WO2024178529A1

WO2024178529A1 - Colorant composition for dyeing keratin fibers and kit comprising the same

Info

Publication number: WO2024178529A1
Application number: PCT/CN2023/078370
Authority: WO
Inventors: Mengyuan Huang; Yanmin ZHOU
Original assignee: L'oreal
Priority date: 2023-02-27
Filing date: 2023-02-27
Publication date: 2024-09-06
Also published as: FR3146066A1

Abstract

A colorant composition for dyeing keratin fibers and a kit comprising the same are disclosed. The colorant composition comprises i) at least one oxidative dye chosen from pyrazolone derivatives; ii) at least one sulphurous reducer; iii) at least one flavor essential oil without a reactive carbonyl group; and iv) at least one antioxidant.A non-therapeutic process for dyeing keratin fibers is also disclosed.

Description

COLORANT COMPOSITION FOR DYEING KERATIN FIBERS AND KIT COMPRISING THE SAME

TECHNIAL FIELD

The present invention relates to a cosmetic composition. In particular, the present invention relates to a colorant composition for dyeing keratin fibers and a kit comprising the same. The present invention also relates to a non-therapeutic process for dyeing keratin fibers.

BACKGROUND ART

Many people have for a long time sought to modify the color of their hair, and especially to dye it, for example, to mask their grey hair.

"Permanent" dyeing methods also known as oxidative dyeing, which use colorant compositions containing oxidative dye precursors, generally referred to as oxidation bases, such as ortho-or para-phenylenediamines, ortho-or para-aminophenols and heterocyclic compounds, have been developed for dyeing human keratin fibers in a long-lasting manner. These oxidation bases are colourless or weakly coloured compounds, which, when combined with oxidizing products, may give rise to coloured compounds via a process of oxidative condensation.

The dyeing product can comprise both at least one oxidative dye and at least one oxidant. For better use, the oxidative dye and the oxidant may be placed respectively in a multi-compartment package, and be mixed together immediately before use.

Pyrazolone derivatives dyes may be used in oxidative hair color product to achieve good stain free clear water (SFCW) performance. However, Pyrazolone derivatives dyes in hair color product may present stability issue in hair color product. In addition, fragrance is a necessary ingredient in hair coloration product, not only to cover unpleasant odor from raw material but also to provide a good smell for a comfortable usage experience. It has been found that fragrance or other flavor source (such as ethyl hydroxy pyrone) in formula may degrade pyrazolone derivatives dyes.

Thus there is a need to develop a stable composition for dyeing the hair comprising pyrazolone derivatives dyes or the like, which has good stain free clear water performance and good smell.

SUMMARY OF THE INVENTION

One aim of the present application is to provide a stable composition for dyeing the hair comprising pyrazolone derivatives dyes or the like, which has stain free clear water performance and good smell.

Another aim of the present application is to provide a process for dyeing the hair.

Thus, in a first aspect, the present invention provides a colorant composition for dyeing keratin fibers, comprising:

i) at least one oxidative dye chosen from pyrazolone derivatives;

ii) at least one sulphurous reducer;

iii) at least one flavor essential oil without a reactive carbonyl group; and

iv) at least one antioxidant.

The composition for dyeing keratin fibers according to the present invention is stable.

As used herein, “stable” means the pyrazolone derivative dye contained in the colorant composition does not decompose at a degree of more than 20 wt.%.

The colorant composition according to the present invention has good stain free clear water (SFCW) performance and good smell.

As used herein, good stain free clear water (SFCW) performance means that the water is transparent and clean after it has been used to rinse the dyed hair.

The colorant composition according to the present invention can be used to dye keratin fibers in combination with a developer composition.

In a second aspect, the present invention provides a kit for dyeing keratin fibers, comprising:

A) the colorant composition according to the first aspect of the present invention; and

B) a developer composition comprising at least one oxidant.

In a third aspect, the present invention provides a process for dyeing keratin fibers, comprising applying the kit according to the present invention onto the keratin fibers.

Other subjects and characteristics, aspects and advantages of the present invention will emerge even more clearly on reading the detailed description and the examples that follow.

