# Patent

## Title
Cross-linked polyglycerol esters

## Abstract

The invention provides polyglycerol partial esters based on mono- and dicarboxylic acids and their use as solubilizers, particularly in cosmetics, for example for perfume oils and essential oils in aqueous systems.

## Background
This application claims the benefit of European Application No. 15194652.2 filed on Nov. 16, 2015, the disclosure of which is expressly incorporated herein by reference.
FIELD OF THE INVENTION
The invention provides polyglycerol partial esters based on mono- and dicarboxylic acids and their use as solubilizers, particularly in cosmetics, for example for perfume oils and essential oils in aqueous systems.
PRIOR ART
WO2012007754 discloses polyglycerol partial esters obtained by reacting polyglycerol having 3 to 20 glycerol units with a dicarboxylic acid or a cyclic anhydride of such a dicarboxylic acid having 4 to 22 carbon atoms and a monocarboxylic acid having 4 to 24 carbon atoms in a molar ratio of from 1.5:1.0:0.1 to 3.0:1.0:3.0, and also the use of these polyglycerol partial esters as emulsifier, solubilizer and/or thickener in body care and/or have care formulations.
EP0835862 describes polyglycerol partial esters of saturated or unsaturated, linear or branched fatty acids and polyfunctional carboxylic acids, obtainable by esterification of a polyglycerol mixture with saturated or unsaturated, linear or branched fatty acids having 12 to 22 carbon atoms and polyfunctional carboxylic acids having 4 to 54 carbon atoms and an average functionality of 2 to 2.4, wherein the degree of esterification of the polyglycerol mixture is from 30 to 75%.
EP1683781 describes polyglycerol partial esters of polyricinoleic acid and polyfunctional carboxylic acids, obtainable by esterification a) of a polyglycerol mixture with b) at least one particular polyricinoleic acid and optionally b1) polyhydroxystearic acid and c) at least one di- and/or tricarboxylic acid and d) at least one fatty acid according to methods known per se. The polyglycerol preferably has an average degree of condensation n of 1 to 11, preferably 2 to 6.
EP1500427 describes polyglycerol partial esters of polyhydroxystearic acid and polyfunctional carboxylic acids, obtainable by esterification of a polyglycerol mixture with polyhydroxystearic acid and di- and/or tricarboxylic acids and optionally/or with dimeric fatty acids and fatty acids having 6 to 22 carbon atoms.
A disadvantage of the polyglycerol partial esters described in the prior art is that these are not able to clearly solubilize relatively polar oils, with relatively low excesses of polyglycerol partial esters, in water or aqueous formulations. Relatively polar oils are, for example, essential oils and perfume oils, for example, rosemary or lemon oil. Polyglycerol esters having high proportions of dicarboxylic acids have a tendency that formulations for solubilizing oils are not clear and are opalescent.
A further disadvantage of the compounds described in the prior art is that these are not able to clearly solubilize perfume oils, with relatively low excesses of polyglycerol partial esters, in aluminium chlorohydrate-containing or other strongly electrolyte-containing formulations.
A further disadvantage of the compounds described in the prior art is that these are often relatively difficult to formulate, especially due to high viscosities of the products, or that difficult or lengthy formulation work is required during the preparation of the formulation.
SUMMARY
The object of the invention was to provide polyglycerol partial esters with which essential oils and perfume oils, using low amounts of polyglycerol partial esters, can be solubilized clearly and readily in water, in aqueous formulations, in aluminium chlorohydrate-containing or other strongly electrolyte-containing formulations.


DESCRIPTION OF THE INVENTION
Surprisingly, it has been found that the polyglycerol partial esters described below are able to solve the problem addressed by the invention.
The present invention therefore provides a polyglycerol partial ester obtainable by esterification of a polyglycerol with a carboxylic acid mixture comprising:

    a) at least one short-chain dicarboxylic acid having 2 to 12, preferably 3 to 8, particularly preferably 4 carbon atoms, and
    b) at least one saturated fatty acid having 6 to 14, preferably 8 to 10 carbon atoms, characterized in that the molar ratio of polyglycerol to dicarboxylic acid to saturated fatty acid is from 3.1:1.0:0.5 to 14:1.0:6.0, preferably from 3.3:1.0:0.7 to 7.0:1.0:3.0.


The invention further provides the use of corresponding polyglycerol partial esters as solubilizer.
An advantage of the present invention is that the polyglycerol partial esters described here are able to clearly solubilize hydrophobic, oil-soluble substances, such as essential oils, in water or in a cosmetic formulation.
A further advantage is that the polyglycerol partial esters described here may be prepared exclusively from renewable raw materials in contrast to polyethoxylated triglycerides (e.g. PEG-40 Hydrogenated Castor Oil).
Another advantage of the present invention is that formulations may be provided that are polyglycol ether-free.
A further advantage is that the polyglycerol partial esters described here are liquid, and thus readily processable, in contrast to polyethoxylated triglycerides. Also in comparison to polyglycerol esters of the prior art, the products according to the invention are comparatively easy to process. Owing to the comparatively low product viscosities, the fluidity can be further improved by low amounts of added solvents such as water or 1,2- and 1,3-propanediol or glycerol, in order to ensure even better processability.
A further advantage compared to the polyethoxylated triglycerides and even partly to the polyglycerol esters of the prior art is that the polyglycerol esters described here lead to obviously particularly clear dispersions of the oil in water, and also no cloudiness occurs on storage.
A further advantage of the polyglycerol partial esters described here is that these can produce a pleasant skin sensation in cosmetic formulations.
Another advantage of the polyglycerol partial esters described here is that these exhibit only a very low foam formation on stirring in water.
A further advantage is that the polyglycerol partial esters described here show only a very low effect on foamability and foam quantity in surfactant formulations, but the foam creaminess can, however, improve.
Another advantage is that the polyglycerol partial esters described here may lead to attenuation of skin irritancy in surfactant formulations.
Another advantage is that the polyglycerol partial esters described here may function as moisturizer (humectant) in cosmetic formulations.
A further advantage of the polyglycerol partial esters described here is that these can have a stabilizing effect in emulsions.
Another advantage of the products according to the invention is that these show particularly good results in make-up removers.
A further advantage of the products according to the invention is that these have a relatively low effect on the viscosity of surfactant formulations.
A further advantage of the products according to the invention is that these are relatively stable to oxidation and are stable with respect to color, odor and appearance.
Another advantage of the products according to the invention is that these are particularly compatible with electrolytes (such as sodium chloride, aluminium salts or cationic surfactants) in formulations.
The polyglycerol partial esters according to the invention are mixtures of different substances; it is therefore clear to those skilled in the art that the numeric values specified are average values for the mixture.
In the context of the present invention, the term “polyglycerol” is to be understood as meaning a polyglycerol which may also comprise glycerol. Consequently, for the purposes of calculating amounts, masses and the like, optionally a glycerol fraction should also be taken into consideration. Owing to its polymeric property, the polyglycerol is a statistical mixture of various compounds. Polyglycerol may have formed ether bonds between two primary, one primary and one secondary and also two secondary positions of the glycerol monomers. For this reason, the polyglycerol base skeleton does not usually consist exclusively of linearly linked glycerol units, but may also comprise branches and rings. For details see, e.g. “Original synthesis of linear, branched and cyclic oligoglycerol standards”, Cassel et al., J. Org. Chem., 2001, 875-896.
The same applies to the term “polyglycerol partial ester” in connection with the present invention.
Unless otherwise stated, all percentages (%) given are percentages by weight.
Preferred polyglycerol partial esters according to the invention are characterized in that the polyglycerol used has an average degree of condensation N of 1.5 to 9, preferably 2 to 7, particularly preferably 2.5 to 5.
The average degree of polymerization of the polyglycerol N is calculated via its hydroxyl number (OHN, in mg KOH/g) according to the following formula:




  N
  =
  
    
      (
      
        112200
        -
        
          18
          ·
          OHN
        
      
      )
    
    
      (
      
        
          74
          ·
          OHN
        
        -
        56100
      
      )
    
  




