters and diesters and especially sucrose, glucose or methylglucose mono-or dioleates, stearates, behenates, oleopalmitates, linoleates, linolenates and oleostearates.
  • the content of fatty substance (s) ranges from 0.01%to 45%by weight, preferably from 0.1%to 30%by weight, or from 1%to 15%by weight relative to the total weight of the composition I) .
  • the colorant composition I) according to the invention may also comprise one or more cosmetic adjuvants.
  • composition I) may comprise one or more additives that are well known in the art, such as anionic, nonionic or amphoteric polymers or mixtures thereof, agents for preventing hair loss, vitamins and provitamins including panthenol, the derivatives of these vitamins (in particular esters) and their mixtures; sunscreens, mineral or organic pigments, sequestrants, plasticizers, solubilizers, acidifying agents, opacifiers, hydroxy acids, nacreous agents, fragrances and preserving agents.
  • additives that are well known in the art, such as anionic, nonionic or amphoteric polymers or mixtures thereof, agents for preventing hair loss, vitamins and provitamins including panthenol, the derivatives of these vitamins (in particular esters) and their mixtures; sunscreens, mineral or organic pigments, sequestrants, plasticizers, solubilizers, acidifying agents, opacifiers, hydroxy acids, nacreous agents, fragrances and preserving agents.
  • the above adjuvants may generally be present in an amount, for each of them, of between 0 and 20%by weight, or between 0 and 10%by weight, relative to the total weight of the composition I) .
  • composition I) according to the invention may be in the form of fluid or thickened liquids, gels or creams, preferably cream.
  • the dyeing composition B) placed in the kit according to the present invention may comprise a developer composition II) .
  • the developer composition II) is placed separate from the colorant composition I) .
  • composition II) of the composition B) according to the present invention comprises at least one oxidant.
  • the developer composition II) of the present invention may comprise one or more oxidant for generally use as one of the active components of the composition II) .
  • oxidant is intended to mean an oxidant other than atmospheric oxygen. More particularly, the oxidant is selected from the group consisting of hydrogen peroxide, urea peroxide, alkali metal bromates, peroxy salts, such as persulfates or perborates, peracids and their precursors, and alkali or alkaline earth metals; or a polymer type complex capable of releasing hydrogen peroxide.
  • the oxidant is hydrogen peroxide.
  • the concentration of the oxidant may be from 0.1%by weight to 50%by weight, or preferably from 0.5%by weight to 20%by weight, or from 1%by weight to 15%by weight, based on the weight of the composition II) .
  • the developer composition II) of the present invention may comprise one or more solvent (s) , e.g., water and/or organic solvent.
  • solvent e.g., water and/or organic solvent.
  • the useful solvent can be selected from those discussed for the “solvent” of the composition I) above.
  • composition I) and II) of the dyeing composition B) can independently use same or different solvents, respectively.
  • water When water is used as a solvent in the developer composition II) according to the invention, it is preferably used in a content of ranging from 40%to 95%by weight, more preferentially from 50%to 90%by weight, or from 60%to 85%by weight, relative to the total weight of the composition II) .
  • water-soluble organic solvents examples include polyols containing more than two hydroxyl functions, such as glycerol.
  • the water-soluble organic solvents when they are present, generally represent between 0.01%and 10%by weight relative to the total weight of the colorant composition I) according to the invention, and preferably between 0.1%and 5%by weight, or between 0.5%and 1%by weight.
  • the developer composition II) according to the invention may comprise one or more surfactant (s) , e.g., in particular anionic surfactant and/or non-ionic surfactant, preferably non-ionic surfactant.
  • surfactant e.g., in particular anionic surfactant and/or non-ionic surfactant, preferably non-ionic surfactant.
  • the useful surfactant can be selected from those discussed for the “surfactant” of the composition I) above.
  • the colorant composition I) and/or the developer composition II) of dyeing composition B) according to the present invention may comprise at least one chelating agent.
  • the useful chelating agent comprises aminocarboxylic acids, e.g., ethylenediamine tetraacetic acid (EDTA) , aminotriacetic acid, diethylene triaminepentaacetic acid, and in particular the alkali metal salt thereof, e.g., N, N-bis (carboxymethyl) glutamic acid, tetrasodium EDTA, tetrasodium salt of N, N-bis (carboxymethyl) glutamic acid (glutamic acid diacetic acid, GLDA) ; hydroxyl carboxylic acids, e.g., citric acid, tartaric acid, glucuronic acid, succinic acid, ethylenediamine disuccinic acid (EDDS) , and in particular the alkali metal salt thereof; hydroxyl aminocarboxylic acids, e.g., hydroxyethylethylenediamine triacetic acid (HEDTA) , dihydroxyethylglycine (DEG)
  • the at least one water soluble chelating agent is an alkali metal hydroxyl polycarboxylate represented by an alkane containing from 1 to 4 carbon atoms, preferably containing 2 or 3 carbon atoms, substituted by 1, 2, or 3 hydroxyl groups (-OH) , preferably by one (1) hydroxyl group, and further substituted by 2, 3, 4 or 5 carboxylate groups (-COOM) , preferably by 2 or 3 carboxylate groups (-COOM) , wherein the multiple groups M independently represent H or alkali metal, with the proviso that at least one of the groups M represents alkali metal, such as Na, K or Li, preferably all groups M represent alkali metal, such as Na, K or Li, preferably Na.
  • alkali metal hydroxyl polycarboxylate represented by an alkane containing from 1 to 4 carbon atoms, preferably containing 2 or 3 carbon atoms, substituted by 1, 2, or 3 hydroxyl groups (-OH) , preferably by one (1) hydroxyl group,
  • the at least one alkali metal hydroxyl polycarboxylate may be chosen from sodium tartrates, sodium citrates, potassium tartrates, potassium citrates, and hydrates thereof, preferably sodium citrates, in particularly trisodium citrate.
  • sodium citrates are used to indicate monosodium citrate, disodium citrate and trisodium citrate, and other alkali metal hydroxyl polycarboxylates may be understood in a similar way.
  • the alkali metal mentioned above is preferably sodium or potassium, in particular sodium.
