WO2021259974A1 - Composition comprenant un polymère comprenant au moins une unité de (méth)acrylamide cationique, une silicone particulière et un oxydant chimique et/ou un colorant d'oxydation - Google Patents

Composition comprenant un polymère comprenant au moins une unité de (méth)acrylamide cationique, une silicone particulière et un oxydant chimique et/ou un colorant d'oxydation Download PDF

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WO2021259974A1
WO2021259974A1 PCT/EP2021/067091 EP2021067091W WO2021259974A1 WO 2021259974 A1 WO2021259974 A1 WO 2021259974A1 EP 2021067091 W EP2021067091 W EP 2021067091W WO 2021259974 A1 WO2021259974 A1 WO 2021259974A1
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weight
cationic
meth
alkyl
acrylamide
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PCT/EP2021/067091
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English (en)
Inventor
Nilmoni Ghosh
Sangeeta GAIKWAD
Shubhrajit NAG
Sandip KEDAR
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L'oreal
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Priority claimed from FR2008394A external-priority patent/FR3113241B1/fr
Application filed by L'oreal filed Critical L'oreal
Publication of WO2021259974A1 publication Critical patent/WO2021259974A1/fr

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    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
    • 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
    • A61Q5/08—Preparations for bleaching the hair
    • 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
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns

Definitions

  • composition comprising a polymer comprising at least one cationic (meth)acrylamide unit, a particular silicone and a chemical oxidizing agent and/or an oxidation dye
  • the present invention relates to a cosmetic composition for treating keratin fibres, and in particular human keratin fibres such as hair, which comprises one or more polymers comprising one or more cationic or quaternized acrylamide and/or methacrylamide unit(s), a specific oil-in-water-type silicone emulsion, and one or more chemical oxidizing agent(s) and/or one or more oxidation dye(s).
  • the invention also relates to a cosmetic treatment process, especially for dyeing and/or lightening keratin fibres using this composition.
  • the present invention also relates to a particular process for dyeing keratin fibres.
  • the present invention also relates to a particular process for lightening keratin fibres.
  • the invention also relates to the use of such a composition for dyeing and/or lightening keratin fibres.
  • the invention relates to a kit comprising at least two compartments, a first compartment comprising a first composition comprising one or more oxidation dye(s), a second compartment comprising a second composition comprising one or more chemical oxidizing agent(s), one or more polymers comprising one or more cationic or quaternized acrylamide and/or methacrylamide unit(s), being comprised in the first and/or second composition, and a specific oil-in- water-type silicone emulsion being comprised in the first and/or second composition.
  • oxidizing compositions or dye compositions containing oxidation dye precursors which are generally known as “oxidation bases”, in particular ortho- or para-phenylenediamines, ortho- or para-aminophenols and heterocyclic bases.
  • Oxidation dye precursors are compounds that are initially uncoloured or sparingly coloured, which develop their dyeing power on the hair in the presence of oxidizing agents, leading to the formation of coloured compounds.
  • the formation of these coloured compounds results either from an oxidative condensation of the “oxidation bases” with themselves, or from an oxidative condensation of the “oxidation bases” with coloration-modifying compounds, or “couplers”, which are generally present in the dye compositions used in oxidation dyeing and are represented more particularly by meta-phenylenediamines, meta- aminophenols, meta-diphenols and certain heterocyclic compounds.
  • compositions should give satisfactory silicone deposit on the keratin fibres.
  • the subject of the invention is a cosmetic composition comprising: a. one or more polymers comprising one or more cationic or quaternized acrylamide and/or methacrylamide unit(s); b. an oil-in-water emulsion having D50 particle size of less than 350 nm and comprising:
  • a silicone mixture comprising (i) one or more tri alkyl si ly 1 terminated dialkylpolysiloxane(s) having a viscosity of from 40,000 to less than 100,000 mPa.s at 25°C and (ii) one or more amino silicone(s) having a viscosity of from 1,000 to 15,000 mPa.s at 25°C and an amine value of from 2 to 10 mg of KOH per gram of amino silicone,
  • emulsifiers comprising one or more nonionic emulsifiers, wherein the mixture of emulsifiers has a HLB value of from 10 to 16, and
  • This cosmetic composition when applied on keratin fibres, in particular human keratin fibres such as hair, provides good lightening performances and/or good dyeing performances such as intensity, chromaticity, selectivity, and leads to an improvement of the condition and quality of hair, in terms of hair feel (e.g. smooth feel, soft feel, conditioned feel) and hair manageability (e.g., no or less frizz, styleability/shapeability, combing, detangling, desirable volume).
  • hair feel e.g. smooth feel, soft feel, conditioned feel
  • hair manageability e.g., no or less frizz, styleability/shapeability, combing, detangling, desirable volume.
  • This cosmetic composition allows increasing the silicone deposition on hair when compared to a similar composition which does not contain the specific polymer a.
  • the present invention also relates to a cosmetic treatment process, in particular for dyeing and/or lightening keratin fibres, preferably human keratin fibres such as the hair, using this composition.
  • the present invention also relates to a particular process for dyeing keratin fibres.
  • the present invention also relates to a particular process for lightening keratin fibres.
  • composition according to the invention for dyeing and/or lightening keratin fibres.
  • the present invention also relates to a kit comprising at least two compartments, a first compartment comprising a first composition comprising one or more oxidation dye(s), a second compartment comprising a second composition comprising one or more chemical oxidizing agent(s), the first and/or second composition comprising one or more polymers comprising one or more cationic or quaternized acrylamide and/or methacrylamide unit(s) as defined above, and the specific oil-in-water emulsion as defined above.
  • a kit comprising at least two compartments, a first compartment comprising a first composition comprising one or more oxidation dye(s), a second compartment comprising a second composition comprising one or more chemical oxidizing agent(s), the first and/or second composition comprising one or more polymers comprising one or more cationic or quaternized acrylamide and/or methacrylamide unit(s) as defined above, and the specific oil-in-water emulsion as defined above.
  • Polymer(s) comprising at least one cationic or quaternized (meth)acrylamide unit
  • the first essential component of the cosmetic composition according to the present invention is one or more polymer(s) comprising one or more cationic or quaternized (meth)acrylamide unit(s). These polymers are non-silicones, i.e. they do not contain any silicon (Si) atom.
  • Polymers comprising one or more cationic or quaternized (meth)acrylamide unit(s) can be cationic and/or amphoteric polymers.
  • cationic and/or amphoteric polymer(s) it is understood one or more cationic polymers, one or more amphoteric polymers or the mixture of one or more cationic polymers, and of one or more amphoteric polymers.
  • the polymer(s) comprising one or more cationic or quaternized (meth)acrylamide units may be chosen from cationic polymers, amphoteric polymers and mixtures thereof. Most preferably, they are chosen from cationic polymers.
  • the cationic charge density of the polymers comprising one or more cationic or quaternized (meth)acrylamide units may preferably be lower than or equal to 6 meq/g, more preferentially lower than or equal to 5 meq/g, and better still lower than or equal to 4 meq/g.
  • This cationic charge density advantageously ranges from 0.5 to 6 meq/g, better still from 1 to 5 meq/g, and even more preferably from 1.5 to 4 meq/g.
  • cationic polymer means any polymer comprising cationic groups and/or groups that can be ionized to cationic groups, and not comprising anionic groups and/or groups that can be ionized to anionic groups.
  • the cationic polymer is hydrophilic or amphiphilic.
  • the preferred cationic polymers are chosen from those that contain units comprising primary, secondary, tertiary and/or quaternary amine groups that may either form part of the main polymer chain or may be borne by a side substituent directly connected thereto.
