EP3937889A1 - Procédé de coloration de matière kératinique, comprenant l'utilisation d'un composé organique du silicium, un composé colorant et un mélange de silicones - Google Patents

Procédé de coloration de matière kératinique, comprenant l'utilisation d'un composé organique du silicium, un composé colorant et un mélange de silicones

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Publication number
EP3937889A1
EP3937889A1 EP20707613.4A EP20707613A EP3937889A1 EP 3937889 A1 EP3937889 A1 EP 3937889A1 EP 20707613 A EP20707613 A EP 20707613A EP 3937889 A1 EP3937889 A1 EP 3937889A1
Authority
EP
European Patent Office
Prior art keywords
agent
group
stands
acid
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP20707613.4A
Other languages
German (de)
English (en)
Inventor
Rene Krohn
Thomas Hippe
Stefan Hoepfner
Jessica Brender
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP3937889A1 publication Critical patent/EP3937889A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585—Organosilicon compounds
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated 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
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/892—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a hydroxy group, e.g. dimethiconol
    • 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
    • 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
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • 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
    • 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
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes
    • 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
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes
    • A61K2800/432—Direct dyes
    • A61K2800/4324—Direct dyes in 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
    • A61K2800/59—Mixtures
    • A61K2800/594—Mixtures of polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits
    • A61K2800/884—Sequential application
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/95—Involves in-situ formation or cross-linking of polymers

Definitions

  • a method of coloring keratinic material comprising the use of an organosilicon compound, a coloring compound and a mixture of silicones
  • the present application relates to a method for coloring keratinic material, in particular human hair, which comprises the use of three different agents (a), (b) and (c).
  • the agent (a) contains at least one organic silicon compound.
  • the agent (b) contains at least one coloring compound from the group of pigments and / or substantive dyes.
  • Agent (c) is characterized by a mixture of selected silicones.
  • a second subject of this application is a multi-component packaging unit (kit-of-parts) for dyeing keratinic material, in particular human hair, which comprises means (a), (b) and (c) separately packaged in three different containers.
  • kit-of-parts for dyeing keratinic material, in particular human hair
  • Oxidation colorants contain oxidation dye precursors, so-called developer components and coupler components, which, under the influence of oxidizing agents such as hydrogen peroxide, form the actual dyes with one another. Oxidation dyes are characterized by very long-lasting coloring results.
  • Color pigments known. Color pigments are generally understood to mean insoluble, coloring substances. These are present undissolved in the form of small particles in the coloring formulation and are only deposited on the outside of the hair fibers and / or the skin surface. Therefore, they can usually be removed without residue by a few washes with detergents containing surfactants. Various products of this type are available on the market under the name of hair mascara. If the user wants his hair to be colored for a particularly long time, the use of oxidative coloring agents has so far been his only option. But despite multiple
  • EP 2168633 B1 deals with the problem of producing long-lasting hair colorations using pigments.
  • the document teaches that when a combination of pigment, organic silicon compound, hydrophobic polymer and a solvent is used, the hair can be colored which should be particularly resistant to shampooing.
  • WO 2018/115059 A1 a dyeing process is described which takes place in several steps.
  • One step involves the application of an organosilane, and in a further step a substantive dye is applied to the hair. With this process too, dyeings with good wash fastnesses are to be achieved.
  • the object of the present invention was to provide a dyeing system which has fastness properties that are comparable to oxidative dyeing. especially the
  • wash fastnesses should be excellent, but the oxidation dye precursors usually used for this purpose should be avoided.
  • a search has been made for a technology which enables those known from the prior art
  • coloring compounds such as pigments or direct dyes
  • Silicon compound contains at least one pigment and / or a substantive dye
  • the agent (c) contains a mixture of selected hydroxy-terminated silicones.
  • a first object of the present invention is a method for coloring keratinic material, in particular human hair, comprising the following steps:
  • an agent (b) on the keratinous material the agent (b) containing at least one coloring compound from the group of pigments and / or substantive dyes,
  • agent (c) on the keratin material, the agent (c) containing:
  • (c2) a reaction product of a hydroxy-terminated polyorganosiloxane with an acid and / or an alcohol and / or a wax.
  • Keratinic material is understood to mean hair, skin, and nails (such as fingernails and / or toenails, for example). Furthermore, wool, furs and feathers also fall under the definition of keratinic material.
  • Keratinic material is preferably understood to mean human hair, human skin and human nails, in particular fingernails and toenails. Keratinic material is very particularly preferably understood to mean human hair.
  • keratinic material especially human hair, applied.
  • the three means (a), (b) and (c) are different from each other.
  • keratinic material in particular human hair
  • an agent (b) to the keratin material, the agent (b) containing at least one coloring compound from the group of pigments and / or substantive dyes, and
  • agent (c) on the keratin material, the agent (c) containing:
  • the three means (a), (b) and (c) being different from one another.
  • the agent (a) is characterized by its content of at least one organic silicon compound, in particular at least one organic silane.
  • the organic silicon compounds or organic silanes contained in the agent (a) are reactive compounds.
  • the agent (a) contains the organic silicon compound (s), in particular the organic silane or silanes, in a cosmetic carrier, which can be water-containing, low in water or else anhydrous.
  • the cosmetic carrier can be liquid, gel-like, creamy, pasty, powdery or solid (e.g. in the form of a tablet or a pellet).
  • the cosmetic carrier of the agent (a) is preferably an aqueous or aqueous-alcoholic carrier.
  • such carriers are, for example, creams, emulsions, gels or surfactant-containing foaming solutions such as shampoos, foam aerosols, foam formulations or other preparations which are suitable for use on the hair.
  • the cosmetic carrier is preferably water-containing, which means that the carrier - based on its weight - contains at least 2% by weight of water.
  • the water content is preferably above 5% by weight, more preferably above 10% by weight, even more preferably above 15% by weight.
  • the cosmetic carrier can also be aqueous-alcoholic.
  • aqueous-alcoholic solutions are to be understood as meaning aqueous solutions containing 2 to 70% by weight of a C 1 -C 4 alcohol, in particular ethanol or isopropanol.
  • the agents can additionally contain other organic solvents, such as methoxybutanol, benzyl alcohol, ethyl diglycol or 1,2-propylene glycol. All water-soluble organic solvents are preferred.
  • the aforementioned coloring compounds are deposited in a particularly homogeneous and smooth film on the surface of the keratinous material or diffuse into the keratinous fiber.
  • the film is formed in situ by oligomerization or polymerization of the organic
  • Silicon compounds as well as the interaction of organic silicon compounds with the coloring compounds.
  • the agent (a) contains at least one organic radical
  • Silicon compound Preferred organic silicon compounds are selected from silanes having one, two or three silicon atoms.
  • Organic silicon compounds which are alternatively referred to as organosilicon compounds, are compounds that either have a direct silicon-carbon bond (Si-C) or in which the carbon is attached to the silicon via an oxygen, nitrogen or sulfur atom. Atom is linked.
  • the organic silicon compounds of the present invention are preferred Compounds containing one to three silicon atoms.
  • the organic silicon compounds particularly preferably contain one or two silicon atoms.
  • the agent (a) particularly preferably contains at least one organic silicon compound selected from silanes having one, two or three silicon atoms.
  • silane stands for a group of chemical compounds based on a silicon backbone and hydrogen.
  • the hydrogen atoms have been completely or partially replaced by organic groups such as (substituted) alkyl groups and / or alkoxy groups.
  • organic silanes some of the hydrogen atoms can also be replaced by hydroxyl groups.
  • the method is characterized by the use of an agent (a) on the keratinous material, the agent (a) containing at least one organic silicon compound selected from silanes having one, two or three silicon atoms.
  • the agent (a) particularly preferably contains at least one organic silicon compound which is selected from silanes having one, two or three silicon atoms, the organic
  • Silicon compound also comprises one or more basic chemical functions and one or more hydroxyl groups or hydrolyzable groups per molecule.
  • the method is characterized by the use of an agent (a) on the keratinous material, the agent (a) containing at least one organic silicon compound selected from silanes having one, two or three silicon atoms, wherein the organic silicon compound further comprises one or more basic chemical functions and one or more hydroxyl groups or hydrolyzable groups per molecule.
  • This basic group can be, for example, an amino group, a
  • Alkylamino group or a dialkylamino group which is preferably connected to a silicon atom via a linker.
  • the basic group is preferably an amino group, a Ci-C6-alkylamino group or a di (Ci-C6) alkylamino group.
  • the hydrolyzable group (s) is preferably a Ci-C6-alkoxy group, in particular an ethoxy group or a methoxy group. It is preferred if the hydrolyzable group is bonded directly to the silicon atom. If, for example, the hydrolyzable group is an ethoxy group, the organic silicon compound preferably contains a structural unit R'R "R"'Si-O-CH 2 -CH3. The radicals R ', R "and R"' represent the three remaining free valences of the silicon atom.
  • a particularly preferred method is characterized in that the agent (a) contains at least one organic silicon compound selected from silanes with one, two or three silicon atoms, the organic silicon compound preferably having one or more basic chemical functions and one or more hydroxyl groups or comprises hydrolyzable groups per molecule.
  • agent (a) contains at least one organic silicon compound of the formula (I) and / or (II).
  • a method is characterized in that an agent (a) is used on the keratinic material or the human hair, the agent (a) at least one organic silicon compound (a) of the formula (I) and / or (II) contains,
  • R2 independently represent a hydrogen atom or a Ci-C6-alkyl group
  • - L stands for a linear or branched, divalent Ci-C2o-alkylene group
  • R3 stands for a hydrogen atom or a Ci-C6-alkyl group
  • R5 ‘, R5“ independently of one another represent a hydrogen atom or a C1-C6 alkyl group
  • R6 ‘and R6“ independently represent a Ci-C6-alkyl group
  • a ‘, A”, A “‘ and A ““ independently of one another represent a linear or branched, divalent Ci-C2o-alkylene group
  • Ci-C6-alkyl group examples are the groups methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl and t-butyl, n-pentyl and n-hexyl. Propyl, ethyl and methyl are preferred alkyl radicals.
  • Examples of a C2-C6-alkenyl group are vinyl, allyl, but-2-enyl, but-3-enyl and isobutenyl, preferred C2-C6-alkenyl radicals are vinyl and allyl.
