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EP3873403A1 - Bis(triéthoxysilylpropyl)amines en association avec un aldéhyde - Google Patents

Bis(triéthoxysilylpropyl)amines en association avec un aldéhyde

Info

Publication number
EP3873403A1
EP3873403A1 EP19797676.4A EP19797676A EP3873403A1 EP 3873403 A1 EP3873403 A1 EP 3873403A1 EP 19797676 A EP19797676 A EP 19797676A EP 3873403 A1 EP3873403 A1 EP 3873403A1
Authority
EP
European Patent Office
Prior art keywords
group
organic silicon
keratinous material
cosmetic agent
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP19797676.4A
Other languages
German (de)
English (en)
Inventor
Rene Krohn
Erik Schulze Zur Wiesche
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 EP3873403A1 publication Critical patent/EP3873403A1/fr
Pending legal-status Critical Current

Links

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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/25—Silicon; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • 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
    • A61K8/347—Phenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • 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
    • 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
    • A61Q5/004—Preparations used to protect coloured hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes

Definitions

  • the present invention relates to cosmetic compositions for treating a keratinous material, the composition comprising an organic silicon compound as a first component and a second component
  • Component comprises an aldehyde, and the use of the cosmetic agent.
  • bleaching agents which bring about an oxidative brightening of the hair by breaking down the natural hair dyes
  • hair dyes there are essentially three types of hair dye in the area of hair dyeing: So-called oxidation dyes are used for permanent, intensive dyeings with corresponding fastness properties.
  • Such colorants usually contain
  • Oxidation dye precursors so-called developer components and coupler components.
  • Coloring agents or tinting agents which contain so-called direct draws as the coloring component are usually used for temporary dyeings. These are dye molecules that attach directly to the hair and do not require an oxidative process to form the color. These dyeings are generally much more sensitive to shampooing than the oxidative dyeings, so that a much undesired shift in nuances or even a visible "discoloration" occurs much more quickly.
  • precursors of the natural hair dye melanin are applied to the hair; These then form naturally analogous dyes in the hair as part of oxidative processes.
  • 5,6-dihydroxyindoline is used as
  • Coloring can take place with atmospheric oxygen as the only oxidizing agent, so that no further oxidizing agents have to be used.
  • an undesirable coloring of skin areas can occur when rinsing out the hair dye. This effect can also result in lighter "highlights” being recolored by the hair color when washing out, or the dye when washing out from darker “highlights” stains the lighter base hair.
  • the washing out of dyes is generally associated with the disadvantage that the originally desired color changes. Hair colors with red or blue tones in particular have a shorter residence time in the hair, so that washing them out leads to undesirable colors. This problem is also addressed by
  • Air pollutants include polycyclic aromatic hydrocarbons, volatile organic ones
  • the object underlying the present invention is to provide a product with an improved care and / or protective effect.
  • the object of the present invention was to provide a cosmetic agent which brings about effective color protection.
  • a cosmetic agent for the treatment of a keratinous material comprising
  • a keratinous material means hair, skin, nails (such as fingernails and / or toenails). Wool, furs and feathers also fall under the definition of keratinous material.
  • a keratin material is preferably understood to mean human hair, human skin and human nails, in particular fingernails and toenails.
  • Keratinous material is very particularly preferably understood to mean human hair, in particular scalp and / or whiskers.
  • the cosmetic agent for treating a keratinous material contains at least one organic silicon compound as the first constituent essential to the invention.
  • Preferred organic silicon compound as the first constituent essential to the invention.
  • Silicon compounds are selected from silanes with one, two or three silicon atoms, the organic silicon compound comprising one or more hydroxyl groups and / or hydrolyzable groups per molecule.
  • Organic silicon compounds which are also referred to alternatively as organosilicon compounds, are compounds which either have a direct silicon-carbon bond (Si-C) or in which the carbon is attached to the silicon via an oxygen, nitrogen or sulfur atom. Atom is attached.
  • the organic silicon compounds are compounds that contain one to three silicon atoms.
  • the organic silicon compounds particularly preferably contain one or two
  • silane stands for a group of substances that are based on a silicon framework and hydrogen.
  • the hydrogen atoms are completely or partially replaced by organic groups, such as (substituted) alkyl groups and / or alkoxy groups. Some of the hydrogen atoms in the organic silanes can also be replaced by hydroxyl groups.
  • the agent for treating a keratinous material contains at least one organic compound
  • Silicon compound which is preferably selected from silanes with one, two or three silicon atoms, wherein the organic silicon compound comprises one or more hydroxyl groups or hydrolyzable groups per molecule.
