WO2013000742A2 - Utilisation d'élastomères de silicone dans des préparations cosmétiques - Google Patents

Utilisation d'élastomères de silicone dans des préparations cosmétiques Download PDF

Info

Publication number
WO2013000742A2
WO2013000742A2 PCT/EP2012/061486 EP2012061486W WO2013000742A2 WO 2013000742 A2 WO2013000742 A2 WO 2013000742A2 EP 2012061486 W EP2012061486 W EP 2012061486W WO 2013000742 A2 WO2013000742 A2 WO 2013000742A2
Authority
WO
WIPO (PCT)
Prior art keywords
oil
acetate
methyl
alpha
sio
Prior art date
Application number
PCT/EP2012/061486
Other languages
German (de)
English (en)
Other versions
WO2013000742A3 (fr
Inventor
Svea WISCHHÖFER
Kerstin Skubsch
Celina Storbeck
Manuela Köhler
Antonia Wagner
Stefanie Von Thaden
Björn HEUER
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
Priority to EP12727668.1A priority Critical patent/EP2723315A2/fr
Publication of WO2013000742A2 publication Critical patent/WO2013000742A2/fr
Publication of WO2013000742A3 publication Critical patent/WO2013000742A3/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—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
    • A61K8/895—Polysiloxanes containing silicon bound to unsaturated aliphatic groups, e.g. vinyl dimethicone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier 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
    • A61Q17/005—Antimicrobial preparations
    • 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
    • A61K2800/52—Stabilizers
    • A61K2800/524—Preservatives

