The invention relates to polyglycerol partial esters of polyricinoleic acid and polyfunctional carboxylic acids, obtainable by esterification of a a) polyglycerol mixture with b) at least one polyricinoleic acid and c) at least one di- and/or tricarboxylic acid and optionally d) at least one fatty acid having 6 to 22 carbon atoms by methods known per se, and to the use thereof for producing cosmetic or pharmaceutical emulsions or dispersions.

Description of the Invention

SUMMARY OF THE INVENTION

Surprisingly, it has now been found that very low-viscosity, light water-in-oil emulsions can be obtained using emulsifiers based on polyglycerol partial esters of polyricinoleic acid which are additionally linked via di- or tricarboxylic acids. These linked polyglycerol polyricinoleates have neither a greasy-rancid odor, nor do they exhibit a greater sensitivity to oxidation than polyglycerol polyhydroxystearates. Using the inventive emulsifiers it is possible, in contrast to uncrosslinked polyglyceryl ricinoleates and polyhydroxystearates, to formulate emulsions with considerably lower viscosity. This makes it possible to formulate lotions with a very low oil phase content (<22% by weight) which have a correspondingly light feel on the skin.

The present invention therefore provides polyesters of polyricinoleic acid and polyfunctional carboxylic acids, obtainable by esterification of a) a polyglycerol mixture with b) at least one polyricinoleic acid of the general formula 1 -- see Original Patent.

The invention further provides polyesters of polyricinoleic acid and polyfunctional carboxylic acids, obtainable by esterification a) of a polyglycerol mixture with b) at least one polyricinoleic acid of the general formula 1 -- see Original Patent.

The present invention further provides polyglycerol partial esters as disclosed herein, prepared by esterification of a) 1.0 mol of OH groups of the polyglycerol mixture with b) 0.01 to 0.5 mol, in particular 0.05 to 0.3 mol, of COOH groups of the polyricinoleic acid, and c) 0.01 to 0.5 mol, in particular 0.05 to 0.3 mol, of COOH groups of at least one di- and/or tricarboxylic acid, and d) 0.01 to 0.9 mol, in particular 0.1 to 0.6 mol, of COOH groups of the fatty acids having 6 to 22 carbon atoms, with the proviso that the sum of the COOH groups corresponds to about 20 to 75% of the OH groups of the polyglycerol mixture.

The present invention further provides cosmetic, dermatological or pharmaceutical preparations which comprise at least one of the polyglycerol partial esters according to the instant invention. These preparations are preferably emulsions which can optionally comprise dispersed solids. In particular, the use of the polyglycerol partial esters according to the invention as water-in-oil emulsifiers or dispersion auxiliaries is at the forefront here.

The invention further provides care and cleaning compositions for household and industry, in particular for hard surfaces, for leather or textiles, which comprise at least one of the polyglycerol partial esters according to the present invention. These preparations are preferably emulsions which can optionally comprise dispersed solids. In particular, the use of the polyglycerol partial esters as water-in-oil emulsifiers or dispersion auxiliaries is at the forefront here.

DETAILED DESCRIPTION OF THE INVENTION

The present invention, which relates to polyglycerol partial esters of polyricinoleic acid and polyfunctional carboxylic acids, will now be described in greater detail by referring to the following discussion.

Before discussing the invention in detail, it is noted that the condensation products based on ricinoleic acid according to the present invention are liquid and are thus also suitable for the energy-saving "cold-cold" preparation of emulsions besides the classic "hot-hot" preparation.

The polyricinoleic acids co-used according to the invention are prepared in accordance with the known methods of the prior art, for example, by polycondensation of ricinoleic acid, optionally with co-use of hydroxystearic acid.

Esterification products of the general formula 1 -- see Original Patent.
According to the present invention, it is also possible to use mixtures of polyricinoleic acid and polyhydroxystearic acid.

Suitable polyglycerols are, in particular, those of the general formulae 2A and 2B -- see Original Patent.