DETAILD DESCRIPTION OF THE INVENTION

Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art the present invention belongs to. When the definition of a term in the present description conflicts with the meaning as commonly understood by those skilled in the art the present invention belongs to, the definition described herein shall apply.

As used herein, unless otherwise indicated, the limits of a range of values are included within this range, in particular in the expressions "between ... and …" and "from ... to ... " .

Moreover, the expression "at least one" used in the present description is equivalent to the expression "one or more" .

Throughout the instant application, the term “comprising” is to be interpreted as encompassing all specifically mentioned features as well as optional, additional, unspecified ones. As used herein, the use of the term “comprising” also discloses the embodiment wherein no features other than the specifically mentioned features are present (i.e. “consisting of” ) .

Unless otherwise specified, all numerical values expressing amount of ingredients and the like which are used in the description and claims are to be understood as being modified by the term “about” . Accordingly, unless indicated to the contrary, the numerical values and parameters described herein are approximate values which are capable of being changed according to the desired purpose as required.

For the purposes of the present invention, the term "keratin fibers" includes animal keratin fibers and human keratin fibers such as the hair.

All percentages in the present invention refer to weight percentage, unless otherwise specified.

Pyrazolone derivatives

According to the first aspect, the colorant composition of the present invention comprises at least one oxidative dye chosen from pyrazolone derivatives.

Preferably, the oxidative dye is selected from

- pyrazolones substituted with at least one aryl and/or at least one alkyl, preferably C1-C4 alkyl, the number of substituents aryl and alkyl is not more than 3, preferably, the aryl is an unsubstituted phenyl or a phenyl substituted with at least one alkyl, preferably C1-C4 alkyl; and

- diamino-N, N-dihydropyrazolopyrazolones and especially those described in patent application FR-A-2 886 136.

Preferably, the oxidative dye is selected from

- phenyl methyl pyrazolone (PMP) , e.g., 3-methyl-1-phenyl-5-pyrazolone;

- 2, 3-diamino-6, 7-dihydro-1H, 5H-pyrazolo [1, 2-a] pyrazol-1-one,

- 2-amino-3-ethylamino-6, 7-dihydro-1 H, 5H-pyrazolo [1, 2-a] pyrazol-1-one,

- 2-amino-3-isopropylamino-6, 7-dihydro-1H, 5H-pyrazolo [1, 2-a] pyrazol-1-one,

- 2-amino-3- (pyrrolidin-1-yl) -6, 7-dihydro-1H, 5H-pyrazolo [1, 2-a] pyrazol-1-one,

- 4, 5-diamino-1, 2-dimethyl-1, 2-dihydropyrazol-3-one,

- 4, 5-diamino-1, 2-diethyl-1, 2-dihydropyrazol-3-one,

- 4, 5-diamino-1, 2-bis (2-hydroxyethyl) -1, 2-dihydropyrazol-3-one,

- 2-amino-3- (2-hydroxyethyl) amino-6, 7-dihydro-1 H, 5H-pyrazolo [1, 2-a] pyrazol-1-one,

- 2-amino-3-dimethylamino-6, 7-dihydro-1H, 5H-pyrazolo [1, 2-a] pyrazol-1-one,

- 2, 3-diamino-5, 6, 7, 8-tetrahydro-1 H, 6H-pyridazino [1, 2-a] pyrazol-1-one,

- 4-amino-1, 2-diethyl-5- (pyrrolidin-1-yl) -1, 2-dihydropyrazol-3-one,

- 4-amino-5- (3-dimethylaminopyrrolidin-1-yl) -1, 2-diethyl-1, 2-dihydropyrazol-3-one;

- 2, 3-diamino-6-hydroxy-6, 7-dihydro-1 H, 5H-pyrazolo [1, 2-a] pyrazol-1-one.

In some particularly preferred embodiments, the colorant composition according to the present invention comprises phenyl methyl pyrazolone.

