EP0725619A1 - Procede de realisation d'emulsions huile dans eau - Google Patents

Procede de realisation d'emulsions huile dans eau

Info

Publication number
EP0725619A1
EP0725619A1 EP94930201A EP94930201A EP0725619A1 EP 0725619 A1 EP0725619 A1 EP 0725619A1 EP 94930201 A EP94930201 A EP 94930201A EP 94930201 A EP94930201 A EP 94930201A EP 0725619 A1 EP0725619 A1 EP 0725619A1
Authority
EP
European Patent Office
Prior art keywords
oil
temperature
weight
emulsion
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Withdrawn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
EP94930201A
Other languages
German (de)
English (en)
Inventor
Thomas Förster
Marcus Claas
Axel KÜHN
Rolf Wachter
Armin Wadle
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0725619A1 publication Critical patent/EP0725619A1/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Withdrawn legal-status Critical Current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
    • A61K8/062—Oil-in-water 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
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86—Polyethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • 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
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/21—Emulsions characterized by droplet sizes below 1 micron

Definitions

  • the invention relates to a process for the preparation of oil-in-water emulsions containing special organic cosmetic active ingredients under conditions which lead to finely dispersed and long-term stable emulsions.
  • phase inversion means that the outer, aqueous phase becomes the inner phase at higher temperatures. This process is generally reversible, which means that the original type of emulsion is formed again on cooling. It is also known that the location of the phase inversion temperature depends on many factors, for example the type and phase volume of the oil component, the hydrophilicity and the structure of the emulsifier or the composition of the emulsifier system, compare, for example, K. Shinoda and H. Kunieda in Encyclopedia of Emulsion Technology, Volume I, P.
  • DE-A-38 19 193 discloses a process for producing low-viscosity O / W emulsions using phase inversion technology. This technique is applied to mixtures containing oil bodies, a nonionic emulsifier and a coemulsifier in an aqueous medium.
  • DE-A-41 40 562 discloses a process for producing O / W emulsions with particularly polar oil bodies by means of phase inversion technology.
  • Particularly polar oil bodies are understood to mean oils with a dipole moment above 1.96 D.
  • the technique of phase inversion is applied to mixtures containing the above-mentioned particularly polar oils, a nonionic emulsifier, possibly a coemulsifier, and an interface moderator, which is from the group of tocopherols, Guerbet alcohols with 16 to 20 carbon atoms or a steroid with 1 to 3 OH groups is selected.
  • the object of the present invention was to develop a process for the production of finely dispersed and long-term stable O / W emulsions containing an organic cosmetic active ingredient.
  • a method should be provided which is an active ingredient from the group of deodorant ingredients, perfume oils and sun protection factors.
  • O / W emulsions containing an organic cosmetic active ingredient are particularly finely divided and long-term stable if a mixture of oil, nonionic emulsifier and an organic cosmetic active ingredient is selected from the group the deodorants, perfume oils and light protection factors, heated within or above the phase inversion temperature range - or the emulsion is produced at this temperature - and then cools the emulsion to a temperature below the phase inversion temperature range and optionally further diluted with water.
  • the additional condition applies that the amount of the organic cosmetic active ingredient is 5 to 100% by weight of the amount of the oil.
  • the invention therefore relates to a process for the preparation of oil-in-water emulsions containing an organic cosmetic active ingredient, wherein
  • the process according to the invention has the advantage that particularly fine-particle emulsions are obtained which have excellent storage stability. Compared to the known prior art, e.g. B. DE-OS-38 19 193, the phase inversion temperature is also reduced, which is particularly beneficial in practice because of the associated energy savings. A further advantage is that the emulsions prepared by the process according to the invention are of low viscosity.
  • Suitable oil bodies (A) are both polar oil components with one or more ester groups in the molecule, but also mixtures of such polar oil components with smaller amounts of nonpolar hydrocarbons.
  • Particularly suitable polar oil components are mono- and diesters of the general formulas (I), (II) and (III)
  • R * is an alkyl group with 8 to 22 C atoms and R 2 is an alkyl group with 3 to 22 C atoms and R 3 is alkylene groups with 2 to 16 C atoms, with the proviso that the total number of C atoms in the compounds (I) to (III) is at least 11.
  • Oil bodies of the type of the mono- and diesters of the formulas (I), (II) and (III) are known as cosmetic and pharmaceutical oil components and as lubricants and lubricants.
  • the products that are liquid at room temperature (20 ° C) are of the greatest importance.
