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WO1997023192A1 - Micro-emulsions huile dans eau contenant des agents tensioactifs saccharins et leur procede de preparation - Google Patents

Micro-emulsions huile dans eau contenant des agents tensioactifs saccharins et leur procede de preparation Download PDF

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Publication number
WO1997023192A1
WO1997023192A1 PCT/EP1996/005552 EP9605552W WO9723192A1 WO 1997023192 A1 WO1997023192 A1 WO 1997023192A1 EP 9605552 W EP9605552 W EP 9605552W WO 9723192 A1 WO9723192 A1 WO 9723192A1
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WO
WIPO (PCT)
Prior art keywords
carbon atoms
water
acid
alkyl
oil
Prior art date
Application number
PCT/EP1996/005552
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German (de)
English (en)
Inventor
Thomas Förster
Marcus Claas
Bettina Jackwerth
Barbara Heide
Marianne Waldmann-Laue
Gert-Lothar Striepling
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
Publication of WO1997023192A1 publication Critical patent/WO1997023192A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical

Definitions

  • the invention relates to O / W microemulsions containing sugar surfactant and to a process for their preparation.
  • Microemulsions are optically isotropic, thermodynamically stable systems that 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 are essentially below 300 nm, fine particles in the range between 100 and 300 nm, brown-red in transparency and bluish shimmering in incident light and less than 100 nm in range optically clear microemulsions occur.
  • 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 consist of oil components, water and Emulsifiers formed three-phase diagram are usually very small and the location of these areas of existence is greatly influenced by structural features of all components and all other ingredients 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.
  • DE-A-40 33 928 describes oil-in-water emulsions of water-insoluble oil components which contain an alkyl glucoside as an emulsifier.
  • the complex object of the present invention was to produce microemulsions with high proportions of polar oil components.
  • the invention accordingly relates to O / W microemulsions comprising:
  • AI 30 to 100% by weight of the mono- and / or diesters of the formulas (I), (II) and / or (III) (I) R'-COOR 2 (II) R 2 -OOC-R 3 -COOR 2
  • R'-COO-R 3 -OOC-R ' wherein R 1 and R are alkyl groups with 1 - 22 C atoms or alkenyl groups with 8 - 22 C atoms and R 3 for alkylene groups with 2 - 16 C atoms, and which contain a total of at least 10 C atoms, and / or A2) Fatty acid triglycerides of fatty acids with 8-22 carbon atoms.
  • microemulsions with a high polar oil content can be produced in the oil phase, only small amounts of co-emulsifier being used.
  • the invention includes the knowledge that the microemulsions have good refatting properties.
  • the oil body of the microemulsions according to the invention consists of 30 to 100, preferably 50 to 95% by weight of mono- and / or diesters of the formulas
  • R 1 and R 2 are alkyl groups with 1 to 22 carbon atoms or alkenyl groups with 8 to 22 carbon atoms and R 3 are alkylene groups with 2 to 16 carbon atoms and which contain a total of at least 10 carbon atoms, and / or fatty acid triglycerides of fatty acids with 8-22 carbon atoms.
  • Oil components 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 monoesters and diesters of this type the most important in the context of the present invention are the branched and / or unsaturated products which are liquid at room temperature (20 to 25 ° C.).
  • Other suitable monoesters are e.g. B. n-butyl stearate, n-hexyl laurate. n-isononanoate, 2-ethylhexyl palmitate, 2-ethylhexyl laurate, 2-hexyldecyl stearate. 2-octyldodecyl palmitate, oleyl oleate.
  • Oleylerucate, erucyl oleate and esters which are obtainable from technical aliphatic alcohol mixtures and technical aliphatic carboxylic acids.
  • esters of saturated and unsaturated fatty acids with 12-22 C atoms and polyols of the neopentyl type such as neopentyl glycol, trimethylolpropane, trimethylolethane, pentaerythritol, ditrimethylpropane, dipentaerythritol and tripentaerythritol, can also be used.
  • Suitable dicarboxylic acid esters (II) are e.g. B. Di-n-butyl adipate. Di-n-butyl sebacate, di- (2-ethylhexyl) adipate, di- (2-hexyldecyl) succinate and di-isotridecylacelate.
  • Suitable diol esters (III) are e.g. B. ethylene glycol dioleate. Ethylene glycol isotridecanoate, propylene glycol di (2-ethylhexanoate), butanediol diisostearate and neopentyl glycol dicaprylate.
  • branched and / or unsaturated fatty acid monoesters are particularly preferably used, e.g. Isopropyl isostearate or decyl oleate.
  • non-water-miscible organic compound all, per se, liquid, water-insoluble, linear, preferably branched and / or unsaturated hydrocarbons, ethers or esters as well as fatty oils (triglycerides) and / or fatty alcohols, in particular Guerbet alcohols such as at room temperature (20 to 25 ° C) e.g. 2-octyldodecanol. be used.