  • a hydroxy-Ci-C6-alkyl group are a hydroxymethyl, a 2-hydroxyethyl, a 2-hydroxypropyl, a 3-hydroxypropyl, a 4-hydroxybutyl group, a 5-hydroxypentyl and a 6-hydroxyhexyl group; a 2-hydroxyethyl group is particularly preferred.
  • Examples of an amino-Ci-C6-alkyl group are the aminomethyl group, the 2-aminoethyl group and the 3-aminopropyl group. The 2-aminoethyl group is particularly preferred.
  • Examples of a linear divalent Ci-C2o-alkylene group are, for example, the methylene group (-CH2-), the ethylene group (-CH2-CH2-), the propylene group (-CH2-CH2-CH2-) and the butylene group (-CH2- CH2-CH2-CH2-).
  • the propylene group (-CH2-CH2-CH2-) is particularly preferred.
  • divalent alkylene groups can also be branched. Examples of branched, divalent C3-C2o-alkylene groups are (-CH2-CH (CH3) -) and (-CH2-CH (CH 3 ) -CH 2 -).
  • Ri R2N-L-Si OR3) a (R4) b (l)
  • the radicals Ri and R2 independently of one another represent a hydrogen atom or a C1-C6-alkyl group.
  • the radicals Ri and R2 are very particularly preferably both a hydrogen atom.
  • the organic silicon compound In the middle part of the organic silicon compound is the structural unit or the linker -L- which stands for a linear or branched, divalent Ci-C2o-alkylene group.
  • -L- is preferably a linear, divalent Ci-C2o-alkylene group. More preferably -L- stands for a linear divalent Ci-C6-alkylene group. -L- is particularly preferably a methylene group (-CH2-), an ethylene group (-CH2-CH2-), a propylene group (-CH2-CH2-CH2-) or a
  • L very particularly preferably represents a propylene group (- CH2-CH2-CH2-).
  • the radical R3 stands for a hydrogen atom or a Ci-C6-alkyl group
  • the radical R4 stands for a Ci-C6-alkyl group.
  • R3 and R4 are particularly preferably, independently of one another, a methyl group or an ethyl group.
  • a stands for an integer from 1 to 3, and b stands for the integer 3 - a. If a is 3, then b is 0. If a is 2, then b is 1. If a is 1, then b is 2.
  • the agent (a) contains at least one organic silicon compound of the formula (I) in which the radicals R3, R4 independently of one another represent a methyl group or an ethyl group.
  • the agent (a) contains at least one organic silicon compound of the formula (I) in which the radical a stands for the number 3. In this case, the remainder b stands for the number 0.
  • an agent (a) is characterized in that it contains at least one organic silicon compound of the formula (I),
  • R 3 independently of one another represent a methyl group or an ethyl group
  • the method is characterized in that the agent (a) contains at least one organic silicon compound of the formula (I),
  • R2 both stand for a hydrogen atom
  • - L stands for a linear, divalent Ci-C6-alkylene group, preferably for a propylene group (-CH2- CH2-CH2-) or for an ethylene group (-CH2-CH2-),
  • R3 represents a hydrogen atom, an ethyl group or a methyl group
  • R4 stands for a methyl group or for an ethyl group
  • the method is accordingly characterized in that the agent (a) contains at least one organic silicon compound of the formula (I),
  • R2 both stand for a hydrogen atom
  • Ci-C6 alkylene group preferably for a propylene group (-CH2-
  • R3 represents a hydrogen atom, an ethyl group or a methyl group
  • the process is characterized in that the agent (a) contains at least one organic silicon compound of the formula (I) which is selected from the group from
  • (3-Aminopropyl) trimethoxysilane can be purchased from Sigma-Aldrich, for example. (3-Aminopropyl) triethoxysilane is also commercially available from Sigma-Aldrich.
  • the agent (a) contains at least one organic silicon compound of the formula (II)
  • organosilicon compounds of the formula (II) each have the silicon-containing groups (RsO) c (R6) dSi- and -Si (R6 ') d' (OR5 ') c at both ends
  • each of the radicals e, f, g and h can independently represent the number 0 or 1, with the proviso that at least one of the radicals e, f, g and h is different from 0.
  • Silicon compound of the formula (II) at least one group from the group consisting of - (A) - and - [NR7- (A ') j- and - [0- (A ”) j- and - [NR 8 - (A”' )] -
  • radicals R5, R5', R5 "independently of one another represent a hydrogen atom or a Ci-C6- Alkyl group.
  • the radicals R6, R6 'and R6 ′′ stand independently of one another for a Ci-C6-alkyl group.
  • c stands for an integer from 1 to 3, and d stands for the integer 3 - c. If c is 3, then d is 0. If c is 2, d is 1. If c is 1, d is 2.
  • d‘ stands for the integer 3 - c ‘. If c ‘stands for the number 3, then d‘ equals 0. If c ‘stands for the number 2, then d‘ equals 1. If c ‘stands for the number 1, then d‘ equals 2.
  • the method is characterized in that the agent (a) contains at least one organic silicon compound of the formula (II),
  • R5 and R5 ‘independently represent a methyl group or an ethyl group
  • the radicals e, f, g and h can independently represent the number 0 or 1, at least one radical from e, f, g and h being different from zero.
  • the abbreviations e, f, g and h are used to define which of the groupings - (A) e - and - [NR7- (A ')] f and - [0- (A ”)] g - and - [NR8 - (A ”')] h - are located in the central part of the organic silicon compound of the formula (II).
  • the radicals A, A ‘, A”, A “‘ and A ““ stand independently of one another for a linear or branched, divalent Ci-C2o-alkylene group.
  • the radicals A, A ‘, A ′′, A ′′ and A ′′ ′′ are preferably, independently of one another, a linear, divalent Ci-C20-alkylene group.
  • the radicals A, A ‘, A ′′, A ′′ A and A ′′ ′′ are more preferably, independently of one another, a linear divalent Ci-C6-alkylene group.
  • the radicals A, A ', A “, A”' and A “” are particularly preferably, independently of one another, a methylene group (-CH2-), an ethylene group (-CH2-CH2-), a propylene group (-CH2-CH2-CH2) -) or a butylene group (-CH2-CH2-CH2-).
  • the radicals A, A ‘, A ′′, A ′′ and A ′′ ′′ are very particularly preferably a propylene group (-CH2-CH2-CH2-).
  • Silicon compound of formula (II) has a structural grouping - [NR7- (A ’)] -.
  • Silicon compound of formula (II) has a structural grouping - [NR8- (A ”’)] -.
  • radicals R7 and Rs independently of one another represent a hydrogen atom, a Ci-Ce-alkyl group, a hydroxy-Ci-C6-alkyl group, a C2-C6-alkenyl group, an amino-Ci-C6-alkyl group or a grouping of the Formula (III)
  • the radicals R7 and Rs are very particularly preferably, independently of one another, a hydrogen atom, a methyl group, a 2-hydroxyethyl group, a 2-alkenyl group, a 2-aminoethyl group or a grouping of the formula (III).
  • the organic silicon compound according to the invention contains the grouping [NR7- (A ')], but not the grouping - [NR8- (A ”')] now the radical R7 represents a grouping of the formula (III), then the agent (a) contains an organic silicon compound with 3 reactive silane groups.
  • the method is characterized in that the agent (a) contains at least one organic silicon compound of the formula (II),
  • R7 represents a hydrogen atom, a methyl group, a 2-hydroxyethyl group, a 2-alkenyl group, a 2-aminoethyl group or a grouping of the formula (III).
  • the process is characterized in that the agent (a) contains at least one organic silicon compound of the formula (II), where
  • - A and A ‘independently of one another represent a methylene group (-CH2-), an ethylene group (-CH2-CH2-) or a propylene group (-CH2-CH2-CH2), and
  • R7 represents a hydrogen atom, a methyl group, a 2-hydroxyethyl group, a 2-alkenyl group, a 2-aminoethyl group or a grouping of the formula (III).
  • organic silicon compounds of the formula (II) are commercially available.
  • Bis (trimethoxysilylpropyl) amine with the CAS number 82985-35-1 can be purchased from Sigma-Aldrich, for example.
  • Bis [3- (triethoxysilyl) propyl] amine with the CAS number 13497-18-2 can be purchased from Sigma-Aldrich, for example.
  • N-methyl-3- (trimethoxysilyl) -N- [3- (trimethoxysilyl) propyl] -1-propanamine is alternatively referred to as bis (3-trimethoxysilylpropyl) -N-methylamine and can be purchased commercially from Sigma-Aldrich or Fluorochem .
  • an agent (a) is characterized in that it contains at least one organic silicon compound of the formula (II) which is selected from the group consisting of
  • the agent (a) applied to the keratinous material in the process contains at least one organic silicon compound of the formula (IV)
  • organic silicon compound (s) of the formula (IV) can also be referred to as silanes of the alkylalkoxysilane or alkylhydroxysilane type,
  • Rg stands for a Ci-Ci8-alkyl group
  • - Rio stands for a hydrogen atom or a Ci-C6-alkyl group
  • - R11 stands for a Ci-C6-alkyl group
  • the process is characterized in that the agent (a) contains at least one organic silicon compound of the formula (IV).
  • Rg stands for a Ci-Ci8-alkyl group
  • - Rio stands for a hydrogen atom or a Ci-C6-alkyl group
  • the process is characterized in that the agent (a) contains at least one further organic silicon compound of the formula (IV) in addition to the organic silicon compound or compounds of the formula (I)
  • Rg stands for a Ci-Ci8-alkyl group
  • - Rio stands for a hydrogen atom or a Ci-C6-alkyl group
  • the process is characterized in that the agent (a) contains at least one further organic silicon compound of the formula (IV) in addition to the organic silicon compound or compounds of the formula (II)
  • Rg stands for a Ci-Ci8-alkyl group
  • - Rio stands for a hydrogen atom or a Ci-C6-alkyl group
  • the process is characterized in that the agent (a) contains at least one further organic silicon compound of the formula (IV) in addition to the organic silicon compound or compounds of the formula (I) and / or (II)
  • Rg stands for a Ci-Ci8-alkyl group
  • - Rio stands for a hydrogen atom or a Ci-C6-alkyl group
  • the radical Rg stands for a C1-C18-alkyl group.