  • Monoesters (I) suitable as oil bodies are, for example, the isopropyl esters of fatty acids having 12 to 22 carbon atoms, such as, for example, isopropyl myristate, isopropyl palmitate, isopropyl stearate and isopropyl oleate.
  • Suitable monoesters are, for example, n-butyl stearate, n-hexyl laurate, n-decyl oleate, isoctyl stearate, isononyl palmitate, isononyl isononanoate, 2-ethylhexyl palmitate, 2-ethylhexyl laurate, 2-hexyl decyl stearate Octyldodecyl palmitate, oleyl oleate, olerlerucate, erucyl oleate and esters which are obtainable from technical aliphatic alcohol mixtures and technical aliphatic carboxylic acids, for example esters from saturated and unsaturated fatty alcohols with 12 to 22 carbon atoms and saturated and unsaturated fatty acids with 12 up to 22 carbon atoms, as they are accessible from animal and vegetable fats.
  • Naturally occurring monoester or wax ester mixtures such as those present in jojoba oil or
  • Suitable dicarboxylic acid esters (II) are e.g. Di-n-butyl adipate, di-n-butyl sebacate, di- (2-ethylhexyl) adipate, di- (2-hexyldecyl) succinate and di-isotridecylfugate.
  • Suitable diol esters (III) are e.g.
  • Esters of trihydric and polyhydric alcohols in particular vegetable triglycerides, e.g. Olive oil, almond oil, peanut oil, sunflower oil or the esters of pentaerythritol with e.g. Pelargonic acid or oleic acid.
  • vegetable triglycerides e.g. Olive oil, almond oil, peanut oil, sunflower oil or the esters of pentaerythritol with e.g. Pelargonic acid or oleic acid.
  • fatty acid triglycerides natural, vegetable oils, e.g. B. olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palm oil, but also the liquid proportions of coconut oil or palm kernel oil as well as mineral oils, such as. B. claw oil, the liquid portions of beef tallow or synthetic triglycerides, such as those obtained by esterifying glycerol with fatty acids containing 8 - 22 carbon atoms, e.g. B. Trigly- cerides from caprylic acid-capric acid mixtures, triglycerides from technical oleic acid or from palmitic acid-oleic acid mixtures are used.
  • natural, vegetable oils e.g. B. olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palm oil, but also the liquid proportions of coconut oil or palm kernel oil as well as mineral oils, such as. B. claw oil, the liquid portions of beef tallow or synthetic triglycerides
  • Such mono- and diesters and triglycerides are preferably suitable as oil components for the process according to the invention which are liquid at normal temperature of 20 ° C., but higher-melting fats and esters which correspond to the formulas given can also be used in such amounts be that the mixture of the oil components remains liquid at normal temperature.
  • the oil component can also contain hydrocarbon oils in minor amounts up to a maximum of 25% by weight, based on the oil component.
  • Suitable hydrocarbons are primarily paraffin oils and synthetically produced hydrocarbons, e.g. B. liquid polyolefins or defined hydrocarbons, for. B. alkylcyclohexanes such. B. the 1,3-di-isooctyl-cyclohexane.
  • Substances suitable as nonionic emulsifiers (B) are characterized by a lipophilic, preferably linear alkyl or acyl group and a hydrophilic group formed from low molecular weight glycol, glucose and polyol ethers.
  • the nonionic emulsifiers (B) are used in the O / W emulsions according to the invention in an amount of 0.5 to 30 parts by weight, preferably 3 to 20 parts by weight.
  • Particularly suitable nonionic emulsifiers (B) are ethylene oxide addition products onto fatty alcohols with 16 to 22 carbon atoms. Such products are commercially available.
  • the technical products are mixtures of homologous polyglycol ethers of the starting fatty alcohols, the average degree of ethylation of which corresponds to the molar amount of ethylene oxide added.
  • emulsifiers it is also possible to use ethylene oxide addition products on partial esters of a polyol having 3 to 6 carbon atoms and fatty acids having 14 to 22 carbon atoms.
  • Products of this type are produced, for example, by ethoxylating fatty acid partial glycerides or mono- and D-fatty acid esters of sorbitan, for example sorbitan monostearate or sorbitan sesquioleate.
  • the emulsifiers suitable for the process according to the invention should have an HLB value of 10 to 18.
  • the HLB value hydrophile-lipophile balance
  • L is the weight fraction of the lipophilic groups, i.e. H. the percentage of fatty alkyl or fatty acyl groups in the ethylene oxide adducts.
  • Preferred emulsifiers (B) are fatty alcohol polyglycol ethers (B1) of the general formula (IV)
  • R 4 is a saturated or unsaturated, straight-chain or branched hydrocarbon radical having 8 to 22 carbon atoms, preferably 12 to 22 carbon atoms and n an integer from 10 to 50, preferably from 10 to 30, and addition products from 4 to 20 moles of ethylene oxide to one or more fatty acid partial glycerides (B2).
  • Fatty acid partial glycerides (B2) of saturated or unsaturated fatty acids with 10 to 20 C atoms are technical mixtures of fatty acid mono-, di- and triglycerides which are esterified by 1 mole of glycerol with 1 to 2 moles of a (C ⁇ o- 2 ⁇ ) ⁇ ** rettTexre ° d it by transesterification tion of 1 mole of a (C ⁇ o_2 ⁇ ) "frettklaretr ⁇ 9LY cer '' d s ⁇ Z * B - from beef tallow, lard, palm oil, sunflower oil or soybean oil with 0.5 to 2 moles
