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WO1995035088A1 - Emulsions cosmetiques et/ou pharmaceutiques d'huile dans l'eau - Google Patents

Emulsions cosmetiques et/ou pharmaceutiques d'huile dans l'eau Download PDF

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Publication number
WO1995035088A1
WO1995035088A1 PCT/EP1995/002261 EP9502261W WO9535088A1 WO 1995035088 A1 WO1995035088 A1 WO 1995035088A1 EP 9502261 W EP9502261 W EP 9502261W WO 9535088 A1 WO9535088 A1 WO 9535088A1
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WO
WIPO (PCT)
Prior art keywords
hydrogen
alkyl
emulsions
esters
alcohols
Prior art date
Application number
PCT/EP1995/002261
Other languages
German (de)
English (en)
Inventor
Rolf Wachter
Armin Wadle
Peter Busch
Holger Tesmann
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 WO1995035088A1 publication Critical patent/WO1995035088A1/fr

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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
    • A61K8/02—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
    • A61K8/18—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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin

Definitions

  • the invention relates to cosmetic and / or pharmaceutical O / W emulsions containing selected pseudoceramides which are obtained by the phase inversion temperature method, a process for the preparation of the emulsions and their use for the production of skin care products.
  • a balanced water balance in the biogenic bar functions of the individual skin layers plays an important role for the elasticity and appearance of the skin.
  • the bound water content is greatest in the dermis and in the boundary layer of the epidermis near the basement membrane.
  • the elasticity and the state of tension of the skin is decisively shaped by the collagen and elastin fibers in the dermis, the specific conformation of the collagen being achieved by the incorporation of water molecules.
  • Ceramides are lipophilic amides of long-chain fatty acids, which are generally derived from sphingosine or phytosphingosine. This class of endogenous fatty substances has gained considerable importance since they have been recognized in the intercellular space between the corneocytes as key components for the structure of the lipid bilayer, ie the permeability barrier, in the stratum corneum of human skin. Ceramides have molecular weights of significantly less than 1000, so that the external site of a cosmetic formulation makes it possible to reach the site of action. The external application of ceramides leads to the restructuring of the lipid barrier, which can cause the described disorders of the skin function to be counteracted [cf. R.D. Petersen, Cosm.Toil. 107, 45 (1992)].
  • the object of the invention was to provide emulsions with an increased content of pseudoceramides, which are at the same time characterized by improved storage stability and improved skin cosmetic properties.
  • the invention relates to cosmetic and / or pharmaceutical O / W emulsions, obtainable by adding an oil phase containing pseudoceramides of the alkyl succinic acid ester type of the formula (I),
  • R 1 represents an alkyl and / or alkenyl radical with 6 to 22 carbon atoms
  • R 2 represents hydrogen or R 1 and R 3 and R 4 independently of one another represent hydrogen or an alkyl and / or alkenyl radical with 6 to 22 carbons, with the Provided that at most one of these two radicals can be hydrogen, and the sum (n + p) stands for numbers from 1 to 20, emulsified with water in the range above the phase inversion temperature.
  • a particular embodiment of the invention relates to 0/W emulsions which have a pseudoceramides content in the range from 5 to 10 and in particular 7 to 9% by weight.
  • phase inversion temperature method known per se allows the production of stable emulsions with a significantly increased content of selected pseudoceramides.
  • the "PIT concentrates” obtained in this way are further distinguished from commercially available skin care products when applied topically by a reduced transepidermal water loss.
  • the invention further relates to a process for the preparation of cosmetic and / or pharmaceutical O / W emulsions, in which an oil phase containing pseudoceramides of the alkyl succinic acid ester type of the formula (I)
  • ⁇ stands for an alkyl and / or alkenyl radical with 6 to 22 carbon atoms
  • R 2 for hydrogen or R 1 and R ⁇ and R 4 independently of one another for hydrogen or an alkyl and / or alkenyl radical with 6 to 22 carbons , with the Provided that at most one of these two radicals can be hydrogen, and the sum (n + p) stands for numbers from 1 to 20, emulsified with water above the phase inversion temperature.
  • Alkyl succinic acid esters are suitable as pseudoceramides. These substances are known pseudoceramides which can be obtained, for example, according to DE-Al 4238032 (Hen ⁇ kel) by ring opening of alkylsuccinic anhydrides with alcohols and subsequent base-catalyzed reaction with ethylene oxide. If necessary, hardening can follow as a further step.
  • the alkyl succinic acid esters can be present as diesters, but monoesters are preferably used.
  • ethylene oxide groups are inserted into the ester bond or the free carboxyl function is esterified. The insertion reaction proceeds statistically, accordingly the degree of ethoxylation does not allow any conclusion to be drawn about the distribution of the EO groups, but only about the molar ratio used.
  • Typical examples of pseudoceramides which come into consideration in the sense of the invention are addition products of an average of 1 to 20, preferably 2 to 10 and in particular 6 to 8 moles of ethylene oxide with hexostecylsuccinic acid monostearyl ester, hexadecylsuccinic acid distearyl ester, ocotadecylsuccinic acid monopalmitine esters and the like.
