+

WO1995021182A1 - Pseudoceramides - Google Patents

Pseudoceramides Download PDF

Info

Publication number
WO1995021182A1
WO1995021182A1 PCT/EP1995/000268 EP9500268W WO9521182A1 WO 1995021182 A1 WO1995021182 A1 WO 1995021182A1 EP 9500268 W EP9500268 W EP 9500268W WO 9521182 A1 WO9521182 A1 WO 9521182A1
Authority
WO
WIPO (PCT)
Prior art keywords
carbon atoms
radical
formula
pseudoceramides
anhydrides
Prior art date
Application number
PCT/EP1995/000268
Other languages
German (de)
English (en)
Inventor
Hinrich Möller
Rolf Wachter
Peter Busch
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 WO1995021182A1 publication Critical patent/WO1995021182A1/fr

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
    • 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
    • C07C233/20—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 carbon atom of an acyclic unsaturated carbon skeleton
    • 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
    • C07H15/12—Acyclic radicals, not substituted by cyclic structures attached to a nitrogen atom of the saccharide radical
    • 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 branched primary alcohols 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.
  • 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 disturbs the aqueous environment of the cells. Since the water bound in the deeper layers of the skin can only be supplied via the body fluid via vessels, but not from the outside, it becomes clear that maintaining the barrier function of the stratum comeum 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 build-up of the lipid bilayer, ie the permeability barrier, in the stratum comeum 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 represents a branched alkyl and / or alkenyl radical having 12 to 50 carbon atoms
  • R 2 represents hydrogen or an optionally hydroxy-substituted alkyl radical having 1 to 30 carbon atoms
  • R 3 represents a hydroxyalkyl radical having 2 to 12 carbon atoms and 1 to 10 Hydroxyl groups or a glycosyl radical
  • X represents a linear or branched alkyl radical having 1 to 6 carbon atoms.
  • the pseudoceramides to be used in accordance with the invention strengthen the natural barrier function of the skin, strengthen the skin and prevent protect drying.
  • the substances are modeled on the natural skin lipids, are dermatologically and ecotoxicologically harmless and can be incorporated homogeneously into the oil-phase cosmetic agent. They are colored white or ivory-like, odor-free, hydrolysis-resistant in the range of the skin pH value 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 a branched alkyl radical of a Guerbet alcohol with 12 to 36 carbon atoms, R 2 for hydrogen or a methyl group, R 3 for a hydroxyalkyl radical with 6 carbon atoms and 5 hydroxyl groups, a 1.1 -Bishydroxyme- ethyl-2-hydroxyethyl radical or a glucosyl radical and X represents an ethylene group.
  • the invention further relates to a process for the preparation of pseudoceramides of the formula (I)
  • R 1 is a branched alkyl and / or alkenyl radical having 6 to 30 carbon atoms
  • R 2 is hydrogen or one optionally hydroxy-substituted alkyl radical with 1 to 30 carbon atoms
  • R 3 stands for a hydroxyalkyl radical with 2 to 12 carbon atoms and 1 to 10 hydroxyl groups or a glycosyl radical
  • X stands for a linear or branched alkyl radical with 1 to 6 carbon atoms, characterized in that one
  • ver ⁇ -chain primary alcohols those having 12 to 50 carbon atoms ⁇ in question.
  • Typical examples are 2-ethylhexanol, isotridecyl alcohol, isopalmityl alcohol and isostearyl alcohol.
  • Particularly preferred starting materials are Guerbet alcohols with 12 to 36 carbon atoms, which are obtained by condensation of linear fatty alcohols in the presence of basic catalysts.
  • Typical examples of this are 2-hexyldecanol, 2-octyldodecanol, 2-decyltetradecanol, 2-dodecylhexadecanol, 2-tetradecyloctadecanol and 2-hexadecylicosanol.
  • Suitable dicarboxylic acid anhydrides are, for example, succinic anhydride, maleic anhydride, glutaric anhydride, phthalic anhydride and oxidic acetic anhydride.
  • Dicarboxylic anhydrides of the formula (III) are preferably used in which X represents an alkylene group having 2 to 4 carbon atoms.
  • the branched primary alcohols and the dicarboxylic 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 is first 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 into consideration.
  • 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
  • Hydroxyalkalyamines which are reacted with the acid chlorides or the mixed anhydrides of the acylation products are, for example, N-alkylsorbitylamines and in particular N-alkylglucosylamines 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. OH OH OH R 3
  • R 2 preferably represents an alkyl radical having 12 to 22 and in particular 16 to 18 carbon atoms.
  • the N-alkylglucamines are usually produced 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 hydroxyalkylamines are also methyl-substituted dialkanolamines, for example diethanolamine, 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 hydroxyalkylamines or glucosylamines can usually be used in a molar ratio of 1: 0.9 to 1: 1.1.
  • 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 amines such as triethylamine can be used as acid scavengers, for example tetrahydrofuran is recommended as solvent.
  • the products can then be purified by recrystallization, for example from lower alcohols or column chromatography.
  • the condensation of amine compounds with acid chlorides is is generally known and is described, for example, in EP-A 0 265 818 (CF Stockhausen).
  • the manufacturing process is characterized by the sequence of the following - exemplary - reactions which are intended to aid understanding of the reaction process:
  • 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 agent - contained and are present both as “water-in-oil” and “oil-in-water”emulsions; further conventional auxiliaries and additives in amounts of 5 to 95, preferably 10 to 80,% by weight may also be present. 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.
  • additives can be: preservatives, such as p-hydroxybenzoic acid ester; Antioxidants, such as butylhydroxytoluene, tocopherol; Moisturizing agents, such as, for example, 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 hydrolyzates or fatty acid condensates, sulfotriglycerides, short-chain glucamides; Phospholipids, waxes such as bees wax, ozokerite
  • 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 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.
  • 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.
  • He- ⁇ adecylsuccinic acid-C32 / 36-Guerbet alkyl ester-N-methyl sorbitol amide A solution of 8 was added to the stirred solution of 112.2 g (0.1 mol) of a monoester of hexadecylsuccinic acid with a C32 / 36 Guerbet alcohol in 150 ml of gasoline (bp. 65 to 90 ° C) at 20 ° C , 3 g (0.06 mol) of phosphorus trichloride in 30 ml of gasoline and the mixture stirred for 3 h at this temperature and 3 h at 40 ° C.
  • 0.1 mol of hexadecylsuccinic acid monoguerbetalkylester was 0.11 Mol l, l-bishydroxymethyl-2-hydroxyethylamine implemented. A colorless wax was obtained.
  • Hexadecylsuccinic acid-2-octadodecyl ester-N-octadecylglucosylamide A solution of 10.9 was added to the stirred solution of 112.2 g (0.1 mol) of hexadecyl succinic acid mono-2-octyldodecyl ester and 10.1 g (0.1 mol) of triethylamine in 250 ml of tetrahydrofuran at -5 ° C g (0.1 mol) of ethyl chlorocarbon were added to 50 ml of THF and the mixture was stirred for a further 2 hours at 0 ° C., triethylamine hydrochloride precipitating out.