  • Two types of partial glycerides are commercially available.
  • Partial glycerides of type I contain 35 to 60% monoglycerides, 35 to 50% diglycerides and 1 to 20% triglycerides. Partial glycerides of type II are obtained from those of type I by molecular distillation manufactures and contains 90 to 96% monoglycerides, 1 to 5% diglycerides and less than 1% triglycerides (see also: a) G. Schuster and W. Adams: Zeitschrift für Strukturtechnologie, 1979, volume 30 (6), p . 256-264; b) G. Schust r (ed.) "Emulsifiers for Food", Springer-Verlag, 1985). The fatty acid partial glycerides used according to the invention should contain 35 to 96% monoglycerides, 1 to 50% diglycerides and 0.1 to 20% triglycerides.
  • Addition products of 8 to 12 mol ethylene oxide onto saturated fatty alcohols having 16 to 22 carbon atoms are particularly suitable as emulsifiers.
  • emulsifiers are, in particular, adducts of 8 to 12 moles of ethylene oxide with a saturated fatty alcohol having 18 to 22 carbon atoms.
  • a co-emulsifier can be useful in many cases for the preparation of the oil-in-water emulsions by the process according to the invention.
  • coe ulgators according to the invention are those of the type of fatty alcohols with 16 to 22 carbon atoms, for. B. cetyl alcohol, stearyl alcohol, arachidyl alcohol or behenyl alcohol or mixtures of these alcohols, as they are obtained in the technical hydrogenation of vegetable and animal fatty acids with 16 to 22 carbon atoms or the corresponding fatty acid methyl ester.
  • partial esters made of a polyol with 3 to 6 carbon atoms and fatty acids with 14 to 22 carbon atoms.
  • Such partial esters are e.g. B. the monoglycerides of palmitic and / or stearic acid, the sorbitan mono- and / or diesters of myristic acid, palmitic acid, stearic acid or mixtures of these fatty acids, the monoesters of triethylolpropane, erythritol or pentaerythritol and saturated fatty acids with 14 to 22 carbon atoms.
  • the technical monoesters which are obtained by esterification of 1 mol of polyol with 1 mol of fatty acid and which are a mixture of monoesters, diesters and unesterified polyol are also understood as monoesters.
  • Cetyl alcohol, stearyl alcohol or a glycerol, sorbitan or trimethylolpropane monoester of a fatty acid with 14 to 22 carbon atoms or mixtures of these substances are particularly suitable as co-emulsifiers for the process according to the invention.
  • the co-emulsifiers (C) are used in the O / W emulsions according to the invention in an amount of 0 or 0.1 to 30% by weight. The range from 2 to 20% by weight is preferred.
  • the organic cosmetic ingredient (D) is selected from the group of deodorant ingredients, perfume oils and sun protection factors.
  • Perfume oils are understood to mean substances with odor-active properties, as is customary in the technical field. This can e.g. be natural fragrances, such as those obtained from plants by distillation, extraction or pressing, or synthetically produced fragrances.
  • Deodorants are substances that prevent or largely suppress bacterial growth and / or odor formation.
  • Light protection factors are to be understood as organic substances which are able to absorb ultraviolet rays and which absorb energy in the form of longer-wave radiation, e.g. B. heat to release again (see, for example, perfumery and cosmetics, 1993 (74), pp. 485-490).
  • a particular advantage of the process according to the invention is that, regardless of whether they are water or oil-soluble, the active compounds (D) are equally emulsifiable and the dispersions obtained in this way are finely divided and storage-grade.
  • the condition for components (A) and (D) is that i) the sum of components (A) and (D) is 10 to 90% by weight, based on the mixture as a whole, and ii) that The proportion of component (D) in the range from 5 to 100% by weight, based on the oil body (A), is.
  • the sum of components (A) and (D) is 20 to 60% by weight.
  • components (A) to (D) can also be contained in the emulsion.
  • interface moderators from the group of the tocopherols, Guerbet alcohols with 16 to 20 C atoms and the steroids with 1 to 3 OH groups, which - in According to the teaching of DE-A-41 40 562 - then advantageously be selected as further components if the oil body (A) is an oil with a particularly high dipole moment.
  • Tocopherols are natural substances with a vitamin E character which are derived from 2-methyl-2- (4 '.8'. ⁇ '- trimethyltridecylj-chroman-e-ol, the so-called tocol.
  • the labeling is done with Greek Letters (see "Rö pps Chemie-Lexikon", O.-A.Neumüller (ed.), 7th ed., Stuttgart 1977, p. 3615f).
  • Particularly preferred is ⁇ -tocopherol, the most common and technically most important Tocopherol, which is often referred to as the actual vitamin E.
  • Guerbet alcohols are to be understood as special branched alcohols (see, for example, AJ O'Lenick Jr., RE Bilbo, Soap Cosm. Chem. Spec. 1987 (4) 52)
  • the Guerbet alcohols to be used according to the invention should have 16 to 20 carbon atoms, such as 2-hexyldecanol or 2-0ctyldodecanol, 2-0ctyldodecanol being particularly suitable, steroids being understood to mean a group of naturally occurring or synthetically obtained compounds , which the framework of the (partially) hydrogenated n Cyclopenta [a] phenanthrens is the basis, see e.g. O.A.
