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WO1996001799A1 - Derives d'acide oligohydroxydicarboxylique - Google Patents

Derives d'acide oligohydroxydicarboxylique Download PDF

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Publication number
WO1996001799A1
WO1996001799A1 PCT/EP1995/002563 EP9502563W WO9601799A1 WO 1996001799 A1 WO1996001799 A1 WO 1996001799A1 EP 9502563 W EP9502563 W EP 9502563W WO 9601799 A1 WO9601799 A1 WO 9601799A1
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WO
WIPO (PCT)
Prior art keywords
acid
oligohydroxydicarboxylic
formula
carbon atoms
linear
Prior art date
Application number
PCT/EP1995/002563
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 WO1996001799A1 publication Critical patent/WO1996001799A1/fr

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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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids

Definitions

  • the invention relates to oligohydroxydicarboxylic acid derivatives which are obtainable by reacting oligohydroxydicarboxylic acids or their esters with fatty alcohols and / or fatty amines, a process for the preparation of the oligohydroxycarboxylic acid derivatives, skin care products containing the oligohydroxydicarboxylic acid derivatives and the use of the oligohydroxy-derived carboxylic acid derivatives.
  • a balanced water balance in the individual skin layers plays an important role for the elasticity and appearance of the skin.
  • the amount 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 the transepidermal water loss, as a result of which the aqueous environment of the cells is disturbed. Because that in deeper Water bound to the skin layers 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 corneum is essential for the overall condition of the skin. [see. SE Friberg 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 location in 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, as a result of which the described disorders of the skin function can be counteracted. [see. 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
  • R- ° for a hydroxyalkyl
  • Z for a sugar or phosphate radical
  • the object of the present invention is to develop new high-performance ceramide-analog structures which are distinguished by the simplest possible synthesis. Another task is to create new connections with one another Manufacture structure that comes very close to ceramides or pseudoceramides on the basis of non-animal raw materials.
  • the invention relates to oligohydroxycarboxylic acid derivatives of the formula I.
  • Oligohydroxydicarboxylic acid derivatives of the formula I are particularly preferred, in which R 1 and R 2 are identical or different and for a linear or branched alkyl and / or alkenyl radical having 12 to 22 carbon atoms, X 1 and X 2 for oxygen, R 3 for a hydroxyl group and n stand for a number of 4.
  • the invention further relates to a process for the preparation of oligohydroxydicarboxylic acid derivatives of the formula I.
  • X x and X 2 are the same or different and for oxygen or an NR ⁇ group, in which R * * is hydrogen or a linear or branched alkyl radical having 1 to 30 carbon atoms, R 3 is hydrogen or a hydroxyl group and n is a number from 1 to 5, with the proviso that that when n is 1, R 3 is a hydroxy group, which is characterized in that
  • R 3 and n have the meaning given above, or a reactive derivative thereof, in a manner known per se with compounds of the formula III and / or IV
  • Suitable oligohydroxydicarboxylic acids which come under general formula II are those having 3 to 7 carbon atoms and 1 to 5 hydroxyl groups. Typical examples are tartronic acid, malic acid, D - (-) - tartaric acid, L - (+) - tartaric acid, DL-tartaric acid, glucaric acid, mucic acid, mannosugaric acid, arabinosugaric acid or heptaglucaric acid.
  • the dicarboxylic acids themselves or their reactive derivatives are used. Lactones and C1-C4-alkyl esters are particularly suitable as reactive carboxylic acid derivatives.
  • the corresponding dicarboxamides ie when X 1 and / or X 2 represent an NR ⁇ group, it is particularly advantageous to convert the oligohydroxydi carboxylic acids into the corresponding C 4 -C 4 alkyl esters.
  • These esters can be obtained in a manner known per se by esterifying the acids in the C 1 -C 4 alcohols in the presence of a catalyst.
  • the oligohydroxydicarboxylic acids or their reactive derivatives are reacted in a manner known per se with compounds of the formulas III and / or IV, it being possible for the compounds of the formulas III and IV to be identical or different.
  • the amount of compounds III and IV is usually selected so that in the end product with the formula I at least one of R 1 or R 2 is a carbon radical having more than 6, preferably more than 12, carbon atoms.
  • the oligohydroxydicarboxylic acids or their reactive derivatives and the compounds of the formulas III and / or IV are used in a molar ratio of 1: 0.9 to 1: 2.2.
  • Either alcohols, ie when X 1 and X 2 are oxygen, or amines, ie when X 1 and X 2 are a group NR * *, can be used as compounds with the formulas III and IV.
  • Alcohols with the formula R — OH and R 2 OH are in particular those in which R 1 and R 2 are linear or branched alkyl and / or alkenyl radical having 12 to 22 carbon atoms.
  • suitable alcohols are 1-, 2-hexadecanol, 1-octadecanol, 9-octadecen-l-ol, 1-tetradecanol, 1-dodecanol, 1-isononol, 1-isotridecanol, 1-octanol , 2-octanol, hexanol, 1-eicosanol, 1-heneicosanol, 1-docosanol, 1-nonanol, 1-isononanol, 1-isotridecanol, 1-iso-octadecanol, particularly suitable.
