EP4181859A1 - Suspension de pigments et agent cosmétique préparé à l'aide de la suspension de pigments - Google Patents

Suspension de pigments et agent cosmétique préparé à l'aide de la suspension de pigments

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Publication number
EP4181859A1
EP4181859A1 EP21729294.5A EP21729294A EP4181859A1 EP 4181859 A1 EP4181859 A1 EP 4181859A1 EP 21729294 A EP21729294 A EP 21729294A EP 4181859 A1 EP4181859 A1 EP 4181859A1
Authority
EP
European Patent Office
Prior art keywords
group
pigment
pigments
pigment suspension
stands
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
EP21729294.5A
Other languages
German (de)
English (en)
Inventor
Gabriele Weser
Ulrike Schumacher
Claudia Kolonko
Caroline KRIENER
Jing Hodes
Irmgard Bender
Phillip Jaiser
Marc NOWOTTNY
Juergen Schoepgens
Torsten LECHNER
Andreas Walter
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 EP4181859A1 publication Critical patent/EP4181859A1/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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/044—Suspensions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/55—Phosphorus compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/58—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
    • A61K8/86—Polyethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes

Definitions

  • the present application relates to a pigment suspension comprising a pigment, a dispersant and a carrier medium.
  • a further object is a cosmetic product which was produced using the pigment suspension and an organosilicon compound.
  • Pigments are often used in coatings, paints, printing inks, powder coatings, cosmetics or plastics for coloring. Paints, varnishes, printing inks, cosmetics and powder coatings are liquid or powdered coating materials that are applied to surfaces in order to obtain both improved or modified optical and physical properties.
  • Oxidation colorants are usually used for permanent, intensive colorations with good fastness properties and good gray coverage. Such colorants usually contain oxidation dye precursors, so-called developer components and coupler components, which form the actual dyes with one another under the influence of oxidizing agents such as hydrogen peroxide. Oxidation coloring agents are characterized by very long-lasting coloring results.
  • color pigments are generally understood to mean insoluble, color-imparting substances. These are present in undissolved form in the form of small particles in the coloring formulation and are only deposited from the outside on the hair fibers and/or the surface of the skin. Therefore, they can usually be removed without leaving any residue with a few washes with detergents containing surfactants.
  • Various products of this type are available on the market under the name of hair mascara.
  • the pigments are made available to the user in a form that is stable on storage and can be metered. This can be done in particular in the form of a storage-stable pigment suspension.
  • Ground pigment powder and water are usually used to produce inorganic pigment suspensions. It may be necessary to add small amounts of organic or inorganic dispersing agents.
  • Some pigments in particular pigments based on iron oxide, have a very strong tendency to form so-called agglomerates. This means that the individual primary particles adhere strongly to each other and therefore have to be broken up with high shearing forces in order to distribute the pigments evenly in the carrier medium.
  • the dispersing agent forms a kind of protective covering around each individual dispersed pigment particle. A distinction is made between steric and electrostatic stabilization by the dispersing agent.
  • the dispersant it is not only desirable that it is able to protect a wide variety of pigments, which differ, for example, in composition, particle size, particle shape and / or surface aftertreatment, from agglomeration, but that it also allows the use of the pigment suspension in cosmetic funds allowed.
  • the object of the present invention is to provide pigment suspensions which are also suitable for use in cosmetic agents, which can be produced easily and inexpensively and are stable on storage.
  • the pigments in the pigment suspension should be stable against agglomeration.
  • pigment suspensions containing at least one phosphoric acid ester as a dispersing agent meet these requirements.
  • a first subject of the application is a pigment suspension comprising a) at least one color-providing compound from the group of pigments, b) at least one phosphoric acid ester and c) water.
  • the pigment suspensions contain at least one coloring compound from the group of pigments as the first ingredient essential to the invention.
  • pigments are understood to mean coloring compounds which have a solubility in water at 25° C. of less than 0.5 g/l, preferably less than 0.1 g/l, even more preferably less than 0. Possess 05 g/L.
  • the water solubility can be determined, for example, using the method described below: 0.5 g of the pigment is weighed out in a glass beaker. A stir bar is added. Then one liter of distilled water is added. This mixture is heated to 25°C with stirring on a magnetic stirrer for one hour. If undissolved components of the pigment are still visible in the mixture after this period, the solubility of the pigment is below 0.5 g/L.
  • 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 pigments can be of inorganic and/or organic origin.
  • Preferred color pigments are selected from synthetic or natural inorganic pigments.
  • Inorganic color pigments of natural origin can be made from chalk, ochre, umber, green earth, burnt terra di sienna or graphite, for example.
  • black pigments such 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, metal hydroxides and metal oxide hydrates, mixed phase pigments, sulfur-containing silicates, silicates, metal sulfides, complex metal cyanides, metal sulfates, metal chromates and/or metal molybdates are particularly suitable.