  • the steroids should have 1 to 3 OH groups.
  • the sterols in which an OH group is located on the third carbon atom of the steroid structure are particularly suitable.
  • the sterols occur in all animal and plant cells. After their occurrence, they are divided into zoosterols, e.g. Cholesterol and phytosterols, which are predominantly found in higher plants.
  • a particularly suitable steroid is cholesterol.
  • the process according to the invention can be carried out by first determining the phase inversion temperature by heating a sample of the emulsion prepared in the customary manner using a conductivity meter and determining the temperature at which the conductivity decreases sharply.
  • the decrease in the specific conductivity of the oil-in-water emulsion initially present usually decreases over a temperature interval of 5 to 15 ° C. from initially approximately 50 microsiemens per cm to values below approximately 5 microsiemens per cm.
  • the corresponding The temperature range is referred to as the phase inversion temperature range (PIT range).
  • the process according to the invention can either be carried out by subsequently heating the emulsion initially prepared in the customary manner to a temperature which is within or above the phase inversion temperature range, or in that By choosing a temperature that is within or above the phase inversion temperature range already during the preparation of the emulsion. It is also possible to dilute an anhydrous or low-water concentrate with hot or cold water at the phase inversion temperature (hot-hot or hot-cold method).
  • the process according to the invention can be carried out in the manner just described, the total amount of active substances (D) being used. However, it is also possible to proceed in the manner described, initially using only the oil-soluble active ingredients (D), while the water-soluble active ingredients (D) are only added subsequently to the oil-in-water emulsions obtained in this way . It follows from this that the advantages of the process according to the invention are particularly evident in the production of oil-in-water emulsions containing oil-soluble active ingredients (D).
  • Oil-in-water emulsions such as those obtained by the process according to the invention, are used in cosmetics, for example. B. as skin and body care products.
  • the method according to the invention is particularly preferably suitable for producing emulsion-like preparations for skin and hair treatment.
  • IPM isopropyl myristate
  • Ocylether di-n-octylether
  • Paraffin paraffin, viscous (type DAB 9, from Wasserbow / Bonn)
  • nonionic emulsifiers B
  • Eumul ⁇ in adduct of 12 moles of ethylene oxide with 1 mole of cetostearyl alcohol
  • CTFA name Ceteareth-12 ("Eumulgin Bl"; Fa. Henkel / Dusseldorf))
  • GMS glycerol monostearate
  • Cutina GMS Fa. Henkel / Düsseldorf
  • organic cosmetic active ingredients D
  • W-2 perfume oil (type "HC-50-2457”; Fa. Henkel / Düsseldorf)
  • Components (A) to (D) were mixed and heated to a temperature slightly above the melting point of the mixture and homogenized. Then the water, which was heated to about the same temperature, was emulsified into the melt with stirring.
  • the composition of the emulsions is shown in Table 1. The data are to be understood in% by weight, based on the mixture as a whole.
  • the emulsions were, as in 2.1. prepared and then briefly (about 1 minute) heated to 95 ° C. The emulsions were then cooled rapidly, ie at a cooling rate of about 2 ° C. per minute, to room temperature with stirring. 2.3- Determination of the phase inversion temperature
  • the electrical conductivity of the emulsions was determined as a function of the temperature using a conductivity measuring bridge (from Radiometer, Copenhagen). For this purpose, the emulsion was first cooled to + 20 ° C. At this temperature, the emulsions showed a conductivity of over 50 microsiemens per cm, i.e. H. they were in the form of oil-in-water emulsions.
  • a conductivity diagram was created by slowly heating at a heating rate of approximately 0.5 ° C./min, which was controlled with the aid of a temperature programmer in conjunction with a cryostat. The temperature range within which the conductivity dropped to values below 5 microsiemens per cm was noted as the phase inversion temperature range.
  • composition according to Table 1, column B2 was brought to 65 ° C, i.e. a temperature below the PIT.
  • the resulting emulsion was coarse.
  • Table 2 shows the phase inversion temperature (PIT) of the compositions of Examples B1 to B5.
  • the value of the PIT was obtained from the experimentally determined phase inversion temperature range mentioned under 2.3 by averaging.
  • the emulsions B1 to B5 prepared by the process according to the invention were further diluted with water (dilution factor: 2.26).
  • the composition of the emulsions obtained is shown in columns B1 * to B5 * in Table 3. It was found that the emulsions B1 * to B5 * in terms of fineness (measured by quasi-elastic light scattering) and storage stability (no segregation phenomena in the case of storage for several months) of the composition VI *, which were obtained by diluting the mixture according to 2.4. composition VI obtained was superior (see Table 4).
  • Emulsion type e fine fine fine fine fine coarse

