DE10310523A1 - Use of ester polyol compounds as solvents, or solvent or dispersion aids in production of emulsions or dispersions containing organic compounds, pigments or pharmaceuticals, cosmetics, detergents, food or agrochemical agents - Google Patents

Abstract

Ester polyols that differ from
Glycerin, C _2-20 alkylene glycol, poly (C _2-20 alkylene) glycol, ethylene glycol, polyethylene glycol, preferably in which up to 30% of the ethyleneoxy units can be replaced by propyleneoxy units, polyglycerols, sorbitol, pentaerythritol, as the polyol component and
aliphatic C _3-6 carboxylic acids which, in addition to a carboxyl group, have at least one further functional group selected from hydroxyl and carboxyl groups, as the acid component
derived, or mixtures of the ester polyols with amino-functional polyols with a melting point of less than 100 ° C or ester polyols of the general formula (I)
R ¹ -O- [EO-] _n [PO-] _m R ²
with the meaning
R ¹ C _1-4 alkyl,
R ^{2 is} hydrogen or C _1-4 alkyl,
n on average 1 to 100,
m on average 0 to n / 2,
EO, PO basic building blocks derived from ethylene oxide and propylene oxide, which can exist in any order if both basic building blocks are present,
are used as solvents, solubilizers or dispersion aids for organic compounds, pharmaceutical, cosmetic, detergent technology, food technology or agricultural technology active ingredients that are insufficiently soluble or insoluble in lipophilic and hydrophilic media, and as a dispersion aid or continuous phase for (micro) pigment dispersions.

Description

The invention relates to the use of ester polyols as solvents or solution broker for in lipophilic and hydrophilic media insufficiently soluble or insoluble organic Compounds and as a dispersant for (micro) pigments. The invention also relates to ester polyol / ester polyol / polyol-in-oil emulsions (EP / O emulsions), process for their preparation, these emulsions containing ester polyo / polyol in oil in water emulsions (EP / O / W emulsions), their use in cosmetic and / or pharmaceutical and / or detergent technology and / or food technology and / or Agricultural technology drug compositions and such compositions.

In cosmetic and / or pharmaceutical and / or agro-active ingredient compositions, emulsions with active ingredients are often used, with which suitable compositions can be produced for the desired form of use. The production of polyol-in-oil emulsions and polyol-in-oil-in-water emulsions is known per se. Such emulsions can be used to convert cosmetic and / or pharmaceutical active ingredients into a form suitable for use. The DE-A-43 41 114 relates to anhydrous X / O emulsions which contain a non-aqueous, oil-immiscible phase and an oil phase. In the non-aqueous, oil-immiscible phase, an active ingredient, which can also be in the form of a solid, can be contained, for example, for medical, cosmetic or technical applications. The emulsion is made using a special emulsifier that has a maximum HLB of 6 or is a W / O emulsifier. Propylene glycol, butylene glycol, polyalkylene glycol, glycerin, polyglycerol and mixtures thereof are mentioned as usable polyol.

The DE-A-43 41 113 relates to a stable multiple emulsion of the X / O / Y type. X is an oil-immiscible component, O an oil phase and Y an aqueous phase.

In particular, W / O / W emulsions and P / O / W emulsions, with the polyol phase again Propylene glycol, butylene glycol, polyalkylene glycol, glycerin, polyglycerin or their mixtures can be used.

Numerous cosmetic or pharmaceutical or agro-active ingredients are not in hydrophilic and lipophilic media soluble. In particular, they are not soluble in water or oil. Such active substances can therefore often only in the form of finely divided dispersions of the solids in carrier media be applied, which has disadvantages in the formulation, dosage and application leads. The presence of solids results in complex formulations of cosmetic or pharmaceutical compositions. You can also Active ingredients often not be used in an appropriate form for an application.

Object of the present invention is the provision of cosmetic, pharmaceutical and agrotechnical acceptable solubilizers for in Hydrophilic and lipophilic media insufficiently soluble or insoluble active substances. Furthermore, polyol-in-oil emulsions are said be provided with a novel polyol replacement component, being the replacement component as a solubilizer for the Active ingredients can work. The disadvantages of the known drug formulations should be remedied. Alternative solid lipid Nanoparticle (SLN) systems are made available.

The object is achieved by the use of ester polyols, of glycerol, C _{2 -20} alkylene glycol is preferably, C _2-10 alkylene, in particular C _2-8 alkylene, for example propylene glycol, butylene glycol, and especially ethylene glycol, poly ( C ₂ glycol _-20 alkylene), preferably poly (C _{2 -10} alkylene) glycol, especially poly (C _{2- 8} alkylene) glycol having one or more different alkylene radicals, for example polyethylene glycol, in which up to 30% of ethyleneoxy units may be replaced by propyleneoxy units, polyglycerols, sorbitol, pentaerythritol, as the polyol component and aliphatic C ₃ _ ₆ carboxylic acids, which selected from hydroxyl and carboxyl groups, in addition to a carboxyl group at least one other functional group derived as the acid component, or mixtures of Ester polyols with amino-functional polyols with a melting point of less than 100 ° C or ester polyols of the general formula (I) R ¹ -O- [EO-] _n [PO-] _m R ² (I) with the meaning
R ^{1 is} C _1-4 alkyl,
R ^{2 is} hydrogen or C _1-4 alkyl,
n on average 1 to 100,
m on average 0 to n / 2
EO, PO basic building blocks derived from ethylene oxide and propylene oxide, which can exist in any order if both basic building blocks are present,
as a solvent, solubilizer or dispersion aid for organic compounds which are insufficiently soluble or insoluble in lipophilic and hydrophilic media, pharmaceutical, cosmetic, detergent technology, food technology or agricultural technology active ingredients and as a dispersion aid or continuous phase for (micro) pigment dispersions.