Suitable methods for determining the hydroxyl number are particularly those according to DGF C-V 17 a (53), Ph. Eur. 2.5.3 Method A and DIN 53240.
A preferred polyglycerol partial ester according to the invention is therefore characterized in that the polyglycerol used has a hydroxyl number of 1500 to 900, preferably 1350 to 940, particularly preferably 1245 to 1010 mg KOH/g.
The polyglycerol used can be provided by different conventional methods such as, for example, polymerization of glycidol (e.g. base-catalysed), polymerization of epichlorohydrin (for example in the presence of equimolar amounts of a base such as NaOH) or polycondensation of glycerol.
The polyglycerol partial ester according to the invention is obtainable by esterification of a polyglycerol with a carboxylic acid mixture comprising components a) and b). It is preferred in accordance with the invention if components a) and b) make up in total at least 80% by weight, preferably at least 90% by weight, particularly preferably at least 95% by weight, based on the total carboxylic acid mixture used.
It is preferred in accordance with the invention if the dicarboxylic acid in the polyglycerol partial ester according to the invention is selected from aliphatic, linear dicarboxylic acids, in particular oxalic acid, malonic acid, tartronic acid, succinic acid, maleic acid, tartaric acid, malic acid, fumaric acid, sorbic acid, α-ketoglutaric acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, dodecanedioic acid, wherein succinic acid is particularly preferred.
A preferred polyglycerol partial ester according to the invention is characterized in that the saturated fatty acid is selected from unbranched, unsubstituted fatty acids.
A preferred polyglycerol partial ester according to the invention is characterized in that it has a saponification number of 70 to 199 mg KOH/g, preferably 95 to 190, particularly preferably 120 to 180 mg KOH/g. The determination of the saponification number is carried out by those skilled in the art according to DGF C-V 3 or DIN EN ISO 3681.
A preferred polyglycerol partial ester according to the invention is characterized in that in the esterification the molar ratio of a) to b) is
from 1.0:0.7 to 1.0:3.0, preferably
from 1.0:0.8 to 1.0:2.0, more preferably
from 1.0:1.0 to 1.0:1.6.
A preferred polyglycerol partial ester according to the invention is characterized in that at 1 bar it has a turbidity point of 45 to 75° C., preferably 50 to 65° C.
The turbidity point is determined according to DIN EN 1890. For this purpose, 0.9 g of polyglycerol partial ester is weighed out into a 250 ml glass beaker and 100 g of 10% NaCl solution are added. This composition is heated until a distinct cloudiness occurs. While stirring with a thermometer, the composition is allowed to cool until this is clear again; the temperature of the clarification is defined as the “turbidity point”. This clear composition has a turbidity value of NTU<3. The cloudiness is measured with a HI88713 laboratory turbidity measuring instrument (ISO 7027, light detector: silicon photocell; light source: infrared LED) by the transmitted light method in the normal mode with respect to formazine and is stated in NTU.
A preferred polyglycerol partial ester according to the invention is characterized in that it has a viscosity of 20 to 200 Pa s, preferably 50 to 150 Pa s, at 25° C.
The viscosity is determined using a rheometer from Anton Paar, model MCR 301, parallel plate (40 mm) geometry at a temperature of 25° C. in the shear rate range of 0.1 s−1 to 1000 s−1. The value specified here of the viscosity is measured at a shear rate of 10 s−1.
It is preferred in accordance with the invention if the polyglycerol partial ester according to the invention has an HLB value, according to Griffin, W. C.: Classification of surface active agents by HLB, J. Soc. Cosmet. Chem. 1, 1949, of 13 to 17.
The polyglycerol partial ester according to the invention preferably has a surface tension of less than 28 mN/m in 1.0% aqueous solution at 20° C.
The surface tension is measured in this case using a pendant drop tensiometer OCA 35 from Dataphysics Instruments (www.dataphysics.de). The value specified is the equilibrium value.
The polyglycerol partial esters of the present invention can be prepared by classical esterification methods; in place of carboxylic acids the corresponding carboxylic acid derivatives, their anhydrides or carboxylic esters for example (such as methyl or ethyl esters), may also of course be used.
The present invention further provides a composition comprising
the polyglycerol partial ester according to the invention and
10 to 50% by weight, preferably 20 to 40% by weight 1,2- or 1,3-propanediol
or
5% to 50% by weight, preferably 8% to 30% by weight water,
wherein the percentages by weight refer to the total composition and wherein the compositions have a viscosity of 0.1 to 10 Pa s, preferably 0.5 to 7.5 Pa s, at 25° C.
The present invention further relates to the use of at least one polyglycerol partial ester according to the invention as solubilizer, particularly of oils, particularly in cosmetic or pharmaceutical preparations.
The polyglycerol partial esters of the present invention are particularly used for solubilizing oils in water, aqueous and/or surfactant formulations. Likewise preferred is the use of at least one polyglycerol partial ester according to the invention as solubilizer of oils in aluminium chlorohydrate-containing cosmetic formulations, especially in deodorant formulations. The use according to the invention is applied particularly to polyether-free preparations. The examples adduced below illustrate the present invention by way of example, without any intention that the invention, the scope of application of which is apparent from the entirety of the description and the claims, be restricted to the embodiments specified in the examples.
EXAMPLES
Example 1: Inventive
Under a nitrogen atmosphere, 400 g of polyglycerol-3 (hydroxyl number=1155 mg KOH/g) were stirred with 80.0 g of caprylic/capric acid (0.30 mol equiv.) and 55.0 g of succinic acid (0.28 mol equiv.) at 240° C. until an acid number <1 mg KOH/g was achieved. The water formed during the course of the reaction was continuously distilled off After cooling to room temperature, the reaction product appeared as a pale yellow, clear to slightly cloudy liquid and had the following analytical data: viscosity: 120 Pa s; viscosity, 75% in 1,2-propanediol: 5.1 Pa s; acid number: 0.2 mg KOH/g; saponification number: 157 mg KOH/g; turbidity point: 56° C.
Example 2: Inventive
Under a nitrogen atmosphere, 400 g of polyglycerol-3 (hydroxyl number=1155 mg KOH/g) were stirred with 85.0 g of caprylic/capric acid (0.32 mol equiv.) and 55.0 g of succinic acid (0.28 mol equiv.) at 240° C. until an acid number <1 mg KOH/g was achieved. The water formed during the course of the reaction was continuously distilled off After cooling to room temperature, the reaction product appeared as a pale yellow, clear to slightly cloudy liquid and had the following analytical data: viscosity: 96 Pa s; acid number: 0.6 mg KOH/g; saponification number: 160 mg KOH/g; turbidity point: 52° C.
Example 3: Inventive
Under a nitrogen atmosphere, 400 g of polyglycerol-3 (hydroxyl number=1155 mg KOH/g) were stirred with 75.0 g of caprylic/capric acid (0.29 mol equiv.) and 40.0 g of succinic acid (0.20 mol equiv.) at 240° C. until an acid number <1 mg KOH/g was achieved. The water formed during the course of the reaction was continuously distilled off After cooling to room temperature, the reaction product appeared as a pale yellow, clear to slightly cloudy liquid and had the following analytical data: viscosity: 90 Pa s; acid number: 0.3 mg KOH/g; saponification number: 131 mg KOH/g; turbidity point: 50° C.
Example 4: Inventive
Under a nitrogen atmosphere, 500 g of polyglycerol-3 (hydroxyl number=1155 mg KOH/g) were stirred with 93.8 g of caprylic/capric acid (0.29 mol equiv.) and 25.0 g of succinic acid (0.10 mol equiv.) at 240° C. until an acid number <1 mg KOH/g was achieved. The water formed during the course of the reaction was continuously distilled off After cooling to room temperature, the reaction product appeared as a pale yellow, clear to slightly cloudy liquid and had the following analytical data: viscosity: 123 Pa s; acid number: 0.9 mg KOH/g; saponification number: 100 mg KOH/g; turbidity point: 69° C.
Example 5: Inventive
Under a nitrogen atmosphere, 300 g of polyglycerol-3 (hydroxyl number=1155 mg KOH/g) were stirred with 37.5 g of caprylic/capric acid (0.19 mol equiv.) at 180° C. for 11 h. After cooling to 50° C., 15.0 g of tartaric acid (0.08 mol equiv.) were added and the mixture was stirred at 180° C. for a further 14 h. The water formed during the course of the reaction was continuously distilled off. After cooling to room temperature, the reaction product appeared as a yellow, clear to slightly cloudy liquid and had the following analytical data: viscosity: 97 Pa s; acid number: 2.0 mg KOH/g; saponification number: 73 mg KOH/g; turbidity point: 51° C.
Example 6: Non-Inventive
Under a nitrogen atmosphere, 400 g of polyglycerol-3 (hydroxyl number=1155 mg KOH/g) were stirred with 85.0 g of caprylic/capric acid (0.32 mol equiv.) and 80.0 g of succinic acid (0.40 mol equiv.) at 240° C. until an acid number <1 mg KOH/g was achieved. The water formed during the course of the reaction was continuously distilled off After cooling to room temperature, the reaction product appeared as a pale yellow, clear to slightly cloudy liquid and had the following analytical data: viscosity: 297 Pa s; viscosity, 75% in 1,2-propanediol: 7.8 Pa s; acid number: 0.4 mg KOH/g; saponification number: 200 mg KOH/g; turbidity point: 56° C.
Example 7: Non-Inventive
Under a nitrogen atmosphere, 400 g of polyglycerol-3 (hydroxyl number=1155 mg KOH/g) were stirred with 85.0 g of caprylic/capric acid (0.32 mol equiv.) and 150 g of succinic acid (0.76 mol equiv.) at 240° C. until an acid number <1 mg KOH/g was achieved. The water formed during the course of the reaction was continuously distilled off. After cooling to room temperature, the reaction product appeared as a pale yellow, highly viscous, very sticky paste, such that most of the data were not determined due to the poor handling qualities: acid number: 0.8 mg; turbidity point: not measurable since product insoluble.
Example 8: TEGOSOFT® PC 41, Non-Inventive
Standard solubilizer, polyether-free. INCI: Polyglyceryl-4 Caprate. Commercial product of Evonik Nutrition & Care GmbH.
Example 9: NATRAGEMTM S 140, Non-Inventive
Solubilizer for oils, polyether-free. INCI: Polyglyceryl-4 Laurate/Sebacate (and) Polyglyceryl-6 Caprylate/Caprate (and) Aqua. Commercial product of Croda.
The products described above were tested in cosmetic formulations below.
The formulation constituents are named in the compositions in the form of the generally recognized INCI nomenclature using the English terms. All concentrations in the application examples are given in percentage by weight.
Example 10: ISOLAN GPS, Non-Inventive
W/O emulsifier, polyether-free. INCI: Polyglyceryl-4 Diisostearate/Polyhydroxystearate/Sebacate. Commercial product of Evonik Nutrition & Care GmbH.
Example 11: Non-Inventive
Under a nitrogen atmosphere, 67.6 g of polyglycerol-4 (hydroxyl number=1080 mg KOH/g) were stirred with 94.8 g of isostearic acid (1.55 mol equiv.) and 17.4 g of sebacic acid (0.40 mol equiv.) at 240° C. until an acid number of <10 mg KOH/g was achieved. 96.0 g of polyricinoleic acid (0.40 mol equiv., acid number=50 mg KOH/g) were then added and the mixture again stirred at 240° C. until an acid number of <5 mg KOH/g was achieved. The water formed during the course of the reaction was continuously distilled off After cooling to room temperature, the reaction product appeared as a yellow, clear to slightly cloudy liquid.
Example 12: Non-Inventive
Under a nitrogen atmosphere, 67.6 g of polyglycerol-4 (hydroxyl number=1080 mg KOH/g) were stirred with 104 g of isostearic acid (1.70 mol equiv.) and 17.4 g of sebacic acid (0.40 mol equiv.) at 240° C. until an acid number of <10 mg KOH/g was achieved. 90.0 g of polyricinoleic acid (0.37 mol equiv., acid number=50 mg KOH/g) and 22.0 g of polyhydroxystearic acid (0.09 mol equiv.) were then added and the mixture again stirred at 240° C. until an acid number of <5 mg KOH/g was achieved. The water formed during the course of the reaction was continuously distilled off. After cooling to room temperature, the reaction product appeared as a yellow, clear to slightly cloudy liquid.
Example 13: Non-Inventive
Under a nitrogen atmosphere, 175.8 g of polyglycerol-14 (hydroxyl number=850 mg KOH/g) were stirred with 88.4 g of isostearic acid (1.86 mol equiv.) and 22.5 g of sebacic acid (0.67 mol equiv.) at 240° C. until an acid number of <10 mg KOH/g was achieved. 157.5 g of polyhydroxystearic acid (0.76 mol equiv., acid number=45 mg KOH/g) were then added and the mixture again stirred at 240° C. until an acid number of <5 mg KOH/g was achieved. The water formed during the course of the reaction was continuously distilled off. After cooling to room temperature, the reaction product appeared as a yellow, clear to slightly cloudy, highly viscous liquid.
Example 14: Non-Inventive
Under a nitrogen atmosphere, 100 g of polyglycerol-4 (hydroxyl number=1080 mg KOH/g) were stirred with 88.4 g of isostearic acid (0.98 mol equiv.) and 157.5 g of polyhydroxystearic acid (0.41 mol equiv., acid number=47 mg KOH/g) at 240° C. until an acid number of <10 mg KOH/g was achieved. The mixture was then cooled to 130° C., 22.5 g of sebacic acid (0.35 mol equiv.) were added and the mixture again stirred at 240° C. until an acid number of <5 mg KOH/g was achieved. The water formed during the course of the reaction was continuously distilled off After cooling to room temperature, the reaction product appeared as a yellow, clear to slightly cloudy liquid.
Example 15: Non-Inventive
Under a nitrogen atmosphere, 61.9 g of polyglycerol-4 (hydroxyl number=1080 mg KOH/g) were stirred with 91.1 g of isostearic acid (1.62 mol equiv.) and 141.7 g of polyhydroxystearic acid (0.58 mol equiv., acid number=45 mg KOH/g) at 240° C. until an acid number of <10 mg KOH/g was achieved. The mixture was then cooled to 130° C., 14.6 g of adipic acid (0.51 mol equiv.) were added and the mixture again stirred at 240° C. until an acid number of <5 mg KOH/g was achieved. The water formed during the course of the reaction was continuously distilled off After cooling to room temperature, the reaction product appeared as a yellow, clear to slightly cloudy liquid.
Example 16: Comparison of Examples 1 to 4 with 6, 8 and 9 and 10 to 15 with Respect to Dissolving Power of Oils in Water
In order to investigate the dissolving power of the inventive polyglycerol partial esters, these were mixed with cosmetic oils and treated with water. The oils tested were rosemary oil, lemon oil and the Spicy Herbs perfume oil (all from supplier Fragrance Resources). The proportion of solubilizer required to dissolve 0.5% of the respective oil completely clearly in water was investigated. Completely clear means that the solution has a turbidity value of NTU<3. To determine the dissolving power, the solubilizer (various amounts) was thoroughly mixed with the oil (0.5 g) and then slowly treated with water (made up to 100 g) with stirring. The mixture was stirred for half an hour at 25° C. A “clear mixture” must not become turbid again over a period of 3 days at 25° C.
In Table 1, the resulting mass ratios of solubilizer to oil which were required to obtain clear mixtures are summarized. It is also noted in the last column how readily the solubilizer could be formulated (+=easy processability, −=poor processability).