  • 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), hydrated chromium oxide (CI77289 ), Iron Blue (Ferric Ferrocyanide, CI77510) and/or Carmine (Cochineal).
  • Coloring compounds from the group of pigments which are also particularly preferred according to the invention are colored pearlescent pigments. These are usually based on mica and/or mica and can be coated with one or more metal oxides. Mica belongs to the layered silicates. The most important representatives of these silicates are muscovite, phlogopite, paragonite, biotite, lepidolite and margarite. To produce the pearlescent pigments in combination with metal oxides, the mica, mainly muscovite or phlogopite, is coated with a metal oxide.
  • synthetic mica optionally coated with one or more metal oxides can also be used as pearlescent pigment.
  • Particularly preferred pearlescent pigments are based on natural or synthetic mica (mica) and are coated with one or more of the aforementioned metal oxides. The color of the respective pigments can be varied by varying the layer thickness of the metal oxide(s).
  • mica-based pigments are synthetically produced mica flakes coated with metal oxide, in particular based on synthetic fluorophlogopite (INCI: Synthetic Fluorphlogopite).
  • the synthetic fluorophlogopite platelets are coated, for example, with tin oxide, iron oxide(s) and/or titanium dioxide.
  • the metal oxide layers can also contain pigments such as iron(II/I) hexacyanidoferrate(II/I 11) or carmine red
  • a pigment suspension is characterized in that it contains at least one coloring compound from the group of inorganic pigments, which is selected from the group consisting of black iron oxide (CI 77499), yellow iron oxide (CI 77492), red iron oxide (CI 77491) and mixtures thereof.
  • Yellow iron oxide (or iron oxide yellow) is the designation for FeO(OH), in the Color Index under C.l. Pigment Yellow 42 listed.
  • Red iron oxide (or iron oxide red) is the designation for Fe 2 03, listed in the Color Index under Cl Pigment Red 101. Depending on the particle size, red iron oxide pigments can be made very yellowish (small particle size) to very bluish (coarse particles).
  • Black iron oxide (or iron oxide black) is listed in the Color Index under Cl Pigment Black 11. Iron oxide black is ferromagnetic. The chemical formula is often given as Fe30 4 , but in reality it is a mixed crystal of Fe 2 03 and FeO with an inverse spinel structure. Additional black pigments are obtained by doping with chromium, copper or manganese.
  • Brown black iron oxide usually does not refer to a defined pigment, but to a mixture of yellow, red and/or black iron oxide.
  • iron oxide pigments with particle diameters in the range from 100 to 1,000 nm, more preferably 150 nm 700 nm, can be stably dispersed and show little or no agglomeration.
  • Iron oxide pigments usually have particle diameters in the range from 2000 to 4000 nm. For some applications, in particular for cosmetic purposes, it can be advantageous to use iron oxide pigments with significantly smaller particle diameters. For example, hair dyeings with iron oxide pigments that have a particle diameter in the range from 100 to 1000 nm, more preferably 150 nm to 700 nm, exhibit better durability and better gray coverage.
  • the coloring compound comprises a pigment from the group of iron oxide pigments.
  • the coloring compound comprises a pigment from the group of iron oxide pigments, the iron oxide pigments having a particle diameter in the range from 100 to 1000 nm, more preferably 150 nm to 700 nm.
  • organic pigments usually have particle diameters in the range from 2000 to 3000 nm.
  • organic Pigments with a particle diameter in the range 100 to 1000 nm, more preferably 150 nm 700 nm, are stably dispersed in aqueous pigment suspensions.
  • the coloring compound comprises a pigment from the group of organic pigments.
  • the coloring compound comprises at least one pigment from the group of organic pigments, the organic pigment having a particle diameter in the range from 100 to 1000 nm, more preferably 150 nm to 700 nm.
  • the particle diameter of the pigments in particular the iron oxide pigments and/or the organic pigments, can be determined, for example, by means of laser light scattering methods and laser light diffraction methods.
  • the organic pigments are correspondingly insoluble organic dyes or lakes, for example from the group of nitroso, nitro, azo, xanthene, anthraquinone, isoindolinone, isoindoline, quinacridone, perinone, perylene , diketopyrrolopyrrole, indigo, thioindido, dioxazine, and/or triarylmethane compounds can be selected.