  • This Ci-Ci8-alkyl group is saturated and can be linear or branched.
  • Rg is preferably a linear Ci-Ci8-alkyl group.
  • Rg is preferably a methyl group, a
  • Rg particularly preferably represents a methyl group, an ethyl group, an n-hexyl group or an n-octyl group.
  • the radical R10 represents a hydrogen atom or a Ci-C6-alkyl group.
  • R10 particularly preferably represents a methyl group or an ethyl group.
  • the radical Rn stands for a Ci-C6-alkyl group.
  • R11 particularly preferably represents a methyl group or an ethyl group.
  • k stands for an integer from 1 to 3, and m stands for the integer 3 - k. If k is the number 3, then m is 0. If k is the number 2, then m is 1. If k is the number 1, then m is 2.
  • the process is characterized in that the agent (a) contains at least one organic silicon compound of the formula (IV) which is selected from the group from
  • the method is characterized in that an agent (a) is used on the keratinic material which contains at least one organic silicon compound of the formula (I) which is selected from the group consisting of (3-aminopropyl) triethoxysilane and (3-aminopropyl) trimethoxysilane is selected, and additionally contains at least one organic silicon compound of the formula (IV), which is selected from the group consisting of methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane,
  • Ethyltriethoxysilane, hexyltrimethoxysilane and hexyltriethoxysilane is selected.
  • the organic silicon compounds described above are reactive compounds. In this context, it has been found to be preferred if the agent (a) - based on the total weight of the agent (a) - has one or more organic
  • the agent (a) - based on the total weight of the agent (a) - is one or more organic Contains silicon compounds of the formula (I) and / or (II) in a total amount of 0.1 to 20% by weight, preferably 0.2 to 15% by weight and particularly preferably 0.2 to 3% by weight.
  • the agent (a) - based on the total weight of the agent (a) - has one or more organic silicon compounds of the formula (IV) in a total amount of 0.1 to 20% by weight, preferably 0.5 to 15% by weight and particularly preferably 2 to 8% by weight.
  • the organosilicon compound can also be present in the agent (a) in the form of condensation products and / or (partial) hydrolysates of the organosilicon compounds.
  • Condensation products can include, for example, the condensation products of two, three or four organosilicon compounds.
  • the agent (a) preferably contains water and has a pH of from 7 to 11.5, preferably from 7.5 to 11 and particularly preferably from 8 to 10.5.
  • the method is characterized in that the agent (a) has a pH of 7 to 11.5, preferably from 7.5 to 11 and particularly preferably from 8 to 10.5.
  • the agent (b) is characterized by the presence of at least one coloring compound from the group of pigments and / or substantive dyes.
  • the agent (b) can also be referred to as coloring agent (b).
  • Pigments in the context of the present invention are understood to mean coloring compounds which at 25 ° C. in water have a solubility of less than 0.5 g / L, preferably less than 0.1 g / L, even more preferably less than 0, 05 g / L.
  • the water solubility can be achieved, for example, using the method described below: Weigh out 0.5 g of the pigment in a beaker. A stir fry is added. Then one liter of distilled water is added. This mixture is heated to 25 ° C. for one hour while stirring on a magnetic stirrer. Are still undissolved in the mixture after this period
  • the solubility of the pigment is below 0.5 g / L. If the pigment-water mixture cannot be assessed visually due to the high intensity of the pigment which may be present in finely dispersed form, the mixture is filtered. If a proportion of undissolved pigments remains on the filter paper, the solubility of the pigment is below 0.5 g / L.
  • Suitable color pigments can be of inorganic and / or organic origin.
  • agent (b) is characterized in that it contains at least one coloring compound from the group of inorganic and / or organic pigments.
  • Preferred color pigments are selected from synthetic or natural inorganic pigments.
  • Inorganic color pigments of natural origin can be made from chalk, ocher, umber, green earth, burnt Terra di Siena or graphite, for example.
  • black pigments such as B. iron oxide black, colored pigments such.
  • B. ultramarine or iron oxide red and fluorescent or phosphorescent pigments can be used.
  • Colored metal oxides, hydroxides and oxide hydrates, mixed-phase pigments, sulfur-containing silicates, silicates, metal sulfides, complex metal cyanides, metal sulfates, metal chromates and / or molybdates are particularly suitable.
  • Particularly preferred color pigments are black iron oxide (CI 77499), yellow iron oxide (CI 77492), red and brown iron oxide (CI 77491), manganese violet (CI 77742), ultramarines (sodium aluminum sulfosilicates, CI 77007, Pigment Blue 29), chromium oxide hydrate
  • Colored pigments which are also particularly preferred are colored pearlescent pigments. These are usually based on mica and / or mica and can be coated with one or more metal oxides. Mica is one of the layered silicates. The most important representatives of these silicates are muscovite, phlogopite, paragonite, biotite, lepidolite and margarite. To manufacture the
  • Pearlescent pigments in connection with metal oxides the mica, predominantly muscovite or phlogopite, is coated with a metal oxide.
  • synthetic mica coated with one or more metal oxide (s) can also be used as a pearlescent pigment.
  • Particularly preferred pearlescent pigments are based on natural or synthetic mica (mica) and are coated with one or more of the aforementioned metal oxides. The color of the respective pigments can be varied by varying the layer thickness of the metal oxide (s).
  • the method is characterized in that the agent (b) contains at least one coloring compound from the group of pigments, which is selected from the group of colored metal oxides, metal hydroxides, metal oxide hydrates, silicates, metal sulfides, complex metal cyanides, metal sulfates , Bronze pigments and / or of colored pigments based on mica or mica, which are coated with at least one metal oxide and / or a metal oxychloride.
  • the agent (b) contains at least one coloring compound from the group of pigments, which is selected from the group of colored metal oxides, metal hydroxides, metal oxide hydrates, silicates, metal sulfides, complex metal cyanides, metal sulfates , Bronze pigments and / or of colored pigments based on mica or mica, which are coated with at least one metal oxide and / or a metal oxychloride.
  • the agent (b) is characterized in that it contains at least one coloring compound from the group of pigments, which is selected from pigments based on mica or mica, which with one or more metal oxides from the Group of titanium dioxide (CI 77891), black iron oxide (CI 77499), yellow iron oxide (CI 77492), red and / or brown iron oxide (CI 77491, CI 77499), manganese violet (CI 77742), ultramarines (sodium aluminum sulfosilicates, CI 77007 , Pigment Blue 29), chromium oxide hydrate (CI 77289),
  • the group of pigments which is selected from pigments based on mica or mica, which with one or more metal oxides from the Group of titanium dioxide (CI 77891), black iron oxide (CI 77499), yellow iron oxide (CI 77492), red and / or brown iron oxide (CI 77491, CI 77499), manganese violet (CI 77742), ultramarines (sodium aluminum sulfos
  • Chromium oxide (CI 77288) and / or iron blue (Ferric Ferrocyanide, CI 77510) are coated.
  • Color pigments with the trade name Xirona® are also particularly preferred
  • the agent (b) can also contain one or more coloring compounds from the group of organic pigments.
  • the organic pigments are correspondingly insoluble, organic dyes or color lakes, for example from the group of nitroso, nitro, azo, xanthene, anthraquinone, isoindolinone, isoindoline, quinacridone, perinone, perylene , Diketopyrrolopyorrol-, indigo, thioindido, dioxazine, and / or triarylmethane compounds can be selected.
  • Particularly suitable organic pigments are, for example, carmine, quinacridone, phthalocyanine, sorghum, blue pigments with the color index numbers CI 42090, CI 69800, CI 69825, CI 73000, CI 74100, CI 74160, yellow pigments with the color index numbers CI 11680 , CI 11710, CI 15985, CI 19140, CI 20040, CI 21100, CI 21108, CI 47000, CI 47005, green pigments with the color index numbers CI 61565, CI 61570, CI 74260, orange pigments with the color index numbers CI 11725 , CI 15510, CI 45370, CI 71105, red pigments with the color index numbers CI 12085, CI 12120, CI 12370, CI 12420, CI 12490, CI 14700, CI 15525, CI 15580, CI 15620, CI 15630, CI 15800
  • the method is characterized in that the agent (b) contains at least one coloring compound from the group of organic pigments, which is selected from the group consisting of carmine, quinacridone, Phthalocyanine, Sorgho, blue pigments with the color index numbers CI 42090, CI 69800, CI 69825, CI 73000, CI 74100, CI 74160, yellow pigments with the color index numbers CI 1 1680, CI 1 1710, CI 15985, CI 19140, CI 20040, CI 21 100, CI 21 108, CI 47000, CI 47005, green pigments with the color index numbers CI 61565, CI 61570, CI 74260, orange pigments with the color index numbers CI 1 1725, CI 15510, CI 45370, CI 71 105, red pigments with the color index numbers CI 12085, CI 12120, CI 12370, CI 12420, CI 12490,
  • the agent (b)
  • the organic pigment can also be a colored lacquer.
  • colored varnish is understood to mean particles which comprise a layer of absorbed dyes, the unit of particles and dyestuff falling under the above
  • the particles can be, for example, inorganic substrates, which can be aluminum, silica, calcium borosilicate, calcium aluminum borosilicate or also aluminum.
  • the alizarin color varnish for example, can be used as the color varnish.
  • the use of the aforementioned pigments in means (b) of the process is very particularly preferred. It is also preferred if the pigments used have a certain particle size. It is advantageous according to the invention if the at least one pigment has an average particle size D 50 of 1 to 50 ⁇ m, preferably 5 to 45 ⁇ m, more preferably 10 to 40 ⁇ m, in particular 14 to 30 ⁇ m.
  • the mean particle size Dso can be determined, for example, using dynamic light scattering (DLS).
  • the pigment or pigments can be used in an amount of from 0.001 to 20% by weight, in particular from 0.05 to 5% by weight, based in each case on the total weight of the agent (b).
  • the agents (b) used in the process can also contain one or more substantive dyes as coloring compounds.
  • Direct dyes are dyes that are absorbed directly onto the hair and do not require an oxidative process to develop the color.
  • Substantive dyes are usually nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones, triarylmethane dyes or indophenols.