  • the agent for treating a keratinous material has at least one organic silicon compound selected from silanes with one, two or three silicon atoms, the organic silicon compound also having one or more basic groups 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 C -C -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 attached directly to the silicon atom. If, for example, the hydrolyzable group is an ethoxy group, the organic silicon compound preferably contains a structural unit R'R "R"'Si-0-CH 2 -CH3. The radicals R ', R "and R"' represent the three remaining free valences of the silicon atom.
  • the agent for treating a keratinous material contains at least one organic silicon compound of the formula (I) and / or (II).
  • the compounds of formulas (I) and (II) are organic silicon compounds selected from silanes with one, two or three silicon atoms, the organic silicon compound comprising one or more hydroxyl groups and / or hydrolyzable groups per molecule.
  • the agent for treating a keratinous material contains at least one organic silicon compound of the formula (I) and / or (II),
  • Ri, R both represent a hydrogen atom
  • L represents a linear, double-bonded Ci-Co alkylene group, preferably a propylene group (-CH -CH -CH -) or an ethylene group (-CH -CH -),
  • R3, R4 independently of one another represent a methyl group or an ethyl group, a represents the number 3 and
  • R5, R5 ', R5 "independently of one another represent a hydrogen atom or a C -C - alkyl group
  • R6, R6 'and R6 "independently of one another represent a Ci-C6-alkyl group
  • A, A ', A ", A"' and A “" independently of one another represent a linear or branched, double-bonded Ci-C 2 o-alkylene group
  • R and Re independently of one another represent a hydrogen atom, a Ci-C6-alkyl group, a hydroxy-Ci-C6-alkyl group, a C -C -alkenyl group, an amino-Ci-C6-alkyl group or a grouping of the formula (III) stand
  • - d stands for the integer 3 - c, - c 'represents an integer from 1 to 3,
  • Ci-Ce alkyl group examples are the groups methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl and t-butyl, n-pentyl and n-hexyl.
  • Propyl, ethyl and methyl are preferred alkyl radicals.
  • Examples of a C -C alkenyl group are vinyl, allyl, but-2-enyl, but-3-enyl and isobutenyl, preferred C -C-alkenyl radicals are vinyl and allyl.
  • a hydroxy-Ci-C6-alkyl group are a hydroxymethyl, a 2-hydroxyethyl, a 2-hydroxypropyl, a 3-hydroxypropyl, a 4-hydroxybutyl group, a 5-hydroxypentyl and a 6-hydroxyhexyl group; a 2-hydroxyethyl group is particularly preferred.
  • Examples of an amino-Ci-C6-alkyl group are the aminomethyl group, the 2-aminoethyl group, the 3-aminopropyl group. The 2-aminoethyl group is particularly preferred.
  • Examples of a linear double-bonded Ci-C o-alkylene group are, for example, the methylene group (-CH -), the ethylene group (-CH -CH -), the propylene group (-CH -CH -CH -) and the butylene group (-CH -CH -CH - CH -).
  • the propylene group (-CH -CH -CH -) is particularly preferred.
  • divalent alkylene groups can also be branched. Examples of branched, double-bonded C -C -AI kyle ng ru ppen are (-CH 2 -CH (CH 3 ) -) and (-CH 2 -CH (CH 3 ) -CH -).
  • R 1 R 2 NL-Si (OR 3 ) a (R4) b (I) the radicals Ri and R independently of one another represent a hydrogen atom or a Ci-Ce alkyl group.
  • the organic silicon compound In the middle part of the organic silicon compound is the structural unit or the linker -L- which stands for a linear or branched, double-bonded Ci-C 2 o-alkylene group.
  • -L- preferably represents a linear, double-bonded Ci-C 2 o-alkylene group. More preferably, -L- stands for a linear double-bonded Ci-Cs-alkylene group. Particularly preferably, -L- stands for a methylene group (-CH -), an ethylene group (-CH -CH -), a propylene group (-CH -CH -CH -) or a butylene group (-CH - CH 2 -CH 2 -CH 2 -). L very particularly preferably represents a propylene group (-CH 2 -CH 2 -CH 2 -).
  • the radical R represents a hydrogen atom or a Ci-C6-alkyl group
  • the radical R represents a Ci-Ce-alkyl group.
  • R and R particularly preferably independently of one another represent a methyl group or an ethyl group.
  • a stands for an integer from 1 to 3, and b stands for the integer 3 - a. If a stands for the number 3, then b is 0. If a stands for the number 2, then b is 1. If a stands for the number 1, then b is 2.
  • the agent for treating a keratinous material had at least one organic silicon compound of the formula (I ) in which the radicals R, R independently of one another represent a methyl group or an ethyl group.
  • Organic silicon compounds of the formula (I) are particularly suitable
  • (3-aminopropyl) trimethoxysilane can be purchased from Sigma-Aldrich.
  • (3-Aminopropyl) triethoxysilane is also commercially available from Sigma-Aldrich.
  • the agent for treating a keratinous material contains at least one organic silicon compound of the formula (II)
  • organosilicon compounds of the formula (II) each carry the silicon-containing groups (RsO) c (R6) dSi- and -Si (R6 ’) d '(OR5’) c ⁇ at their two ends.
  • each of the radicals e, f, g and h can independently of one another stand for the number 0 or 1, the proviso exists that at least one of the residues e, f, g and h is different from 0.
  • an organic silicon compound of the formula (II) contains at least one group from the group consisting of - (A) - and - [NR7- (A ') j- and - [0- (A ”) j- and - [NR8 - (A '”)] -
  • c stands for an integer from 1 to 3, and d stands for the integer 3 - c. If c stands for the number 3, then d is 0. If c stands for the number 2, then d is 1. If c stands for the number 1, then d is 2.
  • c 'stands for an integer from 1 to 3 and d' stands for the integer 3 - c '. If c 'stands for the number 3, then d' is equal to 0. If c 'stands for the number 2, then d' is equal to 1. If c 'stands for the number 1, then d' is equal to 2.
  • the agent for treating a keratinous material contains at least one organic silicon compound of the formula (II)
  • R5 and R5 'independently of one another represent a methyl group or an ethyl group
