DE4430851C1 - New di:carboxylic acid ester(s) contg. di:acyloxy:propyl residue - Google Patents

Abstract

New dicarboxylic acid ester derivatives with a diacyloxypropyl residue have formulas (I) or (II), in which R<1> stands for a poly-(C2-C3)-alkylene oxide residue with 2 to 20 monomer units or an oligohydroxyalkyl residue with 2 to 8 carbon atoms and 1 to 6 hydroxy groups; R<2> and R<3> are the same or different and stand for a straight- or branched-chain, saturated or unsaturated alkyl residue with 8 to 30 carbon atoms; X stands for a linear or branched alkylene residue with 1 to 6 carbon atoms, that may also be unsaturated and form part of a cyclic system, oxygen, sulphur, a thionyl or sulfonyl group,; Y stands for oxygen or a group NR<4>, in which R<4> stands for a hydrogen atom, an alkyl residue with 1 to 4 carbon atoms or a hydroxyalkyl group with 2 to 4 carbon atoms. These compounds are useful as synthetic barrier lipids in skin care products.

Description

Field of the Invention

The invention relates to dicarboxylic acid ester derivatives with a Diacyloxypropyl residue, a process for making the Dicar bonic ester derivatives with a diacyloxypropyl residue, skin care with agents containing the dicarboxylic acid ester derivatives a diacyloxypropyl residue and the use of this compound for the manufacture of skin care products.

State of the art

It plays out for the elasticity and the appearance of the skin balanced water balance in the individual skin layers ne important role. In the dermis and in the boundary layer of the Epidermis near the basement membrane is the level of bound Water greatest. The skin's elasticity is crucial the collagen fibrils are shaped in the dermis, the speci fish conformation of collagen by the incorporation of water molecules is reached. Destruction of the lipid barrier in the Stratum corneum (SC), for example, by surfactants leads to egg an increase in transepidermal water loss, causing the aqueous environment of the cells is disturbed. Because that in deeper Layers of water bound to the skin only via vessels over the body  perfluid, but not from outside, it becomes clear that the preservation of the barrier function of the stratum Corneum is essential for the overall condition of the skin. [see. S.E. Friberg et al., C.R. 23rd CED Congress, Barcelona, 1992, P. 29].

Ceramides are lipophilic amides of long-chain fatty acids, which are generally derived from sphingosine or phytosphingosine deduce. This class of bodywork has considerable importance genes have been extracted since they were Space between the corneocytes as key components for the Structure of the lipid bilayer, i.e. the permeability barrier, in the Stratum corneum of human skin. Ceramides have molecular weights of well below 1000, so that at external delivery in a cosmetic formulation chen of the site of action is possible. The external application from Ceramids leads to the restoration of the lipid barrier, causing causally counteracts the described disorders of skin function can be counteracted. [see. R.D. Petersen, Cosm. Toil. 107, 45 (1992)].

The use of ceramides is due to their lack of ver availability has so far set limits. It has therefore already Ver given, ceramide-analogous structures, so-called "synthetic barrier lipids (SBL)" or "pseudoceramides" syn thetize and use for skin care. [see. G.Imokawa et al., J. Soc. Cosmet. Chem. 40 273 (1989)].

For example, in the European Disclosure publications EP-A 0 277 641 and EP-A 0 227 994 (Kao) Ceramidana loge of the following structure proposed:

From European laid-open publications EP-A 0 482 860 and EP-A 0 495 624 (Unilever) are structures related to ceramide known formula:

For the protection of skin and hair are used in the European Patent application EP-A 0 455 429 (Unilever) also sugar deri vate of the following composition proposed:

Here Ra stands for hydrogen or an unsaturated fatty acyl radical, z for numbers from 7 to 49, R ^b for a hydroxyalkyl and Z for a sugar or phosphate radical.

Notwithstanding these attempts, success is with these Can achieve substances, so far unsatisfactory; especially the performance of natural ceramides will not he enough. Furthermore, the synthesis sequences are technically complex and therefore costly as to the importance of the substances additionally relativized.

The object of the present invention is new lei to develop high-strength ceramide-analogous structures that characterized by the simplest possible synthesis. A white Another task is to create new connections with a  Structure very close to the ceramides or the pseudoceramides comes to manufacture based on non-animal raw materials.

