EP3934766A1 - Procédé pour la fabrication de produits de traitement capillaire comprenant des (alcoxy en c1-c6)silanes organiques - Google Patents

Procédé pour la fabrication de produits de traitement capillaire comprenant des (alcoxy en c1-c6)silanes organiques

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Publication number
EP3934766A1
EP3934766A1 EP20700257.7A EP20700257A EP3934766A1 EP 3934766 A1 EP3934766 A1 EP 3934766A1 EP 20700257 A EP20700257 A EP 20700257A EP 3934766 A1 EP3934766 A1 EP 3934766A1
Authority
EP
European Patent Office
Prior art keywords
stands
water
alkoxy
reaction
silanes
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP20700257.7A
Other languages
German (de)
English (en)
Inventor
Torsten LECHNER
Christoph Lohr
Andreas Walter
Claus-Peter Thiessies
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 EP3934766A1 publication Critical patent/EP3934766A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585—Organosilicon compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/893—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by an alkoxy or aryloxy group, e.g. behenoxy dimethicone or stearoxy dimethicone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits
    • A61K2800/882—Mixing prior to application
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/95—Involves in-situ formation or cross-linking of polymers

Definitions

  • the present application is in the field of cosmetics and relates to a method for the production of hair treatment compositions.
  • one or more organic Ci-C6-alkoxy-silanes are reacted with water at certain temperatures, and the Ci-C6-alcohols released in this reaction are removed from the reaction mixture at certain temperatures.
  • the method according to the invention optionally comprises the addition of one or more cosmetic ingredients and the filling of the preparation (s) into a packaging unit.
  • a second subject of the present invention is a multicomponent packaging unit (kit-of-parts) for coloring keratinic material, which, separately packaged in two packaging units, comprises the cosmetic preparations (A) and (B), the preparation (A ) is a preparation of the first subject matter of the invention and preparation (B) contains at least one coloring compound.
  • kit-of-parts for coloring keratinic material
  • Oxidation dyes are usually used for permanent, intense dyeings with good fastness properties and good gray coverage. Such colorants usually contain oxidation dye precursors, so-called developer components and coupler components, which, under the influence of oxidizing agents such as hydrogen peroxide, form the actual dyes with one another. Oxidation dyes are characterized by very long-lasting coloring results.
  • color pigments are generally understood to mean insoluble, coloring substances. These are present undissolved in the form of small particles in the coloring formulation and are only deposited on the outside of the hair fibers and / or the skin surface. Therefore they can usually be removed without residue by a few washes with detergents containing surfactants. Various products of this type are available on the market under the name of hair mascara.
  • oxidative coloring agents have so far been his only option.
  • an unpleasant smell of ammonia or amine cannot be completely avoided with oxidative hair coloring.
  • the hair damage still associated with the use of oxidative coloring agents also has an adverse effect on the user's hair.
  • EP 2168633 B1 deals with the problem of producing long-lasting hair colorations using pigments.
  • the document teaches that when a combination of pigment, organic silicon compound, hydrophobic polymer and a solvent is used, hair colors can be produced which are particularly resistant to shampooing.
  • the organic silicon compounds used in EP 2168633 B1 are reactive compounds from the alkoxy-silane class. These alkoxy-silanes hydrolyze in the presence of water at high speed and - depending on the particular amounts of alkoxy-silane and water used - form hydrolysis products and / or condensation products. The influence of the amount of water used in this reaction on the properties of the hydrolysis or condensation product is described, for example, in WO 2013068979 A2.
  • a film or also a coating forms on the keratin material, which completely envelops the keratin material and in this way strongly influences the properties of the keratin material.
  • Possible areas of application are, for example, permanent styling or the permanent change in shape of keratin fibers.
  • the keratin fibers are mechanically brought into the desired shape and then fixed in this shape by forming the above-described coating.
  • Another very particularly suitable application is the coloring of keratin material;
  • the coating or the film is produced in the presence of a coloring compound, for example a pigment. The film colored by the pigment remains on the keratin material or the keratin fibers and results in surprisingly wash-resistant colorations.
  • the great advantage of the alkoxy-silane-based coloring principle is that the high reactivity of this class of compounds enables very fast coating. This means that extremely good dyeing results can be achieved after a very short application period of just a few minutes become.
  • the high reactivity of the alkoxy silanes also has some disadvantages. Even minor changes in production and application conditions, such as changes in humidity and / or temperature, can lead to strong fluctuations in product performance. Above all, the work leading to this invention has shown that the alkoxy silanes are extremely sensitive to the conditions that prevail during the production of the keratin treatment agents. If these manufacturing conditions deviate only slightly from their optimal range of values, this can lead to a partial or even complete loss of product performance. In particular, the dyeing performance of an alkoxy-silane-based dye produced under non-optimal conditions can drop dramatically.
  • the alkoxy-silanes used in this process should be hydrolyzed and condensed in a targeted manner in such a way that compositions with the optimum application properties could be obtained.
  • the agents produced in this way should have improved dyeing performance, i. E. When they are used in a dyeing process, dyeings with higher color intensity and improved fastness properties, in particular with improved wash fastness and improved rub fastness, should be achieved.
  • a first object of the present invention is a method for producing an agent for treating keratinic material, in particular human hair, comprising the following steps:
  • hair treatment agents which have been produced by this method according to the invention, when used in a dyeing process, lead to very intense and uniform dyeings with very good rubbing fastness and washing fastness.
  • Agents for treating keratinous material have been produced by this method according to the invention, when used in a dyeing process, lead to very intense and uniform dyeings with very good rubbing fastness and washing fastness.
  • Keratinic material is understood to mean hair, skin, and nails (such as fingernails and / or toenails, for example). Furthermore, wool, furs and feathers also fall under the definition of keratinic material.
  • Keratinic material is preferably understood to mean human hair, human skin and human nails, in particular fingernails and toenails. Keratinic material is very particularly preferably understood to mean human hair.
  • Agents for treating keratinous material are understood to mean, for example, means for coloring the keratin material, means for reshaping or shaping keratinic material, in particular keratinic fibers, or also means for conditioning or maintaining the keratinic material.
  • the agents produced by the process according to the invention are particularly suitable for coloring keratinic material, in particular for coloring keratinic fibers, which are particularly preferably human hair.
  • coloring is used in the context of this invention for a coloring of the keratin material, especially the hair, caused by the use of coloring compounds, such as thermochromic and photochromic dyes, pigments, mica, substantive dyes and / or oxidation dyes.
  • coloring compounds such as thermochromic and photochromic dyes, pigments, mica, substantive dyes and / or oxidation dyes.
  • the aforementioned coloring compounds are deposited in a particularly homogeneous and smooth film on the surface of the keratin material or diffuse into the keratin fiber.
  • the film is formed in situ by oligomerization or polymerization of the organic silicon compound (s), and by the interaction of the coloring compound and the organic silicon compound and optionally other components, such as a film-forming, hydrophilic polymer.
  • Step (1) of the process according to the invention involves the reaction or conversion of one or more organic Ci-C6-alkoxy-silanes with water. This reaction takes place within a certain temperature range from 20 to 70 ° C.
  • the one or more organic Ci-C6-alkoxy-silanes are organic, non-polymeric silicon compounds, which are preferably selected from the group of silanes with one, two or three silicon atoms.
  • Organic silicon compounds which are alternatively referred to as organosilicon compounds, are compounds that have either a direct silicon-carbon bond (Si C) or in which the carbon is linked to the silicon atom via an oxygen, nitrogen or sulfur atom.
  • the organic silicon compounds according to the invention are preferably compounds which contain one to three silicon atoms.
  • the organic silicon compounds particularly preferably contain one or two silicon atoms.
  • silane stands for a group of chemical compounds based on a silicon backbone and hydrogen.
  • the hydrogen atoms have been completely or partially replaced by organic groups such as, for example, (substituted) alkyl groups and / or alkoxy groups.
  • Ci-C6-alkoxy-silanes according to the invention It is characteristic of the Ci-C6-alkoxy-silanes according to the invention that at least one C1-C6-alkoxy group is bonded directly to a silicon atom.
  • the Ci-C6-alkoxy-silanes according to the invention thus comprise at least one structural unit R'R "R” 'Si-0- (Ci-C6-alkyl) where the radicals R', R "and R” 'represent the three other bond valences of the Silicon atom.
