EP2773311A1 - Préparation cosmétique contenant des matières hydrophiles pulvérisées - Google Patents

Préparation cosmétique contenant des matières hydrophiles pulvérisées

Info

Publication number
EP2773311A1
EP2773311A1 EP12780741.0A EP12780741A EP2773311A1 EP 2773311 A1 EP2773311 A1 EP 2773311A1 EP 12780741 A EP12780741 A EP 12780741A EP 2773311 A1 EP2773311 A1 EP 2773311A1
Authority
EP
European Patent Office
Prior art keywords
substance
preparation
liquid
substances
hydrophilic
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.)
Ceased
Application number
EP12780741.0A
Other languages
German (de)
English (en)
Inventor
Horst Argembeaux
Stefan Biel
Katrin Counradi
Katja MÄTZOLD
Heike Miertsch
Svenja Lena Möllgaard
Ina Schornstein
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.)
Beiersdorf AG
Original Assignee
Beiersdorf AG
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 Beiersdorf AG filed Critical Beiersdorf AG
Publication of EP2773311A1 publication Critical patent/EP2773311A1/fr
Ceased legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0216Solid or semisolid forms
    • A61K8/022Powders; Compacted Powders
    • A61K8/0225Granulated powders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00Anti-perspirants or body deodorants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0216Solid or semisolid forms
    • A61K8/022Powders; Compacted Powders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0241Containing particulates characterized by their shape and/or structure
    • A61K8/0245Specific shapes or structures not provided for by any of the groups of A61K8/0241
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0241Containing particulates characterized by their shape and/or structure
    • A61K8/027Fibers; Fibrils
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/25Silicon; Compounds thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73Polysaccharides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73Polysaccharides
    • A61K8/731Cellulose; Quaternized cellulose derivatives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/001Preparations for care of the lips
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/08Anti-ageing preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q90/00Cosmetics or similar toiletry preparations for specific uses not provided for in other groups of this subclass
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30Characterized by the absence of a particular group of ingredients
    • A61K2800/31Anhydrous
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/49Solubiliser, Solubilising system

