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WO1995021181A1 - Pseudoceramides - Google Patents

Pseudoceramides Download PDF

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Publication number
WO1995021181A1
WO1995021181A1 PCT/EP1995/000229 EP9500229W WO9521181A1 WO 1995021181 A1 WO1995021181 A1 WO 1995021181A1 EP 9500229 W EP9500229 W EP 9500229W WO 9521181 A1 WO9521181 A1 WO 9521181A1
Authority
WO
WIPO (PCT)
Prior art keywords
radical
carbon atoms
alkyl
formula
pseudoceramides
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/EP1995/000229
Other languages
German (de)
English (en)
Inventor
Hinrich Möller
Rolf Wachter
Peter Busch
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 WO1995021181A1 publication Critical patent/WO1995021181A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • C07H13/06—Fatty acids
    • 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 acylation of linear alkyl and / or alkenyl compounds with dicarboxylic acid anhydrides, subsequent conversion of the acylation products into the acid chlorides and condensation with amine compounds, a process for the preparation of the pseudoceramides, skin care products with a content of pseudoceramides and the use of pseudoceramides 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 amount of bound water is greatest in the dermis and in the boundary layer of the epider 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.
  • Destruction of the lipid barrier in the stratum corneum (SC), for example by surfactants leads to an increase in transepidermal water loss, which disturbs the aqueous environment of the cells. Since the water bound in the deeper layers of the skin can only be supplied through the body fluid via vessels, but 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 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.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
  • 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 of the formula (I)
  • R 1 is a linear alkyl and / or alkenyl radical having 6 to 30 carbon atoms
  • R 2 is hydrogen or an optionally hydroxyl-substituted alkyl radical having 1 to 30 carbon atoms
  • R3 is an oligohydroxyalkyl radical having 4 to 12 carbon atoms and 3 to 10 hydroxyl groups or one Glycosyl radical
  • X for a linear or branched alkylene radical with 1 to 6 carbon atoms
  • Y for oxygen, sulfur or an NR ⁇ radical
  • R 4 for hydrogen or an alkyl radical with 1 to 30 carbon atoms.
  • the pseudoceramides 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 modeled on the natural skin lipids, are dermatologically and ecotoxicologically harmless and can be incorporated homogeneously into the oil phase of cosmetic products. They are colored white or ivory-like, odor-free, hydrolysis-resistant in the area of the skin pH and color-stable against atmospheric oxygen.
  • the invention includes the knowledge that the pseudoceramides can be produced on the basis of vegetable fatty alcohols and sugar, ie without the use of undesirable animal raw materials.
  • pseudoceramides of the formula (I) in which R 1 for an alkyl and / or alkenyl radical with 16 to 18 carbon atoms, R 2 for an alkyl or alkenyl radical with 12 to 22 carbon atoms, R 3 for a polyhydroxyalkyl radical 6 carbon atoms and 5 hydroxyl groups or a glucosyl radical, X is an ethylene group and Y is oxygen.
  • the invention further relates to a process for the preparation of pseudoceramides of the formula (I)
  • R 2 and R 3 in turn have the meanings given above.
  • Typical examples of alcohols are the group of fatty alcohols having 6 to 30 carbon atoms.
  • Capron alcohol, caprylic alcohol, capric alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, oleyl alcohol, elaidyl alcohol, linoleol alcohol alcohol, linoleyl alcohol alcohol, are exemplified , Elaeostearyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol and erucyl alcohol and their technical mixtures as are obtainable, for example, by high-pressure hydrogenation of technical methyl ester fractions.
  • Particularly preferred starting materials are fatty alcohols with 16 to 24 carbon atoms and 0 and / or 1 double bond, such as technical grade fatty alcohol.
  • Typical examples of examples of thiols are the sulfur analogs of the above-mentioned fatty alcohols.
  • amines are octylamine, decylamine, dodecylamine, tetradecylamine, hexadecylamine, octadecylamine, oleylamine, eicosylamine, docosylamine, didodecylamine, dioctadecylamine, methyloctadecylamine, docosyloctadecylamine and docosylamine and docosylamine and their docosylamine.
  • the use of amines with 16 to 18 carbon atoms and 0 and 1 double bond is also particularly preferred.
  • dicarboxylic acid anhydrides examples include succinic anhydride, maleic anhydride, glutaric anhydride, phthalic anhydride and oxidic acetic anhydride.
  • Dicarboxylic acid anhydrides of the formula (III) are preferably used in which X represents an alkylene group having 2 to 4 carbon atoms.
  • linear alkyl and / or alkenyl compounds and the dicarboxylic acid anhydrides can usually be used in a molar ratio of 1: 0.9 to 1: 1.1.
  • the free carboxyl group of the acylation products must first be converted into the acid chloride in a manner known per se.
  • Phosphorus trichloride or thionyl chloride are preferably used as chlorine compounds.
  • the acylation products and the chlorine compounds can usually be used in a molar ratio of 1: 0.4 to 1: 2.5.