  • alkyl succinic acid esters of the formula (I) preference is given to alkyl succinic acid esters of the formula (I) in which R 1 and R 2 are alkyl radicals with 12 to 22 and preferably 16 to 22 carbon atoms, R 3 for alkyl radicals with 16 to 18 carbon atoms, R 4 for hydrogen and the sum (n + m) for numbers from 6 to 8 stands.
  • Typical examples of this are an adduct of an average of 7.6 mol of ethylene oxide onto a hexadecylsuccinic acid monostearyl ester or a hexadecylsuccinic acid monobehenyl ester 7.5 EO adduct.
  • the pseudoceramides are preferably used in concentrations of 5 to 10 and in particular 7 to 9% by weight, based on the emulsion.
  • Suitable oil bodies are:
  • esters of linear C 1 -C 8 fatty acids with branched alcohols in particular 2-ethylhexanol, such as 2-ethylhexyl coconut fatty acid;
  • Esters of linear and / or branched fatty acids with dihydric alcohols and / or Guerbet alcohols such as eg 2-ethylhexyl isostearic acid or 2-octyldodecyl isopalmitate;
  • vegetable oils such as Almond oil, olive oil, sunflower oil and the like;
  • branched primary alcohols e.g. Isostearyl alcohol
  • substituted cyclohexanes such as e.g. Di-n-octylcyclohexane;
  • Guerbet carbonates e.g. Bis-2-octyldodecyl carbonate and / or
  • Dialkyl ethers e.g. Di-n-octyl ether.
  • the oil bodies can be used in amounts of 10 to 80, preferably 20 to 60 and in particular 30 to 50% by weight, based on the emulsion.
  • Suitable emulsifiers are:
  • polyglycerol fatty acid esters such as polyglycerol isostearates, *** polyol polyhydroxycarboxylic acid esters, such as polyglycerol polyricinoleates and / or polyglycerol polyhydroxy stearates, *** sorbitan esters, such as sorbitan mono-, -sesqui-, -bis- or -trilaurate , palmitate, stearate or oleate; *** Polysorbates, such as the adducts of 1 to 40 moles of ethylene oxide with the sorbitan esters mentioned;
  • the emulsifiers can be used in amounts of 1 to 10, preferably 4 to 8% by weight, based on the emulsion.
  • phase inversion temperature method is a known method for the hot emulsification of fatty substances in aqueous systems.
  • Cosmetic emulsions which can be obtained by this method are described, for example, in German patent applications DE-Al 3819193, DE-Al 4010393, DE-Al 4140562, DE-Al 4243272 and DE-Al 4318171 (Henkel).
  • the skin care products can contain minor amounts of other surfactants that are compatible with the other ingredients.
  • Typical examples are fatty alcohol polyglycol ether sulfates, monoglyceride sulfates, ether carboxylic acids, mono- and / or dialkyl sulfosuccinates, fatty acid isethionates, fatty acid desarcosinates, alkyl and fatty acid / taurides. or alkenyl oligoglucosides, alkyl amido betaines and / or protein hydrolyzates or their condensates with fatty acids on an animal or preferably vegetable basis.
  • auxiliaries and additives are fats and waxes, stabilizers, thickeners, biogenic agents, film formers, fragrances, dyes, pearlescent agents, preservatives, UV filters, pigments, electrolytes (eg magnesium sulfate) and pH regulators Consideration.
  • Typical examples of fats are glycerides, waxes which may be used include beeswax, paraffin wax or microwaxes, if appropriate in combination with hydrophilic waxes, for example cetylstearyl alcohol.
  • Metal salts of fatty acids such as magnesium, aluminum and / or zinc stearate can be used as stabilizers.
  • Suitable thickeners are, for example, crosslinked polyacrylic acids and their derivatives, polysaccharides, in particular xanthan gum, GuarrGuar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, and also fatty alcohols, monoglycerides and fatty acids, polyacrylates, polyvinyl alcohol and polyvinyl pyrrolid.
  • Biogenic active substances are understood to mean, for example, plant extracts, protein hydrolyzates and vitamin complexes.
  • Common film formers are, for example, hydrocolloids such as chitosan, microcrystalline chitosan or quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives and similar compounds.
  • Suitable preservatives are, for example, formaldehyde solution, p-hydroxybenzoate or sorbic acid.
  • pearlescent agents are glycol distearic acid esters such as ethylene glycol distearate, but also fatty acids and fatty acid mono- glycolester into consideration.
  • the dyes which can be used are the substances which are suitable and approved for cosmetic purposes, as compiled, for example, in the publication "Cosmetic Dyes” by the Dye Commission of the German Research Foundation, published by Chemie Publishing House, Weinheim, 1984. These dyes are usually used in concentrations of 0.001 to 0.1% by weight, based on the mixture as a whole.
  • the total proportion of auxiliaries and additives can be 1 to 50, preferably 5 to 40% by weight and the non-aqueous proportion (“active substance content”) 20 to 80, preferably 30 to 70% by weight, based on the composition.
  • the cosmetic and / or pharmaceutical O / W emulsions according to the invention with an increased content of pseudoceramides are distinguished by a particular stability and a reduced transepidermal water loss when applied topically to the skin.
  • Another object of the invention therefore relates to the use of the O / W emulsions for the production of skin care products, such as hand creams, nutritional creams, day creams, night creams, moisturizers, hand lotions, sun creams and the like.
  • the O / W emulsions according to the invention from Examples 1 to 3 and Comparative Example VI were prepared by the PIT method, ie above the phase inversion temperature.
  • the comparison emulsions V2 and V3 were prepared below the PIT. Percentages as% by weight (water ad 100% by weight).
  • the emulsions were assessed visually for their distribution and storage stability (2 weeks, 40 ° C.). The results are summarized in Table 1: Table 1 Composition of the O / W emulsions
  • the examples and comparative examples show that finely divided, storage-stable O / W emulsions with a high proportion of pseudoceramide can only be prepared by the PIT method.
  • TEWL transepidermal water loss