  • Particularly suitable organic pigments are, for example, carmine, quinacridone, phthalocyanine, sorghum, blue pigments with the Color Index numbers CI 42090, CI 69800, CI 69825, CI 73000, CI 74100, CI 74160, yellow pigments with the Color Index numbers CI 11680 , CI 11710, CI 15985, CI 19140, CI 20040, CI 21100, CI 21108, CI 47000, CI 47005, green pigments with the Color Index numbers CI 61565, CI 61570, CI 74260, orange pigments with the Color Index numbers CI 11725 , CI 15510, CI 45370, CI 71105, red pigments with the Color Index numbers CI 12085, CI 12120, CI 12370, CI 12420, CI 12490, CI 14700, CI 15525, CI 15580, CI 15620, CI 15630, CI 15800
  • the coloring compound is at least one organic pigment selected from the group consisting of carmine, quinacridone, phthalocyanine, sorghum, blue pigments with the Color Index numbers CI 42090, CI 69800, CI 69825, CI 73000, CI 74100, CI 74160, yellow pigments with the Color Index numbers CI 11680, CI 11710, CI 15985, CI 19140, CI 20040, CI 21100, CI 21108, CI 47000, CI 47005, green pigments with the Color Index numbers CI 61565, CI 61570, CI 74260, orange pigments with the Color Index numbers CI 11725, CI 15510, CI 45370, CI 71105, red pigments with the Color Index numbers CI 12085, CI 12120, CI 12370, CI 12420, CI 12490, CI 14700, CI 15525, CI 15580
  • the pigment suspension can contain other pigments.
  • These further pigments can in particular comprise effect pigments, comprising pigments with substrate flakes made of metal and/or pigments with substrate flakes made of a metal alloy.
  • the pigment suspension preferably contains less than 0.05% by weight, based on the total pigment suspension, of effect pigments, comprising pigments with metal substrate flakes and/or pigments with metal alloy substrate flakes.
  • the pigment suspension more preferably contains no effect pigments, comprising pigments with substrate flakes made of metal and/or pigments with substrate flakes made of a metal alloy.
  • other color-imparting compounds can be contained in the pigment suspension.
  • the other color-providing compounds can include, in particular, substantive dyes.
  • the amount of pigment in the pigment suspension depends in particular on the type of pigment(s) and its intended use.
  • the amount of pigment is preferably between 0.5 and 70% by weight, more preferably between 1 and 60% by weight and very particularly preferably between 5 and 50% by weight, based in each case on the total weight of the pigment suspension.
  • inorganic pigments are commercially available, for example under the trade names Rona®, Colorona®, Xirona®, Dicrona® and Timiron® from Merck, Ariabel® and Unipure® from Sensient, Prestige® from Eckart Cosmetic Colors and Sunshine® available from Sunstar.
  • Colorona® examples of very particularly preferred pigments with the trade name Colorona® are: Colorona Copper, Merck, MICA, CI 77491 (IRON OXIDES)
  • particularly preferred pigments with the trade name Unipure® are, for example: Unipure Red LC 381 EM, Sensient CI 77491 (Iran Oxides), Silica Unipure Black LC 989 EM, Sensient, CI 77499 (Iran Oxides), Silica Unipure Yellow LC 182 EM, Sensient , CI 77492 (Iran Oxides), silica
  • the pigment suspension comprises at least one phosphoric acid ester as the second ingredient essential to the invention.
  • Phosphoric acid esters are esters of orthophosphoric acid that are formally or actually formed by the reaction of the acid and alcohol with the elimination of water. A distinction is made between monoesters, diesters and triesters. Monoesters are formed by the reaction of the alcohol with polyphosphoric acid, while mixtures of mono- and diesters are made by the reaction of the alcohol with phosphorus pentoxide.
  • the esters of orthophosphoric acid with aliphatic alcohols can be used as the phosphoric acid ester.
  • the aliphatic alcohols are, in particular, linear or branched, saturated or unsaturated alcohols having 1 to 22 carbon atoms and 0, 1, 2 or 3 double bonds.
  • Typical representatives are, for example, methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, tert-butanol, n-pentanol, caproic alcohol, caprylic alcohol, 2-ethylhexanol, capric alcohol, myristyl alcohol, lauryl alcohol, cetyl alcohol, palmitoleyl alcohol, stearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselyl alcohol, linolyl alcohol, linolenyl alcohol, behenyl alcohol or erucyl alcohol.
  • the aliphatic alcohols are preferably branched and saturated alcohols having 11 to 14 carbon atoms.
  • the aliphatic alcohols are very particularly preferably a mixture of branched and saturated alcohols having 11 to 14 carbon atoms, which has a high proportion of isotridecanol.
  • the pigment suspension is characterized in that it contains at least one phosphoric acid ester selected from the group consisting of esters of orthophosphoric acid with aliphatic alcohols.
  • the pigment suspension is characterized in that it contains at least one phosphoric acid ester, comprising an ester of orthophosphoric acid with a branched, aliphatic alcohol having 11 to 14 carbon atoms.
  • a particularly suitable phosphoric acid ester that can be used in the pigment suspension is Phosfetal 218 (CAS number: 154518-38-4, Phosphoric acid, C11-14-isoalkyl esters, C13-rich), which is available from Zschimmer & Schwarz.
  • the esters of orthophosphoric acid with alkoxylated, aliphatic alcohols or the esters of orthophosphoric acid with alkoxylated phenols can be used as the phosphoric acid ester.
  • the alkoxylated alcohols are, in particular, ethoxylated alcohols having 1 to 22 carbon atoms.