Definitions

  • the invention encompasses cosmetic preparations containing otherwise poorly soluble in the preparation hydrophilic active ingredients or active solutions
  • Cosmetic active ingredients or active solutions must be homogeneously distributed in a cosmetic formulation for good efficacy.
  • substances of different polarity can not be combined with each other stably. This succeeds at most with the help of emulsifiers, whose disadvantages, however, in addition to the costs of a higher irritation potential and a change (deterioration) of the sensory
  • Liquid substances can hardly be stably combined with solid particles. These separate due to the different densities. This problem may be prevented by the use of gelling agents or suspending aids which, in addition to higher costs, also lead to a deterioration of the sensory properties and to a lack of dispersibility.
  • liquid substances can not be combined with solid particles of matter which are soluble in the liquid substance.
  • solids properties are often desired, as the example shows sugar crystals in water.
  • hydrophilic raw materials such as aqueous deodorant substances or moisturizing substances such as glycerol
  • solubilizers can be used only in undissolved form as a powder or in dissolved form by using solubilizers.
  • emulsifiers are necessary in order to homogeneously mix hydrophilic and lipophilic phases homogeneously with one another.
  • WO 9617583 A1 describes moisturizers absorbed on silica carriers.
  • WO 2005 073300 A1 describes an improvement in the solubility of primary
  • Production of the porous body is carried out by separation of freeze-dried emulsions in disperse and continuous phases. This is not liquid on a carrier particle liquid is removed by freeze-drying, so that cavities are formed.
  • WO 2006 082536 A1 describes spray-dried preparations of active ingredients which are present in a gum arabic carrier mixed with a surfactant.
  • the technology is used to encapsulate menthol for chewing gum and tablets.
  • WO 2008 041 196 A1 describes a pulverized, non-liquid
  • Hair conditioning product wherein the liquid conditioner is absorbed on a solid carrier.
  • the powdered product is mixed with water before use.
  • Liquids or liquid mixtures by supercritical carbon dioxide (C02) without loss of valuable materials in powder form The CO2-containing liquids are suddenly released via a nozzle. This results in a very fine droplet spray at temperatures from - ⁇ ⁇ ' ⁇ to + 10 ° C.
  • a powdered carrier is added to the droplet spray.
  • the addition of carrier is the difference to the PGSS method. This carrier binds the fine droplets and a free-flowing powder is formed.
  • the resulting powder may have a liquid content of up to 99% by weight, based on the total mass of the powder.
  • any gas can be used in which dissolves the liquid to be pulverized.
  • the proportion of the carrier may therefore preferably be between 1 and 90% by weight.
  • any solid, powdery substance can be used, but it is advantageous if its particle size is less than 100 ⁇ m or if one of the carriers has a porosity, such as, for example, activated carbon or zeolites.
  • the advantages of the CPF process are that the low temperatures during the pulverization slow down or prevent degradation reactions, there is only low odor nuisance and the inert C02 acts as a protective gas for reactive substances.
  • the CPF process is already used in food technology, detergent technology, paint, paint and adhesive technology.
  • stabilizers (B) used are polysaccharides, chelators, glycerides or emulsifiers.
  • Carrier (C) may also be polysaccharides, in which case various stabilizers B) of C) different polysaccharides are used.
  • anhydrous or hydrophobic formulations and hydrophilic substances or mixtures such.
  • active ingredients without incorporating the use of emulsifiers, stabilizers or solvents stable.
  • the performance of the active ingredients may be reduced if they are in undissolved form in the formulation, so also come undissolved on the skin and then need to be solved on the skin.
  • the existing skin moisture or sweat is not sufficient here as a solvent.
  • the aim is therefore the use of active ingredients, which are pre-dissolved in hydrophilic solvent. These solutes can not readily be converted into anhydrous formulations
  • the invention is therefore a cosmetic or dermatological anhydrous preparation comprising one or more pulverulent products, comprising or consisting of one or more hydrophilic substances or substance mixtures (a.) Which are liquid at room temperature, pasty and / or meltable up to a temperature of 150 ° C., which are absorbed on one or more particulate carriers (b.).
  • the substance or substance mixture (a.) Alone is not soluble or sparingly soluble in the preparation.
  • the substance or substance mixture (a.) Is considered to be soluble if it is completely and homogeneously dissolved in the surrounding medium, ie the preparation, without further aids, such as emulsifiers or solubilizers. This alone means that the substance is not absorbed on the carrier (b.).
  • the supports (b.) are characterized by an average particle size in the range of 5 nm to 2 mm, a tamped density of 50 kg / m 3 to 1400 kg / m 3 and a spherical, fibrous, flaky and / or sponge-like particle shape.
