EP3873417A1 - Composition de principes actifs pour la modification de la surface des cheveux et la modification de la forme de la chevelure - Google Patents

Composition de principes actifs pour la modification de la surface des cheveux et la modification de la forme de la chevelure

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Publication number
EP3873417A1
EP3873417A1 EP19797669.9A EP19797669A EP3873417A1 EP 3873417 A1 EP3873417 A1 EP 3873417A1 EP 19797669 A EP19797669 A EP 19797669A EP 3873417 A1 EP3873417 A1 EP 3873417A1
Authority
EP
European Patent Office
Prior art keywords
group
organic silicon
keratinous material
agent
propyl
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
EP19797669.9A
Other languages
German (de)
English (en)
Inventor
Rene Krohn
Erik Schulze Zur Wiesche
Torsten LECHNER
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 EP3873417A1 publication Critical patent/EP3873417A1/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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
    • 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
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8182—Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • 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
    • A61K8/85—Polyesters
    • 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
    • A61Q5/12—Preparations containing hair conditioners
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/592—Mixtures of compounds complementing their respective functions
    • A61K2800/5922—At least two compounds being classified in the same subclass of A61K8/18
    • 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

  • Active ingredient composition for modifying the hair surface and changing the shape of the hair collective
  • the present invention relates to cosmetic compositions for treating a keratinous material, the composition comprising an organic silicon compound and at least one polycarboxylic acid, and to the use of the cosmetic composition.
  • Air pollutants include polycyclic aromatic hydrocarbons, volatile organic ones
  • Air pollutants can be amplified in the presence of other air pollutants and under the influence of UV radiation or heat.
  • Free radicals are metabolic products that occur naturally in large quantities in the body. They can promote free radicals irritation and inflammation and accelerate the process of aging. In this case, one speaks of "oxidative damage”. Free radicals can also cause hair damage, for example as
  • organosilicon compounds from the group of the silanes which comprise at least one hydroxyl group and / or hydrolyzable group. Due to the
  • 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 the water ultimately leads to the formation of a film when used on a keratinic material, which can develop a protective effect.
  • the object on which the present invention is based is to provide a cosmetic product which enables good shaping of the hair and improves the structural protection against exposure to heat.
  • a cosmetic agent for treating a keratinous material comprising a) at least one organic silicon compound and
  • R1 and R3 independently of one another H, CH 3 , OH, (CH 2 ) n OH, NH 2 , (CH 2 ) NH 2 , COOH,
  • R2 H CHs, OH, (CH 2 ) n OH, NH 2 , (CH 2 ) NH 2 , COOH, (CH 2 ) n COOH, COOX,
  • R4 represents (CH 2 ) n COOH or (CH 2 ) n COOX with n equal to 0 to 6 or 1 to 6, in particular 1,
  • R1, R2, R3, R4 represents an alkali or alkaline earth metal ion or an ammonium ion.
  • 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, where the organic silicon compound comprises 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-Ce) alkylamino group.
  • the hydrolyzable group or groups is preferably a Ci-Co 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. Very particularly good results have been obtained if 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-C6-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 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
  • - e represents 0 or 1
  • - f represents 0 or 1
  • Examples of a C 1 -C 6 -alkyl group are the groups methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl and t-butyl, n-pentyl and n-hexyl. Propyl, ethyl and methyl are preferred alkyl radicals.
  • Examples of a C 2 -C6 alkenyl group are vinyl, allyl, but-2-enyl, but-3-enyl and isobutenyl, preferred C 2 -C6 alkenyl radicals are vinyl and allyl.