  • the substantive dyes for the purposes of the present invention have a solubility in water (760 mmHg) at 25 ° C. of more than 0.5 g / L and are therefore not to be regarded as pigments.
  • the substantive dyes for the purposes of the present invention preferably have a
  • Substantive dyes can be divided into anionic, cationic and nonionic substantive dyes.
  • an agent (b) is characterized in that it contains at least one anionic, cationic and / or nonionic substantive dye as the coloring compound.
  • an agent (b) is characterized in that it contains at least one anionic, cationic and / or nonionic substantive dye.
  • Suitable cationic substantive dyes are, for example, Basic Blue 7, Basic Blue 26, Basic Violet 2 and Basic Violet 14, Basic Yellow 57, Basic Red 76, Basic Blue 16, Basic Blue 347 (Cationic Blue 347 / Dystar), HC Blue No. 16, Basic Blue 99, Basic Brown 16, Basic Brown 17, Basic Yellow 57, Basic Yellow 87, Basic Orange 31, Basic Red 51, and / or Basic Red 76
  • nonionic substantive dyes for example, nonionic nitro and
  • Direct dyes are those under the international names or trade names HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, HC Yellow 12, HC Orange 1, Disperse Orange 3, HC Red 1, HC Red 3, HC Red 10 , HC Red 11, HC Red 13, HC Red BN, HC Blue 2, HC Blue 11, HC Blue 12, Disperse Blue 3, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Disperse Black 9 known compounds, as well as 1, 4-diamino-2-nitrobenzene, 2-amino-4-nitrophenol, 1,4-bis- (2-hydroxyethyl) -amino-2-nitrobenzene, 3-nitro-4- (2-hydroxyethyl) -aminophenol, 2- (2-hydroxyethyl) amino-4,6-dinitrophenol, 4 - [(2-hydroxyethyl) amino] -3-nitro-1-methylbenzene, 1-amino-4- (2-hydroxyethyl) -amino-5-chloro- 2-nitrobenzene, 4-
  • the method is characterized in that the agent (b) contains at least one substantive dye which is selected from the group of anionic, cationic and nonionic substantive dyes.
  • agents (b) which contain at least one anionic substantive dye dyeings with particularly high color intensity can be produced.
  • an agent (b) used in the process is therefore characterized in that it contains at least one anionic substantive dye.
  • Anionic substantive dyes are also referred to as acid dyes.
  • Acid dyes are understood to be substantive dyes which contain at least one
  • Carboxylic acid grouping (-COOH) and / or a sulfonic acid grouping (-SO3H).
  • the protonated forms (-COOH, -SO3H) of the carboxylic acid or sulfonic acid groups are in equilibrium with their deprotonated forms (-COO-, -SO3 ⁇ before).
  • the proportion of protonated forms increases with decreasing pH. If substantive dyes are used in the form of their salts, the carboxylic acid groups or
  • Sulphonic acid groups are present in deprotonated form and are neutralized with corresponding stoichiometric equivalents of cations in order to maintain electroneutrality.
  • Acid dyes according to the invention can also be used in the form of their sodium salts and / or their potassium salts.
  • the acid dyes for the purposes of the present invention have a solubility in water (760 mmHg) at 25 ° C. of more than 0.5 g / L and are therefore not to be regarded as pigments.
  • the acid dyes preferably have a solubility in water (760 mmHg) at 25 ° C. of more than 1.0 g / l.
  • alkaline earth salts such as calcium salts and magnesium salts
  • aluminum salts of acid dyes often have a poorer solubility than the corresponding alkali salts. If the solubility of these salts is below 0.5 g / L (25 ° C, 760 mmHg), they do not fall under the definition of a substantive dye.
  • An essential feature of the acid dyes is their ability to form anionic charges, the carboxylic acid or sulfonic acid groups responsible for this usually being linked to different chromophoric systems.
  • Suitable chromophoric systems can be found for example in the structures of nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinone dyes, triarylmethane dyes, xanthene dyes, rhodamine dyes, oxazine dyes and / or indophenol dyes.
  • an agent (b) which is characterized in that it contains at least one anionic substantive dye selected from the group of nitrophenylenediamines, the
  • Nitroaminophenols the azo dyes, the anthraquinone dyes, the triarylmethane dyes, the xanthene dyes, the rhodamine dyes, the oxazine dyes and / or the
  • Indophenol dyes the dyes from the aforementioned group each having at least one carboxylic acid group (-COOH), a sodium carboxylate group (-COONa), a potassium carboxylate group (-COOK), a sulfonic acid group (-SO3H), a sodium sulfonate group (-SOsNa) and / or a potassium sulfonate group ( -SO3K).
  • One or more compounds from the following group can be selected as particularly suitable acid dyes: Acid Yellow 1 (D&C Yellow 7, Citronin A, Ext. D&C Yellow No.
  • Acid Yellow 36 (CI 13065), Acid Yellow 121 (CI 18690), Acid Orange 6 (CI 14270), Acid Orange 7 (2-Naphthol orange, Orange II, CI 15510, D&C Orange 4, COLIPA n ° C015), Acid Orange 10 (Cl 16230; Orange G sodium salt), Acid Orange 11 (CI 45370), Acid Orange 15 (CI 50120), Acid Orange 20 (CI 14600), Acid Orange 24 (BROWN 1; CI 20170; KATSU201; nosodiumsalt; Brown No.201; RESORCIN BROWN; ACID
  • Acid Green 50 (Brillantklare indispensable BS, Cl 44090, Acid Brilliant Green BS, E 142), Acid Black 1 (Black n ° 401, Naphthalene Black 10B, Amido Black 10B, CI 20 470, COLIPA n ° B15), Acid Black 52 (CI 15711), Food Yellow 8 (CI 14270), Food Blue 5, D&C Yellow 8, D&C Green 5, D&C Orange 10, D&C Orange 11, D&C Red 21, D&C Red 27, D&C Red 33, D&C Violet 2 and / or D&C Brown 1.
  • the water solubility of the substantive dyes can be determined, for example, in the following way. 0.1 g of the substantive dye are placed in a beaker. A stir bar is added. Then 100 ml of water are added. This mixture is heated to 25 ° C. on a magnetic stirrer while stirring. It is stirred for 60 minutes. The aqueous mixture is then assessed visually. If there are still undissolved residues, the amount of water is increased - for example in steps of 10 ml. Water is added until the amount of dye used has completely dissolved. If the dye-water mixture cannot be assessed visually due to the high intensity of the dye, the mixture is filtered. If a portion of undissolved dyes remains on the filter paper, the solubility test is repeated with a larger amount of water.
  • Acid Yellow 1 is called 8-hydroxy-5,7-dinitro-2-naphthalenesulfonic acid disodium salt and has a solubility in water of at least 40 g / L (25 ° C).
  • Acid Yellow 3 is a mixture of the sodium salts of mono- and disulfonic acids of 2- (2-quinolyl) -1 H-indene-1, 3 (2H) -dione and has a water solubility of 20 g / L (25 ° C).
  • Acid Yellow 9 is the disodium salt of 8-hydroxy-5,7-dinitro-2-naphthalenesulfonic acid, its water solubility is above 40 g / L (25 ° C).
  • Acid Yellow 23 is the trisodium salt of 4,5-dihydro-5-oxo-1 - (4-sulfophenyl) -4 - ((4-sulfophenyl) azo) - 1 H-pyrazole-3-carboxylic acid and at 25 ° C well in Water soluble.
  • Acid Orange 7 is the sodium salt of 4 - [(2-Hydroxy-1-naphthyl) azo] benzene sulfonate. His
  • Water solubility is more than 7 g / L (25 ° C).
  • Acid Red 18 is the trisodium salt of 7-hydroxy-8 - [(E) - (4-sulfonato-1-naphthyl) -diazenyl)] - 1,3-naphthalenedisulfonate and has a very high solubility in water of more than 20 wt. -%.
  • Acid Red 33 is the disodium salt of 5-amino-4-hydroxy-3- (phenylazo) -naphthalene-2,7-disulphonate, its water solubility is 2.5 g / L (25 ° C).
  • Acid Red 92 is the disodium salt of 3,4,5,6-tetrachloro-2- (1,4,5,8-tetrabromo-6-hydroxy-3-oxoxanthen-9-yl) benzoic acid, its water solubility is specified with greater than 10 g / L (25 ° C).
  • Acid Blue 9 is the disodium salt of 2 - ( ⁇ 4- [N-ethyl (3-sulfonatobenzyl] amino] phenyl ⁇ ⁇ 4 - [(N-ethyl (3-sulfonatobenzyl) imino] -2,5-cyclohexadiene-1 - ylidene ⁇ methyl) benzene sulfonate and has a water solubility of more than 20% by weight (25 ° C).
  • a very particularly preferred method is characterized in that the agent (b) has at least one anionic substantive dye from the group consisting of acid yellow
  • Acid Yellow 3 Acid Yellow 9, Acid Yellow 17, Acid Yellow 23, Acid Yellow 36, Acid Yellow 121, Acid Orange 6, Acid Orange 7, Acid Orange 10, Acid Orange 1 1, Acid Orange 15, Acid Orange 20 , Acid Orange 24, Acid Red 14, Acid Red, Acid Red 27, Acid Red 33, Acid Red 35, Acid Red 51, Acid Red 52, Acid Red 73, Acid Red 87, Acid Red 92, Acid Red 95, Acid Red 184, Acid Red 195, Acid Violet 43, Acid Violet 49, Acid Violet 50, Acid Blue 1, Acid Blue 3, Acid Blue 7, Acid Blue 104, Acid Blue 9, Acid Blue 62, Acid Blue 74, Acid Blue 80, Acid Green 3, Acid Green 5, Acid Green 9, Acid Green 22, Acid Green 25, Acid Green 50, Acid Black 1, Acid Black 52, Food Yellow 8, Food Blue 5, D&C Yellow 8, D&C Green 5, D&C Orange 10, D&C Orange 1 1, D&C Red 21, D&C Red 27, D&C Red 33, D&C Violet
  • the substantive dye or dyes in particular the anionic substantive dyes, can be used in the agent (b) in various amounts, depending on the desired color intensity. Particularly good results could be obtained when the agent (b) - based on the total weight of the agent (b) - has one or more substantive dyes in a total amount of 0.01 to 10% by weight, preferably 0.1 to 8 % By weight, more preferably from 0.2 to 6% by weight and very particularly preferably from 0.5 to 4.5% by weight.