  • the chlorination is preferably carried out at -10 to 50 ° C. in the absence of water, for example gasoline fractions, toluene, ethyl acetate, tert. Butyl methyl ether or tetrahydrofuran.
  • the acylation products can be reacted with chlorocarbonic acid alkyl esters in an inert solvent to give the mixed anhydrides.
  • the reaction preferably takes place in the presence of an acid scavenger such as triethylamine, tributylamine or sodium or potassium carbonate, the reactants being used in approximately molar amounts at temperatures from -10 to 50, preferably 0 to 10 ° C. After the reaction, it is advisable to filter off the salts formed.
  • an acid scavenger such as triethylamine, tributylamine or sodium or potassium carbonate
  • Suitable polyhydroxyalkalyamines which are reacted with the acid chlorides of the acylation products are N-alkylsorbitylamines and in particular N-alkylglucosylamine of the formula (V)
  • R 2 preferably represents an alkyl radical having 12 to 22 and in particular 16 to 18 carbon atoms.
  • N-alkylglucamines of the formula (VI) are used
  • R 2 preferably represents an alkyl radical having 12 to 22 and in particular 16 to 18 carbon atoms.
  • the N-alkyl glucamines are usually prepared by reductive amination of glucose with fatty amines.
  • the glucosylamines and the glucamines can also be derived, for example, from maltose, fructose or palatinose.
  • Also suitable as further polyhydroxyalkylamines are methylol-substituted alkanolamines, for example 2,2-bis (hydroxymethyl) -2-aminoethanol and 2,2-bis (hydroxymethyl) -3-aminopropanol.
  • the acid chlorides or mixed anhydrides of the acylation products and the polyhydroxyalkylamines and sorbityl or glucosylamines can usually be used in a molar ratio of 1: 0.8 to 1: 2.0.
  • the condensation reaction is preferably carried out at temperatures in the range from 20 to 50 ° C. in the presence of alkaline catalysts, the reaction times typically being 1 to 10 hours.
  • Soda, potash or tertiary araine such as triethylamine can be used as acid scavengers, for example tetrahydrofuran is recommended as a solvent.
  • Another advantageous embodiment consists of working in non-water-miscible solvents and adding the acid scavenger in aqueous solution.
  • the products can then be purified by recrystallization, for example from lower alcohols or column chromatography.
  • recrystallization for example from lower alcohols or column chromatography.
  • the condensation of amine compounds with acid chlorides is known in principle and is described, for example, in EP-A 0 265 818 (CF Stockhausen). Reaction scheme
  • the manufacturing process is characterized by the sequence of the following - exemplary - reactions which are intended to aid in understanding the reaction process:
  • 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; further conventional auxiliaries and additives in amounts of 5 to 95, preferably 10 to 80 wt .-% can also contain his. 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: 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.
  • it is also possible to dispense with the addition of emulsifiers since the pseudoceramides according to the invention themselves have dispersing properties.
  • additives can be: preservatives, such as p-hydroxybenzoic acid ester; On oxidants, such as butylated hydroxytoluene, tocopherol; Humectants, such as, for example, 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 alkyl oligoglucosides, fatty alcohol ether sulfates, fatty acid isethionates, taurides and sarcosinates, ether carboxylic acids, sulfosuccinates, protein hydrolysates or fatty acid condensates, sulfotriglycerides, short-chain glucamides; Phospholipids, waxes such as beeswax, ozoce
  • 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 optionally formulated with the other ingredients mentioned together with volatile or non-volatile silicone compounds as anhydrous or almost anhydrous single-phase systems.
  • squalene or squalane optionally formulated with the other ingredients mentioned together with volatile or non-volatile silicone compounds as anhydrous or almost anhydrous single-phase systems.
  • volatile or non-volatile silicone compounds as anhydrous or almost anhydrous single-phase systems.
  • the 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 means - can be included. Typical examples are skin creams, soft creams, nutritional creams, sunscreen creams, night creams, skin oils, care lotions and body aerosols.
  • Example 1 Succinic acid octadecyl ester-N-octadecylsorbitylamide.
  • Example 1 was repeated using 0.1 mol of succinic acid mono-octadecyl ester and 0.1 mol of N-octadecylsorbitylamine.
  • a colorless wax was obtained which sinters at 45 to 52 ° C and begins to melt at 110 ° C.
  • Example 3 Example 3:
  • Example 1 was repeated using 0.1 mol of N, N-dioctadecylsuccinic acid monoamide and 0.1 mol of 1,1-bishydroxymethyl-2-hydroxyethylamine. A colorless wax was obtained which sintered at 30 to 35 ° C.
  • Succinic acid 9-octadecenyl ester-N-octadecylglucosylamide To the stirred solution of 36.9 g (0.1 mol) of succinic acid 9-octadecenyl ester and 10.1 g (0.1 mol) of triethylamine in 200 ml of THF was added a solution of 10.9 g (-5 0.1 mol) of chloro-carbonic acid ester in 50 ml of THF and the mixture stirred for 1 h at 0 ° C, triethylamine hydrochloride precipitated.

