WO1995005151A1 - Produits pour les soins de la peau - Google Patents

Produits pour les soins de la peau Download PDF

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Publication number
WO1995005151A1
WO1995005151A1 PCT/EP1994/002575 EP9402575W WO9505151A1 WO 1995005151 A1 WO1995005151 A1 WO 1995005151A1 EP 9402575 W EP9402575 W EP 9402575W WO 9505151 A1 WO9505151 A1 WO 9505151A1
Authority
WO
WIPO (PCT)
Prior art keywords
weight
fatty acid
skin
carbon atoms
acid
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/EP1994/002575
Other languages
German (de)
English (en)
Inventor
Hinrich Möller
Manfred Biermann
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
Priority to EP94926145A priority Critical patent/EP0715514A1/fr
Priority to JP7506710A priority patent/JPH09501660A/ja
Publication of WO1995005151A1 publication Critical patent/WO1995005151A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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
    • A61Q19/08—Anti-ageing preparations

Definitions

  • the invention relates to new skin care products containing fatty acid N-alkylglycosylamides 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, Barcelona, 1992, p.29].
  • 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, Cos .Toil. 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-alkylglycosylamides of the formula (I),
  • R 1 is C0 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 glycosyl radical with 6 to 12 carbon atoms.
  • the invention includes the knowledge that the alkylglycosylamides can be produced on the basis of vegetable fatty acids and sugar, ie without the use of undesirable animal raw materials.
  • the fatty acid N-alkylglycosylamides are basically known substances which are usually obtained by reacting glycoses with longer-chain amines and then acylating with a fatty acid, a fatty acid alkyl ester or preferably a fatty acid chloride in the presence of a base (triethanolamine, Sodium carbonate etc.) can be obtained.
  • a base triethanolamine, Sodium carbonate etc.
  • small amounts of the 0, N-acylation product are also found.
  • Fatty acid N-alkylglycosylamides of the formula (I) are preferably used 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, myristic acid, palmitic acid, palm Oleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid or their technical mixtures and Z stands for a glucosyl residue.
  • Fatty acid N-alkylglucosylamides of the formula (I) which are obtained by amination of glucose with C 2 /14-cocosamine and subsequent acylation with lauric acid chloride or C 2 /14-coconut fatty acid chloride or a corresponding derivative are particularly preferred.
  • Other preferred glycosylamides can be derived from maltose and palatinose.
  • compositions according to the invention can contain the fatty acid N-alkylglycosylamides in amounts of 1 to 30, preferably 2 to 10% by weight, based on the composition.
  • 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 for this purpose are: mineral oils, vegetable oils, silicone oils, fatty acid esters, dialkyl ethers, fatty alcohols and Guerbet alcohols.
  • emulsifiers examples include: 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, for example, alkyl oligoglucosides, fatty alcohol ether sulfates, fatty acid isethionates, taurides and sarcosinates, ether carboxylic acids, sulfosuccinates, protein fat hydrolysates or fatty acid condensates, sulfotriglycerides, short-chain glucamides; Phospholipids, waxes such as bees wax, ozokerite wax, par
  • the fatty acid N-alkylglycosylamides can be mixed with conventional ceramides, pseudoceraids, cholesterol, cholesterol fatty acid esters, fatty acids, triglycerides, cerebrosides, phospholipids and similar substances, liposomes being able to be formed.
  • the fatty acid N-alkylglycosylamides can be mixed with active substance accelerators, in particular with essential oils, such as eucalyptol, menthol and the like.
  • the fatty acid N-alkylglycosylamides can finally also be dissolved in squalene or squalane and optionally 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-alkylglycosylamides 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.
  • the invention therefore furthermore relates to the use of fatty acid N-alkylglycosylamides of the formula (I) as “synthetic barrier lipids” for the production of skin care products in which they are used in amounts of 1 to 30, preferably 2 to 10,% by weight. % - based on the funds - may be included.
  • Typical examples are skin creams, soft creams, Nutrient creams, sunscreen creams, night creams, skin oils, care lotions and body aerosols.
  • N-laurylglucosylamine 180 g (1 mol) of anhydrous glucose were suspended in 300 ml of ethanol in a 2-1 flask and then 184 g (1 mol) of laurylamine were added. The mixture was first stirred at 70 ° C. for 1 h and then at room temperature for 20 h. The precipitated solid was then filtered off, washed with ethanol and ether and dried. The yield of N-laurylglucosylamine was 80% of theory.
  • Example 1 Stearic acid-N-laurylglucosylamide.
  • Example 1 was repeated with 346 g (1 mol) of N-laurylglucosylamine, 303 g (1 mol) of stearic acid chloride and 6 g of triethanolamine. 568 g of stearic acid-N-laurylglucosylamide - 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)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Birds (AREA)
  • Epidemiology (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-alkylglycosylamides 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 glycosyle de 6 à 12 atomes de carbone.
PCT/EP1994/002575 1993-08-12 1994-08-03 Produits pour les soins de la peau Ceased WO1995005151A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP94926145A EP0715514A1 (fr) 1993-08-12 1994-08-03 Produits pour les soins de la peau
JP7506710A JPH09501660A (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
DE19934326958 DE4326958C2 (de) 1993-08-12 1993-08-12 Verwendung von Fettsäure-N-alkylglykosylamiden
DEP4326958.3 1993-08-12

Publications (1)

Publication Number Publication Date
WO1995005151A1 true WO1995005151A1 (fr) 1995-02-23

Family

ID=6494946

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1994/002575 Ceased WO1995005151A1 (fr) 1993-08-12 1994-08-03 Produits pour les soins de la peau

Country Status (4)

Country Link
EP (1) EP0715514A1 (fr)
JP (1) JPH09501660A (fr)
DE (1) DE4326958C2 (fr)
WO (1) WO1995005151A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2725130B1 (fr) * 1994-09-29 1996-10-31 Oreal Compositions cosmetiques contenant un compose lipidique de type ceramide et un peptide a une chaine grasse, et leurs utilisations
US6033652A (en) * 1996-05-15 2000-03-07 Henkel Kommanditgesellschaft Auf Aktien Hair-treatment formulations
JP2006504752A (ja) * 2002-10-15 2006-02-09 ロレアル 乾燥皮膚の治療及び／又は予防における脂肪酸のアミド又は糖とのエステルの使用

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

Also Published As

Publication number Publication date
EP0715514A1 (fr) 1996-06-12
JPH09501660A (ja) 1997-02-18
DE4326958A1 (de) 1995-02-16
DE4326958C2 (de) 1995-07-06

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