EP4288156A1 - Agent de coloration de matières kératiniques, contenant au moins deux composés organosiliciés différents l'un de l'autre, au moins un pigment et au moins un composant gras liquide et/ou un solvant - Google Patents

Agent de coloration de matières kératiniques, contenant au moins deux composés organosiliciés différents l'un de l'autre, au moins un pigment et au moins un composant gras liquide et/ou un solvant

Info

Publication number
EP4288156A1
EP4288156A1 EP22701884.3A EP22701884A EP4288156A1 EP 4288156 A1 EP4288156 A1 EP 4288156A1 EP 22701884 A EP22701884 A EP 22701884A EP 4288156 A1 EP4288156 A1 EP 4288156A1
Authority
EP
European Patent Office
Prior art keywords
group
agent
weight
organic silicon
integer
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.)
Pending
Application number
EP22701884.3A
Other languages
German (de)
English (en)
Inventor
Phillip Jaiser
Torsten LECHNER
Juergen Schoepgens
Marc NOWOTTNY
Carsten MATHIASZYK
Andreas Walter
Carolin Kruppa
Avni TAIRI
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 EP4288156A1 publication Critical patent/EP4288156A1/fr
Pending 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
    • 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
    • A61K8/345—Alcohols containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61K2800/80—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

  • composition for coloring keratinic material containing at least two different organic silicon compounds, at least one pigment and at least one liquid fatty component and/or a solvent
  • the present application relates to an agent for coloring keratinic material, in particular human hair, which contains at least two different organic silicon compounds, at least one pigment and at least one liquid fat component and/or a solvent.
  • a second subject of this application is a method for dyeing keratinic material, in particular human hair, in which the hair is first moistened and then the agent of the first subject of the invention is applied to the moistened hair.
  • Oxidation colorants are usually used for permanent, intensive colorations with good fastness properties and good gray coverage. Such colorants 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 coloring agents are characterized by very long-lasting coloring results.
  • color pigments are generally understood to mean insoluble, color-imparting substances. These are present in undissolved form in the form of small particles in the coloring formulation and are only deposited from the outside on the hair fibers and/or the surface of the skin. Therefore, they can usually be cleaned with a few washes with detergents containing surfactants remove without residue.
  • Various products of this type are available on the market under the name of hair mascara.
  • EP 2168633 B1 deals with the task of producing long-lasting hair coloring using pigments.
  • the document teaches that when using a combination of pigment, organic silicon compound, hydrophobic polymer and a solvent, colorations can be produced on hair which are said to be particularly resistant to shampooing.
  • 3-aminopropyltriethoxysilane was used as the organic silicon compound.
  • organosilicon compounds from the group of silanes are used, the molecular structure of these silanes comprising at least one hydroxyl group and/or hydrolyzable group. Due to the presence of the hydroxyl groups or hydrolyzable groups, the silanes are reactive substances which hydrolyze or oligomerize or polymerize in the presence of water. The oligomerization or polymerization of the silanes initiated by the presence of water ultimately leads to the formation of a film when used on the keratin material, which fixes the color-providing compounds and in this way produces very long-lasting colorations.
  • the object of the present invention to provide a dyeing system which has fastness properties comparable to oxidative dyeing.
  • the fastness to washing and the fastness to rubbing should be outstanding, but the use of the oxidation dye precursors otherwise customarily used for this purpose should be avoided.
  • a technology was sought that would allow the pigments known from the prior art to be fixed to the hair in an extremely permanent manner.
  • the production the coloring agent should be inexpensive, and the agents themselves should have very good storage stability. When using the agents in a dyeing process, consistently good color results should be achievable, regardless of the conditions prevailing during production and use (such as humidity and temperature).
  • application should be as uncomplicated as possible, so that the user can apply the colorant to the hair quickly and in a targeted manner without having to mix and homogenize different formulations beforehand.
  • keratinic materials in particular hair, are colored with an agent which contains at least two different hydrolyzable organic silicon compounds (a), at least one pigment (b) and also at least one contains a fat component that is liquid at 20 °C and/or an organic solvent (c).
  • a first subject matter of the present invention is a composition for coloring keratin material, in particular human hair
  • each organosilicon compound being independently selected from the group of silanes having one, two or three silicon atoms, the organosilicon compound having one or more hydroxyl groups and/or hydrolyzable groups per molecule includes,
  • Keratinic material means hair, skin, nails (such as fingernails and/or toenails). Wool, fur and feathers also fall under the definition of keratin material.
  • Keratinic material is preferably understood to mean human hair, human skin and human nails, in particular fingernails and toenails. Very particularly preferably, keratin material is understood as meaning human hair.
  • the agent according to the invention for coloring keratinic material contains the essential components (a), (b) and (c), the color effect being achieved by the pigments or color pigments (b) contained in the agent.
  • the term “coloring agent” is used in the context of this invention for coloring the keratin material, in particular the hair, caused by the use of pigments. With this coloring, the aforementioned pigments are deposited in a particularly homogeneous and smooth film on the surface of the keratin material. The film is formed in situ by oligomerization or polymerization of the organic silicon compound or compounds, and by the interaction of the organic silicon compound with the pigment or pigments.
  • the agent according to the invention can be formulated as a concentrate, so that the components (a), (b) and (c) represent the quantitative main components of the agent.
  • the main component is an ingredient whose quantity used exceeds that of all other ingredients.
  • the agent can also contain the components (a), (b) and (c) in a cosmetic carrier which can contain water, contain little water or be anhydrous.
  • a cosmetic carrier can be liquid, gel-like, creamy, powdery or solid (e.g. in the form of a tablet or a pellet).
  • such carriers are, for example, creams, emulsions, gels or foaming solutions containing surfactants, such as shampoos, foam aerosols, foam formulations or other preparations, in particular concentrates, which are suitable for use on keratin material or the hair.
  • At least two different organic silicon compounds (a)
  • agent (a) contains at least two different organic silicon compounds.
  • Each of these organic silicon compounds is selected from silanes having one, two or three silicon atoms, the organic silicon compound comprising one or more hydroxyl groups and/or hydrolyzable groups per molecule.
  • each silane is selected independently of the other silane from the group of silanes having one, two or three silicon atoms.
  • Each of the two organic silicon compounds selected comprises one or more hydroxyl groups and/or hydrolyzable groups per molecule.
  • each of the three silanes is selected independently of the other two silanes from the group of silanes having one, two or three silicon atoms.
  • Each of the three silanes includes one or more hydroxyl groups and/or hydrolyzable groups per molecule.
  • the organic silicon compounds or organic silanes contained in agent (a) are reactive compounds.
  • Organic silicon compounds are compounds that either have a direct silicon-carbon bond (Si-C) or in which the carbon is bonded to the silicon via an oxygen, nitrogen, or sulfur atom. atom is linked.
  • the organic silicon compounds of the present invention are compounds containing one to three silicon atoms.
  • the organic silicon compounds particularly preferably contain one or two silicon atoms.
  • silane stands for a group of chemical compounds based on a silicon backbone and hydrogen.
  • organic silanes some or all of the hydrogen atoms are 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.
  • Agent (a) contains at least two different organic silicon compounds each selected from silanes having one, two or three silicon atoms, each organic silicon compound comprising one or more hydroxyl groups or hydrolyzable groups per molecule.
  • Different organic silicon compounds mean two substances whose molecular structure is different from each other.
  • an agent according to the invention is characterized in that it contains at least one first organic silicon compound (a1) selected from silanes having one, two or three silicon atoms, the organic silicon compound also having one or more basic chemical functions and one or more hydroxyl groups or hydrolyzable groups per molecule.
  • a1 selected from silanes having one, two or three silicon atoms, the organic silicon compound also having 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, an 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-Ce-alkylamino group or a di(Ci-C6)-alkylamino group.
  • the hydrolyzable group or groups is preferably a Ci-Ce-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, then the organic Silicon compound prefers 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.
  • a very particularly preferred agent according to the invention is characterized in that it contains at least one first organic silicon compound (a1) selected from silanes having 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 hydrolyzable groups per molecule.
  • a1 selected from silanes having 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 hydrolyzable groups per molecule.
  • the agent according to the invention contains at least one first organic silicon compound (a1) of the formula (I) and/or (II).
  • the compounds of formulas (I) and (II) are organic silicon compounds selected from silanes having one, two or three silicon atoms, the organic silicon compound comprising one or more hydroxyl groups and/or hydrolyzable groups per molecule.
  • an agent according to the invention is characterized in that it contains at least one first organic silicon compound (a1) of the formula (I) and/or (II).
  • R2 independently represent a hydrogen atom or a Ci-Ce-alkyl group
  • - L is a linear or branched, divalent Ci-C2o-alkylene group
  • R3, R4 independently represent a Ci-Ce-alkyl group
  • R5, R5', R5", R6, R6' and R6" independently represent a Ci-Ce-alkyl group
  • - A, A', A", A"' and A"" independently represent a linear or branched, divalent Ci-C2o-alkylene group
  • - R 7 and R 8 independently represent a hydrogen atom, a C 1 -C 6 alkyl group, a hydroxy-C1-C6-alkyl group, a C2-C6-alkenyl group, an amino-C1-C6-alkyl group or a group of formula (III) - (A'''')-Si(R 6 '') d ''(OR 5 '') c '' (III), - c, represents an integer from 1 to 3 , - d is the integer 3 - c, - c' is an integer from 1 to 3, - d' is the integer 3 - c', - c'' is an integer from 1 to 3 stands, - d'' stands for the integer 3 – c', - e stands for 0 or 1,
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 5 ', R 5 '', R 6 , R 6 ', R 6 '', R 7 , R 8 , L, A, A' , A'', A''' and A'''' in the compounds of formula (I) and (II) are exemplified below:
  • Examples of a C1-C6 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 C2-C6-alkenyl group are vinyl, allyl, but- 2 -enyl, but- 3 -enyl and isobutenyl, preferred C2-C6-alkenyl radicals are vinyl and allyl.