TABLE 1







Solubilizer-to-oil ratio required for a clear solution of the oil in water













Rosemary
Spicy
Processing



Lemon oil
oil
Herbs
at 20° C.















Polyglycerol partial ester
 4:1
 3:1
 6:1
+


Example 1


Polyglycerol partial ester
 4:1
 3:1
 6:1
+


Example 2


Polyglycerol partial ester
 6:1
 5:1
 4:1
+


Example 3


Polyglycerol partial ester
 8:1
 4:1
 7:1
+


Example 4


Polyglycerol partial ester
 9:1
 4:1
 7:1
−


Example 6 (non-inventive)


NATRAGEM TM S 140
14:1
7:1
18:1
+


(Example 9, non-inventive)
(opaque/not
(opaque/not
(opaque/not



completely
completely
completely



clear!)
clear!)
clear!)


TEGOSOFT ® PC 41
 16:1
 14:1
 15:1
++


(Example 8, non-inventive)


ISOLAN ® GPS Example 10
>22:1
>22:1
>22:1
+


(non-inventive)


Polyglycerol partial ester
>22:1
>22:1
>22:1
+


Example 11 (non-inventive)


Polyglycerol partial ester
>22:1
>22:1
>22:1
+


Example 12 (non-inventive)


Polyglycerol partial ester
>22:1
>22:1
>22:1
−


Example 13 (non-inventive)


Polyglycerol partial ester
>22:1
>22:1
>22:1
+


Example 14 (non-inventive)


Polyglycerol partial ester
>22:1
>22:1
>22:1
+


Example 15 (non-inventive)









It is evident from the results in Table 1 that the inventive polyglycerol partial esters 1, 2, 3 and 4 almost always have better solubilizing properties than the Comparative Examples 6 and especially 8 and 9. Product 6 (with the high proportion of dicarboxylic acid in the polyglycerol ester), very similar to products 1-4, has a distinctly higher viscosity and, in addition to the somewhat poorer solubilization properties, is especially also significantly less processable than products 1-4. It is preferable to heat the mixture for processing of product 6 since otherwise the mixture with the oil is not uniformly well produced. Heating is not required for the other products. In the likewise very similar product 8 from the prior art it is also noticeable that it is not able to clearly dissolve the oils completely in water. The mixtures with product 8 are always somewhat opaque (even with considerably higher excesses of solubilizer than stated in the table above).
The non-inventive products 10 to 15 were neither able to solubilize the lemon oil or rosemary oil essential oils nor the Spicy Herbs perfume oil. Rather phase separation usually occurred in these experiments. These products are therefore not suitable for this application.
Example 17: Comparison of Example 2 to 8 and 9 with Respect to Dissolving Power of Oils in Aluminium Chlorohydrate-Containing Deodorant Roll-on Formulation
In addition to the solution properties of the polyglycerol partial esters according to the invention for oils in water shown in Example 16, the dissolving power for oils was also investigated in a particularly demanding deodorant formulation (see Table 2) having a high aluminium chlorohydrate (ACH) content.







TABLE 2







Formulation Y for the assessment of the solubilization properties in


a high aluminium chlorohydrate-containing deodorant formulation









Phase
Ingredient
Proportion in %





A
Hydroxyethylcellulose,
1.00%



(Natrosol 250 HR, Ashland)



Water
to 100.00%


B
Aluminium chlorohydrate, 50% in water,
40.00% 



(Locron L, Clariant)



Phenoxyethanol; methylisothiazolinone,
0.45%



(Neolone PE, preservative, Dow)


C
Fragrance oil (Spicy Herb or Pink
1.00%



Grapefruit, both from Fragrance



Resources)



Solubilizer
q.s.









For this purpose, the respective solubilizer was mixed with 1.0 g of the perfume oils Spicy Herb or Pink Grapefruit (both from Fragrance Resources) at room temperature for 5 min. In parallel, 1.0 g of hydroxyethylcellulose was added slowly to water at 45° C. with stirring and clearly dissolved over ca. 90-120 min with stirring (Phase A). Phase B with the aluminium chlorohydrate was then added with stirring to phase A. Finally, the mixture of phases A+B was added slowly with stirring to the mixture of solubilizer and perfume oil.
The proportion of solubilizer required to dissolve 1.0% of the perfume oil completely clearly in the deodorant system was investigated.
In Table 3, the resulting mass ratios of solubilizer-to-oil which were required to obtain clear mixtures are summarized.







TABLE 3







Solubilizer-to-oil ratio necessary for a clear solution of


the respective perfume oil in the deodorant formulation Y











Pink



Spicy Herbs
Grapefruit













Polyglycerol partial ester Example 2
 6:1
 8:1


NATRAGEM TM S 140
>20:1 (phase
>20:1 (phase


(Example 9, non-inventive)
separation
separation



overnight)
overnight)


TEGOSOFT ® PC 41
>20:1
>20:1


(Example 8, non-inventive)









The results in Table 3 show that the polyglycerol partial ester according to the invention of Example 2 has surprisingly very significantly improved solubilizer properties for the oils in this ACH formulation compared to the comparison products NATRAGEMTM S 140 and TEGOSOFT® PC 41. Even at a ratio of 20:1, the comparative examples are not able to clearly dissolve the oils in the formulation.
Example 18: Comparison of Example 1 to 6 and 9 with Respect to Skin Care Performance and Foam Properties
To evaluate the skin care benefit and the foam properties of the inventive polyglycerol partial ester of Example 1 in aqueous surfactant formulations, a sensory handwashing test was conducted in comparison to the Comparative Examples 6 and 9 according to the prior art.
A group consisting of 10 trained test personnel washed their hands in a defined manner and assessed foam properties and skin feel using a grading scale from 1 (poor) to 5 (very good).
The products were formulated in each case in a standardized surfactant formulation, using the standard surfactant system of 9% active Sodium Laureth Sulfate and 3% active Cocamidopropyl Betaine (Table 4).







TABLE 4







Test formulation for the sensory handwashing test:









Formulation Example












U
V
W
X















Texapon ® NSO-IS, 28%,
32.0%
32.0%
32.0%
32.0% 


(INCI: Sodium Laureth


Sulfate, BASF)


TEGO ® Betain F 50, 38%,
8.0%
8.0%
8.0%
8.0%


(INCI: Cocamidopropyl


Betaine, Evonik)


Sodium Chloride
1.5%
1.5%
1.5%
1.5%


Citric Acid
0.2%
0.2%
0.2%
0.2%


Water, demineralized
58.3%
55.3%
55.3%
54.55% 


Polyglycerol partial ester
—
3.0%
—
—


Example 1


Polyglycerol partial ester
—
—
3.0%
—


Example 6 (non-inventive)


NATRAGEM ® S 140,
—
—

3.75% 


80% with 20% water,


(Example 9, non-inventive)









The sensory test results are summarized in Table 5.







TABLE 5







Results of the handwashing test:










Test formulation













U
V
W
X

















Foaming behaviour
3.3
3.6
3.6
3.5



Foam volume
3.0
3.1
3.1
3.1



Foam creaminess
2.7
3.9
3.9
4.0



Skin feel during washing
2.9
3.2
3.0
3.0



Rinseability
3.5
3.6
3.6
3.5



Skin smoothness
2.0
2.8
2.6
2.5



Skin softness
2.3
3.0
2.7
2.7



Skin smoothness after 3 min
3.0
3.6
3.3
3.2



Skin softness after 3 min
2.9
3.6
3.4
3.5










It is evident from the test results in Table 5 that the inventive formulation V using the inventive polyglycerol partial ester of Example 1 is superior, surprisingly, in skin smoothness and softness application properties in comparison to the comparative formulations W and X according to the prior art. Skin feel during washing is also best with formulation V. In this light, the results of the inventive formulation V can be designated as very good and show a distinct improvement compared to the prior art.
Example Formulations:
The formulation examples given in the tables below show exemplary representatives of a large number of possible compositions according to the invention.
If the preparation of the formulation requires the separate preparation or mixing of formulation constituents beforehand, this is termed multiphase preparation. If a two-phase preparation is required, the two phases are labelled A and B in the stated tables. In the case of three- or more-phase processes, the phases are called A, B, C etc. Unless stated otherwise, the data in the tables are data in % by weight. In the following formulation examples, the data or % by weight are based on the respective active substance. Some products, however, are commercially available as solutions, especially in water, such that in these cases more of the commercial products were used accordingly, depending on the active content.
“Product Example 1-9” correspond to “polyglycerol partial esters Example 1-9”.