Landscapes

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

Abstract

L'invention concerne de nouveaux pseudocéramides de la formule (I), dans laquelle R1 désigne un reste alkyle et/ou alcényle ramifié ayant entre 12 et 50 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 hydroxyalkyle ayant entre 2 et 12 atomes de carbone et 1 à 10 groupes hydroxyle ou un reste glycosyle, et X désigne un reste alkylène linéaire ou ramifié ayant entre 1 et 6 atomes de carbone. Ces substances s'utilisent comme 'lipides de barrière synthétique' pour produire des agents de soins pour la peau.
PCT/EP1995/000268 1994-02-03 1995-01-25 Pseudoceramides WO1995021182A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19944403258 DE4403258C1 (de) 1994-02-03 1994-02-03 Pseudoceramide
DEP4403258.7 1994-02-03

Publications (1)

Publication Number Publication Date
WO1995021182A1 true WO1995021182A1 (fr) 1995-08-10

Family

ID=6509347

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/000268 WO1995021182A1 (fr) 1994-02-03 1995-01-25 Pseudoceramides

Country Status (2)

Country Link
DE (1) DE4403258C1 (fr)
WO (1) WO1995021182A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998021176A1 (fr) * 1996-11-11 1998-05-22 Aekyung Industrial Co., Inc. Nouveaux pseudoceramides et preparations les contenant utilisees en dermatologie externe
WO1998034943A1 (fr) * 1997-02-10 1998-08-13 Instituut Voor Agrotechnilogisch Onderzoek (Ato-Dlo) Amines et glycosides tensio-actifs

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2160506A1 (en) * 1971-11-15 1973-06-29 Akzo Nv Dry carpet shampoo - based on surfactant plant gum mixt
EP0398272A1 (fr) * 1989-05-19 1990-11-22 Kao Corporation Dérivés amidés et préparations pour la peau les contenant
EP0450527A2 (fr) * 1990-03-30 1991-10-09 Kao Corporation Amides N-tris (hydroxyméthyl)méthyl d'acides gras et compositions cosmétiques les contenant
EP0455429A2 (fr) * 1990-05-01 1991-11-06 Unilever Plc Compositions cosmétiques
DE4238210C1 (de) * 1992-11-12 1993-12-09 Henkel Kgaa Fettsäure-bis-sorbitylamide