  • the polymers comprising one or more cationic or quaternized (meth)acrylamide units that can be used in the present invention are preferably chosen from homopolymers or copolymers comprising at least one of the units of the following formulae: in which:
  • - Ri which may be identical or different, denotes a hydrogen atom or a CH3 radical
  • R which may be identical or different, denotes a linear or branched C1-C12 alkyl radical, preferably a linear C1-C6 alkyl radical, optionally substituted by one or more hydroxyl radicals;
  • R5 , R 6 and R7 which may be identical or different, denote a linear or branched Ci-Cis alkyl radical or a benzyl radical, preferably a linear or branched C1-C6 alkyl radical;
  • - R-8 and R » which may be identical or different, denote a hydrogen atom or a linear or branched C1-C6 alkyl radical, preferably methyl or ethyl;
  • - Y denotes an anion derived from a mineral or organic acid or a halide, preferably bromide, chloride, acetate, borate, citrate, tartrate, bisulfate, bisulfite, methosulfate, sulfate or phosphate anion.
  • the polymers comprising one or more cationic or quaternized (meth)acrylamide unit(s) may further contain one or more units derived from comonomers that may be selected from the families of acrylamides, methacrylamides, diacetone acrylamides, acrylic or methacrylic acids or esters thereof, vinyllactams such as vinylpyrrolidone or vinylcaprolactam, and vinyl esters, preferably selected from the families of acrylamide and methacrylamides, and more preferentially acrylamide or methacrylamide.
  • comonomers may be selected from the families of acrylamides, methacrylamides, diacetone acrylamides, acrylic or methacrylic acids or esters thereof, vinyllactams such as vinylpyrrolidone or vinylcaprolactam, and vinyl esters, preferably selected from the families of acrylamide and methacrylamides, and more preferentially acrylamide or methacrylamide.
  • vinyllactams such as vinylpyrrolidone or vinyl
  • Chloride such as the product N-DURHANCE A-1000 from ASHLAND
  • the polymers comprising one or more cationic or quaternized (meth)acrylamide units that can be used in the present invention can also be chosen from amphoteric polymers.
  • amphoteric polymer means any polymer comprising cationic groups and/or groups that can be ionized to cationic groups, and comprising anionic groups and/or groups that can be ionized to anionic groups.
  • Amphoteric polymers can be chosen more particularly from amphoteric polymers comprising a repetition of:
  • the units derived from a monomer of (meth)acrylamide type (i) are units of structure (VI) below: in which:
  • - Ri denotes a hydrogen atom or CTb radical
  • R2 denotes a NR3R4 radical, wherein R3 and R4, which may be identical or different, denote a hydrogen atom or a linear or branched C1-C12 alkyl radical, optionally substituted by one or more hydroxyl radicals, preferably R2 denotes an amino, a dimethylamino, a tert- butylamino, a dodecylamino or a -NH-CH2OH radical.
  • the said amphoteric polymer comprises a repetition of only one unit of formula (VI).
  • the units derived from a monomer of (meth)acrylamidoalkyltrialkylammonium type (ii) are units of structure (VII) below: in which:
  • - Ri denotes a hydrogen atom or CH3 radical
  • R 6 and R7 which may be identical or different, denote a linear or branched C1-C 6 alkyl radical, preferably a linear or branched C1-C4 alkyl radical;
  • - n denotes an integer ranging from 1 to 6, preferably from 1 to 4;
  • - Y denotes an anion derived from a mineral or organic acid or a halide, preferably bromide, chloride, acetate, borate, citrate, tartrate, bisulfate, bisulfite, methosulfate, sulfate or phosphate anion.
  • the said amphoteric polymer comprises a repetition of only one unit of formula (VII).
  • the ones that are preferred are those derived from the methacrylamidopropyltrimethylammonium chloride monomer, for which Ri denotes a methyl radical, n is equal to 3, Rs, R6 and R7 denote a methyl radical, and Y denotes a chloride anion.
  • the units derived from a monomer of (meth)acrylic acid type (iii) are units of formula (VIII): in which:
  • - Ri denotes hydrogen atom or CH3 radical
  • R2 denotes a hydroxyl radical or a NR3R4 radical, wherein R3 and R4, which may be identical or different, denote a hydrogen atom or a linear or branched C1-C12 alkyl radical optionally substituted by a sulfonic group (-SO 3 H), preferably R2 denotes a -NH-C(CH3)2-CH2-S03H radical.
  • the preferred units of formula (VIII) correspond to the acrylic acid, methacrylic acid and 2-acrylamino-2-methylpropanesulfonic acid monomers.
  • the unit derived from a monomer of (meth)acrylic acid type of formula (VIII) is that derived from acrylic acid, for which Ri denotes a hydrogen atom and R2 denotes a hydroxyl radical.
  • the acidic monomer(s) of (meth)acrylic acid type may be non- neutralized or partially or totally neutralized with an organic or mineral base.
  • the said amphoteric polymer comprises a repetition of only one unit of formula (VIII).
  • the amphoteric polymer(s) of this type comprise at least 30 mol% of units derived from a monomer of (meth)acrylamide type (i). Preferably, they comprise from 30 mol% to 70 mol% and more preferably from 40 mol% to 60 mol% of units derived from a monomer of (meth)acrylamide type.
  • the content of units derived from a monomer of (meth)acrylamidoalkyltrialkylammonium type (ii) may advantageously be from 10 mol% to 60 mol% and preferentially from 20 mol% to 55 mol%.
  • the content of units derived from an acidic monomer of (meth)acrylic acid type (iii) may advantageously be from 1 mol% to 20 mol% and preferentially from 5 mol% to 15 mol%.
  • amphoteric polymer of this type comprises:
  • Amphoteric polymers of this type may also comprise additional units, other than the units derived from a monomer of (meth)acrylamide type, of (meth)acrylamidoalkyltrialkylammonium type and of (meth)acrylic acid type as described above.
  • the said amphoteric polymers consist solely of units derived from monomers (i) of (meth)acrylamide type, (ii) of (meth)acrylamidoalkyltrialkylammonium type and (iii) of (meth)acrylic acid type.
  • amphoteric polymers that are particularly preferred, mention may be made of acrylamide/ methacrylamidopropyltrimethylammonium chloride/ acrylic acid terpolymers. Such polymers are listed in the CTFA Dictionary (International Cosmetic Ingredient Dictionary) under the name Polyquaternium 53. Corresponding products are especially sold under the names Merquat 2003 and Merquat 2003 PR by the company Nalco.
  • amphoteric polymers Another preferred type of amphoteric polymers is the polymer comprising a repetition of:
  • (iii) one or more units derived from an acidic monomer of (meth)acrylic acid type.
  • the monomer of (meth)acrylamidoalkyltrialkylammonium type and the acidic monomer of (meth)acrylic acid type (monomers (ii) and (iii) respectively) are as described above.
  • the non ionic monomers (i) of (meth)acrylate type are preferably chosen from C1-C4 alky acrylates and methacrylates.
  • a preferred monomer is methyl acrylate.
  • amphoteric polymers As particularly preferred examples of such amphoteric polymers, mention may be made of acrylic acid / methylacrylamidopropyltrimethylammonium chloride/ methyl acrylates terpolymers. Such polymers are listed in the CTFA International Cosmetic Ingredient Dictionary under the name polyquaternium 47. Corresponding products are especially sold under the names Merquat 2001 and Merquat 2001N by the company Nalco.
  • the polymer(s) comprising one or more cationic or quaternized (meth)acrylamide units are preferably chosen from:
  • (meth)acrylamido(Ci-C 6 alkyl)tri(Ci-C4 alkyl) ammonium halide /(meth)acrylamide/(meth)acrylic acid terpolymers preferably (meth)acrylamidopropyltrimonium chloride / (meth)acrylamide / (meth)acrylic acid terpolymers, more preferably acrylamide/ methacrylamidopropyltrimethylammonium chloride/ acrylic acid terpolymers,
  • (meth)acrylamido(Ci-C 6 alkyl)tri(Ci-C4 alkyl) ammonium halide/ (C1-C6 alkyl) (meth)acrylate / (meth)acrylic acid terpolymers preferably (meth)acrylamidopropyltrimonium chloride / (C1-C6 alkyl) (meth)acrylate / (meth)acrylic acid terpolymers; more preferably acrylic acid / methylacrylamidopropyltrimethyl- ammonium chloride/ methyl acrylates terpolymers, and mixtures thereof.