Description of the invention

The invention relates to dicarboxylic acid ester derivatives a diacyloxypropyl radical with the formulas I or II

in the
R¹ is a poly (C₂-C₃) alkylene oxide radical having 2 to 20 monomer units or an oligohydroxyalkyl radical having 2 to 8 carbon atoms and 1 to 6 hydroxyl groups,
R² and R³ are identical or different and are straight-chain or branched, saturated or unsaturated alkyl radical having 8 to 30 carbon atoms,
X represents a linear or branched alkylene radical with 1 to 6 carbon atoms, which can also be unsaturated and can be part of a ring system, oxygen, sulfur, the thionyl or sulfonyl group,
Y is oxygen or a group NR⁴, where R⁴ is a hydrogen atom, an alkyl radical having 1 to 4 carbon atoms or a hydroxyalkyl group having 2 to 4 carbon atoms,
mean.

Dicarboxylic acid ester derivatives with a Diacyloxypropyl radical in which R¹ is an oligohydroxyalkyl radical with 3 up to 8 carbon atoms and 2 to 6 hydroxyl groups, R² and R³ are the same or different and have a straight chain or branched, saturated or unsaturated alkyl radical with 12 up to 22 carbon atoms, X is an alkylene group with 2 to 4 Carbon atoms and Y is a group NR⁴, wherein R⁴ is a Hydrogen atom, an alkyl radical having 1 to 4 carbon atoms or a hydroxyalkyl group having 2 to 4 carbon atoms stands mean.

Furthermore, dicarboxylic acid ester derivatives with a Diacyloxypropylrest preferred, wherein R¹ for one Polyethylene oxide residue with 4 to 12 monomer units, R² and R³ are the same or different and for a straight chain or branched, saturated or unsaturated alkyl radical with 12 up to 22 carbon atoms, X for an alkylene group with 2 to 4 Carbon atoms and Y represent oxygen.

Manufacturing process

Another object of the invention relates to a method for the production of dicarboxylic acid ester derivatives with a Diacyloxypropyl radical with the general formulas I and / or II

in the
R¹ is a poly (C₂-C₃) alkylene oxide radical having 2 to 20 monomer units or an oligohydroxyalkyl radical having 3 to 8 carbon atoms and 2 to 6 hydroxy groups,
R² and R³ are identical or different and are straight-chain or branched, saturated or unsaturated alkyl radical having 8 to 30 carbon atoms,
X represents a linear or branched alkylene radical with 1 to 6 carbon atoms, which can also be unsaturated and can be part of a ring system, oxygen, sulfur, the thionyl or sulfonyl group,
Y is oxygen or a group NR⁴, where R⁴ is a hydrogen atom, an alkyl radical having 1 to 4 carbon atoms or a hydroxyalkyl group having 2 to 4 carbon atoms,
mean that is characterized in that one

• a) Diglycerides with the formulas III or IV with dicarboxylic acid anhydrides of the formula (V) wherein R², R³ and X have the meanings given above, acylated,
• b) the resulting acylation products known per se ter way using chlorine compounds in their acid chlorides or mixed anhydrides and
• c) the resulting acid chlorides or mixed anhydri de condensed with compounds of formula (VI) R¹-Y-H (VI), wherein R¹ and Y have the meanings given above.

Diglycerides

In the sense of the method according to the invention come as diglyce ride 1,2- and 1,3-diglycerides with carboxylic acids into consideration,  which have an alkyl radical with a straight-chain or branched, saturated or unsaturated alkyl radical with 8 to 30 carbons have atoms of matter. Typical examples of glycerides that can be used in the process according to the invention 1,2- and 1,3-dihexadecanoylglycerol, 1,2- and 1,3-dioctadeca noylglycerin, 1,2- and 1,3- (9-dioctadecenoyl) glycerin, 1,2- and 1,3-ditetradecanoylglycerol, 1,2- and 1,3-didodecanoylgly cerin, 1,2- and 1,3-diisononoylglycerol, 1,2- and 1,3-diiso tridecanoylglycerol, 1,2- and 1,3-dioctanoylglycerol, 1,2- and 1,3-Dieicosanoylglycerin, 1,2- and 1,3-Diheneicosanoylglyce rin, 1,2- and 1,3-didocosanoylglycerol, 1,2- and 1,3-dihepta decanoylglycerol, 1,2- and 1,3-dinonanoylglycerol, 1,2- and 1,3-didecanoylglycerol and 1,2- and 1,3-dihydrotalgala noylglycerin.