  • Preferred examples of a hydroxy-C1-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-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 bivalent C1-C20-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 also be branched.
  • C3-C20 branched divalent alkylene groups are ( -CH2 -CH(CH3)-) and ( -CH2 -CH(CH3) -CH2- ) .
  • the radicals R 1 and R 2 independently represent a hydrogen atom or a C 1 -C 6 - alkyl group.
  • the radicals R 1 and R 2 are very particularly preferably both hydrogen atoms.
  • the 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- is a linear divalent C 1 -C 6 alkylene group.
  • -L- is particularly preferably 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 - CH2 - CH2 - CH2- ).
  • L is very particularly preferably a propylene group (-CH 2 -CH 2 -CH 2 -).
  • the organic silicon compounds of the formula (I) R 1 R 2 NL—Si(OR 3 )a(R 4 )b (I) according to the invention each carry the silicon-containing group —Si(OR 3 )a(R 4 )b at one end .
  • the group R 3 represents a hydrogen atom or a C 1 -C 6 alkyl group and the group R 4 represents a C 1 -C 6 alkyl group.
  • R3 and R4 are particularly preferably, independently of one another, a methyl group or an ethyl group.
  • a represents an integer from 1 to 3, and b represents 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.
  • Dyeings with the best fastness to washing could be obtained if 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 detergent 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 radical b stands for 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 -R 3 , R 4 independently represent a methyl group or an ethyl group and - a represents the number 3 and - 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), R 1 R 2 NL-Si(OR 3 ) a (R 4 ) b (I), where - R 1 , R 2 both stand for a hydrogen atom, and - L for a linear, divalent C 1 -C 6 -alkylene group, preferably for a propylene group (-CH 2 -CH 2 -CH 2 -) or for an ethylene group ( -CH 2 -CH 2 -), - R3, R4 independently represent a methyl group or an ethyl group and - a represents the number 3 and - b represents the number 0.
  • Organic silicon compounds of the formula (I) which are particularly suitable for solving the problem of the invention are --(3-aminopropyl)triethoxysilane - (3-aminopropyl)trimethoxysilane -1-(3-aminopropyl)silanetriol - (2-aminoethyl)triethoxysilane - (2-aminoethyl)trimethoxysilane - (3-dimethylaminopropyl)triethoxysilane -(3-dimethylaminopropyl)trimethoxysilane -1-(3-dimethylaminopropyl)silanetriol - (2-dimethylaminoethyl)triethoxysilane.
  • an agent according to the invention is characterized in that it contains at least one first organic silicon compound (a1) of the formula (I) which is selected from the group consisting of - (3-aminopropyl)triethoxysilane - (3-aminopropyl )trimethoxysilane -1-(3-aminopropyl)silanetriol - (2-aminoethyl)triethoxysilane - (2-aminoethyl)trimethoxysilane -1-(2-aminoethyl)silanetriol - (3-dimethylaminopropyl)triethoxysilane - (3-dimethylaminopropyl)trimethoxysilane -1-(3-dimethylaminopropyl)silanetriol - (2- dimethylaminoethyl)tri
  • an agent according to the invention is characterized in that it contains at least one first organic silicon compound (a1) of the formula (I) 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)trimethoxysilane - (3-dimethylaminopropyl)triethoxysilane - (2-dimethylaminoethyl)trimethoxysilane and/or - (2-dimethylaminoethyl)triethoxy
  • organic silicon compounds of the formula (I) are commercially available.
  • (3-aminopropyl)trimethoxysilane is commercially available from Sigma-Aldrich.
  • (3-Aminopropyl)triethoxysilane is also commercially available from Sigma-Aldrich.
  • the agent according to the invention contains at least one organic silicon compound of the formula (II) (R 5 O) c (R 6 ) d Si-(A) e -[NR 7 -(A')] f -[O- (A'')] g -[NR 8 -(A''')] h -Si(R 6 ') d' (OR 5 ') c' (II).
  • the organosilicon compounds of the formula (II) according to the invention carry the silicon-containing groups (R 5 O)c(R 6 )dSi- and -Si(R 6')d'(OR 5')c' at both of their 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.
  • an inventive contains organic Silicon compound of the formula (II) at least one group from the group consisting of -(A)- and -[NR7-(A')]- and -[O-(A'')]- and -[NR8-(A''')]-.
  • the radicals R 5 , R 5 ', R 5 '' are independently of one another a hydrogen atom or a C 1 -C 6 alkyl group.
  • the radicals R 6 , R 6 'and R 6 '' independently represent a C 1 -C 6 -alkyl group.
  • c represents an integer from 1 to 3, and d represents the integer 3 - c. If c is the number 3, then d is 0. If c is the number 2, then d is 1. If c is the number 1, then d is 2.
  • c' is an integer from 1 to 3, and d' represents the integer 3 - c'. If c' is the number 3, then d' is 0. If c' is the number 2, then d' is 1. If c' is the number 1, then d' is 2. Colorings with the best fastness to washing could be obtained when the radicals c and c' both represent the number 3.
  • an agent according to the invention is characterized in that it contains at least one first organic silicon compound (a1) of the formula (II), (R 5 O)c( R 6 )dSi-(A)e-[NR 7 -(A')]f-[O-(A'')]g-[NR 8 -(A''')]h-Si(R 6 ')d'(OR 5 ')c' (II), where - R 5 and R 5 ' independently represent a methyl group or an ethyl group, - c and c' both represent the number 3, and - d and d' both stand for the number 0.
  • the organic silicon compounds according to the invention correspond to the formula (IIa) (R 5 O) 3 Si-(A)e-[NR7-( A')]f-[O-(A'')]g-[NR8-(A''')]h-Si(OR 5 ') 3 (IIa).
  • the radicals e, f, g and h can, independently of one another, represent the number 0 or 1, with at least one radical from e, f, g and h being different from zero.
  • the abbreviations e, f, g and h therefore define which of the groups -(A)e- and -[NR7-(A')]f- and -[O-(A'')]g- and - [NR8-(A''')]h- are located in the central part of the organic silicon compound of formula (II).
  • the presence of certain groups has proven to be particularly advantageous with regard to increasing wash fastness.
  • Particularly good results can be obtained when at least two of the radicals e, f, g and h are the number 1.
  • e and f both represent the number 1.
  • g and h both represent the number 0.
  • the organic silicon compound according to the invention of the formula (IIb) (R 5 O)c(R 6 )dSi-(A)-[NR7-(A')]-Si(R 6 ')d'(OR 5 ')c' (IIb ).
  • the radicals A, A', A'', A''' and A''' independently represent a linear or branched, divalent C 1 -C 20 -alkylene group.
  • the radicals A, A′, A′′, A′′′′ and A′′′′ independently of one another preferably represent a linear, divalent C 1 -C 20 -alkylene group.
  • the radicals A, A′, A′′, A′′′′ and A′′′′ independently represent a linear divalent C 1 -C 6 -alkylene group.
  • the radicals A, A′, A′′, A′′′′ and A′′′′ are particularly preferably, independently of one another, 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 -).
  • the radicals A, A′, A′′, A′′′′ and A′′′′ are very particularly preferably a propylene group (-CH 2 -CH 2 -CH 2 -).
  • the organic silicon compound of the formula (II) according to the invention contains a structural grouping -[NR 7 -(A')]-.
  • the organic silicon compound of the formula (II) according to the invention contains a structural grouping -[NR8-(A''')]-.
  • radicals R 7 and R 8 independently stand for a hydrogen atom, a C 1 -C 6 - alkyl group, a hydroxy-C 1 -C 6 -alkyl group, a C 2 -C 6 -alkenyl group, an amino-C 1 - C 6 -alkyl group or a moiety of formula (III) - (A'''')-Si(R 6 '')d''(OR 5 '')c'' (III).
  • the radicals R7 and R8 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 group of the formula (III). If the radical f is the number 1 and the radical h is the number 0, the organic silicon compound according to the invention contains the moiety [NR 7 -(A')] but not the moiety -[NR 8 -(A''' )] . If the radical R 7 now stands for a group of the formula (III), then the pretreatment agent (a) contains an organic silicon compound with 3 reactive silane groups.
  • an agent according to the invention is characterized in that it contains at least one first organic silicon compound (a1) of the formula (II), (R 5 O)c(R 6 )dSi-(A)e-[NR 7 - (A')]f-[O-(A'')]g-[NR 8 -(A''')]h-Si(R 6 ')d'(OR 5 ')c' (II), where - e and f both represent the number 1, - g and h both represent the number 0, - A and A' independently represent a linear, divalent C 1 -C 6 -alkylene group and - R7 represents a hydrogen atom, a methyl group, a 2-hydroxyethyl group, a 2-alkenyl group, a 2-aminoethyl group or a group of formula (III).
