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WO1995031957A1 - Micro-emulsions - Google Patents

Micro-emulsions Download PDF

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Publication number
WO1995031957A1
WO1995031957A1 PCT/EP1995/001765 EP9501765W WO9531957A1 WO 1995031957 A1 WO1995031957 A1 WO 1995031957A1 EP 9501765 W EP9501765 W EP 9501765W WO 9531957 A1 WO9531957 A1 WO 9531957A1
Authority
WO
WIPO (PCT)
Prior art keywords
water
fatty acid
oil phase
weight
polyol
Prior art date
Application number
PCT/EP1995/001765
Other languages
German (de)
English (en)
Inventor
Thomas Förster
Marcus Claas
Werner Seipel
Bernhard Guckenbiehl
Armin Wadle
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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 Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to EP95921741A priority Critical patent/EP0759737A1/fr
Publication of WO1995031957A1 publication Critical patent/WO1995031957A1/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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/068—Microemulsions
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
    • 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
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/017—Mixtures of compounds
    • C09K23/018—Mixtures of two or more different organic oxygen-containing compounds

Definitions

  • the invention relates to microemulsions and a process for their preparation, in which a combination of an alkyl glycoside and a fatty acid polyol ester is used as the emulsifier.
  • Microemulsions are optically isotropic, thermodynamically stable systems which contain a water-insoluble oil component, emulsifiers and water.
  • the clear or transparent appearance of the microemulsions is a consequence of the small particle size of the dispersed emulsion droplets, which is essentially below 300 nm, fine particles in the range between 100 and 300 nm, brown-red in the view and bluish shimmer in the reflected light, and in the range optically clear microemulsions occur below 100 nm.
  • the droplet size of macroemulsions is essentially over 300 nm.
  • Microemulsions are frequently described in the literature, but their targeted production is associated with great difficulties, since the areas of existence of the microemulsion in the oil component, water The three-phase diagram formed by this and the emulators are usually very small and the location of these areas of existence is greatly influenced by structural features of all components and all other constituents of such systems.
  • microemulsions are of considerable importance in the formulation of cosmetic and pharmaceutical preparations. There is therefore a need for reliable methods of producing microemulsions.
  • the invention accordingly relates to a microemulsion of a water-insoluble oil phase (A) in water (C), the oil phase (A) being liquid at 20 ° C. and preferably excluding more than 70% by weight.
  • lent consists of hydrocarbons or dialkyl ethers, each with at least 10 carbon atoms or mixtures thereof, and a combination of as emulsifier (B)
  • (B2) a fatty acid-polyol partial ester with an HLB value below 11 consisting of a fatty acid with 10 to 18 carbon atoms and a polyol with 2-8 hydroxyl groups
  • Suitable oil components are preferably liquid hydrocarbons or dialkyl ethers with 10-32 carbon atoms. However, higher molecular or solid paraffins can also be used in a mixture with these as long as the mixture remains liquid at 20 ° C.
  • Suitable hydrocarbons are e.g. n-decane, n-dodecane, n-tetradecane, n-hexadecane, isohexadecane, l, 3-di- (2-ethylhexyl) cyclohexane, triisobutene, pentapropylene and other liquid oligo-olefins and their hydration products, paraffin oils and squalane .
  • Suitable dialkyl ethers are e.g. Lauryl butyl ether, myristyl methyl ether, cetyl hexyl ether, di-n-octyl ether, di-n-decyl ether, decyl octyl ether, di-n-lauryl ether.
  • the aliphatic dialkyl ethers * with 6-10 C atoms per alkyl group are particularly suitable.
  • oils in particular those used in cosmetics, for example esters, triglycerides or fatty alcohols, can also be used as oil components. However, their proportion should not exceed 25% by weight of the water-insoluble oil phase.
  • Alkyl glycosides (B1) their preparation and use as surface-active substances are known, for example, from DE 19 43 689 or from DE 3827 543. They are produced by reacting glucose or oligosaccharides with primary alcohols with 8 to 14 carbon atoms or by acetalizing starch with, for example, lower alcohols and re-acetalizing it with the C ⁇ -C ⁇ fatty alcohol.
  • glycoside residue both monoglycosides in which a cyclic sugar residue is glycosidically linked to the fatty alcohol and oligomeric glycosides with a degree of oligomerization of up to about 3 are suitable.
  • Suitable alkyl glycosides for the preparation of the microemulsion according to the invention are those of the general formula R * 0 - (G) x , in which R 1 is an aliphatic radical of a primary fatty alcohol having 8 to 14 C atoms and (G) x is an oligoglucoside radical with a medium one Degree of oligomerization x is from 1 to 3.
  • Oligoglucosides of the aforementioned general formula are particularly preferred, in which R * denotes a linear alkyl group with 8 to 12 C atoms and (G) x denotes an oligoglucoside residue with an average degree of oligomerization x of 1 to 2. It can also be technical mixtures with small amounts of C j ö-alkyl glycosides.
  • the average degree of oligomerization results from the molar proportions of the individual oligomers by dividing the sum of the structural units by the sum of the molecules (cf. Principles of Polymer Chemistry, Paul J. Flory, Georgia University Press, Ithaca, New York 1953, page 35-36).
