WO2020260486A1 - Procédé de coloration de fibres kératiniques à l'aide d'un polycarbonate cyclique particulier, composé comprenant au moins un groupe amine et un colorant, composition et dispositif - Google Patents

Procédé de coloration de fibres kératiniques à l'aide d'un polycarbonate cyclique particulier, composé comprenant au moins un groupe amine et un colorant, composition et dispositif Download PDF

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WO2020260486A1
WO2020260486A1 PCT/EP2020/067883 EP2020067883W WO2020260486A1 WO 2020260486 A1 WO2020260486 A1 WO 2020260486A1 EP 2020067883 W EP2020067883 W EP 2020067883W WO 2020260486 A1 WO2020260486 A1 WO 2020260486A1
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group
formula
radical
alkyl
composition
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PCT/EP2020/067883
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English (en)
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Andrew Greaves
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L'oreal
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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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4993—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • A61K8/73—Polysaccharides
    • A61K8/736—Chitin; Chitosan; Derivatives thereof
    • 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
    • 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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes

Definitions

  • the present invention relates to a process for dyeing keratin fibers, comprising the application to the keratin fibers of a) at least one particular carbonate ester, b) at least one compound comprising at least one amine group and c) at least one coloring agent chosen from pigments, direct dyes, and mixtures thereof.
  • the first type of dyeing is“permanent” or oxidation dyeing, which uses dye compositions containing oxidation dye precursors, generally known as oxidation bases.
  • oxidation bases are colorless or weakly colored compounds which, when combined with oxidizing products, can give rise to colored compounds via a process of oxidative condensation.
  • the shades obtained with these oxidation bases can be varied by combining them with couplers or color modifiers.
  • couplers or color modifiers The variety of molecules used as oxidation bases and couplers allows a wide range of colors to be obtained.
  • the second type of dyeing is "semi-permanent” dyeing or direct dyeing, which consists in applying, to the keratin fibers, direct dyes, which are colored and coloring molecules that have affinity for said fibers, in leaving them on for a time, and then in rinsing them off.
  • This type of process does not require the use of an oxidizing agent to develop the coloring. However, it is possible to use such an agent in order to obtain, along with the coloring, a lightening effect. This is then referred to as direct dyeing or semi-permanent dyeing under lightening conditions.
  • Permanent or semi-permanent dyeing processes under lightening conditions therefore need to use, with the dye composition, an aqueous composition comprising at least one oxidizing agent, under alkaline pH conditions in the vast majority of cases.
  • the colorings thus obtained are only short-lasting. Specifically, the colorings have a tendency to fade out, or even to disappear, rapidly, with respect to external agents, such as light, sweat, mechanical actions (brushing, styling) and notably after a few shampoo washes.
  • the dyeing power of these compositions may not be entirely satisfactory, or even may be poor, and lead to a restricted range of colors.
  • the colorings may also be too selective, i.e. the difference in coloring is too great along the same keratin fiber that is differently sensitized between its end and its root.
  • a subject of the present invention is a process for dyeing keratin fibers, comprising:
  • R 1 , R 2 , R 3 and R 4 which may be identical or different, represent a hydrogen atom or a (CrC 6 )alkyl and particularly (CrC4)alkyl group, it being understood that one of the groups R 1 , R 2 , R 3 or R 4 denotes a chain -(ALK) m -(Q) q -(Z) z -(Y)y-(ALK')p-(W) w -;
  • R 1 , R 2 and R 3 denote a hydrogen atom, and R 4 denotes the chain:
  • ALK and ALK' which may be identical or different, represent a (CrCi2)alkylene group optionally substituted and/or interrupted with one or more heteroatoms such as oxygen, sulfur, or NR 8 with R 8 as defined below; in particular, ALK and ALK' represent (CrC 6 )alkylene, preferably (CrC4)alkylene, such as methylene;
  • Q, Y and W which may be identical or different, represent an oxygen or sulfur atom or NR 8 , with R 8 representing a hydrogen atom or a (CrC4)alkyl or benzyl group, preferably oxygen or NR 8 such as NH;
  • (Ci-Cioo)alkylene optionally interrupted with one or more oxygen or sulfur atoms and/or with one or more radicals NR with R representing a hydrogen atom or a C1-C4 alkyl radical such as NH and/or with one or more radicals— Si(R' 1 )(R' 2 )- with R' 1 and R' 2 , which may be identical or different, representing a hydrogen atom, hydroxyl, (Ci- C4)alkyl or (CrC4)alkoxy, preferably a C1-C4 alkyl such as methyl; preferably, said alkylene radical denotes a (Ci-Cioo)alkylene radical optionally interrupted with one or more oxygen atoms and/or with one or more -SiMe2 radicals,
  • (C2-Cioo)alkenylene optionally interrupted with one or more oxygen or sulfur atoms and/or with one or more radicals NR with R representing a hydrogen atom or a C1-C4 alkyl radical such as NH and/or with one or more radicals— Si(R' 1 )(R' 2 )- with R' 1 and R' 2 , which may be identical or different, representing a hydrogen atom, hydroxyl, (Ci- C4)alkyl or (CrC4)alkoxy, preferably a C1-C4 alkyl such as methyl; preferably, said alkenylene radical denotes a (C2-Cioo)alkenylene radical optionally interrupted with one or more oxygen atoms and/or with one or more -SiMe2 radicals,
  • hetero)arylene such as phenylene, for instance 1 ,3-phenylene,
  • u represents an integer ranging from 2 to 4, preferably 2 or 3,
  • - T is divalent when u is 2, is trivalent when u is 3, and tetravalent when u is 4;
  • composition (Ci) comprising:
  • At least one coloring agent chosen from pigments, direct dyes and mixtures thereof.
  • a subject of the present invention is a multi-compartment device comprising:
  • composition (C ⁇ ) comprising a) at least one compound of formula (I) as defined above, and
  • composition (C3) different from composition (C2), composition (C3) comprising b) at least one compound comprising at least one amine group, it being understood that:
  • composition (C ⁇ ) and/or composition (C 3 ) comprise c) at least one coloring agent chosen from pigments, direct dyes and mixtures thereof.
  • keratin fibers means fibers of human or animal origin such as head hair, bodily hair, the eyelashes, the eyebrows, wool, angora, cashmere or fur. According to the present invention, the keratin fibers are preferably human keratin fibers, more preferentially the hair.
  • the term“compound comprising at least one amine group” means a compound comprising at least one primary -NH2, secondary >NH or tertiary -N ⁇ amino group and not comprising any carbonate functions -O-CO-O-; preferably, said compound comprises at least one primary or secondary amine group; more preferentially, said compound comprises at least one primary amine group;
  • alkyl means a linear or branched hydrocarbon-based radical containing from 1 to 8 carbon atoms, in particular from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, for example methyl, ethyl, n-propyl, isopropyl, butyl, n- pentyl or n-hexyl, preferably methyl;
  • alkenyl means a linear or branched hydrocarbon-based radical containing from 2 to 8 carbon atoms, in particular from 2 to 6 carbon atoms, preferably from 2 to 4 carbon atoms, and comprising at least one or more conjugated or non-conjugated ethylenic unsaturations, such as ethylenyl, n-propylenyl, isopropylenyl, butylenyl, n- pentylenyl or n-hexylenyl;
  • alkox y means an alkyl-oxy group with“alkyk as defined previously;
  • alkylene means a linear or branched divalent hydrocarbon-based radical containing from 1 to 8 carbon atoms, in particular from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, such as methylene, ethylene, n-propylene, n-butylene, n- pentylene or n- hexylene;
  • alkenylene means a hydrocarbon-based radical as defined for“alkenyf’
  • the term“(hetero)arylene” means a divalent "aryl” or divalent "heteroaryl” group, said aryl or heteroaryl groups being as defined below
  • the term“(hetero)cycloalkylene” means a divalent "cycloalkyl” or divalent
  • heterocycloalkyl group, said cycloalkyl or heterocycloalkyl groups being as defined below;
  • alkyl, alkenyl, alkylene, alkenylene or alkoxy groups means that said groups may be substituted on the hydrocarbon-based radical with one or more groups, which may be identical or different, chosen from i) hydroxyl, ii) thiol, iii) halogen, iv) (CrC4)alkoxy, v) hydroxy(C2-C4)alkoxy; vi)