  • the Ci-C6-alkoxy group or groups bonded to the silicon atom are very reactive and are hydrolyzed at high speed in the presence of water, the reaction rate also depending, among other things, on the number of hydrolyzable groups per molecule.
  • the organic silicon compound preferably contains a structural unit R’R “R“ ‘Si-0-CH2-CH3.
  • the radicals R ‘, R“ and R “‘ again represent the three remaining free valences of the silicon atom.
  • a method according to the invention is characterized in that in step (1) one or more organic Ci-C6-alkoxy-silanes are reacted with water, which are selected from silanes with one, two or three silicon atoms, wherein the organic silicon compound also includes one or more basic chemical functions.
  • This basic group can be, for example, an amino group, an alkylamino group or a dialkylamino group, which is preferably connected to a silicon atom via a linker.
  • the basic group is preferably an amino group, a Ci-C6-alkylamino group or a di (Ci-C6) alkylamino group.
  • Ci-C6-alkoxy-silanes of the formula (I) and / or (II) were used in the process according to the invention.
  • a method according to the invention is characterized in that in step (1) one or more organic Ci-C6-alkoxy-silanes of the formula (I) and / or (II) are reacted with water,
  • Ri, R2 independently represent a hydrogen atom or a Ci-C6-alkyl group
  • L stands for a linear or branched, divalent Ci-C2o-alkylene group
  • R3, R4 independently represent a Ci-C6-alkyl group
  • a stands for an integer from 1 to 3
  • R5, R5 ‘, R5”, 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, divalent Ci-C2o-alkylene group
  • R7 and Re independently of one another for a hydrogen atom, a Ci-C6-alkyl group, a hydroxy-Ci-C6-alkyl group, a C2-C6-alkenyl group, an amino-Ci-C6-alkyl group or a grouping of the formula (III) stand,
  • Ci-C6-alkyl group examples are the groups methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl and t-butyl, n-pentyl and n-hexyl.
  • Propyl, ethyl and methyl are preferred alkyl radicals.
  • Examples of a C 2 -C 6 alkenyl group are vinyl, allyl, but-2-enyl, but-3-enyl and isobutenyl, preferred C 2 -C 6 alkenyl radicals are vinyl and allyl.
  • a hydroxy-Ci-C6-alkyl group are a hydroxymethyl, a 2-hydroxyethyl, a 2-hydroxypropyl, a 3-hydroxypropyl, a 4-hydroxybutyl group, a 5-hydroxypentyl and a 6-hydroxyhexyl group ; a 2-hydroxyethyl group is particularly preferred.
  • Examples of an amino-Ci-C6-alkyl group are the aminomethyl group, the 2-aminoethyl group and the 3-aminopropyl group. The 2-aminoethyl group is particularly preferred.
  • Examples of a linear divalent Ci-C 2 o -alkylene group are, for example, the methylene group (-CH 2 -), the ethylene group (-CH 2 -CH 2 -), the propylene group (- CH2-CH2-CH2-) and the Butylene group (-CH2-CH2-CH2-CH2-).
  • the propylene group (-CH2-CH2-CH2-) is particularly preferred.
  • divalent alkylene groups can also be branched. Examples of branched, divalent C3-C 2 o -alkylene groups are (-CH 2 - CH (CH 3 ) -) and (-CH 2 -CH (CH3) -CH 2 -).
  • the radicals Ri and R 2 independently of one another represent a hydrogen atom or a C 1 -C 6 -alkyl group.
  • the radicals Ri and R 2 are very particularly preferably both a hydrogen atom.
  • the linker -L- which stands for a linear or branched, divalent Ci-C 2 o-alkylene group.
  • the divalent C 1 -C 2 o-alkylene group can alternatively also be referred to as a divalent or divalent C 1 -C 2 o -alkylene group, which means that each group -L- can form two bonds.
  • -L- is preferably a linear, divalent Ci-C 2 o-alkylene group. More preferably -L- stands for a linear divalent Ci-C6-alkylene group. Particularly preferably -L- stands for one Methylene group (-CH2-), an ethylene group (-CH2-CH2-), a propylene group (-CH2-CH2-) or a butylene group (-CH2-CH2-CH2-). L very particularly preferably represents a propylene group (-CH2-CH2-CH2-).
  • the radicals R3 and R4 independently of one another represent a Ci-C6-alkyl group, particularly preferably R3 and R4 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 is 3, then b is 0. If a is 2, then b is 1. If a is 1, then b is 2.
  • Hair treatment agents with particularly good properties could be produced if in step (1) at least one organic Ci-C6-alkoxy-silane of the formula (I) was reacted with water, in which the radicals R3, R4 independently of one another for a methyl group or for a Ethyl group.
  • a method according to the invention is characterized in that in step (1) one or more organic Ci-C6-alkoxy-silanes of the formula (I) are reacted with water,
  • R 3 independently of one another represent a methyl group or an ethyl group
  • a method according to the invention is characterized in that in step (1) one or more organic Ci-C6-alkoxy-silanes of the formula (I) and / or (II) are reacted with water, Ri R2N-L-Si (OR3) a (R4) b (l),
  • R2 both stand for a hydrogen atom
  • - L stands for a linear, divalent Ci-C6-alkylene group, preferably for a propylene group (- CH2-CH2-CH2-) or for an ethylene group (-CH2-CH2-),
  • R3 stands for an ethyl group or a methyl group
  • R4 stands for a methyl group or for an ethyl group
  • a method according to the invention is characterized in that in step (1) one or more organic Ci-C6-alkoxy-silanes is selected from the group consisting of
  • (3-Aminopropyl) trimethoxysilane can be purchased from Sigma-Aldrich, for example. (3-Aminopropyl) triethoxysilane is also commercially available from Sigma-Aldrich.
  • one or more organic Ci-C6-alkoxy-silanes of the formula (II) can also be reacted with water in step (1),
  • organosilicon compounds of the formula (II) according to the invention each have the silicon-containing groups (R50) c (R6) dSi and -Si (R6 ') d' (OR5 ') c at their two ends
  • each of the radicals e, f, g and h can independently represent the number 0 or 1, with the proviso that at least one of the radicals e, f, g and h is different from 0.
  • an organic silicon compound of the formula (II) according to the invention contains at least one group selected from - (A) - and - [NR 7 - (A ') j- and - [0- (A ”) j- and - [NR 8 - (A '”)] -
  • the radicals R5, R5', R5 "independently of one another represent a Ci-C6-alkyl group.
  • the radicals R6, R6 'and R6 ′′ stand independently of one another for a Ci-C6-alkyl group.
  • c stands for an integer from 1 to 3, and d stands for the integer 3 - c. If c is 3, then d is 0. If c is 2, d is 1. If c is 1, then d is 2. Similarly, 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' equals 0. If c 'stands for the number 2, then d' equals 1. If c 'stands for the number 1, then d' equals 2.
  • a method according to the invention is characterized in that in step (1) one or more organic Ci-C6-alkoxy-silanes of the formula (II) are reacted with water,
  • R5 and R5 ‘independently represent a methyl group or an ethyl group
  • the radicals e, f, g and h can independently represent the number 0 or 1, at least one radical from e, f, g and h being different from zero.
  • the abbreviations e, f, g and h therefore define which of the groupings - (A) e - and - [NR7- (A ')] f - and - [0- (A ”)] g - and - [ NR8- (A ”')] h - are located in the central part of the organic silicon compound of the formula (II).
  • the organic silicon compounds according to the invention correspond to the formula (Mb) (R50) c (R6) dSi- (AHNR7- (A ')] - Si (R6') d '(OR5') c '(Mb).
  • the radicals A, A ‘, A”, A “‘ and A ““ stand independently of one another for a linear or branched, divalent Ci-C2o-alkylene group.
  • the radicals A, A ‘, A ′′, A ′′ and A ′′ ′′ are preferably, independently of one another, a linear, divalent Ci-C20-alkylene group.
  • the radicals A, A ‘, A ′′, A ′′ A and A ′′ ′′ are more preferably, independently of one another, a linear divalent Ci-C6-alkylene group.
  • the divalent Ci-C2o-alkylene group can alternatively be referred to as a divalent or divalent Ci-C2o-alkylene group, which means that each grouping A, A ‘, A", A "‘ and A "" can form two bonds.
