EP3658104A1 - Émulsions eau dans l'huile contenant des cétyl-diglycéryl-tris-(triméthylsiloxy)silyléthyldiméthicones comme émulsifiant et contenant des composés aromatiques - Google Patents

Émulsions eau dans l'huile contenant des cétyl-diglycéryl-tris-(triméthylsiloxy)silyléthyldiméthicones comme émulsifiant et contenant des composés aromatiques

Info

Publication number
EP3658104A1
EP3658104A1 EP18729357.6A EP18729357A EP3658104A1 EP 3658104 A1 EP3658104 A1 EP 3658104A1 EP 18729357 A EP18729357 A EP 18729357A EP 3658104 A1 EP3658104 A1 EP 3658104A1
Authority
EP
European Patent Office
Prior art keywords
group
formula
branched
oil
water
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP18729357.6A
Other languages
German (de)
English (en)
Inventor
Delphine CHANTY
Thomas Raschke
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 EP3658104A1 publication Critical patent/EP3658104A1/fr
Withdrawn legal-status Critical Current

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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/064—Water-in-oil emulsions, e.g. Water-in-silicone emulsions
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/894—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin

Definitions

  • the present invention relates to a cosmetic preparation preparations in the form of water-in-oil emulsions based on cetyl diglyceryl tris (trimethylsiloxy) silyl ethyldimethicone as an emulsifier, which have a content of low molecular weight aromatics.
  • agents are used, for example, stimulate the activity of skin cells, but also increasingly used UV filters that block especially responsible for skin aging UVA rays. All these ingredients pose a great challenge for a pleasant sensory, as they remain as a film on the skin after evaporation of the volatile constituents of the formulation, and sensed by the consumer sensory there.
  • the sensible residues are often described negatively and prevent the feeling that the product is completely "absorbed" in the skin.
  • W / O emulsions are often used by consumers to condition or treat dry skin.
  • W / O emulsions also offer advantages when incorporating color pigments, eg in tinted day creams and make-up.
  • W / O emulsions are negative in that they leave an oily residue on the skin that is slow to penetrate.
  • their physical Stability often limited. This is especially problematic when W / O emulsions with aromatics are to be formulated.
  • Silicone-based emulsifiers almost exclusively contain PEG- and PPG-containing groups as a hydrophilic component. Typical representatives are Cetyl PEG / PPG-10/1 Dimethicone (Abil EM 90, 180) from Evonik or PEG-10 Dimethicone (ES-5612 Formulation Aid) from Dow Corning. These examples are successful and long-established W / O emulsifiers in the market. The choice of PEG-free silicone emulsifiers is limited. For example, KF-6100, KF-6104, KF-6105 or KSG-710, KSG-810, KSG-820, KSG-830 or KSG-840 from Shin Etsu or Abil EM 120 from Evonik can be found here.
  • W / O silicone emulsifiers are used in high concentrations of several percent.
  • the choice of oils for W / O emulsions and in particular for W / Si emulsions is limited, since a high proportion of non-polar oils is required for good long-term stability. Therefore, in W / Si emulsions essentially silicone oils and / or liquid hydrocarbons are used.
  • the object of the present invention is therefore to provide a stable (storage-stable, transport-stable, long-term stable) water-in-oil (W / O) emulsion which can be sensory-attractive, PEG-free and can be incorporated into the aromatics but meets all the requirements for a modern facial care product.
  • W / O water-in-oil
  • a particularly interesting emulsifier is sold by Dow Corning under the INCI name cetyl diglyceryl tris- (trimethylsiloxy) silylethyldimethicone and under the trade designation ES-5600.
  • Low molecular weight aromatics are common ingredients in cosmetic formulations. Their structure and function can be very different. Low molecular weight aromatics can be used in the group of terpenes as part of perfume oils. Again, other low molecular weight aromatics have antimicrobial or antioxidant properties. Many of these substances are good solvents which adversely affect the stability of W / O emulsions. An example of this is benzyl alcohol.
  • X can denote a branched or unbranched C 1 -C 4 -alkyl chain, a hydroxy group or an O-group, and the dashed bond indicates a double bond, if X denotes an O-group, and R independently of X a branched one or unbranched C 1 -C 4 -alkyl chain, a branched or unbranched C 1 -C 4 -alkyl chain bridged via an oxygen atom or a hydroxy group.
  • water-in-oil emulsions advantageously contain from 0.1 to 10.0% by weight, preferably from 0.2 to 5.0% by weight, particularly preferably from 0.5 to 4.0% by weight on the total weight of the preparation, on cetyl diglyceryl tris (trimethylsiloxy) silylethyldimethicone.
  • the compound (s) of the formulas (I) and / or (II) are selected from the group of methylparaben, ethylparaben, cymenol, hydroxyacetophenone.
  • Cymenol, or o-cymene-5-ol, lUPAC name 3-methyl-4- (1-methylethyl) phenol has the CAS no. 3228-02-02 and is characterized by the following structure:
  • Ethyl paraben (p-hydroxybenzoic acid ethyl ester) has the CAS no. 120-47-8 and is characterized by the following structure:
  • Methylparaben (p-Hydroxybenzoeklaremethylester) has the CAS no. 99-76-3 and is characterized by the following structure:
  • 4-hydroxyacetophenone also called piceol
  • water-in-oil emulsions advantageously contain from 0.001 to 5.0% by weight, preferably from 0.01 to 3.0% by weight, particularly preferably from 0.1 to 1.0% by weight, based on the Total weight of the preparation, of benzoic acid and / or one or more compounds of the formula (I) and / or (II), in particular one or more compounds from the group of methylparaben, ethylparaben, cymenol, hydroxyacetophenone.
  • the preparations according to the invention are free-flowing but can also be formulated into creams, have very good cosmetic properties, in particular with regard to stickiness, and have very good skin compatibility and skin care performance.
  • the proportion of the oil phase of the preparations according to the invention in the range from 3 to 60% by weight, based on the total weight of the preparations.
  • 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, butylene glycol, monoethyl or monobutyl ether, diethylene glycol monomethyl or monoethyl ether and analogous products, foam stabilizers, electrolytes, 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, prop
  • Fats, waxes and other natural and synthetic fatty substances preferably esters of fatty acids with alcohols of low C number, for example with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids of low C number or with fatty acids; Alcohols, diols or polyols of low C number, and their ethers, preferably ethanol, isopropanol, 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 ,
  • the oil phase of the emulsions according to the present invention optionally consists in part of silicone oils.
  • silicone oils cyclic and / or linear silicones, which are also referred to as "silicone oils" within the scope of the present disclosure
  • silicones or silicone oils can be present as monomers, which are generally available through Structural elements are characterized as follows:
  • silicon atoms can be substituted with identical or different alkyl radicals and / or aryl radicals, which are here generalized by the radicals R1 -R4 (meaning that the number of different radicals is not necessarily limited to 4), m can thereby Assume values from 2 to 200,000. Dimethicone is advantageously chosen as silicone oil.