  • an agent according to the invention is characterized in that it contains at least one first organic silicon compound (a1) of the formula (II), where e and f both represent the number 1, g and h both represent the number 0 - A and A' independently represent a methylene group (-CH 2 -), an ethylene group (-CH 2 -CH 2 -) or a propylene group (-CH 2 -CH 2 -CH 2 ), and - R7 represents a hydrogen atom, a methyl group, a 2-hydroxyethyl group, a 2-alkenyl group, a 2-aminoethyl group or a group of formula (III).
  • a1 of the formula (II) where e and f both represent the number 1, g and h both represent the number 0 - A and A' independently represent a methylene group (-CH 2 -), an ethylene group (-CH 2 -CH 2 -) or a propylene group (-CH 2 -CH 2 -CH
  • Organic silicon compounds of the formula (II) which are highly suitable for achieving the object of the invention are -3-(trimethoxysilyl)-N-[3-(trimethoxysilyl)propyl]-1-propanamine - 3-(triethoxysilyl)-N-[3-(triethoxysilyl)propyl]-1-propanamine
  • organic silicon compounds of the formula (II) are commercially available.
  • bis(trimethoxysilylpropyl)amine with CAS number 82985-35-1 can be purchased from Sigma-Aldrich.
  • bis[3-(triethoxysilyl)propyl]amine with CAS number 13497-18-2 is commercially available from Sigma-Aldrich.
  • N-methyl-3-(trimethoxysilyl)-N-[3-(trimethoxysilyl)propyl]-1-propanamine is referred to as bis(3-trimethoxysilylpropyl)-N-methylamine and is commercially available from Sigma-Aldrich or Fluorochem .
  • 3-(triethoxysilyl)-N,N-bis[3-(triethoxysilyl)propyl]-1-propanamine with CAS number 18784-74-2 can be purchased from Fluorochem or Sigma-Aldrich.
  • an agent according to the invention is characterized in that it contains at least one first organic silicon compound (a1) of the formula (II) which is selected from the group consisting of - 3-(trimethoxysilyl)-N-[3-(trimethoxysilyl).
  • the agent not according to the invention contains at least one organic silicon compound of the formula (IV) as the second organic silicon compound (a2) R9Si(OR 10 )k( R11 )m (IV).
  • the compounds of formula (IV) are organosilicon compounds selected from silanes having one, two or three silicon atoms, where the organosilicon compound comprises one or more hydroxyl groups and/or hydrolyzable groups per molecule.
  • the organic silicon compound(s) of the formula (IV) can also be referred to as silanes of the alkyl-alkoxy-silanes or alkyl-hydroxy-silanes type, R 9 Si(OR 10 ) k (R 11 ) m (IV), where - R 9 represents a C 1 -C 12 alkyl group, -R 10 represents a hydrogen atom or a C 1 -C 6 alkyl group, - R 11 is a C 1 -C 6 alkyl group, - k is an integer from 1 to 3, and - m is the integer 3 - k.
  • a composition according to the invention is characterized in that it contains at least one second organic silicon compound (a2) of the formula (IV) R9Si(OR 10 )k(R 11 )m (IV), where - R9 represents a C 1 -C 12 alkyl group, - R10 represents a hydrogen atom or a C 1 -C 6 alkyl group, - R 11 represents a C 1 -C 6 alkyl group, - k represents an integer from 1 to 3, and - m is the integer 3 - k.
  • a2 contains at least one second organic silicon compound (a2) of the formula (IV) R9Si(OR 10 )k(R 11 )m (IV), where - R9 represents a C 1 -C 12 alkyl group, - R10 represents a hydrogen atom or a C 1 -C 6 alkyl group, - R 11 represents a C 1 -C 6 alkyl group, - k represents an integer from 1 to 3, and - m is
  • an agent according to the invention is characterized in that it 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) R 9 Si(OR 10 )k(R 11 )m (IV), where - R 9 represents a C 1 -C 12 alkyl group, - R 10 represents a hydrogen atom or a C 1 -C 6 alkyl group, - R 11 represents a C 1 -C 6 alkyl group - k is an integer from 1 to 3, and - m is the integer 3 - k.
  • an agent according to the invention is characterized in that it 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) R 9 Si(OR 10 ) k (R 11 ) m (IV), where - R 9 represents a C 1 -C 12 alkyl group, - R10 represents a hydrogen atom or a C 1 -C 6 alkyl group, - R11 represents a C 1 -C 6 alkyl group, - k represents an integer of 1 to 3, and -m is the integer 3-k.
  • the radical R9 is a C 1 -C 12 - alkyl group.
  • R 9 is preferably a linear C 1 -C 8 -alkyl group.
  • R 9 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.
  • R9 is particularly preferably a methyl group, an ethyl group or an n-octyl group.
  • the radical R10 represents a hydrogen atom or a C 1 -C 6 -alkyl group.
  • R 10 particularly preferably represents a methyl group or an ethyl group.
  • the radical R 11 is a C 1 -C 6 - alkyl group.
  • R 11 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. Dyeings with the best fastness to washing could be obtained , if in the process an agent (a) was used, which contains at least one organic silicon compound of the formula (IV) in which the radical k is the number 3. In this case, the radical m is the number 0.
  • Organic silicon compounds of the formula (IV) which are particularly suitable for solving the problem addressed by the invention are -methyltrimethoxysilane - methyltriethoxysilane
  • an agent according to the invention is characterized in that it contains at least one second organic silicon compound (a2) of the formula (IV) selected from the group consisting of - methyltrimethoxysilane - methyltriethoxysilane - ethyltrimethoxysilane - ethyltriethoxysilane - hexyltrimethoxysilane - hexyltriethoxysilane - octyltrimethoxysilane - octyltriethoxysilane - dodecyltrimethoxysilane and/or - dodecyltriethoxysilane.
  • a2 of the formula (IV) selected from the group consisting of - methyltrimethoxysilane - methyltriethoxysilane - ethyltrimethoxysilane - ethyltriethoxysilane - hexyltrimeth
  • an agent according to the invention is characterized in that it contains at least one first organic silicon compound (a1) 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 second organic silicon compound (a2) of the formula (IV), which is selected from the group consisting of methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, hexyltrimethoxysilane and hexyltriethoxysilane.
  • the organic silicon compounds described above are reactive compounds. To achieve particularly good staining results, it is particularly important Advantage of using the organic silicon compounds of the formula (I) and/or (II) in certain quantity ranges on average (a).
  • the agent according to the invention - based on the total weight of the agent - one or more organic silicon compounds (a1) from the group of compounds of the formulas (I) and (II) in a total amount of 0.1 to 99.0% by weight, preferably from 0.3 to 33% by weight and particularly preferably from 1.5 to 11.0% by weight.
  • an agent according to the invention is therefore characterized in that it - based on the total weight of the agent - one or more organic silicon compounds (a1) from the group of compounds of the formulas (I) and (II) in a Total amount from 0.1 to 99.0% by weight, preferably from 0.3 to 33% by weight and particularly preferably from 1.5 to 11.0% by weight.
  • organic silicon compounds of the formula (IV) it is also of particular advantage to use in specific amounts, on average (a).
  • a very particularly preferred agent is characterized in that - based on the total weight of the agent - one or more organic silicon compounds (a2) from the group of compounds of the formula (IV) in a total amount of in a total amount of 0.1 to 99.0% by weight, preferably from 0.6 to 66.0% by weight and particularly preferably from 3.0 to 22.0% by weight.
  • an agent according to the invention is therefore characterized in that - based on the total weight of the agent - one or more organic silicon compounds (a2) from the group of compounds of the formula (IV) in a total amount of 0.1 to 99.0% by weight, preferably from 0.6 to 66.0% by weight and particularly preferably from 3.0 to 22.0% by weight.
  • the amounts used of the silanes from groups (a1) and (a2) add up to a maximum of 100% by weight in this embodiment.
  • Oligomers or condensates of the organic silicon compounds The organic silicon compounds (a1) according to the invention, in particular those of the formula (I) and/or (II) and/or (IV), are reactive compounds which undergo a hydrolysis and condensation reaction with water can enter.
  • 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 through mixing.
  • an exothermic hydrolysis reaction takes place according to the following scheme (reaction scheme using 3-aminopropyltriethoxysilane as an example): Depending on the number of hydrolyzable C 1 -C 6 alkoxy groups per silane molecule, the hydrolysis reaction can also take place several times per C 1 -C 6 alkoxy silane used: Hydrolysis using the example of methyltrimethoxysilane: Depending on the amount of water used, the hydrolysis reaction can also take place several times per C 1 -C 6 -alkoxysilane used: or.
  • the partially (or in parts also completely) hydrolyzed C 1 -C 6 -alkoxysilanes are condensed.
  • the precondensation can, for example, take place according to the following scheme: Both partially hydrolyzed and fully hydrolyzed C 1 -C 6 -alkoxysilanes can take part in the condensation reaction and undergo a condensation with partially or completely hydrolyzed C 1 -C 6 -alkoxysilanes that have not yet reacted. Examples of possible condensation reactions are (shown using the mixture of (3-aminopropyl)triethoxysilane and methyltrimethoxysilane): and or
  • condensation to give a dimer is shown in each case, but further condensations to give oligomers having a plurality of silane atoms are also possible and also preferred.
  • This hydrolysis or condensation reaction begins even in the presence of very small amounts of water, which is why the oligomers and/or condensation products of the aforementioned organic silicon compounds are also included in this invention.