Advantageously, the oxidative dye chosen from pyrazolone derivatives is present in the colorant composition of the present invention in an amount ranging from 0.01 wt. %to 2 wt. %, preferably from 0.1 wt. %to 1 wt. %, and more preferably from 0.3 wt. %to 0.7 wt. %, relative to the total weight of the colorant composition.

Sulphurous reducers

According to the first aspect, the colorant composition of the present invention comprises at least one sulphurous reducer.

Preferably, the sulphurous reducer is selected from 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-acetylcysteine and its salts; ammonium thioglycolate, glycerol monothioglycolate, or a combination thereof.

More preferably, the sulphurous reducer is selected from sodium metabisulfite, thioglycolic acid, dithio glycolic acid or a combination thereof.

In some particularly preferred embodiments, the colorant composition according to the present invention comprises sodium metabisulfite, or its combination with thioglycolic acid.

Advantageously, the sulphurous reducer is present in the colorant composition of the present invention in an amount ranging from 0.01 wt. %to 5 wt. %, preferably from 0.1 wt. %to 3 wt. %, and more preferably from 0.5 wt. %to 2 wt. %, relative to the total weight of the colorant composition.

Flavor essential oils without a reactive carbonyl group

According to the first aspect, the colorant composition of the present invention comprises at least one flavor essential oil without a reactive carbonyl group.

As examples of flavor essential oils without a reactive carbonyl group, mention can be made of mentha piperita (peppermint) oil, lavandula hybrida oil, pelargonium graveolens flower oil, sweet orange essential oil, chamomile essential oil, thyme essential oil, eucalyptus essential oil and a combination thereof.

Preferably, the flavor essential oil without a reactive_carbonyl group is selected from mentha piperita (peppermint) oil, lavandula hybrida oil, pelargonium graveolens flower oil, and a combination thereof.

The inventors have found unexpectedly that with the presence of flavor essential oil without a reactive carbonyl group, the colorant composition has good stability and good smell.

Advantageously, the flavor essential oil without a reactive carbonyl group is present in the colorant composition of the present invention in an amount ranging from 0.01 wt. %to 2 wt. %, preferably from 0.1 wt. %to 1.5 wt. %, and more preferably from 0.3 wt. %to 1 wt. %, relative to the total weight of the colorant composition.

Antioxidants

According to the first aspect, the colorant composition according to the present invention comprises at least one antioxidant.

The antioxidants used can be one or more of natural exogenous phytochemical antioxidants such as phenols and carotenoids.

The antioxidants used can be one or more of flavonoids. Flavonoids constitute a large class of more than 5, 000 polyphenolic phytochemicals with antioxidant properties that act by direct free radical scavenging. 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 as antioxidants, 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. In addition, it is also possible to use extracts of Myrciaria dubia, acerola, emblica officinalis, and bioflavonoids from rose hips and citrus, including water-soluble bioflavonoids such as hesperidin methyl chalcone.

Other 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-α-tocotrienol, d-β-tocotrienol, d-γ-tocotrienol, d-δ-tocotrienol) and vitamin E (α-tocopheryl acetate) ) . These compounds can be isolated from natural sources, or prepared by synthetic means. 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.

In addition, carotenoids, especially lutein types, are also useful antioxidants that can be used. Lutein-type carotenoids include molecules such as lutein, canthaxantin, cryptoxanthin, zeaxanthin and astaxanthin.

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. In addition, 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. Those skilled in the art will appreciate that certain portions of the plant may contain higher natural levels of anthocyanins, and thus these moieties are used to obtain the desired anthocyanins. In some cases, 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. Without limiting the mode of action of the present invention, 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, α-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 lignan diglucoside, sesamin, sesame phenol, Silybin, silymarin, theaflavins, theaflavins digallate, Thmoquinone, Trolox, tyrosol, polyunsaturated fatty acids and sulfur-based antioxidants such as methionine or lipoic acid.

Advantageously, the antioxidant is selected from ascorbic acid, erythorbic acid, sodium ascorbate, sodium erythorbate, ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl glucoside, glucosamine ascorbate, ascorbyl acetate, and a combination thereof.

In some particularly preferred embodiments, the colorant composition according to the present invention comprises erythorbic acid.