  • a hydroxy-Ci-C6-alkyl group are a hydroxymethyl, a 2-hydroxyethyl, a 2-hydroxypropyl, a 3-hydroxypropyl, a 4-hydroxybutyl group, a 5-hydroxypentyl and a 6-hydroxyhexyl group; a 2-hydroxyethyl group is particularly preferred.
  • Examples of an amino-Ci-C6-alkyl group are the aminomethyl group, the 2-aminoethyl group, the 3-aminopropyl group. The 2-aminoethyl group is particularly preferred.
  • Examples of a linear double-bonded Ci-C 2 o-alkylene group are, for example, the methylene group (-CH 2 -), the ethylene group (-CH2-CH2-), the propylene group (-CH2-CH2-) and the butylene group ( -CH2-CH2-CH2-).
  • the propylene group (-CH2-CH2-CH2-) is particularly preferred.
  • divalent alkylene groups can also be branched. Examples of branched, double-bonded C 3 -C 2o-alkylene groups are (-CH 2 -CH (CH 3 ) -) and (-CH 2 -CH (CH 3 ) -CH2-).
  • R 1 R 2 NL-Si (OR 3 ) a (R4) b (I) the radicals R 1 and R 2 independently of one another represent a hydrogen atom or a C 1 -C 6 alkyl group.
  • the radicals R 1 and R 2 both very particularly preferably represent a hydrogen atom.
  • the organic silicon compound In the middle part of the organic silicon compound is the structural unit or the linker -L- which stands for a linear or branched, 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 CrC6 alkylene group. Particularly preferably, -L- stands for a methylene group (-CH 2 -), an ethylene group (-CH 2 -CH 2 -), a propylene group (-CH 2 -CH 2 -CH 2 -) or a butylene group (-CH 2 - CH 2 -CH 2 -CH 2 -). L 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)
  • the organosilicon compounds of the formula (II) have the silicon-containing groups (RsO) c (R6) dSi- and -Si (R6 ’) d '(OR5’) c ⁇ at their two ends.
  • 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 ”') j-
  • the radicals R5, R5', R5 "independently of one another represent a hydrogen atom or a Ci-Ce -Alkyl group.
  • the radicals R6, R6 'and R6 independently of one another represent a Ci-C6-alkyl group.
  • 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 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 - [NRe- (A ’”)] -.
  • radicals R and Re independently of one another represent a hydrogen atom, a Ci-Ce alkyl group, a hydroxy-Ci-Ce alkyl group, a C 2 -Ce alkenyl group, an amino-Ci-Ce alkyl group or a grouping of the formula (III)
  • the radicals R7 and Re 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 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)
  • Rg stands for a C-i-C- 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 represents a Ci-Ci2-alkyl group
  • Rio represents a hydrogen atom or a Ci-Ce alkyl group
  • - R11 represents a Ci-C6-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 represents a Ci-Ci2-alkyl group
  • Rio represents a hydrogen atom or a Ci-Ce alkyl group
  • - R11 represents a Ci-C6-alkyl group
  • the Rg radical represents a Ci-Ci2-alkyl group.
  • This Ci-Ci2-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.
  • Rg 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 represents a Ci-Cß-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.
  • 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 in an explicitly very particularly preferred embodiment, contains at least one organic silicon compound of the formula (I) which is selected from the group consisting of (3-aminopropyl) triethoxysilane and (3-aminopropyl) trimethoxysilane, and additionally at least contains an organic silicon compound of the formula (IV) which is selected from the group consisting of methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, propyltrimethoxysilane, propyltriethoxysilane, hexyltrimethoxysilane and hexyltriethoxysilane.
  • organic silicon compound of the formula (I) which is selected from the group consisting of (3-aminopropyl) triethoxysilane and (3-aminopropyl) trimethoxysilane
  • an organic silicon compound of the formula (IV) which is selected from the
  • 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 Octyltrimethoxysilane, octyltriethoxysilane, dodecyltrimethoxysilane, dodecyltriethoxysilane,
  • 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 is formed by reacting at least two organic silicon compounds with at least one hydroxyl group or hydrolyzable group per molecule, with the elimination of water and / or with the elimination of an alkanol.
  • the 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 agent for treating a keratinous material contains a polycarboxylic acid which is composed of at least one first monomer of the formula (A)