  • an agent for coloring keratinic material in particular human hair, containing (a) at least two different organic silicon compounds, the oligomers and/or the condensation products thereof, each organic silicon compound being independently of the others from the Group of silanes is selected with one, two or three silicon atoms, wherein the organic silicon compound comprises one or more hydroxyl groups and / or hydrolyzable groups per molecule, (b) at least one pigment, and (c) at least one at 20 ° C liquid fatty component and /or an organic solvent.
  • Pigments (b) The agent according to the invention contains at least one pigment (b) as the second essential component.
  • pigments are understood to mean coloring compounds which have a solubility in water at 25° C. of less than 0.5 g/l, preferably less than 0.1 g/l, even more preferably less than 0. Possess 05 g/L.
  • the water solubility can be determined, for example, using the method described below: 0.5 g of the pigment is weighed out in a glass beaker. A stir bar is added. Then one liter of distilled water is added. This mixture is heated to 25°C with stirring on a magnetic stirrer for one hour. 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.
  • Suitable pigments or colored pigments can be of inorganic and/or organic origin.
  • an agent (b) according to the invention 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, ochre, umber, green earth, burnt terra di sienna or graphite, for example.
  • black pigments such. B. iron oxide black
  • colored pigments such. B. ultramarine or iron oxide red and fluorescent or phosphorescent pigments
  • Colored metal oxides, metal hydroxides and metal oxide hydrates, mixed phase pigments, sulfur-containing silicates, silicates, metal sulfides, complex metal cyanides, metal sulfates, metal chromates and/or metal molybdates are particularly suitable.
  • 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), hydrated chromium oxide (CI77289 ), Iron Blue (Ferric Ferrocyanide, CI77510) and/or Carmine (Cochineal).
  • Colored pigments which are also particularly preferred according to the invention are colored pearlescent pigments. These are usually based on mica and/or mica and can be coated with one or more metal oxides. Mica belongs to the layered silicates.
  • the mica mainly muscovite or phlogopite
  • the mica is coated with a metal oxide.
  • synthetic mica optionally coated with one or more metal oxide(s) can also be used as 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).
  • an agent according to the invention is characterized in that it contains at least one pigment 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 Mica or mica base coated with at least one metal oxide and/or one metal oxychloride.
  • a composition according to the invention is characterized in that it (b) contains at least one pigment which is selected from pigments based on mica or mica, which are coated 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), hydrated chromium oxide (CI 77289), chromium oxide (CI 77288) and/or iron blue (Ferric Ferrocyanide, CI 77510).
  • 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
  • color pigments are commercially available, for example under the trade names Rona®, Colorona®, Xirona®, Dicrona® and Timiron® from Merck, Ariabel® and Unipure® from Sensient, Prestige® from Eckart Cosmetic Colors and Sunshine® available from Sunstar.
  • Very particularly preferred color pigments with the trade name Colorona® are, for example: Colorona Copper, Merck, MICA, CI 77491 (IRON OXIDES) Colorona Passion Orange, Merck, Mica, CI 77491 (Iron Oxides), Alumina Colorona Patina Silver, Merck, MICA, CI 77499 (IRON OXIDES), CI 77891 (TITANIUM DIOXIDE) Colorona RY, Merck, CI 77891 (TITANIUM DIOXIDE), MICA, CI 75470 (CARMINE) Colorona Oriental Beige, Merck, MICA, CI 77891 (TITANIUM DIOXIDE), CI 77491 (IRON OXIDES) Colorona Dark Blue, Merck, MICA, TITANIUM DIOXIDE, FERRIC FERROCYANIDE Colorona Chameleon, Merck, CI 77491 (IRON OXIDES), MICA Colorona Abrare Amber, Merck, M
  • particularly preferred color pigments with the trade name Unipure® are, for example: Unipure Red LC 381 EM, Sensient CI 77491 (Iron Oxides), Silica Unipure Black LC 989 EM, Sensient, CI 77499 (Iron Oxides), Silica Unipure Yellow LC 182 EM , Sensient, CI 77492 (Iron Oxides), Silica
  • the agent according to the invention can also (b) contain one or more coloring compounds from the group of organic pigments.
  • the organic pigments according to the invention are correspondingly insoluble organic dyes or color lakes, for example from the group of nitroso, nitro, azo, xanthene, anthraquinone, isoindolinone, isoindoline, quinacridone, perinone, perylene, diketopyrrolopyrrole, 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,
  • an agent according to the invention is characterized in that it contains at least one organic pigment selected from the group consisting of 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,
  • the organic pigment can also be a colored lake.
  • the term colored lake is understood to mean particles which comprise a layer of absorbed dyes, the unit made up 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 aluminum.
  • Alizarin color lake for example, can be used as the color lake.
  • Pigments with a specific shape can also be used to color the keratin material.
  • a pigment based on a lamellar and/or a lenticular substrate flake can be used.
  • coloring based on a small substrate plate comprising a vacuum-metallized pigment is also possible.
  • a method according to the invention can be characterized in that the corresponding agent also contains one or more coloring compounds from the group of pigments based on a lamellar substrate platelet, pigments based on a lenticular substrate platelet and vacuum-metallized pigments.
  • the substrate flakes 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 flakes 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 flakes are 2.5 to 50 nm, 5 to 50 nm, 10 to 50nm; 2.5 to 30nm, 5 to 30nm, 10 to 30nm; 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. Due to the small thickness of the substrate flakes, the pigment has a particularly high hiding power.
  • the substrate plates have a monolithic structure. In this context, monolithic means consisting of a single self-contained unit without fractures, layers or inclusions, although structural changes can occur within the substrate platelets.
  • the substrate flakes are preferably constructed homogeneously, ie no concentration gradient occurs within the flakes.
  • the substrate flakes are not built up in layers and have no particles or particles distributed therein.
  • the size of the small substrate can be adjusted to the respective application, in particular the desired effect on the keratin material.
  • the substrate flakes have an average largest diameter of about 2 to 200 ⁇ m, in particular about 5 to 100 ⁇ m.
  • the form factor (aspect ratio), expressed as 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 mean size of the uncoated substrate flakes is the d50 value of the uncoated substrate flakes.
  • the substrate flakes can be constructed from any material that can be formed into flake form. They can be of natural origin, but also produced synthetically. Materials from which the substrate flakes 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 flakes are preferably constructed from metal (alloys). Any metal suitable for metallic luster pigments can be used as the metal.
  • Such metals include iron and steel, as well as all air and water-resistant (semi)metals such as platinum, zinc, chromium, molybdenum and silicon, and their alloys such as aluminum bronze and brass.
  • Preferred metals are aluminum, copper, silver and gold.
  • Preferred substrate flakes are aluminum flakes and brass flakes, with aluminum substrate flakes being particularly preferred.
  • Lamellar substrate platelets are characterized by an irregularly structured edge and are also referred to as "cornflakes" because of their appearance. Due to their irregular structure, pigments based on lamellar substrate flakes generate a high proportion of scattered light.
  • the pigments based on lamellar substrate flakes do not completely cover the existing color of a keratinic material and, for example, effects analogous to natural graying can be achieved.
  • Vacuum metallized pigments (vacuum metallized pigments, VMP) can be obtained, for example, by releasing metals, metal alloys or metal oxides from appropriately coated foils.
  • substrate flakes which comprise a pigment metallized in a vacuum are also referred to as VMP substrate flakes.
  • Aluminum VMP substrate flakes can be obtained, for example, by releasing aluminum from metallized foils.
  • the substrate flakes made of metal or metal alloy can be passivated, for example by anodizing (oxide layer) or chromating.
  • Uncoated lamellar, lenticular and/or VPM substrate flakes, in particular those made of metal or metal alloy reflect the incident light to a large extent and produce a light-dark flop, but no color impression.
  • a color impression can be generated, for example, due to optical interference effects.
  • Such pigments can be based on substrate flakes coated at least once. These show interference effects due to the superimposition of differently refracted and reflected light beams.
  • preferred pigments are pigments based on a coated lamellar substrate platelet.
  • the substrate flake preferably has at least one coating B made of a high-index metal oxide with a coating thickness of at least 50 nm. There is preferably another coating A between the coating B and the surface of the small substrate.
  • Suitable materials for the coatings A, B and C are all substances which can be applied in the form of a film and permanently to the substrate flakes and, in the case of layers A and B, have the required optical properties.
  • a coating of part of the surface of the substrate flakes is sufficient to obtain a pigment with a glossy effect.
  • only the upper and/or lower side of the substrate flakes can be coated, with the side surface(s) being omitted.
  • the entire surface of the optionally passivated substrate flakes, including the side surfaces, is preferably covered by coating B.
  • the substrate flakes are thus completely encased by coating B. This improves the optical properties of the pigment and increases the mechanical and chemical resilience of the pigments.
  • the coated substrate flakes preferably have only one coating A, B and, if present, C each.
  • the coating B is made up of at least one metal oxide with a high refractive index. Materials with a high refractive index have a refractive index of at least 1.9, preferably at least 2.0 and particularly preferably at least 2.4.
  • the coating B preferably comprises at least 95% by weight, particularly preferably at least 99% by weight, of high-index metal oxide(s).
  • the coating B has a thickness of at least 50 nm. The thickness of coating B is preferably no more than 400 nm, particularly preferably at most 300 nm.