  • the radicals e, f, g and h can independently of one another stand for the number 0 or 1, at least one radical from e, f, g and h being different from zero.
  • the abbreviations e, f, g and h therefore define which of the groupings - (A) e - and - [NR7- (A ')] f - and - [0- (A ”)] g - and - [ NR8- (A ”')] h - are located in the middle part of the organic silicon compound of the formula (II).
  • the presence of certain groups has proven to be particularly advantageous in terms of increasing the “anti-pollution” effect. Particularly good results could be obtained if at least two of the residues e, f, g and h stand for the number 1.
  • E and f both very particularly preferably stand for the number 1.
  • g and h both very particularly preferably stand for the number 0.
  • the radicals A, A ', A “, A”' and A “” independently of one another stand for a linear or branched, double-bonded Ci-C 2 o-alkylene group.
  • the radicals A, A ', A “, A”' and A “” independently of one another stand for a linear, double-bonded Ci-C 2 o-alkylene group.
  • the radicals A, A ', A ", A"' and A "" are more preferably independently of one another a linear double-bonded Ci-Ce alkylene group.
  • the radicals A, A ', A “, A”' and A “” are particularly preferably independently of one another a methylene group (- CH2-), an ethylene group (-CH2-CH2-), a propylene group (-CH2-CH2-CH2 -) or a butylene group (-CH2-CH2-CH2-).
  • the radicals A, A ', A ", A"' and A “” very particularly preferably represent a propylene group (-CH2-CH2-CH2-).
  • the organic silicon compound of the formula (II) contains a structural grouping - [NR7- (A ')] -.
  • the organic silicon compound of the formula (II) contains a structural grouping - [NRs- (A ”')] -.
  • radicals R and Rs independently of one another represent a hydrogen atom, a C 1 -C6-alkyl group, a hydroxy-Ci-C6-alkyl group, a C 2 -C6-alkenyl group, an amino-Ci-C6-alkyl group or a grouping of Formula (III)
  • the radicals R7 and Rs very particularly preferably independently of one another represent 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).
  • the agent for treating a keratinous material contains an organic silicon compound with 3 reactive silane groups.
  • the agent for treating a keratinous material contains at least one organic silicon compound of the formula (II)
  • R7 represents a hydrogen atom, a methyl group, a 2-hydroxyethyl group, a 2-alkenyl group, a 2-aminoethyl group or a group of the formula (III).
  • the agent for treating a keratinous material contains at least one organic silicon compound of the formula (II), wherein
  • a and A 'independently of one another represent a methylene group (-CH -), an ethylene group (-CH -CH -) or a propylene group (-CH -CH -CH),
  • - R represents 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).
  • Bis (trimethoxysilylpropyl) amine with CAS number 82985-35-1 can be purchased, for example, from Sigma-Aldrich.
  • Bis [3- (triethoxysilyl) propyl] amine also referred to as 3- (triethoxysilyl) -N- [3- (triethoxysilyl) propyl] -1-propanamine, with the CAS number 13497-18-2 can be obtained, for example, from Sigma -Aldrich can be purchased or is commercially available from Evonik under the Dynasylan 1122 product name.
  • N-Methyl-3- (trimethoxysilyl) -N- [3- (trimethoxysilyl) propyl] -1-propanamine is alternatively also referred to as bis (3-trimethoxysilylpropyl) -N-methylamine and can be purchased commercially from Sigma-Aldrich or Fluorochem .
  • Treatment of a keratinous material contains at least one organic silicon compound of the formula (IV)
  • the compounds of formula (IV) are organic silicon compounds selected from silanes with one, two or three silicon atoms, the organic silicon compound comprising one or more hydroxyl groups and / or hydrolyzable groups per molecule.
  • organic silicon compound (s) of the formula (IV) can also be referred to as silanes of the alkylalkoxysilane or alkylhydroxysilane type,
  • R represents a hydrogen atom or a Ci-Ce alkyl group
  • R represents a C 1 -C 6 -alkyl group
  • the agent for treating a keratinous material contains, in addition to the organic silicon compound (s) of the formula (I), at least one further organic silicon compound of the formula (IV)
  • R 9 represents a CiC- alkyl group
  • R represents a hydrogen atom or a C 1 -C 6 -alkyl group
  • - R represents a Ci-Ce alkyl group
  • the agent for treating a keratinous material contains, in addition to the organic silicon compound (s) of the formula (II), at least one further organic silicon compound of the formula (IV)
  • Rg stands for a Ci-Ci alkyl group
  • Rio represents a hydrogen atom or a Ci-Ce alkyl group
  • R represents a C 1 -C 6 -alkyl group
  • the agent for treating a keratinous material contains, in addition to the organic silicon compounds of the formula (I) and (II), at least one further organic silicon compound of the formula (IV)
  • Rg stands for a Ci-Ci alkyl group
  • Rio represents a hydrogen atom or a Ci-Ce alkyl group
  • - R represents a Ci-Ce alkyl group
  • the radical R 9 represents a Ci-Ci-alkyl group.
  • This Ci-Ci alkyl group is saturated and can be linear or branched.
  • R9 preferably represents a linear Ci-Cs-alkyl group.
  • Rg preferably represents a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-octyl group or an n-dodecyl group.
  • R 9 particularly preferably represents a methyl group, an ethyl group or an n-octyl group.
  • the radical Rio represents a hydrogen atom or a Ci-C6-alkyl group. Rio particularly preferably represents a methyl group or an ethyl group.
  • the radical Rn stands for a Ci-C6-alkyl group.
  • Rn particularly preferably represents a methyl group or an ethyl group.
  • k stands for an integer from 1 to 3, and m stands for the integer 3 - k. If k stands for the number 3, then m is 0. If k stands for the number 2, then m is 1. If k stands for the number 1, then m is 2.