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  • Life Sciences & Earth Sciences (AREA)
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  • General Health & Medical Sciences (AREA)
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Abstract

L'invention concerne de nouveaux pseudocéramides de la formule (I), dans laquelle R1 désigne un reste alkyle et/ou alcényle linéaire ayant entre 6 et 30 atomes de carbone, R2 désigne hydrogène ou un reste alkyle éventuellement substitué par hydroxy, comportant entre 1 et 30 atomes de carbone, R3 désigne un reste oligo-hydroxyalkyle ayant entre 4 et 12 atomes de carbone et 3 à 10 groupes hydroxyle ou un reste glycosyle, X désigne un reste alkylène linéaire ou ramifié ayant entre 1 et 6 atomes de carbone, Y désigne oxygène, soufre ou un reste NR?4, et R4¿ désigne hydrogène ou un reste alkyle ayant entre 1 et 30 atomes de carbone. Ces substances s'utilisent comme 'lipides de barrière synthétique' pour produire des agents de soins pour la peau.
PCT/EP1995/000229 1994-02-01 1995-01-23 Pseudoceramides Ceased WO1995021181A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4402929.2 1994-02-01
DE19944402929 DE4402929C1 (de) 1994-02-01 1994-02-01 Pseudoceramide, Verfahren zu ihrer Herstellung und ihre Verwendung

Publications (1)

Publication Number Publication Date
WO1995021181A1 true WO1995021181A1 (fr) 1995-08-10

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PCT/EP1995/000229 Ceased WO1995021181A1 (fr) 1994-02-01 1995-01-23 Pseudoceramides

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DE (1) DE4402929C1 (fr)
WO (1) WO1995021181A1 (fr)

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US7998464B2 (en) 2005-09-29 2011-08-16 L'oreal S.A. Process for the photoprotective treatment of artificially dyed keratin fibers by application of a liquid water/steam mixture
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