  • High-index metal oxides suitable for coating B are preferably selectively light-absorbing (i.e.
  • Coating B can contain a selectively absorbing dye, preferably 0.001 to 5% by weight, particularly preferably 0.01 to 1% by weight, based in each case on the total amount of coating B. Suitable organic and inorganic dyes are stable in have a metal oxide coating installed.
  • the coating A preferably has at least one metal oxide and/or metal oxide hydrate with a low refractive index.
  • Coating A preferably comprises at least 95% by weight, particularly preferably at least 99% by weight, of low-index metal oxide (hydrate).
  • Materials with low refractive index have a refractive index of at most 1.8, preferably at most 1.6.
  • the low-index metal oxides 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, 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 flakes and the inner surface of coating B is preferably at most 100 nm, particularly preferably at most 50 nm, particularly preferably at most 20 nm.
  • the pigment based on a lamellar substrate flake has a layer A and a layer B, it is preferred that the pigment has a lamellar substrate flake 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 of a metal oxide (hydrate) which is different from the underlying coating B on.
  • suitable metal oxides are silicon (di)oxide, silicon oxide hydrate, aluminum oxide, Hydrated alumina, 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 are used in particular as protection against corrosion and also for chemical and physical stabilization. Layers A and C particularly preferably contain silicon dioxide or aluminum oxide, which are applied by the sol-gel method.
  • This method comprises dispersing the uncoated lamellar substrate flakes or the lamellar substrate flakes already coated with layer A and/or layer B in a solution of a metal alkoxide such as tetraethyl orthosilicate or aluminum triisopropoxide (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 adding a weak base or acid to hydrolyze the metal alkoxide, thereby forming a film of the metal oxide on the surface of the (coated) substrate flakes.
  • a metal alkoxide such as tetraethyl orthosilicate or aluminum triisopropoxide
  • 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 appropriate, subsequent post-treatment (for example converting a hydroxide-containing layer formed into the oxide layer by tempering).
  • each of the coatings A, B and/or C may be composed of a mixture of two or more metal oxide (hydrate)s, each of the coatings is preferably composed of a metal oxide (hydrate).
  • the pigments based on coated lamellar or lenticular substrate flakes or the pigments based on coated VMP substrate flakes 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 flakes, the pigment has a particularly high hiding power.
  • the small thickness of the coated substrate flakes is achieved in particular by the fact that the thickness of the uncoated substrate flakes is small, but also by the fact that the thicknesses of the coatings A and, if present, C are set 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 keratin material can be significantly increased in the outermost layer, depending on the structure
  • Layer A, B or C is additionally modified by organic compounds such as silanes, phosphoric acid esters, titanates, borates or carboxylic acids.
  • the organic compounds are bound to the surface of the outermost layer A, B or C, which preferably contains 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 bond to the layer A, B or C containing metal oxide. 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-methacryloxypropyltris(methacryloxypropyltris(methacryloxy) yethoxy) 3-methacryloxypropyltris(butoxyethoxy)silane, 3-methacryloxypropyltris(propoxy)silane, 3-methacryloxypropyltris(butoxy)silane, 3-acryloxypropyltris(methoxyethoxy)silane, 3-acryloxypropyltris(butoxyethoxy)silane,
  • a modification with a monofunctional silane in particular an alkyl silane or aryl silane, can take place.
  • This has only one functional group which can bond covalently to the surface of pigment based on coated lamellar substrate flakes (ie to the outermost layer containing metal oxide) or, if the coverage is not quite complete, to the metal surface.
  • the hydrocarbon residue of the silane points away from the pigment.
  • a different degree of hydrophobicization of the pigment is achieved. Examples of such silanes are hexadecyltrimethoxysilane, propyltrimethoxysilane, etc.
  • Pigments based on silicon dioxide-coated aluminum substrate flakes are particularly preferably surface-modified with a monofunctional silane. Octyltrimethoxysilane, octyltriethoxysilane, hecadecyltrimethoxysilane and hecadecyltriethoxysilane are particularly preferred.
  • the changed surface properties / water repellency can improve adhesion, abrasion resistance and orientation in the application.
  • Suitable pigments based on a lamellar substrate flake include, for example, the pigments from Eckart's VISIONAIRE series. Pigments based on a lenticular substrate flake are available, for example, under the name Alegrace® relaxing from Schlenk Metallic Pigments GmbH.
  • Pigments based on a substrate flake which comprises a vacuum-metallized pigment
  • a substrate flake which comprises a vacuum-metallized pigment
  • the use of the aforementioned pigments in agent (b) of the process according to the invention is very particularly preferred.
  • the pigments used have a specific particle size. It is therefore advantageous according to the invention if the at least one pigment has an average particle size D 50 of from 1.0 to 50 ⁇ m, preferably from 5.0 to 45 ⁇ m, preferably from 10 to 40 ⁇ m, in particular from 14 to 30 ⁇ m.
  • the mean 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 1.0 to 20.0% by weight, preferably 5.0 to 10.0% by weight, based in each case on the total weight of the agent.
  • an agent according to the invention is characterized in that it - based on the total weight of the agent - one or more pigments (b) in a total amount of 1.0 to 20.0 wt .-%, preferably 5.0 up to 10.0% by weight.
  • Liquid fats and/or organic solvents (c) As the third component or substance class (c) essential to the invention, the agent according to the invention contains at least one compound from the group consisting of the fat components that are liquid at 20° C. and the organic solvents.
  • liquid fats and/or the organic solvents (c) ensure fine dispersion of the pigments and ensure homogeneous mixing with the silanes (a), in particular with the particularly preferred silanes (a1) and (a2) described above.
  • addition of the fat components or solvents increases the storage stability of the agent.
  • fatty components are organic compounds with a solubility in water at room temperature (22° C.) and atmospheric pressure (760 mmHg) of less than 1% by weight, preferably less than 0.1% by weight. Roger that. A fat component that is liquid at 20°C has a melting point below 20°C (measured under atmospheric pressure (760 mmHg)).
  • fat components explicitly only includes uncharged (ie non-ionic) compounds.
  • Fat components have at least one saturated or unsaturated alkyl group with at least 8 carbon atoms.
  • the molecular weight of the fat components is a maximum of 5000 g/mol, preferably at a maximum of 2500 g/mol and particularly preferably at a maximum of 1000 g/mol.
  • the fat components are neither polyoxyalkylated nor polyglycerylated compounds.
  • the components from the group consisting of the C 12 -C 30 fatty acid triglycerides, the C 12 -C 30 fatty acid diglycerides, the C 12 -C 30 fatty alcohols and/or the hydrocarbons are understood as preferred fat components, with the prerequisite in each case that every compound from the aforementioned classes of substances has a melting point below 20°C.
  • the components from the group consisting of the C 12 -C 30 fatty acid triglycerides, the C 12 -C 30 fatty acid diglycerides, the C 12 -C 30 fatty alcohols and/or the hydrocarbons are understood as preferred fat components, with the prerequisite in each case that every compound from the aforementioned classes of substances has a melting point below 20°C.
  • nonionic substances are explicitly considered as fat components.
  • Charged compounds such as fatty acids and their salts are not considered to be a fat component.
  • Very particularly suitable fatty components (c) can be selected from the group consisting of linear or cyclic silicone oils, hydrocarbon oils, liquid fatty acid triglycerides, liquid fatty alcohols, ester oils and mixtures thereof.
  • an agent according to the invention is characterized in that it contains at least one fatty component (c) that is liquid at 20° C., which is selected from the group consisting of linear or cyclic silicone oils, hydrocarbon oils, liquid fatty acid triglycerides, liquid fatty alcohols, ester oils and mixtures thereof.
  • Silicone oils can also be referred to as oligoalkylsiloxanes and polyalkylsiloxanes that are liquid at 20°C, ie the silicone oils have a melting point below 20°C (at atmospheric pressure (760 mmHg).
  • Preferred linear silicone oils are oligoalkylsiloxanes of the general formula (V) where z is an integer from 0 to 10,000, preferably an integer from 0 to 1000, more preferably an integer from 0 to 100, and very particularly preferably an integer from 0 to 10.
  • Very particularly preferred linear oligoalkylsiloxanes are, for example
  • Hexamethyldisiloxane has the CAS number 107-46-0 and can be purchased commercially, for example, from Sigma-Aldrich.
  • Octamethyltrisiloxane has the CAS number 107-51-7 and is also commercially available from Sigma-Aldrich.
  • Decamethyltetrasiloxane has the CAS number 141-62-8 and is also commercially available from Sigma-Aldrich.
  • Another particularly suitable silicone oil can be purchased commercially, for example, under the trade name Dimethicone Fluid 5 cSt from Clearco. This silicone oil has the generic name polydimethylsiloxane and has the CAS number 63148-62-9.
  • the substance is a clear, colorless and odorless liquid, thinly viscous oil.
  • Another silicone oil with particularly good suitability can be purchased under the trade name Xiameter PMX 200 (1.5 cSt) from Dow Corning. This oil is also a dimethicone or polydimethylsiloxane, which has the CAS number 63148-62-9.
  • Preferred cyclic oligoalkylsiloxanes are compounds of general formula (VI) where y is an integer from 1 to 5. z preferably represents the numbers 1, 2 or 3.