Dicarboxylic acid anhydrides

Amber, for example, comes as dicarboxylic acid anhydrides acid anhydride, maleic anhydride, glutaric anhydride, Phthalic anhydride, thiodiacetic anhydride, sulfonyl dies acetic anhydride, 2-methyl, 2,2-, 3,3-dimethylglutaric acid hydride, hexyhydrophthalic anhydride, 1,2-cyclopropanedicarbon acid anhydride, bicyclo- [2,2,1] -hepten-2,3-dicarboxylic acid drid, 5-norbonan-2,3-dicarboxylic anhydride, itaconic acid drid and oxidic acetic anhydride into consideration. Preferably are used dicarboxylic anhydrides of the formula V in which X represents an alkylene group with 2 to 4 carbon atoms.

The acylation of the diglycerides with the formulas III or IV can be carried out in a manner known per se. Preferential wise the reaction is in substance, d. H. without using Solvents. The reaction temperature is preferably between 20 and 150 ° C, in particular between 50 and 100 ° C. It is advisable to slowly add the anhydride if you have previously warmed and stirred alcohol and that Reaction mixture kept at elevated temperature for some time.  

The reaction can be carried out without the presence of a catalyst leads.

Usually you can diglycerides and dicarboxylic acid Use anhydrides in a molar ratio of 1: 0.9 to 1: 1. The acylation product obtained can be used directly for transfer who converted into the acid chloride or the mixed ester the.

Chlorine compounds

To establish a link between the acylation products and the To be able to produce compounds with the general formula VI NEN, the free carboxyl group of the acylation products next in a manner known per se into the acid chloride leads. As chlorine compounds for the production of acid chlorides are preferably phosphorus trichloride or thionychloride used. The acylation products and the chlorine compounds in a molar ratio of 1: 0.4 to 1: Insert 2.5. The chlorination is preferably carried out in the presence of a solvent at -10 to 50 ° C in the absence of Water performed. Examples of suitable solvents are: Petrol fractions, toluene, ethyl acetate, 1,2-dimethoxyethane, tert-butyl methyl ether or tetrahydrofuran. Man can also work in the melt without solvents. After completion of the reaction, the impurities, for. B. hypophosphorous acid deposited, unreacted chlorine distilled off or - if it is only a small amount Amounts act - leave in the reaction mixture.

In a variant of the method according to the invention, the Acylation products with chlorinated carbonic acid alkyl esters in one inert solvents converted to the mixed anhydrides become. The reaction preferably takes place in the presence of a Acid scavenger such as triethylamine, tributylamine or sodium or Potassium carbonate instead, with the reactants in about mola  Ren amounts at temperatures from -10 to 50 ° C, preferably 0 up to 10 ° C. Following the implementation it is advisable to filter off the salts formed. In this Relation to the publication of C. Bersena in J. Org.Chem. 27, 3489 (1962). For the following Reaction can either be the solution obtained or else its evaporated residue can be used.

Oligohydroxyalkyl compounds

Preferred compounds with the formula VI are those which the Correspond to formula VII,

in which R¹ and R⁴ have the meanings given above, where R¹ preferably for an oligohydroxyalkyl radical with 3 to 8 Koh lenstoffatomen and 2 to 6 hydroxy groups.

The compounds with formula VII are oligohydroxyalkylamines ne and are usually by reductive amination of Am moniac, amines, but also glycamines, which differ from glucose, Derive maltose, fructose or palatinose.

In a preferred embodiment of the invention Glucamine or N-alkylglucamine of the formula VIII used,

in the R⁴ preferably for hydrogen or an alkyl radical with 1 to 4 carbon atoms, especially for an alkyl rest with 1 to 2 carbon atoms.

Examples of oligohydroxyalkylamines are N-methyl-glu camin and N- (2-hydroxyethyl) -glucamine called. As another Hy Droxyalkylamines also come diethanolamine, 2-amino-2-methyl 1,3-propanediol, 2-amino-2-hydroxymethyl-1,3-propanediol and 2,3-dihydroxypropylamine. The N-alkylglucamines are usually by reductive amination of glucose manufactured.

Poly (C₂-C₃) alkylene oxides

As poly (C₂-C₃) alkylene oxides, which are used to produce the invented connections according to the invention can be used preferably suitable those which have 4 to 12 monomer units sen, with polyethylene glycol being particularly preferred.

