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WO1995019366A1 - Pseudo-ceramides - Google Patents

Pseudo-ceramides Download PDF

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Publication number
WO1995019366A1
WO1995019366A1 PCT/EP1995/000064 EP9500064W WO9519366A1 WO 1995019366 A1 WO1995019366 A1 WO 1995019366A1 EP 9500064 W EP9500064 W EP 9500064W WO 9519366 A1 WO9519366 A1 WO 9519366A1
Authority
WO
WIPO (PCT)
Prior art keywords
radical
carbon atoms
formula
hydroxyalkyl
pseudoceramides
Prior art date
Application number
PCT/EP1995/000064
Other languages
German (de)
English (en)
Inventor
Manfred Weuthen
Petra Riegels
Rolf Wachter
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 WO1995019366A1 publication Critical patent/WO1995019366A1/fr

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Classifications

    • 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
    • C07H15/06—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical being a hydroxyalkyl group esterified by a fatty acid
    • 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
    • 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 pseudoceramides obtainable by esterification or transesterification of hydroxyalkyl oligoglycosides with fatty acids or fatty acid esters in the presence of alkaline catalysts, a process for the preparation of the pseudoceramides, skin care products containing the pseudoceramides and the use of the pseudoceramides for the preparation 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 dermis and in the boundary layer of the epidermis near the basement membrane.
  • the skin elasticity is decisively shaped by the collagen fibrils in the dermis, the specific conformation of the collagen being achieved by the incorporation of water molecules.
  • SC stratum corneum
  • 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 restoration of the lipid barrier, which can cause the described disorders of the skin function to be counteracted [cf. R.D. Petersen, Cosm. oil. 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
  • 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 produce the new pseudoceramides based on non-animal raw materials.
  • the invention relates to pseudoceramides, obtainable by reacting hydroxyalkyl oligoglycosides of the formula (I)
  • R 1 stands for a hydroxyalkyl radical with 2 to 18 carbon atoms
  • G for a sugar radical with 5 or 6 carbon atoms and p for numbers from 1 to 10
  • acidic or basic catalysts with fatty acids or fatty acid - reesters of formula (II) in which R 1 stands for a hydroxyalkyl radical with 2 to 18 carbon atoms, G for a sugar radical with 5 or 6 carbon atoms and p for numbers from 1 to 10, in the presence of acidic or basic catalysts with fatty acids or fatty acid - reesters of formula (II),
  • R ⁇ CO represents a linear or branched acyl radical having 6 to 22 carbon atoms and 0 and / or 1, 2 or 3 double bonds and R 3 represents hydrogen or an alkyl radical having 1 to 4 carbon atoms, esterified or transesterified.
  • pseudoceramides are particularly preferred, obtainable by transesterification of hydroxyalkyl oligoglycosides of the formula (1) / in which R * stands for a 1-hydroxydecyl residue, G for a glucose residue and p for numbers from 1 to 3, with fatty acid esters of Formula (II) in which R ⁇ CO represents an acyl radical having 12 to 18 carbon atoms and R 3 represents a methyl radical.
  • the invention further relates to a process for the preparation of pseudoceramides, in which H droxyalkyl oligoglycosides of the formula (I) #
  • R 1 represents a hydroxyalkyl radical having 2 to 18 carbon atoms
  • G represents a sugar radical having 5 or 6 carbon atoms
  • p represents numbers from 1 to 10
  • acidic rer or basic catalysts with fatty acids or fatty acid esters of the formula (II) in which R 1 represents a hydroxyalkyl radical having 2 to 18 carbon atoms, G represents a sugar radical having 5 or 6 carbon atoms and p represents numbers from 1 to 10, in the presence of acidic rer or basic catalysts with fatty acids or fatty acid esters of the formula (II),
  • R 2 C0 represents a linear or branched acyl radical having 6 to 22 carbon atoms and 0 and / or 1, 2 or 3 double bonds and R 3 represents hydrogen or an alkyl radical having 1 to 4 carbon atoms, esterified or transesterified.
  • Hydroxyalkyl oligoglycosides are known substances which can be obtained by the relevant processes for the preparation of alkyl oligoglycosides. Representative of the extensive literature, reference is made here to the publications EP-Al-0 301 298 and WO 90/3977.
  • the hydroxyalkyl oligoglycosides can be derived from aldoses or ketoses with 5 or 6 carbon atoms, preferably glucose.
  • the preferred hydroxyalkyl oligoglycosides are thus hydroxyalkyl oligoglucosides.
  • the hydroxyalkyl radical can be derived from dihydroxy compounds having 2 to 18, preferably 2 to 10, carbon atoms, especially won alpha, omega-diols.
  • Typical examples are ethylene glycol, propylene glycol, 1,2-butanediol, 1,4-butanediol and in particular 1,10-decanediol.
  • R 1 is a 1-hydroxydecyl radical
  • G is a glucose radical
  • p is a number from 1 to 3.