  • R1 and R3 independently of one another H, CH 3 , OH, (CH 2 ) n OH, NH 2 , (CH 2 ) NH 2 , COOH, (CH 2 ) n COOH,
  • COOX (CH 2 ) nCOOX, in particular H, and n from 0 to 6 or from 1 to 6,
  • R2 H, CH 3 , OH, (CH 2 ) n OH, NH 2 , (CH 2 ) NH 2 , COOH, (CH 2 ) n COOH, COOX, (CH 2 ) n COOX with n equal to 0 to 6 or 1 to 6, in particular H, CH3, COOH or COOX, and
  • R4 represents (CH 2 ) n COOH or (CH 2 ) n COOX with n equal to 0 to 6 or 1 to 6, in particular 1, where X in R1, R2, R3, R4 represents an alkali or alkaline earth metal ion or an ammonium ion.
  • the organic silicon compounds in particular 3- (triethoxysilyl) -N- [3- (triethoxysilyl) propyl] -1-propanamine, ie a bis (triethoxysilylpropyl) amine, and / or (3-aminopropyl) triethoxysilane, ie an aminopropyltriethoxysilane (AMEO), is combined with the polycarboxylic acid.
  • the polymer which is composed of at least one unit of the formula (A), is a polycarboxylic acid.
  • R4 represents a carboxylic acid group and R2 represents hydrogen or a methyl group
  • the polycarboxylic acid is polyacrylic acid or polymethacrylic acid.
  • R1 and R3 represent hydrogen
  • R2 represents a carboxylic acid group and R4 represents a (CH) COOH group
  • the polycarboxylic acid is itaconic acid.
  • the polycarboxylic acid should be a homo- or copolymer. In the case of a copolymer, it can be composed of two, three or four different monomers.
  • the acid group (s) of the polycarboxylic acid can be neutralized, partially neutralized or present as a salt of the carboxylic acid.
  • the counterion can in principle be any physiologically acceptable counterion, preferably this comprises an alkali or alkaline earth metal ion or comprises an ammonium ion.
  • the combination of the bis (triethoxysilylpropyl) amine and / or the aminopropyltriethoxysilane with the polycarboxylic acid forms a layer on the hair. This ensures that the hair can be shaped temporarily and a good hairstyle is achieved. In addition, the hair surface in the case of hair damaged by oxidation is rendered hydrophobic again, which leads to the reduction of frizz. In addition, the structural protection against the effects of heat is improved.
  • the amount is
  • Polycarboxylic acid 0.1 to 10% by weight, preferably 0.5 to 8% by weight, more preferably 1 to 6% by weight, based on the total weight of the cosmetic agent, in the cosmetic agent, the amount being calculated on the basis of the free acid, regardless of whether the polycarboxylic acid is present as free acid or (partially) neutralized.
  • the polycarboxylic acid is a homopolymer composed of itaconic acid or a salt of itaconic acid, or the polycarboxylic acid is a copolymer of the formula (B):
  • Mi represents at least one or more different repeat units, which represents one or more different vinyl monomer units, in which X represents hydrogen or an alkali or alkaline earth metal, a the mole fraction of the repeat unit derived from itaconic acid in the copolymer and b the mole fraction of the one or more different
  • Polyitaconic acid homopolymer or a copolymer in which the monomer unit is derived from another monomer Mi in addition to the itaconic acid unit.
  • the monomer unit Mi can also comprise two different monomers.
  • the unit of measure b is then composed of the sum of the unit of measure of the various monomers.
  • An example of such a polymer is PVP / VA / Itaconic Acid Copolymer (INCI).
  • the polycarboxylic acid acts as a film former in the cosmetic agent. This is deposited on the hair and justifies the temporary deformability of the hair.
  • the film former is a homo- or copolymer which is derived from itaconic acid. If the film former is exclusively in the form of polymerized itaconic acid and / or a salt of itaconic acid, the film former forms a homopolymer.
  • the technical production of itaconic acid is conventionally carried out biotechnologically through the submerged fermentation of molasses and other substrates using strains of certain fungi.
  • the monomer for the production of the film former thus represents a raw material that is not
  • the agent for treating a keratinous material may contain, in addition to the polycarboxylic acid, one or more further setting compounds, one of which is the polycarboxylic acid which is mandatory in the cosmetic agent.
  • further setting compounds preferably selected from the group consisting of waxes and / or further synthetic polymers, can be contained in the cosmetic agent. I.e. waxes and / or other synthetic polymers can additionally be used as setting compounds.