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5051448A (en) * 1984-07-24 1991-09-24 The Mclean Hospital Corporation GABA esters and GABA analog esters
US5281746A (en) * 1993-02-01 1994-01-25 Monsanto Company Process for preparing peroxyacid precursors having amide moieties in the fatty chain

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2160506A1 (en) * 1971-11-15 1973-06-29 Akzo Nv Dry carpet shampoo - based on surfactant plant gum mixt
EP0398272A1 (fr) * 1989-05-19 1990-11-22 Kao Corporation Dérivés amidés et préparations pour la peau les contenant
EP0450527A2 (fr) * 1990-03-30 1991-10-09 Kao Corporation Amides N-tris (hydroxyméthyl)méthyl d'acides gras et compositions cosmétiques les contenant
EP0455429A2 (fr) * 1990-05-01 1991-11-06 Unilever Plc Compositions cosmétiques
DE4238210C1 (de) * 1992-11-12 1993-12-09 Henkel Kgaa Fettsäure-bis-sorbitylamide

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS FORMULA INDEX 1977-1981 *
CHEMICAL ABSTRACTS, vol. 92, no. 14, 7 April 1980, Columbus, Ohio, US; abstract no. 113228, ALIEV Z.E. ET AL: "Studies of the effect of some organic compounds on antifouling and anticorrosion properties of heavy fuels" page 139; column 1; *
PRISADKI SMAZ. MASLAM 1978, 5, 133-7 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998021176A1 (fr) * 1996-11-11 1998-05-22 Aekyung Industrial Co., Inc. Nouveaux pseudoceramides et preparations les contenant utilisees en dermatologie externe
US6221371B1 (en) * 1996-11-11 2001-04-24 Aekyung Industrial Co., Inc. Pseudoceramides, and dermatologic external preparations containing the same
WO1998034943A1 (fr) * 1997-02-10 1998-08-13 Instituut Voor Agrotechnilogisch Onderzoek (Ato-Dlo) Amines et glycosides tensio-actifs
NL1005244C2 (nl) * 1997-02-10 1998-08-18 Inst Voor Agrotech Onderzoek Oppervlakte-actieve aminen en glycosiden.

Also Published As

Publication number Publication date
DE4403258C1 (de) 1995-03-09

Similar Documents

Publication Publication Date Title
EP0748328B1 (fr) Pseudoceramides
DE4402929C1 (de) Pseudoceramide, Verfahren zu ihrer Herstellung und ihre Verwendung
DE4420736C1 (de) Pseudoceramide
DE4424530A1 (de) Pseudoceramide
DE69320980T2 (de) Verfahren zur herstellung von phytosphingosin-enthaltenden ceramiden und kosmetische zusammensetzungen, die diese enthalten
DE4424533A1 (de) Oligohydroxydicarbonsäurederivate
DE69230235T2 (de) Kosmetische Zusammensetzung
DE3884021T2 (de) Äusserliches Hautpflegepräparat.
DE69107791T2 (de) Eine Dispersion von Lipidvesikeln enthaltende Kosmetika oder Arznei- bzw. Nahrungsmittel.
KR19980034991A (ko) 비천연세라미드 관련화합물 및 이를 함유하는 피부외용제
EP0864563B1 (fr) Esters d'aminoacid N-acylés pour la protection de la peau et des cheveaux
DE69433062T2 (de) Ceramid i analoge auf basis von phytosphingosine
DE4326959C2 (de) Verwendung von Fettsäure-N-alkylpolyhydroxyalkylamiden
DE4403258C1 (de) Pseudoceramide
DE19523479C1 (de) Verwendung von Zuckermonosäureamiden in kosmetischen Präparaten
DE4326958C2 (de) Verwendung von Fettsäure-N-alkylglykosylamiden
DE19959000B4 (de) Verwendung primärer Monoalkylether von Eigenkondensationsprodukten des Glycerins
DE4404175C1 (de) Pseudoceramide
DE4430851C1 (de) Dicarbonsäureesterderivate mit einem Diacyloxypropylrest
DE4341451C1 (de) N-acylierte Mono- und/oder Bis-aminosäureoligohydroxyalkylamide
WO1995019366A1 (fr) Pseudo-ceramides
DE19949518A1 (de) Primäre Monofettsäureester von Eigenkondensationsprodukten des Glycerins
DE10341234A1 (de) N-Acyl-hydroxyaminosäurealkylamide, Verfahren zu ihrer Herstellung und ihre Verwendung
JPH09176097A (ja) （２ｓ，３ｒ）−２−アミノアルカン−１，３−ジオール類の製造方法
DE19544710C2 (de) Verdickungsmittel

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): JP US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase
点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载