  • an agent (b) is characterized in that - based on the total weight of the agent (b) - it contains one or more substantive dyes in a total amount of 0.01 to 10% by weight, preferably of 0, 1 to 8% by weight, more preferably from 0.2 to 6% by weight and very particularly preferably from 0.5 to 4.5% by weight.
  • the agent (b) is characterized in that it - based on the total weight of the agent - one or more anionic substantive dyes in a total amount of 0.01 to 10 wt .-%, preferably from 0.1 to 8% by weight, more preferably from 0.2 to 6% by weight and very particularly preferably from 0.5 to 4.5% by weight.
  • agent (c) can be referred to as an aftertreatment agent.
  • Agent (c) is characterized by the presence of two selected silicones.
  • the silicone oils contained in the agent (c) comprise Si-O repeat units, it being possible for the Si atoms to carry organic radicals such as, for example, alkyl groups or substituted alkyl groups.
  • the silicones contained in the agent (c) are polymeric compounds whose molecular weight is at least 500 g / mol, preferably at least 1000 g / mol, more preferably at least 2500 g / mol, and particularly preferably at least 5000 g / mol.
  • the silicone oils contained in agent (c) are therefore different from the organic silicon compounds in agent (a).
  • the two silicones are each hydroxy-terminated, which means that each of the two silicones has at least one terminal OH group.
  • the subject of the application is a method for coloring keratinic material, in particular human hair, comprising the following steps:
  • an agent (a) to the keratinous material, the agent (a) containing at least one organic silicon compound having one, two or three silicon atoms,
  • an agent (b) on the keratinous material the agent (b) containing at least one coloring compound from the group of pigments and / or substantive dyes,
  • an agent (c) to the keratinic material, the agent (c) containing at least two polymeric silicones.
  • another subject matter of the application is a method for coloring keratinic material, in particular human hair, comprising the following steps:
  • an agent (a) to the keratinous material, the agent (a) containing at least one organic silicon compound having one, two or three silicon atoms,
  • an agent (b) on the keratinous material the agent (b) containing at least one coloring compound from the group of pigments and / or substantive dyes,
  • (c2) a reaction product of a hydroxy-terminated polyorganosiloxane with an acid and / or an alcohol and / or a wax.
  • a film of organosilicon compounds i.e. silanes
  • a layer of coloring compounds is now formed on the keratinous material, the coloring compounds being replaced by the organic
  • Silicon compound (s) of the agent (a) formed layer are fixed on the keratinic material. It has been found that the layers or films formed on the keratinous material are stabilized by the hydroxy-terminated polyorganosiloxanes contained in the agent (c). Without wishing to be bound by this theory, it is assumed that the hydroxy-terminated polyorganosiloxanes contained in the agent (c). Without wishing to be bound by this theory, it is assumed that the hydroxy-terminated
  • Polyorganosiloxanes form covalent bonds with the organic silicon compound (s) contained in the layer formed or their reaction products.
  • Suitable hydroxy-terminated polyorganosiloxanes are those with the INCI name
  • agent (c) is hydroxy-terminated
  • Polyorganosiloxane (c1) a polyorganosiloxane of the formula (I)
  • Xi and X2 are independently OH, OR 1 , R 2 , O-PDMS or O-fsiloxane, X3 is hydrogen or a monovalent hydrocarbon radical with 1 to 8 carbon atoms per radical, PDMS or fsiloxane,
  • X 4 is a radical of the formula
  • a is a number from 1 to 100
  • R 1 denotes an alkyl radical with 1 to 8 carbon atoms
  • R 2 denotes a monovalent, saturated or unsaturated hydrocarbon radical with 1 to 200 carbon atoms per radical, optionally substituted with the elements N, P, S, O, Si and halogen,
  • R 3 independently of one another, is in each case a monovalent, optionally substituted by the elements N, P, S, O, Si and halogen, saturated or unsaturated hydrocarbon radical with 1 to 200 carbon atoms per radical,
  • A is a radical of the formula R 6 - [NR 7 -R 8 -] fNR 7 2,
  • R 6 is a divalent linear or branched hydrocarbon radical with 3 to 18 carbon atoms
  • R 7 denotes a hydrogen atom, an alkyl group with 1 to 8 carbon atoms or an acyl group
  • R 8 denotes a divalent hydrocarbon group with 1 to 6 carbon atoms
  • b is a number from 1 to 2000
  • c is 0 or a number from 1 to 2000
  • d is a number from 1 to 1000
  • e is 0 or a number from 1 to 5
  • f 0, 1, 2, 3 or 4,
  • Z is hydrogen, an alkyl radical with 1 to 8 carbon atoms or means
  • R 4 denotes a monovalent hydrocarbon radical optionally containing N and / or O atoms and having 1 to 18 carbon atoms and
  • R 5 denotes a divalent hydrocarbon radical optionally containing N and / or O atoms and having 3 to 12 carbon atoms,
  • the polyorganosiloxane of the formula (I) has at least one terminal OH group.
  • Xi and X2 are independently OH, OR 1 , R 2 , O-PDMS or O-fsiloxane,
  • X3 is hydrogen or a monovalent hydrocarbon radical with 1 to 8 carbon atoms per radical, PDMS or fsiloxane,
  • X 4 is a radical of the formula
  • a is a number from 1 to 100
  • R 1 denotes an alkyl radical with 1 to 8 carbon atoms
  • R 2 denotes a monovalent, saturated or unsaturated hydrocarbon radical with 1 to 200 carbon atoms per radical, optionally substituted with the elements N, P, S, O, Si and halogen,
  • R 3 independently of one another, is in each case a monovalent, optionally substituted by the elements N, P, S, O, Si and halogen, saturated or unsaturated hydrocarbon radical with 1 to 200 carbon atoms per radical,
  • A is a radical of the formula R 6 - [NR 7 -R 8 -] fNR 7 2,
  • R 6 is a divalent linear or branched hydrocarbon radical with 3 to 18 carbon atoms
  • R 7 denotes a hydrogen atom, an alkyl group with 1 to 8 carbon atoms or an acyl group
  • R 8 denotes a divalent hydrocarbon group with 1 to 6 carbon atoms
  • b is a number from 1 to 2000
  • c is 0 or a number from 1 to 2000
  • d is a number from 1 to 1000
  • e is 0 or a number from 1 to 5
  • f 0, 1, 2, 3 or 4,
  • Z is hydrogen, an alkyl radical with 1 to 8 carbon atoms or
  • R 4 denotes a monovalent hydrocarbon radical optionally containing N and / or O atoms and having 1 to 18 carbon atoms and
  • R 5 denotes a divalent hydrocarbon radical optionally containing N and / or O atoms and having 3 to 12 carbon atoms,
  • the polyorganosiloxane of the formula (I) has at least one terminal OH group, contains as a hydroxy-terminated polyorganosiloxane.
  • Examples of an alkyl radical R 1 are methyl, ethyl, n-propyl, / so-propyl, 1-n-butyl, 2-n-butyl, iso-butyl, fe / f.-butyl , n-pentyl-, / so-pentyl-, neo-pentyl-, fe / f-pentyl, n-hexyl, n-heptyl, n-octyl, / so-octyl or 2,2,4-trimethylpentyl, methyl, ethyl and butyl are preferred.
  • hydrocarbon radicals R 2 and R 3 are alkyl radicals such as methyl, ethyl, n-propyl, iso-propyl, 1-n-butyl, 2-n-butyl, / so-butyl, fe / f.-butyl-, n-pentyl-, / so-pentyl-, neo-pentyl-, fe / f.-pentyl, n-hexyl, n-heptyl, n-octyl, / so-octyl, 2.2, 4-trimethylpentyl, n-nonyl, n-decyl, n-dodecyl, n-octadecyl, cyclopentyl, cyclohexyl, cycloheptyl, methylcyclohexyl, vinyl, 5-hexenyl,
  • the preferred radical R 2 is the methyl, ethyl, octyl and phenyl radical, and the methyl and ethyl radical are particularly preferred.
  • halogenated radicals R 2 and R 3 are 3,3,3-trifluoro-n-propyl, 2, 2, 2,2 ', 2', 2'-hexafluoroisopropyl, heptafluoroisopropyl, o-chlorophenyl, m-chlorophenyl and p-chlorophenyl radical.
  • R 4 are the alkyl, cycloalkyl, aryl, alkaryl and aralkyl radicals listed for the hydrocarbon radicals R 2 and R 3 .
  • R 5 are radicals of the formulas -CH2-CH2-O-CH2-CH2-, -CH2-CH2-NH-CH2-CH2- or -CH2-CH2-NH-CH2-, the radical -CH2-CH2 -O-CH2-CH2- is particularly preferred.
  • R 6 are alkylene radicals with 3 to 10 carbon atoms such as propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene and decylene.
  • R 7 can be a hydrogen atom, a methyl, ethyl, n-propyl, / so-propyl-, 1-n-butyl-, 2-n-butyl-, / so-butyl-, fe / f.-butyl -, n-pentyl-, / so-pentyl-, neo-pentyl-, fe / f-pentyl, n-hexyl, n-heptyl, n-octyl, / so-octyl, 2,2,4-trimethylpentyl- or acetyl radical, with a hydrogen atom being preferred.
  • R 8 are alkylene radicals such as methylene, ethylene, propylene, butylene, pentylene, or hexylene.
  • Z is preferably hydrogen or methyl, ethyl, n-propyl, / so-propyl, 1-n-butyl, 2-n-butyl, / so-butyl, fe / f.-butyl, n-pentyl-, / so-pentyl-, neo-pentyl-, fe / f-pentyl, n-hexyl, n-heptyl, n-octyl, / so-octyl or 2,2,4-trimethylpentyl-, where Hydrogen, methyl, ethyl and butyl are particularly preferred.
  • Preferred radicals X4 are, according to the above definitions for R 4 and R 5, aminomethyl, methylaminomethyl, dimethylaminomethyl, diethylaminomethyl, dibutylaminomethyl,
  • the cosmetic agent contains polyorganosiloxanes of the formula (I) which contain the morpholinomethyl radical as radical X4.