  • the pigment suspension is characterized in that it comprises at least one phosphoric acid ester, comprising an ester of orthophosphoric acid with an ethoxylated, aliphatic alcohol having 1 to 22 carbon atoms.
  • the pigment suspension is characterized in that it comprises at least one phosphoric acid ester, comprising an ester of orthophosphoric acid with an ethoxylated, aliphatic alcohol having 8 to 18 carbon atoms.
  • the average degree of ethoxylation of the aliphatic alcohols is preferably in the range from 2 to 80 and more preferably in the range from 5 to 25.
  • Crodafos SP (INCI: Ceteth-20 Phosphate), available from Croda.
  • the alkoxylated phenols are preferably ethoxylated phenols or ethoxylated alkyl phenols.
  • the phosphoric acid ester is preferably used in specific quantity ranges. So it has been found to be particularly advantageous if the pigment suspension - based on the total weight of the pigment suspension - one or more phosphoric acid esters in a total amount of 0.5 to 30 wt .-%, preferably 1 to 25 wt .-%, more preferably from 2 to 20% by weight and most preferably from 5 to 15% by weight.
  • a pigment suspension is characterized in that - based on the total weight of the pigment suspension - one or more phosphoric acid esters, comprising an ester of orthophosphoric acid with a branched aliphatic alcohol having 11 to 14 carbon atoms, in a total amount of 0.5 to 30% by weight, preferably 1 to 25% by weight, more preferably from 2 to 20% by weight and very particularly preferably from 5 to 15% by weight.
  • one or more phosphoric acid esters comprising an ester of orthophosphoric acid with a branched aliphatic alcohol having 11 to 14 carbon atoms, in a total amount of 0.5 to 30% by weight, preferably 1 to 25% by weight, more preferably from 2 to 20% by weight and very particularly preferably from 5 to 15% by weight.
  • a pigment suspension is characterized in that it contains - based on the total weight of the pigment suspension - one or more phosphoric acid esters, comprising an ester with the INCI name Ceteth-20 phosphate, in a total amount of 0.5 to 30 wt %, preferably 1 to 25% by weight, more preferably from 2 to 20% by weight and very particularly preferably from 5 to 15% by weight.
  • the pigment suspension contains water as the third essential component.
  • the water content is preferably above 20% by weight, more preferably above 40% by weight and particularly preferably above 60% by weight.
  • the pigment suspension can contain a further vehicle, for example a C 1 -C 4 alcohol, in particular ethanol or isopropanol.
  • the pigment suspension also contains other organic solvents as carriers, such as methoxybutanol, benzyl alcohol, ethyl diglycol or 1,2-propylene glycol.
  • the pH of the pigment suspension is preferably in the alkaline range.
  • the pH of the pigment suspension is preferably in the range from 9.5 to 11 and even more preferably in the range from 10 to 10.5.
  • the pigment suspension may contain at least one alkalizing agent or at least one acidifying agent.
  • the pH values for the purposes of the present invention are pH values measured at a temperature of 22.degree.
  • a second subject matter of the present invention relates to a cosmetic agent. This was produced by combining a pigment suspension according to the present invention with one or more organic C 1 -C 6 alkoxysilanes and/or their condensation products.
  • cosmetic agents can be provided that contain all the desired components that are advantageous for the cosmetic agent, the pigments being protected from decomposition and the C 1 -C 6 -alkoxysilanes from hydrolysis.
  • Such cosmetic agents can be used, for example, in processes for coloring keratinic material, in particular human hair.
  • the cosmetic agent is characterized in that it contains one or more organic C1-C6 alkoxysilanes and/or their condensation products.
  • organic C 1 -C 6 alkoxysilane or organic, non-polymeric silicon compounds are preferably selected from the group of silanes having one, two or three silicon atoms
  • Organic silicon compounds are compounds that either have a direct silicon-carbon bond (Si-C) or in which the carbon is bonded to the silicon via an oxygen, nitrogen, or sulfur atom. atom is linked.
  • the organic silicon compounds according to the invention are preferably compounds containing one to three silicon atoms.
  • the organic silicon compounds particularly preferably contain one or two silicon atoms.
  • silane stands for a group of chemical compounds based on a silicon backbone and hydrogen. In the case of organic silanes, some or all of the hydrogen atoms are replaced by organic groups such as (substituted) alkyl groups and/or alkoxy groups.
  • Ci-C6-alkoxysilanes according to the invention It is characteristic of the Ci-C6-alkoxysilanes according to the invention that at least one C1-C6 alkoxy group is directly bonded to a silicon atom.
  • the C1-C6-alkoxysilanes according to the invention thus comprise at least one structural unit R'R"R"'Si-O-(Ci-C6-alkyl), where the radicals R', R" and R"' stand for the three remaining bond valences of the silicon atom .
  • the C 1 -C 6 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 speed also depending, inter alia, 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 condensation product is understood as meaning a product that is formed by reaction of at least two organic Ci-C6-alkoxysilanes with elimination of water and/or elimination of a Ci-C6-alkanol.