These are technical-grade polyglycerol mixtures which are obtained, for example, by alkali-catalyzed condensation of glycerol at elevated temperatures, from which it is possible to obtain fractions with the desired degree of condensation, if appropriate, through distillation processes. Likewise, of suitability, are also polyglycerols which are obtained in another way, e.g., from epichlorohydrin or glycidol.

It has proven particularly advantageous to use polyglycerols which have the following homolog distribution (GC method); the preferred ranges are given in brackets: Glycerol: 0 to 20 (<5) % by weight Diglycerols: 0 to 60 (5 to 30) % by weight Triglycerols: 0 to 60 (5 to 50) % by weight Tetraglycerols: 0 to 30 (5 to 25) % by weight Pentaglycerols: 0 to 30 (5 to 20) % by weight Oligoglycerols: ad 100% by weight

Of particular suitability for the intended use according to the present invention, as emulsifiers, is the use of relatively short-chain di- or tricarboxylic acids, such as, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, or dodecanedioic acid. Hydroxydi- and tricarboxylic acids, such as, malic acid, tartaric acid, or citric acid, are likewise suitable. Furthermore, aromatic acids, such as, phthalic acid, isophthalic acid or terephthalic acid, can be used.

The dimeric fatty acids optionally co-used to prepare the compounds according to the present invention are standard commercial products which are prepared by polymerization of saturated or unsaturated natural or synthetic monobasic aliphatic fatty acids having 16 to 22 carbon atoms in accordance with known methods (see, for example, U.S. Pat. No. 2,482,761, and U.S. Pat. No. 3,256,304). Typical commercially available dimeric fatty acids have, for example, the following composition -- see Original Patent.

where the content can fluctuate within these limits depending on the origin of the monomers, the polymerization process and the work-up process.

The dimeric fatty acid used may also be present in hydrogenated form.

The content of dimeric acid can be increased to 100% by weight by generally known distillation processes. It is determined by the known processes of gas-liquid chromatography (GLC). The acid numbers are in the range from about 190 to 200.

By co-using these acids, a significantly improved stabilization of the phase interfaces in W/O emulsions can be achieved.

Suitable additional fatty acid components are primarily saturated fatty acids, such as, for example, lauric acid, tridecanoic acid, myristic acid, palmitic acid, margaric acid, stearic acid, isostearic acid, arachidic acid and behenic acid, and mixtures thereof.

Naturally occurring mixtures are, for example, the coconut fatty acids which comprise, as a main constituent, lauric acid, and also saturated C.sub.14-C.sub.18-fatty acids and optionally saturated C.sub.8-C.sub.10-fatty acids and unsaturated fatty acids, and also tallow fatty acids, which essentially constitute a mixture of palmitic acid and stearic acid.

Suitable additional unsaturated fatty acid components are monoolefinically unsaturated acids, for example, hexadecenoic acids, octadecenoic acids, such as, oleic acid (cis-9-octadecenoic acid) or elaidic acid (trans-9-octadecenoic acid), eicosenoic acids and docosenoic acids, such as, erucic acid (cis-13-docosenoic acid) or brassidic acid (trans-13-docosenoic acid), polyunsaturated fatty acids, for example, octodecadienoic acids and octodecatrienoic acids, such as, linoleic acid and linolenic acid, and mixtures thereof.

Of particular suitability are the liquid fatty acids, such as, oleic acid, ricinoleic acid, erucic acid and isostearic acid which contain 18 to 22 carbon atoms. On account of branching or a double bond in the hydrocarbon chain, their solidification points are below 35.degree. C. It is also possible to use fatty acid mixtures, which may also comprise wax-like components, such as, hydrogenated ricinoleic acid.

Furthermore, the use of lactones, such as, butyrolactone or caprolactone, as fatty acid component is possible.

In the polyglycerol partial esters according to the instant invention, the hydroxyl groups of the polyglycerol are esterified to 20 to 75%, preferably 40 to 70%.

