US20120136067A1 - Oil/water active ingredient emulsion containing uv filter - Google Patents

Oil/water active ingredient emulsion containing uv filter Download PDF

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Publication number
US20120136067A1
US20120136067A1 US13/119,036 US200913119036A US2012136067A1 US 20120136067 A1 US20120136067 A1 US 20120136067A1 US 200913119036 A US200913119036 A US 200913119036A US 2012136067 A1 US2012136067 A1 US 2012136067A1
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US
United States
Prior art keywords
emulsion
ethylhexyl
inci
triazine
ester
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.)
Abandoned
Application number
US13/119,036
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English (en)
Inventor
Stephan Ruppert
Claudia Steikert
Alexandra Blohm
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
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Application filed by Beiersdorf AG filed Critical Beiersdorf AG
Assigned to BEIERSDORF AG reassignment BEIERSDORF AG ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: RUPPERT, STEPHAN, STEIKERT, CLAUDIA, BLOHM, ALEXANDRA
Publication of US20120136067A1 publication Critical patent/US20120136067A1/en
Abandoned legal-status Critical Current

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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
    • A61K8/04Dispersions; Emulsions
    • A61K8/06Emulsions
    • A61K8/062Oil-in-water emulsions
    • 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
    • A61K8/04Dispersions; Emulsions
    • A61K8/06Emulsions
    • 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
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35Ketones, e.g. benzophenone
    • 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
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • 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
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4966Triazines or their condensed derivatives
    • 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
    • A61K8/96Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783Angiosperms [Magnoliophyta]
    • A61K8/9789Magnoliopsida [dicotyledons]
    • 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
    • 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
    • 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
    • A61K2800/59Mixtures
    • A61K2800/592Mixtures of compounds complementing their respective functions