TABLE 6





Bath cream


















Water
to 100.0%



Sodium Laureth Sulfate
8.0%



Coco-Glucoside
4.0%



Cocamidopropyl Betaine
4.0%



Product Example 2
1.5%



PEG-18 Glyceryl Oleate/Cocoate
2.0%



Perfume Spicy Herbs
0.2%



Polyglyceryl-4 Caprate
0.5%



Citrus Aurantifolia (Lime) Oil
0.2%



Linalool
0.1%



Coumarin
0.1%



Glycerol
0.5%



Glycol Distearate
0.5%



Styrene/Acrylates Copolymer
0.2%



Tocopherol
0.1%



Preservative
q.s.



Citric Acid
to pH 5.2

















TABLE 7





Shower cream


















Water
to 100.0%



Glycerol
4.0%



Sodium Laureth Sulfate
4.0%



Cocamidopropyl Betaine
3.5%



Product Example 3
1.8%



Coco-Glucoside
1.8%



Ricinus Communis Seed Oil (seed)
0.2%



Glyceryl Oleate
0.5%



Polyglyceryl-6 Caprylate; Polyglyceryl-3 Cocoate;
1.0%



Polyglyceryl-4 Caprate; Polyglyceryl-6 Ricinoleate



Argania Spinosa Kernel Oil
0.1%



Butyrospermum Parkii Butter Extract
0.1%



Limonene
0.1%



Perfume
0.2%



Acrylates/C10-30 Alkyl Acrylate Crosspolymer
0.2%



Hydroxypropyl Methylcellulose
0.2%



Styrene/Acrylates Copolymer
0.2%



Sodium Hydroxide
0.2%



Glycol Distearate
0.4%



Silica
0.2%



Tocopherol
0.1%



Preservative
q.s.



Citric acid
to pH 5.2

















TABLE 8





Bath oil


















Water
to 100.0%



Sodium Laureth Sulfate
6.0%



Cocamidopropyl Betaine
6.0%



Cocamide DEA
2.5%



Sodium Trideceth Sulfate
2.2%



Product Example 2
1.0%



Perfume
0.5%



PEG-40 Hydrogenated Castor Oil
0.2%



Trideceth-9
0.2%



Sodium Lauroamphoacetate
0.5%



Benzophenone-4
0.2%



Cocamide MEA
0.4%



Propylene Glycol
0.5%



Disodium EDTA
0.1%



Sodium Chloride
0.6%



Glycerol
0.5%



Benzyl Alcohol
0.4%



Sodium Cocoyl Glutamate
0.4%



Phenoxyethanol
0.2%



Xanthan Gum
0.2%



Carbomer
0.2%



Lactic Acid
0.3%



Magnesium Chloride
0.1%



Coumarin
0.1%



Citric Acid
to pH 5.2



Preservative
q.s.

















TABLE 9





Shower cream


















Water
to 100.0%



Sodium Laureth Sulfate
8.0%



Glycerol
2.5%



Cocamidopropyl Betaine
2.5%



Product Example 3
2.0%



Decyl Glucoside
1.5%



Perfume
q.s.



Sodium Chloride
1.5%



PEG-40 Hydrogenated Castor Oil
0.5%



Glycine Soja Oil
0.1%



Helianthus Annuus Seed Oil
0.1%



Lecithin
0.2%



Coco-Glucoside
0.5%



Glyceryl Oleate
0.2%



Coumarin
0.1%



Preservative
q.s.

















TABLE 10





Body shampoo



















Phase A
Product Example 2
3.0%




Salvia Officinalis (Sage) Oil
0.3%




Perfume
0.1%



Phase B
Sodium Cocoamphoacetate
3.5%



Phase C
Water
to 100.0%




Acrylates/C10-30 Alkyl Acrylate
0.9%




Crosspolymer



Phase D
Sodium Lauroyl Methyl Isethionate
5.0%




Capryl/Capramidopropyl Betaine
1.5%




Citric Acid
1.2%



Phase E
Water
10.0% 




Polyquaternium-7
0.3%




Preservative
q.s.

















TABLE 11





Body shampoo



















Phase A
Product Example 1
4.0%




Lavandula Angustifolia (Lavender) Oil
0.2%




Perfume
0.2%



Phase B
Water
to 100.0%



Phase C
Sodium Cocoamphoacetate
4.0%



Phase D
Water
30.0% 




Acrylates/Beheneth-25 Methacrylate
1.7%




Copolymer




Sodium Lauroyl Methyl Isethionate
4.0%




Disodium Lauryl Sulfosuccinate
1.7%



Phase E
Preservative
q.s.

















TABLE 12





Shampoo



















Phase A
Product Example 2
3.0%




Orange Oil
0.3%




Perfume
0.1%



Phase B
Water
to 100.0%



Phase C
Disodium Cocoamphodiacetate
5.0%



Phase D
Glycerol
1.0%




Xanthan Gum
0.7%




Water
25.0%



Phase E
Water
10.0%




Acrylates/Beheneth-25 Methacrylate
2.0%




Copolymer



Phase F
Water
10.0%




Polyquaternium-10
0.3%



Phase G
Cocamidopropyl Betaine
5.0%




Preservative
q.s.

















TABLE 13





Shampoo



















Phase A
Product Example 2
5.0%




Lemongrass Oil
0.5%



Phase B
Water
to 100.0%



Phase C
Perfume
0.2%




Polyglyceryl-4 Caprate
2.0%



Phase D
Water
20.0%



Phase E
Sodium Laureth Sulfate
8.0%



Phase F
Water
10.0%




Cocamidopropyl Betaine
4.0%




PEG-120 Methyl Glucose Dioleate
1.2%



Phase G
Water
10.0%




Sodium Chloride
0.9%




Polyquaternium-10
0.2%



Phase H
Citric Acid
to pH 5.5



Phase I
Preservative
q.s.

















TABLE 14





Shower gel



















Phase A
Product Example 2
3.0%




Mentha Piperita (Peppermint) Oil
0.2%




Rosemary Oil
0.2%




Perfume
0.1%



Phase B
Water
to 100.0%



Phase C
Sodium Cocoamphoacetate
5.5%



Phase D
Lauryl Glucoside
4.5%



Phase E
Coco-Glucoside
1.3%



Phase F
Sodium/Disodium Cocoyl Glutamate
3.5%




Water
10.0%




Glycerol
0.8%



Phase G
Water
10.0%




Xanthan Gum
2.2%



Phase H
Citric acid
to pH 6.0



Phase I
Preservative
q.s.

















TABLE 15





Shampoo



















Phase A
Product Example 1
4.0%




Isopropyl Myristate
0.2%




Perfume
0.1%



Phase B
Water
to 100.0%



Phase C
Sodium Lauryl Sulfate
9.0%



Phase D
Cocamidopropyl Betaine
3.0%



Phase E
Cocamide MEA
2.0%




Xanthan Gum
0.2%




Water
10.0%



Phase F
Water
10.0%




Polyquaternium-10
0.2%



Phase G
Citric acid
to pH 5.5



Phase H
Preservative
q.s.

















TABLE 16





Cleansing Oil Shampoo


















Water
to 100.0%



Sodium Laureth Sulfate
6.0%



MIPA-Laureth sulfate
3.0%



Sodium Chloride
2.5%



Cocamidopropyl Betaine
2.5%



Polyglyceryl-6 Caprylate; Polyglyceryl-3 Cocoate;
2.5%



Polyglyceryl-4 Caprate; Polyglyceryl-6 Ricinoleate



Glycerol
2.5%



PEG-18 Castor Oil Dioleate
2.0%



Propylene Glycol; PEG-55 Propylene Glycol Oleate
2.0%



Product Example 2
2.0%



Laureth-5 Carboxylic Acid
1.0%



Persea Gratissima (Avocado) Oil
0.5%



Sodium benzoate
0.7%



Salicylic Acid
0.3%



Linalool
0.2%



alpha-Isomethyl Ionone
0.1%



Limonene
0.1%



Camellia Oleifera Seed Oil
0.1%



Citric Acid
to pH 5.0



Perfume, Dyes
q.s.

















TABLE 17





Shower Cream


















Water
to 100%



Glycerol
7.0%



Glycine Soya Oil
3.0%



Lauryl Glucoside
3.0%



Sodium Coco-Sulfate
3.0%



Product Example 2
2.5%



Alcohol
1.5%



Xanthan Gum
1.5%



Butyrospermum Parkii Butter Extract
1.0%



Sodium Cetearyl Sulfate
1.0%



Sodium Cocoyl Glutamate
1.0%



Disodium Cocoyl Glutamate
1.0%



Tocopherol
0.1%



Helianthus Annuus Seed Oil
0.3%



Limonene
0.1%



Benzyl Salicylate
0.1%



Linalool
0.1%



Dyes
q.s.

















TABLE 18





Shower Gel


















Water
to 100%



Sodium Coco-Sulfate
5.0%



Glycerol
4.0%



Lauryl Glucoside
4.0%



Sodium Lactate
2.5%



Product Example 3
2.0%



Polyglyceryl-4 Caprate
2.0%



Sodium Cocoyl Glutamate
2.0%



Disodium Cocoyl Glutamate
1.0%



Alcohol
1.0%



Prunus Cerasus Fruit Extract
1.0%



Limonene
0.1%



Coumarin
0.2%



Linalool
0.1%



Citral
0.1%



Dyes
q.s.

















TABLE 19





Liquid Soap


















Water
to 100%



Glycerol
4.0%



Alcohol
4.0%



Sodium Coco-Sulfate
3.0%



Lauryl Glucoside
3.0%



Product Example 1
2.0%



Xanthan Gum
1.5%



Mangifera Indica (Mango) Fruit Extract
0.5%



Limonene
0.1%



Linalool
0.1%



Dyes
q.s.

















