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WO1997002002A2 - Utilisation de polyolpoly-12-hydroxystearates - Google Patents

Utilisation de polyolpoly-12-hydroxystearates Download PDF

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Publication number
WO1997002002A2
WO1997002002A2 PCT/EP1996/002750 EP9602750W WO9702002A2 WO 1997002002 A2 WO1997002002 A2 WO 1997002002A2 EP 9602750 W EP9602750 W EP 9602750W WO 9702002 A2 WO9702002 A2 WO 9702002A2
Authority
WO
WIPO (PCT)
Prior art keywords
weight
polyglycerol
poly
acid
hydroxystearates
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.)
Ceased
Application number
PCT/EP1996/002750
Other languages
German (de)
English (en)
Other versions
WO1997002002A3 (fr
Inventor
Annette Schwarz
Achim Ansmann
Rolf Kawa
Mark Leonard
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 WO1997002002A2 publication Critical patent/WO1997002002A2/fr
Publication of WO1997002002A3 publication Critical patent/WO1997002002A3/fr
Anticipated expiration legal-status Critical
Ceased 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
    • A61K8/18—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
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations

Definitions

  • the invention relates to the use of polyol poly-12-hydroxystearates as O / W emulsifiers for the production of cosmetic and / or pharmaceutical preparations.
  • Polyglycerol polyricinoleates have long been known as W / O emulsifiers and can be used to formulate low-viscosity W / O emulsions [cf. EP-AI 0 559 013 (Th. Goldschmidt), EP-AI 0 440 203 (Lotte Co.) and WO 85/04346 (Meiji Milk Prods.). It turns out, however, that polyglycerol polyrinoleates on the market do not form emulsions with all oils conventionally used in cosmetics, but only with those of a certain polarity range; moreover, these emulsions have only a limited shelf life. A major disadvantage is that the commercially available products are not able to adequately stabilize emulsions with strongly polar oils such as vegetable oils. In view of the particular ecotoxicological compatibility of such emulsions, however, this is precisely what is desired in the market.
  • polyglycerol polyricinoleates are not suitable for producing O / W emulsions because of their high lipophilicity; this requires significantly more hydrophilic, usually surfactant, emulsifiers.
  • the latter again have the disadvantage that they generally contain ethylene oxide groups, which is not always desirable from the market point of view.
  • the stability of the emulsions obtainable using known hydrophilic O / W emulsifiers is in many cases unsatisfactory.
  • the complex object of the invention was therefore to provide O / W emulsifiers which on the one hand are free of ethylene oxide and on the other hand allow the production of finely divided and at the same time storage-stable emulsions.
  • the invention relates to the use of polyol poly-12-hydroxystearates as O / W emulsifiers for the production of cosmetic and / or pharmaceutical preparations.
  • condensation products of polyols preferably technical polyglycerol
  • poly-12-hydroxystearic acid which are known to be suitable as W / O emulsifiers
  • condensation products based on the 12-hydroxystearic acid are liquid, although the acid used has a melting point in the range of 75 ° C.
  • the invention relates to the use of polyglycerol poly-12-hydroxystearates, which is obtained by poly-12-hydroxy stearic acid having a degree of self-condensation in the range from 2 to 20, preferably 2 to 10, with a polyglycerol mixture of the composition ( GC method)
  • polyols is understood to mean substances which have at least two, preferably 3 to 12 and in particular 3 to 8 hydroxyl groups and 2 to 12 carbon atoms. Typical examples are:
  • Allkylene glycols such as ethylene glycol, diethylene glycol, propylene glycol;
  • Methyl compounds such as, in particular, trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol;
  • Sugar alcohols having 5 to 12 carbon atoms such as, for example, sorbitol or mannitol,
  • reaction products based on polyglycerol are of particular importance among the O / W emulsifiers to be used according to the invention because of their excellent performance properties. It has proven particularly advantageous to use selected polyglycerols which have the following homolog distribution (the preferred ranges are given in brackets):
  • the polyol poly-12-hydroxystearates can be prepared in a manner known per se.
  • the polyglycerol and then the polyhydroxystearic acid are preferably first produced and finally both are esterified.
  • the preparation of a polyglycerol of the abovementioned composition can be carried out by self-condensation of glycerol in the presence of suitable catalysts such as, for example, potassium carbonate, silicates according to DE-Al 40 29 323 (Henkel) or borates according to DE-Al 41 17 033 (Henkel) at temperatures in the range of 200 to 260 ° C are carried out.
  • the poly-12-hydroxystearic acid is prepared, for example, by alkaline-catalyzed polycondensation of 12-hydroxystearic acid, which is obtained by curing ricinic acid or technical castor oil fatty acid. Linear esterification products having 2 to 10 and in particular 2 to 8 fatty acid units are preferably formed.