For their preparation, preference is given to the variants A) and B) according to which in A) the first stage polyglycerol is esterified to a degree of esterification of from 10 to 70%, preferably 25 to 40%, with fatty acid and dicarboxylic acid and/or tricarboxylic acid, and then in a second stage is esterified with polyricinoleic acid to a total degree of esterification of from 20 to 75%, preferably 40 to 60%, or in B) the first stage polyglycerol is esterified to a degree of esterification of from 10 to 70%, preferably 25 to 40%, with fatty acid and polyricinoleic acid and in a second stage is esterified with dicarboxylic acid and/or tricarboxylic acid to a total degree of esterification of from 20 to 75%, preferably 40 to 60%.

Adding the components in another order, such as, for example, adding firstly the fatty acid, then the dicarboxylic acid and/or tricarboxylic acid and subsequently the polyricinoleic acid, and one-pot processes are likewise possible.

Through appropriate choice of the hydrophilic and lipophilic molecular moieties it is possible, for example, to establish an HLB value of from about 3 to 8 in order to obtain properties which are favorable for the stabilization of W/O emulsions.

The polyglycerol partial esters according to the present invention can be prepared in a manner known per se by heating the reaction components to 100.degree. to 300.degree. C., preferably 180.degree. to 260.degree. C., and removing the water of reaction which forms by distillation. To increase the rate, acidic or basic catalysts, such as, sulfonic acids, phosphoric acid or phosphorous acid, Lewis acids, such as, zinc salts, alkali metal or alkaline earth metal oxides or hydroxides, alkoxides or salts, can be co-used. The addition of a catalyst, however, is not absolutely necessary. The progressing conversion can be monitored, for example, by means of the water of reaction which has been separated off, by measuring the acid number or by infrared spectroscopy. In general, an acid number in the end product of <20, preferably <10, is the aim. Particular preference is given to products with an acid number of <5.

The polyglycerol esters according to the present invention are particularly suitable for producing emulsions and dispersions in which the oil phase is the external phase.

Under certain prerequisites, e.g., by adding suitable hydrophilic co-emulsifiers, the polyglycerol esters according to the present invention can also be used for producing emulsions and dispersions in which the aqueous phase forms the external phase.

Preference is given to their use as emulsifiers and dispersion auxiliaries for producing cosmetic or pharmaceutical preparations. These are cosmetic preparations which, through the use of oil-in-water or water-in-oil emulsifiers, are given a readily spreadable consistency because these emulsifier systems allow an oil or a fat to be readily incorporated into an aqueous phase, or an aqueous phase to be readily incorporated into an oil or a fat, for example, creams, such as, care creams, baby creams or sun protection creams, ointments, lotions or make-up. In pharmaceutical preparations, such as, ointments or creams, oil-in-water or water-in-oil emulsifiers are required for the formulation of active ingredients.

The cosmetic oils which are co-used include, in particular, mono- or diesters of linear and/or branched mono- and/or dicarboxylic acids having 2 to 44 carbon atoms with linear and/or branched saturated or unsaturated alcohols having 1 to 22 carbon atoms. Likewise of suitability within the meaning according to the present invention are the esterification products of aliphatic, difunctional alcohols having 2 to 36 carbon atoms with monofunctional aliphatic carboxylic acids having 1 to 22 carbon atoms. Monoesters suitable as oil components are, for example, the methyl esters and isopropyl esters of fatty acids having 12 to 22 carbon atoms, for example, methyl laurate, methyl stearate, methyl oleate, methyl erucate, isopropyl palmitate, isopropyl myristate, isopropyl stearate, or isopropyl oleate. Other suitable monoesters are, for example, n-butyl stearate, n-hexyl laurate, n-decyl oleate, isooctyl stearate, isononyl palmitate, isononyl isononanoate, 2-ethylhexyl palmitate, 2-ethylhexyl laurate, 2-hexyldecyl stearate, 2-octyldodecyl palmitate, oleyl oleate, oleyl erucate, or erucyl oleate, and esters which are obtainable from technical-grade aliphatic alcohol cuts and technical-grade, aliphatic carboxylic acid mixtures, e.g., esters of unsaturated fatty alcohols having 12 to 22 carbon atoms and saturated and unsaturated fatty acids having 12 to 22 carbon atoms, as are obtainable from animal and vegetable fats. Also of suitability, however, are naturally occurring monoester and/or wax ester mixtures, as are present, for example, in jojoba oil or in sperm oil.