  • the radicals A, A ', A “, A”' and A “” are particularly preferably, independently of one another, a methylene group (-CH2-), an ethylene group (-CH2-CH2-), a propylene group (-CH2-CH2-CH2 -) or a butylene group (-CH2-CH2-CH2-).
  • the radicals A, A ‘, A ′′, A ′′ and A ′′ ′′ are very particularly preferably a propylene group (-CH2-CH2-CH2-).
  • the organic silicon compound of the invention of the formula (II) contains a structural grouping - [NR7- (A ')] -.
  • the organic silicon compound of the invention of the formula (II) contains a structural grouping - [NR8- (A "’)] -.
  • radicals R7 and Rs independently of one another represent a hydrogen atom, a Ci-Ce-alkyl group, a hydroxy-Ci-C6-alkyl group, a C2-C6-alkenyl group, an amino-Ci-C6-alkyl group or a grouping of the Formula (III)
  • the radicals R7 and R8, independently of one another, very particularly preferably represent a hydrogen atom, a methyl group, a 2-hydroxyethyl group, a 2-alkenyl group, a 2-aminoethyl group or a grouping of the formula (III).
  • the organic silicon compound according to the invention contains the grouping [NR7- (A ') j, but not the grouping - [NR8- (A ”')] now the radical R7 for a grouping of the formula (III) contains the organic silicon compound with 3 reactive silane groups.
  • a method according to the invention is characterized in that in step (1) one or more organic Ci-C6-alkoxy-silanes of the formula (II) are reacted with water
  • R7 represents a hydrogen atom, a methyl group, a 2-hydroxyethyl group, a 2-alkenyl group, a 2-aminoethyl group or a grouping of the formula (III).
  • a method according to the invention is characterized in that in step (1) one or more organic Ci-C6-alkoxy-silanes of the formula (II) are reacted with water, wherein
  • - A and A ‘independently represent a methylene group (-CH2-), an ethylene group (-CH2-CH2-) or a propylene group (-CH2-CH2-CH2),
  • R7 represents a hydrogen atom, a methyl group, a 2-hydroxyethyl group, a 2-alkenyl group, a 2-aminoethyl group or a grouping of the formula (III).
  • Bis (trimethoxysilylpropyl) amine with the CAS number 82985-35-1 can be purchased from Sigma-Aldrich, for example.
  • Bis [3- (triethoxysilyl) propyl] amine with the CAS number 13497-18-2 can be purchased from Sigma-Aldrich, for example.
  • N-methyl-3- (trimethoxysilyl) -N- [3- (trimethoxysilyl) propyl] -1-propanamine is alternatively also referred to as bis (3-trimethoxysilylpropyl) -N-methylamine and can be purchased commercially from Sigma-Aldrich or Fluorochem .
  • a method according to the invention is characterized in that in step (1) one or more organic Ci-C6-alkoxy-silanes of the formula (II) which are selected from the group of
  • the compounds of the formula (IV) are organic silicon compounds which are selected from silanes having one, two or three silicon atoms, the organic silicon compound comprising one or more hydrolyzable groups per molecule.
  • organic silicon compound or compounds of the formula (IV) can also be referred to as silanes of the alkyl-Ci-C6-alkoxy-silane type, R 9 Si (ORio) k (Rn) m (IV),
  • Rg stands for a Ci-Ci2-alkyl group
  • a method according to the invention is characterized in that in step (1) one or more organic Ci-C6-alkoxy-silanes of the formula (IV) are reacted with water,
  • Rg stands for a Ci-Ci2-alkyl group
  • the radical Rg stands for a C1-C12-alkyl group.
  • This Ci-Ci2-alkyl group is saturated and can be linear or branched.
  • R9 is preferably a linear Ci-Cs-alkyl group.
  • Rg preferably stands for 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 stands for a methyl group, an ethyl group or an n-octyl group.
  • the radical R10 stands for a Ci-C6-alkyl group.
  • R10 particularly preferably represents a methyl group or an ethyl group.
  • the radical Rn stands for a C1-C6-alkyl group.
  • R1 1 is particularly preferably a methyl group or an ethyl group.
  • k stands for an integer from 1 to 3, and m stands for the integer 3 - k. If k is 3, then m is 0. If k is 2, then m is 1. If k is the number 1, then m is 2. Dyeings with the best wash fastness properties could be obtained if an agent (a) was used in the process which contains at least one organic silicon compound of the formula (IV) in which the radical k stands for the number 3. In this case, the remainder m stands for the number 0.
  • a method according to the invention is characterized in that in step (1) one or more organic Ci-C6-alkoxy-silanes of the formula (IV) which are selected from the group of
  • the process according to the invention can be carried out in a suitable reaction vessel or reactor. Depending on the desired batch size, various models for this are known from the prior art and are commercially available.
  • the reaction of the organic Ci-C6-alkoxy-silanes with water in a reaction vessel or a reactor preferably in a double-walled reactor, a reactor with an external heat exchanger, a tubular reactor, a reactor with a thin-film evaporator, a Reactor with falling film evaporator and / or a reactor with an attached condenser.
  • a method according to the invention is characterized by
  • a reaction vessel that is very well suited for smaller batches is, for example, a glass flask with a capacity of 1 liter, 3 liters or 5 liters, usually used for chemical reactions, for example a 3 liter three-neck flask with ground joints.
  • a reactor is a delimited space (receptacle, container) that has been specially designed and manufactured to allow certain reactions to take place and control under defined conditions.
  • Typical reactors can, for example, have a capacity of 10 liters, 20 liters or 50 liters. Larger reactors for the production area can also have capacities of 100 liters, 500 liters or 1000 liters.
  • Double-wall reactors have two reactor shells or reactor walls, with a temperature control liquid being able to circulate in the area located between the two walls. This enables the temperature to be set particularly well to the required values.
  • reactors in particular double-walled reactors with an enlarged heat exchange surface, has also proven to be particularly suitable, the heat exchange here either taking place through internal fixtures or also through the use of an external heat exchanger.
  • Corresponding reactors are, for example, laboratory reactors from IKA.
  • the models "LR-2.ST” or the model “magic plant” can be mentioned.
  • reactors that can be used are reactors with thin-film evaporators, since in this way very good heat dissipation and thus particularly precise temperature control can be generated.
  • thin-film evaporators are also referred to as thin-film evaporators.
  • Thin film evaporators are commercially available from Asahi Glassplant Inc., for example.
  • the evaporation In reactors with falling film evaporators, the evaporation generally takes place in a tube, i.e. the liquid to be evaporated (i.e. in this case the C1-C6 alcohols to be removed in step (2)) flow as a continuous liquid film.
  • the liquid to be evaporated i.e. in this case the C1-C6 alcohols to be removed in step (2)
  • Reactors with falling film evaporators are also commercially available from various suppliers.
  • the reaction of the organic Ci-C6-alkoxy-silanes with water that takes place in step (1) can take place in various ways.
  • One possibility is to place the desired amount of water in the reaction vessel or reactor and then to add that or the Ci-C6-alkoxy-silanes.
  • the hydrolysis reaction can also take place several times per Ci-C6-alkoxy-silane used:
  • the water can be added continuously, in partial amounts or directly as a total amount.
  • the reaction mixture is preferably cooled and / or the amount and rate of addition of the water are adjusted. Depending on the amount of silanes used, the addition and reaction can take place over a period of 2 minutes to 72 hours.
  • step (1) In order to produce agents which produce a particularly good coating on the keratin material, it has been found to be explicitly and particularly preferred to use water in a substoichiometric amount in step (1).
  • the amount of water used is below the amount that would theoretically be required to remove all hydrolyzable Ci-C6 alkoxy groups present on the Si atoms, i.e. the alkoxysilane groups, to hydrolyze. Partial hydrolysis of the organic Ci-C6-alkoxy-silanes is therefore very particularly preferred.
  • the stoichiometric ratio of water to the organic Ci-C6-alkoxy-silanes can be defined via the proportion of molar equivalents of water (S-W), these are calculated using the following formula: mol (water)
  • mol (silanes) total molar amount of Ci-C6-alkoxy-silanes used in the reaction
  • n (alkoxy) number of Ci-C6-alkoxy groups per Ci-C6-alkoxy-silane
  • the molar equivalent of water indicates the molar ratio of the molar amount of water used to the total number of moles of hydrolyzable C1-C6 alkoxy groups that are on the Ci-C6 alkoxysilanes used.