  • Fatty acid-polyol partial esters (B2) suitable as lipophilic co-emulsifiers are preferably the monoesters or the technical mixtures of monoesters, diesters and free polyol obtained by esterifying the polyols with 1-2 moles of fatty acid or by transesterifying the polyols with 1-2 moles of fatty acid methyl ester suitable.
  • suitable polyols are propylene glycol, glycerol, erythritol, triethylolpropane, pentaerythritol, sorbitol, diglycerol, aldoses such as glucose or mannose, ketoses such as fructose or disaccharides such as sucrose, maltose or lactose or alkylglycosides, for example methylglucoside, butylglucoside or laurylglucoside, with an average degree of oligomerization of 1-2.
  • Suitable fatty acid polyol partial esters are, for example, the technical ones Glycerol or sorbitan monoesters of lauric acid, myristic acid or of technical coconut fatty acid C8-Ci4 cuts. Sorbitan monolaurate and lauric acid onoglyceride are preferably used.
  • Other suitable fatty acid-polyol partial esters are, for example, triglycerol diisostearate, methylgucoside sesquistearate, laurylglucoside monolaurate.
  • L is the proportion of alkyl or acyl groups in% by weight of the molecular weight.
  • the emulsifier combination (B) is preferably used in an amount of 0.2-0.5 parts by weight per part by weight of the oil phase (A).
  • higher amounts of up to 1.5 parts by weight per part by weight of the oil component may be required.
  • the water content of the microemulsions according to the invention is preferably 0.5 to 2 parts by weight of H2O per part by weight of the oil phase. se.
  • the microemulsions according to the invention can be diluted with water without changing the particle size.
  • the area of existence of the microemulsions according to the invention can also be expanded by dissolving electrolyte salts in the water phase, which makes microemulsions with a particularly high water content accessible.
  • Suitable electrolyte salts are, in particular, the ammonium, alkali and alkaline earth halides and the ammonium, alkali and magnesium sulfates and hydrogen sulfates, preferably in an amount of 0.02 to 2% by weight of the water phase.
  • Suitable electrolytes are e.g. Sodium chloride, sodium sulfate, magnesium chloride, ammonium chloride and ammonium sulfate.
  • Ionic surfactants can also be incorporated into the microemulsions according to the invention without the transparency and the particle size being impaired.
  • Suitable anionic surfactants are e.g.
  • Cio-Ciö fatty alcohol sulfate salts fatty alcohol polyglycol ether sulfate salts, acyl isethionate salts, acyl acid salts, sulfosuccinic acid monoester salts, soaps, fatty acid oligopeptide condensates (amide soaps) and fatty acid monoglyceride surfactants, sulfate compatible and other skin compatible sulfate anionics preferably in the form of their water-soluble ammonium, alkanolammonium, alkali or magnesium salts.
  • amphoteric, zwitterionic and cationic surfactants are also suitable.
  • microemulsions according to the invention are suitable as carriers for a large number of cosmetic or pharmaceutical active ingredients, but, owing to the clearly solubilized oil component, also as skin care lotion or make-up removal lotion.
  • the microemulsions according to the invention are converted into cosmetic cleaning agents which are of interest from an application point of view, for example of the type of foam bath and shower bath preparations, liquid soaps and body cleaning solutions which, owing to the stable and clearly solubilized oil components, have a particularly good skin and have mucosal compatibility.
  • the microemulsions according to the invention are prepared by mixing the components and simply stirring, e.g. using conventional emulsifying and homogenizing devices.
  • the water-soluble components e.g. the alkylglycoside (B1) as a concentrated solution in part of the water and the oil-soluble components, e.g. the fatty acid-polyol partial glyceride (B2) dissolved in the oil phase and the phases mixed in the usual way.
  • Ionic surfactants and the remaining amount of water are then added with stirring.
  • the use of heat is not necessary here, at most heat must be added to accelerate the dissolution of solid components.
  • the microemulsions according to the invention can contain customary auxiliaries and additives, e.g. Contain dyes, preservatives, fragrances and buffer substances for pH adjustment without the microemulsion form being disturbed.
  • auxiliaries and additives e.g. Contain dyes, preservatives, fragrances and buffer substances for pH adjustment without the microemulsion form being disturbed.
  • the transparency was determined using a Mettler photometer, model 662.
  • the mean particle size was determined on the principle of quasi-elastic light scattering using a Zetasizer 3 (from Malvern). Examples
  • Plantaren 1200 (1) 10 3.3 2 1.0 1.0 Sorbitan ono1aurat 10 3.3 2 1.0 1.0 C ⁇ 2_i4 fatty alcohol + 2.5 E0 (narrow ranks ethoxylate) _ _ _ _ 1.8 fatty alcohol ether sulfate (3) - - - - 9.0 water (+ citric acid to pH - 6 45 81.7 89 94.5 83.7
  • the phases were heated to 40 ° C., then the oil phase was emulsified into the aqueous phase with stirring. Homogeneous, optically isotropic microemulsions were formed. Small proportions of coarser emulsion particles (100 - 300 nm) can cause a sharp decrease in transparency (measured as transmission at 650 nm).
  • Emulsions No. 13-15 were obtained by diluting emulsion No. 7 with water, emulsion No. 16 by diluting emulsion No. 7 with a shampoo.
  • Plantaren 1200 alkyl (Ci2-i6) oligo (1,4) glucoside
  • Plantaren 2000 alkyl (C8_i6) oligo (1,4) glucoside