Examples of dicarboxylic acid esters which are co-used include di-n-butyl adipate, di-n-butyl sebacate, di(2-ethylhexyl) adipate, or di(2-hexyldecyl) succinate, diisotridecyl acelate. Suitable diol esters are, for example, ethylene glycol dioleate, ethylene glycol diisotridecanoate, propylene glycol di(2-ethylhexanoate), butanediol diisostearate and neopentyl glycol dicaprylate.

Further fatty acid esters which can be used are, for example, C.sub.12-15-alkyl benzoate, dicaprylyl carbonate, or diethylhexyl carbonate.

As oil component it is likewise possible to use fatty acid triglycerides, preference being given among these to the naturally occurring oils and fats. Thus, for example, natural vegetable oils, e.g., olive oil, sunflower oil, soya oil, peanut oil, rapeseed oil, almond oil, palm oil, but also the liquid fractions of coconut oil or of palm kernel oil, and animal oils, such as, for example, neatsfoot oil, the liquid fractions of beef tallow or also synthetic triglycerides of caprylic/capric acid mixtures, triglycerides of technical-grade oleic acid or of palmitic acid/oleic acid mixtures are suitable as oil components.

In addition, hydrocarbons, in particular liquid paraffins and isoparaffins, can be used. Examples of hydrocarbons which can be used are paraffin oil, isohexadecane, polydecene, vaseline, paraffinum perliquidum, or squalane.

In addition, it is also possible to use linear or branched fatty alcohols, such as, oleyl alcohol or octyldodecanol, and fatty alcohol ethers, such as, dicaprylyl ether.

Suitable silicone oils and silicone waxes are, for example, polydimethylsiloxanes, cyclomethylsiloxanes, and also aryl- or alkyl- or alkoxy-substituted polymethylsiloxanes or cyclomethylsiloxanes.

In addition, auxiliaries and additives customary in cosmetic and pharmaceutical applications and known to the person skilled in the art can be used. These include, for example, co-emulsifiers, consistency regulators, thickeners, waxes, UV photoprotective filters, antioxidants, hydrotropes, deodorant and antiperspirant active ingredients, insect repellents, self-tanning agents, preservatives, perfume oils, dyes and biogenic active ingredients.

Besides the polyglycerol esters according to the present invention, additional emulsifiers or surfactants can also be used. These are preferably nonionic, anionic, cationic or amphoteric surfactants.

In particular, the polyglycerol esters according to the present invention can be used in W/O emulsions, which can additionally also comprise dispersed solids, for keeping the overall viscosity of the preparation as low as possible.

Non-ionogenic emulsifiers or surfactants which may be co-used are compounds from at least one of the following groups:

addition products of from 2 to 30 mol of ethylene oxide and/or 0 to 5 mol of propylene oxide onto linear fatty alcohols having 8 to 22 carbon atoms, onto fatty acids having 12 to 22 carbon atoms and onto alkylphenols having 8 to 15 carbon atoms in the alkyl group

C.sub.12/18-fatty acid mono- and diesters of addition products of from 1 to 30 mol of ethylene oxide onto glycerol

glycerol mono- and diesters and sorbitan mono- and diesters of saturated and unsaturated fatty acids having 6 to 22 carbon atoms and ethylene oxide addition products thereof

alkyl mono- and oligoglycosides having 8 to 22 carbon atoms in the alkyl radical and ethylene oxide addition products thereof

addition products of from 2 to 200 mol of ethylene oxide onto castor oil and/or hydrogenated castor oil

partial esters based on linear, branched, unsaturated or saturated C.sub.6-22-fatty acids, ricinoleic acid, and 12-hydroxystearic acid and glycerol, polyglycerol, pentaerythritol, dipentaerythritol, sugar alcohols (e.g., sorbitol), alkyl glucosides (e.g., methyl glucoside, butyl glucoside, lauryl glucoside), and polyglucosides (e.g., cellulose).