  • the carriers used are powders which have a minimum of 5 nm and a maximum of 2 mm in the average particle size.
  • the tamped density is 50 kg / m 3 to 1400 kg / m 3 .
  • the tamped density is determined by the determination of the volume, wherein the tamping volume represents the smallest volume of a fixed amount of filler, which after stomping or compaction according to standardized
  • the porosity of the carrier is freely selectable from non-porous to highly porous.
  • the particle shape of the carriers is spherical, fibrous, flaky or sponge-like.
  • the carriers are usually used in cosmetics powder substances.
  • they are selected from the group of polysaccharides and silicic acids and their derivatives, as well as powder materials such as those in decorative cosmetics as a filler and
  • Sensoric additive can be used are possible.
  • the following list of advantageous carrier materials to be used should in no way be limiting:
  • Rice starch Rice starch, wheat starch and their derivatives (eg trade names: Amylogum CLS from Avebe, C * EmCap from Cerestar, DryFlo types from Akzo Nobel
  • Celluloses and derivatives eg. B. Avicel types of FMC Biopolymer, Arbocel, Vitacel, Vivapur types from J. Rettenmaier & Söhne GmbH
  • Other fillers such as Lauroyl Lysine (Amihope LL), nylon types (eg Orgasol types from Arkema) or silicates such as Calsium Silicate (Hubersorb from Huber) can be used.
  • silicas preference is given to using types from the Aerosils series from Evonik Degussa.
  • the powdery products comprise the hydrophilic substances or mixtures (a.) And the particulate carriers (b.) On which they are absorbed, or preferably consist only of these two components a.) And b.).
  • emulsifiers or stabilizers in the powdery products can be dispensed with.
  • Another preferred criterion is that the powdered products are produced according to the CPF process.
  • the hydrophilic substance or the mixture of substances is characterized in that it alone is not soluble or sparingly soluble in the preparation.
  • a hydrophilic substance or a hydrophilic substance mixture is characterized in that it is miscible with water. Solubility is the property of a substance to dissolve homogeneously in a liquid or melt.
  • Substance or mixtures of substances which can not be completely or only inhomogeneously dissolved in the solvent are said to be insoluble or poorly soluble.
  • hydrophilic substances or substance mixtures also referred to as active ingredients or active solutions
  • Auxiliaries such as solubilizers or emulsifiers, in formulations in which they are not soluble, homogeneous, ie. without incorporating phase separation.
  • That a substance which is in principle insoluble in a cosmetic or dermatological preparation is converted by absorption onto a carrier into a pulverulent product, the substance insoluble in the hydrophobic formulation being bound to the carrier as a hydrophilic solution.
  • the powder loaded with active ingredients does not dissolve in the preparation, but is present in the formulation as a sensory additive as a powder, only additionally loaded with liquid.
  • the pulverization is advantageously carried out according to the CPF method. It is hereby expressly referred to in the publications WO 99 17868 A1, EP 1 021 241 A1 and EP 0 744 992 A1 CPF method referred to. The disclosures made therein are also in full content of the present application.
  • the CPF process makes it possible to produce powdery solids from liquids.
  • the process principle is to dissolve a gas in the liquid to be pulverized under elevated pressure, preferably until a gas-saturated solution is obtained. Compared to pure liquid, such a solution has a number of favorable
  • the pressurized liquid / gas solution is then a
  • Relaxation organ in the relaxation organ or thereafter, in particular shortly after the relaxation organ, a solid, powdery excipient, the particulate carrier admixed.
  • any gas which dissolves sufficiently in the liquid substance or substance mixture to be pulverized can be used as the gas.
  • the gas carbon dioxide, a hydrocarbon, in particular methane, ethane, propane, butane, ethene, propene or a halogenated hydrocarbon, an ether, an inert gas, in particular nitrogen, helium or argon, a gaseous oxide, in particular nitrous oxide or sulfur dioxide, and ammonia be used.
  • a mixture of two or more of the aforementioned gases may be used.
  • the increased pressure at which the gas is dissolved in the liquid or mixture of substances may be in the range of 5 bar to 800 bar, but preferably the pressure is in the range of 10 bar to 350 bar and more preferably in the range of 20 bar to 250 bar.
  • the dissolution of the gas in the liquid or mixture of substances is accelerated by mixing the gas with the liquid or mixture of substances.
  • This mixing can be achieved, for example, by shaking or rolling the pressure vessel, in which the liquid to be pulverized is placed.
  • Pressure vessel resulting solution are stirred by means of a stirrer.
  • Another way to achieve a good mixing of the liquid to be pulverized with the gas, is the liquid phase contained in the pressure vessel and / or the
  • the substance to be pulverized, the active solution, is bound to the carrier particle by adhesion, impregnation and / or agglomeration.
  • the CPF procedure leads