  • a very high “anti-pollution” effect could be obtained if the agent for treating a keratinous material contains at least one organic silicon compound of the formula (IV), in which the rest k stands for the number 3. In this case, the remainder m stands for the number 0.
  • the agent is an organic silicon compound (3-aminopropyl) triethoxysilane, i.e. an aminopropyltriethoxysilane (AMEO), and / or 3- (triethoxysilyl) -N- [3- (triethoxysilyl) propyl] -1-propanamine, i.e. a bis (triethoxysilylpropyl) amine.
  • 3-aminopropyl triethoxysilane i.e. an aminopropyltriethoxysilane (AMEO)
  • 3- (triethoxysilyl) -N- [3- (triethoxysilyl) propyl] -1-propanamine i.e. a bis (triethoxysilylpropyl) amine.
  • the organic one is organic one
  • an agent is characterized in that it contains at least one organic silicon compound of the formula (I) and at least one organic silicon compound of the formula (IV).
  • an agent is characterized in that it contains at least one organic silicon compound of the formula (I) which is from the group is selected from (3-aminopropyl) triethoxysilane and (3-aminopropyl) trimethoxysilane, and additionally contains at least one organic silicon compound of the formula (IV) which is selected from the group consisting of methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, hexyltrimethoxysilane, propyltrimethoxysilane, propyltrimethoxysilane, propyltrimethoxysilane, propyltrimethoxysilane, propyltrimethoxysilane, propyltrimethoxysilane, propyltrimethoxysilane, propyltrimethoxysilane, propyltrimethoxysilane, propyltrimethoxysi
  • an agent is characterized in that the agent contains - based on the total weight of the agent:
  • At least one first organic silicon compound which is selected from the group consisting of (3-aminopropyl) trimethoxysilane, (3-aminopropyl) triethoxysilane, (2-aminoethyl) trimethoxysilane, (2-aminoethyl) triethoxysilane , (3-Dimethylaminopropyl) trimethoxysilane, (3-Dimethylaminopropyl) triethoxysilane (2-Dimethylaminoethyl) trimethoxysilane and (2-Dimethylaminoethyl) triethoxysilane, and
  • At least one second organic silicon compound which is selected from the group consisting of methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, propyltrimethoxysilane, propyltriethoxysilane, hexyltrimethoxysilane, hexyltriethoxysilane
  • Silicon compounds with at least one hydroxyl group can react with one another in a condensation reaction. For this reason, both the organosilicon compounds with at least one hydrolyzable group and their hydrolysis and / or condensation products can be present in the agent. When using organosilicon compounds with at least one hydroxyl group, both the organic silicon compounds with at least one hydroxyl group and their condensation products may be present in the agent.
  • a condensation product is understood to mean a product that by reaction of at least two organic silicon compounds, each with at least one hydroxyl group or
  • condensation products can be, for example, dimers, but also trimers or oligomers, the condensation products being in equilibrium with the monomers. Depending on the amount of water used or consumed in the hydrolysis, the balance shifts from monomeric organic silicon compounds to the condensation product.
  • the cosmetic composition for treating a keratinous material contains an aldehyde as further component b).
  • the organic silicon compounds for example (3-aminopropyl) triethoxysilane, ie an aminopropyltriethoxysilane (AMEO), or for example 3- (triethoxysilyl) - N- [3- (triethoxysilyl) propyl] -1-propanamine, ie a bis (triethoxysilylpropyl) amine, is combined with an aldehyde.
  • the aldehyde is one selected from the group consisting of R1-CHO, OHC-R2-CHO, R1-CHOH-CHO and OHC-CHOH-R2-CHOH-CHO, where a -CHO group represents the aldehyde group, R1 represents hydrogen, a linear or branched, saturated or unsaturated alkyl radical with a chain length from C1 to C20, preferably C2 to C15, more preferably C3 to C10, and R2 represents a linear or branched, saturated or unsaturated alkyl radical with a chain length from C1 to C20, preferably represents C2 to C15, more preferably C3 to C10.
  • the -CHOH group includes a hydroxy group attached to the alpha carbon of the carbonyl carbon of the aldehyde.
  • Suitable aldehydes include, for example, methanal, ethanal, propanal, butanal, pentanal, hexanal, heptanal, octanal, nonanal, decanal, undecanal, dodecanal and / or tetradecanal.
  • aldehydes are benzaldehyde, fufural, cinnamaldehyde, tolualdehyde, 4-hydroxy-3-methoxy-benzaldehyde (vanillin), citral, undecen-1-al and / or 4-methoxybenzaldehyde.
  • 4-Hydroxy-3-methoxy-benzaldehyde (vanillin) is particularly preferably used as the aldehyde.
  • Aminopropyltriethoxysilane (AMEO) and / or the bis (triethoxysilylpropyl) amine on the other hand is particularly powerful in terms of a nourishing and protective effect.
  • these combinations each show a high level of color protection in the case of colored keratinous material.
  • organosilicon compound in particular (3-aminopropyl) triethoxysilane and / or bis (triethoxysilylpropyl) amine, protects hair dyed with aldehydes from washing out.
  • the hair surface is made more hydrophobic, and the cosmetic acceptance in terms of softness and combability is significantly increased.
  • the denaturation temperature or the tension-elongation behavior are improved and the hair swelling is reduced. These parameters indicate that the hair structure approximates the natural starting state before chemical treatment.
  • the pH of the cosmetic agent is in the range from 1 to 9, preferably from 1.5 to 8, more preferably from 2 to 7, more preferably from 2.5 to 6, most preferably from 3 to 5.
  • component b) comprising the aldehyde is used in the cosmetic composition with a further skin moisturizing agent.
  • the further Skin moisturizer is selected from the group consisting of glycerin, urea,