  • the hydroxyalkyl oligoglycosides have further primary and secondary OH functions in the glycoside residue, which are in principle accessible to esterification or transesterification.
  • Analytical investigations by the applicant show that the primary hydroxyl groups in the glycoside residue react first, followed by the OH function in the alkyl chain; The secondary hydroxyl groups in the sugar body are the most difficult to esterify / transesterify.
  • Fatty acids with 6 to 22 carbon atoms are suitable for the esterification or transesterification.
  • Typical examples are caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isosteric acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, elaleostearic acid, gadic acid and arachic acid, arachic acid as well as their technical mixtures, which occur, for example, in the pressure splitting of natural fats and oils, in the reduction of aldehydes from Roelen's oxosynthesis or in the dimerization of unsaturated fatty acids.
  • esters with lower alcohols having 1 to 4 carbon atoms are also suitable as starting materials.
  • the hydroxyalkyl oligoglycosides and the fatty acids or fatty acid esters can usually be used in a molar ratio of 1: 1 to 1:10, preferably 1: 2 to 1: 5.
  • the use of fatty acid methyl esters as transesterification components is preferred, inter alia, since the degree of ester substitution and thus also the hydrophilicity of the pseudoceramides can be adjusted in a simple manner by removing the methanol released during the transesterification from the reaction equilibrium.
  • the esterification or transesterification takes place in the presence of acidic or basic catalysts.
  • Suitable acidic catalysts are preferably carboxylic acids. If sulfonic acids are used as catalysts, transacetalizations and polymerization reactions can occur.
  • a transesterification is therefore preferably carried out in the presence of basic catalysts, which are preferably selected from the group formed by alkali and / or alkaline earth metal oxides, hydroxides, carbonates, bicarbonates and / or C 1 -C 4 -alcoholates . Typical examples are sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, magnesium oxide and sodium methoxide.
  • the basic catalysts can usually be used in amounts of 1 to 10, preferably 2 to 5% by weight, based on the starting materials.
  • the esterification or transesterification can be carried out in a manner known per se at temperatures in the range from 100 to 180 ° C.
  • fatty acid methyl esters When fatty acid methyl esters are used, it is advisable to continuously remove the methanol released from the reaction equilibrium and, after the reaction has ended, to neutralize basic catalyst, for example lactic acid or phosphoric acid, by adding an acid. Excess fatty acid or unreacted fatty acid methyl ester can then be distilled off in vacuo.
  • the invention further relates to skin care compositions containing pseudoceramides of the formula (I).
  • the agents according to the invention can contain the pseudoceramides in amounts of 1 to 30, preferably 2 to 10% by weight, based on the agents, and both as “water-in-oil” and “oil-in” Water "emulsions are present; It can also contain other customary 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 which can be used are: alkyl and hydroxyalkyl oligoglycosides, 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, for example, p-hydroxybenzoic acid ester; Antioxidants, such as butylated hydroxytoluene, tocopherol; Humectants, such as glycerol, 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 fatty alcohol ether sulfates, fatty acid isethionates, taurides and sarcosinates, ether carboxylic acids, ren, sulfosuccinates, protein hydrolyzates or fatty acid condensates, sulfotriglycerides, short-chain glucamides; Phospholipids, waxes such as beeswax, ozokerite wax, paraffin wax; Plant extract
  • the pseudoceramides can be mixed with conventional ceramides, further pseudo-ceramides, cholesterol, cholesterol fatty acid esters, fatty acids, triglycerides, cerebrosides, phospholipids and similar substances, whereby liposomes can be formed.
  • the pseudoceramides can be mixed with active substance accelerators, in particular with essential oils, such as, for example, eucalyptol, menthol and the like.
  • the pseudoceramides can finally also be dissolved in squalene or squalane and,
  • pseudoceramides 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 pseudoceramides 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 funds - may be included.
  • Typical examples are skin creams, soft creams, nutritional creams, sunscreen creams, night creams, skin oils, care lotions and body aerosols.
  • Phosphoric acid adjusted to a pH of 6.4. After the excess methyl laurate (140 ° C., 20 mbar) had been removed by distillation, 355 g of the 1, 10-decanediol glucoside dilaurate were obtained as an ivory-colored solid; the residual unreacted glucoside content was 5% by weight.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dermatology (AREA)
  • Organic Chemistry (AREA)
  • Molecular Biology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Cosmetics (AREA)
  • Saccharide Compounds (AREA)