The ester polyols used in the invention are derived from polyol components and acid components that interact with each other are esterified. Glycerin, ethylene glycol, Polyethylene glycol in which up to 30% of the ethyleneoxy units pass through Propyleneoxy units can be replaced, and their mixtures for Commitment. The polyethylene glycol preferably contains 1 to 600, particularly preferably 1 to 100 ethyleneoxy units.

As the acid component, aliphatic carboxylic acids are C _{3 -6} used, in addition to a carboxyl group at least one further functional group selected from hydroxyl and carboxyl groups, having. The carboxylic acids preferably contain only carbon, hydrogen and oxygen as atoms. The carbon chain can be free of double bonds or contain a double bond. Examples of suitable acid components are lactic acid, maleic acid, tartaric acid and citric acid.

In the ester polyols, two, three or more, for example all hydroxyl groups of the polyol component present esterified. You can also one, two, more or all of the carboxyl groups of the acid component are in ester form.

The ester polyols used according to the invention can at room temperature (25 ° C) in solid, glass-like, more viscous or liquid Form. By mixing several ester polyols, the Properties can be set specifically. For example, lie Lactates are usually liquid before while Citrate in a glass-like Condition is present and only become viscous at a temperature of around 50 ° C. A 1: 1 mixture of citrate and lactate is similar to glass. A mixture of citrate and lactate in a weight ratio of 1: 2 is against it viscous. Are common the ester polyols are crystal clear and solid at room temperature.

The ester polyols can in Combination with amino functional polyols, ether alcohols or both connections are used. The proportion of ester polyols of such mixtures preferably at least 10% by weight, particularly preferably at least 15% by weight, in particular at least 20% by weight.

As an amino functional polyol any suitable amino functional polyol can be used, the one Melting point of less than 100 ° C, preferably less than 50 ° C having. The term "amino functional" polyols means that at least one amine group or amide group is present in the polyol. The polyol also has at least two hydroxyl groups. It can is an aliphatic, aromatic or aromatic / aliphatic Trade polyol. It is preferably an aliphatic Polyol. The polyol is particularly preferably 2 to 10, particularly preferably 2 to 5, in particular 2 to 3, hydroxyl groups. The amino functional polyols can be obtained via the mentioned functional groups, carbonyl groups, carboxyl groups, Thiol groups and carbon-carbon double bonds or - triple bonds exhibit. You can also have ether groups. Part of the hydroxyl groups present in the molecule can be etherified, provided that at least there are two free hydroxyl groups in the molecule. Preferably included those used according to the invention amino functional polyols one or two amide groups.

Amino-functional ones are preferred according to the invention Polyols used, the two or three hydroxyl groups and one or have two amide groups. You can also add one Have thiol group or carboxyl group. Preferably included the compounds 5 to 15 carbon atoms, particularly preferred 7 to 12 carbon atoms.

The amino-functional polyol is preferably a pantothene derivative of the general formula (II) HO-CH ₂ -C (CH ₃ ) ₂ -CH (OH) -CO-NH-CH ₂ -CH ₂ -R (II) with R COOR ¹ , CH ₂ -OR ¹ , CO-NH-CH ₂ -CH ₂ -SR ¹
R ¹ H, C _1-12 alkyl, phenyl.

R is preferably a CH ₂ -OR ¹ radical. Preferably, R ¹ is hydrogen or C _{1- 6} alkyl, in particular hydrogen or C _1-3 alkyl.

Pantothenic acid, panthenol are particularly preferred or Panthetein used. The pantothene derivatives are preferably located in the (R) -form. pantothenic acid can also be used in the form of the salts, especially preferred is the pantothen derivative (R) -panthenol.

The compounds preferably used according to the invention have a molecular segment on who is from pantoic acid derives, as well as a molecular section, which is different from β-alanine derives, provided it is a compound comparable to pantothenic acid is.

Panthenol and pantothenic acid are from the medical field for wound healing and from hair treatment agents and feed additives known. Manufacturing can be done via a biosynthesis from 2-oxo-3-methylbutanoic acid or from pantolactone. Other manufacturing processes are generally known. It can also on Beilstein EIV 4, 2571, Beilstein EV 18/1, 22 and Beilstein E IV 4, 2569f and Isler et al., Vitamine II, pages 309 to 339, Thieme-Verlag, Stuttgart, 1988. There is also one extensive Patent literature dealing with the use of pantothene derivatives, especially of panthenol in cosmetic and pharmaceutical Compositions deals.