  • Amino acid derivatives natural betaine compounds, lactic acid, lactates, especially sodium lactate, and / or ethylhexyloxyglycerol.
  • the selection of these further skin moisturizers increases the nourishing character of the cosmetic agent.
  • the aldehyde is in an amount of 0.01 to 10% by weight, preferably 0.05 to 8% by weight, more preferably 0.075 to 6% by weight, most preferably of 0.1 to 4 wt .-%, based on the total weight of the cosmetic agent, contained in the cosmetic agent.
  • the agent for treating a keratinous material can in particular comprise an agent for cleaning a keratinous material, an agent for maintaining a keratinous material, an agent for maintaining and cleaning a keratinous material and / or an agent for temporarily reshaping a keratinous material.
  • the agent for treating a keratinous material further comprises 0.001 to 20% by weight of at least one quaternary compound. This applies in particular to agents for the care of a keratinous material and agents for the care and cleaning of a keratinous material.
  • the at least one quaternary compound is selected from at least one of the groups consisting of
  • Carbon atoms and A stands for a physiologically acceptable anion, and / or
  • the hair treatment composition contains a cationic homopolymer, which falls under the INCI name Polyquaternium-37, as quaternary compounds.
  • the agent for treating a keratinous material further comprises a setting compound, preferably selected from the group consisting of waxes, synthetic polymers and mixtures thereof.
  • a large number of synthetic polymers have already been developed as strengthening compounds which are used in the agent for treating a keratinous material Material can be used.
  • waxes are used as strengthening compounds.
  • the polymers and / or waxes when used on the keratinous material result in a polymer film or film which on the one hand gives the hairstyle a strong hold, but on the other hand is sufficiently flexible so that it does not break under stress.
  • the synthetic polymers can be divided into cationic, anionic, nonionic and amphoteric setting polymers.
  • Suitable synthetic polymers include, for example, polymers with the following INCI names: Acrylamide / Ammonium Acrylate Copolymer, Acrylamides / DMAPA Acrylates / Methoxy PEG Methacrylate Copolymer, Acrylamidopropyltrimonium Chloride / Acrylamide Copolymer,
  • Acrylamidopropyltrimonium Chloride / Acrylates Copolymer Acrylates / Acetoacetoxyethyl Methacrylate Copolymer, Acrylates / Acrylamide Copolymer, Acrylates / Ammonium Methacrylate Copolymer, Acrylates / t-Butylacrylamide Copolymer, Acrylates Copolymer, Acrylates / C1 -2 Succinates / Hydroxyacrylates Copolymer, Acrylates / Lauryl Acrylate / Stearyl Acrylate / Ethylamine Oxide Methacrylate Copolymer, Acrylates / Octylacrylamide Copolymer, Acrylates / Octylacrylamide / Diphenyl Amodimethicone Copolymer, Acrylates / Stearyl Acrylate / Ethylamine Oxide Methacrylate Copolymer, Acrylates / VA Copolymer, Acrylates / Hydroxyesters Ac
  • Polyacrylate-6 Polybeta-Alanine / Glutaric Acid Crosspolymer, Polybutylene Terephthalate, Polyester-1, Polyethylacrylate, Polyethylene Terephthalate, Polymethacryloyl Ethyl Betaine, Polypentaerythrityl Terephthalate, Polyperfluoroperhydrophenanthrene, Polyquaternium-1, Polyquaternium-1
  • Caprolactam / VP / Dimethylaminoethyl Methacrylate Copolymer VP / Acrylates / Lauryl Methacrylate Copolymer, VP / Dimethylaminoethyl methacrylate Copolymer, VP / DMAPA Acrylates Copolymer, VP / Hexadecene Copolymer, VP / VA Copolymer, VP / Vinyl Caprolactam / DMAPA Acrylates Copolymer, Yeast Palmitate and Styrene / VP copolymer.
  • Cellulose ethers such as
  • Hydroxypropyl cellulose hydroxyethyl cellulose and methyl hydroxypropyl cellulose.
  • Homopolyacrylic acid (INCI: Carbomer), which is commercially available under the name Carbopol® in various versions, is also suitable as a setting compound.
  • the setting compound preferably comprises a vinyl pyrrolidone-containing polymer.
  • the setting compound particularly preferably comprises a polymer selected from the group consisting of
  • Another preferred strengthening compound is octylacrylamide / acrylates / butylaminoethyl methacrylate copolymer (INCI), which is sold under the name “Amphomer®” by Akzo Nobel.
  • the setting compound is a synthetic polymer selected from the group consisting of polyvinylpyrrolidone (PVP), vinylpyrrolidone-vinyl acetate copolymer (VP / VA copolymer), vinyl caprolactam / VP / dimethylaminoethyl methacrylate copolymer (INCI), VP / DMAPA Acrylates Copolymer (INCI), Octylacrylamide / Acrylates / Butylaminoethyl Methacrylate Copolymer (INCI) and mixtures thereof.
  • PVP polyvinylpyrrolidone
  • VP / VA copolymer vinyl caprolactam / VP / dimethylaminoethyl methacrylate copolymer
  • VP / DMAPA Acrylates Copolymer INCCI
  • Octylacrylamide / Acrylates / Butylaminoethyl Methacrylate Copolymer INCI
  • the cosmetic agent contains as component d) at least one cationic surfactant.
  • This is particularly preferably a cationic surfactant of the formula (V) XQ
  • Rl2, Rl3, Rl4 independently of one another represent a C1-C6-alkyl group, a C2-C6-alkenyl group or a C2-C6-hydroxyalkyl group,
  • Rl5 stands for a C8-C28-alkyl group, preferably a C10-C22-alkyl group and
  • X- stands for a physiologically compatible anion, and / or the cosmetic agent preferably contains at least one cationic surfactant of the formula (VI),
  • R-ie represents a C1-C6 alkyl group
  • R17, Rl8 independently of one another for a C7-C27-alkyl group, preferably a C10-C22-
  • X- stands for a physiologically compatible anion, and / or the cosmetic agent preferably contains at least one cationic surfactant of the formula (VII),
  • R19, R20 independently of one another represent a C1-C6-alkyl group or a C2-C6-hydroxyalkyl group, R, R independently of one another for a C7-C27-alkyl group, preferably a C10-C22-