Here, the use of partial esters of glycerol and of polyglycerol is preferred. These are, for example, glycerol oleate, glycerol isostearate, polyglycerol isostearates, polyglycerol oleates, polyglycerol polyricinoleates, polyglycerol poly-12-hydroxystearates or distearoyl polyglyceryl-3 dimer dilinoleate (ISOLAN.RTM. PDI, Degussa). Particularly in combination with distearoyl polyglyceryl-3 dimer dilinoleate (ISOLAN.RTM. PDI, Degussa), the polyglycerol partial esters according to the present invention can be used, depending on the mixing ratio of these two types of emulsifier, such that it is possible to obtain either low-viscosity water-in-oil lotions, or rich water-in-oil creams.

mono-, di- and trialkyl phosphates, and mono-, di- and/or tri-PEG alkyl phosphates and salts thereof

polysiloxane-polyether copolymers (dimethicone copolyols), such as, for example, PEG/PPG-20/6 dimethicone, PEG/PPG-20/20 dimethicone, bis-PEG/PPG-20/20 dimethicone, PEG-12 or PEG-14 dimethicone, PEG/PPG-14/4 or 14/12 or 20/20 or 18/18 or 17/18 or 15/15. Of particular suitability here are products such as bis-PEG/PPG-14/14 dimethicone (with cyclopentasiloxane: ABIL.RTM. EM 97 (Degussa)) or PEG/PPG-16/16 PEG/PPG-16/16 dimethicone (with caprylic/capric triglycerides: ABIL.RTM. Care 85 (Degussa))

polysiloxane-polyalkyl-polyether copolymers and corresponding derivatives, such as, for example, lauryl or cetyl dimethicone copolyols, in particular cetyl PEG/PPG-10/1 dimethicone (ABIL.RTM. EM 90 (Degussa))

mixed esters of pentaerythritol, fatty acids, citric acid and fatty alcohol according to DE-11 65 574 and/or mixed esters of fatty acids having 6 to 22 carbon atoms, methylglucose and polyols, preferably glycerol or polyglycerol.

It is also possible to additionally use anionic emulsifiers or surfactants.

These contain solubilizing anionic groups, such as, for example, a carboxylate, sulfate, sulfonate, or phosphate group and a lipophilic radical. Skin-compatible anionic surfactants are known to the person skilled in the art in large numbers and are commercially available. These are, in particular, alkyl sulfates or alkyl phosphates in the form of their alkali metal, ammonium or alkali ammonium salts, alkyl ether sulfates, alkyl ether carboxylates, acyl sarcosinates, and sulfosuccinates and acyl glutamates in the form of their alkali metal or ammonium salts.

Cationic emulsifiers can also be added as surfactants.

As such, it is possible to use, in particular, quaternary ammonium compounds, such as, alkyltrimethylammonium halides, such as, for example, cetyltrimethylammonium chloride or bromide or behenyltrimethylammonium chloride, but also dialkyldimethylammonium halides, such as, for example, disteraryldimethylammonium chloride. In addition, monoalkylamidoquats, such as, for example, palmitamidopropyltrimethylammonium chloride or corresponding dialkylamidoquats can be used. Furthermore, it is also possible to use readily biodegradable quaternary ester compounds, which are mostly quaternized fatty acid esters based on mono-, di- or triethanolamine. In addition, alkylguanidinium salts can be added as cationic emulsifiers.