Definitions

  • the present invention relates to a cosmetic O/W emulsion comprising
  • the skin is the largest organ belonging to humans. It has a large number of vital functions to fulfill, for example the regulation of heat and the barrier function against drying out of the skin and of the entire organism, and as protective equipment against the penetration and absorption of external substances.
  • This barrier function is effected through the epidermis, which as the outermost layer forms the actual protective covering against environmental conditions. With about one tenth of the total thickness, at the same time, it is the thinnest layer of the skin.
  • the skin is exposed to a large number of physical, chemical and biological stresses. A large number of these stresses lead to temporary or permanent reddening of the skin for various reasons.
  • the skin can fulfill its biological functions, it requires regular cleansing and care.
  • active ingredients are as a rule added to cosmetic skin care products.
  • the active ingredients employed in skin care include, for example, licorice extracts.
  • the key active ingredient of licorice extract, in particular of Glycyrrhiza inflata, in this context is the compound licochalcone A, which has the following structure:
  • Licorice extracts containing licochalcone A are employed in this context in particular to protect against skin irritations, such as reddenings.
  • a disadvantage of the prior art of cosmetic formulations containing licorice extracts is, however, the fact that the extracts and in particular licochalcone A are not particularly storage-stable. If these formulations are stored for a relatively long period of time, and in particular at higher temperatures, degradation of the active ingredient(s) in the formulation occurs and the cosmetic slowly loses effectiveness. This loss in effectiveness occurs to a particularly high degree in O/W emulsions (oil-in-water emulsions).
  • the object is achieved in particular by the use of a UV filter combination of
  • the invention relates in this context in particular to the process for the preparation of an O/W emulsion containing licochalcone A and/or licorice extract, characterized in that
  • the licorice extract which is preferred according to the invention originates from the plant Glycyrrhiza inflata.
  • the extract is present in the form of an aqueous extract in which
  • the cosmetic O/W emulsion according to the invention it is advantageous if the cosmetic O/W emulsion according to the invention, the use according to the invention or the process according to the invention is characterized in that the formulation or UV filter combination contains as a further constituent 2,4-bis- ⁇ [4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl ⁇ -6-(4-methoxyphenyl)-1,3,5-triazine (INCI: aniso triazine).
  • the formulation or UV filter combination contains as a further constituent 2,4-bis- ⁇ [4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl ⁇ -6-(4-methoxyphenyl)-1,3,5-triazine (INCI: aniso triazine).
  • Embodiments of the present invention which are advantageous according to the invention, characterized in that the formulation contains at least 2.1 wt.%, based on the total weight of the formulation, of 4-(tert-butyl)-4′-methoxydibenzoylmethane.
  • 2,4-Bis- ⁇ [4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl ⁇ -6-(4-methoxyphenyl)-1,3,5-triazine is advantageously employed according to the invention in a concentration of 0.1 from to 5% by weight, based on the total weight of the formulation.
  • the formulation contains one or more UV filters chosen from the group of the compounds phenylene-1,4-bis-(2-benzimidazyl)-3,3′-5,5′-tetrasulfonic acid salts; 2-phenylbenzimidazole-5-sulfonic acid salts; 1,4-di(2-oxo-10-sulfo-3-bornylidenemethyl)-benzene and salts thereof; 4-(2-oxo-3-bornylidenemethyl)benzenesulfonic 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-642-methyl-3-[1,3,3,3-tetramethyl-1-[
  • the formulation according to the invention is free from p-methylbenzylidenecamphor.
  • the formulation according to the invention contains ethanol.
  • the formulation according to the invention can moreover advantageously contain one or more further compounds with an alcohol function, for example glycerol, 2-methyl-1,3-propanediol, pentane-1,2-diol, hexane-1,2-diol, heptane-1,2-diol, octane-1,2-diol, nonane-1,2-diol, decane-1,2-diol, propanols, propane- and butanediols.
  • an alcohol function for example glycerol, 2-methyl-1,3-propanediol, pentane-1,2-diol, hexane-1,2-diol, heptane-1,2-diol, octane-1,2-diol, nonane-1,2-diol, decane-1,2-diol, propanols
  • the formulation according to the invention contains one or more antioxidants.
  • the formulation contains one or more compounds chosen from the group of the compounds tocopherol, tocopherol acetate, 2,6-di-tert-butyl-4-methylphenol.
  • the formulation according to the invention can moreover contain one or more further active ingredients, for example alpha-lipoic acid, folic acid, phytoene, D-biotin, coenzyme Q10, alpha-glucosylrutin, carnitine, carnosine, natural and/or synthetic isoflavonoids, flavonoids, creatine, creatinine, taurine, (3-alanine, tocopheryl acetate, dihydroxyacetone, 8-hexadecene-1,16-dicarboxylic acid, glycerylglycose, (2-hydroxyethyl)urea, niacinamide, vitamin A or its derivatives.
  • active ingredients for example alpha-lipoic acid, folic acid, phytoene, D-biotin, coenzyme Q10, alpha-glucosylrutin, carnitine, carnosine, natural and/or synthetic isoflavonoids, flavonoids, creatine, creatinine, taurine, (3-alanine, tocop
  • the formulation contains one or more polymers.