  • X- stands for a physiologically compatible anion, and / or the cosmetic agent preferably contains at least one cationic surfactant of the formula (VIII), NR23R24R25 (VIII) in which
  • R23, R24 independently of one another represent a C1-C6-alkyl group, a C2-C6-alkenyl group or a C2-C6-hydroxyalkyl group, and
  • R25 stands for a C8-C28-alkyl group, preferably a C10-C22-alkyl group.
  • the cationic surfactants of the formula (VIII) are amine derivatives, so-called
  • the organic radicals R23, R24 and R25 are bound directly to the nitrogen atom. In the acidic pH range, these are cationized, i.e. the nitrogen atom is then protonated.
  • the physiologically compatible counterions are suitable as counterions. Steamidopropyl dimethylamine is particularly preferred for the cationic surfactants of the formula (VIII).
  • the amount of cationic surfactant is 0.1 to 30% by weight, preferably 0.5 to 20% by weight, more preferably 1 to 10% by weight, based on the total weight of the cosmetic composition .
  • the cationic surfactant comprises a hydrophobic head group with a cationic charge and one or two hydrophobic end parts, the hydrophobic end part or the hydrophobic end parts being straight-chain or branched, saturated or mono- or polyunsaturated alkyl groups, which are preferably one Have chain lengths of C6 to C30, more preferably C8 to C26, particularly preferably C10 to C22.
  • the cationic surfactant has an ester function, an ether function, a ketone function, an alcohol function or an amide function.
  • one or more anionic surfactants are contained in the cosmetic agent, which is preferably selected from the group consisting of
  • linear alpha-olefin sulfonates having 8 to 24, preferably 12 to 22, more preferably 16 to 18 carbon atoms,
  • R9-0- (CH 2 -CH 2 0) n-S03X in which R is preferably a straight-chain or branched, saturated or mono- or polyunsaturated alkyl or alkenyl radical having up to 24, preferably 12 to 22, more preferably 16 to 18 carbon atoms, n for 0 or 1 to 12, more preferably 2 to 4 and X for an alkali or alkaline earth metal ion or for protonated
  • Triethanolamine or the ammonium ion Triethanolamine or the ammonium ion
  • Alkyl isethionate the alkyl group of which is selected from a branched or unbranched C6 to C, preferably C to Cie, more preferably e to C alkyl group, in particular sodium cocoyl isethionate,
  • Alkylglycoside carboxylic acids the alkyl group of which is selected from a branched or unbranched Ce to C, preferably C to C, more preferably C to C alkyl group,
  • Alkyl sulfosuccinates the two alkyl groups of which are selected from the same or different, branched or unbranched C to C, preferably C to C, more preferably C6 to Cs alkyl groups,
  • alkyl thaw whose alkyl group is selected from a branched or unbranched Ce to C, preferably C to Cis, more preferably C to Cie alkyl group,
  • Alkyl sarcosinates the alkyl group of which is selected from a branched or unbranched C6 to C, preferably C to Cie, more preferably C to C alkyl group,
  • the counter ion of the anionic surfactant is an alkali or alkaline earth metal ion or a protonated triethanolamine or the ammonium ion.
  • anionic surfactants are straight-chain or branched alkyl ether sulfates which contain an alkyl radical with 8 to 18 and in particular with 10 to 16 C atoms and 1 to 6 and in particular 2 to 4 ethylene oxide units.
  • the surfactant mixture of anionic and amphoteric / zwitterionic surfactants very particularly preferably contains sodium lauryl ether sulfate (INCI: Sodium Laureth Sulfate) and very particularly preferably sodium lauryl ether sulfate with 2 ethylene oxide units.
  • Amphoteric surfactants which are also referred to as zwitterionic surfactants, are those surface-active compounds which carry at least one quaternary ammonium group and at least one -COO - or -SO group in the molecule.
  • Amphoteric / zwitterionic surfactants are also understood to mean those surface-active compounds which, in addition to a Ce -Alkyl- or - acyl group contain at least one free amino group and at least one -COOH or -SOaH group and are capable of forming internal salts.
  • amphoteric surfactants in the cosmetic composition are selected from the group consisting of
  • Alkyl betaine comprising at least one saturated or unsaturated, branched or unbranched C6 to C, preferably C to Cie, more preferably C to Cie alkyl group,
  • Alkyl amphodiacetate or alkyl amphodiacetate comprising a saturated or unsaturated, branched or unbranched C6 to C, preferably C to Cie, more preferably C to Cie alkyl group, with an alkali or alkaline earth metal counterion, and Alkylamidopropylbetaine, comprising at least one saturated or unsaturated, branched or unbranched Ce to C, preferably C to C, more preferably C to C alkyl group.
  • amphoteric / zwitterionic surfactants include the surfactants known under the INCI name cocamidopropyl betaine and disodium cocoamphodiacetate.
  • the nonionic surfactant is selected from the group consisting of
  • Alkylglucamide comprising a saturated or unsaturated, branched or unbranched C6 to C, preferably C to Cie, more preferably C to Cie alkyl group,
  • Alkylfructoside comprising a saturated or unsaturated, branched or unbranched Ob to C, preferably C to C, more preferably C to Cie alkyl group,
  • Alkyl glucoside comprising a saturated or unsaturated, branched or unbranched Ce to C, preferably C to Cie, more preferably C to Cie alkyl group,
  • the cosmetic agent contains two structurally different surfactants. It is particularly preferred that the cosmetic agent contains two structurally different surfactants, preferably the cosmetic agent contains two structurally different cationic surfactants, or the cosmetic agent contains a cationic surfactant and a nonionic surfactant.
  • the cosmetic composition can contain at least one natural or synthetic wax, which has a melting point of over 37 ° C., as a setting compound.
