WO2024022647A1 - Procédé de coloration d'une matière kératinique, comprenant le procédé de traitement de la matière kératinique à l'aide d'un plasma et de l'utilisation d'un colorant - Google Patents

Procédé de coloration d'une matière kératinique, comprenant le procédé de traitement de la matière kératinique à l'aide d'un plasma et de l'utilisation d'un colorant Download PDF

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Publication number
WO2024022647A1
WO2024022647A1 PCT/EP2023/064375 EP2023064375W WO2024022647A1 WO 2024022647 A1 WO2024022647 A1 WO 2024022647A1 EP 2023064375 W EP2023064375 W EP 2023064375W WO 2024022647 A1 WO2024022647 A1 WO 2024022647A1
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Prior art keywords
colorant
pigments
weight
group
plasma
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PCT/EP2023/064375
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German (de)
English (en)
Inventor
Ranju Prasad Mandal
Phillip Jaiser
Ulrike Schumacher
Daniela Kessler-Becker
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Henkel Ag & Co. Kgaa
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Publication of WO2024022647A1 publication Critical patent/WO2024022647A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—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
    • 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
    • A61K8/72—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
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30—Characterized by the absence of a particular group of ingredients
    • 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
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/83—Electrophoresis; Electrodes; Electrolytic phenomena

Definitions

  • Method for dyeing keratin material comprising the treatment of the keratin material with plasma and the application of a colorant.
  • the subject of the present application is a method for coloring keratin material, in particular human hair, which comprises the treatment of the keratin material with plasma and the use of a colorant (F ).
  • the colorant (F) is characterized in that it contains at least one organic amino compound (F1) and at least one pigment (F3) and is also essentially free of acrylate-based polymers (F3).
  • Oxidation dyes are usually used for permanent, intensive dyeing with good fastness properties and good gray coverage. Such dyes contain oxidation dye precursors, so-called developer components and coupler components, which form the actual dyes among themselves under the influence of oxidizing agents such as hydrogen peroxide. Oxidation dyes are characterized by very long-lasting dyeing results. When using direct dyes, already formed dyes diffuse from the dye into the hair fiber. Compared to oxidative hair coloring, the colorings obtained with direct dyes are less durable and wash out more quickly. Dyes with direct dyes usually remain on the hair for a period of between 5 and 20 washes. The use of color pigments is known for short-term color changes on the hair and/or skin. Color pigments are generally understood to mean insoluble, coloring substances.
  • a possible, alternative coloring system that has recently come into focus is based on the use of colored pigments.
  • Coloring with pigments offers several significant advantages. Since the pigments only attach to the keratin fibers, especially the hair fibers, from the outside, the damage associated with the dyeing process is particularly minimal. Furthermore, dyes that are no longer desired can be removed quickly and easily without leaving any residue, thus offering the user the opportunity to return to their original hair color immediately and without much effort. This coloring process is particularly attractive for consumers who do not want to dye their hair regularly. Current work has addressed the problem of the low durability of this dyeing system. Since the pigments are deposited exclusively in the form of a film on the outside of the keratin fibers, they are particularly sensitive to external influences, such as those that occur when washing your hair.
  • the washing fastness of pigment-based keratin and hair dyes therefore still needs to be improved. It was the object of the present invention to provide a dyeing system which, if possible, has fastness properties comparable to oxidative dyeing. In particular, the washing fastness should be outstanding, but the use of the oxidation dye precursors that are otherwise commonly used for this purpose should be avoided.
  • the search was for a technology that would make it possible to fix pigments on the hair in an extremely permanent way. When using the agents in a dyeing process, intensive dyeing results with good fastness properties, in particular good fastness to washing and good color retention, should be achieved.
  • the subject of the present invention is a method for coloring keratinic material, in particular human hair, comprising the following steps: (1) treating the keratinic material with a plasma, and (2) treating the keratinic material with a coloring agent (F), where the dye (F) - based on the total weight of the dye (F) - contains: (F1) at least one organic amino compound, and
  • a dye that contained at least one organic amino compound (F1) and at least one pigment (F2) was applied to the keratin material or the hair.
  • the organic amino compound (F1) and the pigment (F2) together formed a film that was particularly robust when the colorant was essentially free of acrylate-based polymers (F3).
  • the colorant (F) used in the process according to the invention is characterized in that it contains the acrylate-based polymers in a total amount of less than 1.0% by weight. If the keratin materials treated with the dye (F) were now additionally subjected to a plasma treatment, the color results were characterized by greatly improved fastness properties, in particular by greatly improved fastness to washing.
  • Keratin material means hair, skin, nails (such as fingernails and/or toenails). Wool, fur and feathers also fall under the definition of keratin material.
  • Keratin material is preferably understood to mean human hair, human skin and human nails, in particular fingernails and toenails. Keratin material is particularly preferably understood to mean human hair.
  • the keratin material is treated with a plasma.
  • Human hair is particularly preferably treated with the plasma.
  • a plasma is understood to mean a particle mixture of ions, free electrons and, if appropriate, neutral atoms and/or molecules.
  • a plasma is characterized by the fact that it contains free charge carriers.
  • a plasma is understood to mean, in particular, an ionized gas.
  • the degree of ionization of a plasma according to the invention can vary and can be, for example, in the range from 0.1 to 100% or even from 1 to 100%. At an ionization level of 100%, 100% of the particles are ionized, so in this case there is complete ionization.
  • the essential property of a plasma is its electrical conductivity.
  • a plasma can be created, for example, by blowing a working gas through an electric arc under normal pressure (1013 mbar) and normal temperature (20 °C). When the working gas exits the arc, the so-called plasma jet is obtained, ie a gas is obtained that is at least partially split into ions and electrons.
  • air, helium or oxygen can be used as gases. In an atmospheric plasma, air is used as the working gas.
  • the method according to the invention comprises:
  • a cold plasma is a plasma that does not cause excessive heating of the substrate exposed to the plasma.
  • the keratin material does not heat up to physiologically unacceptable temperatures of more than 40 ° C over the duration of the treatment.
  • just enough energy is added to the gas (or air) so that it is only partially ionized (in many commercially available devices, for example, only one particle out of 10 9 particles is ionized). Due to the low degree of ionization, the temperature can be controlled so that it remains below 40 °C.
  • the method according to the invention therefore comprises:
  • the method according to the invention in this embodiment includes
  • a direct plasma the substrate acts as a counter electrode, which is necessary to generate the plasma.
  • the plasma is therefore generated between the electrode and the substrate.
  • DBD plasma Dielectric Barrier Discharge
  • an indirect plasma the plasma is generated between two electrodes and then directed onto the substrate or onto the keratinous material using a gas stream.
  • An indirect plasma can be generated, for example, with a plasma torch become.
  • Hybrid plasmas, so-called corona plasmas combine the production method of a direct plasma with the properties of indirect plasmas.
  • the keratin material acts as a counter electrode and the area beneath the electrode is treated.
  • step (1) of the method for example, individual parts of the keratin material, such as individual strands of hair, can be treated with the plasma, or the plasma treatment can be carried out on the entire keratin material or on the entire hair.
  • the electrode or the source of plasma generation is kept at a controlled distance from the keratin material while it is moved on the surface of the keratin material. This movement can be carried out manually or automatically. In the case of a manual movement, this can optionally be supported by a guide structure placed around the person's head.
  • a plasma in particular a cold plasma.
  • the plasma can be transported to a nozzle through a flexible tube, for example.
  • the nozzle through which the plasma stream flows can be guided over the keratin material to carry out the plasma treatment.
  • the Plasma Care® device from Terraplasma Medical GmbH can be used as a particularly suitable device in the method according to the invention.
  • the devices in the Plasma Care® product line are handy and designed for mobile use.
  • the plasma source of this type of device the plasma is generated by micro-discharges.
  • the plasma source is equipped with very thin ceramic plates and sensitive electrical contacts. During each treatment, a spacer is placed on the device to ensure a controlled, consistent distance between the plasma source and the keratin material.
  • the device uses thin-film technology, which represents a further development of surface micro-discharge technology (SMD for short).
  • the plasma source unit consists of a high-voltage electrode, a dielectric and the grounded structured electrode.
  • the treatment of the keratin material with plasma is preferably carried out at atmospheric pressure (1,013 x 10 5 Pa).
  • the treatment of the keratin material with plasma (1) can be carried out at different times. For example, it is possible to subject the still dry keratin material or the still dry hair to the plasma treatment right at the beginning of the process. A dyeing process in which dry hair was treated with plasma has also led to dyes with very good wash fastness.
  • Dyes with also very good wash fastness could be obtained if the plasma treatment was carried out on moistened keratin material or moistened or towel-dried hair.