  • the condensation products can be, for example, dimers, but also trimers or oligomers, the condensation products being in equilibrium with the monomers.
  • a cosmetic agent is characterized in that the cosmetic agent contains one or more organic Ci-C6-alkoxysilanes selected from silanes having one, two or three silicon atoms, the organic silicon compound also containing one or more includes basic chemical functions.
  • This basic group can be, for example, an amino group, an alkylamino group or a dialkylamino group, which is preferably linked via a linker connected to a silicon atom.
  • the basic group is preferably an amino group, a Ci-C6-alkylamino group or a di(Ci-C6)-alkylamino group.
  • a very particularly preferred agent is characterized in that the cosmetic agent contains one or more organic Ci-C6-alkoxysilanes which are selected from the group of silanes having one, two or three silicon atoms, and where the Ci-C6-alkoxysilanes also contain one or comprise several basic chemical functions.
  • a method according to the invention is characterized in that the cosmetic agent contains one or more organic C 1 -C6 alkoxysilanes of the formula (Sl) and/or (S-II),
  • Ri, R 2 independently represent a hydrogen atom or a Ci-C6-alkyl group
  • L is a linear or branched, divalent Ci-C 2 o-alkylene group
  • R3, R4 independently represent a Ci-C6-alkyl group, a represents an integer from 1 to 3, and b represents the integer 3 - a, and
  • R5, R5', R5", R6, R6' and R6" independently represent a Ci-C6-alkyl group
  • A, A', A", A"' and A"" independently represent a linear or branched, divalent Ci-C 2 o-alkylene group
  • R7 and Re independently represent a hydrogen atom, a Ci-C6-alkyl group, a hydroxy-Ci-C6-alkyl group, a C 2 -C6-alkenyl group, an amino-Ci-C6-alkyl group or a group of the formula (p -Ill) stand,
  • - c' is an integer from 1 to 3
  • 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 -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 bivalent Ci-C 2 o-alkylene group are, for example, the methylene group (-CH 2 -), the ethylene group (-CH 2 -CH 2 -), the propylene group (-CH 2 -CH 2 -CH 2 - ) and the butylene group (-CH 2 -CH 2 -CH 2 -CH 2 -).
  • the propylene group (-CH 2 -CH 2 -CH 2 -) is particularly preferred.
  • divalent alkylene groups can also be branched. Examples of branched, divalent C 3 -C 2 o-alkylene groups are (-CH 2 -CH(CH 3 )-) and (-CH 2 -CH(CH 3 )-CH 2 -).
  • RiR 2 NL-Si(OR 3 )a(R4)b (Sl), the radicals Ri and R 2 independently represent a hydrogen atom or a C1-C6 alkyl group.
  • the radicals Ri and R 2 are very particularly preferably both 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, divalent Ci-C 2 o-alkylene group.
  • the bivalent Ci-C 2 o- Alkylene group can alternatively also be referred to as a divalent or two -bonded Ci-C 2 O-alkylene group, meaning that each -L- moiety can form two bonds.
  • -L- preferably stands for a linear, divalent Ci-C 2 o-alkylene group. More preferably -L- is a linear bivalent Ci-C6-alkylene group. -L- is particularly preferably a methylene group (-CH2-), an ethylene group (-CH2-CH2-), a propylene group (-CH2-CH2-CH2-) or a butylene group (-CH 2 -CH 2 -CH 2 - CH 2 -). Very particularly preferably, L is a propylene group (- CH 2 -CH 2 -CH 2 -).
  • the radicals R3 and R4 independently represent a Ci-C6-alkyl group.
  • R3 and R 4 particularly preferably independently represent a methyl group or an ethyl group.
  • a represents an integer of 1 to 3
  • b represents an integer of 3 - a. If a is the number 3, then b is equal to 0. If a is the number 2, then b is equal to 1. If a is the number 1, then b is equal to 2.
  • Cosmetic agents with particularly good coloring properties in keratinic materials could be produced if the agent contains at least one organic C 1 -C 6 alkoxysilane of the formula (S1) in which the radicals R 3 , R 4 independently represent a methyl group or an ethyl group.
  • the cosmetic agent contains at least one organic C 1 -C 6 alkoxysilane of the formula (S-1) in which the radical a stands for the number 3. In this case, the remainder b stands for the number 0.
  • a cosmetic agent is characterized in that it contains one or more organic Ci-C6-alkoxysilanes of the formula (S-l), where
  • R3, R4 independently represent a methyl group or an ethyl group
  • a cosmetic agent is characterized in that it contains at least one or more organic Ci-C6-alkoxysilanes of the formula (SI),
  • R2 both represent a hydrogen atom
  • - L is a linear, divalent Ci-C6-alkylene group, preferably a propylene group (-CH2-CH2-CH2-) or an ethylene group (-CH2-CH2-),
  • R3 represents an ethyl group or a methyl group
  • R4 represents a methyl group or an ethyl group
  • Particularly suitable organic silicon compounds of the formula (I) are - (3-aminopropyl) triethoxysilane
  • a cosmetic agent is characterized in that it contains at least one organic C 1 -C 6 alkoxysilane of the formula (SI), which is selected from the group consisting of - (3-aminopropyl)triethoxysilane
  • organic silicon compounds of the formula (I) are commercially available.