  • the polycarboxylic acid and the other strengthening compounds when used on the keratinous material result in a 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 other 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,
  • Diethylenetriamine Copolymer Adipic Acid / Isophthalic Acid / Neopentyl Glycol / Trimethylolpropane Copolymer, Allyl Stearate / VA Copolymer, Aminoethyl Acrylate Phosphate / Acrylates Copolymer,
  • Neodecanoate Copolymer VA / Crotonates / Vinyl Propionate Copolymer, VA / DBM Copolymer, VA / Vinyl Butyl Benzoate / Crotonates Copolymer, Vinylamine / Vinyl Alcohol Copolymer, Vinyl
  • 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.
  • the setting compound preferably comprises a vinylpyrrolidone-containing polymer.
  • the setting compound particularly preferably comprises a polymer selected from the group consisting of
  • the setting compound is a synthetic polymer selected from the group consisting of polyvinylpyrrolidone (PVP), vinylpyrrolidone-vinyl acetate- Copolymer (VP / VA Coplymer), 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 Coplymer vinylpyrrolidone-vinyl acetate- Copolymer
  • VCI Vinyl Caprolactam / VP / Dimethylaminoethyl Methacrylate Copolymer
  • VP / DMAPA Acrylates Copolymer INCCI
  • an octylacrylamide / acrylate / butylaminoethyl methacrylate copolymer can be contained in the cosmetic as a setting polymer.
  • This copolymer is among the
  • the agent for treating a keratinous material can in particular comprise an agent for temporarily reshaping a keratinous material, an agent for cleaning a keratinous material, an agent for maintaining a keratinous material and / or an agent for maintaining and cleaning 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 that give the keratinous material additional care properties.
  • the at least one quaternary compound is selected from at least one of the groups consisting of
  • radicals R independently of one another each represent a saturated or unsaturated, linear or branched hydrocarbon radical with a chain length of 8 to 30
  • Carbon atoms and A stands for a physiologically acceptable anion, and / or
  • quaternized cellulose derivatives in particular Polyquaternium 10, Polyquaternium-24, Polyquaternium-27, Polyquaternium-67, Polyquaternium-72, and / or
  • 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.
  • triglycerides of saturated and optionally hydroxylated C16-30 fatty acids such as, for example, hardened triglyceride fats (hydrogenated palm oil, hydrogenated coconut oil, hydrogenated castor oil), glyceryl tribehenate or glyceryl tri-12-hydroxystearate.
  • 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
  • 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 contains the setting compound, if it does not relate to the polycarboxylic acid used in accordance with the invention, preferably in one
  • 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 , Thickeners, electrolytes, pH adjusting agents, swelling agents, dyes,
  • Antidandruff agents complexing agents, opacifiers, pearlescent agents, pigments, stabilizers, blowing agents, antioxidants, perfume oils and / or preservatives.
  • organic silicon compounds of the following table are combined with polyitaconic acid or PVP / VA / ltaconic acid copolymer (INCI)
  • the polyitaconic acid is either a homopolymer or a copolymer comprising a monomer unit which is derived from itaconic acid.
  • the active ingredient combination of at least one organic silicon compound and the polycarboxylic acid can already be contained in the agent for treating a keratinous material.
  • the agent itself is preferably packaged with little or no water.
  • the at least one organic silicon compound is used for 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 use of the agent for treating a keratinous material based on all the ingredients of the agent for treating a keratinous material Exception of the at least one organic silicon compound added.
  • the organosilicon compound, in particular (3-aminopropyl) triethoxysilane, and the polycarboxylic acid are alternatively used in a cosmetic product only shortly before use, ie 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, in particular the (3-aminopropyl) triethoxysilane is added to an aqueous solution which is applied to the hair and in the second step an aqueous solution or a cosmetic agent which contains the polycarboxylic acid is applied to the hair applied.
  • 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