  • a method according to the invention is characterized by (1) Reaction of the organic Ci-C6-alkoxy-silanes with 0.10 to 0.80 molar equivalents of water (SW), preferably from 0.15 to 0.70, more preferably from 0.20 to 0.60 and very particularly preferably from 0.25 to 0.50 molar equivalents of water,
  • SW molar equivalents of water
  • mol (silanes) total molar amount of Ci-C6-alkoxy-silanes used in the reaction
  • n (alkoxy) number of Ci-C6-alkoxy groups per Ci-C6-alkoxy-silane
  • step (1) For the production of particularly high-performance keratin treatment agents, in step (1) it has been found that maintaining specific temperature ranges is essential.
  • step (1) it was found that a minimum temperature of 20 ° C. is necessary in step (1) in order to allow the hydrolysis to proceed at a sufficiently high rate and to ensure that the reaction is carried out efficiently.
  • step (2) it is imperative to avoid heating the reaction mixture to temperatures above 70 ° C. If the production takes place at too high temperatures, an undesired or excessive polymerization or condensation reaction takes place, which leads to the fact that when the agent is subsequently used on the keratin material, no more film adhering to the keratin can form .
  • an agent produced at too high a temperature in a dyeing process it was no longer possible to achieve sufficiently high color intensities.
  • step (1) of the process the reaction of the organic Ci-C6-alkoxy-silane (s) with water in step (1) of the process must be carried out at a temperature of 20 to 70.degree.
  • the temperature range given here relates to the temperature to which the mixture of Ci-C6-alkoxy-silanes and water must be set. This temperature can be measured, for example, by a calibrated thermometer protruding into this mixture.
  • the reaction of one or more organic Ci-C6-alkoxy-silanes with water is preferably carried out at a temperature from 20 to 65 ° C, preferably from 20 to 60 ° C, more preferably from 20 to 55 ° C, even more preferably from 20 to 50 ° C and very particularly preferably from 20 to 45 ° C.
  • a method according to the invention is characterized by
  • the temperature ranges according to the invention and preferred can be set by controlling the temperature of the reaction vessel or reactor.
  • the reaction vessel or the reactor can be surrounded on the outside with a temperature control bath, which can be, for example, a water bath or a silicone oil bath.
  • a temperature-controlled liquid can also be passed through the space which is formed by the two walls and which surrounds the reaction space.
  • step (1) there is no active heating of the reaction mixture and that any increase in temperature above the ambient temperature is brought about only by the exothermic nature of the hydrolysis in step (1). If the exothermic reaction process heats the reaction mixture too much in step (1), it must be cooled again.
  • the reaction of the organic Ci-C6-alkoxy-silanes with water takes place preferably at normal pressure, ie at a pressure of 1013 mbar (1013 hPa).
  • Step (2) of the process according to the invention is characterized by the partial or complete removal of the Ci-C6 alcohols released by the reaction in step (1) from the reaction mixture at a temperature of 20 to 70.degree.
  • step (2) of the process is preferably carried out after step (1).
  • the Ci-C6 alcohols can be removed either directly after the hydrolysis in step (1).
  • a cosmetic ingredient corresponding to step (3) of the method according to the invention can first be added and the Ci-C6 alcohols (step (2)) can then be removed.
  • step (2) can also be carried out simultaneously with the hydrolysis in step (1).
  • the removal of the Ci-C6 alcohols is started before the addition of the water, at the start of the addition or after 5-20% by weight of the planned total amount of the water has been added, i.e. the distillation - if necessary with a reduction in pressure - started.
  • the reaction equilibrium is shifted in favor of a condensation reaction, in which the Si-OH groups on the (partially) hydrolyzed Ci-C6-alkoxysilanes are split off with other Si-OH groups or with other Ci -C6-alkoxy-silane groups can react.
  • Ci-C6-alkoxysilanes which undergo a condensation with not yet reacted, partially or completely hydrolyzed Ci-C6-alkoxysilanes, can take part in the condensation reaction.
  • condensation to form a dimer is shown, but the condensation to form oligomers with several silane atoms is also possible and also preferred.
  • the extent of the condensation reaction is determined by the amount of water added in step (1).
  • the amount of water is preferably measured so that the condensation is a partial condensation, with “partial condensation” or “partial condensation” in this context meaning that not all condensable groups of the silanes present react with one another, so that the organic silicon compound formed per molecule still has on average at least one hydrolyzable / condensable group.
  • the temperature at which the Ci-C6 alcohols are removed from the reaction mixture in step (2) also represent a significant influencing factor with regard to the performance of the subsequent hair treatment product.
  • the process according to the invention encompasses both the complete and partial removal of the C 1 -C 6 alcohols released. Since the complete removal of all Ci-C6 alcohols can only be achieved with difficulty (small residues of Ci-C6 alcohols will always remain in the reaction mixture), partial removal of the Ci-C6 alcohols is preferred.
  • the specified temperature range again relates to the temperature to which the reaction mixture must be adjusted while the Ci-C6-alkoxy-silanes are removed from the reaction mixture.
  • This temperature can also be measured, for example, by a calibrated thermometer protruding into this mixture.
  • a method according to the invention is characterized by
  • a method for producing an agent for treating keratinous material, in particular human hair comprising the following steps:
  • a method for producing an agent for treating keratinous material, in particular human hair comprising the following steps:
  • a method for producing an agent for treating keratinous material, in particular human hair comprising the following steps:
  • a method for producing an agent for treating keratinous material, in particular human hair comprising the following steps:
  • a method for producing an agent for treating keratinous material, in particular human hair comprising the following steps:
  • the preferred temperature ranges according to the invention can be set, for example, by heating or cooling the reaction vessel or reactor, for example by using the reaction vessel in a heating mantle, or by surrounding the reaction vessel with a temperature-controlled bath from the outside which can be, for example, a water bath or a silicone oil bath.
  • a temperature-controlled liquid can also be passed through the space which is formed by the two walls and which surrounds the reaction space.
  • the Ci-C6 alcohols are preferably removed under reduced pressure (compared to normal pressure). It has proven particularly advantageous in this connection to distill off the C1-C6 alcohols from the reaction mixture using a distillation attachment. During this distillation, a pressure of 10 to 900 mbar, more preferably 10 to 800 mbar, is preferred, set even more preferably from 10 to 600 mbar and very particularly preferably from 10 to 300 mbar.
  • Vacuum distillation is a common chemical process for which the common, commercially available vacuum pumps and distillation apparatus can be used.
  • the distillation apparatus can be provided as an attachment on the reaction vessel or reactor.
  • a method according to the invention is characterized by
  • the volatile alcohols and, if necessary, also the water that has been distilled off can be condensed and collected as liquid distillate in a receiver.
  • the distillation can optionally take place with cooling of the evaporated alcohols / water by means of a cooler.
  • the reduced pressure can be generated using conventional methods known in the art, typically with a vacuum pump.
  • C 1 -C 6 alkoxysilanes which carry methoxysilane or ethoxysilane groups are very particularly preferably used in the process according to the invention, in particular di- and trimethoxy and -ethoxysilanes, particularly preferably trimethoxy or triethoxysilanes.
  • step (2) of the method according to the invention which is referred to as “evaporative cooling”.
  • a solvent is added to the reaction mixture prior to the removal of the Ci-C6 alcohols in step (2) which has a boiling point of 20 to 90 ° C, preferably 30 to 85 ° C and very particularly at normal pressure (1013 hPa) preferably from 40 to 80 ° C.
  • This added solvent can also be referred to as “low boiler”.
  • a method according to the invention is characterized in that, before the Ci-C6 alcohols are removed in step (2), a solvent is added which has a boiling point of 20 to 90 ° C at normal pressure (1013 hPa). preferably from 30 to 85 ° C and very particularly preferably from 40 to 80 ° C.
  • Suitable solvents are, for example:
  • Particularly suitable solvents are methanol, ethanol and isopropanol.
  • the vacuum distillation of step (2) takes place under conditions which result in a product which contains less than 5% by weight, preferably less than 2% by weight, even more preferably less than 1% by weight, alcohols (from the Hydrolysis reaction).