  • (3-aminopropyl)trimethoxysilane is commercially available from Sigma-Aldrich.
  • (3-Aminopropyl)triethoxysilane is also commercially available from Sigma-Aldrich.
  • the cosmetic agent can also contain one or more organic Ci-C6-alkoxysilanes of the formula (S-II),
  • alkoxysilanes of the formula (S-II) carry the silicon-containing groups (R50) c (R6)dSi- and -Si(R6')d'(OR5')c at both 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 is.
  • a preferred alkoxysilane of formula (II) contains at least one moiety from the group consisting of -(A)- and -[NR7-(A')j- and -[0-(A”)j- and -[NRs - (A'”)]-
  • the radicals R5, R5', R5'' independently stand for a Ci-C6-alkyl group.
  • the radicals R6, R6' and R6'' independently stand for a Ci-C6-alkyl group.
  • c is an integer of 1 to 3
  • d is an integer of 3 - c. If c is the number 3, then d is equal to 0. If c is the number 2, then d is equal to 1. If c is the number 1, then d is equal to 2.
  • c' represents an integer from 1 to 3 and d' represents the integer 3 - c'. If c' is the number 3, then d' is 0. If c' is the number 2, then d' is 1. If c' is the number 1, then d' is 2. Dyeings with the best fastness to washing could be obtained if the radicals c and c' both stand for the number 3. In this case, d and d' both represent the number 0.
  • a cosmetic agent is characterized in that it contains one or more organic Ci-C6-alkoxysilanes of the formula (S-II),
  • 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, where at least one radical from e, f, g and h is different from zero.
  • the abbreviations e, f, g and h therefore define which of the groups -(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 formula (II).
  • the radicals A, A', A", A"' and A”" independently represent a linear or branched, divalent C 1 -C 20 -alkylene group.
  • the radicals A, A′, A′′, A′′′′ and A′′′′ are preferably, independently of one another, a linear, divalent C 1 -C 20 -alkylene group.
  • the radicals A, A′, A′′, A′′′′ and A′′′′ are more preferably, independently of one another, a linear divalent Ci-C6-alkylene group.
  • the divalent Ci-C 2 o-alkylene group may alternatively be as a divalent or a divalent C 1 -C 20 - are referred alkylene group, by which is meant that each group A, A ', A ", A"' and A "" two can form bonds.
  • the radicals A, A′, A′′, A′′′′ and A′′′′ independently stand for a methylene group (-CH2-), an ethylene group (-CH2-CH2-), a propylene group (-CH2-CH2-CH2 -) or a butylene group (-CH 2 -CH 2 -CH 2 -CH 2 -).
  • the radicals A, A′, A′′, A′′′′ and A′′′′ are very particularly preferably a propylene group (-CH2-CH2-CH2-).
  • the organic silicon compound of the formula (II) according to the invention contains a structural grouping -[NR7-(A')]-.
  • the organic silicon compound of the formula (II) according to the invention contains a structural grouping -[NR8-(A''')]-.
  • R? and Rs independently represent a hydrogen atom, a C 1 -C6 alkyl group, a hydroxy-Ci-C6-alkyl group, a C 2 -C6-alkenyl group, an amino-Ci-C6-alkyl group or a group of the formula (p -ill)
  • the radicals R7 and R8 are very particularly preferably, independently of one another, a hydrogen atom, a methyl group, a 2-hydroxyethyl group, a 2-alkenyl group, a 2-aminoethyl group or a group of the formula (S-III).
  • the organic silicon compound of the invention contains the [NR7-(A')j moiety but not the -[NR8-(A''')] moiety now the radical R7 for a group of the formula (III), the organic silicon compound comprises 3 reactive silane groups.
  • a cosmetic agent is characterized in that the cosmetic agent contains one or more organic C 1 -C 6 alkoxysilanes of the formula (S-II).
  • - A and A' independently represent a linear, bivalent Ci-C6-alkylene group
  • the cosmetic agent represents a hydrogen atom, a methyl group, a 2-hydroxyethyl group, a 2-alkenyl group, a 2-aminoethyl group or a group of formula (S-III).
  • the cosmetic agent is characterized in that it contains one or more organic Ci-C6-alkoxysilanes of the formula (S-II), where
  • - A and A' independently represent a methylene group (-CH2-), an ethylene group (-CH2-CH2-) or a propylene group (-CH2-CH2-CH2), and
  • R7 represents a hydrogen atom, a methyl group, a 2-hydroxyethyl group, a 2-alkenyl group, a 2-aminoethyl group or a group of formula (S-III).