Definitions

  • the present invention relates to the use of silicone elastomers in cosmetic preparations.
  • Preservatives are substances or substances which, when used in appropriate concentration, are intended to protect pharmaceutical and / or cosmetic preparations against, in particular, microbially caused adverse changes. Preservatives or mixtures of preservatives must act against bacteria, yeasts and fungi.
  • a preservative is generally subject to the following requirements:
  • Microorganisms may be present in cosmetic products primarily for production reasons or secondarily pass through the consumer into the cosmetic product.Therefore, the manufacturer of the cosmetic product must ensure that the finished product also on the entire period of use is safe (see Technical Rules for
  • the preservatives generally need to be further dissolved in the preparation in order to be effective. Since most preservatives are better fat-soluble than water-soluble it happen that z. For example, in an emulsion whose aqueous phase is to be preserved, the preservative incorporated into the aqueous phase migrates in the course of storage in the fatty phase and thus the preservation of the aqueous phase is in question.
  • preservatives in cosmetics is regulated by the Cosmetics Ordinance (KVO) and the EC Directive 76/768 in Germany and the European Union. Currently, 48 substances / mixtures are authorized as permanent and 4 temporary as preservatives in the EU.
  • Formaldehyde releasers are preservatives which split off formaldehyde during the manufacture, storage or use of pharmaceutical or cosmetic agents and therefore have a preservative effect.
  • formaldehyde Abspaltern the formaldehyde is in the form of ethereal compounds with alcohol, eg. B. as acetal or hemiacetal ago. Such compounds break down monomerically germicidal formaldehyde.
  • Hemiacetals e.g. As the Semiformale of polyalcohols, such as ethylene glycol, 1, 2-propylene glycol, or butyl triglycol, are particularly suitable.
  • the combination of such acetals with a number of methylol compounds leads to active substances, for example 2,4-dimethyl-6-acetoxy-m-dioxane and 2,4-dimethyl-6-propionoxy-m-dioxane.
  • parabens methyl-, ethyl-, propyl-, butylparaben
  • formaldehyde-releasing agents parabens (methyl-, ethyl-, propyl-, butylparaben) are regularly used in cosmetics as preserving agents. But these too
  • (A) a S ⁇ - containing polysiloxane of the formula R 3 SiO (R ' 2 SiO) a (R "l-ISiO) b SiR 3 and, optionally, a Si-H containing polysiloxane of the formula HR 2 SiO (R'2SiO ) c SiR 2 H or the formula HR 2 SiO (R ' 2 SiO) a (R''l-ISiO) b SiR 2 H,
  • R, R 'and R " alkyl groups having 1 to 6 C atoms
  • Solvent selected from the group consisting of (i) organic components, (ii) components containing a silicon atom and any mixtures thereof,
  • reaction is carried out until a gel is formed by cross-linking by the addition of ESi-H to the double bonds of the alpha, omega-diene
  • R 2 hydrogen
  • the object is achieved by the use of a Siloxanelastomergelgels,
  • (A) a S ⁇ - containing polysiloxane of the formula R 3 SiO (R ' 2 SiO) a (R "l-ISiO) bSiR3 and, optionally containing a Si-H containing polysiloxane of the formula HR 2 SiO (R'2SiO) c SiR 2 H or the formula HR 2 SiO (R'2SiO) a (R "HSiO) b SiR 2 H,
  • R, R 'and R " alkyl groups having 1 to 6 C atoms
  • reaction is carried out until a gel is formed by cross-linking by the addition of ESi-H to the double bonds of the alpha, omega-diene
  • R 2 hydrogen
  • siloxane elastomers according to the invention are not preservatives within the meaning of the Cosmetics Ordinance, but are primarily incorporated into the preparations for other purposes.
  • R 3 is selected from polyethers, pentylene, hexylene, heptylene, octylene, nonylene, decylene, dodecylene, tetradecylene and mixtures thereof.
  • the siloxane elastomer II it is preferred in the case of the siloxane elastomer II) according to the invention if the compound contains 0.01 to 90 mol% cross-linker.
  • the siloxane elastomer II) according to the invention can advantageously be prepared by the following process:
  • each R 1 is independently a monovalent hydrocarbon group of 1 to 30 carbon atoms, a is 265 to 2,000 and d is 1 to 250
  • an additional second ⁇ Si-containing polysiloxane is present, which is selected from HR 1 2 SiO (R 1 2 SiO) e SiR 1 2 H,
  • (b) is selected from 1, 4-pentadiene, 1, 5-hexadiene, 1, 6-heptadiene, 1, 7-octadiene, 1, 8-nonadiene, 1, 9-decadiene, 1, 1 1 -dodecadiene, 1, 13-tetradecadiene and 1, 19-eicosadiene, 1, 3-butadiyne, 1, 5-hexadiyne (dipropargyl) and 1, hexene-5-yn.
  • siloxane elastomer gels according to the invention can be obtained, for example, from Dow Corning under the trade name 9040 Silicone Elastomer Blend, 9041 Silicone
  • Elastomer Blend or 9045 Silicone Elastomer Blend can be purchased.
  • other elastomer gels such as, but not limited to, the Silsoft Silicone Gel from Momentive are also within the scope of the invention.
  • the use according to the invention is advantageously characterized in that the preparation contains the siloxane elastomer gel in a concentration of 0.1 to 25
  • the use according to the invention is preferably characterized in that the preparation contains the siloxane elastomer gel in a concentration of 5 to 20% by weight, based on the total weight of the preparation.
  • Embodiments of the present invention which are advantageous according to the invention are characterized in that the preparation is in the form of an emulsion. That's it
  • the preparation is in the form of an O / W emulsion.
  • preparation according to the invention is in the form of an O / W emulsion, it is
  • Glyceryl stearate citrate glyceryl stearate (self-emulsifying), stearic acid, stearate salts,
  • preparations which contain no PEG (polyethylene glycols) or PEG derivatives are preferred.
  • the use according to the invention is advantageously characterized in that the preparation is free of formaldehyde-releasing preservatives. These include, for example, dimethylol glycol, dimethylol urea, DMDM-hydantoin, quaternium-15 sodium hydroxymethylglycinate, tetramethylol glycoluril.
  • the use according to the invention is advantageously characterized in that the preparation is free of parabens. These include, for example, methyl, ethyl, propyl and butylparaben.
  • the oil or lipid phase according to the invention may contain all oils, fats, waxes and / or lipids customary in cosmetic preparations.
  • the aqueous phase of the preparations according to the invention may advantageously comprise customary cosmetic auxiliaries, for example alcohols, in particular those of low C number, preferably ethanol and / or isopropanol or polyols of low C number and their ethers, preferably propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether, diethylene glycol monomethyl or monoethyl ether and analogous products, foam stabilizers, electrolyte, self-tanning agents, etc.
  • customary cosmetic auxiliaries for example alcohols, in particular those of low C number, preferably ethanol and / or isopropanol or polyols of low C number and their ethers, preferably propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol mono
  • the composition according to the invention advantageously contains one or more humectants (moisturizers).
  • Moisturizers are substances or mixtures of substances which give cosmetic preparations the property of reducing the moisture release of the horny layer (also called transepidermal water loss (TEWL) after application or spreading on the skin surface) and / or hydrating the horny layer positively influence.
  • TEWL transepidermal water loss
  • humectants in the context of the present invention are:
  • glycerol for example, glycerol, lactic acid and / or lactates, especially sodium lactate,
  • hyaluronic acid, chitosan and / or a fucose-rich polysaccharide which is deposited in the Chemical Abstracts under the registration number 178463-23-5 and, for example, are particularly advantageous.
  • B. under the name Fucogel®1000 of the company SOLABIA SA is available.
  • Moisturizers can also be used advantageously as anti-wrinkle active ingredients for protection against skin changes, as described, for example, in US Pat. B. occur during skin aging, can be used.
  • the inventive preparation one or more humectants in a total concentration of 0, 1 to 20% by weight and preferably in a total concentration of 0.5 to 10% by weight, based in each case on the total weight of Preparation containing.
  • the cosmetic preparations according to the invention may also advantageously, although not necessarily, contain fillers which are e.g. B. the sensory and cosmetic
  • Starch and starch derivatives such as, for example, tapioca starch,
  • Pigments which have neither primarily a UV filter effect nor a coloring effect (such as. For example, boron nitride etc.) and / or Aerosils ® (CAS no. 7631-86-9) and / or talc.
  • the preparation as further ingredients one or more compounds selected from the group of compounds alpha-lipoic acid, folic acid, phytoene, D-biotin, coenzyme Q10, alpha-glucosylrutin, carnitine, carnosine, polydocanol, natural and / or synthetic isoflavonoids, flavonoids, creatine, creatinine, taurine, caffeine, menthol, ⁇ -alanine, tocopheryl acetate, urea; hyaluronic acid; dihydroxyacetone; 8-hexadecene-1, 16-dicarboxylic acid, glycyrrhetinic acid, glucosylglycerides and / or licochalcone A.
  • UV filters selected from the group of compounds phenylene-1, 4-bis (2-benzimidazyl) -3,3'-5,5'-tetrasulfonklaresalze; 2-phenylbenzimidazole-5-sulfonic acid salts; 1,4-di (2-oxo-10-sulfo-3-bornylidenemethyl) benzene and its salts; 4- (2-oxo-3-bomylidenemethyl) benzene sulfonic acid salts; 2-methyl-5- (2-oxo-3-bornylidenemethyl) sulfonic acid salts; 2,2'-methylene-bis (6- (2H-benzotriazol-2-yl) -4- (1,1,3,3-tetramethylbutyl) -phenol); 2- (2H-Benzotriazol-2-yl) -4-methyl-6- [2-methyl-3- [1,3,3,3-tetramethyl-1 - [(trimethyl)
  • Terephthalidendicamphersulfonklare 4- (dimethylamino) benzoic acid (2-ethylhexyl) ester; 4- (dimethylamino) benzoic acid amyl ester; 4-Methoxybenzalmalon-klaredi (2-ethylhexyl) ester; 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone;2,2'-dihydroxy-4-methoxybenzophenone; 2-ethylhexyl 2-hydroxybenzoate; 3- (4- (2,2-ethoxycarbonylvinyl) phenoxy) propenyl) methoxysiloxane / dimethylsiloxane copolymer; Dioctylbutylamidotriazone (INCI: diethylhexyl-butamidotriazone); 2,4-bis- [5-1 (dimethylpropyl) benzoxazol-2-yl- (4
  • preservative-free formulations were prepared and their microbiological stability was tested in the preservation stress test.
  • the microbial stability was determined as follows: Evidence of the microbiological stability of a cosmetic product is usually demonstrated by testing for adequate preservation (preservation stress test). These are samples of a cosmetic product to be tested with test microbes
  • the Absterbekinetiken be improved.
  • less than 100 cfu / g were already detected after 7 days, whereas in Formula 1 this value is only obtained after 28 days.
  • the Absterbekinetik has been improved by using a Siloxanelastomergelgel the Absterbekinetik / g with respect to the gram negative bacteria.
  • the formulations with the siloxane elastomer gel according to the invention are more microbially stable. This is especially true for Candida albicans and the gram negative bacteria. Examples
  • Glycerine 7.50 7.50 10.00 10.00 10.00