  • an "aryl ⁇ ' radical represents a monocyclic or fused or nonfused polycyclic carbon- based group comprising from 6 to 22 carbon atoms, and in which at least one ring is aromatic; preferentially, the aryl radical is a phenyl, biphenyl, naphthyl, indenyl, anthracenyl or tetrahydronaphthyl; more preferentially, the aryl radical is a phenyl; a“heteroaryl radical' represents a 5- to 22-membered monocyclic or fused or nonfused polycyclic group, comprising from 1 to 6 heteroatoms chosen from nitrogen, oxygen, sulfur and selenium, and at least one ring of which is aromatic; preferentially, a heteroaryl radical is chosen from acridinyl, benzimidazolyl, benzobistriazolyl, benzopyrazolyl, benzopyridazinyl, benzoquinolyl, benzothiazolyl,
  • heterocyclic radical' is a 5- to 22-membered, monocyclic or fused or nonfused polycyclic radical which may contain one or two unsaturations but is not aromatic, including from 1 to 6 heteroatoms chosen from nitrogen, oxygen and sulfur;
  • a“heterocycloalkyl radical ⁇ ’ is a heterocyclic radical comprising at least one saturated ring and at least one heteroatom chosen from nitrogen, oxygen and sulfur;
  • aryl ⁇ ' or heteroaryl ⁇ ' radicals or the aryl or heteroaryl part of a radical may be substituted with at least one substituent borne by a carbon atom, chosen from:
  • alkyl radicals possibly forming with the nitrogen atom to which they are attached a saturated or unsaturated, optionally substituted 5- to 7-membered heterocycle, optionally comprising at least one other nitrogen or non-nitrogen heteroatom,
  • a 5- or 6-membered heteroaryl radical optionally substituted with a (CrC4)alkyl radical, preferentially methyl;
  • acylamino radical (-NR-C(O)-R') in which the radical R is a hydrogen atom or a Ci- C4 alkyl radical optionally bearing at least one hydroxyl group and the radical R' is a Ci- C2 alkyl radical;
  • an alkylsulfonylamino radical (R’-S(0) 2 -N(R)-) in which the radical R represents a hydrogen atom or a C1-C4 alkyl radical optionally bearing at least one hydroxyl group and the radical R' represents a C1-C4 alkyl radical or a phenyl radical; an aminosulfonyl radical ((R) 2 N-S(0) 2 -) in which the radicals R, which may be identical or different, represent a hydrogen atom or a C1-C4 alkyl radical optionally bearing at least one hydroxyl group;
  • the“a/y/" or“heteroaryP' radicals or the aryl or heteroaryl part of a radical may be substituted with at least one substituent borne by a carbon atom, chosen from a Ci-C e alkyl radical, a halogen atom; a C 1 -C 2 alkoxy radical; a polyhaloalkyl group, preferentially trifluoromethyl, more preferentially from a C 1 -C 6 alkyl radical;
  • cyclic or heterocyclic part of a nonaromatic radical may be substituted with at least one substituent chosen from the following groups:
  • radical R is a hydrogen atom or a Ci- C 4 alkyl radical optionally bearing at least one hydroxyl group
  • the radical R is a Ci- C 2 alkyl radical or an amino radical optionally substituted with one or two C 1 -C 4 alkyl groups, which may be identical or different, themselves optionally bearing at least one hydroxyl group, said alkyl radicals possibly forming, with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted 5- to 7-membered heterocycle optionally comprising at least one other nitrogen or non-nitrogen heteroatom;
  • R-C(O)-O- in which the radical R is a C 1 -C 4 alkyl radical or an amino group optionally substituted with one or two identical or different C 1 -C 4 alkyl groups themselves optionally bearing at least one hydroxyl group, said alkyl radicals possibly forming with the nitrogen atom to which they are attached a saturated or unsaturated, optionally substituted 5- to 7-membered heterocycle, optionally comprising at least one other nitrogen or non-nitrogen heteroatom;
  • R-G-C(O)- in which the radical R is a C 1 -C 4 alkyl radical, G is an oxygen atom or an amino group optionally substituted with a C 1 -C 4 alkyl group itself optionally bearing at least one hydroxyl group, said alkyl radical possibly forming, with the nitrogen atom to which it is attached, a saturated or unsaturated, optionally substituted 5- to 7-membered heterocycle, optionally comprising at least one other nitrogen or non-nitrogen heteroatom;
  • the cyclic or heterocyclic part of a nonaromatic radical may be substituted with at least one substituent chosen from C 1 -C 4 alkoxy, (poly)hydroxy(C 2 -C 4 )alkoxy or C 1 -C 4 alkyl groups; more preferentially with at least one C 1 -C 4 alkyl radical such as methyl;
  • a cyclic or heterocyclic radical, or a nonaromatic part of an aryl or heteroaryl radical may also be substituted with one or more oxo groups;
  • a subject of the present invention is a process for dyeing keratin fibers as defined above.
  • the process of the invention in particular makes it possible to obtain colorings which have good properties, in particular in terms of intensity, homogeneity, fastness toward external agents and persistence with respect to shampoo washing, while at the same time respecting the integrity of the keratin fibers and reducing the risk of leaching with water leading to staining of fabrics in contact with the dyed fibers.
  • Steps (i), (ii) and (iii) may be performed in this order or in any order.
  • Steps (i), (ii) and (iii) may be performed sequentially in this order, i.e. (i) then (ii) and then (iii) or in any order.
  • steps (ii) and (iii) may be performed simultaneously, followed by step (i).
  • steps (i) and (iii) may be performed simultaneously, followed by step (ii).
  • steps (i), (ii) and (iii) are performed simultaneously.
  • All of the steps (i), (ii) and (iii) may be repeated several times, for example twice.
  • the compound(s) (I), the compound(s) comprising at least one amine group and the coloring agent(s) applied, respectively, during steps (i), (ii) and (iii) may be identical or different.
  • the process according to the present invention comprises (i) a step consisting in applying to the keratin fibers at least a) one compound of formula (I) as defined above.
  • u is equal to 2 or 3 and T represents a divalent or trivalent group chosen from ii) (Ci-Ce)alkylene, iv) (hetero)arylene and v) cycloalkylene.
  • u is equal to 2 and T represents a (Ci-Cioo)alkylene radical optionally interrupted with one or more oxygen or sulfur atoms and/or with one or more radicals NR with R representing a hydrogen atom or a C1-C4 alkyl radical such as NH and/or with one or more radicals— Si(R' 1 )(R' 2 )- with R' 1 and R' 2 , which may be identical or different, representing a hydrogen atom, hydroxyl, (CrC4)alkyl or (Ci- C4)alkoxy, preferably a C1-C4 alkyl such as methyl; preferably, said alkylene radical denotes a (Ci-Cioo)alkylene radical optionally interrupted with one or more oxygen atoms and/or with one or more -SiMe2 radicals.
  • R represents a hydrogen atom or a C1-C4 alkyl radical such as NH and/or with one or more radicals— Si(R' 1
  • u is equal to 2 and T represents a divalent
  • (hetero)arylene group preferably arylene such as phenylene, more particularly 1 ,3- phenylene.
  • u is equal to 2 and T represents a divalent cycloalkylene group, preferably cyclohexylene, preferably substituted with one or more C1-C4 alkyl radicals such as methyl.
  • u is equal to 2 and T represents a divalent C1-C4 alkylene group such as methylene, ethylene or butylene.
  • u is equal to 3 and T represents i) a saturated or unsaturated, preferably saturated, linear or branched trivalent hydrocarbon-based radical containing from 1 to 20 carbon atoms, preferably from 1 to 10 carbon atoms, ii) an aromatic or nonaromatic, preferably aromatic, trivalent (hetero)cyclic radical containing 5 or 6 carbon atoms, preferably 6 carbon atoms, such as a trivalent 1 ,3,5- phenyl radical.
  • u is 2
  • Q represents an oxygen atom
  • ALK and ALK’ represent a (Ci-C4)alkylene, such as methylene.
  • the compound of formula (I) is such that u is 2 and:
  • - ALK represents a (CrC4)alkylene, such as methylene
  • - Z represents a carbonyl
  • - ALK represents a (CrC4)alkylene, such as methylene
  • the compound of formula (I) is such that u is 2 and:
  • m + p is 0; preferably, the other unit is such that m+p+q+z+y+w is 0.
  • the compound of formula (I) is chosen from the following compounds:
  • t being an integer ranging from 1 to 50, preferably from 3 to 30 and more preferentially from 5 to 20;
  • r being an integer ranging from 1 to 50, preferably from 3 to 30 and more preferentially from 5 to 20;
  • s being an integer ranging from 4 to 30, preferably from 5 to 10;
  • the process according to the present invention also comprises (ii) a step consisting in applying to the keratin fibers at least b) one compound comprising at least one amine group.
  • the compound comprising at least one amine group is chosen from:
  • the compound comprising at least one amine group may be chosen from amino silicones, nonsilicone polymers comprising at least one amine group, and mixtures thereof.
  • amino silicone means any silicone including at least one primary, secondary or tertiary amine function.
  • the weight-average molecular masses of these amino silicones may be measured by gel permeation chromatography (GPC) at room temperature (25°C), as polystyrene equivalent.
  • the columns used are m styragel columns.
  • the eluent is THF and the flow rate is 1 ml/minute. 200 mI of a 0.5% by weight solution of silicone in THF are injected. Detection is performed by refractometry and UV-metry.