The poly (C₂-C₃) alkylene oxides, in which in the formulas I and II R¹ is a polyethylene or polypropylene oxide residue with 2 to 20 monomer units or a residue with ethylene oxide and Pro pylene oxide and Y can be oxygen in the usual way by ethoxylation or propoxylation of the half esters with the Formula IX or X, which are acylation products,

in which R², R³ and X have the meaning given above, in the presence of a basic catalyst such as sodium or Potassium hydroxide or sodium methoxide or ethanolate, at Temperatures between 100 and 200 ° C, preferably between 120 and 160 ° C, usually without using an inert solution be obtained by means. The making of these connections is in the German patent application DE-A1-42 38 032 (Henkel) described.

Usually you can acid chlorides or mixed Anhy dride and the hydroxyalkylamines or glucosylamines and poly (C₂-C₃) alkylene oxides in a molar ratio of 1: 0.9 to 1: Insert 1.1. The condensation reaction is preferably at Temperatures in the range of 20 to 60 ° C in the presence of alkali lischer catalysts performed, the reaction times typically can be 1 to 10 hours. As an acid scavenger can soda, potash or tertiary amines such. B. Triethyl amine can be used. The recommended solvent is for example tetrahydrofuran. Afterwards the products by recrystallization, for example from lower alcohols or column chromatography. The condensation of amine compounds with acid chlorides is basically be is known and is, for example, in EP-A-0 265 818 (CP Stock houses).  

Skin care products

Skin care products can use the dicarboxylic acid esters derivatives with a diacyloxypropyl radical in amounts of 1 to 50, preferably from 1 to 30, in particular from 2 to 10% by weight - based on the funds - included and both as "What water-in-oil "and" oil-in-water "emulsions are present; white Other customary auxiliaries and additives can be used in amounts of 5 to 95, preferably 10 to 80 wt .-% be included. Further the formulations can contain water in an amount up to 99 % By weight, preferably 5 to 80% by weight.

Examples of suitable carrier oils are: mine ral oils, vegetable oils, silicone oils, fatty acid esters, dialkyl ethers, Fatty alcohols and Guerbet alcohols. As emulsifiers can for example: sorbitan esters, monoglycerides, Polysorbates, polyethylene glycol mono / difatty acid ester, highly eth oxylated fatty acid esters as well as high molecular silicone compound applications such as B. Dimethylpolysiloxane with an average Lich molecular weight from 10,000 to 50,000. Additional additive substances can be: preservatives such as B. p-Hydroxy benzoic acid esters; Antioxidants such as B. butylated hydroxytoluene, Tocopherol: humectants, such as. B. glycerin, sorbiol. 2- Pyrrolidine-5-carboxylate, dibutyl phthalate, gelatin, poly glycols with an average molecular weight of 200 up to 600; Buffers such as B. lactic acid / TEA or lactic acid / NaOH; mild surfactants such as B. alkyl oligoglucosides, fatty al alcohol ether sulfates, fatty acid isethionates, taurides and sarco sinates, ether carboxylic acids, sulfosuccinates, protein hydrolyzates or fatty acid condensates, sulfotriglycerides, short-chain glu camide; Phospholipids, waxes such as B. beeswax, ozoke  rit wax, paraffin wax; Plant extracts, e.g. B. from Aloe vera; Thickeners; Dyes and perfumes, as well as sun protection medium, such as B. ultrafine titanium dioxide or organic matter fe such as p-aminobenzoic acid and its esters, ethylhexyl-p-meth oxycinnamic acid ester, 2-ethoxyethyl-p-methoxycinnamic acid ester, Bu tylmethoxydibenzoylmethan and their mixtures.

In a preferred embodiment of the invention, the Dicarboxylic acid ester derivatives with a diacyloxypropyl radical conventional ceramides, pseudoceramides, cholesterol, cholesterol fatty acid esters, fatty acids, triglycerides, Ce rebrosides, phospholipids and similar substances, mixed become, whereby liposomes can arise.

In a further preferred embodiment of the invention can the dicarboxylic acid ester derivatives with a diacyloxypro pylrest with drug accelerators, especially with essential oils such as eucalyptol, menthol and similar can be mixed.

In a third preferred embodiment, the Dicar bonic ester derivatives with a diacyloxypropyl residue Lich also dissolved in squalene or squalane and if necessary with the other ingredients mentioned together with flüch term or non-volatile silicone compounds as anhydrous or formulated almost water-free single-phase systems. Further examples of components and typical combinations settlements can, for example, WO 90/01323 (Bernstein) and S.E. Friberg, J. Soc. Cosmet. Chem. 41, 155 (1990), taken from men.  