  • silicone oils for example cyclomethicone (octamethylcyclotetrasiloxane), phenyldimethicone, for example hexamethylcyclotrisiloxane, polydimethylsiloxane, poly (methylphenylsiloxane), cetyldimethicone, behenoxydimethicone, are to be used advantageously in the context of the present invention.
  • oil components of the oil phase of the preparations according to the invention wholly or largely completely from the group of oils of synthetic and / or natural origin.
  • These can then be advantageously selected from the group of esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids having a chain length of 3 to 30 carbon atoms and saturated and / or unsaturated, branched and / or unbranched alcohols having a chain length of 3 to 30 carbon atoms, from the group of esters of aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols having a chain length of 3 to 30 carbon atoms.
  • ester oils can then advantageously be selected from the group isopropyl myristate, isopropyl palmitate, isopropyl stearate, n-decyl oleate, isooctyl stearate, isononyl stearate, isononyl isononanoate, cetearyl isononanoate, isodecyl neopentanoate, 2-ethylhexyl palmitate, 2-ethylhexyl laurate, 2-hexyldecyl stearate, coco-caprylate / caprate, Olefin oleate, oleyl erucate, erucyl oleate, erucyl erucate and synthetic, semi-synthetic and natural mixtures of such esters, eg Jojoba oil.
  • the oil phase can be advantageously selected in part from the group of branched and unbranched hydrocarbons and waxes, the dialkyl ethers, the group of saturated or unsaturated, branched or unbranched alcohols, and the fatty acid triglycerides, in particular the triglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids of a chain length of 8 to 24, in particular 12 to 18 carbon atoms.
  • the fatty acid triglycerides can be advantageously selected from the group of synthetic, semi-synthetic and natural oils, e.g. Caprylic capric triglyceride, cocoglycerides, sunflower oil, soybean oil, almond oil and the like.
  • dimethicone and Cetearylisononanoate are also advantageous.
  • hydrocarbons paraffin oil, squalane, hydrogenated polyisobutene, isohexadecan, isododecane; Ci 5 -ig alkane or polydecene advantageous to use in the context of the present invention.
  • Formulations according to the present invention may also contain one or more additional non-silicone emulsifiers, for example advantageously selected from the group of the following substances, which as a rule act as W / O emulsifiers.
  • Emulsions according to the invention for the purposes of the present invention are advantageous and contain e.g. Fats, oils, waxes and / or other fats, as well as water and one or more emulators, as commonly used for such type of formulation.
  • compositions according to the present invention usually contain one or more drugs in effective concentration.
  • cosmetic or topical dermatological compositions according to the present invention depending on their structure, for example, be used as skin protection cream, cleansing milk, sunscreen lotion, nutrient cream, day or night cream, etc. It is possible and advantageous, the compositions of the invention as a basis for pharmaceutical To use formulations.
  • these preferably additionally contain at least one UVA filter substance and / or at least one UVB filter substance and / or at least one inorganic pigment.
  • UV-A or UV-B filter substances are usually incorporated in day creams.
  • preparations according to the invention may contain substances which absorb UV radiation in the UVB range, the total amount of filter substances being e.g. 0.1 wt .-% to 30 wt .-%, preferably 0.5 to 10 wt .-%, in particular 1 to 6 wt .-%, based on the total weight of the preparations.
  • the UVB filters may be oil-soluble or water-soluble.
  • oil-soluble substances are e.g. to call:
  • esters of cinnamic acid preferably 4-methoxycinnamic acid (2-ethylhexyl) ester
  • esters of salicylic acid preferably 2-ethylhexyl salicylate, 4-isopropylbenzyl salicylate,
  • benzophenone preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone;
  • 2-phenylbenzimidazole-5-sulfonic acid and its salts e.g. Sodium, potassium or triethanolammonium salts
  • Sulfonic acid derivatives of benzophenones preferably 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and its salts
  • Sulfonic acid derivatives of the 3-benzylidene camphor such as, for example, 4- (2-oxo-3-bomylidenemethyl) benzenesulfonic acid, 2-methyl-5- (2-oxo-3-bomylidenemethyl) sulfonic acid and its salts.
  • UVB filters which can be used according to the invention should of course not be limiting.
  • UVA filters in formulations according to the invention which are customarily contained in cosmetic and / or dermatological preparations.
  • Such filter substances are preferably derivatives of dibenzoylmethane, in particular 1 - (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1,3-dione and 1-phenyl-3-dione. (4'-isopropyl-phenyl) -propane-1,3-dione.
  • preparations containing these combinations are the subject of the invention. It is possible to use the same amounts of UVA filter substances which have been mentioned for UVB filter substances.
  • Cosmetic and / or dermatological preparations according to the present invention may also contain inorganic pigments which are commonly used in cosmetics to protect the skin from UV rays. These are oxides of titanium, zinc, iron, zirconium, silicon, manganese, aluminum, chromium, cerium and mixtures thereof, as well as modifications in which the oxides are the active agents. But also ultramarine blue and pearlescent pigments. Particular preference is given to pigments based on titanium dioxide. The amounts mentioned for the above combinations may be used.
  • the cosmetic and dermatological preparations according to the invention may contain cosmetic active substances, auxiliaries and / or additives such as are conventionally used in such preparations, for example antioxidants, preservatives, bactericides, perfumes, substances for preventing foaming, dyes, pigments, the coloring effect have, thickeners, surface-active substances, emulsifiers, softening, moistening and / or moisturizing substances, fats, oils, waxes or other conventional ingredients of a cosmetic or dermatological formulation such as alcohols, polyols, polymers, foam stabilizers, organic solvents or silicone derivatives.
  • cosmetic active substances for example antioxidants, preservatives, bactericides, perfumes, substances for preventing foaming, dyes, pigments, the coloring effect have, thickeners, surface-active substances, emulsifiers, softening, moistening and / or moisturizing substances, fats, oils, waxes or other conventional ingredients of a cosmetic or dermatological formulation such as alcohols, polyols,
  • both the W / Si emulsifier and the W / O emulsifier are added to the oil phase.
  • the components of the oil phase are mixed together with a magnetic stirrer to homogeneity of the phase, optionally heating something.
  • the sodium chloride and the respective aromatics are dissolved in the water phase.
  • the water phase may be heated slightly to dissolve the raw material. Then the water phase is slowly added with stirring to the oil phase and then thoroughly mixed with a high-speed mixer (eg a magic stick ESGE) for about 2 minutes.
  • a high-speed mixer eg a magic stick ESGE
  • the stability was visually evaluated after 7 days, 14 days, 21 days (T) and 1 month (M).