  • amino silicones that may be used in the context of the invention are chosen from:
  • x' and y' are integers such that the weight-average molecular weight (Mw) ranges from 5000 to 500 000;
  • - G which may be identical or different, denotes a hydrogen atom or a phenyl, OH, Ci- Cs alkyl, for example methyl, or C Cs alkoxy, for example methoxy, group,
  • - a which may be identical or different, denotes 0 or an integer from 1 to 3, in particular
  • - b denotes 0 or 1 , in particular 1 ,
  • n + m and n are numbers such that the sum (n + m) varies from 1 to 2000 and in particular from 50 to 150, n possibly denoting a number from 0 to 1999 and notably from 49 to 149, and m possibly denoting a number from 1 to 2000 and notably from 1 to 10;
  • R' which may be identical or different, denotes a monovalent radical of formula - CqH2ql_ in which q is a number ranging from 2 to 8 and L is an optionally quaternized amine group chosen from the following groups:
  • R which may be identical or different, denotes hydrogen, phenyl, benzyl, or a saturated monovalent hydrocarbon-based radical, for example a C1-C20 alkyl radical;
  • Q denotes a linear or branched group of formula C r H 2r , r being an integer ranging from 2 to 6, preferably from 2 to 4; and
  • A- represents a cosmetically acceptable anion, notably a halide such as fluoride, chloride, bromide or iodide;
  • R 2 , R3 and R4 which may be identical or different, denote a C1-C4 alkyl radical or a phenyl group,
  • R5 denotes a C1-C4 alkyl radical or a hydroxyl group
  • - n is an integer ranging from 1 to 5
  • - m is an integer ranging from 1 to 5
  • - x is chosen such that the amine number ranges from 0.01 to 1 meq/g; d) the multiblock polyoxyalkylenated amino silicones of the type (AB)n, A being a polysiloxane block and B being a polyoxyalkylene block including at least one amine group,
  • the multiblock polyoxyalkylenated amino silicones of the type (AB)n are preferably formed from repeating units having the following general formulae:
  • - a is an integer greater than or equal to 1 , preferably ranging from 5 to 200 and more particularly ranging from 10 to 100;
  • - b is an integer ranging from 0 to 200, preferably ranging from 4 to 100 and more particularly ranging from 5 to 30;
  • - x is an integer ranging from 1 to 10 000 and more particularly from 10 to 5000;
  • - R" is a hydrogen atom or a methyl
  • R which may be identical different, represent a linear or branched divalent C2-C12 hydrocarbon-based radical, optionally including one or more heteroatoms such as oxygen; preferably, R denotes an ethylene radical, a linear or branched propylene radical, a linear or branched butylene radical or a radical
  • R denotes a radical
  • R’ which may be identical or different, represent a linear or branched divalent C2-C12 hydrocarbon-based radical, optionally including one or more heteroatoms such as oxygen; preferably, R’ denotes an ethylene radical, a linear or branched propylene radical, a linear or branched butylene radical or a radical
  • R’ denotes -CH(CH 3 )-CH 2 -.
  • the siloxane blocks preferably represent from 50 mol% to 95 mol% of the total weight of the silicone, more particularly from 70 mol% to 85 mol%.
  • the amine content preferably ranges from 0.02 to 0.5 meq/g of copolymer in a 30% solution in dipropylene glycol, more particularly from 0.05 to 0.2.
  • the weight-average molecular mass (Mw) of the silicone preferably ranges from 5000 to 1 000 000 and more particularly from 10 000 to 200 000.
  • the amino silicones are chosen from the amino silicones of formula (B).
  • the amino silicones of formula (B) may be chosen from the amino silicones corresponding to formulae (D), (E), (F), (G), (H), (J) and (K) below, and mixtures thereof.
  • the amino silicones corresponding to formula (B) are chosen from the silicones known as "trimethylsilyl amodimethicone" corresponding to formula (D):
  • n and n are numbers such that the sum (n + m) ranges from 1 to 2000 and in particular from 50 to 150, n possibly denoting a number from 0 to 1999 and notably from 49 to 149, and m possibly denoting a number from 1 to 2000 and notably from 1 to 10.
  • amino silicones corresponding to formula (B) are chosen from the silicones of formula (E) below:
  • n + m and n are numbers such that the sum (n + m) ranges from 1 to 1000, in particular from 50 to 250 and more particularly from 100 to 200; n possibly denoting a number from 0 to 999 and notably from 49 to 249 and more particularly from 125 to 175, and m possibly denoting a number from 1 to 1000, notably from 1 to 10 and more particularly from 1 to 5;
  • R1 , R2 and R3 which may be identical or different, represent a hydroxyl or C1-C4 alkoxy radical, at least one of the radicals R1 to R3 denoting an alkoxy radical.
  • the alkoxy radical is a methoxy radical.
  • the hydroxy/a I koxy mole ratio preferably ranges from 0.2: 1 to 0.4: 1 and preferably from 0.25: 1 to 0.35: 1 and more particularly is equal to 0.3: 1.
  • the weight-average molecular mass (Mw) of these silicones preferably ranges from 2000 to 1 000 000 and more particularly from 3500 to 200 000.
  • the amino silicones corresponding to formula (B) are chosen from the silicones of formula (F) below:
  • - p and q are numbers such that the sum (p + q) ranges from 1 to 1000, in particular from 50 to 350 and more particularly from 150 to 250; p possibly denoting a number from 0 to 999, notably from 49 to 349 and more particularly from 159 to 239, and q possibly denoting a number from 1 to 1000, notably from 1 to 10 and more particularly from 1 to 5;
  • R1 and R2 which are different, represent a hydroxyl or C1-C4 alkoxy radical, at least one of the radicals R1 or R2 denoting an alkoxy radical.
  • the alkoxy radical is a methoxy radical.
  • the hydroxy/a I koxy mole ratio generally ranges from 1 :0.8 to 1 : 1.1 and preferably from 1 :0.9 to 1 : 1 and more particularly is equal to 1 :0.95.
  • the weight-average molecular mass (Mw) of the silicone preferably ranges from 2000 to 200 000, even more particularly from 5000 to 100 000 and more particularly from 10 000 to 50 000.
  • the commercial products comprising silicones of structure (E) or (F) may include in their composition one or more other amino silicones whose structure is different from formula (E) or (F).
  • a product containing amino silicones of structure (E) is sold by the company Wacker under the name Belsil® ADM 652.
  • a product containing amino silicones of structure (F) is sold by the company Wacker under the name Fluid WR 1300®.
  • the oil-in-water emulsion may comprise one or more surfactants.
  • the surfactants may be of any nature but are preferably cationic and/or nonionic.
  • the number-mean size of the silicone particles in the emulsion generally ranges from 3 nm to 500 nanometers.
  • use is made of microemulsions with a mean particle size ranging from 5 nm to 60 nanometers (limits included) and more particularly from 10 nm to 50 nanometers (limits included).
  • use may be made according to the invention of the amino silicone microemulsions of formula (E) sold under the name Finish CT 96 E® or SLM 28020® by the company Wacker.
  • the amino silicones corresponding to formula (B) are chosen from the silicones of formula (G) below:
  • n + m and n are numbers such that the sum (n + m) ranges from 1 to 2000 and in particular from 50 to 150, n possibly denoting a number from 0 to 1999 and notably from 49 to 149, and m possibly denoting a number from 1 to 2000 and notably from 1 to 10;
  • A denotes a linear or branched alkylene radical containing from 4 to 8 carbon atoms and preferably 4 carbon atoms. This radical is preferably linear.
  • the weight-average molecular mass (Mw) of these amino silicones preferably ranges from 2000 to 1 000 000 and even more particularly from 3500 to 200 000.
  • a silicone corresponding to this formula is, for example, the Xiameter MEM 8299 Emulsion from Dow Corning.
  • the amino silicones corresponding to formula (B) are chosen from the silicones of formula (H) below:
  • n + m and n are numbers such that the sum (n + m) ranges from 1 to 2000 and in particular from 50 to 150, n possibly denoting a number from 0 to 1999 and notably from 49 to 149, and m possibly denoting a number from 1 to 2000 and notably from 1 to 10;
  • A denotes a linear or branched alkylene radical containing from 4 to 8 carbon atoms and preferably 4 carbon atoms. This radical is preferably branched.
  • the weight-average molecular mass (Mw) of these amino silicones preferably ranges from 500 to 1 000 000 and even more particularly from 1000 to 200 000.
  • a silicone corresponding to this formula is, for example, DC2-8566 Amino Fluid from Dow Corning.
  • the amino silicones corresponding to formula (B) are chosen from the silicones of formula (J) below:
  • - m and n are numbers ranging from 1 to 5000, and in particular n possibly denoting a number ranging from 10 to 2000 and notably from 100 to 1000, and in particular m possibly denoting a number from 1 to 100;
  • Ri and R2 which may be identical or different, preferably identical, represent a linear or branched, saturated or unsaturated alkyl radical comprising from 6 to 30 carbon atoms, preferably from 8 to 24 carbon atoms, preferably from 12 to 20 carbon atoms;
  • A denotes a linear or branched alkylene radical containing from 4 to 8 carbon atoms and preferably 4 carbon atoms; this radical is preferably branched.
  • A comprises from 3 to 6 carbon atoms, better still 4 carbon atoms;
  • A is branched.
  • A denotes the following divalent radicals: -CH2CH2CH2- or -CH 2 CH(CH 3 )CH 2 -.
  • Ri and R2 which may be identical or different, represent a saturated linear alkyl radical comprising 6 to 30 carbon atoms, preferably 8 to 24 carbon atoms, preferably 12 to 20 carbon atoms; in particular, Ri and R2 denote dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl radicals;
  • Ri and R2 which may be identical or different, are chosen from hexadecyl and octadecyl radicals.