TABLE 20





Shampoo for Children


















Water
to 100%



Sodium Coco Sulfate
7.0%



Decyl Glucoside
4.0%



Lactis Proteinum
2.5%



Sorbitan Caprylate
2.0%



Product Example 2
2.0%



Glycerol
2.0%



Sodium Lactate
2.0%



Alcohol
2.0%



Hydrolyzed Wheat Protein
0.3%



Hydrolyzed Wheat Starch
0.3%



Sodium Chloride
0.9%



Limonene
0.1%



Citral
0.1%



Phenethyl Alcohol
0.1%



Dyes
q.s.

















TABLE 21





Cream Soap


















Water
to 100%



Alcohol
7.0%



Coco-Glucoside
5.0%



Glycerol
5.0%



Product Example 1
2.5%



Disodium Cocoyl Glutamate
2.5%



Xanthan Gum
1.5%



Citric Acid
to pH 5.5



Malva Sylvestris Leaf Extract
1.0%



Glyceryl Oleate
1.0%



Sodium Cocoyl Glutamate
0.8%



Linalool
0.1%



Limonene
0.1%



Dyes
q.s.

















TABLE 22





Shower Crème


















Water
to 100%



Ammonium Lauryl Sulfate
11.0%



Product Example 2
3.5%



Aloe Barbadensis Leaf Juice
1.5%



Cocamidopropyl Betaine
1.5%



Decyl Glucoside
1.5%



Glycerol
1.0%



Prunus Amygdalus Dulcis (Sweet Almond) Oil
0.4%



Glyceryl Oleate
0.2%



Lauryl Glucoside
0.3%



Coco-Glucoside
0.4%



Benzyl Alcohol
0.2%



Benzoic Acid
0.2%



Dehydroacetic Acid
0.1%



Sodium Benzoate
0.3%



Potassium Sorbate
0.2%



Tocopherol
0.1%



Citric Acid
to pH 4.9



Perfume, Dyes
q.s.

















TABLE 23





Shower Crème
















Water
to 100%


Sodium Laureth Sulfate
9.0%


Product Example 2
3.0%


Cocamidopropyl Betaine
3.0%


Glycerol
1.0%


Glucose
0.5%


Prunus Amygdalus Dulcis (Sweet Almond) Oil
0.5%


Sodium Chloride
0.5%


Polyquaternium-7
0.3%


Styrene/Acrylates Copolymer
0.3%


PEG-200 Hydrogenated Glyceryl Palmate; PEG-7 Glyceryl
0.6%


cocoate


Citric Acid
to pH 5.5


Perfume, Dyes
q.s.
















TABLE 24





Care shower


















Water
to 100%



Sodium Laureth Sulfate
9.5%



Sodium Hydroxypropyl Starch Phosphate
2.5%



Product Example 2
2.0%



Cocamidopropyl Betaine
2.5%



Petrolatum
0.4%



Sodium Cocoyl Glycinate
0.9%



Lauric Acid
0.5%



Sodium Lauroyl Isethionate
0.7%



Glycerol
0.5%



Helianthus Annuus Seed Oil
0.2%



Olea Europaea Fruit Oil
0.1%



Sodium Chloride
0.5%



Stearic Acid
0.3%



Guar Hydroxypropyltrimonium Chloride
0.3%



Sodium Isethionate
0.1%



Tetrasodium EDTA
0.1%



Alumina
0.1%



Citric Acid
to pH 5.5



Perfumes, Dyes, Preservatives
q.s.

















TABLE 25





Shower Crème


















Water
to 100%



Sodium Coco-Sulfate
15.0%



Glycerol
3.5%



Product Example 3
3.5%



Glycine Soja Oil
0.3%



Coco-Glucoside
0.9%



Caprylic/Capric Triglyceride
0.1%



Xanthan Gum
0.8%



Prunus Amygdalus Dulcis Oil
0.1%



Sodium Cocoyl Glutamate
0.3%



Disodium Cocoyl Glutamate
0.5%



Sodium Cetearyl Sulfate
0.2%



Tocopherol
0.1%



Helianthus Annuus Seed Oil
0.1%



Alcohol
0.8%



Citral
0.1%



Geraniol
0.1%



Limonene
0.1%



Linalool
0.1%



Citric Acid
to pH 5.3



Perfume, Dyes
q.s.

















TABLE 26





Pampering Oil Bath


















Water
to 100.0%



Glycine Soya Oil
20.0%



Product Example 1
10.0%



Polyglyceryl-3 Palmitate
4.5%



Glyceryl Caprylate
4.5%



Simmondsia Chinensis Seed Oil
1.5%



Prunus Amygdalus Dulcis (Sweet Almond) Oil
1.0%



Triticum Vulgare Germ Oil
1.0%



Tocopherol
0.2%



Limonene
0.1%



Citral
0.1%



Dyes
q.s.

















TABLE 27





Deo



















Phase A
Product Example 2
3.0%




Isopropyl Palmitate
0.1%




Rosemary Oil
0.1%




Perfume
0.1%



Phase B
Phenoxyethanol
0.5%




Caprylyl Glycol
0.2%



Phase C
Water
50.0%




Hydroxyethyl Cellulose
0.7%




Sodium Hydroxide (10% in water)
0.2%



Phase D
Aluminium Chlorohydrate
19.0%



Phase E
Water
to 100.0%

















TABLE 28





Deo



















Phase A
Phenoxyethanol
0.5%




Methylisothiazolinone
0.001%




Aluminium Chlorohydrate
20.0%



Phase B
Hydroxyethyl Cellulose
1.0%




Water
to 100.0%



Phase C
Product Example 3
1.5%




Perfume Spicy Herbs
0.3%

















TABLE 29





Deo



















Phase A
Product Example 1
2.0%




Perfume Pink Grapefruit
0.2%



Phase B
Phenoxyethanol
0.5%




Caprylyl Glycol
0.2%



Phase C
Water
50.0%




Hydroxyethyl Cellulose
0.75%




Sodium Hydroxide (10% in water)
0.25%



Phase D
Aluminium Chlorohydrate
10.0%



Phase E
Water
to 100.0%

















TABLE 30





Antitranspirant Deo Roll-On

















Phase A
Polyglyceryl-6 Caprylate; Polyglyceryl-3 Cocoate;
4.0%



Polyglyceryl-4 Caprate; Polyglyceryl-6 Ricinoleate



Decyl Oleate
0.1%



Aloe Barbadensis Leaf Extract
0.1%



Glycine Soya Oil
0.1%


Phase B
Product Example 1
2.8%



Perfume
0.1%



Distearyl Ether
0.3%



Stearyl Alcohol
0.1%


Phase C
Aluminium Chlorohydrate
10.0%



Water
to 100.0%


Phase D
Phenoxyethanol
0.6%



Ethylhexylglycerin
0.2%
















TABLE 31





Anti-Transpirant Deo



















Phase A
Product Example 2
3.5%




Dicaprylyl Ether
0.2%




Geraniol
0.1%




Linalool
0.1%




Perfume Spicy Herbs
0.1%



Phase B
Propylene Glycol
1.0%




Butylene Glycol
0.5%




Water
5.0%




Palmitamidopropyltrimonium Chloride
1.5%



Phase C
Water
50.0%




Hydroxyethyl Cellulose
0.8%




Sodium Hydroxide (10% in water)
0.3%



Phase D
Aluminium Chlorohydrate
15.0%



Phase E
Water
to 100.0%

















TABLE 32





Deo



















Phase A
Product Example 1
2.8%




Dicaprylyl Ether
0.2%




Isoceteth-20
0.5%




Geraniol
0.1%




Allantoin
0.1%




Linalool
0.1%




Limonene
0.1%




Butylene Glycol
0.8%




Perfume Pink Grapefruit
0.1%



Phase B
Propylene Glycol
1.0%




Water
5.0%




Palmitamidopropyltrimonium Chloride
1.5%



Phase C
Water
50.0%




Glyceryl Isostearate
0.5%




PEG-150 Distearate
0.3%



Phase D
Aluminium Chlorohydrate
10.0%



Phase E
Water
to 100.0%

















TABLE 33





Formulation for Wet Wipes
















Butylene Glycol
1.0%


Glycerol
1.0%


Product Example 1
1.5%


Silicone Quaternium-22; Polyglycerol-3 Caprate; Dipropylene
0.5%


Glycol; Cocamidopropyl Betaine


Allantoin
0.2%


Maltodextrin
0.5%


Chamomilla Recutita Extract
0.1%


Phenoxyethanol; Ethylhexylglycerol
0.7%


Perfume
q.s.


Water
to 100.0%


Citric Acid, 30%
to pH 5.5
















TABLE 34





Solution for Wet Wipes
















Product Example 2
1.5%


Perfume
0.2%


Glycerol
2.0%


Sodium Lactate; Sodium PCA; Glycine; Fructose; Urea;
0.1%


Niacinamide; Inositol; Sodium Benzoate; Lactic Acid


Water
to 100.0%


Preservative
q.s.
















TABLE 35





Solution for Wet Wipes
















Product Example 3
3.0%


Polyglyceryl-4 Caprate
2.0%


Isopropyl myristate
0.3%


Phenoxyethanol; Methylparaben; Ethylparaben; Butylparaben;
0.2%


Propylparaben; Isobutylparaben


Perfume
0.1%


Propylene Glycol
2.0%


Water
to 100.0%


Cetrimonium bromide
0.1%
















TABLE 36





Solution for Wet Wipes


















Product Example 2
3.0%



Aloe barbadensis leaf extract
0.3%



Disodium Cocoamphodiacetate
0.5%



Perfume
0.2%



Propylene Glycol
2.5%



Hydrolyzed Silk
0.1%



Caprylyl/Capryl Glucoside
1.0%



Water
to 100.0%



Phenoxyethanol
0.5%



Dehydroacetic Acid
0.1%



Benzoic Acid
0.1%



Sodium Benzoate
0.4%

















TABLE 37





Make-up Remover


















Sodium Cocoamphopropionate
 5.0%



Propylene Glycol
35.0%



Product Example 1
30.0%



Glycerol
30.0%



Preservative
q.s.

















TABLE 38





Make-up Remover


















Cocamidopropyl Betaine
7.0%



Water
to 100.0%



Product Example 2
4.0%



Glycerol
8.0%



Citric Acid
to pH 5.5



Preservative
q.s.

