  • radical A is: - (CH 2 ) 3NH 2
  • Trialkoxysilane which is a radical formula
  • fSiloxane stands for a radical which is derived from an amine-functionalized siloxane.
  • Trialkoxysilanes or a mixture of dialkoxy and trialkoxysilanes are particularly preferably used, the use of trialkoxysilanes alone being particularly preferred.
  • trialkoxysilanes or a mixture of dialkoxy and trialkoxysilanes are used, at least partially crosslinked polyorganosiloxanes are obtained regardless of the structure of the siloxanes used and the position of the alkoxy and / or silanol groups in the siloxanes.
  • the cosmetic agent contains crosslinked polyorganosiloxanes.
  • the cosmetic agent contains crosslinked polyorganosiloxanes which have arisen from the reaction of siloxanes and trialkoxysilanes.
  • dialkoxy- or trialkoxysilanes used include: Diethylaminomethylmethyldimethoxysilane,
  • alkoxy radical is a Ci-C 4 alkoxy radical, in particular a mixture of methoxy and ethoxy radical
  • a particularly preferred silane is morpholinomethyltriethoxysilane.
  • a particularly preferred amine-functionalized siloxane is a copolymer of 3- (2-aminoethylamino) propylmethylsiloxy and dimethylsiloxy units which has silanol groups or alkoxy and silanol groups.
  • a cosmetic agent is particularly preferred in which as a hydroxy-terminated
  • Polyorganosiloxane at least one compound known under the INCI name Amodimethicone / Morpholinomethyl Silsesquioxane Copolymer is used.
  • This polyorganosiloxane is commercially available under the name Belsil® ADM 8301 E (ex Wacker).
  • the raw material is a microemulsion and has the following components: Amodimethicone / Morpholinomethyl Silsesquioxane Copolymer, Trideceth-5, Glycerin, Phenoxyethanol and Water.
  • the method is characterized in that the agent (c) is one of the INCI names
  • Amodimethicone / Morpholinomethyl Silsesquioxane Copolymer contains compound known as a hydroxy-terminated polyorganosiloxane (c1).
  • the agent (c) contains the hydroxy-terminated polyorganosiloxane (c1) in an amount from 0.1 to 10% by weight, preferably from 0.1 to 8% by weight, more preferably from 0.125 to 6% by weight , even more preferably 0.15 to 4% by weight and very particularly preferably from 0.2 to 2% by weight, based in each case on the weight of the cosmetic agent (c).
  • the agent (c) contains the reaction product of a hydroxy-terminated polyorganosiloxane with an acid and / or an alcohol and / or a wax.
  • the acid, alcohol or wax react with the terminal hydroxyl group (s) of polyorganosiloxane and form, for example, esters or ethers.
  • the method is characterized in that the agent (c) as a reaction product of a hydroxy-terminated polyorganosiloxane with an acid and / or an alcohol and / or a wax (c2) is a reaction product of a hydroxy-terminated Contains polyorganosiloxane with an acid, which is selected from the group consisting of reaction products of a hydroxy-terminated polyorganosiloxane with a fatty acid, reaction products of a hydroxy-terminated one
  • the agent (c) preferably contains the reaction product of a hydroxy-terminated polyorganosiloxane with a fatty acid as component (c2).
  • the method is characterized in that the agent (c) as a reaction product of a hydroxy-terminated polyorganosiloxane with an acid and / or an alcohol and / or a wax (c2) is a reaction product of a hydroxy- contains terminated polyorganosiloxane with a fatty acid.
  • fatty acids are aliphatic carboxylic acids which have unbranched or branched, optionally hydroxylated, hydrocarbon radicals with 4 to 40, preferably 8 to 24, carbon atoms.
  • the fatty acids used in the context of the present invention can be both naturally occurring and synthetically produced fatty acids.
  • the fatty acids can be mono- or polyunsaturated.
  • the fatty acid can also comprise a mixture of several fatty acids.
  • Particularly preferred fatty acids are selected from the group consisting of behenic acid, fatty acids obtained from the seed oil of borage (Borago officinalis L), fatty acids obtained from Vateria Indica, 12-hydroxystearic acid, isostearic acid, fatty acids obtained from the seed oil of American meadowfoam ("meadowfoam seed oil” J), fatty acids from mohwab butter, fatty acids obtained from sais butter, fatty acids obtained from cocum butter, fatty acids obtained from illipe butter,
  • Reaction products of a hydroxy-terminated polyorganosiloxane with a fatty acid include, for example, the reaction product of dimethiconol with behenic acid (INCI: dimethiconol behenate), the reaction product of dimethiconol with fatty acids obtained from borage seed oil (Borago officinalis L) (INCI: dimethiconol borageate), the
  • Reaction product of dimethiconol with fatty acids obtained from Vateria Indica (INCI: dimethiconol dhupa butterate), the reaction product of dimethiconol with 12-hydroxystearic acid (INCI: dimethiconol hydroxystearate), the reaction product of dimethiconol with isostearic acid (INCI: dimethiconol isostearate), the reaction product of dimethiconol with fatty acids obtained from the seed oil of American meadowfoam seed oil (INCI: dimethiconol meadowfoamate), the reaction product of dimethiconol with fatty acids from mohwa butterate (INCI: dimethiconol mohwa butterate), the reaction product of dimethiconol with fatty acids , which are obtained from ointment butter (INCI: dimethiconol sal butterate), the
  • Reaction product of dimethiconol with fatty acids obtained from cocum butter (INCI: dimethiconol kokum butterate)
  • the reaction product of dimethiconol with fatty acids obtained from illipe butter (INCI: dimethiconol illipe butterate)
  • the reaction product of dimethiconol with stearic acid (INCI: dimethiconol stearate).
  • the fatty acid is very particularly preferably selected from the group consisting of fatty acids obtained from the seed oil of American foam herb (“meadowfoam seed oil”), behenic acid, stearic acid and mixtures thereof. It is particularly preferred that the fatty acid is a mixture of fatty acids obtained from the seed oil of American
  • Honey foam herb (“meadowfoam seed oil”) are obtained, includes. It is extremely preferred that the fatty acid is a mixture of fatty acids obtained from the seed oil of American
  • a suitable reaction product of a hydroxy-terminated polyorganosiloxane with a fatty acid is, for example, under the name Fancorsil LIM-2 (INCI: Dimethiconol Meadowfoamate) from Fancorsil LIM-2 (INCI: Dimethiconol Meadowfoamate) from Fancorsil LIM-2 (INCI: Dimethiconol Meadowfoamate) from Fancorsil LIM-2 (INCI: Dimethiconol Meadowfoamate) from Fancorsil LIM-2 (INCI: Dimethiconol Meadowfoamate) from Fancorsil LIM-2 (INCI: Dimethiconol Meadowfoamate) from Fancorsil LIM-2 (INCI: Dimethiconol Meadowfoamate) from Fancorsil LIM-2 (INCI: Dimethiconol Meadowfoamate) from Fancorsil LIM-2 (INCI: Dimethiconol Meadowfoamate) from Fancorsil
  • the method is characterized in that the agent (c) contains:
  • agent (c) contains:
  • the method is characterized in that the agent (c) - based on the total weight of the agent (c) - is the reaction product of a hydroxy-terminated polyorganosiloxane with an acid and / or an alcohol and / or a wax ( c2) in an amount from 0.1 to 10% by weight, preferably from 0.2 to 8% by weight, more preferably from 0.3 to 6% by weight, even more preferably from 0.4 to 4% by weight. -% and particularly preferably from 0.5 to 2% by weight.
  • the means (a), (b) and (c) described above can also contain one or more optional ingredients.
  • the agents can additionally contain one or more surfactants.
  • surfactants is understood to mean surface-active substances. A distinction is made between anionic surfactants consisting of a hydrophobic residue and a negatively charged hydrophilic head group, amphoteric surfactants, which carry both a negative and a compensating positive charge, cationic surfactants, which have a positively charged hydrophilic group in addition to a hydrophobic residue, and nonionic surfactants, which have no charges but rather strong dipole moments and are strongly hydrated in aqueous solution.
  • Zwitterionic surfactants are surface-active compounds which have at least one quaternary ammonium group and at least one -COO ⁇ -> or -S03 () group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinates, for example coconut alkyl dimethylammonium glycinate, N-acyl aminopropyl-N, N-dimethylammonium glycinates, for example cocoacylaminopropyl dimethylammonium glycinate, and 2-alkyl -3-carboxymethyl-3-hydroxyethyl-imidazolines each with 8 to 18 carbon atoms in the alkyl or acyl group and that
  • Cocoacylaminoethyl hydroxyethyl carboxymethyl glycinate Cocoacylaminoethyl hydroxyethyl carboxymethyl glycinate.
  • a preferred zwitterionic surfactant is the fatty acid amide derivative known under the INCI name Cocamidopropyl Betaine.
  • Ampholytic surfactants are surface-active compounds which, in addition to a Cs-C24 -alkyl or -acyl group, contain at least one free amino group and at least one —COOH or —SOsH group and are capable of forming internal salts.
  • ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids with each about 8 to 24 carbon atoms in the alkyl group.
  • Typical examples of amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amido betaines, aminopropionates, aminoglycinates,
  • Imidazolinium betaines and sulfobetaines.
  • ampholytic surfactants are N-cocoalkylaminopropionate, the
  • the agents can also contain at least one nonionic surfactant.
  • Suitable nonionic surfactants are alkyl polyglycosides and alkylene oxide addition products with fatty alcohols and fatty acids with 2 to 30 moles of ethylene oxide per mole of fatty alcohol or fatty acid. Preparations with good properties are also obtained if, as nonionic surfactants, they contain fatty acid esters of ethoxylated glycerol which have been reacted with at least 2 mol of ethylene oxide.
  • the agent (c) also contains an alkoxylated fatty alcohol.
  • the fatty alcohol can be selected, for example, from Cg-Cn fatty alcohols, C 12 -C 13 fatty alcohols, Ci2-Ci5 fatty alcohols, Ci 2 -Ci6 fatty alcohols, Cu-Cis fatty alcohols, arachidyl alcohol, behenyl alcohol, capryl alcohol, cetearyl alcohol, cetyl alcohol, coconut alcohol, decyl alcohol,
  • the alkoxy group can in particular comprise ethoxy and / or propoxy and / or butoxy groups.