  • the polymer(s) comprising one or more cationic or quaternized (meth)acrylamide units are preferably chosen from: (meth)acrylamido(Ci-C 6 alkyl)tri(Ci-C4 alkyl) ammonium halide/ (meth)acrylamide copolymers, preferably (meth)acrylamide- propyltrimonium chloride/ (meth)acrylamide copolymers, and most preferably acrylamidopropyltrimonium chloride/ acrylamide copolymers.
  • the total amount of polymer(s) comprising one or more cationic or quaternized (meth)acrylamide units present in the cosmetic composition of the present invention advantageously ranges from 0.01 to 5% by weight, preferably from 0.015 to 4% by weight, more preferentially from 0.02 to 2% by weight, better still from 0.03 to 1% by weight, and even more preferentially from 0.04 to 0.5% by weight, relative to the total weight of the cosmetic composition.
  • the cosmetic composition according to the invention comprises an oil-in-water (or silicone-in-water) emulsion having D50 particle size of less than 350 nm and comprising:
  • a silicone mixture comprising (i) a tri alkyl sily 1 terminated dialkylpolysiloxane having a viscosity of from 40,000 to less than 100,000 mPa.s at 25°C and (ii) an amino silicone having a viscosity of from 1,000 to 15,000 mPa.s at 25°C and an amine value of from 2 to 10 mg of KOH per gram of amino silicone;
  • - a mixture of emulsifiers comprising one or more nonionic emulsifiers, wherein the mixture of emulsifiers has a HLB value of from 10 to 16; and - water.
  • one liquid phase is dispersed in the other liquid phase (the continuous phase); in the present invention, the silicone mixture, or silicone phase, is dispersed in the continuous aqueous phase.
  • the silicone mixture comprises one or more tri alkyl sily 1 terminated dialkylpolysiloxanes, that are preferably of formula (IX):
  • R 3SiO(R , 2 SiO)pSiR , 3 (IX), wherein: - R’, identical or different, is a monovalent hydrocarbon radical having from 1 to 18 carbon atoms, preferably from 1 to 6 carbon atoms, even better from 1 to 3 carbon atoms, more preferably methyl, and
  • - p is an integer of from 500 to 2,000, preferably of from 1,000 to 2,000.
  • the tri alkyl si ly 1 terminated (or end-blocked or a, co-position) dialkylpolysiloxanes according to the invention have a viscosity of from 40,000 to less than 100,000 mPa.s (100,000 excluded) at 25°C, preferably a viscosity of from 40,000 to 70,000 mPa.s at 25°C, more preferably a viscosity of from 51,000 to 70,000 mPa.s at 25°C.
  • the tri alkyl si ly 1 terminated dialkylpolysiloxanes according to the invention are preferably linear but may contain additionally to the R’2Si02/2 units (D-units) in formula (IX), RS1O3/2 units (T-units) and/or S1O4/2 units (Q-units), wherein R’, same or different, is a monovalent hydrocarbon radical having from 1 to 18 carbon atoms.
  • R’ are alkyl radicals, preferably Ci-Cis alkyl radicals, such as the methyl, ethyl, n-propyl, isopropyl, 1-n-butyl, 2-n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl and tert-pentyl radicals, hexyl radicals, such as the n-hexyl radical, heptyl radicals such as the n-heptyl radical, octyl radicals such as the n-octyl radical and isooctyl radicals, such as the 2,2,4- trimethylpentyl radical, nonyl radicals, such as the n-nonyl radicals, decyl radicals, such as the n-decyl radical, dodecyl radicals, such as the n-do
  • the tri alkyl si ly 1 terminated dialkylpolysiloxanes are trimethylsilyl terminated PDMS (polydimethylsiloxanes or dimethicones).
  • the silicone mixture comprises one or more amino silicones, that are preferably of formula (X):
  • X is R or a hydroxyl (OH) or a C1-C6- alkoxy group; preferably X is R, i.e. a monovalent hydrocarbon radical having from 1 to 18 carbon atoms, preferably from 1 to 6 carbon atoms, even better from 1 to 3 carbon atoms, more preferably methyl;
  • R 1 is a Ci- C 6 -alkylene radical, preferably a radical of the formula -CH2CH2CH2- or -CH2CH(CH3)CH2-
  • R 2 same or different, is a hydrogen atom or a Ci-C4-alkyl radical, preferably a hydrogen atom
  • R 3 is a Ci-C6-alkylene radical, preferably a radical of the formula -CH2CH2-, and x is 0 or 1 ;
  • - m+n is an integer from 50 to about 1000, preferably from 50 to 600.
  • A is an amino radical of the formula -R ⁇ fNR 2 - R 3 -] X NR 2 2, or the protonated amino forms of said amino radical, wherein R 1 is -CH2CH2CH2- or -CH2CH(CH3)CH2-, R 2 are hydrogen atoms, R 3 is -CH2CH2-, and x is 1.
  • R are alkyl radicals, preferably Ci-Cis alkyl radicals, such as the methyl, ethyl, n-propyl, isopropyl, 1-n-butyl, 2-n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl and tert-pentyl radicals, hexyl radicals, such as the n-hexyl radical, heptyl radicals such as the n-heptyl radical, octyl radicals such as the n-octyl radical and isooctyl radicals, such as the 2,2,4- trimethylpentyl radical, nonyl radicals, such as the n-nonyl radicals, decyl radicals, such as the n-decyl radical, dodecyl radicals, such as the n-dode
  • the amino silicones according to the invention have a viscosity of from 1 ,000 to 15,000 mPa.s at 25°C, preferably of from 1,500 to 15,000 mPa. s.
  • the amino silicones according to the invention have an amine value of from 2 to 10 mg of KOH per gram of amino silicone, preferably of from 3.5 to 8 mg.
  • the mole percent of amine functionality is preferably in the range of from about 0.3 to about 8%.
  • Examples of amino silicones useful in the silicone mixture according to the invention include tri alkyl sily 1 terminated amino silicone.
  • amino silicones are trimethylsilyl terminated aminoethylaminopropylmethylsiloxane, most preferably trimethylsilyl terminated aminoethylaminopropylmethylsiloxane - dimethylsiloxane copolymers.
  • the amino radical A can be protonated partially or fully by adding acids to the amino silicone, wherein the salt forms of the amino radical are obtained.
  • acids are carboxylic acids with 3 to 18 carbon atoms which can be linear or branched, such as formic acid, acetic acid, propionic acid, butyric acid, pivalic acid, sorbic acid, benzoic acid, salicylic acid.
  • the acids are preferably used in amounts of from 0.1 to 2.0 mol per 1 mol of amino radical A in the amino silicone of formula (X).
  • the silicone mixture preferably comprises (i) one or more tri alkyl sily 1 terminated dialkylpolysiloxanes having a viscosity of from 40,000 to less than 100,000 mPa.s at 25°C in a quantity of from 70 to 90% by weight, preferably from 75 to 85% by weight, relative to the total weight of the silicone mixture, and (ii) one or more amino silicones having a viscosity of from 1,000 to 15,000 mPa.s at 25°C and an amine value of from 2 to 10 mg of KOH per gram of amino silicone, in a quantity of from 10 to 30% by weight, preferably from 15 to 25% by weight, relative to the total weight of the silicone mixture.
  • the oil-in-water emulsion further comprises a mixture of emulsifiers that comprises one or more nonionic emulsifiers. It could optionally comprise one or more cationic surfactants.
  • the mixture of emulsifiers has a HLB value from 10 to 16.
  • the nonionic emulsifiers can be chosen among the nonionic surfactants as described hereunder.
