WO1995005152A1 - Produits pour les soins de la peau - Google Patents

Produits pour les soins de la peau Download PDF

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Publication number
WO1995005152A1
WO1995005152A1 PCT/EP1994/002576 EP9402576W WO9505152A1 WO 1995005152 A1 WO1995005152 A1 WO 1995005152A1 EP 9402576 W EP9402576 W EP 9402576W WO 9505152 A1 WO9505152 A1 WO 9505152A1
Authority
WO
WIPO (PCT)
Prior art keywords
weight
fatty acid
carbon atoms
skin
acid
Prior art date
Application number
PCT/EP1994/002576
Other languages
German (de)
English (en)
Inventor
Hinrich Möller
Manfred Biermann
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 EP94925426A priority Critical patent/EP0713384A1/fr
Priority to JP7506711A priority patent/JPH10507999A/ja
Publication of WO1995005152A1 publication Critical patent/WO1995005152A1/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
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/68—Sphingolipids, e.g. ceramides, cerebrosides, gangliosides
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • 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
    • A61Q19/08—Anti-ageing preparations

Definitions

  • the invention relates to new skin care products containing fatty acid N-alkylpolyhydroxyalkylamides and their use as "synthetic barrier lipids" for the production of skin care products.
  • a balanced water balance in the individual skin layers plays an important role for the elasticity and the appearance of the skin.
  • the content of bound water is greatest in the Dennis and in the boundary layer of the epidermis near the basement membrane.
  • the skin elasticity is decisively shaped by the collagen fibrils in the Dennis, the specific conformation of the collagen being achieved by the incorporation of water molecules.
  • Destruction of the lipid barrier in the stratum corneum (SC), for example by surfactants leads to an increase in transepidermal water loss, which in turn disturbs the aqueous environment of the cells. Since the water bound in the deeper layers of the skin is only supplied via the body fluids and not from the outside it becomes clear that maintaining the barrier function of the stratum corneum is essential for the overall condition of the skin [cf. SEFriberg et al, CR 23rd CED Congress,
  • 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, together with the corneocytes, have been recognized as key components for the construction 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 restoration of the lipid barrier, which can cause the described disorders of the skin function to be counteracted [cf. R.D.Petersen, Cosm.Toll. 107, 45 (1992)].
  • R a stands for hydrogen or an unsaturated fatty acyl radical
  • z for numbers from 7 to 49
  • A for a hydroxyalkyl
  • Z for a sugar or phosphate radical
  • moisture-regulating substances include also considered long-chain, ethoxylated succinic acid derivatives.
  • the object of the invention was therefore to develop new high-performance ceramide-analog structures which are distinguished by the simplest possible synthesis. Another task was to manufacture the new pseudoceramides based on non-animal raw materials.
  • the invention relates to skin care products containing fatty acid N-alkylpolyhydroxyalkylamides of the formula (I),
  • R- ⁇ CO for an aliphatic acyl radical with 6 to 22 carbon atoms
  • R *** - for an alkyl or hydroxyalkyl radical with 4 to 22 carbon atoms
  • [Z] for a linear or branched polyhydroxyalkyl radical having 3 to 12 carbon atoms and 3 to 10 hydroxyl groups.
  • the fatty acid N-alkylpolyhydroxyalkylamides to be used in accordance with the invention strengthen the natural barrier function of the skin, strengthen the skin and protect it from drying out.
  • the substances are based on the natural skin lipids, dermatologically and ecotoxicologically harmless and can be incorporated homogeneously into the oil phase of cosmetic products. They are white or ivory-colored, odorless, hydrolysis-resistant in the range of the skin pH value and color-stable against atmospheric oxygen.
  • the invention includes the knowledge that the polyhydroxyalkylamides can be produced on the basis of vegetable fatty acids and sugar, that is to say without the undesirable use of animal raw materials.
  • the fatty acid N-alkylpolyhydroxyalkylamides are basically known substances which are usually obtained by reductive amination of a reducing sugar with a longer chain A in or an alkanolamine and subsequent acylation with a fatty acid, a fatty acid alkyl ester or preferably a fatty acid chloride in the presence a base (triethanolamine, sodium carbonate, etc.) can be obtained.
  • a base triethanolamine, sodium carbonate, etc.
  • the polyhydroxy fatty acid amides are preferably derived from reducing sugars having 5 or 6 carbon atoms, in particular from glucose.
  • the preferred fatty acid amides are therefore fatty acid N-alkylglucamides as represented by the formula (II):
  • Preferably used as polyhydroxy fatty acid amides are fatty acid N-alkylglucamides of the formula (II) in which R 2 for an alkyl radical having 8 to 18, in particular 12 to 18 carbon atoms and R **** CO for the acyl radical of lauric acid, myri- Stic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid or their technical mixtures.