  • Guerbet alcohols such as at room temperature (20 to 25 ° C) e.g. 2-octyldodecanol.
  • solid or higher-melting paraffins can also be used.
  • Esters, waxes or fats are used in such quantities that the mixture with the liquid oil components remains liquid at 20 ° C.
  • Mineral oils and synthetically produced hydrocarbons e.g. B. liquid polyolefins or hydrocarbons, such as. B. alkylcyclohexanes such. B. 1,3-Diisooctylcyclohexane.
  • Sugar surfactants can be used as emulsifiers for the purposes of the present invention. According to the invention, sugar surfactants are to be understood as the following compounds:
  • Alkyl and alkenyl oligoglycosides are known nonionic surfactants which follow the formula (IV) R 4 0- [G] p (IV)
  • the alkyl and / or alkenyl oligoglycosides can be derived from aldoses or ketoses with 5 or 6 carbon atoms, preferably glucose.
  • the preferred alkyl un ⁇ V or alkenyl oligoglycosides are thus alkyl and / or alkenyl oligogiucosides.
  • the alkyl or alkenyl radical R 4 can be derived from primary alcohols having 8 to 22, in particular 8 to 18 and particularly preferably 12 to 16, carbon atoms. Typical examples are caprylic alcohol, capric alcohol, undecyl alcohol. Lauryl alcohol, myristyl alcohol, cetyl alcohol.
  • Alkyl oligoglucosides based on C 12/16 and C g / 16 fatty alcohol cuts with a DP of 1 to 3 are preferred.
  • Fatty acid N-alkylpolyhydroxyalkylamides are nonionic surfactants which follow the formula (V)
  • R 5 CO stands for an aliphatic acyl radical with 8 to 22 carbon atoms
  • R for hydrogen, an alkyl or hydroxyalkyl radical with 1 to 4 carbon atoms
  • [Z] for a linear or branched polyhydroxyalkyl radical with 3 to 12 carbon atoms and 3 to 10 hydroxyl groups .
  • the fatty acid N-alkyl polyhydroxyalkylamides are known substances which can usually be obtained by reductive amination of a reducing sugar with ammonia, an alkylamine or an alkanolamine and subsequent acylation with a fatty acid, a fatty acid alkyl ester or a fatty acid chloride.
  • a reducing sugar with ammonia, an alkylamine or an alkanolamine
  • subsequent acylation with a fatty acid, a fatty acid alkyl ester or a fatty acid chloride With regard to the processes for their preparation, reference is made to US Pat. Nos. 1,985,424, 2,016,962 and 2,703,798, as well as international patent application WO 92/06984. An overview of this topic by H. Kelkenberg can be found in Tens. Surf.Det. 25, 8 (1988).
  • the fatty acid N-alkylpolyhydroxyalkylamides are preferably derived from reducing sugars with 5 or 6 carbon atoms, in particular from glucose.
  • the preferred fatty acid N-alkylpolyhydroxyalkylamides are therefore fatty acid N-alkylglucamides as represented by the formula (VI):
  • the fatty acid N-alkylpolyhydroxyalkylamides used are preferably glucamides of the formula (VI) in which R is hydrogen or an alkyl group and R CO is an acyl radical having 8 to 22 carbon atoms, such as, for example: from caprylic acid.
  • Fatty acid N-alkyl-glucamides of the formula (VI) are particularly preferred which are obtained by reductive amination of glucose with methylamine and subsequent acylation with lauric acid, C 12/14 coconut fatty acid or C 12/16 and C g / 16 fatty acid cuts or a corresponding derivative can be obtained.
  • the polyhydroxyalkylamides can also be derived from maltose and palatinose.
  • fatty acid N-alkylpolyhydroxyalkylamides are also the subject of a large number of publications. Their use as a thickener is known, for example, from European patent application EP-AI 0 285 768 (Hüls).
  • French patent application FR-A 1 580 491 (Henkel) are aqueous detergent mixtures based on sulfates and / or sulfonates.
  • Nonionic surfactants and optionally soaps are described which contain fatty acid N-alkylglucamides as foam regulators. Mixtures of short- and long-chain glucamides are described in German Patent DE-Cl 44 00 632 (Henkel).
  • German Offenlegungsschriften DE-Al 42 36 958 and DE-Al 43 09 567 also report on the use of glucamides with longer alkyl residues than pseudoceramides in skin care products and on combinations of glucamides with protein hydrolyzates and cationic surfactants in hair care products.
  • Methyl ester sulfonates and nonionic surfactants are described in international patent applications WO 92/06152; 06154; 06155; 06161; 06162; 06164; 06170; 06171 and 06172 (Procter & Gamble).
  • Fatty acid polyol partial esters can be used as co-emulsifiers for the purposes of the present application.
  • Monoesters or the technical mixtures of monoesters, diesters and free polyol obtained in the esterification of the polyols with 1 to 2 mol of fatty acid are preferably used.
  • the fatty acid polyol partial esters are derived from fatty acids with 10 to 18 carbon atoms and polyols with 2 to 6 carbon atoms and 2 to 6 hydroxyl groups.