  • the active solution can be released from the particulate carrier as soon as the loaded particles come into an environment in which the active solution is soluble or to which an affinity exists.
  • the hydrophilic substances can combine with the sweat on the skin and spread over the skin. The release then takes place with a time delay and thus leads to a long-lasting effect.
  • the improved solubility is comparable to instant coffee over instant coffee.
  • mixture, active ingredient or active solution according to the invention are all liquid at room temperature, pasty and / or meltable up to a temperature of 150 ° C materials to understand.
  • mixtures or active solutions include solutions such as e.g. aqueous surfactant solutions which may contain other ingredients, or dissolved in water
  • Plant extracts or dissolved active substances such as. B. antibacterial and antiperspirant agents.
  • the substance to be pulverized can be dissolved as pure substance (without solvent) or in a suitable solvent, eg. As in hydrophilic drugs water or propylene glycol, are present.
  • polar solvents water, volatile alcohols (e.g., ethanol, isopropanol), as well as humectants (polyhydric alcohols such as glycerol, propylene glycol, butylene glycol), generally alkanediols, such as
  • Preservative aids e.g., caprylyl glycol, pentylene glycol
  • low molecular weight PEGs e.g., PEG-8
  • the active solution is preferably liquid at room temperature, but may also be pasty to solid, if it is then melted at a temperature up to 150 ° C.
  • the viscosity of the active solution can also be adjusted via hydrophilic thickeners commonly used in cosmetics, such as polymers.
  • Preferred cosmetic active ingredients which may be contained in the preparation and are preferably pulverized by means of CPF are to be selected from the group of
  • Deodorant agents such as methyl phenylbutanol, butyloctanoic acid, polyglyceryl-2 caprate, polyaminopropyl biguanide, octenidine HCl, silver citrate or other active ingredients such as Q10, panthenol, bisabolol, calcium pantothenate, niacinamide, and / or piroctone olamine can also be selected.
  • water-soluble UV filters can be used, for.
  • Suitable humectants are glycerol and glycols. These substances in particular require no solvent and can be powdered directly as hydrophilic substances on the carrier and then added to the anhydrous or hydrophobic preparation
  • agents may be selected from the group of extracts, such as e.g. from / by Cymbopogon Citratus, Maris Limus, Ostrea Shell, Cucumber.
  • hydrophilic deodorizers can now be incorporated into anhydrous formulations (oil-based), e.g. in aerosols.
  • hydrophilic skin moisturizers such as glycerin
  • anhydrous formulas such as e.g. in lip products.
  • the preparations according to the invention are preferably anhydrous. However, a residual amount of water may be present in the preparation according to the invention as a result of the raw material and may therefore be unavoidable. As anhydrous therefore be within the meaning of the invention
  • compositions containing less than 5% by weight of water (not including water of crystallization), preferably less than 2% by weight of water and in particular less than 1% by weight of water, based on the total mass of the preparation.
  • aerosol preparations for sweat reduction can also be provided in this way.
  • the preparation according to the invention is applied to the skin, for example in the armpit.
  • the sweat hits the pulverized substances or substance mixtures, such as
  • an active ingredient-containing emulsion for example, an active ingredient-containing emulsion, and leads to its rehydration.
  • the sweat is absorbed and at the same time released possibly contained active substances, which serve for sweat inhibition or skin care.
  • the cosmetic and dermatological preparations according to the invention may further contain cosmetic adjuvants and other active ingredients such as are commonly used in such preparations, for.
  • cosmetic adjuvants and other active ingredients such as are commonly used in such preparations, for.
  • Color pigments, thickeners, moisturizing and / or moisturizing substances, fats, oils, waxes or other customary constituents of a cosmetic or dermatological formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives if the additive does not have the required solubility properties impaired.
  • the proportions relate to parts by weight, based on the total mass of the preparation, unless otherwise disclosed.
  • a SNIFF test was performed, whereby trained persons smelled and checked how the deodorized armpit smelled compared to the other, which for comparison purposes remains deodorized.
  • the preconditioning time is 10 days. During this time, the subjects in the armpits may use any deodorant products and wash only with unscented soap.
  • the first odor value (TO) is determined 24 hours after the subjects have washed with unscented soap. After washing again, the product is applied in an underarm
  • the other armpit remains untreated. 4h (t1) and 24h (t2) thereafter, the underarm odor is scored on a 5-step scale (0 no odor, 5 very strong odor). To evaluate deodorant performance, the SNIFF scores of both armpits are compared for times t1 and t2. The larger the difference, the better the performance.
  • Myristyl myristates 3.42 3.80 3.42