  • Solid paraffins or isoparaffins plant waxes such as candelilla wax, carnauba wax, esparto grass wax, Japanese wax, cork wax, sugar cane wax, ouricury wax, montan wax, sunflower wax, fruit waxes and animal waxes, such as bees waxes and other insect waxes, wool wax and shellac wax, can be used as natural or synthetic waxes Bürzelfett, further mineral waxes, such as ceresin and ozokerite or the petrochemical waxes, such as petrolatum, paraffin waxes, microwaxes made of polyethylene or polypropylene and
  • Polyethylene glycol waxes are used. It can be advantageous to use hydrogenated or hardened waxes. Furthermore, chemically modified waxes, in particular hard waxes, for example montan ester waxes, Sasol waxes and hydrogenated jojoba waxes, can also be used.
  • the triglycerides of saturated and optionally hydroxylated C16-30 fatty acids such as, for example, hydrogenated triglyceride fats (hydrogenated palm oil, hydrogenated coconut oil, hydrogenated castor oil), glyceryl tribehenate or glyceryl tri-12-hydroxystearate, are also suitable in the cosmetic compositions.
  • the wax components can also be selected from the group of the esters from saturated, unbranched alkane carboxylic acids with a chain length of 22 to 44 carbon atoms and saturated, unbranched alcohols with a chain length of 22 to 44 carbon atoms, provided that the wax component or all of the wax components at room temperature are firm.
  • Silicone waxes for example stearyltrimethylsilane / stearyl alcohol, may also be advantageous.
  • Natural, chemically modified and synthetic waxes can be used alone or in combination. This means that several waxes can also be used. Furthermore, a number of wax mixtures, possibly mixed with other additives, are commercially available.
  • special wax 7686 OE a mixture of cetyl palmitate, beeswax, microcrystalline wax and polyethylene with a melting range of 73-75 ° C; manufacturer: Kahl &
  • Polywax® GP 200 (a mixture of stearyl alcohol and polyethylene glycol stearate with a melting point of 47-51 ° C; manufacturer: Croda) and "Weichceresin® FL 400" (a
  • Vaseline / Vaseline oil / wax mixture with a melting point of 50-54 ° C; Manufacturer: Parafluid Mineralölgesellschaft) are examples of mixtures that can be used.
  • the wax is preferably selected from carnauba wax (INCI: Copernicia Cerifera Cera) beeswax (INCI: Beeswax), petrolatum (INCI), microcrystalline wax and in particular mixtures thereof.
  • Preferred mixtures include the combination of carnauba wax (INCI: Copernicia Cerifera Cera), petrolatum and microcrystalline wax or the combination of beeswax (INCI: Beeswax) and petrolatum.
  • the wax or wax components should be solid at 25 ° C and should melt in the range of> 37 ° C.
  • the agent for treating a keratinous material preferably contains the setting compound in a total amount of 0.5 to 50% by weight, preferably 1 to 40% by weight, more preferably 1.5 to 30% by weight, even more preferably 2 to 25 wt .-%, based on the total weight of the cosmetic composition.
  • suitable ingredients include nonionic polymers, anionic polymers, (further) cationic polymers, waxes, protein hydrolyzates, amino acids, oligopetides, vitamins, provitamins, vitamin precursors, betaines, bioquinones, purine (derivatives), care substances, plant extracts, silicones, ester oils, UV light protection filters , Structuring agents, thickeners, electrolytes, pH adjusting agents, swelling agents, Dyes, antidandruff agents, complexing agents, opacifiers, pearlescent agents, pigments, stabilizing agents, blowing agents, antioxidants, perfume oils and / or preservatives.
  • the preferred organic silicon compounds are combined with the preferred aldehyde 4-hydroxy-3-methoxy-benzaldehyde (vanillin) in an agent according to the invention.
  • the active ingredient combination of at least one organic silicon compound and an aldehyde can already be contained in the agent for the treatment of a keratinous material.
  • the agent for treating a keratinous material is already sold in a form ready for use.
  • the agent itself is preferably packaged with little or no water.
  • the at least one organic silicon compound is comprised of a maximum of 12 hours, preferably a maximum of 6 hours, more preferably a maximum of 3 hours, even more preferably a maximum of 1 hour before the agent for treating a keratinous material Ingredients of the agent for the treatment of a keratinous material added with the exception of the at least one organic silicon compound.
  • the organic silicon compound and a further component b) are only added to a cosmetic product shortly before use, i.e. 1 minute to 12 hours, preferably 2 minutes to 6 hours, particularly preferably 1 minute to 3 hours, particularly preferably 1 minute to 1 hour.
  • the organosilicon compound for example the AMEO or the bis (triethoxysilylpropyl) amine
  • the organosilicon compound for example the AMEO or the bis (triethoxysilylpropyl) amine
  • the user can stir or spill an agent (a) which contains the organic silicon compound (s) with an agent ( ⁇ ) which comprises the remaining ingredients of the agent for treating a keratinous material.
  • agent (a) which contains the organic silicon compound (s)
  • agent ( ⁇ ) which comprises the remaining ingredients of the agent for treating a keratinous material.
  • the user can now apply this mixture of (a) and (ß) to the keratinous materials - either directly after their production or after a short reaction time of 1 minute to 20 minutes.
  • the agent (ß) can contain water, in particular water in an amount> 30 wt .-%, based on the total weight of the agent for the treatment of keratinous materials.
  • Another object of the present application is the use of a cosmetic agent according to the invention for the treatment of a keratinous material, for the care of keratinous material, for reducing and / or preventing the washing out of color in the case of colored keratinous material and / or for hydrophobizing the surface of keratinous material.