  • the water content of the product after vacuum distillation is less than 5.0% by weight, even more preferably less than 1.0% by weight and very particularly preferably less than 0.5% by weight.
  • the method according to the invention comprises the addition of one or more cosmetic ingredients.
  • the cosmetic ingredients that can optionally be used in step (3) can be all suitable constituents in order to impart further positive properties to the agent.
  • a solvent, a thickening or film-forming polymer, a surface-active compound from the group of nonionic, cationic, anionic or zwitterionic / amphoteric surfactants the coloring compounds from the group of pigments, substantive dyes, the Oxidation dye precursors, the fatty components from the group of Cs-Cso fatty alcohols, the hydrocarbon compounds, fatty acid esters, the acids and bases belonging to the group of pH regulators, those of perfumes, preservatives, plant extracts and protein hydrolysates.
  • a method according to the invention is characterized by (3) Addition of one or more cosmetic ingredients from the group of solvents, polymers, surface-active compounds, coloring compounds, fat components, pH regulators, perfumes, preservatives, plant extracts and protein hydrolysates.
  • a cosmetic ingredient in step (3) which further improves the stability, in particular the storage stability, of the keratin treatment agent.
  • the addition (3) of one or more cosmetic ingredients from the group of hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane and / or decamethylcyclopentasiloxane has proven to be particularly advantageous with regard to increasing the stability of the composition.
  • a method according to the invention is characterized by
  • Hexamethyldisiloxane has the CAS number 107-46-0 and can be obtained commercially from Sigma-Aldrich, for example.
  • Octamethyltrisiloxane has the CAS number 107-51-7 and is also commercially available from Sigma-Aldrich.
  • Decamethyltetrasiloxane has the CAS number 141-62-8 and is also commercially available from Sigma-Aldrich.
  • Hexamethylcyclotrisiloxane has the CAS no. 541 -05-9.
  • Octamethylcyclotetrasiloxane has the CAS no. 556-67-2.
  • Decamethylcyclopentasiloxane has the CAS no. 541-02-6.
  • step (4) of the method according to the invention the preparation obtained after steps (1) and (2) and, if appropriate, after optional step (3) is filled into a packaging unit.
  • the packaging unit can either be an end package from which the user takes the agent for treating the keratin materials.
  • Suitable end-of-line packaging is for example a bottle, a tube, a jar, a can, a sachet, an aerosol pressure container, a non-aerosol pressure container.
  • This end-of-line packaging can contain the keratin treatment agent in quantities that are sufficient for one, if necessary also for several, applications. Preference is given to filling in an amount that is sufficient for a single use.
  • the preparation in step (4) can, however, also be filled into an intermediate packaging, which can be, for example, a canister or a hobbock. Filling into intermediate packaging is particularly suitable when the reaction vessel or the reactor in which the process according to the invention was carried out and the filling plant in which the final packaging is filled are spatially separated.
  • a method according to the invention is characterized by
  • the aforementioned packaging units can be conventional containers used as standard in cosmetics. pH values of the preparations in the process
  • the pH values which the reaction mixture has in the course of steps (1) to (4) of the process according to the invention can also have an influence on the condensation reaction. It was found here that alkaline pH values in particular stop the condensation at the oligomer stage. The more acidic the reaction mixture, the more condensation seems to take place and the higher the molecular weight of the siloxanes formed during the condensation. For this reason, it is preferred that the reaction mixture in step (1), (2), (3) and / or (4) has a pH of 7.0 to 12.0, preferably from 7.5 to 11, 5, more preferably from 8.5 to 11.0 and very particularly preferably from 9.0 to 11.0.
  • the water content of the composition is preferably a maximum of 10.0% by weight and is particularly preferably set even lower.
  • the measurement of the pH value with the usual methods known from the prior art can prove difficult.
  • the pH values according to the invention are those values which were obtained after mixing or diluting the preparation in a weight ratio of 1: 1 with distilled water.
  • the corresponding pH value is measured accordingly after, for example, 50 g of the composition according to the invention have been mixed with 50 g of distilled water.
  • a process according to the invention is characterized in that the reaction mixture in step (1), (2), (3) and / or (4) has a pH after dilution with distilled water in a weight ratio of 1: 1 -Value from 7.0 to 12.0, preferably from 7.5 to 11.5, more preferably from 8.5 to 11.0 and very particularly preferably from 9.0 to 11.0.
  • a method according to the invention is characterized in that the reaction mixture in steps (1), (2), (3) and (4) has a pH after dilution with distilled water in a weight ratio of 1: 1 -Value from 7.0 to 12.0, preferably from 7.5 to 11.5, more preferably from 8.5 to 11.0 and very particularly preferably from 9.0 to 11.0.
  • the pH values in the context of the present invention are pH values that were measured at a temperature of 22 ° C.
  • Ammonia, alkanolamines and / or basic amino acids can be used as alkalizing agents.
  • Alkanolamines can be selected from primary amines with a C2-C6-alkyl parent structure which carries at least one hydroxyl group.
  • Preferred alkanolamines are selected from the group which is formed from 2-aminoethan-1 -ol (monoethanolamine), 3-aminopropan-1 -ol, 4-aminobutan-1 -ol, 5-aminopentan-1 -ol, 1-aminopropane -2-ol, 1-aminobutan-2-ol, 1-aminopentan-2-ol, 1-aminopentan-3-ol, 1-aminopentan-4-ol, 3-amino-2-methylpropan-1-ol, 1 -Amino-2-methyl-propan-2-ol, 3-aminopropan-1, 2-diol, 2-amino-2-methylpropan-1, 3-diol.
  • amino acid in the context of the invention is an organic compound which in its structure contains at least one amino group which can be protonated and at least one —COOH or one —SOsH group.
  • Preferred amino acids are aminocarboxylic acids, in particular ⁇ - (alpha) -amino carboxylic acids and w-aminocarboxylic acids, ⁇ -aminocarboxylic acids being particularly preferred.
  • basic amino acids are to be understood as meaning those amino acids which have an isoelectric point p1 of greater than 7.0.
  • Basic ⁇ -aminocarboxylic acids contain at least one asymmetric carbon atom.
  • both possible enantiomers can be used equally as specific compounds or mixtures thereof, in particular as racemates.
  • the basic amino acids are preferably selected from the group that is formed from arginine, lysine, ornithine and histidine, particularly preferably from arginine and lysine.
  • an agent according to the invention is therefore characterized characterized in that the alkalizing agent is a basic amino acid from the group arginine, lysine, ornithine and / or histidine.
  • Inorganic alkalizing agents can also be used.
  • Inorganic alkalizing agents which can be used according to the invention are preferably selected from the group formed by sodium hydroxide, potassium hydroxide, calcium hydroxide, barium hydroxide, sodium phosphate, potassium phosphate, sodium silicate, sodium metasilicate, potassium silicate, sodium carbonate and potassium carbonate.
  • Very particularly preferred alkalizing agents are ammonia, 2-aminoethan-1-ol (monoethanolamine), 3-aminopropan-1-ol, 4-aminobutan-1 -ol, 5-aminopentan-1 -ol, 1-aminopropan-2-ol, 1-aminobutan-2-ol, 1-aminopentan-2-ol, 1-aminopentan-3-ol, 1-aminopentan-4-ol, 3-amino-2-methylpropan-1-ol, 1-amino-2- methylpropan-2-ol, 3-aminopropan-1, 2-diol, 2-amino-2-methylpropan-1, 3-diol, arginine, lysine, ornithine, histidine, sodium hydroxide, potassium hydroxide, calcium hydroxide, barium hydroxide, sodium phosphate, potassium phosphate, Sodium silicate, sodium metasilicate, potassium silicate, sodium carbonate and potassium carbonate.
  • Acidifying agents preferred according to the invention are pleasure acids, such as citric acid, acetic acid, malic acid or tartaric acid, and also dilute mineral acids.
  • step (3) being an optional step.
  • step (1) begins with step (1), followed by step (2), followed by step (3), followed by step (4), ie after the partial or complete removal of the Ci-C6 alcohols in step (2) the One or more cosmetic ingredients added to the reaction mixture for example a solvent, a pigment, a thickening polymer or the like. could be.
  • the preparation is then filled into a packaging unit.