  • Moistened or towel-dried hair refers to hair that has been completely wetted with water at the sink or in the shower, then squeezed out and rubbed dry with a towel (e.g. for 30 seconds). Moistened or towel-dried hair is therefore no longer dripping wet, but is still damp.
  • the method according to the invention therefore comprises:
  • Keratin material such as hair, which was moistened shortly before application, was moistened within a period of a maximum of 30 minutes, preferably a maximum of 10 minutes and particularly preferably a maximum of 5 minutes before application.
  • the method according to the invention therefore comprises:
  • the treatment of the keratin material with plasma can take place over different periods of time.
  • the keratin material can be used, for example, over a period of 15 seconds to 15 minutes, preferably 30 seconds up to 5 minutes and most preferably from 45 seconds to 2 minutes.
  • the method according to the invention is therefore characterized by the treatment of the keratinic material with plasma (1) for a period of 15 seconds to 15 minutes, preferably 30 seconds to 5 minutes and most preferably 45 seconds to 2 minutes .
  • the keratin material can generally first be treated with plasma in the first step (1), after which the dye (F) is then subsequently applied to the keratin material in step (2).
  • the reverse order i.e. first staining the keratin material with the dye (F) and the subsequent treatment of the already colored keratin material with plasma, is also conceivable in principle.
  • dyeings with good fastness properties could be obtained particularly when the treatment of the keratin material with plasma represents a pretreatment before the subsequent dyeing step with the dye (F).
  • the wash fastnesses of the dyes obtained when hair was first treated with cold atmospheric plasma and then dyed with the dye (F) were greatly improved.
  • the method according to the invention is not subject to any restrictions with regard to the time periods that can lie between steps (1) and (2).
  • steps (1) and (2) are carried out within a staining process that is completed within a period of a few hours.
  • the tests carried out also showed that dyeings with very good washing fastness were obtained in particular when there was a maximum period of time of 72 hours, preferably a maximum of 48 hours, more preferably a maximum of 24 hours, between the plasma treatment in step (1) and the dyeing step (2). even more preferably a maximum of 2 hours and very particularly preferably a maximum of 30 minutes.
  • a method comprising (1) treating the keratinous material with plasma in a first step, followed by (2) treating the keratinic material with the colorant (F) in a second step, where between steps (1) and (2) there is a period of a maximum of 72 hours, preferably a maximum of 48 hours, more preferably a maximum of 24 hours, even more preferably a maximum of 2 hours and most preferably a maximum of 30 minutes.
  • step (2) of the method according to the invention the keratin material is treated with the colorant (F).
  • the colorant (F) is characterized in that it contains - based on the total weight of the colorant (F) -:
  • coloring agent is used in the context of this invention for a coloring of the keratin material, in particular the hair, caused by the use of pigments.
  • the aforementioned pigments (F2) are deposited in a particularly homogeneous and smooth film on the surface of the keratin material.
  • the pigments (F2) together with the organic amino compound(s) (F1) enclose the surface of the keratin material, in particular the keratin fiber.
  • An organic amino compound is understood to mean an organic substance, i.e. a substance with at least one carbon atom, which additionally comprises at least one amino group. It is assumed that this amino group interacts with the surface of the keratin material when the coloring agent (F) is used, which leads to the amino compounds (F1) being deposited on the surface and enclosing the pigments (F2) in this deposition .
  • organic amino compounds (F1) are particularly suitable for film formation together with the pigments (F2).
  • Organic C 1 -C 6 alkoxysilanes and their condensation products as well as amino-functionalized silicone polymers have proven to be particularly suitable in this context.
  • a process is particularly preferred which comprises the use of a colorant (F) which (F1) contains at least one organic amino compound which is selected from the group of organic C 1 -C 6 alkoxysilanes, their condensation products and amino-functionalized silicone polymers.
  • Organic C 1 -C 6 alkoxysilanes (F1) are reactive compounds.
  • Organic silicon compounds which are also 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 silicon atom is linked.
  • the organic C 1 -C 6 alkoxysilanes according to the invention are compounds which contain one to three silicon atoms.
  • the organic C 1 -C 6 alkoxysilanes particularly preferably contain one or two silicon atoms.
  • silane stands for a group of chemical compounds that are based on a silicon skeleton and hydrogen.
  • organic silanes the hydrogen atoms are 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 hydroxy groups.
  • Organic C 1 -C 6 alkoxy silanes comprising at least one C1-C6 alkoxy group bonded directly to the silicon atom.
  • the alkoxy group is reactive and can first be hydrolyzed in the presence of water and then condensed with another organic C 1 -C 6 alkoxy silane (or its hydrolysis product).
  • the C 1 -C 6 alkoxy group is preferably an ethoxy group or a methoxy group.
  • the organic silicon compound preferably contains a structural unit R'R"R"'Si-O-CH2-CH3.
  • the radicals R', R" and R"' represent the three remaining free valences of the silicon atom.
  • the colorant (F) according to the invention contained at least one first organic C 1 -C 6 alkoxysilane (F1) of the formula (I).
  • a method according to the invention comprising the use of a colorant (F) which (F1) contains at least one organic C 1 -C 6 alkoxysilane of the formula (I) and/or its condensation products
  • R 1 , R 2 , R 3 , R 4 and L in the compounds of the formula (I) are explained below by way of example:
  • Examples of a C 1 -C 6 alkyl group 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 C 2 -C 6 alkenyl group are vinyl, allyl, but-2-enyl, but-3-enyl and isobutenyl; preferred C 2 -C 6 alkenyl radicals are vinyl and allyl.
  • Preferred examples of a hydroxy-C 1 -C 6 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-C 1 -C 6 alkyl group are the aminomethyl group, the 2-aminoethyl group, the 3-aminopropyl group.
  • the 2-aminoethyl group is particularly preferred.
  • Examples of a linear divalent C 1 -C 20 alkylene group are, for example, the methylene group (-CH 2 -), the ethylene group (-CH 2 -CH 2 -), the propylene group (- (-CH 2- CH 2 -CH 2 - and the butylene group (-CH 2 -CH 2 -CH 2 -CH 2 -).
  • the propylene group (-CH 2- CH 2 -CH 2 -) is particularly preferred.
  • divalent alkylene groups can be used also be branched.
  • Examples of branched, divalent C 3 -C 20 alkylene groups are (-CH 2 - CH( C H 3 )-) and (-CH 2 -CH(CH 3 )-CH 2 -).
  • the radicals R1 and R2 independently represent a hydrogen atom or a C 1 -C 6 alkyl group. Very particularly preferably, the radicals R 1 and R 2 both represent a hydrogen atom.
  • the structural unit or linker -L- which stands for a linear or branched, divalent C 1 -C 20 alkylene group.
  • -L- preferably represents a linear, divalent C 1 -C 20 alkylene group. More preferably, -L- represents a linear divalent C 1 -C 6 alkylene group.
  • -L- particularly preferably represents a methylene group (-CH 2 -), an ethylene group (-CH 2 -CH 2 -), a propylene group (-CH 2- CH 2 -CH 2 -) or a butylene group (-CH 2 - CH 2 -CH 2 -CH 2 -).
  • L represents a propylene group (-CH 2 -CH 2 -CH 2 -).
  • the radical R3 represents a hydrogen atom or a C 1 -C 6 alkyl group
  • the radical R4 represents a C 1 -C 6 alkyl group.
  • R3 and R4 particularly preferably independently represent a methyl group or an ethyl group.
  • a stands for an integer from 1 to 3
  • d b stands for the integer 3 - a. If a is the number 3, then b is 0. If a is the number 2, then b is 1. If a is the number 1, then b is 2.
  • the agent according to the invention contains at least one first organic silicon compound (a1) of the formula (I) in which the radicals R3, R4 independently represent a methyl group or an ethyl group.
  • the agent according to the invention contains at least one first organic silicon compound (a1) of the formula (I) in which the radical a represents the number 3. In this case the remainder b represents the number 0.
  • an agent according to the invention is characterized in that it contains at least one first organic silicon compound (a1) of the formula (I), where
  • R3, R4 independently represent a methyl group or an ethyl group
  • an agent according to the invention is characterized in that it contains at least one first organic silicon compound (F1) of the formula (I),
  • R2 both represent a hydrogen atom
  • - L represents a linear, divalent C 1 -C 6 alkylene group, preferably a propylene group (-CH2-CH2-) or an ethylene group (-CH2-CH2-), - R 3 , R 4 independently represent a methyl group or an ethyl group and
  • C 1 -C 6 -alkoxysilanes of the formula (I) are particularly suitable for solving the problem according to the invention
  • a method according to the invention is characterized in that the colorant (F) contains at least one organic C 1 -C 6 alkoxysilane (F1) which is selected from the group consisting of (3-aminopropyl)trimethoxysilane, (3-Aminopropyl)triethoxysilane, (2-Aminoethyl)trimethoxysilane, (2-Aminoethyl)triethoxysilane, (3-Dimethylaminopropyl)trimethoxysilane, (3-Dimethylaminopropyl)triethoxysilane, (2-Dimethylaminoethyl) trimethoxysilane, (2-dimethylaminoethyl)triethoxysilane and their condensation products.