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Silicon Polymers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne l'utilisation d'un gel d'élastomère de siloxane, I) préparé par réaction A) d'un polysiloxane contenant ≡Si-H représenté par la formule R3SiO(R'2SiO)a(R''HSiO)bSiR3 et, éventuellement d'un polysiloxane contenant ≡Si-H représenté par la formule HR2SiO(R'2SiO)cSiR2H ou par la formule HR2SiO(R'2SiO)a(R''HSiO)bSiR2H, où R, R' et R'' = groupes alkyle portant 1 à 6 atomes de C, a = 0-250, b = 1-250, et c = 0-250, (B) d'un alpha, oméga-diène représenté par la formule CH2=CH(CH2)xCH=CH2 où x = 1-20, la réaction étant réalisée en présence d'un catalyseur platine, et C) d'un solvant choisi dans le groupe composé i) de constituants organiques, ii) de constituants contenant un atome de silicone et leurs mélanges, la réaction étant réalisée jusqu'à ce qu'un gel se forme par réticulation transversale par addition de ≡Si-H aux liaisons doubles de l'alpha, oméga-diène ou II) ayant la structure suivante (AA) où R1 = reste alkyle C1 à C30, R2 = hydrogène, R3 = une réticulation transversale -E-Y-E-, l'autre extrémité de la réticulation transversale étant connectée à une deuxième chaîne d'élastomère de silicone, chaque E représentant un groupe bivalent choisi parmi les groupes -CH2-CH2- ou -CH=CH- et Y étant un groupe hydrocarbure bivalent, un siloxane ou une combinaison de ces deux, a = 265-2000, b = 0-249, c = 1-250, à la condition que b+c ≤ 250, le gel étant trempé dans un solvant, dans des préparations cosmétiques pour la protection contre les attaques microbiennes.
PCT/EP2012/061486 2011-06-27 2012-06-15 Utilisation d'élastomères de silicone dans des préparations cosmétiques WO2013000742A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP12727668.1A EP2723315A2 (fr) 2011-06-27 2012-06-15 Utilisation d'élastomères de silicone dans des préparations cosmétiques