  • suitable alcohols are, for example, the native fatty alcohols based on plants, such as lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, behen alcohol, oleyl alcohol, elaidyl alcohol, ricinol alcohol, linoleyl alcohol, linolenyl alcohol and their technical mixtures, such as coconut oil alcohol, palm fat and palm alcohol or also natural alcohol.
  • Particularly suitable amines with the compounds HNR 1 R 4 and HNR 2 R 4 are alkylamines, in which R 2 is a linear or branched alkyl and / or alkenyl radical having 12 to 22 carbon atoms and R 4 is hydrogen or a linear one or branched alkyl radical having 1 to 22 carbon atoms, so-called fatty amines.
  • Examples include fatty amines, especially primary fatty alkylamines, such as hexadecylamine, octadecylamine, dodecylamine, decylamine or octylamine, but also dialkylamines, such as dioctadecylamine, dihexadecylamine, and Guerbetamines, such as.
  • fatty amines especially primary fatty alkylamines, such as hexadecylamine, octadecylamine, dodecylamine, decylamine or octylamine, but also dialkylamines, such as dioctadecylamine, dihexadecylamine, and Guerbetamines, such as.
  • methyloctadecylamine can be called.
  • As a technical Fatty amines in particular those based on plants, such as coconut amine, palm kernel amine or
  • the condensation reaction is preferably carried out at temperatures in the range from 20 to 95 ° C. in the presence of a suitable catalyst, the reaction times typically being up to 24 hours.
  • a suitable catalyst such as NaOH, KOH, CH3 ⁇ Na, C2HsONa and acidic catalysts such as H2SO4, p-toluenesulfonic acid, methanesulfonic acid, phosphoric acid or amidosulfonic acid are used for the transesterification of the lower alkyl esters with fatty alcohols.
  • suitable solvents are gasoline fractions, 1,2-dimethoxyethane, acetone, butanone, tert-butyl methyl ether or tetrahydrofuran.
  • the invention further relates to skin care compositions containing oligohydroxydicarboxylic acid derivatives of the formula I.
  • compositions according to the invention can contain the oligohydroxydicarboxylic acid derivatives in amounts of 1 to 50, preferably 1 to 30, in particular 2 to 10% by weight, based on the composition, both as “water-in-oil” and “oil-in-water” emulsions are present; further conventional auxiliaries and additives can be present in amounts of 5 to 95, preferably 10 to 80,% by weight.
  • 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 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.
  • Other additives can be: preservatives such as p-hydroxybenzoic acid ester; Antioxidants, such as butylated hydroxytoluene, tocopherol: humectants, such as glycerol, sorbiol.
  • the oligohydroxydicarboxylic acid derivatives can be mixed with conventional ceramides, pseudoceramides, cholesterol, cholesterol fatty acid esters, fatty acids, triglycerides, cerebrosides, phospholipids and similar substances, liposomes being formed.
  • the oligohydroxydicarboxylic acid derivatives can be mixed with accelerators, in particular with essential oils, such as eucalyptol, menthol and the like.
  • the oligohydroxydicarboxylic acid derivatives 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.
  • constituents and typical compositions can be found, for example, in WO 90/01323 (Bernstein) and SE Friberg, J. Soc. Co ⁇ et. Chem. 41, 155 (1990).
  • oligohydroxydicarboxylic acid derivatives 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 oligohydroxydicarboxylic acid derivatives 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 50, preferably 1 to 30, in particular 2 to 10 % By weight, based on the composition, may be present.
  • synthetic barrier lipids for the production of skin care products in which they are used in amounts of 1 to 50, preferably 1 to 30, in particular 2 to 10 % By weight, based on the composition, may be present.
  • special formulations which form liquid-crystalline, lamellar structures are also particularly advantageous for maintaining the barrier function of the skin.
  • formulations can be based on the composition of the horny layer lipids as main components 5% by weight to 50% by weight of a compound with the formula I, 25% by weight to 75% by weight of saturated and unsaturated fatty acids, their alkali metal salts or mixtures of the Fatty acids and their salts, 10% by weight to 50% by weight of cholesterol, phytosterols and / or cholesteryl sulfate, 5% by weight to 30% by weight of triglycerides (triolein) and wax esters, and 2% by weight.
  • triglycerides triolein
  • triolein triolein
  • triolein triolein
  • wax esters 2% by weight.
  • -% to 20 wt .-% phospholides such as lecithins or kephalins contain.
  • Typical examples of such formulations are skin creams, soft creams, nutritional creams, sunscreen creams, night creams, skin oils, skin care lotions and body aerosols.
  • a mixture of 64.5 g (0.2 mol) of mucic acid dibutyl ester, 119.4 g (0.4 mol) of the equimolar mixture of octadecanol and docosanol and 0.5 g of p-toluenesulfonic acid was at 90 ° C. under pressure for 12 hours of 50 mbar, heated, butanol formed was distilled off at the same time.
  • the reaction mixture was dissolved in acetone, stirred with 0.3 g of sodium carbonate and filtered. The filtrate was evaporated and dried. 146 g (95% of theory) of a beige-colored product which had a melting point of 59-88 ° C. were obtained.
  • a mixture of 64.5 g (0.2 mol) of mucic acid dibutyl ester, 102.6 g (0.4 mol) of the equimolar mixture of hexadecanol and octadecanol was prepared analogously to Example 2b.
  • a colorless waxy product with a melting point of 100-112 ° C. was obtained.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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Abstract