  • R 2 for an alkyl radical having 8 to 18, in particular 12 to 18 carbon atoms
  • R **** CO for the acyl radical of lauric acid, myri- Stic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid or their technical
  • fatty acid-N-alkyl For ⁇ mel (II) * k by reductive amination of glucose with Ci2 / 14 * Ko osam rechlorid i n d un subsequent acylation with Laurin Text- or Ci2 / ⁇ 14 ° k ° s fatty acid l 1 l or i c i or a corresponding derivative can be obtained.
  • Further preferred fatty acid N-alkyl polyhydroxyalkylamides can be derived from malose and palatinose.
  • the agents according to the invention can contain the fatty acid-N-alkyl-polyhydroxyalkylamides in amounts of 1 to 30, preferably 2 to 10% by weight, based on the agents.
  • the agents according to the invention can be present as "water-in-oil” or “oil-in-water” emulsions and can contain further conventional auxiliaries and additives in amounts of 5 to 95, preferably 10 to 80,% by weight. Furthermore, the formulations can contain water in an amount of up to 99% by weight, preferably 5 to 80% by weight.
  • Suitable carrier oils include, for example: mineral oils, vegetable oils, silicone oils, fatty acid esters, dialkyl ethers, fatty alcohols and Guerbet alcohols.
  • emulsifiers which can be used are: sorbitan esters, monoglycerides, polysorbates, polyethylene glycol mono / difatty acid esters, highly ethoxylated fatty acid esters and high molecular weight silicone compounds, such as dimethylpolysiloxanes with an average molecular weight of 10,000 to 50,000.
  • additives can be: preservatives, such as p-hydroxybenzoic acid ester; Antioxidants, such as butylhydroxytoluene, tocopherol; Humectants, such as glycerin, sorbitol, 2-pyrrolidine-5-carboxylate, dibutyl phthalate, gelatin, polyglycols with an average molecular weight of 200 to 600; Buffers such as lactic acid / TEA or lactic acid / NaOH; mild surfactants such as alkyl oligoglucosides, fatty alcohol ether sulfates, fatty acid isethionates, taurides and sarcosinates, ether carboxylic acids, sulfosuccinates, protein hy- drolysates or fatty acid condensates, sulfotriglycerides, short-chain glucamides; Phospholipids, waxes such as bees wax, ozokerite wax, par
  • the fatty acid N-alkylpolyhydroxyalkylamides can be mixed with conventional ceramides, pseudoceramides, cholesterol, cholesterol fatty acid esters, fatty acids, triglycerides, cerebrosides, phospholipids and similar substances, liposomes being able to form.
  • the fatty acid N-alkylpolyhydroxyalkylamides can be mixed with active substance accelerators, in particular with essential oils, such as eucalyptol, menthol and the like.
  • the fatty acid N-alkylpolyhydroxyalkylamides can finally also be dissolved in squalene or squalane and, if appropriate, formulated with the other ingredients mentioned together with volatile or non-volatile silicone compounds as anhydrous or almost anhydrous single-phase systems.
  • the fatty acid N-alkylpolyhydroxyalkylamides to be used as "synthetic barrier lipids" in the sense of the invention strengthen the natural barrier function of the skin against external stimuli. They improve the firmness, suppleness and elasticity of the skin, increase the moisture content and protect the skin from drying out; at the same time, the finest wrinkles are smoothed out.
  • Another object of the invention therefore relates to the use of fatty acid N-alkylpolyhydroxyalkylamides of the formula (I) as "synthetic barrier lipids" for the production of skin care products in which they are present in amounts of 1 to 30, preferably 2 to 10,% by weight. % - based on the means - may be included. Typical examples are skin creams, soft creams, nutrient creams, sunscreen creams, night creams, skin oils, care lotions and body aerosols.
  • N-I_au ____ ylglucamine 180 g (1 mol) of anhydrous glucose, 184 g (1 mol) of laurylamine and 70 g of Raney nickel were suspended in 2 1 aqueous ethanol (60% strength) in a 5-1 steel autoclave. The mixture was then kept at 50 ° C. for 2 h and then at 70 ° C. for 3 h, the pressure being 180 bar. After cooling, the pressure reactor was depressurized and the reaction product was filtered through a hot steam filter. The filtrate was cooled, the N-laurylglucamine being precipitated as a fine powder. The yield was 60% of theory.
  • Example 1 Stearic acid-N-laurylglucamide.
  • Example 1 was repeated with 347 g (1 mol) of N-laurylglucamine, 303 g (1 mol) of stearic acid chloride and 6 g of triethanolamine. 570 g of stearic acid-N-laurylglucamide - corresponding to 90% of theory - were obtained.
  • Lauric acid N-stearyl glucamide Example 1 was repeated with 431 g (1 mol) of N-stearylglucamine, 219 g (1 mol) of lauric acid chloride and 6 g of triethanolamine. 568 g of lauric acid-N-stearylglucamide - corresponding to 90% of theory - were obtained.
  • Paraffin oil low viscosity ... 4.0% by weight
  • Paraffin oil viscous ... 4.0% by weight
  • Paraffin oil low viscosity ... 4.0% by weight
  • Paraffin oil viscous ... 4.0% by weight
  • Sorbitan monolaurate 2.5% by weight
  • Paraffin oil viscous ... 8.0% by weight
  • cetyl stearyl isononanoate glycerol mono / dipalmitate / stearate, PEG 20 glycerol monostearate, cetyl stearyl alcohol, PEG 20 cetyl stearyl ether and cetyl palmitate;