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102011078097.1 2011-06-27
DE201110078097 DE102011078097A1 (de) 2011-06-27 2011-06-27 Verwendung von Silikonelastomeren in kosmetischen Zubereitungen

Publications (2)

Publication Number Publication Date
WO2013000742A2 true WO2013000742A2 (fr) 2013-01-03
WO2013000742A3 WO2013000742A3 (fr) 2013-12-05

Family

ID=46298423

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2012/061486 WO2013000742A2 (fr) 2011-06-27 2012-06-15 Utilisation d'élastomères de silicone dans des préparations cosmétiques

Country Status (3)

Country Link
EP (1) EP2723315A2 (fr)
DE (1) DE102011078097A1 (fr)
WO (1) WO2013000742A2 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0393511A2 (fr) * 1989-04-17 1990-10-24 Dow Corning Toray Silicone Company Ltd. Particules de caoutchouc de silicone antimicrobiennes
US5466726A (en) * 1993-08-27 1995-11-14 Shin-Etsu Chemical Co., Ltd. Antibacterial, antifungal silicone rubber composition
US5654362A (en) * 1996-03-20 1997-08-05 Dow Corning Corporation Silicone oils and solvents thickened by silicone elastomers
US20040044121A1 (en) * 2002-08-27 2004-03-04 Kadlec Donald Anthony Silicone elastomers compositions
EP2181699A1 (fr) * 2008-10-22 2010-05-05 Beiersdorf AG Formule cosmétique dotée de siloxane-élastomères pour l'amélioration de la stabilité microbiologique