  • the keratin treatment agents produced by means of this process can be used for various purposes, for example as an agent for coloring keratin material, as an agent for the care of keratin material or as an agent for changing the shape of keratin material.
  • a method according to the invention is characterized in that an agent for coloring keratin material, for caring for keratin material or for changing the shape of keratin material is produced.
  • compositions produced explicitly show very particularly good suitability when used in a dyeing process.
  • a method according to the invention is characterized in that an agent for coloring keratinic material is produced.
  • the coloring compound being selected can be from the group of pigments, substantive dyes and / or oxidation dye precursors.
  • an agent for coloring keratin material can be obtained which, in addition to the prehydrolyzed / condensed C1-C6-alkoxysilanes, also contains the coloring compound (s).
  • the hair colorant available to the user as part of a multi-component packaging unit.
  • a second subject of the present invention is therefore a multi-component packaging unit (kit-of-parts) for coloring keratinous material, in particular human hair, which is packaged separately from one another
  • the cosmetic preparation (A) was produced in the first packaging unit by the method as already disclosed in detail in the description of the first subject matter of the invention, and
  • the cosmetic preparation (B) contains at least one coloring compound from the group of the pigments, the substantive dyes and / or the oxidation dye precursors.
  • one or more coloring compounds can be used.
  • the coloring compound (s) can either be added to the reaction mixture as cosmetic ingredients in step (3) of the method, or they can be made available to the user as an ingredient of a separately made up preparation (b).
  • the coloring compound or compounds can preferably be selected from the pigments, the substantive dyes, the oxidation dyes, the photochromic dyes and the thermochromic dyes, particularly preferably from pigments and / or substantive dyes.
  • Pigments in the context of the present invention are understood to mean coloring compounds which at 25 ° C. in water have a solubility of less than 0.5 g / L, preferably less than 0.1 g / L, even more preferably less than 0, 05 g / L.
  • the water solubility can be achieved, for example, by means of the method described below: 0.5 g of the pigment is weighed out in a beaker. A stir fry is added. Then one liter of distilled water is added. This mixture is stirred on a magnetic stirrer for heated to 25 ° C for one hour. If undissolved constituents of the pigment are still visible in the mixture after this period, the solubility of the pigment is below 0.5 g / L.
  • the mixture is filtered. If a proportion of undissolved pigments remains on the filter paper, the solubility of the pigment is below 0.5 g / L.
  • Suitable color pigments can be of inorganic and / or organic origin.
  • an agent according to the invention is characterized in that it (b) contains at least one coloring compound from the group of inorganic and / or organic pigments.
  • Preferred color pigments are selected from synthetic or natural inorganic pigments.
  • Inorganic color pigments of natural origin can be made from chalk, ocher, umber, green earth, burnt Terra di Siena or graphite, for example.
  • black pigments such as B. iron oxide black, colored pigments such.
  • B. ultramarine or iron oxide red and fluorescent or phosphorescent pigments can be used.
  • Colored metal oxides, hydroxides and oxide hydrates, mixed-phase pigments, sulfur-containing silicates, silicates, metal sulfides, complex metal cyanides, metal sulfates, metal chromates and / or molybdates are particularly suitable.
  • Particularly preferred color pigments are black iron oxide (CI 77499), yellow iron oxide (CI 77492), red and brown iron oxide (CI 77491), manganese violet (CI 77742), ultramarines (sodium aluminum sulfosilicates, CI 77007, Pigment Blue 29), chromium oxide hydrate (CI77289 ), Iron blue (Ferric Ferrocyanide, CI77510) and / or carmine (Cochineal).
  • Coloring compounds from the group of pigments which are likewise particularly preferred according to the invention are colored pearlescent pigments. These are usually based on mica and / or mica and can be coated with one or more metal oxides. Mica is one of the layered silicates. The most important representatives of these silicates are muscovite, phlogopite, paragonite, biotite, lepidolite and margarite. To produce the pearlescent pigments in conjunction with metal oxides, the mica, predominantly muscovite or phlogopite, is coated with a metal oxide.
  • synthetic mica coated with one or more metal oxide (s) can also be used as a pearlescent pigment.
  • Particularly preferred pearlescent pigments are based on natural or synthetic mica (mica) and are with a or more of the aforementioned metal oxides coated.
  • the color of the respective pigments can be varied by varying the layer thickness of the metal oxide (s).
  • an agent according to the invention is characterized in that it contains (b) at least one coloring compound from the group of pigments, which is selected from the group of colored metal oxides, metal hydroxides, metal oxide hydrates, silicates, metal sulfides, complex metal cyanides, metal sulfates , Bronze pigments and / or from coloring compounds based on mica or mica, which are coated with at least one metal oxide and / or a metal oxychloride.
  • an agent according to the invention is characterized in that it contains (b) at least one coloring compound which is selected from pigments based on mica or mica which are mixed with one or more metal oxides from the group consisting of titanium dioxide (CI 77891), black iron oxide (CI 77499), yellow iron oxide (CI 77492), red and / or brown iron oxide (CI 77491, CI 77499), manganese violet (CI 77742), ultramarines (sodium aluminum sulfosilicates, CI 77007, pigment blue 29), chromium oxide hydrate ( CI 77289), chromium oxide (CI 77288) and / or iron blue (Ferric Ferrocyanide, CI 77510) are coated.
  • at least one coloring compound which is selected from pigments based on mica or mica which are mixed with one or more metal oxides from the group consisting of titanium dioxide (CI 77891), black iron oxide (CI 77499), yellow iron oxide (CI 77492), red and / or brown iron oxide (
  • color pigments are commercially available under the trade names Rona®, Colorona®, Xirona®, Dichrona® and Timiron® from Merck, Ariabel® and Unipure® from Sensient, Prestige® from Eckart Cosmetic Colors and Sunshine® available from Sunstar.
  • Colorona® Particularly preferred color pigments with the trade name Colorona® are, for example:
  • color pigments with the trade name Unipure® are, for example:
  • the agent according to the invention can also (b) contain one or more coloring compounds from the group of organic pigments
  • the organic pigments according to the invention are correspondingly insoluble, organic dyes or color lakes, for example from the group of nitroso, nitro, azo, xanthene, anthraquinone, isoindolinone, isoindoline, quinacridone, perinone, perylene -, Diketopyrrolopyorrole, indigo, thioindido, dioxazine, and / or triarylmethane compounds can be selected.
  • Particularly suitable organic pigments are, for example, carmine, quinacridone, phthalocyanine, sorghum, blue pigments with the color index numbers CI 42090, CI 69800, CI 69825, CI 73000, CI 74100, CI 74160, yellow pigments with the color index numbers CI 1 1680, CI 1 1710, CI 15985, CI 19140, CI 20040, CI 21 100, CI 21 108, CI 47000, CI 47005, green pigments with the Color Index numbers CI 61565, CI 61570, CI 74260, orange pigments with the Color Index numbers CI 1 1725, CI 15510, CI 45370, CI 71 105, red pigments with the color index numbers
  • an agent according to the invention is characterized in that it (b) contains at least one coloring compound from the group of organic pigments, which is selected from the group of carmine, quinacridone, phthalocyanine, sorghum, blue pigments with the color index Numbers CI 42090, CI 69800, CI 69825, CI 73000, CI 74100, CI 74160, yellow pigments with the Color Index numbers CI 1 1680, CI 1 1710, CI 15985, CI 19140, CI 20040, CI 21 100, CI 21 108 , CI 47000, CI 47005, green pigments with the color index numbers CI 61565, CI 61570, CI 74260, orange pigments with the color index numbers CI 1 1725, CI 15510, CI 45370, CI 71 105, red pigments with the color index Numbers
  • the group of organic pigments which is selected from the group of carmine, quinacridone, phthalocyanine,
  • the organic pigment can also be a colored lacquer.
  • the term “colored varnish” is understood to mean particles which comprise a layer of absorbed dyes, the unit of particles and dyestuff being included in the above. Conditions is insoluble.
  • the particles can be, for example, inorganic substrates, which can be aluminum, silica, calcium borosilicate, calcium aluminum borosilicate or also aluminum.
  • the alizarin color varnish for example, can be used as the color varnish.