  • RiO-(R 2 0)t-(G)v in which: - Ri represents a linear or branched alkyl or alkenyl radical comprising 6 to 24 carbon atoms and especially 8 to 18 carbon atoms, or an alkylphenyl radical whose linear or branched alkyl radical comprises 6 to 24 carbon atoms and especially 8 to 18 carbon atoms; - R2 represents an alkylene radical comprising 2 to 4 carbon atoms,
  • - G represents a sugar unit comprising 5 to 6 carbon atoms
  • - t denotes a value ranging from 0 to 10 and preferably 0 to 4,
  • - v denotes a value ranging from 1 to 15 and preferably 1 to 4.
  • alkylpolyglycoside surfactants are compounds of the formula described above in which:
  • Ri denotes a linear or branched, saturated or unsaturated alkyl radical comprising from 8 to 18 carbon atoms
  • R2 represents an alkylene radical comprising 2 to 4 carbon atoms
  • - t denotes a value ranging from 0 to 3 and preferably equal to 0,
  • G denotes glucose, fructose or galactose, preferably glucose
  • the degree of polymerization i.e. the value of v, possibly ranging from 1 to 15 and preferably from 1 to 4; the mean degree of polymerization more particularly being between 1 and 2.
  • the glucoside bonds between the sugar units are generally of 1- 6 or 1-4 type and preferably of 1-4 type.
  • the alkyl(poly)glycoside surfactant is an alkyl(poly)glucoside surfactant.
  • C8/Ci6 alkyl(poly)glycosides 1,4, and especially decyl glucosides and caprylyl/capryl glucosides, are most particularly preferred.
  • the nonionic emulsifiers can preferably be chosen among ethoxylated aliphatic alcohols, polyoxyethylene surfactants, carboxylic esters, polyethylene glycol esters, sorbitol ester and their ethoxylated derivatives, glycol esters of fatty acids, carboxylic amides, monoalkanolamine condensates, polyoxyethylene fatty acid amides.
  • nonionic emulsifiers are selected from:
  • polyoxyalkylene alkyl ethers especially (poly)ethoxylated fatty alcohols of formula:
  • R.3 representing a linear or branched C8-C40 alkyl or alkenyl group, preferably C8-C 30 alkyl or alkenyl group, optionally substituted with one or more hydroxyl groups, and
  • - c being an integer between 1 and 200 inclusive, preferentially between 2 and 150 and more particularly between 4 and 50, most preferably between 8 and 20.
  • the (poly)ethoxylated fatty alcohols are more particularly fatty alcohols comprising from 8 to 22 carbon atoms, oxyethylenated with 1 to 30 mol of ethylene oxide (1 to 30 OE);
  • polyoxyalkylene sorbitan (Cs-C 32 ) fatty acid esters especially polyethoxylated fatty acid esters of sorbitan preferably containing from 2 to 40 ethylene oxide units, most preferably from 2 to 20 ethylene oxide units; preferably polyoxyethylenated sorbitan (C10- C 24 ) fatty acid esters preferably containing from 2 to 40 ethylene oxide units, most preferably from 2 to 20 ethylene oxide units; and
  • the nonionic emulsifiers could be selected from alkyl ether of polyalkyleneglycol and alkyl esters of polyalkyleneglycol; preferably of polyethyleneglycol (PEG).
  • PEG polyethyleneglycol
  • Some useful emulsifiers are:
  • polyethyleneglycol octyl ether polyethyleneglycol lauryl ether; polyethyleneglycol tridecyl ether; polyethyleneglycol cetyl ether; polyethyleneglycol stearyl ether; among these, mention may be made more particularly of trideceth-3, trideceth-10 and steareth-6.
  • polyethyleneglycol nonylphenyl ether polyethyleneglycol dodecylphenyl ether; polyethyleneglycol cetylphenyl ether; polyethyleneglycol stearylphenyl ether;
  • polyethyleneglycol stearate and especially PEG-100 stearate.
  • the nonionic emulsifiers are chosen among steareth-6, PEG-100 stearate, trideceth-3 and trideceth-10 and their mixture; preferably, all these emulsifiers are present in the mixture of emulsifiers.
  • the mixture of emulsifiers could comprise one or more cationic emulsifiers that could be selected among tetraalkylammonium halides, tetraarylammonium halides, tetraalkylarylammonium halides, and their salts; quaternary ammonium compounds including salts; preferably, the cationic emulsifiers could be chosen among cetrimonium halides or behentrimonium halides, such as chloride.
  • the oil-in-water emulsion preferably comprises the mixture of emulsifiers in a total amount of from 5 to 15% by weight, preferably of from 8 to 15% by weight, most preferably of from 10 to 12% by weight, relative to the total weight of the emulsion.
  • the oil-in-water emulsion preferably comprises nonionic emulsifiers in a total amount of from 5 to 15% by weight, preferably of from 8 to 15% by weight, most preferably of from 10 to 12% by weight, relative to the total weight of the emulsion.
  • the oil-in-water emulsion preferably comprises cationic emulsifiers, when present, in a total amount of from 0.5 to 1.5% by weight, relative to the total weight of the emulsion.
  • the oil-in-water emulsion preferably comprises the silicone mixture in a total amount of from 40 to 60% by weight, preferably of from 45 to 55% by weight, relative to the total weight of the emulsion.
  • the oil-in-water emulsion preferably comprises the tri alkyl sily 1 terminated dialkylpolysiloxane(s) in a total amount of from 35 to 45% by weight, preferably of from 38-42% by weight, relative to the total weight of the emulsion.
  • the oil-in-water emulsion preferably comprises the amino silicone(s) in a total amount of from 5 to 15% by weight, preferably of from 8-12% by weight, relative to the total weight of the emulsion.
  • the oil-in-water emulsion comprises water preferably in an amount of from 25 to 50% by weight, preferably of from 30 to 45% by weight, most preferably of from 35 to 42% by weight, relative to the total weight of the emulsion.
  • the oil-in-water emulsion could additionally comprise a biocide, such as phenoxyethanol, that could be present in the emulsion in a quantity of from 0.5 to 1% by weight, relative to the total weight of the emulsion.
  • a method of preparation of the oil-in-water emulsion preferably comprises:
  • step - a step of adding, preferably step-wise, water, preferably demineralized water, to obtain an oil-in-water emulsion having D50 particle size of less than 350 nm.
  • the method of preparation of the oil-in-water emulsion could further comprise an additional step of adding a biocide.
  • Biocide could be added for preserving the emulsion against microbial contamination.
  • the biocide could be added at the level of for preserving emulsion against microbial contamination and obtaining the said emulsion.
  • the quantity of the biocide depends on the type of biocide and as recommended by the manufacturer.
  • the preparation of the mixture of emulsifiers could be made by mixing one or more nonionic emulsifiers.
  • the pH of the oil-in-water emulsion after neutralization is preferably of from 4 to 6.
  • the oil-in-water emulsion has D50 particle size of less than 350 nm, preferably of from 100 to 300 nm, more preferably from 150 to 250 nm, more preferably from 150 to 225 nm, and most preferably from 160 to 200 nm. It corresponds to the average hydrodynamic particle diameter.
  • the D50 particle size is expressed in volume.
  • the D50 particle size could be measured by using a device ZetaSizer from Malvern, UK, model Nano-ZS, which is based on the Photon Correlation Spectroscopy (PCS) method.
  • PCS Photon Correlation Spectroscopy
  • Emulsion particle size is measured by using a device ZetaSizer from Malvern, UK, model Nano-ZS which is based on the Photon Correlation Spectroscopy (PCS) method.
  • the D50 value of particle size (average hydrodynamic particle diameter) is measured, wherein the evaluating algorithm is “cumulants analysis”.
  • the viscosity is measured at 25°C, at atmospheric pressure.
  • Zero gap setting being made and with a shear rate of 1 s 1 for 2 minutes, at 25°C.
  • MCR Rheometer Series products work as per USP (US Pharmacopeia Convention) 912 - Rotational Rheometer methods.
  • the amine value is determined by acid-base titration using a potentiometer [Make: Veego; Model : VPT-MG] 0.6 g of sample is taken in a 500 ml beaker and a toluene-butanol 1 : 1 mixture is added and stirred to mix the sample thoroughly; then the sample solution is titrated with a 0.1(N) HC1 solution. A determination of the blank value with the toluene-butanol 1 : 1 mixture is also done. The calculation of the amine value is done by the above mentioned potentiometer.