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0393511A2 (fr) * 1989-04-17 1990-10-24 Dow Corning Toray Silicone Company Ltd. Particules de caoutchouc de silicone antimicrobiennes
US5466726A (en) * 1993-08-27 1995-11-14 Shin-Etsu Chemical Co., Ltd. Antibacterial, antifungal silicone rubber composition
US5654362A (en) * 1996-03-20 1997-08-05 Dow Corning Corporation Silicone oils and solvents thickened by silicone elastomers
US20040044121A1 (en) * 2002-08-27 2004-03-04 Kadlec Donald Anthony Silicone elastomers compositions
EP2181699A1 (fr) * 2008-10-22 2010-05-05 Beiersdorf AG Formule cosmétique dotée de siloxane-élastomères pour l'amélioration de la stabilité microbiologique

Also Published As

Publication number Publication date
EP2723315A2 (fr) 2014-04-30
WO2013000742A3 (fr) 2013-12-05
DE102011078097A1 (de) 2012-12-27

Similar Documents

Publication Publication Date Title
EP2419074B1 (fr) Utilisation des siloxanes ramifiés et organo-modifiés pour la preparation des compositions cosmetiques ou pharmaceutiques
EP2000123B1 (fr) Compositions cosmétiques stables et peu visqueuses comprenant des esters quaternaires et/ou des dialkyles quaternaires
EP3122316B1 (fr) Émulsions de type aqueux contenant du 4-hydroxyacétophénone et des émulsifiants anioniques
WO2008155080A2 (fr) Copolymères de styrènes/acrylates utilisés dans les agents cosmétiques de protection solaire
EP1360955A2 (fr) Composition cosmétique avec un élastomère silicone et un latex de polymère épaississant
DE112019007080T5 (de) Öl-in-Wasser-Sonnenschutzzusammensetzung
EP1476130A1 (fr) Pr parations contenant un diol
EP2942045A1 (fr) Formes galéniques cosmétiques en forme de perle
DE102007024377A1 (de) Desinfizierendes Hautbehandlungsmittel
EP2723312B1 (fr) Amidon de tapioca utilisé dans des préparations cosmétiques contenant des élastomères de silicone
WO2013000742A2 (fr) Utilisation d'élastomères de silicone dans des préparations cosmétiques
DE10239647A1 (de) Kosmetische O/W-Emulsion
WO2008119502A1 (fr) Préparation cosmétique contenant des polysaccharides modifiés hydrophobes et un principe actif ionique
DE102019201362A1 (de) Partikeldispersion enthaltend Polymere
WO2013000743A2 (fr) Nouvelle utilisation d'élastomères de silicone dans des préparations cosmétiques
DE102014208440B4 (de) Zubereitungen mit einer äußeren Gelphase und einer inneren partikulären Phase, die stabilisierte oxidations- und/oder UV-empfindliche Wirkstoffe enthält
EP2440173A2 (fr) Produit nettoyant cosmétique à effet désodorisant
DE102004027099A1 (de) Klare und wässrige kosmetische und dermatologische Zubereitungen mit einem Gehalt an öllöslichen UV-Filtersubstanzen
WO2008119448A1 (fr) Préparation cosmétique comprenant des polysaccharides modifiés hydrophobiquement et des filtres uv hydrosolubles
EP2942046B1 (fr) Préparations ayant une phase de gel externe et une phase particulaire interne contenant des agents actifs sensibles aux UV et/ou d'oxydation stabilisés
DE102021129474A1 (de) Kosmetische Zubereitung zur Pflege und Behandlung der periokulären Haut
DE102019201364A1 (de) Kosmetisches Produkt enthaltend Kapseln
DE202021106186U1 (de) Kosmetische Zubereitung zur Pflege und Behandlung der periokulären Haut
DE102012200071A1 (de) Duftstabile, wasserfeste kosmetische Zubereitung
EP3586816A1 (fr) Produit cosmétique comprenant un produit cosmétique ou dermatologique contenant des perles visibles, suspendues dans un support transparent, liquide ou gélifié, les perles encapsulant une substance active cosmétique ou dermatologique développant une propre odeur désagréable

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 2012727668

Country of ref document: EP