  • the use of the aforementioned pigments in the agents according to the invention is particularly preferred because of their excellent light and temperature stability. It is also preferred if the pigments used have a certain particle size. This particle size leads, on the one hand, to a uniform distribution of the pigments in the polymer film formed and, on the other hand, avoids a rough hair or skin feel after the cosmetic agent has been applied. It is therefore advantageous according to the invention if the at least one pigment has an average particle size D50 of 1.0 to 50 ⁇ m, preferably 5.0 to 45 ⁇ m, more preferably 10 to 40 ⁇ m, in particular 14 to 30 ⁇ m.
  • the mean particle size D50 can be determined, for example, using dynamic light scattering (DLS).
  • the pigment or pigments (b) can be used in an amount of from 0.001 to 20% by weight, in particular from 0.05 to 5% by weight, based in each case on the total weight of the agent according to the invention.
  • the agents according to the invention can also contain one or more substantive dyes as coloring compounds (b).
  • Direct dyes are dyes that are absorbed directly onto the hair and do not require an oxidative process to develop the color.
  • Substantive dyes are usually nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones, triarylmethane dyes or indophenols.
  • the substantive dyes for the purposes of the present invention have a solubility in water (760 mmHg) at 25 ° C. of more than 0.5 g / L and are therefore not to be regarded as pigments.
  • the substantive dyes preferably have a solubility in water (760 mmHg) at 25 ° C. of more than 1.0 g / l.
  • the substantive dyes particularly preferably have a solubility in water (760 mmHg) at 25 ° C. of more than 1.5 g / l.
  • Substantive dyes can be divided into anionic, cationic and nonionic substantive dyes.
  • an agent according to the invention is characterized in that it contains at least one anionic, cationic and / or nonionic substantive dye as coloring compound (b).
  • an agent according to the invention is characterized in that it contains (b) at least one anionic, cationic and / or nonionic substantive dye.
  • Suitable cationic substantive dyes are, for example, Basic Blue 7, Basic Blue 26, Basic Violet 2 and Basic Violet 14, Basic Yellow 57, Basic Red 76, Basic Blue 16, Basic Blue 347 (Cationic Blue 347 / Dystar), HC Blue No. 16, Basic Blue 99, Basic Brown 16, Basic Brown 17, Basic Yellow 57, Basic Yellow 87, Basic Orange 31, Basic Red 51 Basic Red 76
  • Nonionic nitro and quinone dyes and neutral azo dyes can be used as nonionic substantive dyes.
  • Suitable nonionic substantive dyes are those under the international names or trade names HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, HC Yellow 12, HC Orange 1, Disperse Orange 3, HC Red 1, HC Red 3, HC Red 10, HC Red 1 1, HC Red 13, HC Red BN, HC Blue 2, HC Blue 1 1, HC Blue 12, Disperse Blue 3, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Disperse Black 9 known compounds , as well as 1,4-diamino-2-nitrobenzene, 2-amino-4-nitrophenol, 1,4-bis- (2-hydroxyethyl) -amino-2-nitrobenzene, 3-nitro-4- (2-hydroxyethyl) - aminophenol, 2- (2-
  • Acid dyes are taken to mean substantive dyes which have at least one carboxylic acid group (-COOH) and / or one sulfonic acid group (-SO3H).
  • -COOH carboxylic acid group
  • -SO3H sulfonic acid group
  • the protonated forms (-COOH, -SO3H) of the carboxylic acid or sulfonic acid groups are in equilibrium with their deprotonated forms (-COO-, -S03 _ ). The proportion of protonated forms increases with decreasing pH.
  • Acid dyes according to the invention can also be used in the form of their sodium salts and / or their potassium salts.
  • the acid dyes for the purposes of the present invention have a solubility in water (760 mmHg) at 25 ° C. of more than 0.5 g / L and are therefore not to be regarded as pigments.
  • the acid dyes preferably have a solubility in water (760 mmHg) at 25 ° C. of more than 1.0 g / l.
  • the alkaline earth salts such as calcium salts and magnesium salts
  • aluminum salts of acid dyes often have a poorer solubility than the corresponding alkali salts. If the solubility of these salts is below 0.5 g / L (25 ° C, 760 mmHg), they do not fall under the definition of a substantive dye.
  • An essential feature of the acid dyes is their ability to form anionic charges, the carboxylic acid or sulfonic acid groups responsible for this usually being linked to different chromophoric systems.
  • Suitable chromophoric systems can be found for example in the structures of nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinone dyes, triarylmethane dyes, xanthene dyes, rhodamine dyes, oxazine dyes and / or indophenol dyes.
  • Acid Yellow 1 (D&C Yellow 7, Citronin A, Ext. D&C Yellow No. 7, Japan Yellow 403, CI 10316, COLIPA n ° B001), Acid Yellow 3 (COLIPA n °: C 54, D&C Yellow N ° 10, Quinoline Yellow, E104, Food Yellow 13), Acid Yellow 9 (CI 13015), Acid Yellow 17 (CI 18965), Acid Yellow 23 (COLIPA n ° C 29, Covacap Jaune W 1 100 (LCW), Sicovit Tartrazine 85 E 102 (BASF), Tartrazine, Food Yellow 4, Japan Yellow 4, FD&C Yellow No.
  • Acid Yellow 1 (D&C Yellow 7, Citronin A, Ext. D&C Yellow No. 7, Japan Yellow 403, CI 10316, COLIPA n ° B001), Acid Yellow 3 (COLIPA n °: C 54, D&C Yellow N ° 10, Quinoline Yellow, E104, Food Yellow 13), Acid Yellow 9 (CI 13015), Acid Yellow 17 (CI 18965), Acid Yellow 23 (COLIPA
  • Acid Yellow 36 (CI 13065), Acid Yellow 121 ( CI 18690), Acid Orange 6 (CI 14270), Acid Orange 7 (2- Naphthol orange, Orange II, CI 15510, D&C Orange 4, COLIPA n ° C015), Acid Orange 10 (Cl 16230; Orange G sodium salt), Acid Orange 1 1 (CI 45370), Acid Orange 15 (CI 50120), Acid Orange 20 (CI 14600), Acid Orange 24 (BROWN 1; CI 20170; KATSU201; nosodiumsalt; Brown No.201; RESORCIN BROWN; ACID ORANGE 24 ; Japan Brown 201; D&C Brown No.1), Acid Re d 14 (C.I.14720), acid red 18 (E124, red 18; C1 16255), Acid Red 27 (E 123, C1 16185, C-Red 46, Echtrot D, FD&C Red Nr.2, Food Red 9, Naphtholrot S), Acid Red 33 (Red 33, Fuchsia Red, D&C Red 33,
  • Acid Green 50 (Brillantklare indispensable BS, Cl 44090, Acid Brilliant Green BS, E 142), Acid Black 1 (Black n ° 401, Naphthalene Black 10B, Amido Black 10B, CI 20 470, COLIPA n ° B15), Acid Black 52 (CI 1571 1), Food Yellow 8 (CI 14270), Food Blue 5, D&C Yellow 8, D&C Green 5, D&C Orange 10, D&C Orange 1 1, D&C Red 21, D&C Red 27, D&C Red 33, D&C Violet 2 and / or D&C Brown 1.
  • the water solubility of the anionic substantive dyes can be determined, for example, in the following way. 0.1 g of the anionic substantive dye are in a Given beaker. A stir bar is added. Then 100 ml of water are added. This mixture is heated to 25 ° C. on a magnetic stirrer while stirring. It is stirred for 60 minutes. The aqueous mixture is then assessed visually. If there are still undissolved residues, the amount of water is increased - for example in steps of 10 ml. Water is added until the amount of dye used has completely dissolved. If the dye-water mixture cannot be assessed visually due to the high intensity of the dye, the mixture is filtered.
  • the solubility test is repeated with a larger amount of water. If 0.1 g of the anionic substantive dye dissolves in 100 ml of water at 25 ° C., the solubility of the dye is 1.0 g / l.
  • Acid Yellow 1 is called 8-hydroxy-5,7-dinitro-2-naphthalenesulfonic acid disodium salt and has a solubility in water of at least 40 g / L (25 ° C).
  • Acid Yellow 3 is a mixture of the sodium salts of mono- and sisulfonic acids of 2- (2-quinolyl) -1H-indene-1,3 (2H) -dione and has a water solubility of 20 g / L (25 ° C).