TABLE 39





Make-up Remover


















Capryl/Capramidopropyl Betaine
2.0%



Water
to 100.0%



Product Example 2
3.0%



Glycerol
3.0%



Citric Acid
to pH 5.5



Preservative
q.s.

















TABLE 40





Make-up Remover


















Polyglyceryl-4 Caprate
1.0%



Water
to 100.0%



Product Example 2
1.5%



Polyglyceryl-6 Caprylate; Polyglyceryl-3 Cocoate;
1.2%



Polyglyceryl-4 Caprate; Polyglyceryl-6 Ricinoleate



Propylene Glycol
1.0%



Glycerol
2.5%



Citric Acid
to pH 5.5



Preservative
q.s.

















TABLE 41





O/W Make-up remover wipe

















Phase A
Ethylhexyl Stearate; Phenoxyethanol; Polyglyceryl-4
4.0%



Laurate; Sorbitan Laurate; Dilauryl Citrate



Cetyl Ricinoleate
0.8%


Phase B
Water
to 100.0%



Glycerol
1.5%


Phase C
Product Example 3
1.0%


Phase D
Phenoxyethanol
0.2%



Perfume
q.s.



Preservative
q.s.
















TABLE 42





Micellar water


















Water
to 100.0%



Product Example 2
4.0%



Glycerol
1.5%



Disodium Cocoamphodiacetate
0.5%



Disodium EDTA
0.2%



Polyaminopropyl Biguanide
0.2%



Citric Acid, 30%
to pH 5.5

















TABLE 43





Micellar Solution Cleanser


















Water
to 100.0%



Butylene Glycol
5.0%



Coco-Glucoside
2.0%



Product Example 2
2.5%



Glycerol
1.0%



Allantoin
0.1%



Curcuma Longa (Turmeric) Root Extract
0.2%



Perfume
0.2%



Citric Acid, 30%
to pH 5.5

















TABLE 44





Cleansing Water


















Water
to 100.0%



Product Example 1
2.5%



Phenoxyethanol; Ethylhexylglycerol
0.9%



Perfume Pink Grapefruit
0.2%



Glycerol
0.5%



Disodium EDTA
0.2%



Citric Acid, 30%
to pH 5.5

















TABLE 45





Micellar water


















Water
to 100.0%



Product Example 2
3.0%



Glycerol
1.0%



Capryl/Capramidopropyl Betaine
1.5%



Disodium EDTA
0.2%



Perfume Pink Grapefruit
0.2%



Citric Acid, 30%
to pH 5.5

















TABLE 46







Further formulation examples


















46a
46b
46c
46d
46e
46f
46g
46h
46i
46j












Water
to 100%

















Product Example 1
2.5%
3.5%
3.5%
1.0%
3.0%
2.5%
5.0%
3.0%
3.5%
3.5%


Sodium Laureth Sulfate
9.0%
8.0%
9.0%
—
—
—
—
—
—
—


Sodium Lauryl Sulfate
—
—
—
6.0%
—
—
—
—
3.5%
—


Cocamidopropyl Betaine
—
2.0%
3.0%
5.0%
5.0%
6.0%
—
—
2.0%
7.5%


Sodium Cocoamphoacetate
3.0%
—
—
1.5%
4.5%
—
3.5%
—
3.5%
—


Lauryl Glucoside
—
—
—
—
3.5%
5.0%
3.0%
7.0%
—
—


Coco-Glucoside
—
1.5%
—
—
1.5%
1.0%
5.0%
2.5%
2.0%
—


Sodium Cocoyl Glutamate
—
—
—
—
—
1.0%
1.7%
5.0%
0.5%
—


Stearic Acid
—
—
1.0%
—
—
—
—
—
0.1%
3.5%


Sucrose Cocoate
0.5%
—
1.0%
1.2%
0.3%
0.2%
—
1.0%
1.0%
1.0%


Glycerol
0.5%
1.0%
0.5%
—
0.3%
0.5%
1.5%
1 0%
0.5%
1.0%


PEG-7 Glyceryl Cocoate
—
0.3%
—
—
—
—
—
—
—
0.5%


Trideceth-9
—
0.2%
—
—
0.2%
—
—
—
—
—


Polysorbate 20
—
—
0.5%
—
—
—
—
—
0.3%
0.2%


PEG-40 Hydrogenated
—
—
0.3%
—
0.5%
—
—
—
1.0%
—


Castor Oil


PEG-6 Caprylic/Capric
—
—
—
—
0.3%
—
—
—
—
0.2%


Glycerides


Polyglyceryl-4 Caprate
—
—
—
2.0%
—
0.5%
—
—
—
0.5%


Polyquaternium-10
—
0.2%
—
0.1%
—
—
—
0.2%
0.2%
—


Hydroxypropyl Guar
0.2%
—
0.3%
0.2%
0.2%
0.3%
0.2%
0.1%
—
—


Hydroxypropyltrimonium


Chloride


Silicone Quaternium-22
—
—
0.3%
—
0.3%
—
—
—
—
—


Dimethicone
—
0.3%
—
—
—
—
—
—
0.1%
—


Amodimethicone
—
0.1%
—
0.1%
0.1%
—
—
—
0.5%
—


Argania Spinosa Oil
—
—
0.1%
0.1%
0.1%
—
0.2%
—
—
—


Glycol Distearate
—
0.5%
—
—
0.5%
—
0.3%
—
0.5%
0.5%


Isostearamide MIPA;
1.0%
—
—
1.5%
—
—
0.3%
—
1.0%
0.5%


Glyceryl Laurate


Sodium Chloride
0.5%
1.8%
2.0%
0.5%
1.5%
1.8%
0.2%
1.0%
—
0.5%


PEG-120 Methyl Glucose
0.3%
2.5%
1.0%
—
1.2%
—
—
—
0.5%
—


Dioleate


Xanthan Gum
—
—
0.5%
0.6%
—
0.7%
2.0%
1.0%
—
—


Cellulose
—
—
—
0.1%
—
0.1%
0.1%
0.2%
0.1%
—


Zinc Pyrithione
—
0.1%
—
—
—
—
—
—
0.1%
—


Benzophenone-4
—
0.1%
0.1%
0.1%
0.1%
—
0.1%
—
0.1%
—


Tetrasodium EDTA
0.1%
0.1%
—
0.1%
0.1%
—
0.1%
—
0.1%
—


Caffeine
—
0.1%
0.1%
—
—
0.1%
—
—
0.1%
—


Coumarin
—
0.1%
0.1%
—
0.1%
0.1%
0.2%
0.1%
0.1%
—


Panthenol
0.1%
0.1%
0.1%
0.1%
0.1%
0.1%
—
0.1%
0.1%
0.1%


Isopropyl Myristate
—
—
—
0.3%
—
0.1%
—
—
—
0.2%


Linalool
—
—
0.1%
0.1%
—
0.1%
0.1%
—
0.1%
—


Citrus Limon (Lemon) Peel
0.1%
—
0.1%
—
—
0.3%
—
0.2%
0.1%
0.2%


Oil


Orange Oil
—
0.2%
—
—
0.2%
—
—
0.2%
—
—


Limonene
—
0.1%
—
—
—
—
0.1%
—
0.1%
—








Citric Acid
to pH 5.5


Perfumes, Dyes,
q.s.