Industrial applicability

In the sense of the invention as "synthetic barrier lipids" dicarboxylic acid ester derivatives to be added with a diacyloxypro pylrest strengthen the skin's natural barrier function towards external stimuli. You improve strength, Ge suppleness and elasticity of the skin, increase the moisture content and protect the skin from dehydration; at the same time the finest wrinkles are smoothed.

Another object of the invention therefore relates to the Ver use of dicarboxylic acid ester derivatives with a diacyloxypro pyl residue of the formula I as a "synthetic barrier lipids" the provision of skin care products in which they are used in quantities of 1 to 50, preferably from 1 to 30, in particular from 2 to 10 % By weight, based on the composition, may be present. But also special formulations, the liquid crystalline, la Mellar structures are used to maintain the barrier function of the skin is particularly advantageous. These phrases can be based on the composition of the horny lipids as main components 5% by weight to 50% by weight of a compound with the formula I, 25 wt .-% to 75 wt .-% saturated and ung saturated fatty acids, their alkali salts or mixtures of fat acids and their salts, 10% by weight to 50% by weight of cholesterol, Phytosterols and / or cholesteryl sulfate, 5% to 30% by weight Triglycerides (triolein) and wax esters, and 2% by weight to 20 % By weight of phospholides, such as lecithins or cephalins. Typical examples of such formulations are skin creams, soft creams, nutritional creams, sunscreen creams, night creams, skin oils, skin care lotions and body aerosols.

The following examples are intended to be the subject of the invention explain in more detail without restricting it.  

Examples example 1 Succinic acid 1 (2), 3-distearoyloxy-2 (1) propyl ester-N-methyl sorbitylamid

To the stirred solution of 72.5 g (0.1 mol) of succinic acid mono-1 (2), 3-distearoyl-2 (1) propyl ester (obtained from equimo laren amounts of succinic anhydride and 1,3 (2) -distearoylgly cerin at 70 ° C) in 250 ml petrol (bp 65-90 ° C) was at Room temperature a solution of 8.3 g (0.06 mol) of phosphorus tri chloride in 30 ml of gasoline and the mixture for 3 hours this temperature and then stirred for 3 hours at 40 ° C. After the oily phosphorous acid settled, it became decanted, the solution concentrated and the colorless waxy The residue was dissolved in 250 ml of toluene. The solution was at 10 ° C with stirring with a solution of 21.5 g (0.11 mol) N-methylsorbitylamine (N-methylglucamine) and 41.5 g (0.3 mol) Potassium carbonate slowly added to 70 ml of water. The result The emulsion warmed to 15 ° C and was added after 100 ml of toluene at 30 ° C for 2 hours. Then was on 50 ° C heated (phase separation), the organic phase was separated, and the aqueous phase was 3 times with 100 ml of To luol washed. The combined organic phases were with Washed 1N hydrochloric acid and water and evaporated. There were 77 g (85% of theory) of a colorless waxy substance hold.  

Example 2 Succinic acid 1- (2), 3-distearolyoxy-2- (1) propyl ester-1,1- bishydroxymethyl-2-hydroxyethylamide

This compound was prepared analogously to Example 1 by instead of N-methylsorbitylamine 1,1-bishydroxymethyl-2-hy Droxyethylamine was used in the same molar ratios. The product was obtained as a colorless wax in a yield of 74.7 g (90% of theory) were obtained.

Example 3 Succinic acid mono-1 (2), 3-distearoyloxy-2 (1) -propyl ester- Oxyethylate (7.0 ethylene oxide units)

435.1 g (0.6 mol) of succinic acid mono-1 (2), 3-distearoyl-2 (1) propyl ester was treated with 2 g of lithium hydroxide and 200.6 g (4.6 Mol) of ethylene oxide for 8 hours at 180 ° C. and 5 bar nitrogen pressure touched. After cooling and evacuating the batch 184.8 g (4.2 moles) of ethylene oxide (7.0 ethylene oxide per mole) added been taken. After mixing with approx. 2% Tonsil® (Bleaching earth commercially available from Süd-Chemie AG, Munich) at 90 ° C 607.5 g (98% of theory) of a yellowish wax get like product.