Advantageously, the antioxidant is present in the colorant composition of the present invention in an amount ranging from 0.01 wt. %to 5 wt. %, preferably from 0.1 wt. %to 3 wt. %, and more preferably from 0.5 wt. %to 2.5 wt. %, relative to the total weight of the colorant composition.

Adjuvants

The colorant composition according to the present invention may also comprise one or more cosmetic adjuvants.

For example, the colorant composition 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, sequestrants, surfactants, plasticizers, solubilizers, acidifying agents, opacifiers, and preserving agents.

Needless to say, aperson skilled in the art will take care to select this or these optional additional compound (s) such that the advantageous properties intrinsically associated with the invention are not, or are not substantially, adversely affected by the envisaged addition (s) .

Solvents

The colorant composition according to the present invention can advantageously comprise one or more solvent (s) , e.g., water and/or organic solvent.

Examples of water-soluble organic solvents that may be mentioned 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 C₁-C₄ alkyl ethers, for instance diethylene glycol monoethyl ether or monobutyl ether, alone or as a mixture.

Advantageously, the colorant composition according to the present invention comprises water, in a content of more than 40%by weight relative to the total weight of the colorant composition.

According to a particularly embodiment, the colorant composition according to the present invention comprises, relative to the total weight of the colorant composition,

i) from 0.3 wt. %to 2 wt. %of phenyl methyl pyrazolone;

ii) from 0.5 wt. %to 2 wt. %of at least one sulphurous reducer selected from sodium metabisulfite, thioglycolic acid, dithio glycolic acid or a combination thereof;

iii) from 0.3 wt. %to 1 wt. %of at least one flavor essential oil without a reactive carbonyl group selected from mentha piperita (peppermint) oil, lavandula hybrida oil, pelargonium graveolens flower oil, and a combination thereof; and

iv) from 0.5 wt. %to 2.5 wt. %of an antioxidant selected from ascorbic acid, erythorbic acid, sodium ascorbate, sodium erythorbate, ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl glucoside, glucosamine ascorbate, ascorbyl acetate, and a combination thereof.

Kits

According to the second aspect, the kit of the present invention comprises:

B) a developer composition comprising at least one oxidant.

Developer composition

The developer composition according to the present invention comprises an oxidant.

The term "oxidant" is intended to mean an oxidant other than atmospheric oxygen. More particularly, the oxidant is selected from 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.

Advantageously, the oxidant is hydrogen peroxide.

Advantageously, the oxidant is present in the developer composition in an amount ranging from 0.1 wt. %to 50 wt. %, more preferably from 0.5 wt. %to 20 wt. %, still more preferably from 1 wt. %to 15 wt. %, based on the total weight of the developer composition.

Solvents

The developer composition of the present invention may comprise one or more solvent (s) , e.g., water and/or organic solvent. The useful solvent can be selected from those discussed for the “solvent” of the colorant composition above.

The colorant composition and the developer composition of the kit can independently use same or different solvents, respectively.

When water is used as a solvent in the developer composition according to the invention, it is preferably used in a content of ranging from 40 wt. %to 95 wt. %, more preferentially from 50 wt. %to 90 wt. %, or from 60 wt. %to 85 wt. %, relative to the total weight of the developer composition.

Examples of water-soluble organic solvents that may be mentioned 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 wt. %and 10 wt. %, preferably between 0.1 wt. %and 5 wt. %, or between 0.5 wt. %and 1 wt. %, relative to the total weight of the developer composition according to the present invention.

Preferably, the developer composition is preferably placed separate from the colorant composition.

Use

According to the third aspect, the present invention provides a process for dyeing keratin fibers, comprising applying the kit according to the present invention onto the keratin fibers.

In particular, the keratin fibers are the hair.

According to a preferred embodiment, the process of the present invention comprises mixing the colorant composition and the developer composition immediately before use, and applying the mixture obtained as described above to the keratin fibers.

More particularly, by “mixing” , it is intended to mean the action of putting the colorant composition of the present invention into a container or palm, together with the developer composition as described above, with or without stirring them.