  • Suitable polyols are propylene glycol, glycerol, erythritol, trimethylolpropane, pentaerythritol, sorbitol, diglycerol, methyl glucoside or aldoses such as glucose or mannose.
  • Suitable fatty acid polyol Partial esters are, for example, the technical glycerol or sorbitan monoesters of lauric acid, myristic acid, palmitic acid. Stearic acid. Oleic acid or technical coconut fatty acid C 8 -C u cuts. Glycerol monooleate is preferably used.
  • anionic surfactants are alkylbenzenesulfonates. Alkanesulfonates. Olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates.
  • ⁇ - methyl ester sulfonates sulfo fatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, hydroxymixed ether sulfates, monoglyceride (ether) sulfates, fatty acid amide (ether) sulfates, mono- and dialkyl sulfosuccinates, mono- and dialkyl sulfosuccinamides, carbonic acid sulfates, sulfonate fatty acids, sulfonate fatty acids, sulfonate acid sulfate acids, sulfonate acid sulfate acids, sulfonate acid sulfate acid, sulfonate acid sulfate acid, sulfonate acid sulfate acid, sulfonate acid sulfate acid, sulfonate acid sulfate
  • anionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.
  • amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amido betaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines.
  • the surfactants mentioned are exclusively known compounds. With regard to the structure and manufacture of these substances, relevant reviews are, for example, J.Falbe (ed.), “Surfactants in Consumer Products”, Springer Verlag, Berlin, 1987, pp. 54-124 or J.Falbe (ed.), “Catalysts, surfactants and mineral oil additives”, Thieme Verlag, Stuttgart, 1978, pp. 123-217.
  • the microemulsions according to the invention can be made using water.
  • Propylene glycol, glycerin or other usual water-soluble skin care substances can be diluted to the desired application concentration.
  • conventional cosmetic thickeners such as e.g. Xanthan or hydrophobically modified polyacrylate can be added.
  • the water phase can contain a salt which is selected from the group formed by alkali, alkaline earth and / or ammonium halides, sulfates and / or hydrogen sulfates.
  • the emulsions according to the invention are usually prepared in a two-stage cold process. If necessary, for example when using glycerol monooleate as an emulsifier, the ingredients can also be emulsified at elevated temperature. First the oil body, the emulsifier and the co-emulsifier are emulsified with water. Subsequently, for example, perfume oil is added and the microemulsion can be diluted with water, propylene glycol and / or glycerol to the desired application concentration or viscosity-increasing substances can be added.
  • the weight ratio of emulsifier to oil can be 1: 4 to 3: 1, a weight ratio in the range from 1: 3 to 1: 1 is preferred.
  • the weight ratio of emulsifier to co-emulsifier can be 1: 2 to 8: 1, preferably the weight ratio is 1: 1 to 4: 1.
  • the microemulsion can have a water content of 20 to 95% by weight. microemulsions with a water content of 60 to 90% by weight are preferred.
  • O / W microemulsions according to the invention are preferably suitable for "2-in-1" skin and body care products such as, for example, facial cleansers, owing to the moisturizing effect.
  • microemulsions according to the invention By adding small amounts of the microemulsions according to the invention to surfactant preparations such as shampoos.
  • shower bath formulations, foam bath preparations or liquid soaps noticeably improve the skin feel and the anti-aging effect for hair.
  • the antistatic effect of only 1% by weight of a microemulsified oil component in a shampoo formulation based on alkyl polyglucosides is more pronounced than that of adding 0.1% by weight of a commercially available cationic cellulose ether.
  • the O / W microemulsions according to the invention can be produced in a two-stage cold process.
  • the amounts of sugar surfactant specified in the recipes (Tables 1 and 2) are emulsified with the corresponding amounts of ester oils and emulsifiers with stirring.
  • waxy co-emulsifiers e.g. Glycerin monooleate
  • a temperature increase is required to melt the glycerol monooleate (approx. 65 ° C).
  • the perfume oil and water are added.
  • a water-clear microemulsion is obtained, which is e.g. suitable as a facial cleanser.
  • the transmission of the solutions was determined photometrically at 650 nm.
  • Table 1 Recipes for microemulsions (% by weight based on active substance)
  • the cleaning performance was determined as follows:
  • a soiling paste consisting of 86 g kaolin, 8 g carbon black, 4 g Fe (black), 2 g Fe (yellow) and 300 g sebum. was applied to pig epidermis and then cleaned with a rubbing device. The evaluation was carried out using reflection measurements, which were determined in relation to the initial reflection.
  • the skin is extracted from an extract
  • HPLC determines the content of fats / oils not naturally found in the skin.