Basic building blocks derived from ethylene oxide and optionally additionally from propylene oxide may be present in the ester polyols of the general formula (I). These basic building blocks have the structures -CH ₂ -CH ₂ -O-, -CH ₂ -CH (CH ₃ ) -O- and -CH (CH ₃ ) -CH ₂ -O-. If the two basic building blocks derived from ethylene oxide and propylene oxide are present, they can be in any order. This means that one or more blocks derived from ethylene oxide and propylene oxide can be connected to one another. Furthermore, the units derived from ethylene oxide and propylene oxide can also be present alternately or statistically. The continuous transitions possible between these forms are also possible according to the invention.

In the general formula (I) the proportion of the basic building blocks derived from propylene oxide is a maximum Fraction of the amount of basic building blocks derived from ethylene oxide. While on average 1 to 100, preferably 2 to 70, particularly preferred 3 to 50, in particular 5 to 15 basic building blocks derived from ethylene oxide are 0 to n / 2, preferably 0 to n / 4, particularly preferred 0 to n / 8 propylene oxide derived building blocks on average in front. If there are basic building blocks derived from propylene oxide, is yours Amount preferably n / 10 to n / 4, particularly preferably n / 8 to n / 5. The numbers n and m are mean values, since at the alkoxylation usually a distribution of the degree of alkoxylation established. Therefore, odd-numbered values for n and m possible. The breadth of the distribution of the degree of alkoxylation depends on other also from the alkoxylation catalyst used. It is also possible discrete Degrees of alkoxylation or very narrow distributions of the degree of alkoxylation adjust.

R ¹ is a C _1-4 alkyl, C _{1- 3} preferably alkyl, more preferably C _{1- 2} alkyl, in particular methyl. Propyl residues include n-propyl and iso-propyl, while butyl residues include n-butyl, iso-butyl, tert-butyl.

R ^{2 represents} hydrogen or a radical as defined above for R ¹ . The meaning of R ^{2 is} independent of the meaning of the radical R ¹ . R ² is particularly preferably hydrogen. The term "ester polyol" used in the description and the claims includes all compounds of the general formula (I), ie also the cases in which R ^{2 is} not a hydrogen atom and thus there are no free hydroxyl groups in the molecule.

The ester polyol is preferred a methanol ethoxylate with 5 to 15 ethylene oxide units.

Polyethylene glycol monomethyl ether is particularly preferred (12EO) and polyethylene glycol monomethyl ether (7EO) are used. in this connection it is pure methyl alcohol ethoxylates. Such connections are known per se and have hitherto been closed for the preparation of methyl end groups Fettsäurepolyethylenglykolestern used. The connections are commercially available.

According to the invention are particularly preferred Ester polyols of the general formula (I) used at room temperature (25 ° C) are liquid.

The term "ester polyol / polyol" as used to describe ester polyol / polyol-in-oil emulsions (EP / O), ester polyol / polyol phases and ester polyol / polyol in oil in water emulsions (EP / O / W) indicates that an ester polyol phase or a mixed ester polyol / palyol phase can be present. The corresponding carrier phase is either only by the ester polyols of the general formula (I) formed, or there are mixtures of the ester polyols with polyols, Ether alcohols, or amino functional polyols. In addition, how described below, organic or inorganic compounds are in the ester polyol / polyol phase.

In the ester polyol / polyol-in-oil emulsions according to the invention (EP / O emulsions) can one or more ester polyol / polyol phases are present. Preferably there is an ester polyol / polyol phase which is at least one as above contains described ester polyol. Preferably there are at least 10 or at least in the polyol phase 50% by weight, particularly preferably at least 80% by weight, in particular at least 95% by weight of the ester polyol, based on the total Ester polyol / polyol. In the ester polyol / polyol phase too Water in an amount of at most 20% by weight, preferably at most 10 wt .-%, in particular a maximum of 5 wt .-% contained on the entire ester polyol / polyol phase. The ester polyol / polyol phase is preferred largely or completely anhydrous. The sum of ester polyol, optionally ether alcohol, amino functional polyol, other polyol and water 100% by weight.

The customary known polyols such as propylene glycol, butylene glycol, ethylene glycol, polyalkylene glycol, glycerol, polyglycerol, glycosides, sorbitol, mannitol, pentaerythritol, trimethylolpropane or mixtures thereof can be present as polyols. Polyalkylene glycols include, in particular, polyethylene glycol and polypropylene glycol in question. Other suitable polyols are known to the person skilled in the art, for example aromatic polyols such as Emodin / Aloe Vera. These polyols can also be the basis of the above ester polyols.

Particularly preferred are in the Ester polyol / polyol phase only ester polyols as described above are.

According to the invention, the ester polyol / polyol phase is not with oil miscible. This means that preferred in the preparation of the EP / O emulsions according to the invention no ester polyol / polyol in the oil phase dissolves or oil in the Ester polyol / polyol phase dissolves.