  • F1 organic C 1 -C 6 alkoxysilane
  • the colorant contains (3-aminopropyl)triethoxysilane and/or its condensation products.
  • organic C 1 -C 6 alkoxysilanes of the formula (I) are commercially available.
  • (3-Aminopropyl)trimethoxysilane can be purchased, for example, from Sigma-Aldrich.
  • (3-Aminopropyl)triethoxysilane is also commercially available from Sigma-Aldrich.
  • the dye (F) according to the invention contains at least one organic C in addition to the organic C 1 -C 6 alkoxysilanes of the formula (I). 1 -C 6 alkoxysilane of the formula (II).
  • R 5 Si(OR 6 )k(R 7 )m (II).
  • the organic C 1 -C 6 alkoxysilane(s) of the formula (II) can also be referred to as silanes of the alkyl-alkoxy-silane or alkyl-hydroxy-silane type,
  • R 5 represents a C 1 -C 12 alkyl group
  • R 6 represents a hydrogen atom or a C 1 -C 6 alkyl group
  • R 7 represents a C 1 -C 6 alkyl group
  • the C 1 -C 6 alkoxysilanes of the formula (I) interact in their function as amino compounds (F1) with the surface of the keratin materials and, together with the pigment or pigments (F2), form a film.
  • the resistance of this film can now be further improved if, in addition to the C 1 -C 6 alkoxysilanes of the formula (I), one or more C 1 -C 6 alkoxysilanes of the formula (II) are also incorporated.
  • a colorant (F) which additionally contains at least one organic 6 6 -C 6 -alkoxy-silane of the formula (II) and/or its condensation products contains
  • R 5 represents a Ci-Ci2-alkyl group
  • R 6 represents a hydrogen atom or a C 1 -C 6 alkyl group
  • R 7 represents a C 1 -C 6 alkyl group
  • a colorant (F) used in the process according to the invention is characterized in that, in addition to the organic C 1 -C 6 alkoxysilane(s) of the formula (I), it contains at least one further organic C 1 -C 6 -- Contains alkoxysilane of the formula (II).
  • R 5 represents a Ci-Ci2-alkyl group
  • - R 6 represents a hydrogen atom or a C 1 -C 6 alkyl group
  • - R 7 represents a C 1 -C 6 alkyl group
  • the radical R 5 represents a C 1 -C 12 alkyl group. This C 1 -C 12 alkyl group is saturated and can be linear or branched. R 5 preferably represents a linear C 1 -C 12 alkyl group. R 5 preferably represents a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-octyl group or an n-dodecyl group. R 5 particularly preferably represents a methyl group, an ethyl group or an n-octyl group.
  • the radical R 6 represents a hydrogen atom or a C 1 -C 6 alkyl group.
  • R 6 particularly preferably represents a methyl group or an ethyl group.
  • the radical R 7 represents a C 1 -C 6 alkyl group.
  • R 7 particularly preferably represents a methyl group or an ethyl group.
  • k represents an integer from 1 to 3, and m represents 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.
  • Dyes with the best wash fastness could be obtained if a dye (F) was used in the process which contains at least one organic C 1 -C 6 alkoxysilane of the formula (II) in which the radical k represents the number 3. In this case the remainder m represents the number 0.
  • Organic silicon compounds of the formula (II) are particularly suitable for solving the problem according to the invention
  • a method according to the invention is characterized in that the colorant (F) contains at least one organic C 1 -C 6 alkoxysilane of the formula (II), which is selected from the group consisting of methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane , ethyltriethoxysilane, hexyltrimethoxysilane, hexyltriethoxysilane, octyltrimethoxysilane, octyltriethoxysilane, dodecyltri-methoxysilane, dodecyltriethoxysilane and their condensation products.
  • the colorant (F) contains at least one organic C 1 -C 6 alkoxysilane of the formula (II), which is selected from the group consisting of methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxys
  • organic silicon compounds that are particularly suitable for solving the problem according to the invention are also:
  • a colorant (F) is characterized in that it contains at least one first organic C 1 -C 6 alkoxysilane (F1) of the formula (I), which is selected from Group of (3-aminopropyl)-triethoxysilane and (3-aminopropyl)-trimethoxysilane, and additionally contains at least one second organic C 1 -C 6 alkoxysilane of the formula (II), which is selected from the group of methyltrimethoxy- silane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, hexyltrimethoxysilane and hexyltriethoxysilane.
  • organic C 1 -C 6 alkoxysilanes are reactive compounds.
  • the colorant (F) according to the invention - based on the total weight of the agent - contains one or more organic C 1 -C 6 alkoxysilanes (F1) and / or their condensation products in a total amount from 0.1 to 30.0% by weight, preferably from 0.5 to 20.0% by weight, more preferably from 2.0 to 15.0% by weight and very particularly preferably from 4.0 to Contains 12.5% by weight.
  • a method according to the invention is therefore characterized in that the colorant (F) - based on the total weight of the colorant (F) - contains one or more organic C 1 -C 6 alkoxysilanes ( F1) and/or their condensation products in a total amount of 0.1 to 30.0% by weight, preferably from 0.5 to 20.0% by weight, more preferably from 2.0 to 15.0% by weight. % and very particularly preferably from 4.0 to 12.5% by weight.
  • the optionally additionally contained several organic C 1 -C 6 alkoxy-silanes of the formula (II) can - based on the total weight of the colorant (F) - in a total amount of 0.1 to 30.0% by weight, preferably from 0.5 to 20.0% by weight, more preferably from 2.0 to 15.0% by weight and very particularly preferably from 4.0 to 12.5% by weight in the colorant.
  • organic C 1 -C 6 alkoxysilanes in particular those of the formula (I) and/or (II), are reactive compounds that can undergo hydrolysis and condensation reactions with water.
  • the reaction of the organic C 1 -C 6 alkoxysilanes with water can take place in various ways.
  • the reaction starts as soon as the C 1 -C 6 alkoxysilanes come into contact with water by mixing.
  • an exothermic hydrolysis reaction takes place according to the following scheme (reaction scheme using the example of 3-aminopropyltriethoxysilane):
  • the hydrolysis reaction can also take place several times per C 1 -C 6 alkoxy silane used:
  • the hydrolysis reaction can also take place several times per C 1 -C 6 alkoxysilane used:
  • condensation to form a dimer is shown, but further condensations to form oligomers with several silane atoms are also possible and preferred.
  • the colorant (F) can also contain at least one amino-functionalized silicone polymer as an organic amino compound (F1).
  • the amino-functionalized silicone polymer can alternatively be referred to as amino silicone or amodimethicone.
  • Silicone polymers are generally macromolecules with a molecular weight of at least 500 g/mol, preferably at least 1000 g/mol, more preferably at least 2500 g/mol, particularly preferably at least 5000 g/mol, which comprise repeating organic units.
  • the maximum molecular weight of the silicone polymer depends on the degree of polymerization (number of polymerized monomers) and the batch size and is also determined by the polymerization method. For the purposes of the present invention, it is preferred if the maximum Molecular weight of the silicone polymer is not more than 10 7 g/mol, preferably not more than 10 6 g/mol and particularly preferably not more than 10 5 g/mol.
  • the silicone polymers include many Si-O repeat units, where the Si atoms can carry organic radicals such as alkyl groups or substituted alkyl groups. Alternatively, a silicone polymer is therefore also referred to as polydimethylsiloxane.
  • the silicone polymers are based on more than 10 Si-O repeating units, preferably more than 50 Si-O repeating units and particularly preferably more than 100 Si-O repeating units, most preferably more than 500 Si-O repeating units .
  • An amino-functionalized silicone polymer is understood to mean a functionalized silicone that carries at least one structural unit with an amino group.
  • the amino-functionalized silicone polymer preferably carries several structural units, each with at least one amino group.
  • An amino group is understood to mean a primary amino group, a secondary amino group and a tertiary amino group. All of these amino groups can be protonated in an acidic environment and are then present in their cationic form.
  • a method according to the invention is characterized in that a colorant (F) is applied to the keratin fibers, which comprises at least one amino-functionalized silicone polymer (F1) with at least one secondary amino group.