De nouveaux dérivés d'acide oligohydroxycarboxylique ont la formule (I), dans laquelle R1 désigne un résidu alcoyle et/ou alcényle linéaire ou ramifié avec 6 à 30 atomes de carbone, R2 désigne un résidu alcoyle et/ou alcényle linéaire ou ramifié avec 1 à 30 atomes de carbone, X1 et X2 sont identiques ou différents et désignent oxygène ou un groupe NR4 dans lequel R4 désigne hydrogène ou un résidu alcoyle linéaire ou ramifié avec 1 à 30 atomes de carbone, R3 désigne hydrogène ou un groupe hydroxyle et n vaut 1 à 5, à condition que lorsque n vaut 1, R3 soit un groupe hydroxyle. Ces substances sont utiles pour former une barrière lipidique synthétique pour produits de soins de la peau.
PCT/EP1995/002563 1994-07-12 1995-07-03 Derives d'acide oligohydroxydicarboxylique WO1996001799A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4424533.5 1994-07-12
DE19944424533 DE4424533A1 (de) 1994-07-12 1994-07-12 Oligohydroxydicarbonsäurederivate

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US7157413B2 (en) 2002-07-08 2007-01-02 L'oreal Detergent cosmetic compositions comprising an anionic surfactant, an amphoteric, cationic, and/or nonionic surfactant, and a polysacchardie, and use thereof

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US2122716A (en) * 1933-08-02 1938-07-05 Du Pont Hydroxy carboxylic acid esters of long chain alcohols
DE878863C (de) * 1950-12-16 1953-06-08 Hoechst Ag Verfahren zur Herstellung perlfoermiger oder koerniger Polymerisationsprodukte
US4078147A (en) * 1975-09-10 1978-03-07 The Nisshin Oil Mills, Ltd. Hydroxy acid esters of higher alcohols
EP0526301A1 (fr) * 1991-07-24 1993-02-03 Agro Industrie Recherches Et Developpements (A.R.D.) Alcoyl galactarates, leurs procédés de préparation et leurs applications

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Publication number Priority date Publication date Assignee Title
US2122716A (en) * 1933-08-02 1938-07-05 Du Pont Hydroxy carboxylic acid esters of long chain alcohols
DE878863C (de) * 1950-12-16 1953-06-08 Hoechst Ag Verfahren zur Herstellung perlfoermiger oder koerniger Polymerisationsprodukte
US4078147A (en) * 1975-09-10 1978-03-07 The Nisshin Oil Mills, Ltd. Hydroxy acid esters of higher alcohols
EP0526301A1 (fr) * 1991-07-24 1993-02-03 Agro Industrie Recherches Et Developpements (A.R.D.) Alcoyl galactarates, leurs procédés de préparation et leurs applications

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Title
PETER D. HOAGLAND: "The Formation of Intermediate Lactones During Aminolysis of Diethyl Galactarate", CARBOHYDRATE RESEARCH, vol. 98, AMSTERDAM NL, pages 203 - 208 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999042598A2 (fr) 1998-02-20 1999-08-26 Zeneca Limited Production de semences hybrides
EP2258856A1 (fr) 1998-02-20 2010-12-08 Syngenta Limited Production de sémences hybrides
US7157413B2 (en) 2002-07-08 2007-01-02 L'oreal Detergent cosmetic compositions comprising an anionic surfactant, an amphoteric, cationic, and/or nonionic surfactant, and a polysacchardie, and use thereof

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