Minor deviations from this (approx up to 5% by weight, preferably up to about 1% by weight, in particular up to about 0.5% by weight solubility) are irrelevant here. It depends on that in the EP / O emulsion receive an emulsion of the ester polyol / polyol phase in the oil phase will and not a solution of the ester polyol / polyol in the oil.

As oil in the oil phase everyone can known suitable oils and their mixtures are used. Examples of suitable oils are silicone oils and derivatives thereof, which can be linear or cyclic, natural ester oils such as grape seed oil, olive oil or sunflower oil, synthetic Esteröle like neutral oils, which can be linear or branched paraffin oils and isoparaffin oils, Esteröle, for example the citrates, lactates, aleates, salicylates, cinnamates or other organic light protection filters, or camphor derivatives, Triglycerides, fatty alcohols or mixtures thereof.

In the EP / O emulsions the weight ratio is from Ester polyol / polyol phase to oil phase preferably 10:90 to 90:10, particularly preferably 25:75 to 75:25 and especially 40:60 to 60:40.

Any suitable emulsifiers can be used as emulsifiers are used to produce an emulsion of the ester polyol / polyols suitable in oil are. Examples of suitable emulsifiers are glycerol esters, polyglycerol esters, Sorbitan esters, sorbitol esters, fatty alcohols, propylene glycol esters, Alkyl glucose esters, sugar esters, lecithin, silicone copolymers, wool wax and their mixtures or derivatives. Glycerol esters, polyglycerol esters, Alkoxylates and fatty alcohols as well as iso alcohols can be derived, for example of castor fatty acid, 12-hydroxystearic acid, Isostearic acid, oleic acid, linoleic acid, linolenic acid, stearic acid, myristic acid, lauric acid and Capric acid. In addition to the esters mentioned succinates, amides or ethanolamides of the fatty acids are also present. As fatty acid alkoxylates come in particular the ethoxylates, propoxylates or mixed Ethoxylates / propoxylates into consideration.

The amount of emulsifier can be adapted to practical requirements. Preferably the emulsifier in an amount of 0.1 to 20 wt .-%, particularly preferred 0.5 to 15 wt .-%, in particular 1 to 8 wt .-%, based on the entire EP / O emulsion used. In some cases, different doses may be used to be required.

According to one embodiment the esterpolyol / polyol phase or the esterpolyol solution or -Dispersion of a cosmetic and / or dissolved in the phase Contain pharmaceutical active ingredient or perfumes, perfume oils or flavors. It can also be a detergent technology, food technology act or agro-technological (agro) active ingredient.

The active ingredients are preferably inadequate in lipophilic and hydrophilic media soluble especially insoluble ones organic compounds. The connections are particularly in Water and oil insufficiently soluble or insoluble. It can any suitable active ingredients are used, provided they are in the ester polyol or the ester polyol / polyol phase containing the ester polyol to solve. Suitable active ingredients are, for example, dichlophenac, ibuprofen, acetylsalicylic acid, salicylic acid, Erythromycin, ketoprofen, cortisone, glucocorticoids.

Cosmetics are also suitable Active ingredients that are particularly sensitive to oxidation or hydrolysis are such as polyphenols. Catechins are mentioned here (such as epicatechin, epicatechin-3-gallate, epigallocatechin, epigallocatechin-3-gallate), Flavonoids (such as luteolin, apigenin, rutin, quercitin, fisetin, kaempherol, Rhametin), isoflavones (such as genistein, daidzein, glycitein, prunetin), Coumarins (such as daphnetin, umbelliferone), Emodin, Resveratrol, Oregonin.

Vitamins such as retinol, Tocopherol, ascorbic acid, Riboflavin, pyridoxine.

Total extracts are also suitable from plants that above molecules or classes of molecules contain.

The active ingredients are according to one embodiment the invention around light protection filters. These can be used as organic light protection filters at room temperature (25 ° C) in liquid or solid form. Suitable light protection filters (UV filters) are, for example, compounds based on benzophenone, diphenyl cyanoacrylate or p-aminobenzoic acid. Specific examples are (INCI or CTFA names) Benzophenone-3, Benzophenone-4, Benzophenone-2, Benzophenone-6, Benzophenone-9, Benzophenone-1, Benzophenone-11, Etocrylene, Octocrylene, PEG-25 PABA, phenylbenzimidazole sulfonic acid, ethylhexyl methoxycinnamate, Ethylhexyl dimethyl PABA, 4-methylbenzylidene camphor, butyl methoxydibenzoylmethane, Ethylhexyl salicylates, homosalates and methylene-bis-benzotriazolyl Tetramethylbutylphenol (2,2'-methylene-bis- {6- (2H-benzoetriazol-2-yl) -4- (1,1,3,3-tetramethylbutyl) phenol}, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and 2,4,6-trianilino-p- (carbo-2'-ethylhexyl-1'-oxi) -1,3,5-triazine.

More organic light protection filters are octyltriazone, avobenzone, octylmethoxycinnamate, octylsalicylate, Benzotriazoles and triazines.

The ester polyols can also as a mediator and / or dispersant for Antidandruff agents are used.