  • a composition according to the invention is characterized in that it contains at least one silicone oil of the formula ( V) and/or (VI) contains, where z is an integer from 0 to 10,000, preferably an integer from 0 to 1000, more preferably an integer from 0 to 100, and very particularly preferably an integer from 0 to 10, where y is an integer from 1 to 5, preferably an integer from 1 to 3.
  • an agent according to the invention is characterized in that it contains at least one oligoalkylsiloxane (c) selected from the group consisting of hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane and/or decamethylcyclopentasiloxane.
  • oligoalkylsiloxane (c) selected from the group consisting of hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane and/or decamethylcyclopentasiloxane.
  • the oligoalkylsiloxanes are made up exclusively of dialkylsilyl groups (particularly dimethylsilyl groups) and trialkylsilyl groups (particularly trimethylsilyl groups) linked to one another via oxygen atoms are.
  • the oligoalkylsiloxanes within the meaning of this invention are therefore not reactive compounds themselves and also do not have any hydrolyzable groups.
  • Hydrocarbon oils are also particularly well-suited to fat components that are liquid at 20 °C. Hydrocarbons are compounds with 8 to 80 carbon atoms consisting exclusively of carbon and hydrogen atoms.
  • aliphatic hydrocarbons such as, for example, mineral oils, liquid paraffin oils (eg Paraffinium Liquidum or Paraffinum Perliquidum), isoparaffin oils and polydecenes.
  • the hydrocarbons according to the invention are also characterized in that they have a melting point below 20° C. under atmospheric pressure.
  • the liquid fatty acid triglycerides are also particularly well-suited to fatty components which are liquid at 20° C.
  • a C 12 -C 30 fatty acid triglyceride in the context of the present invention is understood as meaning the triester of the trihydric alcohol glycerol with three equivalents of fatty acid.
  • fatty acids are understood to mean saturated or unsaturated, unbranched or branched, unsubstituted or substituted C 12 -C 30 -carboxylic acids.
  • Unsaturated fatty acids can be monounsaturated or polyunsaturated. In the case of an unsaturated fatty acid, its CC double bond(s) can have the cis or trans configuration.
  • the fatty acid triglycerides are particularly suitable if at least one of the ester groups is formed from glycerol with a fatty acid that is selected is made from dodecanoic acid (lauric acid), tetradecanoic acid (myristic acid), hexadecanoic acid (palmitic acid), tetracosanoic acid (lignoceric acid), octadecanoic acid (stearic acid), eicosanoic acid (arachidic acid), docosanoic acid (behenic acid), petroselinic acid [(Z)-6-octadecenoic acid], palmitoleic acid [ (9Z)-hexadec-9-enoic acid], oleic acid [(9Z)-octadec-9-enoic acid], elaidic acid [(9E)-octadec-9-enoic acid], erucic acid [(13Z)-docos-13-en
  • a further particularly preferred embodiment is therefore an agent for coloring keratinic material, which is characterized in that it contains a naturally occurring fatty acid triglyceride and/or mixtures of naturally occurring fatty acid triglycerides as the fat component (c) that is liquid at 20° C , Olive oil, sunflower oil, macadamia nut oil, moringa oil, apricot kernel oil, marula oil and/or optionally hardened castor oil are included.
  • the liquid fatty alcohols are also particularly suitable fatty components which are liquid at 20° C.
  • Preferred linear, unsaturated fatty alcohols are (9Z)-octadec-9-en-1-ol (oleyl alcohol), (9E)-octadec-9-en-1 -ol (elaidyl alcohol), (9Z,12Z)-octadeca-9,12-dien-1-ol (linoleyl alcohol), (9Z,12Z,15Z)-octadeca-9,12,15-trien-1-ol (linolenoyl alcohol ), gadoleyl alcohol ((9Z)-eicos-9-en-1-ol), arachidonic alcohol ((5Z,8Z,11Z,14Z)-eicosa-5,8,11,14-tetraen-1-ol), erucyl alcohol ( (13Z)-Docos-13-en-1-ol) and/or brassidyl alcohol ((13E)-Docosen-1-ol).
  • ester oils are also particularly well-suited to fatty components that are liquid at 20° C.
  • Ester oils are understood to mean esters of C 12 -C 30 fatty acids with aliphatic C 1 -C 24 alcohols that are liquid at room temperature (25° C.). .
  • ester oils according to the invention are characterized in that they have a melting point below 25° C. at atmospheric pressure (1013 mbar).
  • an aftertreatment agent was applied to the previously dyed hair which contained at least one ester oil selected from the group consisting of the monoesters of C 12 -C 24 fatty acids with aliphatic, monovalent C 1 -C 24 alcohols is selected.
  • the aftertreatment agent contains at least one fatty component (N-3) from the group of esters of a C 12 -C 30 fatty acid and an aliphatic, monohydric C 1 -C 24 alcohol contains.
  • N-3 from the group of esters of a C 12 -C 30 fatty acid and an aliphatic, monohydric C 1 -C 24 alcohol contains.
  • the C 12 -C 24 fatty acids are particularly well suited.
  • C 12 -C 24 fatty acids which are suitable for forming the ester oils (N-3) are caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, Oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, elaeostearic acid, arachidic acid, gadoleic acid, behenic acid and erucic acid and technical mixtures thereof.
  • fatty alcohol components in the ester oils are isopropyl alcohol, caproic alcohol, caprylic alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, linolenyl alcohol, elaeostearyl alcohol, arachyl alcohol, gadoleyl alcohol, Behenyl alcohol, erucyl alcohol and brassidyl alcohol and technical mixtures thereof.
  • C 12 -C 24 fatty acids are esterified by reaction with a C 1 -C 24 aliphatic alcohol, which is most preferably a mono-alcohol, such that the esterification results in a mono-ester.
  • the aliphatic C 1 -C 24 alcohols can be linear or branched, saturated or mono- or polyunsaturated.
  • an alcohol can be used, for example, which is selected from the group consisting of methanol, ethanol, n-propanol, isopropanol, n-butanol, n-pentanol, 2-ethylhexanol, n- hexanol, n-octanol, n-decanol and n-dodecanol.
  • Examples of monohydric, unsaturated, C 1 -C 24 alcohol are oleyl alcohol (octadec-9-en-1-ol), palmitoleyl alcohol (cis-9-hexadecen-1-ol), elaidyl alcohol (trans-9-octadecen-1- ol) and cis-11-octadecen-1-ol.
  • the C 12 -C 24 fatty acids and the C 1 -C 12 alcohols are selected such that the ester formed from the two reactants by esterification is an ester oil, ie at 1013 mbar has a melting point below 25 °C.
  • ester oils of this invention can be used in the form of commercially available raw materials which are mixtures of the esters obtained from different chain length fatty acids and/or different chain length alcohols. These raw materials can have a melting range. For these raw materials, a melting point below 25 °C means that the melting process begins at a temperature below 25 °C. If, for example, an ester oil can be used in the form of a specific raw material on average, this raw material having a melting range of 16 to 27 °C, then this raw material contains at least one ester oil with a melting point below 25 °C. This ester oil is thus in accordance with the invention.
  • 2-ethylhexyl palmitate (Cegesoft ® 24), isopropyl myristate (Rilanit ® IPM), isononanoic acid C16-18-alkyl ester (Cetiol ® SN), stearic acid 2-ethylhexyl ester (Cetiol ® 868), cetyl oleate, glycerol tricaprylate, coconut fatty alcohol caprinate/-caprylate (Cetiol ® LC), n-butyl stearate, oleyl lerucate (Cetiol ® J 600), isopropyl palmitate (Rilanit ® IPP), oleyl oleate (Cetiol ® ), lauric acid hexyl ester (Cetiol ® A), di-n-butyl adipate (Cetiol ® B),
  • the ester oil (N-3) is very particularly preferably selected from the group consisting of isopropyl myristate, 2-ethylhexyl palmitate, isononanoic acid C16-18-alkyl ester, stearic acid 2-ethylhexyl ester, cetyl oleate, coconut fatty alcohol caprate, coconut fatty alcohol caprylate, n-butyl stearate, oleyl lerucate, isopropyl palmitate, oleyl oleate, lauric acid hexyl ester, cetearyl isononanoate and oleic acid decyl ester.
  • Isopropyl myristate is alternatively referred to as isopropyl myristate and has the CAS number 110-27-0.
  • Isopropyl myristate is a colorless and odorless liquid. The melting point is between 0 and 1 °C.
  • 2-ethylhexyl palmitate is also referred to as hexadecanoic acid 2-ethylhexyl ester and has the CAS number 29806-73-3 .
  • 2-Ethylhexyl Palmitate is a branched, saturated ester oil of palmitic acid and ethyl hexyl alcohols.
  • Isononanoic acid C16-18-alkyl ester is alternatively referred to as cetearyl isononanoate, this ester has the CAS numbers 84878-33-1 and 84878-34-2.
  • Isononanoic acid C16-18 alkyl ester is a clear, slightly yellowish liquid.
  • C16-18-alkyl isononanoate has a viscosity of 19 - 22 mPas.
  • Stearic acid 2-ethylhexyl ester is alternatively also referred to as ethylhexyl stearate and has the CAS number 91031-48-0.
  • Stearic acid 2-ethylhexyl ester is in the form of a clear, slightly yellowish, low-viscosity oil.
  • stearic acid 2-ethylhexyl ester has a viscosity of 14 – 16 mPas and is therefore an oil at room temperature.
  • Cetyl oleate has the CAS number 22393-86-8.