Preservatives
















TABLE 47







Further formulation examples


















47a
47b
47c
47d
47e
47f
47g
47h
47i
47j












Water
to 100%

















Product Example 2
7.0%
3.0%
2.0%
4.0%
4.0%
2.5%
4.0%
3.5%
3.0%
3.0%


Sodium Lauryl Sulfate
—
8.0%
9.5%
—
—
—
—
3.5%
—
—


Coco-Betaine
—
5.0%
—
5.5%
—
—
—
3.0%
—
—


Cocamidopropyl Betaine
—
—
3.0%
—
5.0%
—
—
—
3.0%
2.0%


Sodium Cocoamphoacetate
—
—
2.5%
3.0%
—
5.0%
—
3.0%
4.0%
—


Disodium Lauryl
—
—
1.0%
—
—
—
—
1.2%
—
—


Sulfosuccinate


Coco-Glucoside
—
—
—
3.0%
5.0%
4.0%
5.0%
1.0%
—
2.0%


Sodium Cocoyl Glutamate
—
—
—
2.5%
—
3.0%
4.5%
0.5%
2.5%
0.3%


Sodium Cocoyl Glycinate
—
—
—
—
5.0%
—
3.5%
—
2.0%
7.0%


Sodium Lauroyl Methyl
—
—
—
1.0%
—
1.5%
—
1.0%
0.5%
0.5%


Isethionate


Stearic Acid
—
—
0.2%
—
—
—
—
0.1%
—
0.5%


Sucrose Cocoate
0.5%
0.4%
—
1.0%
—
0.2%
0.2%
0.3%
1.0%
0.3%


Glycerol
1.5%
0.3%
0.5%
0.5%
0.8%
0.5%
1.0%
0.5%
0.5%
1.0%


PEG-40 Hydrogenated
—
1.0%
—
—
—
—
—
0.3%
—
—


Castor Oil


Polyglyceryl-4 Caprate
1.0%
—
—
0.5%
—
2.5%
—
—
0.9%
—


Polyquaternium-11
—
0.2%
—
—
0.1%
—
—
0.2%
—
0.3%


Guar
—
—
0.3%
0.2%
0.2%
0.3%
0.2%
0.1%
0.2%
—


Hydroxypropyltrimonium


Chloride


Dimethicone
—
0.3%
—
—
—
—
—
0.2%
—
—


Aminopropyl Dimethicone
—
0.3%
0.5%
—
—
—
—
0.3%
—
—


Helianthus Annuus Seed Oil
0.1%
—
0.1%
—
—
0.1%
—
0.2%
—
—


Dicaprylylether
0.5%
0.3%
—
—
—
0.2%
0.3%
0.5%
—
—


Sodium Hydroxypropyl
0.2%
—
—
—
—
0.5%
—
—
—
0.5%


Starch Phosphate


Palmitamidopropyltrimonium
—
—
0.5%
—
—
—
—
0.5%
0.4%
—


Chloride


Bis-(Isostearoyl/Oleoyl
0.5%
0.3%
—
—
—
—
0.5%
—
—
—


Isopropyl) Dimonium


Methosulfate


Glycol Distearate
0.2%
0.1%
0.2%
—
0.4%
—
—
—
0.5%
0.2%


PEG-3 Distearate
—
0.5%
—
—
—
—
—
0.5%
—
—


Acrylates/C10-30 Alkyl
0.5%
—
0.4%
—
0.5%
—
—
—
0.5%
—


Acrylate Crosspolymer


Sodium Hydroxide, 25%
0.6%
—
0.6%
—
0.8%
—
—
—
0.7%
—


Cocamide MEA
—
0.8%
1.0%
1.0%
—
0.4%
0.6%
1.0%
—
0.3%


Sodium Chloride
0.3%
0.8%
0.5%
—
0.5%
0.5%
—
1.0%
0.5%
1.0%


Propylene Glycol; PEG-55
—
2.5%
—
—
—
—
—
0.8%
—
—


Propylene Glycol Oleate


Xanthan Gum
0.2%
—
0.2%
1.2%
0.5%
—
1.5%
0.2%
1.0%
0.9%


Algin
—
—
—
—
0.7%
1.2%
—
—
0.5%
—


Benzophenone-4
—
0.1%
0.2%
—
—
—
—
0.2%
—
0.1%


Menthol
0.1%
—
0.1%
—
—
—
—
0.1%
0.1%
0.1%


Caffeine
—
0.1%
0.1%
0.1%
0.1%
—
—
0.1%
—
0.1%


Benzyl Alcohol
0.1%
—
—
—
0.1%
0.1%
—
0.1%
—
—


Hydrolyzed Wheat Protein
—
—
0.1%
0.1%
0.1%
0.2%
0.2%
0.1%
—
—


Octopirox
0.2%
—
—
—
—
0.1%
—
—
—
—


Salicylic acid
0.1%
—
—
—
0.1%
0.1%
—
—
0.1%
—


1,2-Hexanediol
—
—
—
0.2%
—
0.5%
0.5%
0.2%
—
—


Isopropyl Myristate
—
0.3%
—
0.2%
—
—
—
0.5%
0.3%
—


Linalool
—
0.1%
0.1%
0.1%
—
0.1%
0.1%
0.1%
0.1%
—


Citrus Limon (Lemon) Peel
0.1%
—
0.1%
0.3%
—
0.2%
—
0.1%
0.1%
0.2%


Oil


Orange Oil
—
0.2%
—
0.1%
0.5%
—
—
—
—
—


Panthenol
0.1%
0.1%
—
0.1%
0.1%
0.1%
0.1%
0.1%
0.1%
0.1%








Citric Acid
to pH 5.2


Perfumes, Dyes,
q.s.


Preservatives
















TABLE 48







List of raw materials used








INCI
Trade name, company





1,2-Hexanediol
Hydrolite-6 841129, Symrise


Acrylates/Beheneth-25 Methacrylate
Novethix L-10 Polymer, Lubrizol


Copolymer


Acrylates/C10-30 Alkyl Acrylate
TEGO Carbomer 841 SER, Evonik


Crosspolymer
Nutrition & Care GmbH, 100%


Algin
Hydagen 558 P, BASF


Allantoin
Allantoin, DSM Nutritional Products, Inc.


Aloe Barbadensis Leaf Juice
Aloe-Con UP 40, Florida Food Products



Inc.


alpha-Isomethyl Ionone
alpha-Isomethylionone, Chemos GmbH


Alumina
Aeroxide Alu C, Evonik Nutrition & Care



GmbH


Aluminum Chlorohydrate
Locron L, Clariant


Ammonium Lauryl Sulfate
Empicol AL 70, Albright & Wilson UK



Limited


Aminopropyl Dimethicone
ABIL Soft AF 200, Evonik Nutrition &



Care GmbH


Amodimethicone
DC 949, Dow Corning, 100%


Argania Spinosa Oil (Argania Spinosa
Argan Oil, DSM Nutritional Products Ltd.


Kernel Oil)


Benzophenone-4
Uvinul MS 40, BASF Corporation


Benzoic Acid
OriStar BZA, Orient Stars LLC


Benzyl Alcohol
Microcare BNA, THOR PERSONAL



CARE SAS


Benzyl Salicylate
Seridefrizz Intense, Cheemyunion



Quimica Ltda.


Bis-(Isostearoyl/Oleoyl Isopropyl)
VARISOFT EQ 100, Evonik Nutrition &


Dimonium Methosulfate
Care GmbH, 100%


Butylene Glycol
Butylene Glycol, Oxea Corparation


Butyrospermum Parkii Butter Extract
Cosmosil 600, International Cosmetic



Science Centre


Caffeine
Caffeine, Merck KGaA/EMD Chemicals,



Inc.


Camellia Oleifera Seed Oil
Camellia Sasanqua Oil, Ikeda Corporation


Caprylyl Glycol
Sensiva SC 10, Schülke& Mayr GmbH


Caprylyl/Capryl Glucoside


Capryl/Capramidopropyl Betaine
TEGO Betaine 810, Evonik Nutrition &



Care GmbH, 38%


Caprylic/Capric Triglyceride
TEGOSOFT CT, Evonik Nutrition & Care



GmbH, 100%


Carbomer
TEGO Carbomer 140, Evonik Nutrition &



Care GmbH, 100%


Cellulose
Arbocel A300, J. Rettenmaier & Sohne


Cetyl Ricinoleate
TEGOSOFT CR, Evonik Nutrition & Care



GmbH, 100%


Cetrimonium Bromide
Rhodaquat M-242B/99, Rhodia


Chamomilla Recutita (Matricaria) Extract
Recentia CR, AkzoNobel Global Personal



Care


Citral
Citral FF, Symrise AG


Citric Acid
Citric Acid USP Granular, DSM



Nutritional Products, Inc.


Citrus Aurantifolia (Lime) Oil
AEC Lime Oil, A & E Connock,



Perfumery & Cosmetics Ltd.


Cocamide DEA
REWOMID DC 212 S, Evonik Nutrition



& Care GmbH, 100%


Cocamide MEA
REWOMID D 212, Evonik Nutrition &



Care GmbH, 100%


Cocamidopropyl Betaine
TEGO Betain F 50, Evonik Nutrition &



Care GmbH, 38%


Coco-Glucoside
Plantacare 818 UP, BASF Cognis, 51%,


Coco-Betaine
Dehyton AB 30, BASF Cognis, 31%


Coumarin
Rhodiascent extra pure, Rhodia Organics


Curcuma Longa (Turmeric) Root Extract
TEGO Turmerone, Evonik Nutrition &



Care GmbH


Decyl Glucoside
Plantacare 2000 UP, BASF Cognis


Decyl Oleate
TEGOSOFT DO, Evonik Nutrition &



Care GmbH, 100%


Dicaprylyl Ether
Cetiol OE, BASF Cognis


Dehydroacetic Acid
Unisept DHA (Universal Preserv-A-



Chem, Inc.)


Dimethicone
DC 200 Fluid 100 cSt, Dow Corning,



100%


Disodium Cocoamphodiacetate
Rewoteric AM 2 C NM, Evonik Nutrition



& Care GmbH


Disodium Cocoyl Glutamate
Planatpon ACG LC, BASF Cognis


Disodium EDTA
Dissolvine NA-2-P, AkzoNobel Global



Personal Care


Disodium Lauryl Sulfosuccinate
REWOPOL SB F 12 P, Evonik Nutrition



& Care GmbH, 95%


Distearyl Ether
Cosmacol SE, Sasol Germany GmbH


Ethylhexylglycerin
Sensiva SC 50, Schuelke & Mayr GmbH


Ethylhexyl Stearate; Phenoxyethanol;
TEGO Wipe Flex, Evonik Nutrition &


Polyglyceryl-4 Laurate; Sorbitan Laurate;
Care GmbH


Dilauryl Citrate


Geraniol
Nerol 800, International Flavors &



Fragrances Inc.


Glucose
Organic Biovert Substrate, Lonza


Glycerol
Glycerol EP, vegetable, Spiga Nord,



99.7%


Glyceryl Caprylate
Dermosoft GMCY, Dr. Straetmans


Glyceryl Isostearate
Peceol Isostearique, Gattefosse


Glyceryl Oleate
TEGIN O V, Evonik Nutrition & Care



GmbH


Glycine Soya (Soybean) Oil
Cropure Soybean, Croda Europe, Ltd.


Glycol Distearate
TEGIN G 1100 Pellets, Evonik Nutrition



& Care GmbH, 100%


Guar Hydroxypropyltrimonium Chloride
Cosmedia Guar C 261, BASF Personal



Care and Nutrition Gmbh/Jaguar C-17,



Rhodia Inc. et al


Helianthus Annuus (Sunflower) Seed Oil
AEC Sunflower Oil, A & E Connock,



Perfumery & Cosmetics Ltd.


Hydrolyzed Silk
Crosilk 10000, Croda Inc.


Hydrolyzed Wheat Protein
Gluadin WLM, BASF Cognis


Hydrolyzed Wheat Starch
Cropeptide W, Croda, Inc.


Hydroxyethyl Ethylcellulose
Structure Cel 4400 E, AkzoNobel Global



Personal Care


Hydroxypropyl Guar
Jaguar C-162, Rhodia, 100%


Hydroxypropyltrimonium Chloride


Hydroxypropyl Methylcellulose
TEGOCEL HPM 50, Evonik Nutrition &



Care GmbH, 100%


Isoceteth-20
TEGO Alkanol IC 20, Evonik Nutrition &



Care GmbH, 100%


Isopropyl Myristate
TEGOSOFT M, Evonik Nutrition & Care



GmbH, 100%


Isopropyl Palmitate
TEGOSOFT P, Evonik Nutrition & Care



GmbH, 100%


Isostearamide MIPA; Glyceryl Laurate
ANTIL SPA 80, Evonik Nutrition & Care



GmbH, 100%


Lactic Acid
AEC Lactic Acid, A & E Connock,



Perfumery & Cosmetics Ltd.


Lactis Proteinum
AEC Whey Protein, A & E Connock,



Perfumery & Cosmetics Ltd.


Laureth-5 Carboxylic Acid
Marlowet 1072, Sasol Germany GmbH -



Marl


Lauric Acid
Prifrac 2920, Croda Europe, Ltd.


Lauryl Glucoside
Plantacare 1200 UP, BASF Cognis, 50%


Lavandula Angustifolia (Lavender) Oil
AEC Lavender Oil, A&E Connock Ltd.


Lecithin
AEC Lecithin Powder, A & E Connock,



Perfumery & Cosmetics Ltd.


Limonene
Dipentene No. 122, Hercules Inc.