According to a further embodiment anti-dandruff active ingredients are used as active ingredients of the invention, like they usually do present in cosmetic or pharmaceutical formulations. An example of this is Piroctone oil amines (1-hydroxy-4-methyl-6- (2,4,4-dimethylpentyl) -2 (1H) pyridone; preferably in combination with 2-aminoethanol (1: 1)). Other suitable means for treating skin flakes are known to the person skilled in the art.

According to a further embodiment The invention uses organic dyes as active ingredients or Substances used.

Any suitable amount can be used of the active ingredient are introduced into the ester polyol / polyol phase. The amount that can be brought in is frequent through solubility and determined by the ultimate application of the preparation. As a rule, 0.01 to 95% by weight, preferably 0.1 to 80 % By weight, in particular 2 to 50% by weight, of the active ingredient in the ester polyol or introduced the ester polyol / polyol phase, the proportion by weight refers to the sum of active ingredient and ester polyol / polyol. Different expressed can in the amount of the ester polyol / polyol phase the stated proportion by weight of ester polyol / polyol by the active ingredient to be replaced. For example, based on the pure ester polyol / polyol phase, 0.01 to 95 wt .-% of the ester polyol / polyol phase be replaced by the active ingredient. This means that the above versions the proportion of the ester polyol / polyol phase in the emulsion continues stay true. The content of ester polyol / polyol or ester polyol then just decreases by the proportion of active ingredient, which then is in the ester polyol / polyol phase.

It is also possible to use a conventional carrier system for the active ingredient with the ester polyol replenish, to get to the mentioned ester polyol / polyol phase.

The EP / O emulsion or dispersion described above can also be emulsified in water or a water-in-oil emulsion. The result is an ester polyol / polyol-in-oil-in-water emulsion (EP / O / W emulsion) which contains at least one emulsion as described above and additionally at least one aqueous phase. Such multiple emulsions can be built up in DE-A-43 41 113 correspond to the emulsions described, the polyol component being varied in the manner according to the invention. The structure of the ester polyol / polyol-in-oil emulsion can be the structure of the in DE-A-43 41 114 correspond to the emulsions described, the ester polyol / polyol phase according to the invention being used as the polyol phase.

When introducing the EP / O emulsion according to the invention in water or watery Systems can the weight ratio of the individual phases can be varied over a wide range. Preferably is the weight fraction in the EP / O / W emulsion ultimately obtained the EP / O emulsion 0.01 to 80 wt .-%, particularly preferably 0.1 to 70% by weight, in particular 1 to 30% by weight, based on the total EP / O / W emulsion.

When introducing the EP / O emulsion according to the invention in an O / W emulsion the proportion of the EP / O emulsion preferably 0.01 to 60% by weight, particularly preferably 0.1 to 40% by weight, in particular 1 to 30% by weight, based on the EP / O / W emulsion ultimately obtained. In the O / W emulsion, which is used for this the oil content preferably 1 to 80% by weight, particularly preferably 1 to 30% by weight, based on the O / W emulsion used.

The individual phases of the emulsions can also have the usual ingredients known for the individual phases. For example, the individual phases can contain further pharmaceutical or cosmetic active ingredients that are soluble in these phases. The aqueous phase can contain, for example, organic soluble light protection filters, hydrophilically coated micropigment, electrolytes, alcohols, etc. Some or all of the phases can also contain solids, which are preferably selected from pigments or micropigments, microspheres, silica gel and similar substances. The oil phase can contain, for example, organically modified clay minerals, hydrophobically coated (micro) pigments, organic oil-soluble light protection filters, oil-soluble cosmetic active ingredients, waxes, metal soaps such as magnesium stearate, petroleum jelly or mixtures thereof. Titanium dioxide, zinc oxide and barium sulfate as well as wollastonite, kaolin, talc, Al ₂ O ₃ , bismuth oxychloride, micronized polyethylene, mica, ultramarine, eosin colors, azo dyes can be mentioned as (micro) pigments. In particular, titanium dioxide or zinc oxide are used in cosmetics as light protection filters and can be applied to the skin particularly smoothly and evenly by means of the emulsions according to the invention. Microspheres or silica gel can be used as carriers for active ingredients, and waxes can be used, for example, as the basis for polishes.

The ester polyols according to the invention can also be used as dispersants or continuous phase for (micro) pigment dispersions. Such systems of ester polyols and (micro) pigments according to the invention typically contain 10 to 50% by weight of (micro) pigments, particularly preferably 35 to 45% by weight of (micro) pigments. The dis. Available from the (micro) pigments and the ester polyols Persions can be introduced into water or oil without affecting the dispersion. By using the ester polyols, it is thus possible to hydrophobize hydrophilic pigments and to introduce them into an oil phase without the degree of dispersion deteriorating. The invention thus also relates to a dispersion of (micro) pigments and / or insoluble organic compounds in ester polyols.

The water phase can go beyond that Glycerin, polyethylene glycol, propylene glycol, ethylene glycol and the like Contain compounds and derivatives thereof.