  • the alkoxylated fatty alcohol is particularly preferably an ethoxylated fatty alcohol.
  • the at least one alkoxy group of the “alkoxylated fatty alcohol” can be derived, for example, from an alkoxylation reaction with alkylene oxide, in particular ethylene oxide and / or propylene oxide.
  • alkoxylated fatty alcohol is selected from the group consisting of ceteareth-2, ceteareth-3, ceteareth-4, ceteareth-5, ceteareth-6, ceteareth-7, ceteareth-8,
  • ceteareth-2 stands for a C16-C18 fatty alcohol with
  • the alkoxylated fatty alcohol comprises ceteareth-20.
  • the amount of the alkoxylated fatty alcohol is preferably 0.1 to 5% by weight and more preferably 0.25 to 3% by weight, based in each case on the total amount of agent (c).
  • the agents can also contain at least one cationic surfactant.
  • Cationic surfactants are understood to mean surfactants, that is to say surface-active compounds, each with one or more positive charges. Cationic surfactants only contain positive charges. These surfactants are usually composed of a hydrophobic part and a hydrophilic head group, the hydrophobic part usually consisting of a hydrocarbon structure (e.g. consisting of one or two linear or branched alkyl chains), and the positive charge (s) are located in the hydrophilic head group. Examples of cationic surfactants are examples of cationic surfactants.
  • Quaternary ammonium compounds which can carry one or two alkyl chains with a chain length of 8 to 28 C atoms as hydrophobic radicals,
  • the cationic charge can also be part of a heterocyclic ring (e.g. an imidazolium ring or a pyridinium ring) in the form of an onium structure.
  • the cationic surfactant can also contain other uncharged functional groups, as is the case, for example, with ester quats.
  • the cationic surfactants are used in a total amount of 0.1 to 45% by weight, preferably 1 to 30% by weight and very particularly preferably 1 to 15% by weight, based on the total weight of the respective agent.
  • the agent (c) is free of cationic surfactants, since these can have a destabilizing effect. “Free of” means that the agent (c) has a maximum of 0.2% by weight and preferably 0% by weight. %, based in each case on the total weight of the agent (c), of cationic surfactants.
  • the agents can also contain at least one anionic surfactant.
  • the anionic surfactants used are surface-active agents with exclusively anionic charges (neutralized by a corresponding counter cation).
  • Examples of anionic surfactants are fatty acids, alkyl sulfates, alkyl ether sulfates and ether carboxylic acids with 12 to 20 carbon atoms in the alkyl group and up to 16 glycol ether groups in the molecule.
  • the anionic surfactants are used in a total amount of 0.1 to 45% by weight, preferably 1 to 30% by weight and very particularly preferably 1 to 15% by weight, based on the total weight of the respective agent.
  • the agents (a), (b) and (c) can also contain at least one alkalizing agent and / or acidifying agent.
  • the pH values in the context of the present invention are pH values that were measured at a temperature of 22 ° C.
  • the agents (a), (b) and (c) can contain, for example, ammonia, alkanolamines and / or basic amino acids as alkalizing agents.
  • the alkanolamines that can be used in the agents are preferably selected from primary amines with a C2-C6-alkyl parent structure which carries at least one hydroxyl group.
  • Preferred alkanolamines are selected from the group which is formed from 2-aminoethan-1 -ol (monoethanolamine), 3-aminopropan-1 -ol, 4-aminobutan-1 -ol, 5-aminopentan-1 -ol, 1-aminopropane -2-ol, 1-aminobutan-2-ol, 1-aminopentan-2-ol, 1-aminopentan-3-ol, 1-aminopentan-4-ol, 3-amino-2-methylpropan-1-ol, 1 - Amino-2-methylpropan-2-ol, 3-aminopropan-1, 2-diol, 2-amino-2-methylpropan-1, 3-diol.
  • alkanolamines are selected from 2-aminoethan-1-ol and / or 2-amino-2-methylpropan-1 -ol.
  • a particularly preferred embodiment is therefore characterized in that an agent (a), (b) and / or (c) as alkalizing agent is an alkanolamine selected from 2-aminoethan-1-ol and / or 2-amino-2-methylpropane-1 -ol contains.
  • amino acid in the context of the invention is an organic compound which in its structure contains at least one amino group which can be protonated and at least one —COOH or one —SOsH group.
  • Preferred amino acids are aminocarboxylic acids, in particular a- (alpha) - aminocarboxylic acids and w-aminocarboxylic acids, with a-aminocarboxylic acids being particularly preferred.
  • basic amino acids are to be understood as meaning those amino acids which have an isoelectric point p1 greater than 7.
  • Basic ⁇ -aminocarboxylic acids contain at least one asymmetric carbon atom.
  • both possible enantiomers can be used equally as specific compounds or mixtures thereof, in particular as racemates. It is however, it is particularly advantageous to use the naturally preferred isomeric form, usually in the L configuration.
  • the basic amino acids are preferably selected from the group that is formed from arginine, lysine, ornithine and histidine, particularly preferably from arginine and lysine.
  • an agent according to the invention is therefore characterized in that the alkalizing agent is a basic amino acid from the group arginine, lysine, ornithine and / or histidine.
  • agents (a), (b) and / or (c) can contain further alkalizing agents, in particular inorganic alkalizing agents.
  • Inorganic alkalizing agents that can be used are preferably selected from the group formed by sodium hydroxide, potassium hydroxide, calcium hydroxide, barium hydroxide, sodium phosphate, potassium phosphate, sodium silicate,
  • alkalizing agents are ammonia and 2-aminoethan-1-ol
  • Acidifying agents familiar to the person skilled in the art are, for example, organic acids such as citric acid, acetic acid, maleic acid, lactic acid, malic acid or tartaric acid, and dilute mineral acids such as hydrochloric acid, sulfuric acid or phosphoric acid.
  • the agent (c) has a pH in the range from 2.5 to 6.5, preferably 2.5 to 5.5, particularly preferably 2.5 to 4.5 and particularly preferably 2.5 to 3.5. Lactic acid is particularly preferably used to adjust the pH.
  • the agent (c) contains the organic acid, in particular lactic acid, preferably in an amount of 0.1 to 5% by weight and particularly preferably from 0.25 to 3% by weight, each based on the weight of the agent (c ).
  • the process is characterized in that the agent (c) has a pH of 2.5 to 3.5.
  • the agents (a), (b) and / or (c) can also contain other active ingredients, auxiliaries and additives, such as solvents, fatty components such as Cs-C3o fatty acid triglycerides, C8-C30 fatty acid monoglycerides, the C8-C3o fatty acid diglycerides and / or the hydrocarbons; Polymers; Structurants such as glucose or sodium chloride,
  • hair conditioning compounds such as phospholipids, for example lecithin and cephalins;
  • Perfume oils, dimethyl isosorbide and cyclodextrins fiber structure-improving active ingredients, in particular mono-, di- and oligosaccharides such as, for example, glucose, galactose, fructose, fruit sugar and lactose; Dyes for coloring the agent; Anti-dandruff ingredients such as Piroctone Olamine, Zinc Omadine and Climbazole; Amino acids and oligopeptides; Protein hydrolysates based on animals and / or plants, and in the form of their fatty acid condensation products or optionally anionically or cationically modified derivatives; vegetable oils; Sunscreens and UV blockers; Active ingredients such as panthenol, pantothenic acid, pantolactone, allantoin, pyrrolidinone carboxylic acids and their salts, and bisabolol; Polyphenols, in particular hydroxycinnamic acids, 6,7-dihydroxycoumarins, hydroxybenzoic acids, catechins, tannins
  • Opacifiers such as latex, styrene / PVP and styrene / acrylamide copolymers; Pearlescent agents like
  • Ethylene glycol mono- and distearate and PEG-3 distearate as well as propellants such as propane-butane mixtures, N2O, dimethyl ether, CO2 and air.
  • the agent (b) very particularly preferably additionally contains at least one film-forming polymer.
  • the at least one film-forming polymer is preferably selected from the group of
  • Copolymers of acrylic acid copolymers of methacrylic acid, homopolymers or
  • Homopolymers or copolymers of propylene homopolymers or copolymers of styrene, polyurethanes, polyesters and / or polyamides.
  • the fastness properties, in particular the wash fastness, of the colored keratinic material can be significantly improved by using a film-forming polymer in the agent (b).
  • an agent (b) is applied to the keratinic material, the agent (b) containing at least one coloring compound from the group of pigments and / or substantive dyes and a film-forming polymer.
  • the agent (c) very particularly preferably additionally contains at least one fatty alcohol.
  • the fatty alcohol can be selected, for example, from Cg-Cn fatty alcohols, C12-C13 fatty alcohols, Ci 2 -Ci5 fatty alcohols, Ci2-Ci6 fatty alcohols, Cu-Cis fatty alcohols, arachidyl alcohol, behenyl alcohol, capryl alcohol, cetearyl alcohol, cetyl alcohol, Decyl alcohol,
  • the fatty alcohol comprises
  • the amount of fatty alcohol is preferably 0.5 to 10% by weight, more preferably 1 to 9% by weight and particularly preferably 2 to 8% by weight, based in each case on the total amount of agent (c).
  • the person skilled in the art will select these additional substances according to the desired properties of the agents. With regard to further optional components and the amounts of these components used, express reference is made to the relevant manuals known to the person skilled in the art.
  • the additional active ingredients and auxiliaries are preferably used in the agents (a), (b) and / or (c) in amounts of 0.0001 to 25% by weight each, in particular 0.0005 to 15% by weight, based on the total weight of the respective agent.
  • agents (a), (b) and (c) are applied to the keratinic materials, in particular to human hair.
  • means (a), (b) and (c) are the means ready for use.
  • the means (a), (b) and (c) are different from each other.
  • the means (a), (b) and (c) can in principle be applied simultaneously or successively, with successive application being preferred.
  • agent (a) was applied as a pretreatment agent to the keratinic materials, then the agent (b) was used as a coloring agent, and then the agent (c) was applied as an aftertreatment agent.