  • the secondary amino group(s) can be located at different positions of the amino-functionalized silicone polymer. Particularly good color results were obtained when an amino-functionalized silicone polymer was used that has at least one, preferably several, structural units of the formula (Si-Amino). CH3
  • ALK1 and ALK2 independently stand for a linear or branched, divalent Ci-C2o-alkylene group.
  • a method according to the invention is characterized in that the colorant (F) contains at least one amino-functionalized silicone polymer (F1) which comprises at least one structural unit of the formula (Si-Amino),
  • ALK1 and ALK2 independently represent a linear or branched, divalent Ci-C2o-alkylene group.
  • the positions marked with an asterisk (*) indicate the bond to other structural units of the silicone polymer.
  • the silicon that is adjacent to the star can Atom can be bonded to another oxygen atom, and the oxygen atom adjacent to the star can be bonded to another silicon atom or to a C 1 -C 6 alkyl group.
  • a divalent Ci-C2o-alkylene group can alternatively be referred to as a divalent or divalent Ci-C2o-alkylene group, which means that each group ALK1 or AK2 can form two bonds.
  • ALK1 In the case of ALK1, one bond occurs from the silicon atom to the ALK1 moiety, and the second bond is between ALK1 and the secondary amino group.
  • ALK2 In the case of ALK2, one bond occurs from the secondary amino group to the ALK2 moiety, and the second bond is between ALK2 and the primary amino group.
  • Examples of a linear divalent Ci-C2o-alkylene group include 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(CH3)-CH2-).
  • the structural units of the formula (Si-Amino) represent repeat units in the amino-functionalized silicone polymer, so that the silicone polymer comprises several structural units of the formula (Si-Amino).
  • Particularly suitable amino-functionalized silicone polymers with at least one secondary amino group are listed below.
  • Dyes with the very best wash fastness properties could be obtained if, during the dyeing, at least one agent was applied to the keratinic material which contains at least one amino-functionalized silicone polymer which comprises structural units of the formula (Si-I) and the formula (Si-II).
  • a process comprising the use of a colorant (F) which contains at least one amino-functionalized silicone polymer which comprises structural units of the formula (Si-I) and the formula (Si-II) is explicitly particularly preferred
  • a corresponding amino-functionalized silicone polymer with the structural units (Si-I) and (Si-II) is, for example, the commercial product DC 2-8566 or Dowsil 2-8566 Amino Fluid, which is sold commercially by the Dow Chemical Company and which has the name “ Siloxanes and Silicones, 3-[(2-Aminoethyl)amino]-2-methylpropyl Me, Di-Me-Siloxane” and the CAS number 106842-44-8.
  • Another particularly preferred commercial product is Dowsil AP-8568 Amino Fluid, which is also sold commercially by the Dow Chemical Company.
  • Pigments (F2) The colorant (F) used in the process according to the invention contains at least one pigment (F2) as a second essential component.
  • pigments are understood to be coloring compounds which have a solubility in water at 20 ° C 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: 0.5 g of the pigment is weighed out in a beaker. A stir fry is added. Then one liter of distilled water is added. This mixture is heated to 20 °C for one hour while stirring on a magnetic stirrer. If undissolved components of the pigment are still visible in the mixture after this period, the solubility of the pigment is below 0.5 g/L.
  • the mixture is filtered. If a portion of undissolved pigment remains on the filter paper, the solubility of the pigment is below 0.5 g/L.
  • Suitable pigments or color pigments can be of inorganic and/or organic origin.
  • a method according to the invention is characterized in that the colorant (F) contains at least one pigment (F2) from the group of inorganic pigments, organic pigments and/or metal pigments.
  • Preferred color pigments are selected from synthetic or natural inorganic pigments.
  • Inorganic color pigments of natural origin can be made, for example, from chalk, ocher, umber, green earth, fired Terra di Siena or graphite. Black pigments such as black pigments can also be used as inorganic color pigments.
  • B. iron oxide black, colored pigments such as. B. ultramarine or iron oxide red as well as 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 (CI77289 ), Iron Blue (Ferric Ferrocyanide, CI77510) and/or Carmine (Cochineal).
  • Color pigments that are also particularly preferred according to the invention are colored pearlescent pigments. These are usually based on mica and/or mica and can be combined with one or more be coated with several metal oxides. Mica belongs to the layered silicates. The most important representatives of these silicates are muscovite, phlogopite, paragonite, biotite, lepidolite and margarite. To produce the pearlescent pigments in conjunction with metal oxides, the mica, predominantly muscovite or phlogopite, is coated with a metal oxide.
  • synthetic mica coated with one or more metal oxides 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 metal oxides mentioned above.
  • the color of the respective pigments can be varied by varying the layer thickness of the metal oxide(s).
  • a process comprising the use of a colorant (F) which contains at least one inorganic pigment (F2), the inorganic pigment preferably being 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 colored pigments based on mica or mica, which are coated with at least one metal oxide and / or a metal oxychloride.
  • F2 which contains at least one inorganic pigment (F2)
  • the inorganic pigment preferably being 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 colored pigments based on mica or mica, which are coated with at least one metal oxide and / or a metal oxychloride.
  • a colorant (F) is characterized in that it contains at least one pigment (F2) which is selected from mica- or mica-based pigments which have been mixed with one or more metal oxides from the group consisting 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), chromium oxide (CI 77288) and / or iron blue (Ferric Ferrocyanide, Cl 77510) are coated.
  • F2 is selected from mica- or mica-based pigments which have been mixed with one or more metal oxides from the group consisting of titanium dioxide (CI 77891 ), black iron oxide (CI 77499), yellow iron oxide (CI 77492), red and/or brown iron oxide (CI 77491
  • color pigments are commercially available, for example, under the trade names Rona®, Colorona®, Xirona®, Dichrona® and Timiron® from Merck, Ariabel® and Unipure® from Sensient, Prestige® from Eckart Cosmetic Colors and Sunshine® available from Sunstar.
  • Colorona® examples of particularly preferred color pigments with the trade name Colorona® are:
  • color pigments with the trade name Xirona® are, for example:
  • the colorant (F) according to the invention can also contain one or more organic pigments.
  • the organic pigments according to the invention are correspondingly insoluble, organic dyes or colored varnishes, for example from the group of nitroso, nitro, azo, xanthene, anthraquinone, isoindolinone, isoindoline, quinacridone, perinone, perylene -, diketopyrrolopyorrole, indigo, thioindido, dioxazine and/or triarylmethane compounds can be selected.
  • organic pigments examples include 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 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 1 1725, 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 158 00 ,
  • a method comprising the use of a colorant (F) which contains at least one organic pigment (F2), the organic pigment preferably being selected from the group consisting of carmine, quinacridone, phthalocyanine, sorghum, and blue pigments 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, C1 15510, CI 45370, CI 71105, red pigments with the color index numbers CI 12085 , CI 12120, CI 12370, CI 12420,
  • the organic pigment can also be a colored varnish.
  • colored lacquer is understood to mean particles which comprise a layer of absorbed dyes, the unit consisting of particles and dye being insoluble under the above-mentioned conditions.
  • the particles can be, for example, inorganic substrates, which can be aluminum, silica, calcium borosilicate, calcium aluminum borosilicate or even aluminum.
  • Alizarin color varnish for example, can be used as a colored varnish.
  • pigments with a specific shape can also be used in the colorant (F).
  • a pigment based on a lamellar and/or a lenticular substrate plate can be used.
  • coloring based on a substrate plate which comprises a vacuum metallized pigment is also possible.
  • a method according to the invention can be characterized in that the colorant (F) also contains one or more coloring compounds from the group of pigments based on a lamellar substrate plate, pigments based on a lenticular substrate plate and vacuum metallized pigments.
  • a method which comprises the use of a colorant (F) which contains at least one pigment (F2) which is selected from the group of pigments based on a lamellar substrate plate, pigments based on a lenticular substrate plate and the Vacuum metallized pigments.
  • the substrate plates of this type have an average thickness of at most 50 nm, preferably less than 30 nm, particularly preferably at most 25 nm, for example at most 20 nm.
  • the average thickness of the substrate platelets is at least 1 nm, preferably at least 2.5 nm, particularly preferably at least 5 nm, for example at least 10 nm.
  • Preferred ranges for the thickness of the substrate platelets are 2.5 to 50 nm, 5 to 50 nm, 10 to 50nm; 2.5 to 30 nm, 5 to 30 nm, 10 to 30 nm; 2.5 to 25 nm, 5 to 25 nm, 10 to 25 nm, 2.5 to 20 nm, 5 to 20 nm and 10 to 20 nm.
  • Each substrate plate preferably has a thickness that is as uniform as possible.