  • amino silicone(s) of formula (J) are such that:
  • - n is a number ranging from 10 to 2000 and notably from 100 to 1000;
  • - m is a number ranging from 1 to 100;
  • Ri and R2 which may be identical or different, represent a saturated linear alkyl radical comprising from 6 to 30 carbon atoms, preferably from 8 to 24 carbon atoms and preferably from 12 to 20 carbon atoms; chosen in particular from dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl radicals; preferably, Ri and R2, which may be identical or different, are chosen from hexadecyl and octadecyl radicals; and
  • A comprises from 3 to 6 carbon atoms and preferably 4 carbon atoms; preferably, A is branched; more preferentially, A is chosen from the following divalent radicals: -CH2CH2CH2- and -CH 2 CH(CH 3 )CH 2 -.
  • amino silicones of formula (J) that are particularly preferred are those
  • the amino silicones corresponding to formula (B) are chosen from the silicones of formula (K) below:
  • n is such that the weight-average molecular weight (Mw) of the silicone ranges from 500 to 55 000.
  • amino silicone corresponding to formula (K) mention may be made of those sold under the names DMS-A11 , DMS-A12, DMS-A15, DMS-A21 , DMS-A31 , DMS-A32 and DMS-A35 by the company Gelest, and under the reference 481688 from Aldrich.
  • the amino silicones of formula (B) are chosen from the amino silicones of formulae (J) and (K), and mixtures thereof.
  • the amine derivatives of alkoxysilane may be chosen from the compounds of formula (L) below, oligomers thereof, hydrolysis products thereof and/or mixtures thereof:
  • Ri is a linear or branched, saturated or unsaturated, cyclic or acyclic C1-C6 hydrocarbon-based chain substituted with a group chosen from the following groups:
  • R Ci-C 2 o and notably C1-C6 alkyl optionally substituted with a radical including a silicon atom, C3-C40 cycloalkyl or C6-C30 aromatic),
  • Ri possibly being interrupted with a heteroatom (O, S, NH) or a carbonyl (CO) group
  • R 2 and R3 which may be identical or different, represent a linear or branched alkyl group comprising from 1 to 6 carbon atoms;
  • y denotes an integer ranging from 0 to 3;
  • z denotes an integer ranging from 0 to 3.
  • x denotes an integer ranging from 0 to 2;
  • oligomer refers to the polymerization products of the compounds of formula (L) including from 2 to 10 silicon atoms.
  • R 2 represents an alkyl group comprising from 1 to 4 carbon atoms, better still a linear alkyl group comprising from 1 to 4 carbon atoms, and preferably an ethyl group.
  • R 3 represents an alkyl group comprising from 1 to 4 carbon atoms, better still a linear alkyl group comprising from 1 to 4 carbon atoms, and preferably methyl or ethyl groups.
  • Ri is an acyclic chain.
  • the compounds of formula (L) include only one silicon atom in their structure.
  • Ri represents an alkyl group and even more preferentially a linear alkyl group comprising from 1 to 6 carbon atoms or a C 1 -C 6 aminoalkyl group.
  • z ranges from 1 to 3. Even more preferentially, z is equal to 3.
  • the amine derivatives of alkoxysilane are chosen from
  • APTES 3-aminopropyltriethoxysilane
  • AETES 3-aminoethyltriethoxysilane
  • APTES 3-aminopropyltriethoxysilane
  • AETES 3-aminoethyltriethoxysilane
  • the amine derivatives of alkoxysilane are chosen from 3-aminopropyltriethoxysilane (APTES), oligomers thereof, hydrolysis products thereof and mixtures thereof.
  • APTES 3-aminopropyltriethoxysilane
  • organic amines not comprising any silicon atoms may be chosen from:
  • alkanolamines such as mono-, di- and triethanolamines, mono-, di- and tri- (hydroxymethyl)aminomethanes, and derivatives thereof,
  • W is a (Ci-Ce)alkylene group such as propylene optionally substituted with a hydroxyl or amino group or a C1-C4 alkyl radical;
  • R x , R y , R z and R t which may be identical or different, represent a hydrogen atom or a C 1 -C 4 alkyl or C 1 -C 4 hydroxyalkyl radical.
  • amines of formula (A’) that may be mentioned include 1 ,3- diaminopropane, 1 ,3-diamino-2-propanol, spermine and spermidine.
  • alkanolamine means an organic amine comprising a primary, secondary or tertiary amine function, and one or more linear or branched C Cs alkyl groups bearing one or more hydroxyl radicals.
  • Organic amines chosen from alkanolamines such as monoalkanolamines,
  • dialkanolamines or trialkanolamines comprising one to three identical or different C1 -C4 hydroxyalkyl radicals are in particular suitable for performing the invention.
  • MAA monoethanolamine
  • diethanolamine triethanolamine
  • monoisopropanolamine diisopropanolamine
  • N,N-dimethylethanolamine 2-amino-2-methyl-1 -propanol
  • triisopropanolamine 2-amino-2-methyl-1 ,3-propanediol
  • 3-amino-1 ,2-propanediol 3-dimethylamino-1 ,2- propanediol and tris(hydroxymethylamino)methane.
  • amino acids that may be used are of natural or synthetic origin, in their L, D or racemic form, and include at least one acid function chosen more particularly from carboxylic acid, sulfonic acid, phosphonic acid and phosphoric acid functions.
  • the amino acids may be in neutral or ionic form.
  • the amino acids are basic amino acids comprising an additional amine function optionally included in a ring or in a ureido function.
  • Such basic amino acids are preferably chosen from those corresponding to formula (B) below, and also salts thereof:
  • R represents a group chosen from: imidazolyl, preferably imidazolyl-5-yl; -(CH 2 ) 3 -NH 2 ; -(CH 2 ) 2 -NH 2 ; -(CH 2 ) 2 N(H)-C(0)-NH 2 ; and -(CH 2 ) 2 -N(H)- C(NH)-NH 2 .
  • the compounds corresponding to formula (B) are histidine, lysine, arginine, ornithine and citrulline.
  • the organic amines may also be chosen from organic amines of heterocyclic type. Besides histidine that has already been mentioned in the amino acids, mention may be made in particular of pyridine, piperidine, imidazole, triazole, tetrazole and
  • the organic amines may also be chosen from amino acid dipeptides.
  • amino acid dipeptides that may be used in the present invention, mention may notably be made of carnosine, anserine and balenine.
  • the organic amines may also be chosen from compounds including a guanidine function.
  • amines of this type that may be used in the present invention, besides arginine, which has already been mentioned as an amino acid, mention may be made notably of creatine, creatinine, 1 ,1-dimethylguanidine, 1 , 1 -diethylguanidine, glycocyamine, metformin, agmatine, n-amidinoalanine, 3-guanidinopropionic acid, 4-guanidinobutyric acid and 2-([amino(imino)methyl]amino)ethane-1 -sulfonic acid.
  • Nonsilicone polymers comprising at least one amine group
  • the nonsilicone polymers comprising at least one amine group may be chosen from polyamines, polyamino acids, polysaccharides comprising at least one amine group, and mixtures thereof.
  • poly amines or“poly”amino acids means alkaline agents comprising at least two amino or amino acid groups linked to the same molecule; they are in particular polymers whose backbone comprises or is substituted with one or more amine groups or amino acid groups.
  • the polyamines may be chosen from poly((C2-C5)alkyleneimines), poly(allylamines), polyvinylamines and mixtures thereof.
  • the poly((C2-C5)alkyleneimines) may be chosen from polyethyleneimines, polypropyleneimines and mixtures thereof, preferably polyethyleneimines.
  • An example that may be mentioned of a polyethyleneimine that may be used according to the present invention is the product sold under the reference 46,852-3 by the company Aldrich Chemical.
  • poly(allylamine) As an example of a poly(allylamine) that may be used according to the present invention, mention may be made of the poly(allylamine) which may be sold under the reference 47,913-6 by the company Aldrich Chemical.
  • la poly-L-lysine for instance the product sold by the company JNC
  • Polysaccharides comprising at least one amine group
  • the nonsilicone polymers comprising at least one amine group are chosen from polysaccharides comprising at least one amine group. More preferentially, the polysaccharides comprising at least one amine group are chosen from the polysaccharides bearing monosaccharide units of formula (lla) below:
  • - n is an integer greater than or equal to 2, preferably ranging from 3 to 3000, more preferentially ranging from 5 to 2500, and better still ranging from 10 to 2300;
  • R a , R b and R c which may be identical or different for each monosaccharide unit, represent (1) a hydroxyl group, (2) a (CrC4)alkoxy group, the alkyl chain of which may be optionally substituted notably with one or more hydroxyl and/or carboxyl groups, (3) a carboxyl group, or (4) a group NR1R2 with Ri and R2, which may be identical or different, representing i) a hydrogen atom, ii) a (Ci-Ce)alkyl group that is optionally substituted, preferably with one or more hydroxyl or NH2 groups, iii) an aryl group such as phenyl, iv) an aryl(Ci-C4)alkyl group such as benzyl, v) a (hetero)cyclo(C5-C7)alkyl group such as cyclohexyl, morpholinyl, piperazinyl, piperidyl, vi
  • At least one of the radicals R a , R b or R c of at least one monosaccharide unit represents an NH2 group.