In addition, it is possible to use amphoteric surfactants, such as, for example, betaines, amphoacetates or amphopropionates together with the polyglycerol esters according to the present invention.

In addition, the low-viscosity emulsions according to the present invention can comprise customary auxiliaries and additives, such as, thickeners, UV photoprotective filters, antioxidants, hydrotropes, deodorant and antiperspirant active ingredients, insect repellents, self-tanning agents, perfume oils, dyes and biogenic active ingredients.

Of suitability for thickening oil phases are all thickeners known to the person skilled in the art. Mention is made here in particular of waxes, such as, hydrogenated castor wax, beeswax or microwax. In addition, inorganic thickeners can also be used, such as, silica, alumina or sheet silicates (e.g., hectorite, laponite, saponite). These inorganic oil phase thickeners are here preferably hydrophobically modified.

For thickening/stabilizing water-in-oil emulsions prepared by a cold process, it is possible to use, in particular, aerosils and/or metal salts of fatty acids, such as, for example, zinc stearate.

UV photoprotective filters are understood as meaning organic substances which are able to absorb ultraviolet rays and release the absorbed energy again in the form of longer-wave radiation, e.g., heat. UV-B filters may be oil-soluble or water-soluble. Examples of oil-soluble substances are:

3-benzylidenecamphor and derivatives thereof, e.g., 3-(4-methylbenzylidene)camphor

4-aminobenzoic acid derivatives, preferably 2-ethylhexyl 4-(dimethylamino)benzoate, 2-ethylhexyl 4-(dimethylamino)benzoate and amyl 4-(dimethylamino)benzoate

esters of cinnamic acid, preferably 2-ethylhexyl 4-methoxycinnamate, isopentyl 4-methoxycinnamate, 2-ethylhexyl 2-cyano-3-phenylcinnamate (octocrylene)

esters of salicylic acid, preferably 2-ethylhexyl salicylate, 4-isopropylbenzyl salicylate, homomenthyl salicylate

derivatives of benzophenone, preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone

esters of benzalmalonic acid, preferably di-2-ethylhexyl 4-methoxybenzalmalonate

triazine derivatives, such as, for example, 2,4,6-trianilino(p-carbo-2'-ethyl-1'-hexyloxy)-1,3,5-triazine and octyltriazone

propane-1,3-diones, such as, for example, 1-(4-tert-butylphenyl)-3-(4'-methoxyphenyl)propane-1,3-dione.

Water-soluble substances which can be co-used are:

2-phenylbenzimidazole-5-sulfonic acid and the alkali metal, alkaline earth metal, ammonium, alkylammonium, alkanolammonium and glucammonium salts thereof

sulfonic acid derivatives of benzophenone, preferably 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and its salts

sulfonic acid derivatives of 3-benzylidenecamphor, such as, for example, 4-(2-oxo-3-bornylidenemethyl)benzenesulfonic acid and 2-methyl-5-(2-oxo-3-bornylidene)sulfonic acid and salts thereof.

Suitable typical UV-A filters are, in particular, derivatives of benzoylmethane, such as, for example, 1-(4'-tert-butylphenyl)-3-(4'-methoxyphenyl)propane-1,3-dione or 1-phenyl-3-(4'-isopropylphenyl)propane-1,3-dione. The UV-A and UV-B filters can of course also be used in mixtures. Besides the specified soluble substances, insoluble pigments are also suitable for this purpose, namely finely disperse metal oxides or salts, such as, for example, titanium dioxide, zinc oxide, iron oxide, aluminum oxide, cerium oxide, zirconium oxide, silicates (talc), barium sulfate and zinc stearate. The particles here should have an average diameter of less than 100 nm, preferably between 5 and 50 nm and in particular between 15 and 30 nm. They can have a spherical shape, although it is also possible to use particles which have an ellipsoidal shape or a shape which deviates in some other way from the spherical configuration. A relatively new class of photoprotective filters are micronized organic pigments, such as, for example, 2,2'-methylenebis{6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)ph- enol} with a particle size of less than 200 nm, which is obtainable, for example, as 50% strength aqueous dispersion.