In a corresponding way you can also medicines that are administered orally, but among those in the stomach prevailing conditions are not stable or in other places of the digestive tract should come into effect with an emulsion according to the invention bring to their place of action. This emulsion or dispersion will not broken in the stomach, so she the stomach unchanged happens. The active ingredient contained is therefore only in the following The digestive tract is released by breaking down or dissolving the emulsifier. The choice of emulsifiers can be based on those at the sites of action existing conditions can be set.

The use of usual Auxiliaries and additives in the emulsions or dispersions known to the expert.

The EP / O emulsions or dispersions according to the invention can be prepared by known processes, as described, for example, in DE-A-43 41 114 and DE-A-43 41 113 are described. For the preparation, the ester polyol / polyol phase and the oil phase, which can each contain emulsifier, are usually heated separately to a temperature in the range from 20 to 90 ° C. and then combined with stirring.

The emulsions or dispersions can dependent on of the composition, the phase volume ratio and, if applicable existing solid content as solid or flowable emulsions or dispersions are manufactured and available. It is very stable emulsions or dispersions used under normal handling conditions high long-term stability exhibit. You meet especially the usual ones stability requirements in the temperature range of -5 ° C up to + 45 ° C. The droplets or in the emulsion or dispersion Particles are very stable, which is why the emulsions or dispersions, in particular as carriers for many Types of active substances are suitable.

With the help of the emulsifiers mentioned emulsions or dispersions can be prepared by a simple Mixing with stirring are obtained, the stability of the emulsions or dispersions through the entered agitator energy and the type of stirrer usually hardly or not influenced. To make the emulsion according to the invention or dispersion, any suitable commercially available agitator can be used.

The invention also relates to an ester polyol-in-oil dispersion containing ester polyol particles in oil as the dispersant, which are derived from glycerol, ethylene glycol, polyethylene glycol, in which up to 30% of the ethyleneoxy units can be replaced by propyleneoxy units, as the polyol component and aliphatic C _{3- 6-} carboxylic acids, which in addition to a carboxyl group have at least one further functional group selected from hydroxyl and carboxyl groups, are derived as acid components, which are solid or glassy at 25 ° C., with an average particle size in the range from 10 to 10,000 nm, at least an emulsifier which forms lamellar structures, the ester polyol particles being able to contain a pharmaceutical, cosmetic, detergent-technological, food-technological and / or agricultural-technological active ingredient dissolved or dispersed in the phase.

This dispersion is, in particular, an SPN dispersion (solid polyol nanoparticles) analogous to an SLN dispersion (solid lipid nanoparticles), the lipid phase being replaced in whole or in part by the solid ester polyols used according to the invention and working in oil instead of water. The structure and manufacture of the SPN dispersion according to the invention is shown, for example, in EP-B 0 605 497 and EP-B 0 167 825 described. The dispersion can be prepared as described there, and the dispersion can contain the pharmaceutically active substances described.

According to one embodiment of the invention, the dispersion is prepared by mechanically mixing the ester polyol phase with an oil phase at a temperature above the melting or softening point of the ester polyol, the weight ratio of ester polyol phase to oil phase being 1: 5 to 5: 1, preferably 2: 1 to Is 1: 2. The mixing is preferably carried out without high-pressure homogenization using stirrers in which the shear effect corresponds to the shear effect of a household stirrer. The mixed phase thus obtained can then be further diluted with oil until a desired degree of dispersion is achieved. Suitable emulsifiers for the preparation of the dispersion are in turn EP-B 0 605 497 or EP-B 0 167 825 described. The average particle diameter in the solid ester polyol phase is preferably 40 to 1000 nm.

The oil phase can be the usual for SPN dispersion Contain additives such as gelling agents, cross-polymers, cellulose derivatives, Xanthan gum, gelatin or pectins. Other ingredients are known to the expert.

The emulsions or dispersions according to the invention are preferably used in cosmetic and / or pharmaceutical and / or active ingredient compositions. The invention also relates to this cosmetic and / or pharmaceutical and / or agro-active ingredient compositions of this type which contain at least one of the emulsions mentioned. The cosmetic and / or pharmaceutical compositions can be hand or body lotions, oils, ointments, pastes, gels, lip care products, face care products and similar compositions. The compositions can be used in solid, liquid or aerosol form.

The invention further relates to the Use of the ester polyols as solvents, solubilizers or Dispersing aids for Slightly soluble (<10% solubility) or insoluble organic in lipophilic and hydrophilic media Links. Suitable molecules or molecular groups are, for example, salicylic acid, Sphingosines, ceramides, triterpenic acid such as oleanolic acid, betulinic acid, betulin, ursolic acid, boswellic, 18-β-glycyrrhetinic acid, forskolin, Sclareolid, andrographolide.

Total extracts are also suitable from plants that above molecules or classes of molecules contain.

Here come as lipophilic media the aforementioned oils considered as hydrophilic media aqueous media with a water content of at least 80, preferably at least 90, in particular at least 95% by weight. As insoluble Compounds are considered whose solubility is below 3%, preferably below 1%, in particular less than 0.5%.