  • a method for coloring keratinic material, in particular human hair, comprising the following steps in the specified is therefore very particularly preferred
  • an agent (b) to the keratinous material, the agent (b) containing at least one coloring compound from the group of pigments and / or substantive dyes,
  • an agent (c) to the keratinous material, the agent (c) containing:
  • (c2) a reaction product of a hydroxy-terminated polyorganosiloxane with an acid and / or an alcohol and / or a wax.
  • the agents (a), (b) and (c) are also particularly preferably used within one and the same coloring process, which means that between the use of the agents ( a) and (c) a period of a maximum of a few hours.
  • the method is characterized in that the agent (a) is applied first, then the agent (b) is applied and in the
  • the agent (c) is applied, the period between the application of the agents (a) and (c) being a maximum of 24 hours, preferably a maximum of 12 hours and particularly preferably a maximum of 6 hours.
  • the keratinic materials in particular the human hair, are first treated with agent (a).
  • agent (a) which contains the coloring compounds - is then applied to the keratinic materials.
  • the agent (a) itself preferably contains no dyes or no coloring compounds.
  • the pretreatment agent (a) is characterized by its content of at least one reactive organic silicon compound.
  • a coloring agent (b) is then applied to the hair. During the application of the coloring agent (b), the coloring compounds interact with that of the organosilicon
  • the rinsing out of the keratinic material with water in steps (3), (6) and (9) of the method is understood to mean that only water is used for the rinsing process, without any additional means (a), ( b) and (c) different means would be used.
  • the agent (a) is first applied to the keratinic materials, in particular the human hair.
  • the agent (a) is allowed to act on the keratinic materials.
  • exposure times of 10 seconds to 10 minutes, preferably 20 seconds to 5 minutes and very particularly preferably 30 seconds to 2 minutes, on the keratinic materials, in particular on human hair, have proven to be particularly advantageous.
  • the agent (a) can now be rinsed out of the keratinic materials before the agent (b) is applied to the hair in the subsequent step.
  • step (4) the agent (b) is now applied to the keratinic materials. After application, the agent (b) is now allowed to act on the hair.
  • step (6) agent (b) (and any agent (a) that is still present) is then rinsed out of the keratinic material with water. Following this, the agent (c) is then applied to the keratinous materials in an aftertreatment step. The agent (c) is also allowed to act on the keratinic materials and then rinsed out again with water.
  • the positive effects achieved by the agent (c) are particularly long-lasting if the agent (c) is used repeatedly - for example in the course of regular hair washing.
  • Multi-component packaging unit (kit-of-parts)
  • the three remedies (a), (b) and (c) are the ready-to-use remedies.
  • the user is preferably provided with all the necessary means in the form of a multi-component packaging unit (kit-of-parts).
  • a second subject of the present invention is therefore a multi-component packaging unit (kit-of-parts) for coloring keratinic material, comprehensively packaged separately from one another
  • (c2) a reaction product of a hydroxy-terminated polyorganosiloxane with an acid and / or an alcohol and / or a wax.
  • the organic silicon compounds contained in the middle (a) of the kit correspond to the organic silicon compounds which were also used in the middle (a) of the method described above.
  • the coloring compounds from the group of pigments and / or substantive dyes contained in agent (b) of the kit correspond to the coloring compounds from the group of pigments and / or substantive dyes, which are also used in agent (b) of the method described above were.
  • the agent (a) contains with the organic silicon compound or compounds, a class of reactive compounds which, as described above, undergo hydrolysis and / or in the presence of water Oligomerization and / or polymerization can enter. As a result of their high reactivity, these organic silicon compounds form a film on the keratinous material.
  • the ready-to-use agent (a) is not produced until shortly before use.
  • a multi-component packaging unit for coloring keratinous material is packaged comprehensively separately from one another
  • (c2) a reaction product of a hydroxy-terminated polyorganosiloxane with an acid and / or an alcohol and / or a wax.
  • the agent (a1) itself is preferably formulated to be low in water or anhydrous.
  • a multi-component packaging unit (kit-of-parts) is characterized in that the agent (a1) - based on the total weight of the agent (a1) - has a water content of less than 10% by weight, preferably less than 5% by weight, more preferably less than 1% by weight, even more preferably less than 0.1% by weight and very particularly preferably less than 0.01% by weight.
  • the agent (a2) contains water.
  • a multi-component packaging unit (kit-of-parts) is characterized in that the agent (a2) - based on the total weight of the agent (a2) - has a water content of 15 to 100% by weight, preferably from 35 to 100% % By weight, more preferably from 55 to 100% by weight, even more preferably from 65 to 100% by weight and very particularly preferably from 75 to 100% by weight.
  • the ready-to-use agent (a) is now produced by mixing the agents (a1) and (a2).
  • the user can first stir or spill the agent (a1) which contains the organic silicon compound (s) with the water-containing agent (a2).
  • the user can now use this mixture of (a1) and (a2) - either immediately after it has been produced or after a short time Reaction time from 10 seconds to 20 minutes - apply to the keratinic materials.
  • the user can then use means (b) and (c) as described above.
  • silanes were mixed with some of the water, this mixture was allowed to stand for 30 minutes.
  • the pH was then adjusted to the desired value by adding citric acid / ammonia. It was then made up to 100 g with water.
  • the strands of hair were each dipped into the agent (b) and left in it for 1 minute. Thereafter, excess agent (b) was stripped from each strand of hair. Each strand of hair was briefly washed out with water. Excess water was wiped off each strand of hair.
  • the hair tresses were each wetted with a small amount of the agent (c).
  • the agent (c) was left to act for 1 minute. It was then washed out with water and the lock of hair was dried. The tresses were then assessed visually.

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Abstract

La présente invention concerne un procédé de coloration d'une matière kératinique, en particulier de cheveux, ce procédé comprenant les étapes suivantes : - application d'un produit (a) sur la matière kératinique, le produit (a) contenant au moins un composé organique du silicium, - l'application d'un produit (b) sur la matière kératinique, le produit (b) contenant au moins un composé colorant du groupe des pigments et/ou des colorants directs, - l'application d'un produit (c) sur la matière kératinique, le produit (c) contenant : (c1) un polyorganosiloxane à terminaison hydroxy et (c2) un produit de réaction d'un polyorganosiloxane à terminaison hydroxy avec un acide et/ou un alcool et/ou une cire. L'invention concerne aussi une unité d'emballage à plusieurs composants, laquelle contient dans trois conteneurs fabriqués séparément les trois produits (a), (b) et (c).
EP20707613.4A 2019-03-12 2020-02-27 Procédé de coloration de matière kératinique, comprenant l'utilisation d'un composé organique du silicium, un composé colorant et un mélange de silicones Withdrawn EP3937889A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102019203298.2A DE102019203298A1 (de) 2019-03-12 2019-03-12 Verfahren zum Färben von keratinischem Material, umfassend die Anwendung von einer siliciumorganischen Verbindung, einer farbgebenden Verbindung und einer Mischung aus Silikonen
PCT/EP2020/055079 WO2020182474A1 (fr) 2019-03-12 2020-02-27 Procédé de coloration de matière kératinique, comprenant l'utilisation d'un composé organique du silicium, un composé colorant et un mélange de silicones

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EP3937889A1 true EP3937889A1 (fr) 2022-01-19

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EP20707613.4A Withdrawn EP3937889A1 (fr) 2019-03-12 2020-02-27 Procédé de coloration de matière kératinique, comprenant l'utilisation d'un composé organique du silicium, un composé colorant et un mélange de silicones

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US (1) US20220151901A1 (fr)
EP (1) EP3937889A1 (fr)
JP (1) JP2022525129A (fr)
CN (1) CN113557003A (fr)
DE (1) DE102019203298A1 (fr)
WO (1) WO2020182474A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3134000A1 (fr) * 2022-03-31 2023-10-06 L'oreal Procédé de coloration des cheveux comprenant l’application d’une composition A comprenant deux alcoxysilanes, et l’application d’une composition B comprenant un polymère filmogène, la composition A et/ou la composition B comprenant un agent colorant et un acide aminé
FR3134003A1 (fr) * 2022-03-31 2023-10-06 L'oreal Procédé pour retirer la couleur de fibres kératiniques préalablement colorées avec deux alcoxysilanes, un polymère filmogène, un polymère cellulosique non ionique et un agent colorant
FR3133999A1 (fr) * 2022-03-31 2023-10-06 L'oreal Procédé de coloration des cheveux comprenant l’application d’une composition A comprenant deux alcoxysilanes, et l’application d’une composition B comprenant un polymère filmogène, la composition A et/ou la composition B comprenant un agent colorant et une silicone aminée

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2865395B1 (fr) * 2004-01-28 2006-06-23 Oreal Composition de teinture des fibres keratiniques contenant une alcool oxydase et une silicone aminee ou oxyalkylenee, procede mettant en oeuvre cette composition
DE102005062025A1 (de) * 2005-12-22 2007-06-28 Henkel Kgaa Imidazolylmethyl-substituierte Entwickler
EP2168633B1 (fr) 2008-09-30 2016-03-30 L'Oréal Composition cosmétique comprenant un composé organique du silicium comportant au moins une fonction basique, un polymère filmogène hydrophobe, un pigment et un solvant volatil
FR2982155B1 (fr) * 2011-11-09 2014-07-18 Oreal Composition cosmetique comprenant au moins un alcoxysilane
DE102014222374A1 (de) * 2014-11-03 2016-05-04 Henkel Ag & Co. Kgaa Oxidationsfärbemittel, enthaltend eine Kombination aus vernetzten, aminierten Siloxanpolymeren und nichtionischen Tensiden
DE102014226177A1 (de) * 2014-12-17 2016-06-23 Henkel Ag & Co. Kgaa Verfahren zum Farberhalt gefärbter und/oder aufgehellter keratinischer Fasern
FR3060980B1 (fr) 2016-12-22 2019-05-31 L'oreal Procede de coloration des fibres keratiniques mettant en oeuvre une composition comprenant au moins deux organosilanes differents l'un de l'autre

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CN113557003A (zh) 2021-10-26
JP2022525129A (ja) 2022-05-11
DE102019203298A1 (de) 2020-09-17
US20220151901A1 (en) 2022-05-19
WO2020182474A1 (fr) 2020-09-17

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