Besides the two abovementioned groups of primary photoprotective substances, it is also possible to use secondary photoprotective agents of the antioxidant type; these interrupt the photochemical reaction chain which is triggered when UV radiation penetrates into the skin. Typical examples thereof are superoxide dismutase, tocopherols (vitamin E) and ascorbic acid (vitamin C). Further suitable UV photoprotective filters can be found in the overview by P. Finkel in SOFW-Journal 122, 543 (1996).

To improve the flow behavior and the application properties, it is also possible to use hydrotropes, such as, for example, ethanol, isopropyl alcohol, or polyols. Polyols which are suitable here preferably have 2 to 15 carbon atoms and at least two hydroxyl groups. Typical examples are

glycerol

alkylene glycols, such as, for example, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol, and polyethylene glycols with an average molecular weight of from 100 to 1000 Daltons

technical-grade oligoglycerol mixtures with a degree of self-condensation of from 1.5 to 10, such as, for example, technical-grade diglycerol mixtures with a diglycerol content of from 40 to 50% by weight

methylol compounds, such as, in particular, trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol

lower alkyl glucosides, in particular those having 1 to 4 carbon atoms in the alkyl radical, such as, for example, methyl glucoside and butyl glucoside

sugar alcohols having 5 to 12 carbon atoms, such as, for example, sorbitol or mannitol

sugars having 5 to 12 carbon atoms, such as, for example, glucose or sucrose

amino sugars, such as, for example, glucamine.

Suitable deodorant active ingredients are, for example, odor concealers, such as, the customary perfume constituents, odor absorbers, for example, the sheet silicates described in the patent laid-open specification DE-40 09 347, of these, in particular, montmorillonite, kaolinite, illite, beidelite, nontronite, saponite, hectorite, bentonite, or smectite, also, for example, zinc salts of ricinoleic acid. Antibacterial agents are likewise suitable for incorporation into the oil-in-water emulsions according to the invention. Advantageous substances are, for example, 2,4,4'-trichloro-2'-hydroxydiphenyl ether (irgasan), 1,6-di(4-chlorophenylbiguanido)hexane (chlorhexidine), 3,4,4'-trichlorocarbanilide, quaternary ammonium compounds, oil of cloves, mint oil, thyme oil, triethyl citrate, farnesol (3,7,11-trimethyl-2,6,10-dodecatrien-1-ol), ethylhexyl glyceryl ether, polyglyceryl-3 caprylate (TEGO.RTM. Cosmo P813, Degussa), and the active agents described in the patent laid-open specifications DE-198 55 934, DE-37 40 186, DE-39 38 140, DE-42 04 321, DE-42 29 707, DE-42 29 737, DE-42 38 081, DE-43 09 372, DE-43 24 219 and EP-666 732. Further customary antiperspirant active ingredients can likewise be used advantageously in the preparations according to the present invention, in particular astringents, for example, basic aluminum chlorides, such as aluminum chlorohydrate ("ACH") and aluminum zirconium glycine salts ("ZAG").

Suitable insect repellents are N,N-diethyl-m-toluamide, 1,2-pentanediol or Insect Repellent 3535.

Suitable self-tanning agents are, for example, dihydroxyacetone and erythrulose.

Suitable preservatives which may be used are, for example, mixtures of one or more alkyl paraben esters with phenoxyethanol. The alkyl paraben esters are preferably methyl paraben, ethyl paraben, propyl paraben and/or butyl paraben. Instead of phenoxyethanol it is also possible to use other alcohols, such as, for example, benzyl alcohol or ethanol. Moreover, it is also possible to use other customary preservatives, such as, for example, sorbic acid or benzoic acid, salicylic acid, 2-bromo-2-nitropropane-1,3-diol, chloroacetamide, diazolidinylurea, DMDM hydantoin, iodopropynyl butylcarbamate, sodium hydroxymethyl-glycinate or the combination chloromethyl-/methylisothiazoline.