  • Very suitable organic silicon compounds of the formula (S-II) are -3-(trimethoxysilyl)-N-[3-(trimethoxysilyl)propyl]-1-propanamine
  • organic silicon compounds of the formula (S-II) are commercially available.
  • bis(trimethoxysilylpropyl)amine with CAS number 82985-35-1 can be purchased from Sigma-Aldrich.
  • bis[3-(triethoxysilyl)propyl]amine with CAS number 13497-18-2 is commercially available from Sigma-Aldrich.
  • N-methyl-3-(trimethoxysilyl)-N-[3-(trimethoxysilyl)propyl]-1-propanamine is referred to as bis(3-trimethoxysilylpropyl)-N-methylamine and is commercially available from Sigma-Aldrich or Fluorochem .
  • a cosmetic agent is characterized in that the cosmetic agent contains one or more organic Ci-C6-alkoxysilanes of the formula (S-II), which are selected from the group consisting of
  • the cosmetic agent contains at least one organic Ci-C6-alkoxysilane of the formula (S-IV) R 9 Si(ORio)k(Rn)m (S-IV).
  • the compounds of formula (S-IV) are organic silicon compounds selected from silanes having one, two or three silicon atoms, the organic silicon compound comprising one or more hydrolyzable groups per molecule.
  • the or the organic silicon compounds of the formula (S-IV) can also be referred to as silanes of the alkyl-Ci-C6-alkoxysilanes type,
  • Rg stands for a Ci-Ci2-alkyl group
  • - k is an integer from 1 to 3
  • - m is the integer 3 - k.
  • a particularly preferred cosmetic agent is characterized in that it contains one or more organic Ci-C6-alkoxysilanes of the formula (S-IV), RgSi(ORio)k(Rll)m (S-IV), where
  • Rg stands for a Ci-Ci2-alkyl group
  • R11 is a Ci-C6-alkyl group
  • k is an integer from 1 to 3
  • m is the integer 3 - k, and/or condensation products thereof.
  • the radical Rg is a C1-C12 alkyl group.
  • This Ci-Ci2-alkyl group is saturated and can be linear or branched.
  • Rg preferably stands for 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 is particularly preferably a methyl group, an ethyl group or an n-octyl group.
  • the radical R10 is a Ci-C6-alkyl group.
  • R10 particularly preferably represents a methyl group or an ethyl group.
  • the radical Rn is a Ci-C6-alkyl group.
  • Rn particularly preferably represents a methyl group or an ethyl group.
  • k is an integer of 1 to 3
  • m is an integer of 3 - k. If k is the number 3, then m is equal to 0. If k is the number 2, then m is equal to 1. If k is 1, then m is 2.
  • the cosmetic composition contains at least one organic C 1 -C 6 -alkoxysilane of the formula (S-IV) in which the radical k is the number 3. In this case, the remainder m stands for the number 0.
  • Particularly suitable organic silicon compounds of the formula (S-IV) are - methyltrimethoxysilane
  • n-dodecyltriethoxysilane also referred to as dodecyltriethoxysilane
  • octadecyltrimethoxysilane and/or octadecyltriethoxysilane also referred to as dodecyltriethoxysilane
  • a cosmetic agent is characterized in that it contains at least one organic C 1 -C 6 -alkoxysilane of the formula (S-IV), which is selected from the group consisting of
  • the cosmetic agent contains two structurally different alkoxysilanes.
  • a cosmetic agent is characterized in that it contains at least one alkoxysilane of the formula (S-I) and at least one alkoxysilane of the formula (S-IV).
  • hydrolysis or condensation products are, for example, the following compounds:
  • the hydrolysis reaction can also take place several times per Ci-C6-alkoxysilane used:
  • condensation reactions are (shown using the mixture of (3-aminopropyl)triethoxysilane and methyltrimethoxysilane): and or
  • condensation to form a dimer is shown in each case, but more extensive condensations to form oligomers having a plurality of silane atoms are also possible and also preferred.
  • Both partially hydrolyzed and completely hydrolyzed Ci-C6-alkoxysilanes of the formula (SI) can participate in these condensation reactions, which undergo a condensation with unreacted, partially or completely hydrolyzed Ci-C6-alkoxysilanes of the formula (SI).
  • the Ci-C6-alkoxysilanes of the formula (Sl) react with themselves.
  • both partially hydrolyzed and completely hydrolyzed Ci-C6-alkoxysilanes of the formula (Sl) can also participate in the condensation reactions, which a condensation with unreacted, partially or completely hydrolyzed Ci-C6-alkoxysilanes of the formula (S-IV) run through.
  • the Ci-C6 alkoxysilanes of the formula (Sl) react with the C1-C6 alkoxysilanes of the formula (S-IV).