  • the amine value is calculated according to the formula:
  • V Volume of HC1 required in ml
  • VBlank Volume of HC1 for blank value (without sample) with the toluene-butanol 1 : 1 mixture in ml
  • N Normality of HC1, i.e. 0.1 N
  • W weight of the sample taken in gram.
  • HLB Value The term HLB is well known to those skilled in the art, and denotes the hydrophilic-lipophilic balance of a surfactant or emulsifier. In the present invention, HLB values refer to the values at 25°C.
  • the HLB can be measured by experimental determination or can be calculated.
  • HLB (E + P)/5, with E being the weight percentage of oxyethylenecontent and P being the weight percentage of polyhydric alcohol content, described in to the publication Griffin, J. Soc. Cosm. Chem. 1954 (vol.5, n°4), pp.249-256.
  • the calculated HLB is the preferred HLB values that should be taken into account.
  • the hydrophilic part corresponds to the oxyethylene units condensed onto the fatty alcohol and the “calculated HLB” then corresponds to the “Griffin HLB” as defined hereabove.
  • the hydrophilic part is naturally defined as being beyond the carbonyl group, starting from the fatty chain(s).
  • the HLB value of individual surfactant/emulsifier can be calculated applying the Davies formula as described in Davies JT (1957), "A quantitative kinetic theory of emulsion type, I. Physical chemistry of the emulsifying agent", Gas/Liquid and Liquid/Liquid Interface (Proceedings of the International Congress of Surface Activity): 426-438.
  • HLB values for some cationic emulsifiers are given in Table IV, in “Cationic emulsifiers in cosmetics”, GODFREY, J. Soc. Cosmetic Chemists (1966) 17, pp l7-27.
  • the HLBM IX is said to be the required HLB for the mixture.
  • HLBA, HLBB the assigned HLB values for emulsifiers A and B;
  • HLBM IX the HLB of the mixture.
  • Said oil-in-water emulsion is for example described in WO
  • the cosmetic composition according to the invention may comprise the oil-in-water emulsion b in an amount ranging from 0.1% to 20% by weight, preferably from 0.3 % to 10% by weight and better still from 0.4% to 10% by weight, better from 0.5 to 8%, even more preferentially from 1 to 5% by weight relative to the total weight of the composition.
  • the composition according to the invention preferably comprises the tri alkyl sily 1 terminated dialkylpolysiloxane(s) having a viscosity of from 40,000 to less than 100,000 mPa.s at 25°C in a total amount ranging from 0.05 % to 8% by weight, more preferably from 0.1 % to 5% by weight, even more preferably from 0.2 % to 4% by weight, better from 0,3 to 3% by weight, relative to the total weight of the composition.
  • the composition according to the invention preferably comprises the amino silicone(s) having a viscosity of from 1,000 to 15,000 mPa.s at 25°C and an amine value of from 2 to 10 mg of KOH per gram of amino silicone, in a total amount ranging from 0.01% to 5% by weight, more preferably from 0.05 % to 3% by weight, even more preferably from 0.075 % to 2% by weight, better from 0.1 to 1% by weight, relative to the total weight of the composition.
  • the composition according to the invention comprises one or more chemical oxidizing agent and/or one or more oxidation dyes.
  • chemical oxidizing agent is intended to mean an oxidizing agent other than atmospheric oxygen.
  • the chemical oxidizing agent(s) is (are) selected from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulphates, in particular sodium persulphate, potassium persulphate and ammonium persulphate, peracids and oxidase enzymes (with possible co-factors) such as peroxidases, 2-electron oxidoreductases such as uricases and 4-electron oxygenases such as laccases, and mixtures thereof.
  • the chemical oxidizing agent(s) is (are) selected from hydrogen peroxide, persalts, and mixtures thereof, and better still is hydrogen peroxide.
  • said chemical oxidizing agent advantageously is present in an amount ranging from 0.1% to 20% by weight, preferably from 0.5% to 15% by weight, more preferably from 1% to 15% by weight, better still from 2% to 10% by weight, relative to the total weight of the cosmetic composition.
  • hydrogen peroxide advantageously is present in an amount ranging from 0.1 % to 20% by weight, preferably from 0,5% to 15% by weight, more preferably from 1% to 15% by weight, still better from 2% to 10% by weight relative to the total weight of the cosmetic composition.
  • Oxidation dyes may be chosen from one or more oxidation bases, optionally in combination with one or more couplers.
  • the oxidation dyes comprise at least one oxidation base and at least one coupler.
  • the oxidation bases are chosen from para- phenyl enedi amines, bis(phenyl)alkylenedi amines, para-aminophenols, ortho-aminophenols and heterocyclic bases, and addition salts thereof.
  • para-phenylenediamines examples that may be mentioned include para-phenylenediamine, para-tolylenediamine, 2- chi oro-para-phenyl enedi amine, 2, 3 -dimethyl -para-phenyl enedi amine,
  • para-phenylenediamine para-tolylenediamine, 2-isopropyl-para- phenylenediamine, 2 ⁇ -hydroxyethyl-para-phenylenediamine, 2-b- hydroxy ethyl oxy-para-phenyl enedi amine, 2, 6-di methyl -para- phenyl enedi amine, 2, 6-di ethyl -para-phenyl enedi amine, 2,3 -dimethyl- para-phenylenedi amine, N,N-bis(P-hydroxyethyl)-para- phenylenediamine, 2-chloro-para-phenylenediamine and 2-b- acetylaminoethyloxy-para-phenylenediamine, and the addition salts thereof with an acid, are particularly preferred.
  • bis(phenyl)alkylenediamines examples that may be mentioned include N,N'-bis(P-hydroxyethyl)-N,N'-bis(4'- aminophenyl)l,3-diaminopropanol, N,N'-bis(P-hydroxyethyl)-N,N'- bis(4'-aminophenyl)ethylenedi amine, N,N'-bis(4- aminophenyl)tetramethylenedi amine, N, N'-bis(P -hydroxy ethy 1)-N,N'- bis(4-aminophenyl)tetramethylenediamine, N,N'-bis(4- methylaminophenyl)tetramethylenedi amine, N,N'-bis(ethyl)-N,N'- bi s(4' -amino-3 '-methylphenyl)ethylenedi amine, 1 , 8-bis(2, 5- diaminoph
  • para-aminophenols examples that may be mentioned include para-aminophenol, 4-amino-3-methylphenol, 4-amino-3- fluorophenol, 4-amino-3-chlorophenol, 4-amino-3- hydroxymethylphenol, 4-amino-2-methylphenol, 4-amino-2- hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2- ami nomethyl phenol, 4 -ami no-2 -(b -hydroxy ethyl ami nomethyl)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 addition salts thereof.
  • heterocyclic bases examples that may be mentioned include pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.
  • pyridine oxidation bases that are useful in the present invention are the 3-aminopyrazolo[l,5-a]pyridine oxidation bases or addition salts thereof described, for example, in patent application FR 2 801 308.
  • Examples that may be mentioned include pyrazolo[l,5- a]pyrid-3-yl amine, 2-(acetylamino)pyrazolo[l,5-a]pyrid-3-yl amine, 2- (morpholin-4-yl)pyrazolo[l ,5-a]pyrid-3-ylamine, 3-aminopyrazolo[l,5- a]pyridine-2-carboxylic acid, 2-methoxypyrazolo[l,5-a]pyrid-3- ylamine, (3-aminopyrazolo[l,5-a]pyrid-7-yl)methanol, 2-(3- aminopyrazolo[l,5-a]pyrid-5-yl)ethanol, 2-(
  • pyrimidine derivatives mention may be made of the compounds described, for example, in patents DE 2359399, JP 88- 169571, JP 05-63124 and 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.