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Dermatology (AREA)
  • Dispersion Chemistry (AREA)
  • Cosmetics (AREA)
  • Colloid Chemistry (AREA)

Abstract

On obtient des micro-émulsions d'une phase huileuse (A), constituées à plus de 70 % en poids de préférence exclusivement d'hydrocarbures ou de dialcoyléthers ayant chacun au moins 10 atomes de C, de préférence à l'aide d'une combinaison d'émulsifiants (B) comprenant: (B1) un alkylglycoside de la formule R1O(G))x, dans laquelle R1 désigne un groupe alkyle linéaire ayant entre 8 et 14 atomes de C, G désigne un reste glycoside et x, son degré moyen d'oligomérisation, vaut entre 1 et 3, et (B2) un ester partiel de polyol d'acide gras dont l'équilibre hydrophile-lipophyle est inférieur à 11, issu d'un acide gras ayant entre 10 et 18 atomes de C et d'un polyol ayant entre 2 et 8 groupes hydroxyle. Les oligoglucosides les plus appropriés sont ceux de la formule citée, dans laquelle R1 désigne un groupe alkyle C¿8?-C12 et (G)x désigne un reste oligoglucoside ayant un degré moyen d'oligomérisation x compris entre 1 et 2. Les monoesters techniques de glycérine ou de sorbitanne d'acide laurique, d'acide myristique et de sous-systèmes techniques d'acide gras de coco C8-C14 constituent des esters partiels de polyol d'acide gras appropriés.
PCT/EP1995/001765 1994-05-19 1995-05-10 Micro-emulsions WO1995031957A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP95921741A EP0759737A1 (fr) 1994-05-19 1995-05-10 Micro-emulsions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4417476.4 1994-05-19
DE4417476A DE4417476A1 (de) 1994-05-19 1994-05-19 Mikroemulsionen