Perfume oils which may be mentioned are mixtures of natural and synthetic fragrances. Natural fragrances are extracts from flowers (lily, lavender, rose, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (anis, coriander, caraway, juniper), fruit peels (bergamot, lemons, oranges), roots (mace, angelica, celery, cardamom, costus, iris, thyme), needles and branches (spruce, fir, pine, dwarf-pine), resins and balsams (galbanum, elemi, benzoin, myrrh, olibanum, opoponax). Animal raw materials are also suitable, such as, for example, civet and castoreum. Typical synthetic fragrance compounds are products of the ester, ether, aldehyde, ketone, alcohol and hydrocarbon type. Fragrance compounds of the ester type are, for example, benzyl acetate, phenoxyethyl isobutyrate, p-tert-butyl cyclohexylacetate, linalyl acetate, dimethylbenzylcarbinyl acetate, phenylethyl acetate, linalyl benzoate, benzyl formate, ethylmethyl phenylglycinate, allyl cyclohexylpropionate, styrallyl propionate and benzyl salicylate. The ethers include, for example, benzyl ethyl ether, the aldehydes include for example, the linear alkanals having 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamenaldehyde, hydroxycitronellal, lilial and bourgeonal, the ketones include, for example, the ionones, .alpha.-isomethylionone and methyl cedryl ketone, the alcohols include anethol, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol, and the hydrocarbons include primarily the terpenes and balsams. However, preference is given to using mixtures of different fragrances which together produce a pleasing scent note. Essential oils of low volatility, which are mostly used as aroma components, are also suitable as perfume oils, e.g., sage oil, chamomile oil, oil of cloves, melissa oil, mint oil, cinnamon leaf oil, linden blossom oil, juniper berry oil, vetiver oil, olibanum oil, galbanum oil, labdanum oil and lavandin oil. Preference is given to using bergamot oil, dihydromyrcenol, lilial, lyral, citronellol, phenylethyl alcohol, .alpha.-hexylcinnamaldehyde, geraniol, benzyl acetone, cyclamenaldehyde, linalool, boisambrene forte, ambroxan, indole, hedione, sandelice, lemon oil, mandarin oil, orange oil, allyl amyl glycolate, cyclovertal, lavandin oil, clary sage oil, .beta.-damascone, geranium oil bourbon, cyclohexyl salicylate, vertofix coeur, iso-E-super, fixolide NP, evernyl, iraldein gamma, phenylacetic acid, geranyl acetate, benzyl acetate, rose oxide, romillat, irotyl and floramat alone or in mixtures.

Dyes which can be used are the substances which are approved and suitable for cosmetic purposes, as are listed, for example, in the publication "Kosmetische Farbemittel" [Cosmetic colorants] from the Dyes Commission of the German Research Society, Verlag Chemie, Weinheim, 1984, p. 81 to 106. These dyes are usually used in concentrations of from 0.001 to 0.1% by weight, based on the total mixture.

Biogenic active ingredients are understood as meaning, for example, tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, deoxyribonucleic acid, coenzyme A10, retinol, bisabolol, allantoin, phytantriol, panthenol, AH acids, amino acids, hyaluronic acid, creatine (and creatine derivatives), guanidine (and guanidine derivatives), ceramides, phytosphingosine (and phytosphingosine derivatives), sphingosine (and sphingosine derivatives), pseudoceramides, essential oils, peptides, protein hydrolysates, plant extracts and vitamin complexes.
 

Claim 1 of 9 Claims

1. A polyglycerol partial ester of polyricinoleic acid and sebacic acid, prepared by esterification of a polyglycerol mixture with components comprising: (i) at least one polyricinoleic acid of the general formula 1 -- see Original Patent.
 

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