  • polysaccharides comprising at least one amine group are chosen from the polysaccharides bearing monosaccharide units of formula (Mb) below:
  • - n is an integer greater than or equal to 2, preferably ranging from 3 to 3000, more preferentially from 5 to 2500 and more preferentially from 10 to 2300;
  • At least one monosaccharide unit bears an amino group NH 2 .
  • the polysaccharides comprising at least one amine group are chosen from chitin, chitosan, derivatives thereof and mixtures thereof, more preferentially from chitin, chitosan and mixtures thereof, even more preferentially chitosan.
  • the process according to the present invention also comprises (iii) a step consisting in applying to the keratin fibers at least c) one coloring agent chosen from pigments, direct dyes and mixtures thereof.
  • the coloring agent(s) are chosen from pigments.
  • pigment is intended to denote a white or colored solid particle which is naturally insoluble in the hydrophilic and lipophilic liquid phases usually employed in cosmetics or which is rendered insoluble by formulation in the form of a lake, where appropriate. More particularly, the pigment has little or no solubility in aqueous- alcoholic media.
  • Pigments that may be mentioned include organic and mineral pigments such as those defined and described in Ullmann's Encyclopedia of Industrial Chemistry “Pigment organics”, 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
  • They may in particular be monoazo pigments, including b-naphthols,
  • monoazopyrrolone pigments or benzimidazolone pigments include monoazopyrrolone pigments or benzimidazolone pigments; diazo pigments, such as diazodiarylide pigments and bis(N-acetoacetarylide) pigments, or triazo or tetraazo pigments.
  • azo metal complex pigments Mention may also be made of azo metal complex pigments.
  • Other pigments are also advantageous, namely isoindolinone and isoindoline pigments, phthalocyanine pigments; quinacridone pigments; perinone pigments; perylene pigments; anthraquinone pigments such as hydroxyanthraquinone pigments; aminoanthraquinone pigments including acylaminoanthraquinones and azo anthraquinone pigments; heterocyclic anthraquinones; polycarbocyclic anthraquinone pigments, pyranthrone pigments; anthranthrone pigments;
  • DPP diketopyrrolopyrrole
  • triphenylmethane pigments quinophthalone pigments; and fluorescent pigments.
  • the dyes comprise one or more solubilizing groups such as -SO 3 H or -COOH, these dyes are made insoluble and consequently pigments by formation of a lake, i.e. by salification (e.g. Na, Ca, St, Ba, etc.) and divided mainly into b-naphthol and 2- hydroxy-3-naphthoic acid pigments "(BON) pigment lakes”.
  • salification e.g. Na, Ca, St, Ba, etc.
  • the pigment may be at least partly organic.
  • the pigment is an organic pigment.
  • the pigment is a mineral pigment.
  • D&C Red No. 6, D&C Red No. 7 (Cl 15850), D&C Red No. 17, D&C Red No. 21 , D&C Red No. 22, D&C Red No. 27, D&C Red No. 28, D&C Red No. 30, D&C Red No. 31 , D&C Red No. 33, D&C Red No. 34, D&C Red No. 36, FD&C Red No. 40, FD&C Red 40 lake, D&C Violet No. 2, Ext. D&C Violet No. 2, FD & C Blue No. 1 , D&C Yellow No. 6, FD&C Yellow No. 6, D&C Yellow No. 7, 25 Ext. D&C Yellow No. 7, D&C Yellow No. 8, D&C Yellow No. 10 or D&C Yellow No. 11 , it being understood that when said pigment is not naturally insoluble in the hydrophilic and lipophilic phases usually used in cosmetics, it is used in the form of a corresponding lake, as explained previously.
  • lakes examples include lakes based on barium, strontium, calcium or aluminum, or alternatively diketopyrrolopyrroles.
  • pigments with an optical effect such as particles including a natural or synthetic organic or mineral substrate, for example glass, acrylic resins, polyester, polyurethane, polyethylene terephthalate, ceramics or aluminas, said substrate being optionally covered with metal substances, for instance aluminum, gold, silver, platinum, copper or bronze, or with metal oxides, for instance titanium dioxide, iron oxide or chromium oxide.
  • a natural or synthetic organic or mineral substrate for example glass, acrylic resins, polyester, polyurethane, polyethylene terephthalate, ceramics or aluminas
  • metal substances for instance aluminum, gold, silver, platinum, copper or bronze, or with metal oxides, for instance titanium dioxide, iron oxide or chromium oxide.
  • They may also be nacres.
  • nacres means iridescent pigments, which are notably produced by certain molluscs in their shell, or alternatively which are synthesized.
  • the nacreous pigments may be chosen from mica coated with titanium or with bismuth oxychloride, titanium mica coated with iron oxides, titanium mica coated notably with ferric blue or with chromium oxide, titanium mica coated with an organic pigment of the abovementioned type, and also nacreous pigments based on bismuth oxychloride. Use may also be made of interference pigments, notably liquid-crystal or multilayer pigments.
  • pigments having a structure may be, for example, of sericite/brown iron oxide/titanium dioxide/silica type.
  • pigments having a structure may be, for example, of silica microsphere type containing iron oxide.
  • pigments that are most particularly suitable for use in the present invention, mention may be made notably of D&C Red No. 7, titanium oxide, chromium oxide, lakes of the pigments of D&C and FD&C type mentioned above, and notably D&C Red No. 22 lake, Yellow No. 6 lake and FD&C Blue No. 1 lake.
  • the pigments in accordance with the invention may be in the form of pigment powder or paste. They may be coated or uncoated.
  • the pigments in accordance with the invention may be chosen, for example, from white or colored pigments, lakes, pigments with special effects such as nacres or glitter flakes, and mixtures thereof.
  • white or colored mineral pigments examples include zirconium oxide or cerium oxide, chromium oxides, manganese violet, ultramarine blue, chromium hydrate and ferric blue.
  • white or colored organic pigments examples include nitroso, nitro, azo, xanthene, quinoline, anthraquinone and phthalocyanine compounds, compounds of metallic complex type, and isoindolinone, isoindoline, quinacridone, perinone, perylene, diketopyrrolopyrrole, thioindigo, dioxazine, triphenylmethane and quinophthalone compounds.
  • the white or colored organic pigments may be chosen from carmine, carbon blacks such as Black 2, aniline black, azo yellow, quinacridone, phthalocyanine blue, sorghum red, the blue pigments codified in the Color Index under the references Cl 42090, 69800, 69825, 73000, 74100, 74160, the yellow pigments codified in the Color Index under the references Cl 11680, 11710, 15985, 19140, 20040, 21100, 21108, 47000, 47005, the green pigments codified in the Color Index under the references Cl 61565, 61570, 74260, the orange pigments codified in the Color Index under the references Cl 11725, 15510, 45370, 71105, the red pigments codified in the Color Index under the references Cl 12085, 12120, 12370, 12420, 12490, 14700, 15525, 15580, 15620, 15630, 15800, 15850, 15865, 15880, 17200, 26100, 45
  • carbon blacks such as Black 2 or lakes such as D&C Red 7.
  • pigment pastes of organic pigments such as the products sold by the company Hoechst under the names:
  • the pigments in accordance with the invention may also be in the form of composite pigments, as described in patent EP 1 184 426. These composite pigments may be composed notably of particles including:
  • the term "lake” refers to dyes adsorbed onto insoluble particles, the assembly thus obtained remaining insoluble during use.
  • the inorganic substrates onto which the dyes are adsorbed are, for example, alumina, silica, calcium sodium borosilicate, calcium aluminum borosilicate and aluminum.
  • Examples of lakes that may be mentioned include the products known under the following names: D & C Red 21 (Cl 45 380), D & C Orange 5 (Cl 45 370), D & C Red 27 (Cl 45 410), D & C Orange 10 (Cl 45 425), D & C Red 3 (Cl 45 430), D & C Red 7 (Cl 15 850:1), D & C Red 4 (Cl 15 510), D & C Red 33 (Cl 17 200), D & C Yellow 5 (Cl 19 140), D & C Yellow 6 (Cl 15 985), D & C Green (Cl 61 570), D & C Yellow 10 (Cl 77 002), D & C Green 3 (Cl 42 053) or D & C Blue 1 (Cl 42 090).
  • D & C Red 21 Cl 45 380
  • D & C Orange 5 Cl 45 370
  • D & C Red 27 Cl 45 410
  • D & C Orange 10 Cl 45 425
  • pigments with special effects means pigments that generally create a colored appearance (characterized by a certain shade, a certain vivacity and a certain level of luminance) that is nonuniform and that changes as a function of the conditions of observation (light, temperature, angles of observation, etc.). They thereby differ from white or colored pigments, which afford a standard uniform opaque, semi-transparent or transparent shade.
  • pigments with special effects include white nacreous pigments such as mica coated with titanium or with bismuth oxychloride, colored nacreous pigments such as mica coated with titanium and with iron oxides, mica coated with titanium and notably with ferric blue or with chromium oxide, mica coated with titanium and with an organic pigment as defined previously, and also nacreous pigments based on bismuth oxychloride.