  • the pigment Due to the small thickness of the substrate plates, the pigment has a particularly high hiding power.
  • the substrate plates have a monolithic structure.
  • monolithic means consisting of a single, closed unit without breaks, layers or inclusions, although structural changes can occur within the substrate plates.
  • the Substrate platelets are preferably constructed homogeneously, meaning that no concentration gradient occurs within the platelets.
  • the substrate plates do not have a layered structure and do not have any particles or particles distributed therein.
  • the size of the substrate plate can be tailored to the respective application, in particular the desired effect on the keratinous material.
  • the substrate platelets have an average largest diameter of approximately 2 to 200 pm, in particular approximately 5 to 100 pm.
  • the form factor (aspect ratio), expressed by the ratio of the average size to the average thickness, is at least 80, preferably at least 200, more preferably at least 500, particularly preferably more than 750.
  • the average size of the uncoated substrate plates is understood to be the d50 value of the uncoated substrate plates. Unless otherwise stated, the d50 value was determined using a Sympatec Heios device with Quixel wet dispersion. To prepare the sample, the sample to be examined was predispersed in isopropanol for a period of 3 minutes.
  • the substrate plates can be constructed from any material that can be formed into platelet form.
  • the substrate plates can be of natural origin or synthetically produced.
  • Materials from which the substrate plates can be constructed are, for example, metals and metal alloys, metal oxides, preferably aluminum oxide, inorganic compounds and minerals such as mica and (semi-)precious stones, as well as plastics.
  • the substrate plates are preferably made of metal (alloys).
  • metal suitable for metallic luster pigments can be considered as a metal.
  • metals include iron and steel, as well as all air- and water-resistant (semi-)metals such as platinum, zinc, chromium, molybdenum and silicon, as well as their alloys such as aluminum bronze and brass.
  • Preferred metals are aluminum, copper, silver and gold.
  • Preferred substrate plates are aluminum plates and brass plates, with substrate plates made of aluminum being particularly preferred.
  • Lamellar substrate plates are characterized by an irregularly structured edge and are also referred to as “cornflakes” due to their appearance.
  • pigments based on lamellar substrate plates Due to their irregular structure, pigments based on lamellar substrate plates produce a high proportion of scattered light.
  • the pigments on the base provide coverage lamellar substrate plates do not completely remove the existing color of a keratin material and, for example, effects analogous to natural graying can be achieved.
  • Vacuum metallized pigments can be obtained, for example, by releasing metals, metal alloys or metal oxides from appropriately coated films. They are characterized by a particularly small thickness of the substrate plates in the range of 5 to 50 nm and by a particularly smooth surface with increased reflectivity. Substrate plates which comprise a pigment metallized in a vacuum are also referred to as VMP substrate plates in the context of this application. VMP substrate plates made of aluminum can be obtained, for example, by releasing aluminum from metallized foils.
  • the substrate plates made of metal or metal alloy can be passivated, for example by anodizing (oxide layer) or chromating.
  • Uncoated lamellar, lenticular and/or VPM substrate plates especially those made of metal or metal alloy, reflect the incident light to a high degree and produce a light-dark flop, but no color impression.
  • a color impression can be created, for example, due to optical interference effects.
  • Such pigments can be based on at least once coated substrate plates. These show interference effects through the superimposition of differently refracted and reflected light rays.
  • preferred pigments are pigments based on a coated lamellar substrate plate.
  • the substrate plate preferably has at least one coating B made of a high-refractive index metal oxide with a coating thickness of at least 50 nm.
  • Suitable materials for coatings A, B and C are all substances that can be applied in a film-like and permanent manner to the substrate plates and, in the case of layers A and B, have the required optical properties.
  • a coating of part of the surface of the substrate platelets is sufficient to obtain a pigment with a shiny effect.
  • only the upper and/or lower side of the substrate plates can be coated, with the side surface(s) being left out.
  • the entire surface of the optionally passivated substrate plates, including the side surfaces is covered by coating B.
  • the substrate plates are therefore completely covered by coating B. This improves the optical properties of the pigment and increases the mechanical and chemical resilience of the pigments.
  • the coated substrate plates preferably each have only one coating A, B and, if present, C.
  • the coating B is made up of at least one high-refractive index metal oxide. Highly refractive materials have a refractive index of at least 1.9, preferably at least 2.0 and particularly preferably at least 2.4. Preferably, the coating B comprises at least 95% by weight, particularly preferably at least 99% by weight, of high-refractive index metal oxide(s).
  • the coating B has a thickness of at least 50 nm.
  • the thickness of coating B is not more than 400 nm, particularly preferably at most 300 nm.
  • High-refractive index metal oxides suitable for coating B are preferably selectively light-absorbing (i.e. colored) metal oxides, such as iron (l I l) oxide (a- and y-Fe2O3, red), cobalt (II) oxide (blue), chromium (III) oxide (green), titanium (III) oxide (blue, is usually present in a mixture with titanium oxynitrides and titanium nitrides) and vanadium (V) oxide (orange) and mixtures thereof. Colorless, high-index oxides such as titanium dioxide and/or zirconium oxide are also suitable.
  • colorless, high-index oxides such as titanium dioxide and/or zirconium oxide are also suitable.
  • Coating B can contain a selectively absorbing dye, preferably 0.001 to 5% by weight, particularly preferably 0.01 to 1% by weight, in each case based on the total amount of coating B.
  • Organic and inorganic dyes that are stable in are suitable have a metal oxide coating installed.
  • the coating A preferably has at least one low-refractive index metal oxide and/or metal oxide hydrate.
  • coating A comprises at least 95% by weight, particularly preferably at least 99% by weight, of low-refractive index metal oxide (hydrate).
  • Low-refractive materials have a refractive index of at most 1.8, preferably at most 1.6.
  • the low-refractive metal oxides that are suitable for coating A include, for example, silicon (di)oxide, silicon oxide hydrate, aluminum oxide, aluminum oxide hydrate, boron oxide, germanium oxide, manganese oxide, magnesium oxide and mixtures thereof, with silicon dioxide being preferred.
  • the coating A preferably has a thickness of 1 to 100 nm, particularly preferably 5 to 50 nm, particularly preferably 5 to 20 nm.
  • the distance between the surface of the substrate platelets and the inner surface of coating B is at most 100 nm, particularly preferably at most 50 nm, particularly preferably at most 20 nm. Because the thickness of coating A and thus the distance between the surface of the substrate platelets and Coating B is in the range specified above, it can be ensured that the pigments have high hiding power.
  • the pigment based on a lamellar substrate plate has only one layer A, it is preferred that the pigment has a lamellar substrate plate made of aluminum and a layer A made of silicon dioxide. If the pigment based on a lamellar substrate plate has a layer A and a layer B, it is preferred that the pigment has a lamellar substrate plate made of aluminum, a layer A made of silicon dioxide and a layer B made of iron oxide.
  • the pigments have a further coating C made of a metal oxide (hydrate), which is different from the underlying coating B.
  • Suitable metal oxides are, for example, silicon (di) oxide, silicon oxide hydrate, aluminum oxide, aluminum oxide hydrate, zinc oxide, tin oxide, titanium dioxide, zirconium oxide, iron (III) oxide and chromium (III) oxide. Silicon dioxide is preferred.
  • the coating C preferably has a thickness of 10 to 500 nm, particularly preferably 50 to 300 nm.
  • Layers A and C serve in particular as corrosion protection as well as chemical and physical stabilization.
  • Layers A and C particularly preferably contain silicon dioxide or aluminum oxide, which are applied using the sol-gel process.
  • This method includes dispersing the uncoated lamellar substrate platelets or the lamellar substrate platelets already coated with layer A and / or layer B in a solution of a metal alkoxide such as tetraethyl orthosilicate or aluminum triisopropanolate (usually in a solution of organic solvent or a mixture of organic solvent and water with at least 50% by weight organic solvent such as a C1 to C4 alcohol), and Addition of a weak base or acid to hydrolyze the metal alkoxide, forming a film of the metal oxide on the surface of the (coated) substrate wafers.
  • a metal alkoxide such as tetraethyl orthosilicate or aluminum triisopropanolate
  • Layer B can be produced, for example, by hydrolytic decomposition of one or more organic metal compounds and/or by precipitation of one or more dissolved metal salts and, if necessary, subsequent aftertreatment (for example, converting a formed hydroxide-containing layer into the oxide layers by annealing).
  • each of coatings A, B and/or C may be composed of a mixture of two or more metal oxides (hydrates), each of the coatings is preferably composed of a metal oxide (hydrate).