Publications (1)

Publication Number Publication Date
WO1995031957A1 true WO1995031957A1 (fr) 1995-11-30

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/001765 WO1995031957A1 (fr) 1994-05-19 1995-05-10 Micro-emulsions

Country Status (3)

Country Link
EP (1) EP0759737A1 (fr)
DE (1) DE4417476A1 (fr)
WO (1) WO1995031957A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999025797A1 (fr) * 1997-11-19 1999-05-27 Henkel Kommanditgesellschaft Auf Aktien Assouplissant clair contenant des huiles parfumees micro-emulsionnees
EP0801130A3 (fr) * 1996-04-18 1999-06-23 Hüls Aktiengesellschaft Composition de nettoyage sans forme de microémulsion contenant des agents tensioactifs
DE19929505A1 (de) * 1999-06-29 2001-01-11 Cognis Deutschland Gmbh Kosmetische Emulsionen
EP0927553A3 (fr) * 1997-12-13 2001-05-30 Cognis Deutschland GmbH Microémulsions
WO2001090286A1 (fr) * 2000-05-25 2001-11-29 Akzo Nobel Nv Microemulsion contenant un glycoside d'alkyle ramifie
EP2505180A1 (fr) * 2011-04-01 2012-10-03 Cognis IP Management GmbH Émulsions de particules fines comprenant des microémulsions
WO2012130413A3 (fr) * 2011-04-01 2014-04-17 Cognis Ip Management Gmbh Produit de soin capillaire
EP3678634B1 (fr) 2017-09-06 2023-10-04 Evonik Operations GmbH Composition contenant un composé d'ammonium quarternaire, en particulier pour la production de formulations de soins et de nettoyage
WO2024256470A1 (fr) * 2023-06-13 2024-12-19 Brenntag Holding Gmbh Nouvelle composition cosmétique d'origine naturelle triphasique

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19529907A1 (de) * 1995-08-15 1997-02-20 Henkel Kgaa Feinteilige Emulsionen enthaltend Zuckertenside
DE19539523A1 (de) * 1995-10-24 1997-04-30 Grace W R & Co Trennmittel für Walzen und Verfahren zur Verbesserung der Trenneigenschaften von Walzen
DE19547986C1 (de) * 1995-12-21 1997-07-10 Henkel Kgaa O/W-Mikroemulsionen
DE19624051A1 (de) * 1996-06-17 1997-12-18 Henkel Kgaa Parfümölkonzentrate
DE19624455C2 (de) * 1996-06-20 1998-08-27 Henkel Kgaa Sonnenschutzmittel in Form von O/W-Mikroemulsionen
DE19641672A1 (de) * 1996-10-10 1998-04-16 Beiersdorf Ag Kosmetische oder dermatologische Zubereitungen auf der Basis von ethylenoxidfreien und propylenoxidfreien Emulgatoren zur Herstellung von Mikroemulsionsgelen
DE19852784A1 (de) * 1998-11-16 2000-05-18 Max Planck Gesellschaft Osmotische Stabilisierung von Mini- und Mikroemulsionen und deren Anwendung zur Herstellung von Nanohybridpartikeln
JP2005521552A (ja) * 2002-03-26 2005-07-21 ザ プロクター アンド ギャンブル カンパニー ソルビタンモノエステル類を含有する組成物
BR0303286B1 (pt) 2003-08-29 2013-08-20 microemulsço cosmÉtica.