  • Pigments with an interference effect which are not attached to a substrate, such as liquid crystals (Helicones HC from Wacker) or interference holographic glitter flakes (Geometric Pigments or Spectra f/x from Spectratek).
  • Pigments with special effects also comprise fluorescent pigments, whether these are substances that are fluorescent in daylight or that produce an ultraviolet fluorescence, phosphorescent pigments, photochromic pigments, thermochromic pigments and quantum dots, sold, for example, by the company Quantum Dots Corporation.
  • Quantum dots are luminescent semiconductor nanoparticles that are capable of emitting, under light excitation, radiation with a wavelength of between 400 nm and 700 nm. These nanoparticles are known from the literature. In particular, they may be manufactured according to the processes described, for example, in US 6 225 198 or US 5 990 479, in the publications cited therein and also in the following publications: Dabboussi B.O. et al.,“(CdSe)ZnS core-shell quantum dots: synthesis and characterisation of a size series of highly luminescent nanocrystallites”, Journal of Physical Chemistry B, voi.
  • the pigments in accordance with the invention are preferably colored pigments.
  • the size of a pigment other than the nacres in solution generally ranges from 10 nm to 10 pm, preferably from 50 nm to 5 pm and even more preferentially from 100 nm to 3 pm.
  • the size of a nacre in solution is generally from 1 to 200 pm, preferably from 1 to 80 pm and even more preferentially from 1 to 50 pm.
  • mineral pigments examples that may be mentioned include titanium dioxide (rutile or anatase) optionally surface-treated and codified in the Color Index under the reference Cl 77891 ; black, yellow, red and brown iron oxides, codified under the references Cl 77499, 77492 and 77491 ; manganese violet (Cl 77742); ultramarine blue (Cl 77007); hydrated chromium oxide (Cl 77289); ferric blue
  • organic pigments that may be mentioned, for example, are the pigment Yellow 3 sold notably under the trade name Jaune Covanor W 1603 by the company Wackherr (Cl 17710), D & C Red No. 19 (Cl 45170), D & C Red No. 9 (Cl 15585), D
  • nacreous pigments which may be chosen notably from white nacreous pigments such as mica coated with titanium oxide or bismuth oxide; colored nacreous pigments such as titanium mica with iron oxides, titanium mica with ferric blue or with chromium oxide, titanium mica with an organic pigment of the abovementioned type, and also those based on bismuth oxychloride.
  • Pigment pastes of organic pigment are used more particularly, such as the products sold by the company Hoechst under the name:
  • the dyestuff(s) are advantageously chosen from pigments, preferably from white organic pigments, colored organic pigments, and mixtures thereof, and more preferentially carbon blacks, such as Black 2, lakes, such as D&C Red 7, and mixtures thereof.
  • the coloring agents may be chosen from direct dyes.
  • direct dye means natural and/or synthetic dyes, other than oxidation dyes. These are dyes that will spread superficially on the fiber.
  • They may be ionic or nonionic, preferably cationic or nonionic, i.e. as sole dyes.
  • These direct dyes are chosen, for example, from neutral, acidic or cationic
  • nitrobenzene direct dyes neutral, acidic or cationic azo direct dyes
  • tetraazapentamethine dyes neutral, acidic or cationic quinone and in particular anthraquinone dyes, azine direct dyes, triaryl methane direct dyes, azomethine direct dyes and natural direct dyes.
  • Suitable direct dyes include azo direct dyes; (poly)methine dyes such as cyanines, hemicyanines and styryl dyes; carbonyl dyes; azine dyes; nitro(hetero)aryl dyes; tri(hetero)arylmethane dyes; porphyrin dyes;
  • phthalocyanine dyes and natural direct dyes, alone or as mixtures.
  • the direct dye(s) contain at least one quaternized cationic
  • chromophore or at least one chromophore bearing a quaternized or quaternizable cationic group.
  • the direct dyes comprise at least one quaternized cationic chromophore.
  • dyes As direct dyes according to the invention, mention may be made of the following dyes: acridines; acridones; anthranthrones; anthrapyrimidines; anthraquinones;
  • naphtholactams ; naphthoquinones; nitro, notably nitro(hetero)aromatics; oxadiazoles; oxazines; perilones; perinones; perylenes; phenazines; phenoxazine;
  • phenothiazines phthalocyanine; polyenes/carotenoids; porphyrins; pyranthrones; pyrazolanthrones; pyrazolones; pyrimidinoanthrones; pyronines; quinacridones; quinolines; quinophthalones; squaranes; tetrazoliums; thiazines, thioindigo;
  • thiopyronines for the cationic azo dyes, mention may be made particularly of those resulting from the cationic dyes described in Kirk-Othmer’s Encyclopedia of Chemical Technology, “Dyes, Azo”, J. Wiley & Sons, updated on April 19, 2010.
  • the direct dye(s) are chosen from cationic dyes known as "basic dyes".
  • cationic quinone dyes those mentioned in the abovementioned Colour Index International are suitable for use and, among these, mention may be made, inter alia, of the following dyes:
  • azine dyes that are suitable for use, mention may be made of those listed in the Colour Index International, for example the following dyes:
  • the cationic direct dyes are chosen from those resulting from dyes of azo and hydrazono type.
  • the direct dyes are cationic azo dyes, described in EP 850 636, FR 2 788 433, EP 920 856, WO 99/48465, FR 2 757 385, EP 850 637, EP 918 053, WO 97/44004, FR 2 570 946, FR 2 285 851 , DE 2 538 363, FR 2 189 006, FR 1 560 664, FR 1 540 423, FR 1 567 219, FR 1 516 943, FR 1 221 122, DE 4 220 388, DE 4 137 005, WO 01/66646, US 5 708 151 , WO 95/01772, WO 515 144, GB 1 195 386, US 3 524 842, US 5 879 413, EP 1 062 940, EP 1 133 976, GB 738 585, DE 2 527 638, FR 2 275 462, GB 1974-27645, Acta
  • the cationic direct dye(s) comprise(s) a quaternary ammonium group; more preferentially, the cationic charge is endocyclic.
  • cationic radicals are, for example, a cationic radical:
  • an endocyclic charge such as comprising a cationic heteroaryl group chosen from: acridinium, benzimidazolium, benzobistriazolium, benzopyrazolium, benzopyridazinium, benzoquinolium, benzothiazolium, benzotriazolium,
  • Het + represents a cationic heteroaryl radical, preferentially bearing an endocyclic cationic charge, such as imidazolium, indolium or pyridinium, which is optionally substituted, preferentially with at least one (C-i-Cs) alkyl group such as methyl;
  • Ar + represents an aryl radical, such as phenyl or naphthyl, bearing an exocyclic cationic charge, preferentially ammonium, particularly tri(Ci- C 8 )alkylammonium, such as trimethylammonium;
  • Ar represents an aryl group, notably phenyl, which is optionally substituted, preferentially with one or more electron-donating groups such as i) optionally substituted (Ci-Cs)alkyl, ii) optionally substituted (Ci-C 8 )alkoxy, iii) (di)(Ci- C 8 )(alkyl)amino optionally substituted on the alkyl group(s) with a hydroxyl group, iv) aryl(Ci-C 8 )alkylamino, v) optionally substituted N-(Ci-Cs)alkyl-N- aryl(Ci-C 8 )alkylamino or alternatively Ar represents a julolidine group;
  • Ar represents an optionally substituted (hetero)aryl group, such as phenyl or pyrazolyl, which are optionally substituted, preferentially with one or more (C-i- C 8 )alkyl, hydroxyl, (di)(Ci-C 8 )(alkyl)amino, (Ci-Cs)alkoxy or phenyl groups;
  • R a and R b which may be identical or different, represent a hydrogen atom or a (Ci-C 8 )alkyl group, which is optionally substituted, preferentially with a hydroxyl group;
  • R a and R b represent a hydrogen atom or a (Ci-C4)alkyl group optionally substituted with a hydroxyl group;
  • Q represents an organic or mineral anionic counterion, such as a halide or an alkyl sulfate.
  • R 1 represents a (CrC4)alkyl group such as methyl
  • R 2 and R 3 which may be identical or different, represent a hydrogen atom or a (Ci- C4)alkyl group, such as methyl;
  • R 4 represents a hydrogen atom or an electron-donating group such as optionally substituted (Ci-Cs)alkyl, optionally substituted (Ci-Cs)alkoxy, or (di)(Cr
  • R 4 is a hydrogen atom
  • - Z represents a CH group or a nitrogen atom, preferentially CH
  • - Q is an anionic counterion as defined previously, in particular a halide, such as chloride, or an alkyl sulfate, such as methyl sulfate or mesyl.
  • the dyes of formulae (111-1) and (V-1) are chosen from Basic Red 51 , Basic Yellow 87 and Basic Orange 31 or derivatives thereof:
  • Q being an anionic counterion as defined previously, in particular a halide, such as chloride, or an alkyl sulfate, such as methyl sulfate or mesityl.
  • the direct dyes are fluorescent, that is to say that they contain at least one fluorescent chromophore as defined previously.