  • the pigments based on coated lamellar or lenticular substrate plates or the pigments based on coated VMP substrate plates preferably have a thickness of 70 to 500 nm, particularly preferably 100 to 400 nm, particularly preferably 150 to 320 nm, for example 180 to 290 nm, on. Due to the small thickness of the substrate plates, the pigment has a particularly high hiding power.
  • the low thickness of the coated substrate plates is achieved in particular by the fact that the thickness of the uncoated substrate plates is small, but also by setting the thicknesses of the coatings A and, if present, C to the smallest possible value.
  • the thickness of coating B determines the color impression of the pigment.
  • the adhesion and abrasion resistance of pigments based on coated substrate plates in the keratinous material can be significantly increased by additionally modifying the outermost layer, layer A, B or C depending on the structure, with organic compounds such as silanes, phosphoric acid esters, titanates, borates or carboxylic acids becomes.
  • the organic compounds are bound to the surface of the outermost layer A, B or C, preferably containing metal oxide.
  • the outermost layer refers to the layer that is spatially furthest away from the lamellar substrate plate.
  • the organic compounds are preferably functional silane compounds which can bind to the metal oxide-containing layer A, B or C. These can be either monofunctional or bifunctional compounds.
  • bifunctional organic compounds are methacryloxypropenyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-acryloxypropyltrimethoxysilane, 2-acryloxyethyltrimethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-acryloxypropyltrimethoxysilane, 2-methacryloxyethyltriethoxysilane, 2-acryloxyethyltriethoxysilane, 3-methacrylic oxypropyltris(methox-yethoxy)silane, 3-Methacryloxypropyltris(butoxyethoxy)silane, 3-Methacryloxypropyltris(propoxy)silane, 3-Methacryloxypropyltris(butoxy)silane, 3-Acryloxypropyltris(methoxyethoxy)silane, 3-Acryloxypropyltris(butoxyethoxy)silane
  • modification can be carried out with a monofunctional silane, in particular an alkylsilane or arylsilane.
  • This has only one functional group, which can covalently bind to the surface of pigment based on coated lamellar substrate plates (ie to the outermost metal oxide-containing layer) or, if the coverage is not completely complete, to the metal surface.
  • the hydrocarbon residue of the silane points away from the pigment. Depending on the type and nature of the hydrocarbon residue of the silane, a different degree of hydrophobicization of the pigment is achieved. Examples of such silanes are hexadecyltrimethoxysilane, propyltrimethoxysilane, etc.
  • surface-modifying pigments based on silicon dioxide-coated aluminum substrate plates with a monofunctional silane.
  • Octyltrimethoxysilane, octyltriethoxysilane, hecadecyltrimethoxysilane and hecadecyltriethoxysilane are particularly preferred.
  • the changed surface properties / hydrophobization can achieve an improvement in terms of adhesion, abrasion resistance and alignment in use.
  • Suitable pigments based on a lamellar substrate plate include, for example, the pigments from the VISIONAIRE series from Eckart.
  • Pigments based on a lenticular substrate plate are available, for example, under the name Alegrace® Spotify from Schlenk Metallic Pigments GmbH.
  • Pigments based on a substrate platelet which comprises a vacuum metallized pigment are available, for example, under the name Alegrace® Marvelous or Alegrace® Aurous from Schlenk Metallic Pigments GmbH.
  • the use of the aforementioned pigments in the colorant (F) of the process according to the invention is particularly preferred. Furthermore, it is preferred if the pigments used have a certain particle size. It is therefore advantageous according to the invention if the at least one pigment has an average particle size D50 of 1.0 to 50 pm, preferably from 5.0 to 45 pm, preferably from 10 to 40 pm, in particular from 14 to 30 pm.
  • the average particle size D50 can be determined, for example, using dynamic light scattering (DLS).
  • the pigment or pigments can preferably be used in an amount of 0.1 to 20.0% by weight, preferably 0.2 to 10.0% by weight, in each case based on the total weight of the colorant (F).
  • a method according to the invention is characterized in that the colorant (F) - based on the total weight of the colorant (F) - contains one or more pigments (F2) in a total amount of 0.1 to 20.0 wt. -%, preferably from 0.2 to 10.0% by weight.
  • Another essential feature of the colorant (F) is its maximum content of acrylate-based polymers, which - based on the total weight of the colorant (F) - must be less than 1.0% by weight. In other words, the colorant (F) is essentially free of acrylate-based polymers.
  • Acrylate-based polymers are understood to mean all polymers that were synthesized using acrylic acid, methacrylic acid, a derivative of acrylic acid and/or a derivative of methacrylic acid.
  • Acrylate-based polymers are therefore synthetically produced polymers whose synthesis uses a monomer whose structure is based on acrylic acid and/or methacrylic acid.
  • Acrylic acid, methacrylic acid and/or their salts can be used in the synthesis.
  • Corresponding derivatives of acrylic acid can be, for example, acrylic acid esters or acrylic acid amides.
  • Derivatives of methacrylic acid can be, for example, methacrylic acid esters or methacrylic acid amides.
  • acrylate-based polymers are mentioned below. According to the invention, all of these polymers are not used or are not used in significant amounts in the colorant (F).
  • Acrylate-based polymers are, for example, homopolymers of acrylic acid, copolymers of acrylic acid, homopolymers of methacrylic acid, copolymers of methacrylic acid, the homopolymers or copolymers of acrylic acid esters, the homopolymers or copolymers of methacrylic acid esters, the homopolymers or copolymers of acrylic acid amides , the homopolymers or copolymers of methacrylic acid amides.
  • acrylate-based polymers include, for example, homo- or copolymers of isooctyl (meth)acrylate; isononyl (meth)acrylate; 2-ethylhexyl (meth)acrylate; Lauryl (meth)acrylate; isopentyl (meth)acrylate; n-Butyl (meth)acrylate); isobutyl (meth)acrylate; ethyl (meth)acrylate; methyl (meth)acrylate; tert-butyl (meth)acrylate; stearyl (meth)acrylate; hydroxyethyl (meth)acrylate; 2-hydroxypropyl (methacrylate; 3-hydroxypropyl (meth)acrylate and/or mixtures thereof.
  • acrylate-based polymers include, for example, copolymers of ethyl acrylate and maleic anhydride, methyl acrylate and maleic anhydride, ethyl (meth) acrylate and maleic anhydride and methyl (meth) acrylate and maleic anhydride.
  • acrylate-based polymers can be selected from the homo- or copolymers of (meth)acrylamide; N-alkyl (meth)acrylamides, especially those with C2-C18 alkyl groups, such as N-ethyl acrylamide, N-tert-butyl acrylamide, le N-octyl acrylamide; N-Di(C1-C4)alkyl-(meth)acrylamide.
  • Acrylate-based polymers available on the market include, for example, Aculyn® 33, Aculyn® 22 (Acrylates/Steareth-20 Methacrylate Copolymer), Aculyn® 28 (Acrylates/Beheneth-25 Methacrylate Copolymer), Structure 2001® (Acrylates/ Steareth-20 Itaconate Copolymer), Structure 3001® (Acrylates/Ceteth-20 Itaconate Copolymer), Structure Plus® (Acrylates/Aminoacrylates C10-30 Alkyl PEG-20 Itaconate Copolymer), Carbopol® 1342, 1382, Ultrez 20, Ultrez 21 ( Acrylates/C10-30 Alkyl Acrylate Crosspolymer), Synthalen W 2000® (Acrylates/Palmeth-25 Acrylate Copolymer) or the Soltex OPT (Acrylates/C 12-22 Alkyl methacrylate Copolymer) sold by Rohme and Haas.
  • acrylate-based polymers include the copolymers octylacrylamide/acrylates/butylamino-ethyl-methacrylate copolymer, such as those sold commercially by NATIONAL STARCH under the trade names AMPHOMER® or LOVOCRYL® 47, or the copolymers of acrylates/octylacrylamide which are sold under the trade names DERMACRYL® LT and DERMACRYL® 79 are distributed by NATIONAL STARCH.
  • the coloring agent which additionally contained significant amounts of acrylic acid-based polymers (F3), did not produce uniform and, in particular, no resistant films on keratin material together with the ingredients (F1) and (F2). trained.
  • the dyes which in addition to (F1) and (F2) also contained acrylate-based polymers (F3), formed very brittle or soft films that did not adhere sufficiently to the keratin material when the hair was subsequently washed.
  • the acrylic acid-based polymers (F3) interact too strongly with the organic amines (F1). This interaction was particularly evident when a C 1 -C 6 alkoxysilane (or its condensation product) and/or an amino-functionalized silicone polymer was used as the organic amine (F1).