  • 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
  • pyrazole derivatives mention may be made of the compounds described in the patents DE 3843892, DE 4133957 and patent applications WO 94/08969, WO 94/08970, FR-A-2 733 749 and DE 195 43 988, such as 4,5-diamino-l-methylpyrazole, 4,5-diamino-l - (P-hydroxyethyl)pyrazole, 3,4-diaminopyrazole, 4,5-diamino-l-(4'- chlorobenzyl)pyrazole, 4,5-diamino-l,3-dimethylpyrazole, 4,5- di ami no- 3 -methyl - 1 -phenyl pyrazole, 4, 5 -di amino- 1 -methyl -3- phenylpyrazole, 4-amino-l,3-dimethyl-5-hydrazinopyrazole, 1-benzyl- 4,5-diamino-3-
  • a 4,5-diaminopyrazole will preferably be used, and even more preferentially 4,5-diamino-l-(P-hydroxyethyl)pyrazole and/or a salt thereof.
  • Pyrazole derivatives that may also be mentioned include diamino-N,N-dihydropyrazolopyrazolones and especially those described in patent application FR-A-2 886 136, such as the following compounds and the addition salts thereof: 2,3-diamino-6,7-dihydro- lH,5H-pyrazolo[ 1 ,2-a]pyrazol - 1 - one, 2 -ami no- 3 -ethyl ami no- 6, 7- dihydro-lH,5H-pyrazolo[l,2-a]pyrazol-l-one, 2-amino-3- isopropyl amino-6, 7-dihydro-lH,5H-pyrazolo[l,2-a]pyrazol-l -one, 2- ami no-3 -(pyrroli din- l-yl)-6, 7-dihydro- lH,5H-pyrazolo [ 1 ,2-a]pyrazol-
  • Use will preferably be made of 2,3-diamino-6,7-dihydro-lH,5H- pyrazolo[l,2-a]pyrazol-l-one and/or a salt thereof.
  • Heterocyclic bases that will preferentially be used include 4,5- diamino-1 -(b -hydroxy ethyl)pyrazole and/or 2,3-diamino-6,7-dihydro- lH,5H-pyrazolo[l,2-a]pyrazol-l-one and/or a salt thereof.
  • the oxidation bases are chosen from para- phenylenediamine, l-methyl-2,5-diaminobenzene, para-aminophenol, 1- hydroxy ethyl-4, 5-diaminopyrazole sulfate and 2,3- diaminodihydroxypyrazolone dimethosulfonate, the addition salts thereof and mixtures thereof.
  • said oxidation base advantageously is present in an amount ranging from 0.001% to 10% by weight, preferably from 0.005% to 10% by weight, relative to the total weight of the cosmetic composition.
  • the coupler(s) are advantageously chosen from those conventionally used for the dyeing of keratin fibres.
  • couplers mention may be made especially of meta- phenylenediamines, meta-aminophenols, meta-diphenols, naphthalene- based couplers and heterocyclic couplers, and also the addition salts thereof.
  • Examples that may be mentioned include 2-methyl-5- aminophenol, 5-N-(P-hydroxyethyl)amino-2-methylphenol, 3- ami nophenol, 1 ,3 -di hydroxy benzene, 1 ,3 -di hydroxy -2 -m ethylbenzene, 4-chloro-l ,3-dihydroxybenzene, 2, 4 -di ami no- 1 -(b- hydroxy ethyloxy)benzene, 2-amino-4- ⁇ -hydroxyethylamino)- 1 - methoxybenzene, 1,3-diaminobenzene, l,3-bis(2,4- diaminophenoxy)propane, 3-ureidoaniline, 3-ureido-l- dimethylaminobenzene, sesamol, l ⁇ -hydroxyethylamino-3,4- methylenedioxybenzene, a-naphthol, 2-methyl- 1 -n
  • addition salts of the oxidation bases and couplers that may be used in the context of the invention are especially chosen from the addition salts with an acid, such as hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates.
  • an acid such as hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates.
  • the coupler(s) are chosen from resorcinol, 2- methylresorcinol, 5-N-(P-hydroxyethyl)amino-2-methylphenol, 2- methyl-5-aminophenol, 1 -b -hydroxy ethyl oxy -2, 4 -di ami nobenzene dihydrochloride and 3-aminophenol, the addition salts thereof, and mixtures thereof.
  • said coupler advantageously is present in an amount ranging from 0.001% to 10% by weight, preferably from 0.005% to 10% by weight, relative to the total weight of the cosmetic composition.
  • said oxidizing dye advantageously is present in an amount ranging from 0.001% to 20% by weight, preferably from 0.01% to 5% by weight, relative to the total weight of the cosmetic composition.
  • the cosmetic composition may optionally also comprise one or more alkaline agents.
  • the alkaline agents may be chosen from carbonates, alkanolamines such as monoethanolamine, diethanolamine, triethanolamine and derivatives thereof, oxyethylenated and/or oxypropylenated ethylenediamines, mineral or organic hydroxides, alkali metal silicates such as sodium metasilicates, amino acids, preferably basic amino acids such as arginine, lysine, ornithine, citrulline and histidine, and the compounds of formula (I) below: in which:
  • - W is a divalent (Ci-C8)alkylene group, preferably a propylene group, optionally substituted especially with a hydroxyl group or a Ci- C4 alkyl radical;
  • Ra, Rb, Rc and Rd which may be identical or different, represent a hydrogen atom or a C1-C4 alkyl or C1-C4 hydroxyalkyl radical.
  • the mineral or organic hydroxides are preferably chosen from i) hydroxides of an alkali metal, ii) hydroxides of an alkaline-earth metal, for instance sodium hydroxide or potassium hydroxide, iii) hydroxides of a transition metal, such as hydroxides of metals from groups III, IV, V and VI, iv) hydroxides of lanthanides or actinides, quaternary ammonium hydroxides and guanidinium hydroxide.
  • the hydroxide may be formed in situ, for instance guanidine hydroxide, formed by reacting calcium hydroxide with guanidine carbonate.
  • the alkaline agents are chosen from alkanolamines, in particular monoethanolamine, diethanolamine and triethanolamine, and ammonium hydroxide, and their mixtures.
  • Said cosmetic composition may optionally also comprise one or more organic solvents.
  • Organic solvents that may be mentioned include linear or branched and preferably saturated monoalcohols or diols, comprising 2 to 6 carbon atoms, such as ethyl alcohol, isopropyl alcohol, hexylene glycol (2-methyl-2,4-pentanediol), neopentyl glycol and 3-methyl-l,5- pentanediol, butylene glycol, dipropylene glycol and propylene glycol; aromatic alcohols such as benzyl alcohol or phenylethyl alcohol; polyols containing more than two hydroxyl functions, such as glycerol; polyol ethers, for instance ethylene glycol or propylene glycol monomethyl, monoethyl or monobutyl ethers; and also diethylene glycol alkyl ethers, especially C1-C4 alkyl ethers, for instance diethylene glycol monoethy
  • composition according to the invention may further comprise one or more cationic polymers different from the polymers comprising one or more cationic or quaternized acrylamide and/or methacrylamide unit(s) described above.
  • These optional additional cationic polymers do not contain any cationic/quaternized acrylamide and/or methacrylamide unit.
  • these optional additional cationic polymers are non silicone polymers.
  • the additional cationic polymers that may be used preferably have a weight-average molar mass (Mw) of between 500 and 5 c 10 6 approximately and preferably between 10 3 and 3 c 10 6 approximately.
  • Mw weight-average molar mass
  • Cationic polysaccharides especially cationic celluloses and galactomannan gums.
  • cationic polysaccharides mention may be made more particularly of cellulose ether derivatives comprising quaternary ammonium groups, cationic cellulose copolymers or cellulose derivatives grafted with a water-soluble quaternary ammonium monomer and cationic galactomannan gums.