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Physics & Mathematics (AREA)
  • Geometry (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Cosmetics (AREA)

Abstract

Dans une préparation cosmétique ou dermatologique anhydre, une matière en principe insoluble est transformée par absorption sur un support en un produit pulvérulent qui est soluble dans la préparation. Lesdites préparations anhydres contiennent un ou plusieurs matières ou mélanges de matières hydrophiles liquides à température ambiante, pâteux et/ou fusibles jusqu'à une température de 150 °C, qui sont absorbés sur un ou plusieurs supports particulaires. La matière hydrophile ou le mélange de matières hydrophiles sont à eux seuls non solubles ou difficilement solubles dans la préparation et les supports sont caractérisés par une taille des particules de l'ordre de 5 nm à 2 mm, une densité du produit tassé de 50 kg/m³ à 1400 kg/m³ et une forme des particules de type sphère, fibre, flocon et/ou éponge.
EP12780741.0A 2011-11-03 2012-11-02 Préparation cosmétique contenant des matières hydrophiles pulvérisées Ceased EP2773311A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102011085694A DE102011085694A1 (de) 2011-11-03 2011-11-03 Kosmetische Zubereitung mit pulverisierten hydrophilen Stoffen
PCT/EP2012/071681 WO2013064611A1 (fr) 2011-11-03 2012-11-02 Préparation cosmétique contenant des matières hydrophiles pulvérisées

Publications (1)

Publication Number Publication Date
EP2773311A1 true EP2773311A1 (fr) 2014-09-10

Family

ID=47115983

Family Applications (1)

Application Number Title Priority Date Filing Date
EP12780741.0A Ceased EP2773311A1 (fr) 2011-11-03 2012-11-02 Préparation cosmétique contenant des matières hydrophiles pulvérisées

Country Status (5)

Country Link
US (1) US10010489B2 (fr)
EP (1) EP2773311A1 (fr)
BR (1) BR112014007409B1 (fr)
DE (1) DE102011085694A1 (fr)
WO (1) WO2013064611A1 (fr)

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WO2019038101A1 (fr) 2017-08-23 2019-02-28 Unilever Plc Composition antitranspirante anhydre sous forme d'aérosol
DE202018004125U1 (de) 2018-09-05 2018-10-11 Beiersdorf Ag Alkylamidothiazole in Polypropylen-haltigen Packmitteln
DE102019200138A1 (de) 2019-01-08 2020-07-09 Beiersdorf Ag Zubereitung mit Vinylamine/N-vinylformamide Copolymer beschichteteten Cellulosepartikeln
DE102019200135A1 (de) 2019-01-08 2020-07-09 Beiersdorf Ag Zubereitung mit Vinylamine/N-vinylformamide Copolymer beschichteten Siliciumdioxidpartikeln
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MX2021014159A (es) * 2019-05-21 2022-01-04 Unilever Ip Holdings B V Composiciones cosmeticas para un enfoque suave.
MX2022010655A (es) 2020-02-28 2022-10-21 Church & Dwight Co Inc Composicion de champu en seco.

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Also Published As

Publication number Publication date
US10010489B2 (en) 2018-07-03
US20140294976A1 (en) 2014-10-02
WO2013064611A1 (fr) 2013-05-10
DE102011085694A1 (de) 2013-05-08
BR112014007409B1 (pt) 2019-06-25
BR112014007409A2 (pt) 2017-04-04
CN104023693A (zh) 2014-09-03

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