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Cosmetics (AREA)

Abstract

L'invention a pour objet de nouveaux produits pour les soins de la peau, renfermant, comme lipides d'une barrière lipidique synthétique, des N-alkylpolyhydroxyalkylamides d'acide gras de formule (I), dans laquelle R1CO désigne un reste acyle aliphatique de 6 à 22 atomes de carbone, R2 désigne un reste alkyle ou hydroxyalkyle de 4 à 22 atomes de carbone, et [Z] désigne un reste polyhydroxyalkyle linéaire ou ramifié de 3 à 12 atomes de carbone et avec 3 à 10 groupes hydroxyle.
PCT/EP1994/002576 1993-08-12 1994-08-03 Produits pour les soins de la peau WO1995005152A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP94925426A EP0713384A1 (fr) 1993-08-12 1994-08-03 Produits pour les soins de la peau
JP7506711A JPH10507999A (ja) 1993-08-12 1994-08-03 スキンケア製剤

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4326959.1 1993-08-12
DE19934326959 DE4326959C2 (de) 1993-08-12 1993-08-12 Verwendung von Fettsäure-N-alkylpolyhydroxyalkylamiden

Publications (1)

Publication Number Publication Date
WO1995005152A1 true WO1995005152A1 (fr) 1995-02-23

Family

ID=6494947

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1994/002576 WO1995005152A1 (fr) 1993-08-12 1994-08-03 Produits pour les soins de la peau

Country Status (4)

Country Link
EP (1) EP0713384A1 (fr)
JP (1) JPH10507999A (fr)
DE (1) DE4326959C2 (fr)
WO (1) WO1995005152A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2757853A1 (fr) * 1996-12-26 1998-07-03 Pacific Corp Composes de type ceramide, procede pour leur preparation, et composition cosmetique les contenant
EP3603634A1 (fr) 2004-05-18 2020-02-05 Novartis AG Composition pharmaceutique comprenant du glycopyrrolate et un agoniste du récepteur beta2 adrénergique