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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)
  • Oil, Petroleum & Natural Gas (AREA)
  • Dermatology (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)
  • Medicinal Preparation (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

Abstract

De nouvelles émulsions cosmétiques et/ou pharmaceutiques d'huile dans l'eau sont produites en émulsifiant dans de l'eau à une température supérieure à la température d'inversion des phases une phase huileuse qui contient des pseudocéramides du type des esters d'acide succinique d'alcoyle ayant la formule (I), dans laquelle R1 désigne un résidu alcoyle et/ou alcényle avec 6 à 22 atomes de carbone, R2 désigne hydrogène ou R?1, R3 et R4¿ désignent indépendamment les uns des autres hydrogène ou un résidu alcoyle et/ou alcényle avec 6 à 22 atomes de carbone, à condition qu'au maximum un de ces résidus désigne hydrogène, et que la somme (n+p) soit comprise entre 1 et 20. Ces émulsions sont extrêmement stables même lorsque leur teneur en pseudocéramides est élevée, et réduisent lors de leur application locale la perte d'eau à travers l'épiderme.
PCT/EP1995/002261 1994-06-17 1995-06-12 Emulsions cosmetiques et/ou pharmaceutiques d'huile dans l'eau WO1995035088A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4421208.9 1994-06-17
DE19944421208 DE4421208A1 (de) 1994-06-17 1994-06-17 Kosmetische und/oder pharmazeutische O/W-Emulsionen

Publications (1)

Publication Number Publication Date
WO1995035088A1 true WO1995035088A1 (fr) 1995-12-28

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WO (1) WO1995035088A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2750044A1 (fr) * 1996-06-21 1997-12-26 Oreal Utilisation de derives de l'anhydride succinique dans des compositions de nettoyage de la peau

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19703087C2 (de) * 1997-01-29 1999-04-22 Henkel Kgaa Verwendung von PIT-Emulsionen
DE10108246A1 (de) 2001-02-21 2002-09-19 Gkn Sinter Metals Gmbh Kolben mit Stützstegen für eine Kolben-Zylinder-Anordnung, insbesondere Stoßdämpferkolben

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993011865A1 (fr) * 1991-12-09 1993-06-24 Henkel Kommanditgesellschaft Auf Aktien Procede de preparation d'emulsions d'huile dans l'eau
WO1994010971A1 (fr) * 1992-11-11 1994-05-26 Unilever Plc Composition cosmetique renfermant des esters d'acide succinique

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4238032A1 (de) * 1992-11-11 1994-05-19 Henkel Kgaa Hautkonditionierende Bernsteinsäure-Derivate

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993011865A1 (fr) * 1991-12-09 1993-06-24 Henkel Kommanditgesellschaft Auf Aktien Procede de preparation d'emulsions d'huile dans l'eau
WO1994010971A1 (fr) * 1992-11-11 1994-05-26 Unilever Plc Composition cosmetique renfermant des esters d'acide succinique

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2750044A1 (fr) * 1996-06-21 1997-12-26 Oreal Utilisation de derives de l'anhydride succinique dans des compositions de nettoyage de la peau
EP0813860A1 (fr) * 1996-06-21 1997-12-29 L'oreal Utilisation de dérivés de l'anhydride succinique dans des compositions de nettoyage de la peau
US5993793A (en) * 1996-06-21 1999-11-30 L'oreal Use of succinic anhydride derivatives in skin cleansing compositions

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Publication number Publication date
DE4421208A1 (de) 1995-12-21

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