Citrus Limon (Lemon) Peel Oil
Fragrance Resources


Cymbopogon Schoenanthus (Lemongrass)
AEC Lemongrass Oil, A&E Connock Ltd.


Oil


Linalool
Lipofresh, Lipo Chemicals, Inc.


Magnesium Chloride
OriStar MCL, Orient Stars LLC


Maltodextrin
Farmal MD 10, Corn Products



International


Malva Sylvestris (Mallow) Leaf Extract
Herbasec Mallow Leaves, Cosmetochem



International AG


Mangifera Indica (Mango) Fruit Extract
Mango Extract, Draco Natural Products


Menthol
OriStar MC, Orient Stars LLC


Methylisothiazolinone
Microcare MT, Thor Specialties, Inc.


Mentha Piperita (Peppermint) Oil
AEC Peppermint Oil, A&E Connock Ltd.


MIPA-Laureth Sulfate
Zetesol 2056, Zschimmer & Schwarz



GmbH


Octopirox
Octopirox, Clariant Intl. Ltd.


Olea Europaea (Olive) Fruit Oil
Cropure Olive, Croda Europe, Ltd.


Orange Oil
Fragrance Resources


Palmitamidopropyltrimonium Chloride
VARISOFT PATC, Evonik Nutrition &



Care GmbH, 60%


Panthenol
D-Panthenol USP, BASF, 100%


PEG-120 Methyl Glucose Dioleate
ANTIL 120 Plus, Evonik Nutrition & Care



GmbH, 100%


PEG-150 Distearate
REWOPAL PEG 6000 DS A, Evonik



Nutrition & Care GmbH, 100%


PEG-18 Castor Oil Dioleate
Marlowet CG, Sasol Germany GmbH


PEG-18 Glyceryl Oleate/Cocoate
ANTIL 171, Evonik Nutrition & Care



GmbH, 100%


PEG-200 Hydrogenated Glyceryl
REWODERM LI S 80, Evonik Nutrition


Palmate; PEG-7 Glyceryl Cocoate
& Care GmbH, 100%


PEG-3 Distearate
TEGIN D 1102, Evonik Nutrition & Care



GmbH, 100%; Cutina TS, BASF Cognis,



100%


PEG-40 Hydrogenated Castor Oil
TAGAT CH 40, Evonik Nutrition & Care



GmbH, 100%


PEG-6 Caprylic/Capric Glycerides
TEGOSOFT GMC-6, Evonik Nutrition &



Care GmbH, 100%


PEG-7 Glyceryl Cocoate
TEGOSOFT GC, Evonik Nutrition & Care



GmbH, 100%


Perfume Pink Grapefruit
Fragrance Resources


Perfume Spicy Herbs
Fragrance Resources


Persea Gratissima (Avocado) Oil
Cropure Avocado, Croda Europe, Ltd.


Petrolatum
Merkur 115, Sasol Wax GmbH


Phenethyl Alcohol
Etaphen, Vevy Europe SpA


Phenoxyethanol
S&M Phenoxyethanol, Schulke & Mayr



GmbH


Phenoxyethanol; Ethylhexylglycerol
Euxyl PE 9010, Schulke & Mayr GmbH


Phenoxyethanol; Methylparaben;
Euxyl K 300, Schuelke & Mayr GmbH


Ethylparaben; Butylparaben;


Propylparaben; Isobutylparaben


Polyaminopropyl Biguanide
Microcare MBG, Thor


Polyglyceryl-3 Palmitate
Dermofeel PP, Dr. Straetmans


Polyglyceryl-4 Caprate
TEGOSOFT PC 41, Evonik Nutrition &



Care GmbH, 100%


Polyglyceryl-6 Caprylate; Polyglyceryl-3
TEGO Solve 61, Evonik Nutrition & Care


Cocoate; Polyglyceryl-4 Caprate;
GmbH,


Polyglyceryl-6 Ricinoleate


Polyquaternium-10
Polymer JR 400, Amerchol, 100%


Polyquaternium-11
Dehyquart CC 11, BASF Personal Care



and Nutrition Gmbh/Luviquat PQ 11 PN,



BASF Corporation


Polyquaternium-7
Merquat 550, Nalco, 100%


Polysorbate 20
TEGO SML 20, Evonik Nutrition & Care



GmbH, 100%


Potassium Sorbate
Euxyl K 712, Schülke & Mayr GmbH


Propylene Glycol
Euxyl K 320, Schülke & Mayr GmbH


Propylene Glycol; PEG-55 Propylene
ANTIL 141 Liquid, Evonik Nutrition &


Glycol Oleate
Care GmbH


Prunus Amygdalus Dulcis (Sweet
Cropure Almond, Croda Europe, Ltd.


Almond) Oil


Prunus Cerasus (Bitter Cherry) Fruit
Prunus Cerasus Fruit, Kirschen Extract,


Extract
Botanica GmbH


Ricinus Communis Seed Oil
Lipovol CO, Lipo Chemicals


Rosemary Oil
Fragrance Resources


Salvia Officinalis (Sage) Oil
AEC Sage Oil, A&E Connock Ltd.


Salicylic Acid
OriStar SCA, Orient Stars LLC


Silica
Aerosil 130, Evonik Degussa GmbH


Silicone Quaternium-22
ABIL T Quat 60, Evonik Nutrition & Care



GmbH, 65%


Silicone Quaternium-22; Polyglycerol-3
ABIL ME 45, Evonik Nutrition & Care


Caprate; Dipropylene Glycol;
GmbH, 30%


Cocamidopropyl Betaine


Simmondsia Chinensis (Jojoba) Seed Oil
AEC Jojoba Oil Refined, A & E Connock,



Perfumery & Cosmetics Ltd.


Sodium Benzoate
Euxyl K 712, Schülke & Mayr GmbH


Sodium Cetearyl Sulfate
Lanette E, BASF Personal Care and



Nutrition GmbH


Sodium Cocoamphoacetate
REWOTERIC AM C, Evonik Nutrition &



Care GmbH, 32%


Sodium Cocoamphopropionate
REWOTERIC AM KSF 40, Evonik



Nutrition & Care GmbH, 40%


Sodium Coco-Sulfate
Texapon HC G, BASF


Sodium Cocoyl Glutamate
Plantapon ACG HC, BASF Cognis


Sodium Cocoyl Glycinate
Hostapon SG, Clariant; Amilite GCS-11,



Ajinomoto


Sodium/Disodium Cocoyl Glutamate
PERLASTAN SC 25 NKW,



Schill&Seilacher, 25%,


Sodium Hydroxide
Unichem SOHYD, Universal Preserv-A-



Chem, Inc.


Sodium Hydroxypropyl Starch Phosphate
Pure-Gel, Grain Processing Corporation


Sodium Isethionate
Hostapon SI, Company Clariant



International Ltd


Sodium Lactate
Sodium Lactate Solution About 50%,



Merck KGaA/EMD Chemicals, Inc.


Sodium Lactate; Sodium PCA; Glycine;
LACTIL, Evonik Nutrition & Care GmbH


Fructose; Urea; Niacinamide; Inositol;


Sodium Benzoate; Lactic Acid


Sodium Laureth Sulfate
Texapon NSO, BASF Cognis, 28%


Sodium Lauroamphoacetate
ColaTeric SLAA, Colonial Chemical Inc


Sodium Lauroyl Isethionate
Yongan SLI, Huanggang Yongan



Pharmaceutical Co., Ltd


Sodium Lauroyl Methyl Isethionate
Iselux, Innospec Active Chemicals


Sodium Lauryl Sulfate
Texapon LS 35, BASF Cognis, 30%


Sodium Trideceth Sulfate
Rhodapex EST-30, Rhodia


Sorbitan Caprylate
Sorbon S-10, Toho Chemical Industry Co.,



Ltd.


Stearic Acid
Pristerene 4922, Croda Europe, Ltd.


Stearyl Alcohol
TEGO Alkanol 18, Evonik Nutrition &



Care GmbH


Styrene/Acrylates Copolymer
Acudyne HS, The Dow Chemical



Company


Sucrose Cocoate
TEGOSOFT LSE 65 K, Evonik Nutrition



& Care GmbH, 100%


Tetrasodium EDTA
Versene 100, The Dow Chemical



Company


Tocopherol
Euxyl K 700, Schülke & Mayr GmbH


Trideceth-9
Marlipal O 13/90, Sasol Germany GmbH -



Marl


Triticum Vulgare Germ Oil
Cropure Wheatgerm, Croda Europe, Ltd.


Xanthan Gum
Keltrol CG-SFT, CP Kelco, 100%


Zinc Pyrithione
Microcare ZP, THOR PERSONAL CARE



SAS

## Claims

1. A polyglycerol partial ester obtainable by esterification of a polyglycerol with a carboxylic acid mixture comprising:
a) at least one short-chain dicarboxylic acid having 2 to 12 carbon atoms, and
b) at least one saturated fatty acid having 6 to 14 carbon atoms, wherein the molar ratio of polyglycerol to dicarboxylic acid to saturated fatty acid is in a ratio of from 3.1:1.0:0.5 to 14:1.0:6.0.

2. The polyglycerol partial ester according to claim 1, wherein the polyglycerol has an average degree of condensation N of 1.5 to 9.

3. The polyglycerol partial ester according to claim 1, wherein the polyglycerol used has a hydroxyl number of 1500 to 900 mg KOH/g.

4. The polyglycerol partial ester according to claim 1, wherein the short-chain dicarboxylic acid is selected from aliphatic, linear dicarboxylic acids, in particular oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, and dodecanedioic acid.

5. The polyglycerol partial ester according to claim 1, wherein the saturated fatty acid is selected from unbranched, unsubstituted fatty acids.

6. The polyglycerol partial ester according to claim 1, wherein the esterification the molar ratio of a) to b) is
from 1.0:0.7 to 1.0:3.0.

7. The polyglycerol partial ester according to claim 1, wherein at 1 bar it has a turbidity point of 45 to 75° C.

8. The polyglycerol partial ester according to claim 1, wherein it has an HLB value of 13 to 17.

9. The polyglycerol partial ester according to claim 1, wherein it has a surface tension of less than 28 mN/m in 1.0% aqueous solution at 20° C.

10. The polyglycerol partial ester according to claim 1, wherein it has a saponification number of 70 to 199 mg KOH/g.

11. The use of at least one polyglycerol partial ester according to claim 1 as solubilizer, particularly in cosmetic or pharmaceutical preparations.