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Dispersion Chemistry (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne des émulsions eau dans l'huile cosmétiques ou dermatologiques contenant A) des cétyl-diglycéryl-tris-(triméthyl­siloxy)-silyléthyldiméthicones comme émulsifiant, B) une phase huileuse et C) une phase aqueuse, caractérisées en ce qu'elles contiennent de l'acide benzoïque et/ou une ou plusieurs substances de formule (I) et/ou de formule (II) présentant la structure générique suivante : formule (I), dans laquelle X peut représenter une chaîne alkyle en C1–C4 ramifiée ou non ramifiée, un groupe hydroxy ou un groupe O, et la liaison en pointillé représente une double liaison lorsque X représente un groupe O, et R peut représenter indépendamment de X une chaîne alkyle en C1–C4 ramifiée ou non ramifiée, une chaîne alkyle en C1–C4 ramifiée ou non ramifiée pontée par un atome d'oxygène, ou un groupe hydroxy. Formule (II)
EP18729357.6A 2017-07-24 2018-05-24 Émulsions eau dans l'huile contenant des cétyl-diglycéryl-tris-(triméthylsiloxy)silyléthyldiméthicones comme émulsifiant et contenant des composés aromatiques Withdrawn EP3658104A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102017212625.6A DE102017212625A1 (de) 2017-07-24 2017-07-24 Wasser-in-Öl-Emulsionen auf der Grundlage von Cetyl Diglyceryl Tris(Trimethyl­siloxy)­silylethyldimethicone als Emulgator, welche einen Gehalt an Aromaten aufweisen
PCT/EP2018/063647 WO2019020241A1 (fr) 2017-07-24 2018-05-24 Émulsions eau dans l'huile contenant des cétyl-diglycéryl-tris-(triméthylsiloxy)silyléthyldiméthicones comme émulsifiant et contenant des composés aromatiques