  • coconut fatty alcohol caprylate/caprate has the CAS number 95912-86-0.
  • n-Butyl stearate is alternatively referred to as stearic acid butyl ester and has the CAS numbers 85408-76-0 (C16-18) and 123-95-5 (C18).
  • n-Butyl stearate is a yellowish liquid and begins to melt at 16 °C.
  • Oleylerucate has the CAS number 17673-56-2.
  • Oleylerucate is a yellow liquid. At 20 °C oleylerucate has a viscosity of 40 – 50 mPas and is therefore an oil at room temperature.
  • isopropyl palmitate is also known as propan-2-yl hexadecanoate and has the CAS number 142-91-6.
  • the melting point of isopropyl palmitate is 13.5 °C.
  • oleyl oleate is also known as cis-9,10-octadecenyl-cis-9,10-octadecanoate or as oleic acid oleyl ester and has the CAS number 3687-45-4.
  • Oleyl oleate is a clear, slightly yellowish oil that has a viscosity of 25 - 30 mPas at 20 °C and is an oil at room temperature.
  • Lauric acid hexyl ester is alternatively also referred to as hexyl laurate and has the CAS number 34316-64-8.
  • Lauric acid hexyl ester is a clear, yellowish, odorless oil at room temperature.
  • lauric acid hexyl ester has a viscosity of 5 – 7 mPas and is an oil at room temperature.
  • cetearyl isononanoate is also known as isononanoic acid C16-18 alkyl ester and has the CAS numbers 84878-33-1 and 84878-34-2.
  • Cetearyl Isononanoate is a yellowish liquid with a melting point of 16-22°C.
  • decyl oleate is also known as decyl oleate and has the CAS number 3687-46-5.
  • Decyl oleate is a slightly yellowish liquid with a viscosity of 15 – 20 mPas at 20 °C.
  • oleic acid decyl ester is an oil at room temperature.
  • the fat component(s) (c) which is liquid at 20.degree. C. are preferably used in specific quantity ranges in the composition according to the invention. Particularly good results could be obtained when the agent - based on the total weight of the agent - one or more Fat components (c) that are liquid at 20° C.
  • a composition according to the invention is characterized in that it contains one or more fat components (c) that are liquid at 20° C. in a total amount of 1.0 to 99% by weight, based on the total weight of the composition, preferably from 10.0 to 90.0% by weight and more preferably from 40.0 to 80.0% by weight.
  • the agent according to the invention can also contain at least one organic solvent as component (c).
  • An organic solvent is understood as meaning organic substances which comprise at least one carbon atom, which are liquid at 20° C.
  • Solvents for the purposes of the present invention are in particular the compounds from the group consisting of ethanol, isopropanol, 1,2-propanediol, glycerol, polyethylene glycol, phenoxyethanol and benzyl alcohol.
  • an agent according to the invention is characterized in that it contains at least one solvent selected from the group consisting of ethanol, isopropanol, 1,2-propanediol, glycerol, polyethylene glycol, phenoxyethanol and benzyl alcohol.
  • the solvent or solvents (c) are preferably used in specific quantity ranges in the agent according to the invention.
  • an agent according to the invention is characterized in that it contains one or more solvents (c) in a total amount of from 1.0 to 99% by weight, preferably from 10% by weight, based on the total weight of the agent. 0 to 90.0% by weight and more preferably from 40.0 to 80.0% by weight.
  • the agent according to the invention in its previously described form can be applied directly as such to the keratin material or the hair.
  • the agent according to the invention is also the ready-to-use agent.
  • a major advantage of this form of application is the convenient and simple form of application, since the user can simply take the agent from the bottle or container in which it was provided and apply it to the keratin material. Mixing, shaking and/or homogenizing with one or more other components or compositions is not necessary in this embodiment.
  • the agent is preferably formulated with little or no water, so that the water content of the agent - based on the total weight of the agent - is in the range from 0 to 25.0% by weight, preferably from 0 to 10. 0 wt%, more preferably from 0 to 5.0 wt%, and most preferably from 0 to 3.0 wt%.
  • a particularly preferred agent is characterized in that it - based on the total weight of the agent - 0 to 25.0 wt .-%, preferably from 0 to 10.0 wt .-%, more preferably from 0 to 5.0% by weight, and more preferably from 0 to 3.0% by weight, water.
  • the agent in the form of a concentrate and to mix it with water before use.
  • the agent made available to the user is preferably also made up with little or no water. Shortly before use, the user can now mix this agent with a defined amount of water.
  • the agent can be made available to the user in a container, for example, with the container only being filled to a certain extent and having a marking on its edge that indicates the amount of water the user has filled the container with target.
  • Other optional components of the agent In addition to the essential components (a), (b) and (c), the agent can also contain other ingredients that are not mandatory.
  • the agents can additionally contain one or more surfactants.
  • surfactants is understood as meaning surface-active substances.
  • 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
  • nonionic surfactants which have no charges but rather strong dipole moments and are strongly hydrated in aqueous solution.
  • Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one -COO (-) - or -SO3 (-) - in the molecule. carry group.
  • 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-acylaminopropyl-N,N-dimethylammonium glycinates, for example coconut acylaminopropyl dimethylammonium glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethylimidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group, and cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • betaines such as the N-alkyl-N,N-dimethylammonium glycinates, for example coconut alkyl dimethylammonium glycinate, N-acylaminopropyl-N,N-dimethylammonium glycinates, for example coconut acy
  • a preferred zwitterionic surfactant is the fatty acid amide derivative known by the INCI name Cocamidopropyl Betaine.
  • Ampholytic surfactants are surface-active compounds which, in addition to a C8-C24 alkyl or acyl group, contain at least one free amino group and at least one -COOH or -SO3H group in the molecule and are capable of forming inner 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, each with about 8 to 24 C -atoms in the alkyl group.
  • amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amido betaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, coconut acylaminoethylaminopropionate and C 12 - C 18 - acylsarcosine.
  • the agents can also additionally contain at least one nonionic surfactant.
  • Suitable nonionic surfactants are alkyl polyglycosides and alkylene oxide adducts 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 they contain, as nonionic surfactants, fatty acid esters of ethoxylated glycerol which have been reacted with at least 2 moles of ethylene oxide.
  • the nonionic 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 agent in question.
  • the agents can also contain at least one cationic surfactant.
  • Cationic surfactants are understood as meaning surfactants, ie surface-active compounds, each with one or more positive charges. Cationic surfactants only contain positive charges. These surfactants are usually made up of a hydrophobic part and a hydrophilic head group, with the hydrophobic part usually consisting of a hydrocarbon skeleton (e.g. consisting of one or two linear or branched alkyl chains), and the positive charge(s) located in the hydrophilic head group.
  • a hydrocarbon skeleton e.g. consisting of one or two linear or branched alkyl chains
  • cationic surfactants are - quaternary ammonium compounds which can carry one or two alkyl chains with a chain length of 8 to 28 carbon atoms as hydrophobic radicals, - quaternary phosphonium salts substituted with one or more alkyl chains with a chain length of 8 to 28 carbon atoms or - tertiary sulfonium salts.
  • the cationic charge can also be part of a heterocyclic ring (eg 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 with esterquats, for example.
  • 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 agent in question.
  • the agents according to the invention can also contain at least one anionic surfactant. Surface-active agents with exclusively anionic charges (neutralized by a corresponding counter-cation) are referred to as anionic surfactants.
  • 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 agent in question. If the agent contains water or is to be mixed with water before use, the agent can then also contain at least one alkalizing agent and/or acidifying agent to adjust the desired pH value.
  • the pH values for the purposes of the present invention are pH values that were measured at a temperature of 22.degree.
  • 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 agent according to the invention are preferably selected from primary amines with a C2-C6-alkyl skeleton which carries at least one hydroxyl group.
  • Preferred alkanolamines are selected from the group formed by 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-aminopropane-1,2-diol, 2-amino-2-methylpropane-1,3-diol.
  • particularly preferred 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 the agent according to the invention contains an alkanolamine selected from 2-aminoethan-1-ol and/or 2-amino-2-methylpropan-1-ol as the alkalizing agent.
  • an amino acid is an organic compound whose structure contains at least one protonatable amino group and at least one —COOH or one —SO3H group.
  • Preferred amino acids are amino carboxylic acids, in particular ⁇ -(alpha)-amino carboxylic acids and ⁇ -amino carboxylic acids, with ⁇ -amino carboxylic acids being particularly preferred.
  • basic amino acids are to be understood as meaning those amino acids which have an isoelectric point pI greater than 7.0.
  • Basic ⁇ -amino carboxylic acids contain at least one asymmetric carbon atom.
  • both possible enantiomers can be used equally as a specific compound or else mixtures thereof, in particular as racemates.
  • the basic amino acids are preferably selected from the group 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.
  • the agent can contain other alkalizing agents, in particular inorganic alkalizing agents.
  • Inorganic alkalizing agents that can be used according to the invention are preferably selected from the group consisting of sodium hydroxide, potassium hydroxide, calcium hydroxide, barium hydroxide, sodium phosphate, potassium phosphate, sodium silicate, sodium metasilicate, potassium silicate, sodium carbonate and potassium carbonate.