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  • Chemical & Material Sciences (AREA)
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Abstract

Ces micro-émulsions huile dans eau contiennent: (A) une phase huile à base de (A1) monoesters et/ou diesters et/ou de (A2) triglycérides d'acides gras; (B) des émulsifiants tels que (B1) des N-alkylpolyhydroxyalkylamides d'acides gras et/ou (B2) des oligoglycosides d'alkyle et/ou d'alcényle, ainsi que (C) des esters partiels d'acides gras avec des polyols comme co-émulsifiants. Ces micro-émulsions huile dans eau peuvent être préparées à froid en deux étapes et se caractérisent par leur stabilité au stockage, leur compatibilité avec l'environnement et leurs excellentes propriétés nourrissantes .
PCT/EP1996/005552 1995-12-21 1996-12-12 Micro-emulsions huile dans eau contenant des agents tensioactifs saccharins et leur procede de preparation WO1997023192A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19547986.6 1995-12-21
DE1995147986 DE19547986C1 (de) 1995-12-21 1995-12-21 O/W-Mikroemulsionen

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2767695A1 (fr) * 1997-08-28 1999-03-05 Henkel Kgaa Agents aqueux de nettoyage de la peau sous forme d'emulsion
EP0927553A2 (fr) * 1997-12-13 1999-07-07 Henkel KGaA Microémulsions
US6458373B1 (en) 1997-01-07 2002-10-01 Sonus Pharmaceuticals, Inc. Emulsion vehicle for poorly soluble drugs
JP2005526187A (ja) * 2002-02-15 2005-09-02 コグニス・ドイッチュランド・ゲゼルシヤフト・ミト・ベシュレンクテル・ハフツング・ウント・コンパニー・コマンデイトゲゼルシヤフト 肌に優しい不織布材料の製造用水性媒体
US7030155B2 (en) 1998-06-05 2006-04-18 Sonus Pharmaceuticals, Inc. Emulsion vehicle for poorly soluble drugs
EP1700618A1 (fr) * 2005-03-11 2006-09-13 Goldschmidt GmbH Emulsion cosmétique stable dans le temps
US9655821B2 (en) 2013-04-05 2017-05-23 The Procter & Gamble Company Personal care composition comprising a pre-emulsified formulation
US9993404B2 (en) 2015-01-15 2018-06-12 The Procter & Gamble Company Translucent hair conditioning composition
US10806688B2 (en) 2014-10-03 2020-10-20 The Procter And Gamble Company Method of achieving improved volume and combability using an anti-dandruff personal care composition comprising a pre-emulsified formulation
US10912723B2 (en) 2016-01-20 2021-02-09 The Procter And Gamble Company Hair conditioning composition comprising monoalkyl glyceryl ether