  • the following distribution (GPC method) is typically achieved:
  • mixtures of 12-hydroxystearic acid and ricinoleic acid or technical castor oil fatty acid which consists of approximately 90% by weight of ricinoleic acid, are used in a weight ratio of 99: 1 to 1:99 and preferably 75:25 to 10:90 .
  • polystyrene resin for example the polyglycerol with the poly-12-hydroxystearic acid or the mixtures with polyricinoleic acid
  • a complex mixture of homologous polyester is formed.
  • the proportions of mono-, di-, tri- and oligoesters in the polyol poly-12-hydroxystearates to be used according to the invention and preferably polyglycerol poly-12-hydroxystearates depend on the conditions of use of the starting compounds.
  • a polyol poly-12-hydroxystearate with particularly advantageous application properties is used, which is obtained by subjecting about 1000 kg of 12-hydroxystearic acid to self-condensation until a product with an acid number in the range from 50 to 55 results and this is then further esterified with about 150 kg of polyglycerol of the composition indicated above until the acid number has decreased to a value less than 2.
  • Condensation products based on polyglycerol and poly-12-hydroxystearic acid or poly-12-hydroxystearic acid / polyricinoleic acid can be characterized by their iodine number.
  • Typical examples are polyesters with an iodine number ⁇ 10 (based on 100% 12-hydroxystearic acid) or 65 to 80 (based on 90% 12-hydroxystearic acid, 10% ricinoleic acid).
  • the O / W emulsions or cosmetic or pharmaceutical preparations obtainable using the polyol poly-12-hydroxystearates can be used as further components, inter alia. Contain oil oils, co-emulsifiers, fats and waxes, stabilizers, thickeners, biogenic agents, film formers, fragrances, dyes, pearlescent agents, preservatives, UV filters, pigments, electrolytes (e.g. magnesium sulfate) and pH regulators.
  • suitable co-emulsifiers are hardened and ethoxylated castor oil, ethoxylated fatty alcohols or partial glycerides, alkyl oligoglycosides, polyglycerol fatty acid esters or polyglycerol polyricinoleates.
  • Substances such as polyethoxylated lanolin derivatives, lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides can be used as superfatting agents, the latter simultaneously serving as foam stabilizers.
  • Suitable thickeners are, for example, polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, and also higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, polyvinyl alcohol and polyvinylpyrrolidone, surfactants such as fatty alcohol ethoxylates with a narrow homolog distribution or alkyl oligoglucosides and electrolytes such as table salt and ammonium chloride.
  • Biogenic active substances are understood to mean, for example, plant extracts and vitamin complexes.
  • Common film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid or its salts and similar compounds.
  • Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid.
  • Suitable pearlescent agents are, for example, glycol distearic acid esters such as ethylene glycol distearate, but also fatty acid mono-glycol esters.
  • the dyes which can be used are the substances which are suitable and approved for cosmetic purposes, such as are listed, for example, in the publication "Cosmetic Dyes” by the Dye Commission of the German Research Foundation, Verlag Chemie, Weinheim, 1984, pp. 81-106. These dyes are usually used in concentrations of 0.001 to 0.1% by weight, based on the overall mixture.
  • the total proportion of auxiliaries and additives can be 1 to 50, preferably 5 to 40% by weight, based on the composition.
  • the O / W emulsions can be prepared in a manner known per se by the cold / cold, hot / hot, hot / cold or PIT method.
  • a facial cleansing cream To prepare a facial cleansing cream, the constituents I were melted at 80 ° C. and stirred until homogeneous. The components of phase II were also heated to 80 ° C., added slowly to phase I with stirring and emulsified at 80 ° C. for 5 minutes. The emulsion was cooled with stirring and carefully homogenized at about 50 ° C. After a temperature of 30 ° C. had been reached, the stirring was stopped and the emulsion was vented after cooling to room temperature. Using polyglycerol poly-12-hydroxystearate as an O / W emulsifier, a viscous cream was obtained which was still stable even after 12 weeks of storage. When using a known hydrophilic O / W emulsifier from the prior art, the mixture remained two-phase. The composition of the mixtures can be found in Table 1 (quantitative data as% by weight).
  • Emulgade® PL 1618 Hexadecyl Polyglucose and Hexadecyl Alcohol
  • Plantaren® 1200 decyl polyglucose
  • Myritol® 312 Caprylic / Capric Triglyceride
  • Dehymuls® PGPH polyglyceryl poly-12-hydroxystearate
  • Example 2 The procedure for producing a care cream was as described in Example 1.
  • the cream produced using the polyglycerol poly-12-hydroxystearate was still stable even after storage for more than 12 weeks; without the O / W emulsifier, the cream separated into an oily and an aqueous phase within 8 weeks.
  • the composition of the mixtures can be found in Table 2 (quantitative data as% by weight).