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  • General Health & Medical Sciences (AREA)
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Abstract

La présente invention concerne une composition de principes actifs pour le soin des cheveux humains. L'invention concerne en particulier un produit cosmétique destiné au traitement d'une matière kératinique, qui comprend a) au moins un composé de silicium organique et b) un aldéhyde, ledit produit cosmétique étant particulièrement approprié comme produit de protection de la couleur.
EP19797676.4A 2018-10-31 2019-10-31 Bis(triéthoxysilylpropyl)amines en association avec un aldéhyde Pending EP3873403A1 (fr)

Applications Claiming Priority (2)

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DE102018127199.9A DE102018127199A1 (de) 2018-10-31 2018-10-31 Bis(triethoxysilylpropyl)amine in Kombination mit einem Aldehyd
PCT/EP2019/079775 WO2020089361A1 (fr) 2018-10-31 2019-10-31 Bis(triéthoxysilylpropyl)amines en association avec un aldéhyde

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WO (1) WO2020089361A1 (fr)

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DE102019210983A1 (de) * 2019-07-24 2021-01-28 Henkel Ag & Co. Kgaa Erhöhung der Stabilität von Mitteln zur Behandlung von Keratinmaterial

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CN1937996B (zh) * 2004-04-07 2012-04-18 花王株式会社 毛发处理剂和毛发处理方法
FR2922759B1 (fr) * 2007-10-31 2015-04-10 Oreal Composition coloration directe non eclaircissante comprenant un compose aminosilicie et procede de coloration de fibres keratiniques humaines la mettant en oeuvre
FR2922760B1 (fr) * 2007-10-31 2009-11-20 Oreal Eclaircissement et/ou coloration de fibres keratiniques humaines au moyen d'une composition comprenant un compose aminosilicie particulier et composition et dispositif
FR2944963B1 (fr) * 2009-04-30 2011-05-27 Oreal Eclaircissement et/ou coloration de fibres keratiniques humaines au moyen d'une composition aqueuse comprenant un amino-trialcoxy silane ou -trialcenyloxy silane
FR2954142B1 (fr) * 2009-12-18 2012-04-13 Oreal Procede de traitement cosmetique impliquant un compose apte a condenser in situ
WO2012055805A1 (fr) 2010-10-26 2012-05-03 L'oreal Composition cosmétique comprenant un alcoxysilane à chaîne grasse et agent cosmétique siliceux
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DE102018127199A1 (de) 2020-04-30
JP7541528B2 (ja) 2024-08-28
JP2022509431A (ja) 2022-01-20
US20210393498A1 (en) 2021-12-23
WO2020089361A1 (fr) 2020-05-07

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