  • preferable chelating agents can comprise sodium citrate, tetrasodium EDTA, tetrasodium GLDA, trisodium EDDS, sodium phytate, or a mixture thereof.
  • composition I) and/or composition II) of the present invention may comprise the at least one water soluble chelating agent in a content ranging from 0.01%to 1%by weight, especially from 0.1%to 0.4%by weight, relative to the total weight of the second composition.
  • One subject of the invention is a process for dyeing human keratin fibers, in particular the hair, using the dye kit as described above.
  • Another subject of the invention is a process for reducing the stain of a dye composition, using the dye kit as described above.
  • Another subject of the invention is a process for slowing down reactions of dye or intermediates, using the dye kit as described above.
  • the invention also relates to the use of the dye kit as described above for dyeing keratin fibers, in particular the hair.
  • the invention also relates to the use of the dye kit as described above for reducing the stain of the dye kit.
  • the invention also relates to the use of a dye kit as described above for slowing down reactions of dye or intermediates, using the dye kit as described above.
  • the invention relates to a process of slowing down reactions of dye or intermediates thereof, characterized in mixing a pyrazolidine-3, 5-dione compound of formula (1) comprising phenyl methyl pyrazolone with the dye.
  • the pyrazolidine-3, 5-dione compound of formula (1) is mixed with the dye before application of the dye, or the pyrazolidine-3, 5-dione compound of formula (1) is applied to the position to which the dye has been applied for less than 10 minutes, less than 5 minutes, or less than 3 minutes.
  • the present invention also relates to the use of a pyrazolidine-3, 5-dione compound of formula (1) comprising phenyl methyl pyrazolone for reducing stain of a dye.
  • the present invention relates to the use of a composition for dyeing keratin fibers, while reducing the stain in areas other than the keratin fibers, wherein the composition comprises a pyrazolidine-3, 5-dione compound of formula (1) comprising phenyl methyl pyrazolone.
  • the dyeing process of the invention comprises mixing the colorant composition I) and the composition II) immediately before use, and applying the mixture obtained as described above to the keratin fibers.
  • mixing or a variant thereof, it is intended to mean the action of putting the colorant composition I) of the present invention into a container or palm, together with the developer composition II) as described above, with or without stirring them.
  • the colorant composition I) of the present invention is put into a container or palm together with the developer composition II) as described above, without stirring them.
  • compositions described previously, optionally mixed beforehand, are applied to wet or dry keratin fibers.
  • the pyrazolidine-3, 5-dione compound of formula (1) can be provided in various forms to be used with the colorant composition I) and the developer composition II) , so as to slow down the reaction of the dye.
  • the pyrazolidine-3, 5-dione compound of formula (1) is placed in chamber 2 separate from chamber 1, for the dye kit described according to the present invention:
  • chamber 2 may not be used;
  • chamber 2 if the user wants to determine the use or not of chamber 2 depending on whether an actual stain occurs, he/she can firstly use only chamber 1, and when the dyeing composition is adhered to hand or anywhere else, chamber 2 may be immediately applied;
  • a pyrazolidine-3, 5-dione compound of formula (1) is provided together with the colorant composition I) , e.g., being added directly into the composition I) , the dyeing process is always slowed down, comparing with a same dyeing process except for the absence of any pyrazolidine-3, 5-dione compound of formula (1) .
  • the mixed compositions including the colorant composition I) and the developer composition II) , and optionally the pyrazolidine-3, 5-dione compound of formula (1) , are usually left in place on the fibers for a time generally ranging from 1 minute to 1 hour and preferably from 5 minutes to 30 minutes.
  • the temperature during the process is conventionally between 20 and 80°Cand preferably between 20 and 60°C.
  • the human keratin fibers are advantageously rinsed with water. They may optionally be further washed with a shampoo, followed by rinsing with water, before being dried or left to dry.
  • the process may be repeated several times in order to obtain the desired coloration.
  • the dye kit according to the present invention allows a method of generating gradient colors, comprising: providing a composition comprising the dye and component A) from the dye kit; applying a first part of the composition for dyeing, and with a time interval, applying a followed part of the composition, wherein the number of intervals depends on the number of colors to be obtained.
  • the abovementioned dye kit may also be equipped with means allowing the delivery to the hair of the desired mixture, such as, for example, the device described in patent FR 2 586 913.
  • compositions/formulas described below are expressed in %by weight, relative to the total weight of each composition/formula.
  • compositions I-A and I-B hereinafter were prepared, from the ingredients indicated in the table 1 below (in which the contents were indicated in wt%of materials with regard to the total weight of the composition) :
  • the developer composition II-A hereinafter was prepared, from the ingredients indicated in the table 2 below (in which the contents were indicated in wt%of materials with regard to the total weight of the composition) :
  • compositions I-A ⁇ B were mixed respectively with compositions II-A ⁇ B with a weight ratio of 1: 1.5, to provide mixtures A and B.
  • compositions I-A ⁇ B were mixed respectively with compositions II-A ⁇ B with a weight ratio of 1: 1.5, to provide mixtures A and B.
  • the mixtures were respectively applied on 1g of hair swatch on the hot plate of27°Cfor 30mins.
  • the hair was rinsed in a beaker containing 400 mL of water for 10s.
  • the transparency of the rising water was observed in the beaker. Photos were taken to record the experiment.
  • the stainless performances of the mixtures were scored by an internal expert panel from 0 to 10, where 10 represented completely clean, and 0 represented extremely dirty. The results were provided in Table 4 below and Fig. 1:

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PCT/CN2021/103696 2021-06-30 2021-06-30 Dye kit WO2023272610A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
CN202180100134.9A CN117615746A (zh) 2021-06-30 2021-06-30 染料套装
PCT/CN2021/103696 WO2023272610A1 (en) 2021-06-30 2021-06-30 Dye kit
CN202180100135.3A CN117597104A (zh) 2021-06-30 2021-07-30 用于染色角蛋白纤维的组合及其用途
PCT/CN2021/109548 WO2023272863A1 (en) 2021-06-30 2021-07-30 Combination for dyeing keratin fibers and use thereof
FR2108681A FR3124721A1 (fr) 2021-06-30 2021-08-13 Un kit de teinture
FR2108977A FR3124711A1 (fr) 2021-06-30 2021-08-27 Combinaison pour la teinture des fibres kératineuses et son utilisation

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PCT/CN2021/103696 WO2023272610A1 (en) 2021-06-30 2021-06-30 Dye kit

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US20010054205A1 (en) * 1996-03-22 2001-12-27 L'oreal Pyrazoline-3, 5-dione-containing compositions for dyeing keratin fibres; their use in dyeing as couplers; dyeing process
FR2886135A1 (fr) * 2005-05-31 2006-12-01 Oreal Composition pour la teinture des fibrs keratiniques comprenant au moins un derive de diamino-n,n-dihydro- pyrazolone et un coupleur 2,3-diaminopyridine

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DE2359399C3 (de) 1973-11-29 1979-01-25 Henkel Kgaa, 4000 Duesseldorf Haarfärbemittel
DE3843892A1 (de) 1988-12-24 1990-06-28 Wella Ag Oxidationshaarfaerbemittel mit einem gehalt an diaminopyrazolderivaten und neue diaminopyrazolderivate
JPH0563124A (ja) 1991-09-03 1993-03-12 Mitsubishi Electric Corp 混成集積回路装置
DE4133957A1 (de) 1991-10-14 1993-04-15 Wella Ag Haarfaerbemittel mit einem gehalt an aminopyrazolderivaten sowie neue pyrazolderivate
DE4234887A1 (de) 1992-10-16 1994-04-21 Wella Ag Oxidationshaarfärbemittel mit einem Gehalt an 4,5-Diaminopyrazolderivaten sowie neue 4,5-Diaminopyrazolderivate und Verfahren zu ihrer Herstellung
DE4234885A1 (de) 1992-10-16 1994-04-21 Wella Ag Verfahren zur Herstellung von 4,5-Diaminopyrazol-Derivaten, deren Verwendung zum Färben von Haaren sowie neue Pyrazol-Derivate
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US3820948A (en) * 1968-04-17 1974-06-28 Therachemie Chem Therapeut Process of dyeing human hair based on pyrazolone compounds
US20010054205A1 (en) * 1996-03-22 2001-12-27 L'oreal Pyrazoline-3, 5-dione-containing compositions for dyeing keratin fibres; their use in dyeing as couplers; dyeing process
FR2886135A1 (fr) * 2005-05-31 2006-12-01 Oreal Composition pour la teinture des fibrs keratiniques comprenant au moins un derive de diamino-n,n-dihydro- pyrazolone et un coupleur 2,3-diaminopyridine

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