  • acrylate-based polymers (F3) it has proven to be essential that the content of acrylate-based polymers (F3) remains below the maximum amount of 1.0% by weight. It is particularly preferred to reduce this content even further and, in the best case, to completely dispense with the use of acrylate-based polymers.
  • a method according to the invention is therefore characterized in that the total amount of acrylate-based polymers (F3) contained in the colorant (F) - based on the total weight of the colorant (F) - is below 0.8 % by weight, preferably below 0.5% by weight, more preferably below 0.1% by weight and particularly preferably 0% by weight.
  • a method according to the invention is therefore characterized in that the colorant (F) is free of acrylate-based polymers (F3).
  • the formation of resistant and resilient films on the keratin material could be further supported if at least one solvent (F4) other than water was used in the dye (F).
  • solvent is a fixed term used in chemistry to describe a substance that is liquid at room temperature (20 °C) and that is capable of dissolving other chemical substances.
  • the solvent or solvents (F4) ensure a fine dispersion of the pigments (F2) and ensure a homogeneous mixing of the pigments (F2) with the organic amino compounds (F1).
  • the addition of at least one solvent also increases the storage stability of the colorant (F). If the solvent (F4) evaporates after application, this ensures subsequent hardening of the film.
  • Suitable solvents include, for example, the compounds from the group
  • Ethanol isopropanol, polyethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, ethylene glycol, 1,2-butylene glycol, dipropylene glycol, diethylene glycol monoethyl ether, glycerin, phenoxyethanol, benzyl alcohol, poly-C 1 -C 6 --alkylene glycols, dimethyl carbonate, diethyl carbonate , ethylene carbonate, propylene carbonate, butylene carbonate and glycerol carbonate.
  • a method according to the invention is characterized in that the colorant (F) contains at least one solvent (F4) which is selected from the group consisting of ethanol, isopropanol, 1,2-propylene glycol, 1,3-propylene glycol, ethylene glycol, 1,2-butylene glycol, dipropylene glycol, diethylene glycol monoethyl ether, glycerin, phenoxyethanol, benzyl alcohol, poly-C 1 -C 6 --alkylene glycols, dimethyl carbonate, diethyl carbonate, ethylene carbonate, propylene carbonate , butylene carbonate and glycerol carbonate, preferably from the group consisting of ethanol, isopropanol and polyethylene glycol.
  • solvent F4 which is selected from the group consisting of ethanol, isopropanol, 1,2-propylene glycol, 1,3-propylene glycol, ethylene glycol, 1,2-butylene glycol, dipropylene glycol, diethylene glycol mono
  • a method according to the invention is characterized in that the colorant (F) contains at least one solvent (F4) other than water, which is selected from the group consisting of ethanol and isopropanol.
  • Ethanol has the CAS number. 64-17-5.
  • Isopropanol is alternatively known as 2-propanol and has the CAS number.
  • 1,2-Propylene glycol is alternatively referred to as 1,2-propanediol and has the CAS numbers 57-55-6 [(RS)-1,2-dihydroxypropane], 4254-14-2 [(R)-1 ,2-dihydroxypropane] and 4254-153 [(S)-1,2-dihydroxypropane]
  • 1,3-propylene glycol is also alternatively referred to as 1,3-dihydroxypropane or 1,3-propanediol and has the CAS number. 504-63-2.
  • Ethylene glycol is alternatively known as 1,2-ethanediol and has the CAS number. 107-21-1.
  • 1,2-Butylene glycol can also be referred to as 1,2-butanediol and has the CAS numbers 584-03-2 (racemate), 40348-66-1 ((R)-enantiomer) and 73522-17-5 (( S)-enantiomer).
  • the dipropylene glycols form a group of substances that are derived from the glycol ether.
  • the group of dipropylene glycols includes 2, 2'-oxydi-1-propanol with the CAS number. 108-61-2, 1,1 '-oxide i-2-propanol with the CAS no. 110-98-5 and 2-(2-Hydroxypropoxy)-1-propanol with CAS no. 106-62-7.
  • the mixture of these three isomers has the CAS number. 25265-71-8.
  • Diethylene glycol monoethyl ether can alternatively be referred to as ethoxydiglycol or as ethyldiglycol or as 2-(2-ethoxyethoxy)ethanol) and has the CAS number. 111-90-0.
  • Glycerol is also alternatively known as 1,2,3-propane triol and has the CAS number 56-81-5. Phenoxyethanol has the CAS number 122-99-6.
  • Benzyl alcohol can alternatively be referred to as phenylmethanol and has the CAS number. 100-51-6.
  • Suitable poly-C 1 -C 6 alkylene glycols include in particular the polyethylene glycols, as described, for example, by the formula (AG). HO — CH 2 — CH 2 -0 - H
  • x represents an integer from 1 to 1000, preferably 1 to 100, particularly preferably 2 to 50.
  • the alkylene glycols of the formula (AG) are protic substances with at least one hydroxy group, which can also be referred to as polyethylene glycols due to their repeating unit -CH2-CH2-O-, provided x is a value of at least 2.
  • x represents an integer from 1 to 10,000.
  • Polyethylene glycols with a molecular mass between 200 g/mol and 400 g/mol are non-volatile liquids at room temperature.
  • PEG 600 has a melting range of 17 to 22 °C and therefore has a paste-like consistency. With molecular masses over 3000 g/mol, PEGs are solid substances and are marketed as flakes or powder.
  • a particularly preferred low molecular weight polyethylene glycol is, for example, PEG-8.
  • PEG-8 is alternatively referred to as PEG 400 and is commercially available, for example, from APS.
  • polyethylene glycols are, for example, PEG-6, PEG-7, PEG-9 and PEG-10.
  • PEG-32 is alternatively referred to as PEG 1500 and can be purchased commercially from Clariant, for example.
  • Dimethyl carbonate is alternatively known as carbonic acid dimethyl ester and has the CAS number 616-38-6.
  • Diethyl carbonate is alternatively known as carbonic acid diethyl ester and has the CAS number. 105-58-8.
  • Ethylene carbonate is also known as 1,3-dioxolan-2-one.
  • Ethylene carbonate corresponds to the compound of formula (I) in which R1 and R2 are hydrogen and n is the number 0.
  • Ethylene carbonate has the CAS number 96-49-1.
  • Propylene carbonate is alternatively known as 4-methyl-1,3-dioxolan-2-one.
  • Propylene carbonate corresponds to the compound of formula (I) in which R1 represents a methyl group, R2 represents hydrogen and n represents the number 0.
  • Propylene carbonate has the CAS numbers 108-32-7 [(RS)-4-methyl-1,3-dioxolan-2-one], 51260-39-0 [(S)-4-methyl-1,3-dioxolane -2-one] and 16606-55-6 [(R)-4-methyl-1,3-dioxolan-2-one], All of the aforementioned stereoisomers are included in the invention.
  • butylene carbonate is understood to mean 1,2-butylene carbonate, which is also alternatively referred to as 4-ethyl-1,3-dioxolan-2-one and which has the CAS number 4437-85-8.
  • Butylene carbonate corresponds to the compound of formula (I) in which R1 represents an ethyl group, R2 represents a hydrogen atom and n represents the number 0.
  • Glycerol carbonate is alternatively known as 4-hydroxymethyl-1,3-dioxolan-2-one and has the CAS number 931-40-8. Glycerol carbonate corresponds to the compound of formula (I) in which R1 represents a hydroxymethyl group, R2 represents a hydrogen atom and n represents the number 0.
  • the solvent or solvents (F4) represent the cosmetic carrier of the agent and are therefore preferably used as the main component in the colorant (F).
  • the main ingredient is an ingredient whose amount used exceeds that of all other ingredients.
  • the colorant (F) - based on the total weight of the colorant (F) - can contain one or more solvents (F4) other than water in a total amount of 20 to 95% by weight, preferably 30 to 85% by weight. %, more preferably from 40 to 80% by weight and very particularly preferably from 45 to 75% by weight.
  • a method according to the invention is characterized in that the colorant (F) - based on the total weight of the colorant (F) - contains one or more solvents (F4) other than water in a total amount of 20 to 95 weight. -%, preferably from 30 to 85% by weight, more preferably from 40 to 80% by weight and most preferably from 45 to 75% by weight.
  • the colorant (F) can optionally also contain other ingredients.
  • the colorant (F) can also contain other active ingredients, auxiliaries and additives, such as cationic, nonionic, amphoteric, zwitterionic and/or anionic surfactants, thickening and/or film-forming polymers that are not acrylate-based, structurants such as glucose, maleic acid and lactic acid, hair conditioning compounds such as phospholipids, for example lecitin and cephalins; perfume oils, dimethyl isosorbide and cyclodextrins; active ingredients that improve fiber structure, in particular mono-, di- and oligosaccharides such as glucose, galactose, fructose, fructose and lactose; dyes for coloring the product; Anti-dandruff active ingredients such as Piroctone Olamine, Zinc Omadine and Climbazol; amino acids and oligopeptides; Animal and/or plant-based protein hydrolysates, as well as in the form of their fatty acid condensation products or optionally anionically or cationically modified
  • the specialist will select these other substances based on the desired properties of the products.