The invention also relates to a solution of organic compounds insoluble in lipophilic and hydrophilic media in ester polyols constructed as defined above.

The invention further relates to the Use of ester polyols as solubilizers for the introduction of cosmetic and / or pharmaceutical and / or agro-active ingredients in polyol-in-oil emulsions or polyol-in-oil-in-water emulsions or corresponding dispersions.

The emulsions or dispersions according to the invention can for the Active substances contained therein have a transport and a depot effect demonstrate. You can thus acting not only as a carrier but also as a depot, which over one determine a delayed period Allow release of the active ingredient.

The emulsions or dispersions according to the invention show the following advantages: oxidation sensitive and hydrolysis sensitive Active ingredients can stable and especially about a longer one Period encapsulated to be stable in storage. The moisture attack the active ingredients can with the emulsions and dispersions of the invention reliable be prevented.

In hydrophilic and lipophilic media insoluble Active ingredients can be presented in the form of an emulsion or dispersion.

The penetration properties of the cosmetic or pharmaceutical compositions can by Use of the emulsions according to the invention positively influenced become. In particular, in the multiple emulsions described, a Depot effect and improved penetration can be achieved.

Overcoming the skin's permeability barrier is achieved in that Training liquid crystalline Gel network structures in the described multiple emulsions a state of order is built up that that of the lipid barrier Skin corresponds. In such a carrier system, the penetration properties of the pharmacological and cosmetic active ingredients mentioned improved. The same applies to the dispersions.

The invention is illustrated by the examples below.

Example 1 Phase A DGCL-Citrate 30.00 GLC Lactate 30.00 ascorbic acid 10:00

Phase B Dow Corning DC 5225 C Formulation Aid 15.00 Abil EM 97 10.00 Wacker Belsil CM 040 5.00 totally 100.00

production:
Heat phases A and B separately to 65 ° C;
Stir phase A until the ascorbic acid is dissolved;
Add phase A slowly to phase B while stirring;
Homogenize until a droplet size below 450 nm is reached;
Cool the batch to room temperature.

Example 2 Phase A PEG 6000 15:00 Glycerinlactat 40.00 ascorbic acid 10:00

Phase B

Dow Corning DC 5225 C Formulation Aid 15.00 Abil EM 97 10.00 brave Belsil CM 040 10.00 total 100.00

production:
Heat phases A and B separately to 65 ° C;
Stir phase A until the ascorbic acid is dissolved;
Add phase A slowly to phase B while stirring;
Homogenize until a droplet size below 450 nm is reached;
Cool the batch to room temperature.

Example 3 Phase A PEG 6000 40.00 retinol 5:00 Polysorbate 20 5:00

Phase B Dow Corning DC 5225 C Formulation Aid 25.00 Abil EM 97 10.00 Wacker Belsil CM 040 15.00 totally 100.00

production:
Heat phases A and B separately to 65 ° C;
Stir phase A until the retinol is dissolved;
Add phase A slowly to phase B while stirring;
Homogenize until a droplet size below 450 nm is reached;
Cool the batch to room temperature.

Example 4 Phase A DGCL-Citrate 25.00 GLC Lactate 35.00 polyphenols 10:00

Phase B Dow Corning DC 5225 C Formulation Aid 15.00 Abil EM 97 10.00 Wacker Belsil CM 040 5.00 totally 100.00

production:
Heat phases A and B separately to 65 ° C;
Stir phase A until the polyphenol is dissolved;
Add phase A slowly to phase B while stirring;
Homogenize until a droplet size below 450 nm is reached;
Cool the batch to room temperature.

Claims (13)