  • Embodiments which are preferred according to the invention are characterized in that the formulation contains one or more polymers chosen from the group of the compounds acrylate/C10-C30 alkyl acrylate cross polymer, acrylates, carbomers, tapioca starch, xanthan gum.
  • the oily phase of the O/W emulsion contains one or more oil components chosen from the group of the compounds butylene glycol dicaprylate/dicaprate, myristyl myristate, octyldodecanol, C12-15 alkyl benzoate caprylic/capric triglyceride, diisopropyl sebacate, dicaprylyl ether, mineral oil, silicone oil.
  • the formulation according to the invention contains one or more preservatives, in particular one or more parabens and/or phenoxyethanol.
  • the O/W emulsion according to the invention can moreover contain further cosmetic active ingredients, auxiliary substances and additives, for example EDTA and perfume substances, such as limonene, linalool, benzyl benzoate, hydroxyisohexyl 3-cyclohexene, carboxaldehyde, hexyl cinnamal, benzyl salicylate, eugenol, butylphenyl methylpropional, alpha-isomethyl ionone, citronellol, coumarin, geraniol, cinnamyl alcohol, citral.
  • EDTA EDTA and perfume substances
  • perfume substances such as limonene, linalool, benzyl benzoate, hydroxyisohexyl 3-cyclohexene, carboxaldehyde, hexyl cinnamal, benzyl salicylate, eugenol, butylphenyl methylprop
  • Sensorial additives can furthermore in the emulsion, such as distarch phosphate, sodium starch octenylsuccinate, aluminum starch octenylsuccinate, acrylonitrile/methacrylonitrile/methyl methacrylate copolymer+isopentane+magnesium hydroxide, tapioca starch, silica, nylon 6 polyamide 5, micronized talk.
  • distarch phosphate sodium starch octenylsuccinate, aluminum starch octenylsuccinate, acrylonitrile/methacrylonitrile/methyl methacrylate copolymer+isopentane+magnesium hydroxide, tapioca starch, silica, nylon 6 polyamide 5, micronized talk.
  • the hot aqueous phase advantageously has a temperature of from 50 to 95° C., preferably a temperature of from 75 to 90° C. and particularly preferably a temperature of about 85° C.
  • a temperature of from 50 to 95° C. preferably a temperature of from 75 to 90° C. and particularly preferably a temperature of about 85° C.
  • the term “about” in this context is intended solely to characterize the slight temperature variations typical of such processes.
  • the heated oily phase advantageously has a temperature of from 50 to 95° C., preferably a temperature of from 75 to 90° C. and particularly preferably a temperature of about 85° C.
  • the term “about” in this context is intended solely to characterize the slight temperature variations typical of such processes.
  • Mixers from Becomix or Krieger are advantageously used according to the invention as homogenizers.
  • the homogenization is advantageously carried out over a period of time of from 2 to 25 minutes.
  • the stirring speed during the homogenization is advantageously from 500 to 2,000 rpm, a stirring speed of from 1,000 to 1,400 rpm being preferred according to the invention, and a stirring speed of 1,200 rpm (+ ⁇ 50 rpm) being particularly preferred according to the invention.
  • the formulation is advantageously cooled to a temperature of from 25 to 40° C., a temperature of about 35° C. being preferred.
  • a temperature of about 35° C. being preferred.
  • the perfume substances and preservatives are preferably mixed with one another before the addition to the emulsion.
  • the perfume substances and preservatives are preferably dissolved in ethanol before the addition to the emulsion.
  • the formulations can serve for care of the skin, cosmetic protection from light or as a make-up product in decorative cosmetics.
  • cosmetic compositions in the context of the present invention can be used, for example, as skin protection cream, day or night cream etc. It may be possible and advantageous to use the compositions according to the invention as a base for pharmaceutical formulations.
  • the formulation according to the invention is used in particular for protection from ageing of the skin (in particular for protection from ageing of the skin of UV origin) and as a sunscreen composition.
  • the formulation according to the invention advantageously has a pH of from 5 to 8. This can be established by conventional acids, bases and buffer systems.
  • Recipe sample 1 contains a preparation without the stabilizers butyl methoxydibenzoyl methane and octocrylene. Recipe sample 2 additionally contains the two stabilizers.
  • Sample 1 Sample 2 INCI name(s) m [%] m [%] Alcohol denat. 6.00 6.00 Sodium hydroxide 0.60 0.60 Cetearyl alcohol + PEG-40 castor oil + 2.00 2.00 sodium cetearyl sulfate Glyceryl stearate SE 0.80 0.80 Trisodium EDTA 1.00 1.00 Methylparaben 0.30 0.30 Phenoxyethanol 0.20 0.20 Bis-ethylhexyloxyphenol methoxyphenol triazine 3.50 3.50 Butyl methoxydibenzoyl methane 4.50 Diethylhexyl butamido triazone 1.00 1.00 Ethylhexyl methoxycinnamate + BHT 2.00 2.00 Octocrylene 4.50 Phenylbenzimidazole sulfonic acid 2.00 2.00 Glycerin 2.00 2.00 Butylene glycol dicaprylate/dicaprate 7.00 7.00 C12-15 alkyl benzoate 11.00 11.00 My
  • the licorice content was determined by means of HPLC-DAD via an external calibration series.
  • the licorice provided by the client was employed for the calibration, NART: 96146-90000-00, batch 17743901.
  • the contents stated in the report are based on the reference substance employed for the calibration.
  • the specimen sample 2 contains more licorice extract (licochalcone A) than the specimen sample 1.
  • the addition of the stabilizers butyl methoxydibenzoyl methane and octocrylene leads to an increased heat and storage stability of the licorice extract (licochalcone A).