Abstract

L'invention concerne de nouveaux pseudo-céramides de la formule (I) que l'on obtient par estérification ou transestérification d'hydroxyalkyloligoglycosides de la formule (I): R1-O-[G]¿p?, dans laquelle R?1¿ désigne un reste hydroxyalkyle ayant entre 2 et 18 atomes de carbone, G désigne un reste saccharose ayant 5 ou 6 atomes de carbone et p vaut entre 1 et 10, en présence de catalyseurs acides ou basiques avec des acides gras ou des esters d'acides gras de la formule (II): R2CO-OR3, dans laquelle R2CO désigne un reste acyle linéaire ou ramifié ayant entre 6 et 22 atomes de carbone et 0 et/ou 1, 2 ou 3 liaisons doubles et R3 désigne hydrogène ou un reste alkyle ayant entre 1 et 4 atomes de carbone. Ces substances s'utilisent comme 'lipides à effet de barrière synthétique' dans la préparation d'agents pour le soin de la peau.
PCT/EP1995/000064 1994-01-17 1995-01-09 Pseudo-ceramides WO1995019366A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4401102.4 1994-01-17
DE19944401102 DE4401102A1 (de) 1994-01-17 1994-01-17 Pseudoceramide

Publications (1)

Publication Number Publication Date
WO1995019366A1 true WO1995019366A1 (fr) 1995-07-20

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PCT/EP1995/000064 WO1995019366A1 (fr) 1994-01-17 1995-01-09 Pseudo-ceramides

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DE (1) DE4401102A1 (fr)
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000247992A (ja) * 1999-02-25 2000-09-12 Tatsuya Yamagata 新規糖鎖プライマー
FR2831539A1 (fr) * 2001-10-25 2003-05-02 Seppic Sa Utilisation d'alkylpolyglycosides comme agents emulsionnants pour la preparation d'emulsion huile-dans eau contenant des charges ou pigments mineraux, et emulsions huile-dans-eau contenant de tels alkylpolyglycosides

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992013866A1 (fr) * 1991-02-07 1992-08-20 Grillo-Werke Ag Derives d'alcools de disaccharide, leur procede de production et leur utilisation
EP0512270A2 (fr) * 1991-04-08 1992-11-11 Kao Corporation Composition cosmétique
JPH05222083A (ja) * 1992-02-03 1993-08-31 Nippon Koonsutaac Kk グリコシド脂肪酸エステル及びその製造方法

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DE3772749D1 (de) * 1986-08-11 1991-10-10 Baxter Int Waschsystem von blutzellen und verfahren.
JPH0686373B2 (ja) * 1987-02-05 1994-11-02 花王株式会社 化粧料
DE3723826A1 (de) * 1987-07-18 1989-01-26 Henkel Kgaa Verfahren zur herstellung von alkylglykosiden
DE3889084T2 (de) * 1987-12-11 1994-08-11 Unilever Nv Verfahren zur Herstellung von Polyol-Fettsäureester.
AU4216089A (en) * 1988-08-12 1990-03-05 Joel E. Bernstein Method and composition for treating and preventing dry skin disorders
DE3833780A1 (de) * 1988-10-05 1990-04-12 Henkel Kgaa Verfahren zur direkten herstellung von alkylglykosiden
GB9009793D0 (en) * 1990-05-01 1990-06-20 Unilever Plc Cosmetic composition
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Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992013866A1 (fr) * 1991-02-07 1992-08-20 Grillo-Werke Ag Derives d'alcools de disaccharide, leur procede de production et leur utilisation
EP0512270A2 (fr) * 1991-04-08 1992-11-11 Kao Corporation Composition cosmétique
JPH05222083A (ja) * 1992-02-03 1993-08-31 Nippon Koonsutaac Kk グリコシド脂肪酸エステル及びその製造方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 9339, Derwent World Patents Index; Class D21, AN 93-309187 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000247992A (ja) * 1999-02-25 2000-09-12 Tatsuya Yamagata 新規糖鎖プライマー
FR2831539A1 (fr) * 2001-10-25 2003-05-02 Seppic Sa Utilisation d'alkylpolyglycosides comme agents emulsionnants pour la preparation d'emulsion huile-dans eau contenant des charges ou pigments mineraux, et emulsions huile-dans-eau contenant de tels alkylpolyglycosides
WO2003035657A3 (fr) * 2001-10-25 2004-01-22 Explotation De Produits Pour L Utilisation d'alkylpolyglycosides comme agents emulsionnants
JP2005514340A (ja) * 2001-10-25 2005-05-19 ソシエテ・デクスプロワタシオン・デ・プロデュイ・プール・レ・アンデュストリー・シミック・セピック 無機フィラーまたは顔料を含む水中油型エマルジョンの調製のための乳化剤としてのアルキルポリグリコシドの使用、およびそのようなアルキルポリグリコシドを含む水中油型エマルジョン

Also Published As

Publication number Publication date
DE4401102A1 (de) 1995-07-20

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