  • the cellulose ether derivatives comprising quaternary ammonium groups are especially described in French patent 1 492 597, and mention may be made of the polymers sold under the name UCARE POLYMER “JR” (JR 400 LT, JR 125 and JR 30M) or “LR” (LR 400 or LR 30M) by the company Amerchol. These polymers are also defined in the CTFA dictionary as quaternary ammoniums of hydroxy ethylcellulose that have reacted with an epoxide substituted with a trimethylammonium group.
  • Cationic cellulose copolymers or cellulose derivatives grafted with a water-soluble quaternary ammonium monomer are described especially in EiS patent 4 131 576, and mention may be made of hydroxyalkylcelluloses, for instance hydroxymethyl-, hydroxy ethyl- or hydroxypropylcelluloses grafted, in particular, with a [(meth)acrylic units] dimethyldiallylammonium salt.
  • the commercial products corresponding to this definition are more particularly the products sold under the names CELQUAT L 200 and CELQUAT H 100 by the company National Starch.
  • the cationic galactomannan gums are described more particularly in E!S patents 3 589 578 and 4 031 307, and mention may be made of guar gums comprising cationic trialkylammonium groups. Else is made, for example, of guar gums modified with a 2,3- epoxypropyltrimethylammonium salt (for example, chloride). Such products are especially sold under the names JAGE1AR C13 S, JAGE1AR C 15, JAGE1AR C 17 or JAGE1AR C 162 by the company Rhodia.
  • Water-soluble polyamino amides prepared in particular by polycondensation of an acidic compound with a polyamine; these polyamino amides can be crosslinked with an epihalohydrin, a diepoxide, a dianhydride, an unsaturated dianhydride, a bis-unsaturated derivative, a bis-halohydrin, a bis-azetidinium, a bis-haloacyldiamine, a bis-alkyl halide or alternatively with an oligomer resulting from the reaction of a difunctional compound which is reactive with a bis- halohydrin, a bis-azetidinium, a bis-haloacyldiamine, a bis-alkyl halide, an epihalohydrin, a diepoxide or a bis-unsaturated derivative; the crosslinking agent being used in proportions ranging from 0.025 to 0.35 mol per amine group of the polyamino amide; these polya
  • Polyamino amide derivatives resulting from the condensation of polyalkylene polyamines with polycarboxylic acids followed by alkylation with bifunctional agents Mention may be made, for example, of adipic acid/dialkylaminohydroxyalkyldialkylenetriamine polymers in which the alkyl radical comprises from 1 to 4 carbon atoms and preferably denotes methyl, ethyl or propyl.
  • alkyl radical comprises from 1 to 4 carbon atoms and preferably denotes methyl, ethyl or propyl.
  • Polymers of this type are sold in particular under the name HERCOSETT 57 by the company Hercules Inc. or alternatively under the name PD 170 or DELSETTE 101 by the company Hercules in the case of the adipic aci d/epoxy propyl/di ethyl enetri amine copolymer.
  • R 12 denotes a hydrogen atom or a methyl radical
  • Rio and Rn independently of each other, denote a C1-C6 alkyl group, a hydroxyl(Ci-C5)alkyl group, a C1-C4 amidoalkyl group; or alternatively Rio and R1 1 may denote, together with the nitrogen atom to which they are attached, an heterocyclic group such as piperidinyl or morpholinyl; Rio and R11, independently of each other, preferably denote a C1-C4 alkyl group; and
  • - Y is an anion such as bromide, chloride, acetate, borate, citrate, tartrate, bisulfate, bisulfite, sulfate or phosphate.
  • R 13 , Ri4, RI 5 and Ri6 which may be identical or different, represent aliphatic, alicyclic or arylaliphatic radicals comprising from 1 to 20 carbon atoms, or C1-C12 hydroxyalkylaliphatic radicals, or else R13, R14, R15 and Ri6, together or separately, constitute, with the nitrogen atoms to which they are attached, heterocycles optionally comprising a second non-nitrogen heteroatom, or else R13, R14, R15 and Ri6 represent a linear or branched Ci- Ce alkyl radical substituted with a nitrile, ester, acyl, amide or -CO-O- R17-D or -CO-NH-R17-D group in which R17 is an alkylene and D is a quaternary ammonium group;
  • A1 and B 1 represent divalent polymethylene groups comprising from 2 to 20 carbon atoms, linear or branched, saturated or unsaturated, and which may contain, linked to or intercalated in the main chain, one or more aromatic rings or one or more oxygen or sulfur atoms or sulfoxide, sulfone, disulfide, amino, alkylamino, hydroxyl, quaternary ammonium, ureido, amide or ester groups, and
  • - X denotes an anion derived from a mineral or organic acid; it being understood that Al, R1 3 and R15 can form, with the two nitrogen atoms to which they are attached, a piperazine ring; in addition, if Al denotes a linear or branched, saturated or unsaturated alkylene or hydroxyalkylene radical, B 1 may also denote a group (CH2)n-CO-D-OC-(CH 2 )p- wherein n and p, which may be identical or different, denote an integer from 2 to 20, and wherein D denotes: a) a glycol residue of formula -O-Z-O-, in which Z denotes a linear or branched hydrocarbon-based radical, or a group corresponding to one of the following formulae: -(CH2-CH2-0)x-CH2-CH2- and -[CH2- CH(CH3)-0] y -CH2-CH(CH3)-, where x and y denote an integer from 1 to 4, representing
  • X is an anion such as chloride or bromide.
  • Mn number-average molar mass
  • Ri, R2, R3 and R4 which may be identical or different, denote an alkyl or hydroxyalkyl radical containing from 1 to 4 carbon atoms, n and p are integers ranging from 2 to 20, and X is an anion derived from an organic or mineral acid.
  • R 18 , Ri 9 , R20 and R21 which may be identical or different, represent a hydrogen atom or a methyl, ethyl, propyl, b-hydroxyethyl, b- hydroxypropyl or
  • p is equal to 0 or to an integer between 1 and 6, with the proviso that Ris, Ri9, R20 and R21 do not simultaneously represent a hydrogen atom,
  • - r and s which may be identical or different, are integers between 1 and 6, - q is equal to 0 or to an integer between 1 and 34,
  • X- denotes an anion such as a halide
  • - A denotes a dihalide radical or preferably represents -CH2-CH2-O-CH2- CH2-.
  • Examples that may be mentioned include the products Mirapol ® A15, Mirapol ® ADI, Mirapol ® AZ 1 and Mirapol ® 175 sold by the company Miranol.
  • these polymers may be chosen especially from homopolymers or copolymers comprising one or more units derived from vinylamine and optionally one or more units derived from vinylformamide.
  • these cationic polymers are chosen from polymers comprising, in their structure, from 5 mol% to 100 mol% of units corresponding to formula (A) and from 0 to 95 mol% of units corresponding to formula (B), preferentially from 10 mol% to 100 mol% of units corresponding to formula (A) and from 0 to 90 mol% of units corresponding to formula (B).
  • These polymers may be obtained, for example, by partial hydrolysis of poly vinylformamide. This hydrolysis may be performed in an acidic or basic medium.
  • the weight-average molecular mass of the said polymer measured by light scattering, may range from 1,000 to 3 000 000 g/mol, preferably from 10,000 to 1,000,000 g/mol and more particularly from 100,000 to 500,000 g/mol.
  • the polymers comprising units of formula (A) and optionally units of formula (B) are sold especially under the name Lupamin by the company BASF, for instance, and in a non-limiting manner, the products sold under the names Lupamin 9095, Lupamin 5095, Lupamin 1095, Lupamin 9030 (or Luviquat 9030) and Lupamin 9010.
  • cationic polymers that may be used in the context of the invention are cationic proteins or cationic protein hydrolysates, polyalkyleneimines, in particular polyethyleneimines, polymers comprising vinylpyridine or vinylpyridinium units, condensates of polyamines and of epichlorohydrin, quaternary polyureylenes and chitin derivatives.
  • the additional cationic polymers are preferably chosen from cyclopolymers of alkyldiallylamine or of dialkyldiallylammonium corresponding to the general family (6).