  • Acid Yellow 9 is the disodium salt of 8-hydroxy-5,7-dinitro-2-naphthalenesulfonic acid, its water solubility is above 40 g / L (25 ° C).
  • Acid Yellow 23 is the trisodium salt of 4,5-dihydro-5-oxo-1 - (4-sulfophenyl) -4 - ((4-sulfophenyl) azo) -1H-pyrazole-3-carboxylic acid and is good at 25 ° C soluble in water.
  • Acid Orange 7 is the sodium salt of 4 - [(2-Hydroxy-1-naphthyl) azo] benzene sulfonate. Its water solubility is more than 7 g / L (25 ° C).
  • Acid Red 18 is the trinity salt of 7-hydroxy-8 - [(E) - (4-sulfonato-1-naphthyl) -diazenyl)] - 1,3-naphthalenedisulfonate and has a very high solubility in water of more than 20 wt. %.
  • Acid Red 33 is the diantrium salt of 5-amino-4-hydroxy-3- (phenylazo) -naphthalene-2,7-disulphonate, its water solubility is 2.5 g / L (25 ° C).
  • Acid Red 92 is the disodium salt of 3,4,5,6-tetrachloro-2- (1,4,5,8-tetrabromo-6-hydroxy-3-oxoxanthen-9-yl) benzoic acid, its water solubility is specified with greater than 10 g / L (25 ° C).
  • Acid Blue 9 is the disodium salt of 2 - ( ⁇ 4- [N-ethyl (3-sulfonatobenzyl] amino] phenyl ⁇ ⁇ 4 - [(N-ethyl (3-sulfonatobenzyl) imino] -2,5-cyclohexadiene-1 - ylidene ⁇ methyl) benzene sulfonate and has a water solubility of more than 20% by weight (25 ° C).
  • thermochromic dyes can also be used.
  • Thermochromism includes the property of a material to change its color reversibly or irreversibly depending on the temperature. This can be done both by changing the intensity and / or the wavelength maximum.
  • Photochromism includes the property of a material, depending on the irradiation with light, especially UV light, reversibly or irreversibly changing its color. This can be done both by changing the intensity and / or the wavelength maximum.
  • a reactor with a heatable / coolable outer shell and a capacity of 10 liters was filled with 4.67 kg of methyltrimethoxysilane. 1.33 kg (3-aminopropyl) triethoxysilane were then added with stirring. This mixture was stirred at 30 ° C. Then 670 ml of water (distilled) were added dropwise with vigorous stirring, the temperature of the reaction mixture being kept at 30 ° C. with external cooling. After the addition of water had ended, stirring was continued for a further 10 minutes. A vacuum of 280 mbar was then applied, the reaction mixture was heated to a temperature of 44 ° C., and the ethanol and methanol released during the reaction were distilled off. The alcohols distilled off were collected in a cooled receiver.
  • a reactor with a heatable / coolable outer shell and a capacity of 10 liters was filled with 4.67 kg of methyltrimethoxysilane. 1.33 kg (3-aminopropyl) triethoxysilane were then added with stirring. This mixture was stirred at 30 ° C. Then 670 ml of water (distilled) were added quickly with vigorous stirring. The addition took place without external temperature control, and the reaction mixture heated to 75 ° C. After the addition of water had ended, stirring was continued until the reaction mixture had cooled to 44.degree. A vacuum of 280 mbar was then applied and the reaction mixture was kept at a temperature of 44.degree. The ethanol and methanol liberated in the reaction were distilled off.
  • the alcohols distilled off were collected in a cooled receiver. It was distilled until no more alcohols condensed in the receiver under the chosen reaction conditions. The reaction mixture was then allowed to cool to room temperature. 3.33 kg of hexamethyldisiloxane were then added dropwise to the mixture obtained in this way with stirring. The mixture was subsequently stirred for 10 minutes and the silane blend 2 was poured into a hobbock and the hobbock was tightly closed.
  • a reactor with a heatable / coolable outer shell and a capacity of 10 liters was filled with 4.67 kg of methyltrimethoxysilane. 1.33 kg (3-aminopropyl) triethoxysilane were then added with stirring. This mixture was stirred at 30 ° C. Then 670 ml of water (distilled) were added dropwise with vigorous stirring, the temperature of the reaction mixture being kept at 30 ° C. with external cooling. To When the addition of water had ended, the mixture was stirred for a further 10 minutes. A vacuum of 280 mbar was then applied, the reaction mixture was heated to a temperature of 75 ° C. and the ethanol and methanol released during the reaction were distilled off.
  • the alcohols distilled off were collected in a cooled receiver. It was distilled until no more alcohols condensed in the receiver under the chosen reaction conditions. The reaction mixture was then allowed to cool to room temperature. 3.33 kg of hexamethyldisiloxane were then added dropwise to the mixture obtained in this way with stirring. The mixture was subsequently stirred for 10 minutes and the silane blend 3 was poured into a hobbock and the hobbock was tightly closed.
  • a reactor with a heatable / coolable outer shell and a capacity of 10 liters was filled with 4.67 kg of methyltrimethoxysilane. 1.33 kg (3-aminopropyl) triethoxysilane were then added with stirring. This mixture was stirred at 30 ° C. Then 670 ml of water (distilled) were added quickly with vigorous stirring. The addition took place without external temperature control, and the reaction mixture heated to 75 ° C. After the addition of water had ended, stirring was continued for a further 10 minutes. A vacuum of 280 mbar was then applied, the reaction mixture was heated to a temperature of 75 ° C. and the ethanol and methanol released during the reaction were distilled off. The alcohols distilled off were collected in a cooled receiver.
  • the ready-to-use colorant was prepared by spilling 10 g of preparation (A) and 100 g of preparation (B) (shaking for 3 minutes). This mixture was then left to stand for 5 minutes.

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Abstract

La présente invention concerne un procédé pour la production d'un produit pour le traitement de matière kératinique, en particulier de cheveux humains, comprenant les étapes suivantes : (1) réaction d'un ou plusieurs (alcoxy en C1-C6)silanes avec de l'eau à une température de 20 à 70 °C, (2) élimination complète ou partielle des alcools en C1-C6 libérés durant la réaction de l'étape (1) du mélange réactionnel à une température de 20 à 70 °C, (3) le cas échéant, ajout d'un ou plusieurs ingrédients cosmétiques, et (4) remplissage de la préparation dans une unité d'emballage.
EP20700257.7A 2019-03-06 2020-01-08 Procédé pour la fabrication de produits de traitement capillaire comprenant des (alcoxy en c1-c6)silanes organiques Withdrawn EP3934766A1 (fr)

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DE102019203074.2A DE102019203074A1 (de) 2019-03-06 2019-03-06 Verfahren zur Herstellung von Haarbehandlungsmitteln mit organischen C1-C6-Alkoxy-Silanen
PCT/EP2020/050251 WO2020177933A1 (fr) 2019-03-06 2020-01-08 Procédé pour la fabrication de produits de traitement capillaire comprenant des (alcoxy en c1-c6)silanes organiques

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AU5867899A (en) * 1999-09-27 2001-04-30 L'oreal Cosmetic compositions based on partly neutralised organic silicon compounds
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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
DE102009026746A1 (de) * 2009-06-04 2010-12-09 Sensient Imaging Technologies Gmbh Sprühgetrocknete Farbstoffkomposite, Verfahren zu ihrer Herstellung und ihre Verwendung
EP2311844A1 (fr) * 2009-10-15 2011-04-20 Interquim, S.A. Composés d'ester d'acide benzoïque polymérique en silyl, utilisations, et compositions associées
FR2982155B1 (fr) 2011-11-09 2014-07-18 Oreal Composition cosmetique comprenant au moins un alcoxysilane
FR2999918B1 (fr) * 2012-12-26 2015-06-19 Oreal Polymere de type sol-gel a empreinte moleculaire pour pieger selectivement les molecules odorantes
US9744120B2 (en) * 2015-05-28 2017-08-29 IndusCo, Ltd. Durable skin sanitizers containing water stable antimicrobial silanol quaternary ammonium compounds
WO2017102856A1 (fr) * 2015-12-14 2017-06-22 L'oreal Procédé de traitement de fibres kératiniques à l'aide d'une composition aqueuse comprenant une combinaison d'alcoxysilanes particuliers

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WO2020177933A1 (fr) 2020-09-10

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