Claims (10)

1. Dicarboxylic acid ester derivatives with a diacyloxypropyl radical with the formulas I or II in the
R¹ is a poly (C₂-C₃) alkylene oxide radical having 2 to 20 monomer units or an oligohydroxyalkyl radical having 2 to 8 carbon atoms and 1 to 6 hydroxy groups,
R² and R³ are the same or different and are a straight-chain or branched, saturated or unsaturated alkyl radical having 8 to 30 carbon atoms,
X represents a linear or branched alkylene radical with 1 to 6 carbon atoms, which can also be unsaturated and can be part of a ring system, oxygen, sulfur, the thionyl or sulfonyl group,
Y is oxygen or a group NR⁴, in which R⁴ represents a hydrogen atom, an alkyl radical having 1 to 4 carbon atoms or a hydroxyalkyl group having 2 to 4 carbon atoms. 2. Dicarboxylic acid ester derivatives with a diacyloxypropyl radical according to claim 1, characterized in that R¹ for a Oligohydroxyalkyl radical with 2 to 8 carbon atoms and 1 up to 6 hydroxyl groups, R² and R³ the same or different are and for a straight-chain or branched, sown saturated or unsaturated alkyl radical with 12 to 22 Koh lenstoffatomen, X for an alkylene group with 2 to 4 Carbon atoms and Y for a group NR⁴, wherein R⁴ for a hydrogen atom, an alkyl radical with 1 to 4 Koh lenstoffatomen or a hydroxyalkyl group with 2 to 4 Carbon atoms. 3. Dicarboxylic acid ester derivatives with a diacyloxypropyl radical according to claim 1 or 2, characterized in that R¹ for a polyethylene oxide residue with 4 to 12 monomer units ten, R² and R³ are the same or different and are for egg straight or branched, saturated or un saturated alkyl radical with 12 to 22 carbon atoms, X for an alkylene group with 2 to 4 carbon atoms and Y stands for oxygen. 4. Process for the preparation of dicarboxylic acid ester derivatives with a diacyloxypropyl radical having the general formula I and / or II in the
R¹ is a poly (C₂-C₃) alkylene oxide radical having 2 to 20 monomer units or an oligohydroxyalkyl radical having 2 to 8 carbon atoms and 1 to 6 hydroxy groups,
R² and R³ are the same or different and are a straight-chain or branched, saturated or unsaturated alkyl radical with 8 to 30 carbon atoms,
X represents a linear or branched alkylene radical with 1 to 6 carbon atoms, which can also be unsaturated and can be part of a ring system, oxygen, sulfur, the thionyl or sulfonyl group,
Y is oxygen or a group NR⁴, in which R⁴ represents a hydrogen atom, an alkyl radical having 1 to 4 carbon atoms or a hydroxyalkyl group having 2 to 4 carbon atoms,
mean, characterized in that one

• a) Diglycerides with the formulas III and / or IV with dicarboxylic acid anhydrides of the formula (V) wherein R², R³ and X have the meanings given above, acylated,
• b) the resulting acylation products are converted into their acid chlorides or mixed anhydrides in a manner known per se by means of chlorine compounds and
• c) the resulting acid chlorides or mixed anhydrides with compounds of the formula (VI) condenses R¹-YH (VI) wherein R¹ and Y have the meanings given above.

5. The method according to claim 4, characterized in that one uses dicarboxylic anhydrides of the formula V in which X represents alkylene groups with 2 to 4 carbon atoms. 6. The method according to any one of claims 4 or 5, characterized ge indicates that the diglycerides of the formulas III or IV and the dicarboxylic acid anhydrides in molar ver ratio 1: 0.9 to 1: 1.1. 7. The method according to any one of claims 4 to 6, characterized ge indicates that phosphorus tri chloride, thionyl chloride or chlorinated carbonate starts. 8. The method according to any one of claims 4 to 7, characterized ge indicates that the acylation products and Chlorine compounds or mixed and the compounds with formula VI in a molar ratio of 1: 0.9 to 1: 1.1 starts. 9. A process for the preparation of dicarboxylic acid ester derivatives with a diacyloxypropyl radical as claimed in claim 4, characterized in that the acylation products from step a) have the formulas IX or X with ethylene oxide in molar ratios of 1: 4 to 1:12. 10. Use of dicarboxylic acid ester derivatives with a Diacyloxypropylrest according to claim 1 as a component of "synthetic barrier lipids" for the production of skin care averaged.