The mixed compositions, including the colorant composition and the developer composition, 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℃ and preferably between 20 and 60℃. After the treatment, 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 abovementioned 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.

EXAMPLES

The following examples serve to illustrate the present invention without, however, being limiting in nature.

Main raw materials used, trade names and supplier thereof were listed in Table 1.

Table 1

Inventive Examples 1-5 and Comparative Examples 1-5

Compositions according to inventive examples (IE) 1-5 and comparative examples (CE) 1-5 were prepared with the ingredients listed in Table 2 (the contents were expressed as weight percentages of ingredients with regard to the total weight of each composition, unless otherwise indicated) :

Table 2

MENTHA PIPERITA (PEPPERMINT) OIL used contains compound of the following structure as main ingredient (Menthol) :

LAVANDULA HYBRIDA OIL used contains compound of the following structure as main ingredient (Linalool and Linalyl acetate) :

FRAGRANCE 1 is not a flavor essential oil without a reactive carbonyl group and comprises compound of the following structure as main ingredient:

Composition of invention examples 1-5 are compositions according to the present invention.

Composition of comparative example 1 does not comprise sulphurous reducers.

Composition of comparative example 2 does not comprise antioxidants.

Compositions of comparative examples 3-5 do not comprise essential oil.

Preparation procedure:

The compositions listed above were prepared as follows, taking the composition of invention example 1 as an example:

1) . adding ERYTHORBIC ACID and THIOGLYCOLIC ACID, SODIUM METABISULFITE into water and mixing for 15 minutes;

2) . adding dye (p-PHENYLENEDIAMINE, RESORCINOL, and 2, 4-DIAMINOPHENOXYETHANOL HCl) into the system obtained and mixing for 15 minutes;

3) . adding MENTHA PIPERITA (PEPPERMINT) OIL into the system obtained and mixing for 10 minutes;

4) . adding phenyl methyl pyrazolone into the system obtained and mixing for 15 minutes to obtain the composition.

A developer composition hereinafter was prepared with the ingredients listed in Table 3 (the contents were expressed as weight percentages of ingredients with regard to the total weight of the developer composition, unless otherwise indicated) .

Table 3

Evaluation:

A. Stability of phenyl methyl pyrazolone

Stability of phenyl methyl pyrazolone in each colorant composition prepared above was evaluated based on the loss percentage of phenyl methyl pyrazolone tested by LC-MS at room temperature (25℃) . The results are summarized in Table 4, wherein the loss by weight percentage is calculated according to the following equation:

Loss (wt. %) = (1-test value by weight/theoretical value by weight) *100%

In Table 4, T₀ stands for Storage＜48h after preparation, T_1M stands for Storage for 1 month after preparation.

If the loss by weight percentage after storage for 1 month and/or that within 48 hours after preparation is not more than 20 wt. %, the stability will be evaluated as "PASS" , otherwise, it will be evaluated as "FAIL" .

B. Stain free clear water (SFCW)

Stain free clear water performance was evaluated according to a method described below:

1) applying 1g of each colorant composition and 1 g of the developer composition on 2g hair swatches for 15 minutes;

2) Rinsing the hair swatches with 400 ml water, and take a picture of rising water.

Stain free clear water will be evaluated as “OK” if the rinsing water is transparent and clean, and could be acceptable if the rinsing water with weak reflect. Stain free clear water will be evaluated as “Not OK” if the toner of rinsing water is dark as light brown to black.

C. Smell

Smell performance of each colorant composition prepared above was evaluated according to a method described below:

1) weighting 5g of the tested sample on a watch-glass,

2) carrying out a blind sniff test by 10 skin experts,

3) inviting the expects to give a score for each sample according to the following standard and taking the average score as a final score:

5=Very good smell,

4=Good smell,

3=Acceptable,

2=Not good coverage/Bad smell,

1=No coverage/Very bad smell.

The results were summarized in Table 4.

Table 4

It can be seen from Table 4 that compositions according to the present invention are stable, and have good stain free clear water performance and good smell.