Use of ester polyols, of glycerol, C _2-20 alkylene glycol, poly is (C _2-20 -alkylene) glycol, preferably ethylene glycol, polyethylene glycol, can be in up to 30% of ethyleneoxy replaced by propyleneoxy units, polyglycerols, sorbitol, pentaerythritol, as the polyol component and aliphatic C _{3 - 6} carboxylic acids, in addition to a carboxyl group at least one further functional group selected from hydroxyl and carboxyl groups, are derived as the acid component, or mixtures of ester polyols with amino-functional polyols having a melting point of less than 100 ° C or ester polyols of the general formula (I) R ^I -O- [EO-] _n [PO-] _m R ² (I) with the meaning R ¹ C _1-4 alkyl, R ² hydrogen or C _1-4 alkyl, n on average 1 to 100, m on average 0 to n / 2 EO, PO derived from ethylene oxide and propylene oxide basic building blocks, which in Both basic building blocks can be present in any order, as solvents, solubilizers or dispersing agents for organic compounds which are insufficiently soluble or insoluble in lipophilic and hydrophilic media, pharmaceutical, cosmetic, detergent technology, food technology or agricultural technology agents and as dispersing agents or continuous phase for (micro) pigment dispersions. Solution of insufficiently soluble in lipophilic and hydrophilic media, or insoluble organic compounds in ester polyols which may be located, in which up to 30% of ethyleneoxy replaced by glycerol, ethylene glycol, polyethylene glycol by propyleneoxy, as the polyol component and aliphatic C _{3 - 6} carboxylic acids, which, in addition to a carboxyl group, have at least one further functional group selected from hydroxyl and carboxyl groups, are derived as the acid component, or mixtures of the ester polyols with amino-functional polyols with a melting point of less than 100 ° C. or ester polyols of the general formula (I) R ¹ -O- [EO-] _n [PO-] _m R ² (I) with the meaning R ¹ C _1-4 alkyl, R ² hydrogen or C _1-4 alkyl, n on average 1 to 100, m on average 0 to n / 2 EO, PO derived from ethylene oxide and propylene oxide basic building blocks, which in Both basic building blocks can be present in any order. Dispersion of (micro) pigments and / or insoluble organic compounds in ester polyols, which are derived from glycerol, ethylene glycol, polyethylene glycol, in which up to 30% of the ethyleneoxy units can be replaced by propyleneoxy units, as the polyol component and aliphatic C _{3 - 6} carboxylic acids in addition to a carboxyl group, have at least one further functional group selected from hydroxyl and carboxyl groups, derived as an acid component, or mixtures of the ester polyols with amino-functional polyols with a melting point of less than 100 ° C. or ester polyols of the general formula (I) R ¹ -O- [EO-] _n [PO-] _m R ² (I) with the meaning of R ^{1 is} C _1-4 alkyl, R ² is hydrogen or C _{1- 4} alkyl, n is on average 1 to 100, m is on average from 0 to n / 2 EO, PO of ethylene oxide and propylene derived basic building blocks in the Both basic building blocks can be present in any order. Use of ester polyols which, ethylene glycol, polyethylene glycol, can be up to 30% of ethyleneoxy replaced in the through propyleneoxy from glycerol, as a polyol component and aliphatic C _{3 - 6} carboxylic acids, in addition to a carboxyl group at least one further functional group selected from Have hydroxyl and carboxyl groups, derived as acid component, or mixtures of the ester polyols with amino-functional polyols with a melting point of less than 100 ° C. or ester polyols of the general formula (I) R ¹ -O- [EO-] _n [PO-] _m R ² (I) with the meaning R ¹ C _1-4 alkyl, R ² hydrogen or C _1-4 alkyl, n on average 1 to 100, m on average 0 to n / 2 EO, PO derived from ethylene oxide and propylene oxide basic building blocks, which in Both basic building blocks can be present in any order, as solubilizers for the introduction of cosmetic and / or pharmaceutical and / or detergent technology and / or food technology and / or agricultural technology active ingredients in polyol-in-oil emulsions or dispersions or polyol-in-oil in water emulsions or dispersions. Ester polyol / polyol-in-oil emulsion or dispersion containing ester polyols which, polyethylene glycol, may be derived from glycerol, ethylene glycol, be in up to 30% of ethyleneoxy replaced by propyleneoxy, as the polyol component and aliphatic C _{3 - 6} carboxylic acids which, in addition to a carboxyl group, have at least one further functional group selected from hydroxyl and carboxyl groups, are derived as the acid component, or mixtures of the ester polyols with amino-functional polyols with a melting point of less than 100 ° C. or ester polyols of the general formula (I) R ¹ -O- [EO-] _n [PO-] _m R ² (I) with the meaning R ¹ C _1-4 alkyl, R ² hydrogen or C _1-4 alkyl, n on average 1 to 100, m on average 0 to n / 2 EO, PO of basic units derived from ethylene oxide and propylene oxide, which in Both basic building blocks can be present in any order, in an oil-immiscible ester polyol / polyol phase, an oil phase and at least one emulsifier. Emulsion or dispersion according to claim 5, characterized characterized that as acid component in the ester polyols lactic acid, maleic acid, tartaric acid or citric acid be used. Emulsion or dispersion according to claim 6, characterized characterized that the Ester polyols at 25 ° C solid or glassy and an average particle size in the range can have from 10 to 10,000 nm. Emulsion or dispersion according to any one of claims 5 to 7, characterized in that in the ester polyol / polyol phase at least 50 wt .-% ester polyol are present. Emulsion or dispersion according to any one of claims 5 to 8, characterized in that the ester polyol / polyol phase solved in the phase cosmetic and / or pharmaceutical and / or detergent technology and / or active ingredient in food technology and / or agricultural technology contains. Process for the preparation of emulsions or dispersions according to one of the claims 5 to 9, characterized in that the ester polyol / polyol phase and the oil phase, which can each contain emulsifier, separated to a temperature in the range of 20 to 90 ° C heated and subsequently combined with stirring become. Ester polyol / polyol-in-oil-in-water emulsion or dispersion, containing at least one emulsion or dispersion according to one of claims 5 to 9 and additionally at least one aqueous Phase. Use of emulsions or dispersions according to one of claims 5 to 9 or 11 in cosmetic and / or pharmaceutical and / or detergent technology and / or food technology and / or agro-technological active ingredient compositions. Cosmetic and / or pharmaceutical and / or detergent technology and / or food technology and / or agricultural technology Active composition, containing at least one emulsion or dispersion according to one of claims 5 to 9 or 11.