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Dermatology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Emergency Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Botany (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Cosmetics (AREA)
US13/119,036 2008-09-16 2009-09-11 Oil/water active ingredient emulsion containing uv filter Abandoned US20120136067A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE102008048328.1 2008-09-16
DE102008048328A DE102008048328A1 (de) 2008-09-16 2008-09-16 UV-Filter haltige O/W-Wirkstoffemulsion
PCT/EP2009/006608 WO2010031522A1 (fr) 2008-09-16 2009-09-11 Émulsion de substance active huile dans eau contenant un filtre uv

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2009/006608 A-371-Of-International WO2010031522A1 (fr) 2008-09-16 2009-09-11 Émulsion de substance active huile dans eau contenant un filtre uv

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US15/359,841 Division US10603256B2 (en) 2008-09-16 2016-11-23 Oil/water active ingredient emulsion containing UV filter

Publications (1)

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US20120136067A1 true US20120136067A1 (en) 2012-05-31

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Family Applications (2)

Application Number Title Priority Date Filing Date
US13/119,036 Abandoned US20120136067A1 (en) 2008-09-16 2009-09-11 Oil/water active ingredient emulsion containing uv filter
US15/359,841 Expired - Fee Related US10603256B2 (en) 2008-09-16 2016-11-23 Oil/water active ingredient emulsion containing UV filter

Family Applications After (1)

Application Number Title Priority Date Filing Date
US15/359,841 Expired - Fee Related US10603256B2 (en) 2008-09-16 2016-11-23 Oil/water active ingredient emulsion containing UV filter

Country Status (5)

Country Link
US (2) US20120136067A1 (fr)
EP (2) EP2337545B1 (fr)
DE (1) DE102008048328A1 (fr)
ES (2) ES2430257T5 (fr)
WO (1) WO2010031522A1 (fr)

Cited By (2)

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KR20170038262A (ko) * 2015-09-30 2017-04-07 (주)아모레퍼시픽 수중유형 에멀젼 조성물
WO2020025257A1 (fr) 2018-07-30 2020-02-06 Unilever N.V. Compositions comprenant des ingrédients botaniques actifs

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CN110015691B (zh) * 2019-05-27 2021-10-01 山东师范大学 一种制备纳米级钼酸钡颗粒的方法
BR112022020348A2 (pt) * 2020-04-08 2022-11-22 Beiersdorf Ag Composição antipoluição
DE102020210312A1 (de) * 2020-08-13 2022-02-17 Beiersdorf Aktiengesellschaft Kosmetische Ethanol-in-Öl-Emulsion
CN113827495B (zh) * 2021-11-17 2023-10-20 青海倍力甘草科技发展有限责任公司 一种防晒剂及其制备方法以及应用

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US20170071832A1 (en) 2017-03-16
EP2337545B1 (fr) 2012-08-15
EP2471501B1 (fr) 2013-08-28
WO2010031522A1 (fr) 2010-03-25
EP2337545A1 (fr) 2011-06-29
EP2471501B2 (fr) 2021-11-17
DE102008048328A1 (de) 2010-04-15
US10603256B2 (en) 2020-03-31
ES2392386T3 (es) 2012-12-10
EP2471501A1 (fr) 2012-07-04
ES2430257T3 (es) 2013-11-19

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