  • Ci-C6-alkoxysilanes of the formula (S-IV) can also participate in the condensation reactions, which carry out a condensation with unreacted, partially or fully hydrolyzed Ci-C6-alkoxysilanes of the formula (S- IV) go through.
  • the Ci-C6-alkoxysilanes of the formula (S-IV) react with themselves.
  • the cosmetic agent can contain one or more organic Ci-C6-alkoxysilanes in different proportions. This is determined by the person skilled in the art depending on the desired application. In the case of coloring keratinic material, the amount can depend, for example, on the thickness of the silane coating on the keratinic material and on the amount of keratinic material to be treated.
  • Particularly storage-stable cosmetic products with a very good coloring result when used on keratin material could be obtained if the cosmetic product - based on its total weight - one or more organic Ci-C6-alkoxysilanes and / or the condensation products thereof in a total amount of 30 to 85 % by weight, preferably from 35 to 80% by weight, more preferably from 40 to 75% by weight, even more preferably from 45 to 70% by weight and very particularly preferably from 50 to 65% by weight .
  • the ready-to-use cosmetic agent contains other ingredients, in particular water, in addition to the pigment suspension according to the invention and the organic C 1 -C 6 alkoxysilane(s).
  • the cosmetic agent contains a class of highly reactive compounds which, when used, can undergo hydrolysis or oligomerization and/or polymerization.
  • a further advantage of the pigment suspension according to the invention is that it has no negative effect on the properties of the cosmetic agent and no negative effect on the properties of the organic C 1 -C 6 alkoxysilanes.
  • the user is preferably provided with all the means required in the form of a multi-component packaging unit (kit-of-parts).
  • a third subject matter of the present invention is therefore a multi-component packaging unit (kit-of-parts) comprising a first container made up separately from one another with an agent (a'), the agent (a') containing:
  • the cosmetic agent is prepared by mixing agent (a') and agent (a").
  • red iron oxide pigments (CI 77491) with an average particle diameter in the range from 2000 to 4000 nm were mixed with 10 g of ceteth-20 phosphate (INCI) and 80 g of distilled water. The mixture was transferred to a ball mill and the iron oxide red pigments were comminuted.
  • the particle size of the iron oxide red pigments was in the range from 150 to 700 nm. How was the particle size determined?
  • the pigment suspension obtained was stable for several weeks and the iron oxide red pigments showed no tendency to agglomerate.
  • a pigment suspension was prepared from 10 g iron oxide red pigments (CI 77491) with an average particle diameter in the range from 2000 to 4000 nm and 90 g PEG-12 Dimethicone (INCI) and subjected to a grinding process in a ball mill.
  • the particle size of the iron oxide red pigments was in the range from 150 to 700 nm, but the iron oxide red pigments agglomerated shortly after the end of the grinding process.
  • the cosmetic composition was prepared by mixing 5 g of composition (a') and 5 g of composition (a").

Abstract

L'invention concerne une suspension de pigments comprenant a) au moins un composé colorant du groupe des pigments, b) au moins un ester d'acide phosphorique et c) de l'eau. L'invention concerne également un agent cosmétique pouvant être obtenu par combinaison de la suspension de pigments avec un ou plusieurs alcoxysilanes en C1-C6 organiques et/ou leurs produits de condensation.
EP21729294.5A 2020-07-17 2021-05-27 Suspension de pigments et agent cosmétique préparé à l'aide de la suspension de pigments Pending EP4181859A1 (fr)

Applications Claiming Priority (2)

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DE102020208953.1A DE102020208953A1 (de) 2020-07-17 2020-07-17 Pigmentsuspension und kosmetisches Mittel, hergestellt unter Einsatz der Pigmentsuspension
PCT/EP2021/064185 WO2022012807A1 (fr) 2020-07-17 2021-05-27 Suspension de pigments et agent cosmétique préparé à l'aide de la suspension de pigments

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EP4181859A1 true EP4181859A1 (fr) 2023-05-24

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EP (1) EP4181859A1 (fr)
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DE102011089221A1 (de) * 2011-12-20 2013-06-20 Henkel Ag & Co. Kgaa Färbemittel mit direktziehenden Farbstoffen und Phospat-Tensiden
DE102018213814A1 (de) * 2018-08-16 2020-02-20 Henkel Ag & Co. Kgaa Verfahren zum Färben von keratinischem Material, umfassend die Anwendung von einer silicium-organischen Verbindung, einem Tensid und einem Pigment
DE102019211509A1 (de) * 2019-08-01 2021-02-04 Henkel Ag & Co. Kgaa Verfahren zur Behandlung von Keratinmaterial, umfassend die Anwendung eines organischen C1-C6-Alkoxy-silans und einer Aminosäure und/oder eines Aminosäurederivats
DE102019218231A1 (de) * 2019-11-26 2021-05-27 Henkel Ag & Co. Kgaa Mittel zum Färben von keratinischem Material mit Aminosilikon, farbgebender Verbindung und phosphorhaltigem Tensid

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