  • Fluorescent dyes that may be mentioned include the radicals resulting from the following dyes: acridines, acridones, benzanthrones, benzimidazoles,
  • benzimidazolones benzindoles, benzoxazoles, benzopyrans, benzothiazoles, coumarins, difluoro ⁇ 2-[(2H-pyrrol-2-ylidene-kN)methyl]-1 H-pyrrolato-kN ⁇ borons (BODIPY ® ), diketopyrrolopyrroles, fluorindines, (poly)methines (notably cyanines and styryls/hemicyanines), naphthalimides, naphthanilides, naphthylamines (such as dansyls), oxadiazoles, oxazines, perilones, perinones, perylenes,
  • polyenes/carotenoids polyenes/carotenoids, squaranes, stilbenes and xanthenes.
  • the fluorescent dye(s) are cationic and comprise at least one quaternary ammonium radical, such as those of formula (VII) below:
  • W+ represents a cationic heterocyclic or heteroaryl group, particularly comprising a quaternary ammonium optionally substituted with one or more (Ci-C 8 )alkyl groups, optionally substituted notably with one or more hydroxyl groups;
  • Ar representing an aryl group such as phenyl or naphthyl, optionally substituted preferentially with i) one or more halogen atoms such as chlorine or fluorine; ii) one or more (Ci-C 8 )alkyl groups, preferably of C1-C4 such as methyl; iii) one or more hydroxyl groups; iv) one or more (Ci-Cs)alkoxy groups such as methoxy; v) one or more hydroxy(Ci-Cs)alkyl groups such as hydroxyethyl, vi) one or more amino or (di)(Ci-C 8 )alkylamino groups, preferably with the C1-C4 alkyl part optionally substituted with one or more hydroxyl groups, such as (di)hydroxyethylamino, vii) with one or more acylamino groups; viii) one or more heterocycloalkyl groups such as piperazinyl, piperidyl or 5-
  • n represents an integer ranging from 1 to 4; in particular, m is 1 or 2; more preferentially 1 ;
  • Rc and R d which may be identical or different, represent a hydrogen atom or an optionally substituted (Ci-Cs)alkyl group, preferentially of C1-C4, or alternatively R c contiguous with W + and/or R d contiguous with Ar form, with the atoms that bear them, a (hetero)cycloalkyl; particularly, R c is contiguous with W + and they form a (hetero)cycloalkyl such as cyclohexyl;
  • Q is an organic or mineral anionic counterion as defined previously.
  • the process may comprise:
  • the process may comprise:
  • the process may comprise:
  • steps (i), (ii) and (iii) of the process are performed simultaneously by applying to the keratin fibers a composition (Ci) comprising:
  • Composition (Ci) may optionally comprise at least one organic solvent, preferably chosen from:
  • - monoalcohols comprising a hydroxyl group and a Ci-Ce(alkyl) and preferably Ci- C4(alkyl) group such as methyl, ethyl or (iso)propyl;
  • polyols comprising from 2 to 30 hydroxyl groups and a (C2-Cs)alkyl group, preferably a (C2-C4)alkyl group; and mixtures thereof.
  • the organic solvent is chosen from monoalcohols and polyols comprising two hydroxyl groups, even more preferentially from ethanol and polyols comprising two hydroxyl groups and at least three carbon atoms, most preferentially from ethanol, propylene glycol (1 ,2-propanediol); 1 ,3-propanediol; 1 ,3-butylene glycol; 1 ,2-pentanediol; dipropylene glycol; hexylene glycol; pentylene glycol; butylene glycol; glycerol; ethylene glycol, and mixtures thereof.
  • Composition (Ci) may comprise a total content of compounds of formula (I) ranging from 0.01 % to 20%, preferably from 0.05% to 15%, more preferentially from 0.1% to 10%, even more preferentially from 0.5% to 5%, most preferentially from 1 % to 5% by weight relative to the total weight of composition (Ci).
  • Composition (Ci) may comprise a total content of compounds comprising at least one amine group ranging from 0.01 % to 25%, preferably from 0.05% to 15%, more preferentially from 1% to 10% by weight relative to the total weight of composition (Ci).
  • Composition (Ci) may comprise a total content of coloring agents ranging from 0.05% to 10% and preferably from 0.5% to 5% by weight relative to the total weight of composition (Ci).
  • Composition (Ci) may comprise a total content of organic solvents ranging from 45% to 99.7%, preferably from 50% to 99%, more preferentially from 60% to 80% by weight relative to the total weight of composition (Ci).
  • the pH of composition (Ci) may be less than or equal to 10; preferably, the pH of composition (Ci) may range from 3 to 9; more preferentially, the pH of composition (Ci) may range from 4 to 8.
  • the pH of the composition may be adjusted with a compound known to those skilled in the art.
  • steps (i), (ii) and (iii) may be performed by applying to the keratin fibers:
  • composition (C ⁇ ) comprising a) the compound(s) of formula (I) as defined above;
  • composition (C 3 ) comprising b) the compound(s) comprising at least one amine group as defined above;
  • composition (C ⁇ ) and/or composition (C3) comprise c) the coloring agent(s) as defined above;
  • composition (C ⁇ ) is applied before composition (C3) or composition (C3) is applied before composition (C2).
  • composition (C ⁇ ) does not comprise any compound comprising at least one amine group and composition (C3) does not comprise any compound of formula (I).
  • Compositions (C ⁇ ) and/or (C3) may optionally comprise at least one organic solvent.
  • organic solvents as defined above may also be used in compositions (C ⁇ ) and/or (Cs).
  • compositions (Ci), (C ⁇ ) and (C3) used in the process according to the invention may also comprise at least one common cosmetic ingredient other than the compounds described previously, notably chosen from surfactants, notably nonionic or cationic surfactants, solid or liquid fatty substances, thickeners, in particular polysaccharide- based thickeners, nonsilicone cationic polymers, silicones, sunscreens; moisturizers; antidandruff agents; antioxidants; chelating agents; nacreous agents and opacifiers; plasticizers or coalescers; fillers; fragrances; silanes other than the amine derivatives of alkoxysilane; crosslinking agents.
  • the compositions may comprise several cosmetic ingredients featured in the above list.
  • the usual cosmetic ingredients may be present in usual amounts, which may be readily determined by a person skilled in the art and which may be, for each ingredient, between 0.01% and 80% by weight. A person skilled in the art will take care to select the ingredients included in the composition, and also the amounts thereof, so that they do not harm the properties of the compositions of the present invention.
  • Compositions (Ci), (C ⁇ ) and (C 3 ) used in the process according to the invention may be in any presentation form conventionally used, and notably in the form of an aqueous, alcoholic or aqueous-alcoholic or oily solution or suspension; a solution or a dispersion of the lotion or serum type; an emulsion, notably of liquid or semiliquid consistency of the O/W, W/O or multiple type; a suspension or emulsion of soft consistency of the (O/W) or (W/O) cream type; an aqueous or anhydrous gel, or any other cosmetic form.
  • compositions may be packaged in pump-action bottles or in aerosol containers, so as to apply the composition in vaporized (lacquer) form or in the form of a mousse.
  • Such packaging forms are indicated, for example, when it is desired to obtain a spray or a mousse, for treating the hair.
  • the composition preferably comprises at least one propellant.
  • compositions (Ci), (C ⁇ ) and (C 3 ) which have just been described may be applied to keratin fibers.
  • the bath ratio of the applied compositions i.e. the weight amount of applied composition relative to the weight of treated keratin fibers, may range from 0.1 to 10, preferably from 0.2 to 5, more preferentially from 0.5 to 3.
  • the term "bath ratio" means the ratio between the total weight of the applied composition and the total weight of keratin fibers to be treated.
  • Compositions (Ci), (C ⁇ ) and (C 3 ) of the invention may be applied to wet or dry keratin fibers, preferably wet or dry hair, preferably to dry hair.
  • each of the compositions (Ci), (C ⁇ ) and (C 3 ) may be followed by a leave-on time.
  • the leave-on time namely the time of contact of the composition on the hair, is preferably at least 5 minutes, preferably ranging from 10 to 60 minutes. Rinsing of the hair may optionally be envisaged after applying the last composition and optionally the leave-on time.
  • the hair may then optionally be wrung dry, preferably wrung dry.
  • the process according to the present invention also comprises, following the set of steps (i) to (iii), a step (iv) of heat treatment of the keratin fibers at a temperature ranging from 40°C to 230°C, preferably from 60°C to 190°C, more preferably from 60°C to 180°C.
  • the heat treatment step has a duration ranging from 5 seconds to 1 hour, preferably ranging from 5 seconds to 1 minute, per lock of hair.
  • This heat treatment step is generally performed using a heating tool such as a straightening iron, a curling iron, a crimping iron, a waving iron, a steam iron, a hood, a hairdryer, an infrared heating system or a heating roller, preferably using a straightening iron.
  • a heating tool such as a straightening iron, a curling iron, a crimping iron, a waving iron or a steam iron
  • the keratin fibers may be dried beforehand, naturally or using a hairdryer.
  • composition (Ci) comprising:
  • composition (Ci) described in the context of the process according to the present invention also apply to composition (Ci) per se.