Claims

A colorant composition for dyeing keratin fibers, comprising:

i) at least one oxidative dye chosen from pyrazolone derivatives;

ii) at least one sulphurous reducer;

iii) at least one flavor essential oil without a reactive carbonyl group; and

iv) at least one antioxidant.
The colorant composition according to claim 1, wherein the oxidative dye is selected from pyrazolones substituted with at least one aryl and/or at least one alkyl, preferably C1-C4 alkyl, the number of substituents aryl and alkyl is not more than 3, and

diamino-N, N-dihydropyrazolopyrazolones; preferably the oxidative dye is phenyl methyl pyrazolone.
The colorant composition according to claim 1 or 2, wherein the oxidative dye chosen from pyrazolone derivatives is present in an amount ranging from 0.01 wt. %to 2 wt. %, preferably from 0.1 wt. %to 1 wt. %, and more preferably from 0.3 wt. %to 0.7 wt. %, relative to the total weight of the colorant composition.
The colorant composition according to any of claims 1-3, wherein the sulphurous reducer is selected from 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-acetylcysteine and its salts; ammonium thioglycolate, glycerol monothioglycolate, or a combination thereof, preferably, the sulphurous reducer is selected from sodium metabisulfite, thioglycolic acid, dithio glycolic acid or a combination thereof.
The colorant composition according to any of claims 1-4, wherein the sulphurous reducer is present in an amount ranging from 0.01 wt. %to 5 wt. %, preferably from 0.1 wt. %to 3 wt. %, and more preferably from 0.5 wt. %to 2 wt. %, relative to the total weight of the colorant composition.
The colorant composition according to any of claims 1-5, wherein the flavor essential oil without a reactive_carbonyl group is selected from mentha piperita (peppermint) oil, lavandula hybrida oil, pelargonium graveolens flower oil, and a combination thereof.
The colorant composition according to any of claims 1-6, wherein the flavor essential oil without a reactive_carbonyl group is present in an amount ranging from 0.01 wt. %to 2 wt. %, preferably from 0.1 wt. %to 1.5 wt. %, and more preferably from 0.3 wt. %to 1 wt. %, relative to the total weight of the colorant composition.
The colorant composition according to any of claim 1-7, wherein the antioxidant is selected from ascorbic acid, erythorbic acid, sodium ascorbate, sodium erythorbate, ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl glucoside, glucosamine ascorbate, ascorbyl acetate, and a combination thereof.
The colorant composition according to any of claim 1-8, wherein the antioxidant is present in an amount ranging from 0.01 wt. %to 5 wt. %, preferably from 0.1 wt. %to 3 wt. %, and more preferably from 0.5 wt. %to 2.5 wt. %, relative to the total weight of the colorant composition.
The colorant composition according to claim 1, comprising, relative to the total weight of the colorant composition:

i) from 0.3 wt. %to 0.7 wt. %of phenyl methyl pyrazolone;

ii) from 0.5 wt. %to 2 wt. %of at least one sulphurous reducer selected from sodium metabisulfite, thioglycolic acid, dithio glycolic acid or a combination thereof;

iii) from 0.3 wt. %to 1 wt. %of at least one flavor essential oil without areactive_carbonyl group selected from mentha piperita (peppermint) oil, lavandula hybrida oil, pelargonium graveolens flower oil, and a combination thereof; and

iv) from 0.5 wt. %to 2.5 wt. %of an antioxidant selected from ascorbic acid, erythorbic acid, sodium ascorbate, sodium erythorbate, ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl glucoside, glucosamine ascorbate, ascorbyl acetate, and a combination thereof.
A kit for dyeing keratin fibers, comprising:

A) the colorant composition according to any of claims 1-10; and

B) a developer composition comprising at least one oxidant.
The kit according to claim 11, wherein the oxidant is selected from 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 kit according to claims 11 or 12, wherein the oxidant is present in an amount ranging from 0.1 wt. %to 50 wt. %, more preferably from 0.5 wt. %to 20 wt. %, still more preferably from 1 wt. %to 15 wt. %, based on the total weight of the developer composition.
A process for dyeing keratin fibers, comprising applying the kit according to claim 12 or 13 onto the keratin fibers.