Publications (1)

Publication Number Publication Date
EP3658104A1 true EP3658104A1 (fr) 2020-06-03

Family

ID=62530192

Family Applications (1)

Application Number Title Priority Date Filing Date
EP18729357.6A Withdrawn EP3658104A1 (fr) 2017-07-24 2018-05-24 Émulsions eau dans l'huile contenant des cétyl-diglycéryl-tris-(triméthylsiloxy)silyléthyldiméthicones comme émulsifiant et contenant des composés aromatiques

Country Status (4)

Country Link
EP (1) EP3658104A1 (fr)
CN (1) CN110944619A (fr)
DE (1) DE102017212625A1 (fr)
WO (1) WO2019020241A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020227908A1 (fr) * 2019-05-14 2020-11-19 Beiersdorf Daily Chemical (Wuhan) Co. Ltd. Émulsion eau/huile à rupture rapide exempte de cyclométhicones

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10207270A1 (de) * 2002-02-21 2003-09-11 Beiersdorf Ag Tensidhaltige Wasser-in Öl-Emulsion bei hohem Wasseranteil
JP6105920B2 (ja) * 2011-12-27 2017-03-29 東レ・ダウコーニング株式会社 共変性オルガノポリシロキサン、それを含有してなる油中水型エマルション用乳化剤、外用剤および化粧料
JP6313540B2 (ja) * 2011-12-27 2018-04-18 東レ・ダウコーニング株式会社 ジグリセリン誘導体変性シリコーン、それを含有してなる油中水型エマルション用乳化剤、外用剤および化粧料
CN118078649A (zh) * 2015-09-03 2024-05-28 塔格拉生物技术有限公司 微胶囊及其制备方法与包含多个微胶囊的非化妆品组合物
DE102016201763A1 (de) * 2016-02-05 2017-08-10 Beiersdorf Ag Wasser-in-Öl-Emulsionen auf der Grundlage von Cetyl Diglyceryl Tris(Trimethyl-siloxy)-silylethyldimethicone als Emulgator, welche weitgehend frei sind von Silikonölen

Also Published As

Publication number Publication date
DE102017212625A1 (de) 2019-01-24
WO2019020241A1 (fr) 2019-01-31
CN110944619A (zh) 2020-03-31

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