  • a subject of the present invention is a multi-compartment device comprising:
  • composition (C ⁇ ) comprising a) the compound(s) of formula (I) as defined above, and
  • composition (C 3 ) different from composition (C 2 ), composition (C 3 ) comprising b) the compound(s) comprising at least one amine group as defined above;
  • composition (C 2 ) and/or composition (C 3 ) comprise c) the coloring agent(s) as defined above.
  • composition (C ⁇ ) does not comprise any compound comprising at least one amine group and composition (C 3 ) does not comprise any compound of formula (I).
  • compositions (C ⁇ ) and (C 3 ) described in the context of the process according to the present invention also apply to compositions (C ⁇ ) and (C 3 ) included in the multi-compartment device.
  • Example 1 The following compositions were prepared.
  • a lock of hair (hair of natural type, 90% gray - 1 g, 20 cm long) is placed in a trough.
  • the compositions mentioned in step 1 of the table below are mixed and then applied to the lock.
  • the lock is combed, left to stand for 10 minutes and then dried with a hairdryer.
  • the lock is placed in a new trough.
  • the compositions mentioned in step 2 of the table below are mixed and then applied to the lock.
  • the lock is combed, left to stand for 10 minutes and then dried with a hairdryer.
  • the lock is subjected to a heat treatment, it is suspended vertically and then subjected to a heat treatment which consists of three successive passes with a straightening iron at 190°C (Babyliss PRO, EP technology 5.0 sold by the company Babyliss). Spectrophotometric measurements of the L*a*b* values are then taken.
  • the locks are then shampooed five times.
  • the shampoo washing consists of five cycles.
  • a cycle consists of soaking the lock in an aqueous 3% solution of sodium laureth sulfate adjusted to pH 8 with sodium hydroxide, for 15 seconds, followed by soaking the lock in a bath of clean water for 15 seconds, and drying with a hairdryer. Spectrophotometric measurements of the L*a*b* values are then taken.
  • Spectrophotometric measurements The color of the locks is evaluated by colorimetry in the CIE L* a* b* system, using a Minolta CM 3600 spectrocolorimeter (illuminant D65, angle 10°, specular component included).
  • L* represents the intensity of the color
  • a* indicates the green/red color axis
  • b* the blue/yellow color axis. The smaller the value of L*, the darker and more powerful the coloring.
  • the resistance of the color to repeat shampooing corresponds to the variation in coloring between the locks of hair before and after repeated shampooing. It is defined by (DE**) according to the following equation:
  • L*, a* and b* represent the values measured on locks of hair after dyeing and L1 *, a1* and b1* represent the values measured on respective locks of hair washed with the shampoo.
  • the resistance of the coloring to shampooing is better in the presence of a step of heat treatment of the hair.
  • the color transfer onto a manufactured cotton fabric from the company Testfabrics Inc. (reference CrockSquares) is evaluated visually.
  • the fabric (5 cm * 5 cm) is moistened with water (2 ml_) and the fabric is then held in contact with the lock which has been dyed beforehand and after five shampoo washes, at a constant pressure using a finger.
  • the color transfer onto the fabric is then evaluated. The results are given in the table below.
  • compositions B1 and B2 were prepared by mixing the intermediate compositions together and stirring for 5 minutes.
  • the shampoo protocol consisted of 5 shampoo cycles. One cycle consisted of moistening the swatch under running tap water set at 37°C, applying 0.5g DOP shampoo, massaging the swatch for 15 seconds with the fingers and then rinsing the swatch for 15 seconds under running tap water set at 37°C. After the final shampoo, the hair was dried using a hairdryer, left suspended for 1 hour and then the color of all the swatches assessed by spectrocolorimetry.
  • the color of the locks is evaluated by colorimetry in the CIE L* a* b* system, using a Minolta CM 3600 spectrocolorimeter (illuminant D65, angle 10°, specular component included).
  • Swatch 2 colored using Formula B1 containing a triscarbonate ingredient and not treated with the flat iron gives slightly lower shampoo fastness results than Swatch 1 showing that the heat treatment used in swatch 1 improves shampoo resistance.
  • Swatch 4 colored using Formula B2 containing a monocarbonate (propylene carbonate) ingredient and not treated with the flat iron gives the poorest shampoo resistance and is unsatisfactory.

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Abstract

La présente invention concerne un procédé de coloration de fibres kératiniques, comprenant l'application sur les fibres kératiniques de a) au moins un ester de carbonate particulier, b) au moins un composé comprenant au moins un groupe amine et c) au moins un colorant choisi parmi les pigments, les colorants directs et leurs mélanges.
PCT/EP2020/067883 2019-06-27 2020-06-25 Procédé de coloration de fibres kératiniques à l'aide d'un polycarbonate cyclique particulier, composé comprenant au moins un groupe amine et un colorant, composition et dispositif WO2020260486A1 (fr)

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FR1906998A FR3097752B1 (fr) 2019-06-27 2019-06-27 Procédé de coloration des fibres kératiniques mettant en œuvre un polycarbonate cyclique particulier, un composé comprenant au moins un groupement amine et un agent colorant, composition et dispositif
FRFR1906998 2019-06-27

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FR1221122A (fr) 1958-02-25 1960-05-31 Thera Chemie G M B H Produits de teinture pour les cheveux
FR1516943A (fr) 1966-01-10 1968-02-05 Oreal Colorants basiques utilisables pour la teinture des cheveux
FR1540423A (fr) 1966-07-25 1968-09-27 Oreal Nouveaux colorants, leurs procédés de fabrication et leurs applications
GB1195386A (en) 1966-08-05 1970-06-17 Sandoz Ltd Water-Soluble Cationic Monoazo-Dyestuffs and their manufacture and use
FR1560664A (fr) 1967-02-22 1969-03-21
FR1567219A (fr) 1967-03-01 1969-05-16
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FR2189006A1 (fr) 1972-06-19 1974-01-25 Oreal
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DE4137005A1 (de) 1991-11-11 1993-05-13 Bitterfeld Wolfen Chemie Mittel zum faerben von haaren
DE4220388A1 (de) 1992-06-22 1993-12-23 Bitterfeld Wolfen Chemie Kationische Azofarbstoffe zum Färben von Keratinmaterialien
WO1995001772A1 (fr) 1993-07-05 1995-01-19 Ciba-Geigy Ag Procede de teinture de fibres keratiniques
WO1995015144A1 (fr) 1993-11-30 1995-06-08 Ciba-Geigy Ag Colorants cationiques pour fibres keratiniques
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EP0850636A1 (fr) 1996-12-23 1998-07-01 L'oreal Composition de teinture d'oxydation des fibres kératiniques et procédé de teinture mettant en oeuvre cette composition
FR2757385A1 (fr) 1996-12-23 1998-06-26 Oreal Composition de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition
EP0850637A1 (fr) 1996-12-23 1998-07-01 L'oreal Composition de teinture d'oxydation des fibres kératiniques et procédé de teinture mettant en oeuvre cette composition
EP0860636A1 (fr) 1997-02-20 1998-08-26 Hutchinson Dispositif de liaison étanche entre des canaux
EP0918053A1 (fr) 1997-11-21 1999-05-26 L'oreal Nouveaux composés azoíques, utilisation pour la teinture, compositions les contenant et procédés de teinture.
US5990479A (en) 1997-11-25 1999-11-23 Regents Of The University Of California Organo Luminescent semiconductor nanocrystal probes for biological applications and process for making and using such probes
EP0920856A1 (fr) 1997-12-05 1999-06-09 L'oreal Procédé de teinture directe en deux étapes des fibres kératiniques mettant en oeuvre des colorants directs basiques
EP1062940A1 (fr) 1998-02-10 2000-12-27 Yamahatsu Sangyo Kaisha, Ltd. Composition d'agent pour permanente ayant un effet colorant et son procede de coloration des cheveux
WO1999048465A1 (fr) 1998-03-20 1999-09-30 L'oreal Composition de teinture d'oxydation des fibres keratiniques contenant un derive azo de 3-aminopyridine et procede de teinture mettant en oeuvre cette composition
FR2788433A1 (fr) 1999-01-19 2000-07-21 Oreal Utilisation de composes phenyl-azo-benzeniques cationiques en teinture des fibres keratiniques, compositions tinctoriales et procedes de teinture
US6225198B1 (en) 2000-02-04 2001-05-01 The Regents Of The University Of California Process for forming shaped group II-VI semiconductor nanocrystals, and product formed using process
WO2001066646A1 (fr) 2000-03-09 2001-09-13 Ciba Specialty Chemicals Holding Inc. Procede servant a teindre des cheveux au moyen de colorants cationiques
EP1133975A2 (fr) 2000-03-17 2001-09-19 Kao Corporation Teinture de cheveux
EP1133976A2 (fr) 2000-03-17 2001-09-19 Kao Corporation Teinture pour des cheveux
EP1184426A2 (fr) 2000-09-01 2002-03-06 Toda Kogyo Corporation Particules composites, procédé de préparation, pigment et peinte, et composition de résine les utilisants
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CN114763438B (zh) * 2021-01-14 2023-08-11 万华化学集团股份有限公司 一种有机硅固化配方及固化方法和由其制备的硅橡胶

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