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

Abstract

On obtient des émulsions huile dans eau caractérisées par une dispersion fine et une stabilité à long terme, à base de mélanges d'huiles comportant une certaine proportion d'une substance active organique cosmétique, en émulsionnant (A) un produit huileux avec (B) 0,5 à 30 % en poids d'un émulsifiant non ionique avec un équilibre hypophile-lipophile compris entre 10 et 18 et (C) 0 ou 0,1 à 30 % en poids d'un coémulsifiant du groupe des alcools gras avec 12 à 22 atomes de C ou des esters partiels de polyols avec 3 à 6 atomes de C avec des acides gras comportant 12 à 22 atomes de C et (D) un produit cosmétique organique choisi dans le groupe des désodorisants, des huiles de parfumerie et des agents photoprotecteurs, à la condition que i) la somme des composants (A) et (D) représente 10 à 90 % en poids et que ii) la proportion de composants (D), rapportée au produit huileux (A), soit comprise entre 5 et 100 % en poids, en présence de 8 à 85 % en poids d'eau à une température supérieure au point de fusion du mélange des composants (A) à (D), et en chauffant l'émulsion jusqu'à une température comprise dans le domaine de température de l'inversion de phase ou au-delà, ou en produisant l'émulsion à cette température, et en refroidissant ensuite l'émulsion jusqu'à une température inférieure au domaine de température de l'inversion de phase et en la diluant, le cas échéant, avec de l'eau.
EP94930201A 1993-10-29 1994-10-20 Procede de realisation d'emulsions huile dans eau Withdrawn EP0725619A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4337041A DE4337041A1 (de) 1993-10-29 1993-10-29 Verfahren zur Herstellung in Öl-in-Wasser-Emulsionen
DE4337041 1993-10-29
PCT/EP1994/003457 WO1995011660A1 (fr) 1993-10-29 1994-10-20 Procede de realisation d'emulsions huile dans eau