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19723733A1 (de) * 1997-06-06 1998-12-10 Beiersdorf Ag Kosmetische und dermatologische Emulsionen, enthaltend Alkylglucoside und erhöhte Elektrolytkonzentrationen
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
GB2086893A (en) * 1980-10-24 1982-05-19 Oreal Non-ionic-surface-active agents derived from glucose
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
DE4337041A1 (de) * 1993-10-29 1995-05-04 Henkel Kgaa Verfahren zur Herstellung in Öl-in-Wasser-Emulsionen
DE4417476A1 (de) * 1994-05-19 1995-11-23 Henkel Kgaa Mikroemulsionen

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3723826A1 (de) * 1987-07-18 1989-01-26 Henkel Kgaa Verfahren zur herstellung von alkylglykosiden
DE4236958A1 (de) * 1992-11-02 1994-08-18 Weber Haus Gmbh & Co Kg Verbindungsstück und eine verlorene Schalung
DE4309567A1 (de) * 1993-03-24 1994-09-29 Henkel Kgaa Detergensgemische

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2086893A (en) * 1980-10-24 1982-05-19 Oreal Non-ionic-surface-active agents derived from glucose
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
DE4337041A1 (de) * 1993-10-29 1995-05-04 Henkel Kgaa Verfahren zur Herstellung in Öl-in-Wasser-Emulsionen
DE4417476A1 (de) * 1994-05-19 1995-11-23 Henkel Kgaa Mikroemulsionen

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6458373B1 (en) 1997-01-07 2002-10-01 Sonus Pharmaceuticals, Inc. Emulsion vehicle for poorly soluble drugs
US6660286B1 (en) 1997-01-07 2003-12-09 Sonus Pharmaceuticals, Inc. Emulsion vehicle for poorly soluble drugs
US6667048B1 (en) 1997-01-07 2003-12-23 Sonus Pharmaceuticals, Inc. Emulsion vehicle for poorly soluble drugs
US6982282B2 (en) 1997-01-07 2006-01-03 Sonus Pharmaceuticals, Inc. Emulsion vehicle for poorly soluble drugs
FR2767695A1 (fr) * 1997-08-28 1999-03-05 Henkel Kgaa Agents aqueux de nettoyage de la peau sous forme d'emulsion
EP0927553A2 (fr) * 1997-12-13 1999-07-07 Henkel KGaA Microémulsions
EP0927553A3 (fr) * 1997-12-13 2001-05-30 Cognis Deutschland GmbH Microémulsions
US7030155B2 (en) 1998-06-05 2006-04-18 Sonus Pharmaceuticals, Inc. Emulsion vehicle for poorly soluble drugs
JP2005526187A (ja) * 2002-02-15 2005-09-02 コグニス・ドイッチュランド・ゲゼルシヤフト・ミト・ベシュレンクテル・ハフツング・ウント・コンパニー・コマンデイトゲゼルシヤフト 肌に優しい不織布材料の製造用水性媒体
EP1700618A1 (fr) * 2005-03-11 2006-09-13 Goldschmidt GmbH Emulsion cosmétique stable dans le temps
US9655821B2 (en) 2013-04-05 2017-05-23 The Procter & Gamble Company Personal care composition comprising a pre-emulsified formulation
US10806688B2 (en) 2014-10-03 2020-10-20 The Procter And Gamble Company Method of achieving improved volume and combability using an anti-dandruff personal care composition comprising a pre-emulsified formulation
US9993404B2 (en) 2015-01-15 2018-06-12 The Procter & Gamble Company Translucent hair conditioning composition
US10912723B2 (en) 2016-01-20 2021-02-09 The Procter And Gamble Company Hair conditioning composition comprising monoalkyl glyceryl ether

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