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19507531C2 (de) * 1995-03-03 1998-07-09 Henkel Kgaa Verwendung von Fettsäure-N-alkylpolyhydroxyalkylamiden
TW453881B (en) * 1995-10-16 2001-09-11 Kao Corp Cosmetic composition comprising amide derivatives
DE19544710C2 (de) * 1995-11-30 1998-11-26 Henkel Kgaa Verdickungsmittel
DE10018812A1 (de) 2000-04-15 2001-10-25 Cognis Deutschland Gmbh Verfahren zur Herstellung von nichtionischen Tensidgranulaten
DE102005025933B3 (de) * 2005-06-06 2006-07-13 Centrotherm Photovoltaics Gmbh + Co. Kg Dotiergermisch für die Dotierung von Halbleitern

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB745036A (en) * 1953-01-06 1956-02-15 Atlas Powder Co Improvements in or relating to heterocyclic amides and carboxylic esters thereof
WO1983004412A1 (fr) * 1982-06-11 1983-12-22 National Research Development Corporation Composes amphipathiques
EP0285768A1 (fr) * 1987-04-08 1988-10-12 Hüls Aktiengesellschaft Utilisation de N-polyhydroxyalkyl d'amides d'acides gras comme agents épaississants pour systèmes tensio-actifs liquides aqueux
EP0422508A2 (fr) * 1989-10-09 1991-04-17 Kao Corporation Composition de détergent liquide
WO1992005764A1 (fr) * 1990-09-28 1992-04-16 The Procter & Gamble Company Compositions de shampooing ameliorees
WO1992019587A1 (fr) * 1991-05-02 1992-11-12 Berol Nobel Ab Procede de production d'un melange de produits amides, melange de produits amides et son emploi

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2016962A (en) * 1932-09-27 1935-10-08 Du Pont Process for producing glucamines and related products
US1985424A (en) * 1933-03-23 1934-12-25 Ici Ltd Alkylene-oxide derivatives of polyhydroxyalkyl-alkylamides
US2703798A (en) * 1950-05-25 1955-03-08 Commercial Solvents Corp Detergents from nu-monoalkyl-glucamines
DE1619087A1 (de) * 1967-08-14 1969-10-02 Henkel & Cie Gmbh Als Textilwaschmittel brauchbare Tensidkombinationen sowie diese enthaltende Wasch- oder Waschhilfsmittel

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB745036A (en) * 1953-01-06 1956-02-15 Atlas Powder Co Improvements in or relating to heterocyclic amides and carboxylic esters thereof
WO1983004412A1 (fr) * 1982-06-11 1983-12-22 National Research Development Corporation Composes amphipathiques
EP0285768A1 (fr) * 1987-04-08 1988-10-12 Hüls Aktiengesellschaft Utilisation de N-polyhydroxyalkyl d'amides d'acides gras comme agents épaississants pour systèmes tensio-actifs liquides aqueux
EP0422508A2 (fr) * 1989-10-09 1991-04-17 Kao Corporation Composition de détergent liquide
WO1992005764A1 (fr) * 1990-09-28 1992-04-16 The Procter & Gamble Company Compositions de shampooing ameliorees
WO1992019587A1 (fr) * 1991-05-02 1992-11-12 Berol Nobel Ab Procede de production d'un melange de produits amides, melange de produits amides et son emploi

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP0713384A1 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2757853A1 (fr) * 1996-12-26 1998-07-03 Pacific Corp Composes de type ceramide, procede pour leur preparation, et composition cosmetique les contenant
EP3603634A1 (fr) 2004-05-18 2020-02-05 Novartis AG Composition pharmaceutique comprenant du glycopyrrolate et un agoniste du récepteur beta2 adrénergique

Also Published As

Publication number Publication date
DE4326959C2 (de) 1995-07-06
JPH10507999A (ja) 1998-08-04
DE4326959A1 (de) 1995-02-16
EP0713384A1 (fr) 1996-05-29

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