Publications (1)

Publication Number Publication Date
EP0725619A1 true EP0725619A1 (fr) 1996-08-14

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EP94930201A Withdrawn EP0725619A1 (fr) 1993-10-29 1994-10-20 Procede de realisation d'emulsions huile dans eau

Country Status (4)

Country Link
EP (1) EP0725619A1 (fr)
JP (1) JPH09504281A (fr)
DE (1) DE4337041A1 (fr)
WO (1) WO1995011660A1 (fr)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19530220A1 (de) * 1995-08-17 1997-02-20 Henkel Kgaa Translucente Antitranspirantien/Deodorantien
DE19548015A1 (de) * 1995-12-21 1997-06-26 Beiersdorf Ag Kosmetische und dermatologische Lichtschutzformulierungen mit einem Gehalt an hydrophoben anorganischen Mikropigmenten
DE19548014A1 (de) * 1995-12-21 1997-06-26 Beiersdorf Ag Kosmetische und dermatologische Lichtschutzformulierungen in Form von Emulsionen, insbesondere O/W-Makroemulsionen, O/W-Mikroemulsionen oder O/W/O-Emulsionen, mit einem Gehalt an in fester, dispergierter Form vorliegenden, in Ölkomponenten schwerlöslichen oder unlöslichen UV-Filtersubstanzen
DE19547986C1 (de) * 1995-12-21 1997-07-10 Henkel Kgaa O/W-Mikroemulsionen
DE19548016A1 (de) * 1995-12-21 1997-06-26 Beiersdorf Ag Kosmetische und dermatologische Lichtschutzformulierungen in Form von O/W-Makroemulsionen, O/W-Mikroemulsionen oder O/W/O-Emulsionen mit einem Gehalt an in gelöster Form vorliegenden, an sich schwerlöslichen UV-Filtersubstanzen, insbesondere Triazinderivaten
DE19703087C2 (de) 1997-01-29 1999-04-22 Henkel Kgaa Verwendung von PIT-Emulsionen
DE19713793A1 (de) 1997-04-03 1998-10-08 Henkel Kgaa Öl-in-Wasser-Emulsionen zur Wiederherstellung der Lamellarität der Lipidstruktur geschädigter Haut
DE19719504C1 (de) 1997-05-12 1998-12-10 Henkel Kgaa Verfahren zur Herstellung von Haarfärbemitteln
DE19726172A1 (de) * 1997-06-20 1998-12-24 Beiersdorf Ag Kosmetische und dermatologische Lichtschutzformulierungen in Form von Emulsionen, insbesondere O/W-Makroemulsionen, O/W-Mikroemulsionen oder O/W/O-Emulsionen, mit einem Gehalt an s-Triazinderivaten
DE19726189A1 (de) * 1997-06-20 1998-12-24 Beiersdorf Ag Kosmetische und dermatologische Lichtschutzformulierungen in Form von O/W-Makroemulsionen, O/W-Mikroemulsionen oder O/W/O-Emulsionen mit einem Gehalt an in gelöster Form vorliegenden s-Triazinderivaten
FR2787025B1 (fr) * 1998-12-14 2002-10-11 Oreal Composition sous forme d'emulsion h/e a forte teneur en cire et ses utilisations dans les domaines cosmetique et dermatologique
DE19908559A1 (de) * 1999-02-27 2000-09-07 Cognis Deutschland Gmbh PIT-Emulsionen
GB9912476D0 (en) 1999-05-28 1999-07-28 Novartis Ag Organic compounds
DE10000210A1 (de) * 2000-01-05 2001-07-12 Beiersdorf Ag Kosmetische oder dermatologische Zubereitungen vom Typ Öl-in-Wasser
DE10000209A1 (de) * 2000-01-05 2001-07-12 Beiersdorf Ag Kosmetische oder dermatologische Zubereitungen vom Typ Öl-in-Wasser
BRPI0514806A (pt) † 2004-08-31 2008-06-24 Connetics Australia Pty Ltd composições e processo de microemulsão e emulsão sub-mìcron
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JPH09504281A (ja) 1997-04-28
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