  • additional active ingredients and auxiliary substances are preferably used in the preparations according to the invention in amounts of 0.0001 to 25% by weight, in particular 0.0005 to 15% by weight, based on the total weight of the respective agent.
  • the keratin material can be applied to the keratin material, for example with a gloved hand and/or with the aid of a brush or an applicette.
  • the exposure time of the colorant (F) can be 30 seconds to 45 minutes, preferably 45 seconds to 20 minutes, particularly preferably 1 to 10 minutes.
  • the colorant (F) is rinsed out after this exposure time.
  • the keratin material can then be dried either in air or under the influence of heat, for example with the help of a heat cap or a hairdryer.
  • the dye (F) can also be designed as a leave-on product, so that the dye remains on the keratin material after use and dries there - for example by evaporating the solvent (F4).
  • the colorant can remain on the keratin material.
  • the method according to the invention can optionally also include one or more further steps. Steps (1) and (2) preferably take place directly one after the other, without any further agent other than the colorant (F) being applied between these steps.
  • the keratin material can also be treated with a pretreatment agent before or after treatment with the colorant (F), which can be, for example, a shampoo or an emulsion or a gel for deep cleaning of the keratin material.
  • a pretreatment agent for example, a shampoo or an emulsion or a gel for deep cleaning of the keratin material.
  • an after-treatment agent such as a conditioner can optionally be used.
  • the pretreatment agent (V) preferably contains - based on the total weight of the pretreatment agent (V) - less than 1.0% by weight, preferably less than 0.1% by weight and particularly preferably 0% by weight of acrylate-based polymers.
  • the after-treatment agent (N) preferably contains - based on the total weight of the after-treatment agent (N) - less than 1.0% by weight. %, preferably less than 0.1% by weight and particularly preferably 0% by weight, of acrylate-based polymers.
  • a method according to the invention is characterized in that the keratin material, preferably human hair,
  • the pretreatment agent (V) - Before the treatment with the colorant (F), it is treated with a pretreatment agent (V), the pretreatment agent (V) - based on the total weight of the pretreatment agent (V) - being less than 1.0% by weight, preferably less than 0 .1% by weight and particularly preferably 0% by weight of acrylate-based polymers, and/or
  • the aftertreatment agent (N) - After the treatment with the colorant (F), it is treated with an aftertreatment agent (N), the aftertreatment agent (N) - based on the total weight of the aftertreatment agent (N) - being less than 1.0% by weight, preferably less than 0 .1% by weight and particularly preferably 0% by weight of acrylate-based polymers.
  • the acrylate-based polymers were the compounds already defined above and listed as examples.
  • the synthesis of the blend (I) was carried out in a four-neck round bottom flask equipped with a thermometer, dropping funnel, stirrer and reflux condenser. The heating took place via an oil bath. The synthesis was carried out under an argon atmosphere. 23.5 g of ethanol (absolute) and 47.1 g of methyltriethoxysilane were mixed with stirring in a 500 ml round-bottom flask. This mixture was heated to 50 °C with continued stirring. Then 5.9 g of a 1% solution of sulfuric acid in water was added over a period of about 1 minute. This resulted in a temperature increase to around 70 °C, with the temperature falling back to 50 °C after some time. Stirring was continued for another 10 minutes.
  • silane blend (I) produced in this way was incorporated into the following colorant (Fl) (all information in% by weight unless otherwise stated):
  • Hair strands (Kerling 9-0) were measured colorimetrically using a Datacolor color measuring device, type Spectraflash 450. The hair strands were then treated with plasma for 30 seconds or 60 seconds.
  • the Plasma Care® device from Terraplasma Medical GmbH was placed on the strand of hair and switched on for the above-mentioned period of time.
  • the strands that were to be treated with the plasma in wet form were completely wetted with water shortly before the treatment and dried with a towel so that they were towel-damp.
  • the strands were colored with the dye Fl. To do this, the dye was applied to the strands and left to act for 1 minute. The strand of hair was then washed thoroughly with water (1 minute) and dried.
  • strands of hair were measured colorimetrically using the Datacolor color measuring device, type Spectraflash 450, and then, without treatment with plasma, dyed with the dye Fl according to the above-mentioned method.
  • a commercially available shampoo (0.25 g of shampoo (Schauma 7 herbs) per 1 g of hair) was applied to the strands of each dyed hair wash and massaged in with the fingers for 30 seconds. The shampoo was then rinsed out for 1 minute under running, lukewarm water and the strand of hair was dried. The process described above corresponds to washing your hair. The process was repeated for each subsequent hair wash. After the appropriate number of hair washes, the strands were measured again with the above-mentioned color measuring device.
  • dE [ (Li - Lo) 2 + (ai - ao) 2 + (bi - bo )] 1/2
  • Li, ai and bi measurements of the hair strand after treatment
  • dL [(Li - Lo) 2 ] 172
  • the plasma treatment made it possible to improve the washing fastness of the dye Fl.
  • the synthesis of the silane blend (II) was carried out in a four-neck round bottom flask with a thermometer, dropping funnel, stirrer and reflux condenser. The heating took place via an oil bath. The synthesis was carried out under an argon atmosphere. A 500ml four-neck round bottom flask was purged with argon. Then 59.7 g of methyltriethoxysilane and 29.9 g of (3-aminopropyl)triethoxysilane were weighed into a flask. The flask was inserted into the apparatus and continuously flushed with argon during the synthesis. The reaction mixture was stirred at 250 rpm and heated to 50°C.
  • silane blend (II) produced in this way was incorporated into the following colorant (Fll) (all data in% by weight unless otherwise stated):
  • the plasma treatment made it possible to improve the washing fastness of the FH dye.

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Abstract

La présente invention concerne un procédé de coloration d'une matière kératinique, en particulier des cheveux humains, comprenant les étapes suivantes consistant à : (1) traiter la matière kératinique à l'aide d'un plasma et (2) traiter la matière kératinique à l'aide d'un colorant (F), le colorant (F) contenant, sur la base du poids total du colorant (F) : (F1) au moins un composé amino organique, (F2) au moins un pigment et (F3) moins de 1,0 % en poids de polymères à base d'acrylate.
PCT/EP2023/064375 2022-07-28 2023-05-30 Procédé de coloration d'une matière kératinique, comprenant le procédé de traitement de la matière kératinique à l'aide d'un plasma et de l'utilisation d'un colorant WO2024022647A1 (fr)

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DE102022207784.9A DE102022207784A1 (de) 2022-07-28 2022-07-28 Verfahren zum Färben von keratinischem Material, umfassend die Behandlung des Keratinmaterials mit Plasma und die Anwendung eines Färbemittels

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20150107616A1 (en) * 2012-03-22 2015-04-23 Ariel-University Research And Development Company, Ltd. Methods for processing keratinous fibers, and uses thereof
DE102018209735A1 (de) 2018-06-15 2019-12-19 Terraplasma Gmbh Plasmaeinrichtung zur Behandlung von Körperoberflächen
WO2020254009A1 (fr) * 2019-06-19 2020-12-24 Henkel Ag & Co. Kgaa Procédé de coloration d'une matière kératinique
WO2020260619A1 (fr) * 2019-06-28 2020-12-30 L'oreal Méthode de coloration de fibres kératiniques comprenant une étape de traitement par plasma froid desdites fibres
US20210401713A1 (en) * 2020-06-30 2021-12-30 Hfc Prestige Service Germany Gmbh Method for coating keratin fibers

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20150107616A1 (en) * 2012-03-22 2015-04-23 Ariel-University Research And Development Company, Ltd. Methods for processing keratinous fibers, and uses thereof
DE102018209735A1 (de) 2018-06-15 2019-12-19 Terraplasma Gmbh Plasmaeinrichtung zur Behandlung von Körperoberflächen
WO2020254009A1 (fr) * 2019-06-19 2020-12-24 Henkel Ag & Co. Kgaa Procédé de coloration d'une matière kératinique
WO2020260619A1 (fr) * 2019-06-28 2020-12-30 L'oreal Méthode de coloration de fibres kératiniques comprenant une étape de traitement par plasma froid desdites fibres
US20210401713A1 (en) * 2020-06-30 2021-12-30 Hfc Prestige Service Germany Gmbh Method for coating keratin fibers

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