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4010393A1 (de) * 1990-03-30 1991-10-02 Henkel Kgaa Verfahren zur herstellung von oel-in-wasser-cremes
WO1992001508A1 (fr) * 1990-07-16 1992-02-06 Henkel Kommanditgesellschaft Auf Aktien Emulsions huile-eau
WO1992007543A1 (fr) * 1990-10-25 1992-05-14 Henkel Kommanditgesellschaft Auf Aktien Emulsions d'huile dans l'eau
EP0507047A2 (fr) * 1991-03-30 1992-10-07 Hüls Aktiengesellschaft Emulsifiants pour la préparation d'emulsions d'huiles étherées du type huile dans l'eau d'utilisables en cosmétique ou en médicine
WO1994016677A1 (fr) * 1993-01-23 1994-08-04 Henkel Kommanditgesellschaft Auf Aktien Melanges detergents possedant de meilleures proprietes d'avivage

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4010393A1 (de) * 1990-03-30 1991-10-02 Henkel Kgaa Verfahren zur herstellung von oel-in-wasser-cremes
WO1992001508A1 (fr) * 1990-07-16 1992-02-06 Henkel Kommanditgesellschaft Auf Aktien Emulsions huile-eau
WO1992007543A1 (fr) * 1990-10-25 1992-05-14 Henkel Kommanditgesellschaft Auf Aktien Emulsions d'huile dans l'eau
EP0507047A2 (fr) * 1991-03-30 1992-10-07 Hüls Aktiengesellschaft Emulsifiants pour la préparation d'emulsions d'huiles étherées du type huile dans l'eau d'utilisables en cosmétique ou en médicine
WO1994016677A1 (fr) * 1993-01-23 1994-08-04 Henkel Kommanditgesellschaft Auf Aktien Melanges detergents possedant de meilleures proprietes d'avivage

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0801130A3 (fr) * 1996-04-18 1999-06-23 Hüls Aktiengesellschaft Composition de nettoyage sans forme de microémulsion contenant des agents tensioactifs
WO1999025797A1 (fr) * 1997-11-19 1999-05-27 Henkel Kommanditgesellschaft Auf Aktien Assouplissant clair contenant des huiles parfumees micro-emulsionnees
EP0927553A3 (fr) * 1997-12-13 2001-05-30 Cognis Deutschland GmbH Microémulsions
DE19929505A1 (de) * 1999-06-29 2001-01-11 Cognis Deutschland Gmbh Kosmetische Emulsionen
DE19929505B4 (de) * 1999-06-29 2004-08-26 Cognis Deutschland Gmbh & Co. Kg Kosmetische Emulsionen
WO2001090286A1 (fr) * 2000-05-25 2001-11-29 Akzo Nobel Nv Microemulsion contenant un glycoside d'alkyle ramifie
EP2505180A1 (fr) * 2011-04-01 2012-10-03 Cognis IP Management GmbH Émulsions de particules fines comprenant des microémulsions
WO2012130413A3 (fr) * 2011-04-01 2014-04-17 Cognis Ip Management Gmbh Produit de soin capillaire
EP3678634B1 (fr) 2017-09-06 2023-10-04 Evonik Operations GmbH Composition contenant un composé d'ammonium quarternaire, en particulier pour la production de formulations de soins et de nettoyage
WO2024256470A1 (fr) * 2023-06-13 2024-12-19 Brenntag Holding Gmbh Nouvelle composition cosmétique d'origine naturelle triphasique
FR3149775A1 (fr) * 2023-06-13 2024-12-20 Brenntag Holding Gmbh Nouvelle composition cosmétique d’origine naturelle triphasique

Also Published As

Publication number Publication date
EP0759737A1 (fr) 1997-03-05
DE4417476A1 (de) 1995-11-23

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