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
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  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
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  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne une composition de principes actifs pour la modification de la forme et de la surface 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) au moins un acide polycarboxylique, ledit produit cosmétique étant particulièrement approprié pour offrir une protection structurelle contre la chaleur.
EP19797669.9A 2018-10-31 2019-10-31 Composition de principes actifs pour la modification de la surface des cheveux et la modification de la forme de la chevelure Pending EP3873417A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102018127225.1A DE102018127225A1 (de) 2018-10-31 2018-10-31 Wirkstoffzusammensetzung zur Modifikation der Haaroberfläche und Formveränderung des Haarkollektivs
PCT/EP2019/079768 WO2020089354A1 (fr) 2018-10-31 2019-10-31 Composition de principes actifs pour la modification de la surface des cheveux et la modification de la forme de la chevelure

Publications (1)

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EP3873417A1 true EP3873417A1 (fr) 2021-09-08

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Country Link
US (1) US20210346269A1 (fr)
EP (1) EP3873417A1 (fr)
JP (1) JP2022506249A (fr)
CN (1) CN112930170A (fr)
DE (1) DE102018127225A1 (fr)
WO (1) WO2020089354A1 (fr)

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6352699B1 (en) * 1997-04-04 2002-03-05 L'oreal Cosmetic or dermatological composition forming, on a keratin substrate, a film in cross-linked hybrid material
US6706674B2 (en) * 2001-01-17 2004-03-16 The Andrew Jergens Company Nonaqueous hair styling composition and method of use
FR2891143B1 (fr) * 2005-09-23 2007-11-16 Oreal Composition cosmetique comprenant un compose organique du silicium, et procede de mise en forme des cheveux
FR2911276B1 (fr) * 2007-01-12 2009-03-06 Oreal Composition cosmetique comprenant un polyurethane cationique et un homo ou copolymere de vinylpyrrolidone et application au coiffage
EP2168633B1 (fr) * 2008-09-30 2016-03-30 L'Oréal Composition cosmétique comprenant un composé organique du silicium comportant au moins une fonction basique, un polymère filmogène hydrophobe, un pigment et un solvant volatil
DE102009027679A1 (de) * 2009-07-14 2010-05-06 Henkel Ag & Co. Kgaa Permanente Pflege keratinischer Fasern
WO2012055805A1 (fr) * 2010-10-26 2012-05-03 L'oreal Composition cosmétique comprenant un alcoxysilane à chaîne grasse et agent cosmétique siliceux
FR2966352B1 (fr) * 2010-10-26 2016-03-25 Oreal Composition cosmetique comprenant un alcoxysilane a chaine grasse et un polymere cationique
FR3007973B1 (fr) * 2013-07-05 2015-08-28 Oreal Composition capillaire non-colorante comprenant un polymere associatif anionique ou non-ionique et un compose organique du silicium particulier
DE102014205806A1 (de) * 2014-03-28 2015-10-01 Evonik Degussa Gmbh Silan enthaltend jeweils mindestens zwei Alkoxygruppen sowie eine Guanidino- oder Harnstoffgruppe
GB201503393D0 (en) * 2015-02-27 2015-04-15 Revolymer U K Ltd Polymers and uses thereof
EP3389604B1 (fr) * 2015-12-14 2020-04-08 L'Oréal Composition comprenant une combinaison d'alcoxysilanes particuliers et un corps gras
ES2866275T3 (es) * 2015-12-14 2021-10-19 Oreal Procedimiento para tratar fibras queratínicas usando una composición acuosa que comprende una combinación de alcoxisilanos particulares

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JP2022506249A (ja) 2022-01-17
WO2020089354A1 (fr) 2020-05-07
US20210346269A1 (en) 2021-11-11
DE102018127225A1 (de) 2020-04-30
CN112930170A (zh) 2021-06-08

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