  • the additional cationic polymers are chosen from homo or copolymers of dimethyldiallylammonium halides, preferably homo or copolymers of dimethyldiallylammonium chloride, still better homopolymer of dimethyldiallylammonium chloride, such as homopolymer of dimethyldiallylammonium chloride with corresponding INCI name Polyquaternium-6.
  • the composition can comprise:
  • polymer(s) comprising one or more cationic or quaternized (meth)acrylamide units, preferably chosen from (meth)acrylamido(Ci-C 6 alkyl)tri(Ci-C4 alkyl) ammonium halide
  • one or more additional cationic polymers different from the polymers comprising one or more cationic or quaternized (meth)acrylamide units described above, preferably chosen from cyclopolymers of alkyldiallylamine or of dialkyldiallylammonium corresponding to the general family (6); more preferentially chosen from homo or copolymers of dimethyldiallylammonium halides, preferably homo or copolymers of dimethyldiallylammonium chloride, still better homopolymer of dimethyldiallylammonium chloride with corresponding INCI name Polyquaternium-6.
  • the amount of additional cationic polymer(s), different from the polymers comprising one or more cationic or quaternized (meth)acrylamide units, when they are present in the cosmetic composition of the present invention preferably ranges from 0.01 to 10% by weight, more preferentially from 0.02 to 5% by weight, and better still from 0.04 to 1% by weight, and even more preferably 0.05 to 0.5% by weight, relative to the total weight of the cosmetic composition.
  • the cosmetic composition of the invention may also contain various additives conventionally used in hair compositions.
  • additives that may be used in accordance with the invention, mention may be made of anionic or non-ionic polymers, additional amphoteric polymers different from the polymers comprising one or more cationic or quaternized (meth)acrylamide units previously described, antidandruff agents, anti-seborrhoea agents, agents for preventing hair loss and/or for promoting hair regrowth, fatty substances, vitamins and provitamins including panthenol, sunscreens, mineral or organic pigments, sequestrants, plasticizers, solubilizers, acidifying agents, mineral or organic thickeners, especially polymeric thickeners, opacifiers or nacreous agents, antioxidants, hydroxy acids, fragrances and preserving agents, and mixtures thereof.
  • the above additives are generally present in an amount for each of them of between 0.01% and 40% by weight, and preferably between 0.1% and 20% by weight relative to the weight of the cosmetic composition of the invention.
  • the present invention also relates to a cosmetic treatment process, especially for dyeing and/or lightening keratin fibres, and in particular human keratin fibres, wherein a composition as described above, is applied to said keratin fibres, and after an optional leave-on time, optionally removing it by rinsing.
  • the leave-on time of the composition on the keratin fibres may range from 1 minute to 60 minutes, better still from 5 minutes to 45 minutes and even better still from 10 minutes to 30 minutes.
  • composition may be applied to wet or dry keratin fibres.
  • composition as previously described is obtained from the mixture of at least two compositions:
  • the present invention may also relate to a process for dyeing keratin fibres, which consists in applying to the said keratin fibres a composition comprising: a. one or more polymers comprising one or more cationic or quaternized acrylamide and/or methacrylamide unit(s); b. an oil-in-water emulsion having D50 particle size of less than
  • a silicone mixture comprising (i) one or more tri alkyl sily 1 terminated dialkylpolysiloxane(s) having a viscosity of from 40,000 to less than 100,000 mPa.s at 25°C and (ii) one or more amino silicone(s) having a viscosity of from 1,000 to 15,000 mPa.s at 25°C and an amine value of from 2 to 10 mg of KOH per gram of amino silicone,
  • emulsifiers comprising one or more nonionic emulsifiers, wherein the mixture of emulsifiers has a HLB value of from 10 to 16, and - water; c. one or more chemical oxidizing agent and one or more oxidation dyes; d. optionally one or more cationic polymers different from the polymers comprising one or more cationic or quaternized acrylamide and/or methacrylamide unit(s).
  • the invention may also relate to a process for lightening keratin fibres, which consists in applying to the said keratin fibres a composition comprising: a. one or more polymers comprising one or more cationic or quaternized acrylamide and/or methacrylamide unit(s); b.
  • the present invention also relates to the use of the composition according to the invention as described above for the cosmetic treatment of keratin fibres, in particular dyeing and/or lightening keratin fibres, and in particular human keratin fibres.
  • the invention relates to a kit comprising at least two compartments: - a first compartment comprising a first composition comprising one or more oxidation dye(s) as defined above;
  • a second compartment comprising a second composition comprising one or more chemical oxidizing agent(s) as defined above; one or more polymers comprising one or more cationic or quaternized acrylamide and/or methacrylamide unit(s) as defined above, being comprised in the first and/or second composition; at least one oil-in-water emulsion as defined above being comprised in the first and/or second composition, said polymers comprising one or more cationic or quaternized acrylamide and/or methacrylamide unit(s) and said oil-in-water emulsion being preferably in the second composition.
  • keratin fibres denotes human keratin fibres, and in particular human hair such as hair.
  • Example 1 Preparation of an oil-in-water emulsion
  • amino silicone fluid trimethylsilyl-terminated aminoethyl-aminopropylmethylsiloxane - dimethylsiloxane copolymer with amine value of 7.2 mg of KOH/g sample, and a viscosity of 5,600 mPa.s at 25°C
  • 1,800 g of trimethylsilyl terminated dimethylsiloxane polymer fluid of viscosity 61,500 mPa.s at 25°C were introduced under stirring in the same tank. Both fluids were mixed for 2 hours at room temperature.
  • a stable oil-in-water emulsion having D50 particle size of 170 nm was obtained.
  • composition A was prepared from the ingredients indicated in table 1 below (wt. % of AM).
  • composition A is mixed with oxidizing compositions 1 , 2 and 3, respectively, with a mixing ratio 1 : 1.
  • Hair locks show a very good color delivery and very good conditioning.
  • the evaluation has been performed with the WDXRF Optim’ s Thermofisher (Wavelenght Dispersion) XRF system.
  • the principle is based on radiation emission characteristic of the chemical element, produced by the impact of high energy photons dispensed by an X-ray tube.
  • the operational parameters are the following: - Gas Flow Helium - Argon/Methane (90/10)

Abstract

La présente invention concerne une composition cosmétique comprenant : a. un ou plusieurs polymères comprenant une ou plusieurs unités d'acrylamide et/ou de méthacrylamide cationique ou quaternisée; b. une émulsion huile dans eau présentant une taille de particule D50 inférieure à 350 nm et comprenant : - un mélange de silicone comprenant (i) un ou plusieurs dialkylpolysiloxanes à terminaison trialkylsilyle présentant une viscosité de 40 000 à moins de 100 000 mPa.s à 25 °C et (ii) une ou plusieurs silicones aminées présentant une viscosité de 1 000 à 15 000 mPa.s à 25 °C et un indice d'amine de 2 à 10 mg de KOH par gramme de silicone aminée, - un mélange d'émulsifiants comprenant un ou plusieurs émulsifiants non ioniques, le mélange d'émulsifiants présentant une valeur HLB de 10 à 16, et - de l'eau; c. un ou plusieurs oxydants chimiques et/ou un ou plusieurs colorants d'oxydation; d. éventuellement un ou plusieurs polymères cationiques différents des polymères comprenant une ou plusieurs unités d'acrylamide et/ou de méthacrylamide cationique ou quaternisée.
PCT/EP2021/067091 2020-06-26 2021-06-23 Composition comprenant un polymère comprenant au moins une unité de (méth)acrylamide cationique, une silicone particulière et un oxydant chimique et/ou un colorant d'oxydation WO2021259974A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3131695A1 (fr) * 2022-01-12 2023-07-14 L'oreal Composition comprenant au moins un tensioactif anionique, une silicone particulière et un agent oxydant chimique

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Publication number Priority date Publication date Assignee Title
FR3131695A1 (fr) * 2022-01-12 2023-07-14 L'oreal Composition comprenant au moins un tensioactif anionique, une silicone particulière et un agent oxydant chimique

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