  • Very particularly preferred alkalizing agents are ammonia, 2-aminoethan-1-ol (monoethanolamine), 3-aminopropan-1-ol, 4-aminobutan-1-ol, 5-aminopentan-1-ol, 1-aminopropan-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-aminopropane-1,2-diol, 2-amino-2- methylpropane-1,3-diol, arginine, lysine, ornithine, histidine, sodium hydroxide, potassium hydroxide, calcium hydroxide, barium hydroxide, sodium phosphate, potassium phosphate, sodium silicate, sodium metasilicate, potassium silicate, sodium carbonate and potassium carbonate.
  • Acidifying agents familiar to the person skilled in the art are, for example, edible acids, such as citric acid, acetic acid, malic acid or tartaric acid, and dilute mineral acids, such as hydrochloric acid, sulfuric acid or phosphoric acid.
  • the agents can also contain other active substances, auxiliaries and additives, such as thickening polymers, film-forming polymers, structuring agents such as glucose, maleic acid and lactic acid, hair-conditioning compounds such as phospholipids, for example lecithin and cephalins; perfume oils, dimethylisosorbide and cyclodextrins; fiber structure-improving active ingredients, in particular mono-, di- and oligosaccharides such as glucose, galactose, fructose, fructose and lactose; dyes for coloring the agent; anti-dandruff agents such as Piroctone Olamine, Zinc Omadine and Climbazole; amino acids and oligopeptides; Protein hydrolyzates based on animals and/
  • agent (b) additionally contains at least one anionic polymer from the group consisting of copolymers of acrylic acid, copolymers of methacrylic acid, homopolymers or copolymers of acrylic acid esters, homopolymers or copolymers of methacrylic acid esters, homopolymers or copolymers of Acrylic acid amides, homopolymers or copolymers of methacrylic acid amides, vinylpyrrolidone copolymers, vinyl alcohol copolymers, vinyl acetate copolymers, ethylene homopolymers or copolymers, propylene homopolymers or copolymers, styrene homopolymers or copolymers, polyurethanes, the polyester and/or the polyamide.
  • anionic polymer from the group consisting of copolymers of acrylic acid, copolymers of methacrylic acid, homopolymers or copolymers of acrylic acid esters, homopolymers or copolymers of methacrylic acid esters, homo
  • the person skilled in the art will select these further substances in accordance with the desired properties of the agents. With regard to other optional components and the amounts of these components used, express reference is made to the relevant handbooks known to those skilled in the art.
  • the additional active ingredients and auxiliaries 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 composition.
  • Process for coloring keratin materials The agent according to the invention is applied to the keratin materials, in particular to human hair, and is therefore particularly suitable for use in a process for coloring the keratin material.
  • the composition of the first subject matter of the invention is very particularly preferably used in compositions for coloring hair.
  • a second subject of the present invention is therefore a method for dyeing human hair, comprising the following steps in the order given (1) moistening the hair with water, (2) application of an agent as described in detail in the first subject of the invention open-type, onto the moistened hair, (3) allowing the composition to act for a period of from 10 seconds to 30 minutes, preferably from 10 seconds to 15 minutes, and (4) rinsing the hair out with water.
  • the hair is moistened or moistened with water. This can be done by wetting the hair only with water, or the hair is washed with the aid of a shampoo, the shampoo is rinsed out and the composition according to the invention is then applied to the hair which is still damp.
  • the agent is applied in step (2), and the agent according to the invention can be the agent—preferably low in water or anhydrous—that was described in the description of the first subject of the invention.
  • the hydrolysis and the condensation of the silanes initiated by the hydrolysis take place through the moisture present in the hair.
  • the agent according to the invention can also be mixed with water before use.
  • the coloring process according to the invention comprises the mixing of the agent with water as an additional step.
  • a method for dyeing human hair comprising the following steps in the order given (1) Moistening the hair with water, (2) providing an agent, as disclosed in detail in the description of the first subject of the invention, and mixing the agent with water, (3) applying the ready-to-use agent prepared in step (2). the moistened hair, (4) allowing the agent applied in step (3) to take effect for a period of 10 seconds to 30 minutes, preferably 10 seconds to 15 minutes, and (5) rinsing the hair out with water.
  • the agent can be applied to the hair, for example, with the aid of a brush, a brush or a nozzle, or the user can use his gloved hand for this purpose.
  • step (3) or if the agent was previously mixed with water in step (4)—the agent previously applied to the hair acts on the hair for a period of 10 seconds to 30 minutes, preferably 10 seconds to 15 minutes calmly.
  • the effect can be supported by heat.
  • the user or hairdresser can also massage the agent into the hair while it is still taking effect.
  • step (4) - or in step (5) - the agent is then rinsed out of the hair again. Rinsing can be done with water, or the hair is rinsed with water with the aid of a shampoo and/or a conditioner.
  • what was said about the agents according to the invention applies mutatis mutantis.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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  • Veterinary Medicine (AREA)
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Abstract

La présente invention concerne un agent de coloration de matières kératiniques, en particulier de cheveux humains, contenant (a) au moins deux composés organosiliciés différents l'un de l'autre, chaque composé organosilicié étant indépendamment choisi parmi les silanes avec un, deux ou trois atomes de silicium, et le composé organosilicié comprenant un ou plusieurs groupes hydroxyle et/ou groupes hydrolysables par molécule ; (b) au moins un pigment ; et (c) au moins un composant gras liquide à 20°C et/ou un solvant organique. L'invention concerne également un procédé de coloration de matières kératiniques dans lequel l'agent revendiqué est utilisé.
EP22701884.3A 2021-02-05 2022-01-12 Agent de coloration de matières kératiniques, contenant au moins deux composés organosiliciés différents l'un de l'autre, au moins un pigment et au moins un composant gras liquide et/ou un solvant Pending EP4288156A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102021201097.0A DE102021201097A1 (de) 2021-02-05 2021-02-05 Mittel zum Färben von keratinischem Material, enthaltend mindestens zwei voneinander verschiedene organische Siliciumverbindungen, mindestens ein Pigment und mindestens einen flüssigen Fettbestandteil und/oder ein Lösungsmittel
PCT/EP2022/050557 WO2022167185A1 (fr) 2021-02-05 2022-01-12 Agent de coloration de matières kératiniques, contenant au moins deux composés organosiliciés différents l'un de l'autre, au moins un pigment et au moins un composant gras liquide et/ou un solvant

Publications (1)

Publication Number Publication Date
EP4288156A1 true EP4288156A1 (fr) 2023-12-13

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EP22701884.3A Pending EP4288156A1 (fr) 2021-02-05 2022-01-12 Agent de coloration de matières kératiniques, contenant au moins deux composés organosiliciés différents l'un de l'autre, au moins un pigment et au moins un composant gras liquide et/ou un solvant

Country Status (6)

Country Link
US (1) US20240099953A1 (fr)
EP (1) EP4288156A1 (fr)
JP (1) JP2024506878A (fr)
CN (1) CN116897037A (fr)
DE (1) DE102021201097A1 (fr)
WO (1) WO2022167185A1 (fr)

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2573052T3 (es) 2008-09-30 2016-06-03 L'oreal Composición cosmética integrada por un compuesto orgánico de silicio, -con al menos una función básica-, un polímero filmógeno hidrófobo, un pigmento y un solvente volátil
DE102019204802A1 (de) * 2019-04-04 2020-10-08 Henkel Ag & Co. Kgaa Erhöhung der Stabilität von Mitteln zur Behandlung von Keratinmaterial
DE102019206912A1 (de) * 2019-05-13 2020-11-19 Henkel Ag & Co. Kgaa Verfahren zum Färben von keratinischem Material, umfassend die Anwendung von einer siliciumorganischen Verbindung, einer farbgebenden Verbindung, eines modifizierten Fettsäureesters und eines filmbildenden Polymers I
DE102019206915A1 (de) * 2019-05-13 2020-11-19 Henkel Ag & Co. Kgaa Verfahren zum Färben von keratinischem Material, umfassend die Anwendung einer siliciumorganischen Verbindung, einer farbgebenden Verbindung, eines modifizierten Fettsäureesters und eines filmbildenden Polymers II
DE102019207062A1 (de) * 2019-05-15 2020-11-19 Henkel Ag & Co. Kgaa Mittel zur Behandlung von keratinischen Fasern enthaltend Silane bestimmter Formeln
FR3099990B1 (fr) * 2019-08-22 2021-07-16 Oreal Procédé de traitement des fibres kératiniques mettant en œuvre une composition comprenant au moins un alcoxysilane de formule (I), au moins un alcoxysilane de formule (II), au moins une silicone à fonction époxy, et optionnellement des pigments et/ou colorants directs
DE102020203096A1 (de) * 2020-03-11 2021-09-16 Henkel Ag & Co. Kgaa Verfahren zum Färben von keratinischem Material, umfassend die Anwendung von einer siliciumorganischen Verbindung, Alginsäure(salz), einer farbgebenden Verbindung und eines Nachbehandlungsmittels
DE102020204541A1 (de) * 2020-04-08 2021-10-14 Henkel Ag & Co. Kgaa Verfahren zum Färben von keratinischem Material, umfassend die Anwendung von einer siliciumorganischen Verbindung, einem Polysaccharid, einer farbgebenden Verbindung und eines Nachbehandlungsmittels

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US20240099953A1 (en) 2024-03-28
JP2024506878A (ja) 2024-02-15
WO2022167185A1 (fr) 2022-08-11
CN116897037A (zh) 2023-10-17
DE102021201097A1 (de) 2022-08-11

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