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Emergency Medicine (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne l'utilisation de polyolpoly-12-hydroxystéarates comme émulsifiants huile dans eau pour produire des préparations cosmétiques et/ou pharmaceutiques. Comparativement à l'utilisation d'émulsifiants hydrophiles connus, ce procédé permet d'obtenir des émulsions plus stables.
PCT/EP1996/002750 1995-07-03 1996-06-24 Utilisation de polyolpoly-12-hydroxystearates Ceased WO1997002002A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19524210.6 1995-07-03
DE19524210A DE19524210A1 (de) 1995-07-03 1995-07-03 Verwendung von Polyolpoly-12-hydroxystearaten

Publications (2)

Publication Number Publication Date
WO1997002002A2 true WO1997002002A2 (fr) 1997-01-23
WO1997002002A3 WO1997002002A3 (fr) 1997-02-13

Family

ID=7765899

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1996/002750 Ceased WO1997002002A2 (fr) 1995-07-03 1996-06-24 Utilisation de polyolpoly-12-hydroxystearates

Country Status (2)

Country Link
DE (1) DE19524210A1 (fr)
WO (1) WO1997002002A2 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102005005199A1 (de) * 2005-02-03 2006-08-10 Beiersdorf Ag Verwendung von Alkylglucosiden zum Erzielen oder Verbessern der mikrobiologischen Stabilität von kosmetischen Zubereitungen
JPWO2013069690A1 (ja) * 2011-11-07 2015-04-02 日清オイリオグループ株式会社 洗浄料用組成物及び洗浄料

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19548345C2 (de) * 1995-12-22 1998-10-15 Henkel Kgaa Verwendung von Mischungen spezieller Emulgatoren und Ölkörpern
DE19650473C1 (de) * 1996-12-05 1998-04-02 Henkel Kgaa Kosmetische Zubereitungen
DE19651478A1 (de) * 1996-12-11 1998-06-18 Beiersdorf Ag Lichtschutzzubereitungen mit einem Gehalt an oberflächenaktiven Mono- bzw. Oligoglycerylverbindungen, wasselöslichen UV-Filtersubstanzen und ggf. anorganischen Mikropigmenten
DE19751221A1 (de) * 1997-11-19 1999-05-20 Beiersdorf Ag Verwendung von C¶1¶¶8¶¶-¶¶3¶¶8¶-Alkylhydroxystaroylstearat zur Verstärkung des Lichtschutzfaktors kosmetischer oder dermatologischer Lichtschutzmittel
DE19752564A1 (de) * 1997-11-27 1999-07-01 Henkel Kgaa Pigmentdispersionen
DE19917493A1 (de) * 1999-04-17 2000-10-19 Cognis Deutschland Gmbh Verwendung von Mischungen zur Herstellung von Abschminkmitteln
US7129276B2 (en) * 2001-05-04 2006-10-31 L'oreal S.A. Composition comprising at least one liquid fatty phase structured by at least one semi-crystalline polymer
US7255870B2 (en) 2002-01-24 2007-08-14 L'oreal Composition containing a semicrystalline polymer, uses thereof, and method for making
ES2292834T3 (es) 2002-01-24 2008-03-16 L'oreal Composicion que contiene una mezcla de polimeros semi-cristalinos y un aceite volatil.

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0731413A (ja) * 1993-07-14 1995-02-03 Ajinomoto Co Inc 広域温度安定性乳化組成物
DE4420516C2 (de) * 1994-06-13 1998-10-22 Henkel Kgaa Polyglycerinpolyhydroxystearate

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102005005199A1 (de) * 2005-02-03 2006-08-10 Beiersdorf Ag Verwendung von Alkylglucosiden zum Erzielen oder Verbessern der mikrobiologischen Stabilität von kosmetischen Zubereitungen
JPWO2013069690A1 (ja) * 2011-11-07 2015-04-02 日清オイリオグループ株式会社 洗浄料用組成物及び洗浄料
US9428715B2 (en) 2011-11-07 2016-08-30 The Nisshin Oillio Group, Ltd. Composition for cleansing agent and cleansing agent

Also Published As

Publication number Publication date
DE19524210A1 (de) 1997-01-09
WO1997002002A3 (fr) 1997-02-13

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