CA2064482A1

CA2064482A1 - Use of alkylglycoside sulfosuccinates for the production of cosmetic preparations and cleaning agents

Info

Publication number: CA2064482A1
Application number: CA002064482A
Authority: CA
Inventors: Mathias Hintz; Hans-Jurgen Kohle; Christl Moller; Thomas Salomon; Joachim Weigand
Original assignee: Individual
Current assignee: Witco Surfactants GmbH
Priority date: 1991-04-04
Filing date: 1992-03-31
Publication date: 1992-10-05
Also published as: DK0507004T3; EP0507004B1; GR3015961T3; DE59105273D1; ATE121286T1; DE4110852A1; ES2073106T3; EP0507004A1

Abstract

Abstract:

Use of alkvlalycoside sulfosuccinates for the production of cosmetic preparations and cleaning agents The invention relates to the use of alkylglycoside sulfosuccinates of the general formula (1) R is a linear, saturated or unsaturated hydrocarbon radical having 1 - 18 C atoms or where R1 is H or R and x is 1 - 10 R2 is a linear, saturated or unsaturated acyl radical having 8 - 22 C atoms R3, independently of one another, are H and at least once can be the radical [CO-CH(SO3-)-CH2-COO-]2K+ and R4, independently of one another, can be H or CH3 n is a number between 1 and 6 and y1-4 can be 0 - 5, where n(y1+y2+y4)+y3 = n(1-20)+y3, and K+ is any desired cation of an alkali metal (Na), alkaline earth metal, ammonium or H
for the production of cosmetic preparations.

Description

~. 2~4~2 Use of alkylglvcoside sulfosuccinates for the ~roduction of cosmetic pre~arations and cleanina agents The invention relates to the use of alkoxylated sulfosuccinates containing e~ter groups and based on alkyl glycosides for the production of mild cosmetic preparations and aqueous compositions which contain these compounds.
Cosmetic preparations, in particular those which come within the area of hair and body cleaning, such as shower baths, foam baths, hair shampoos, baby shampoos, baby baths and liquid soaps, contain as cleaning components mainly anionic surfactants such as carboxylates, alkyl sulfates and alkyl ether sulfates.
These preparations should clean the skin surface, preferably only the film adhering to it, which can consist of body secretions such as perspiration and fats, flakes of skin or depo~ited dirt from the environment.
The cleaning agents should in no case dry out the skin, irritate it or impair its natural function.
As the preparations can lead, however, during their frequent - in recent years almost daily - use to irritations of the skin, use is frequently additionally made, in order to improve the skin and eye mucosa compatibility, of so-called mild surfactants such as, for example, betaines, protein derivatives, ampholytes, alkyl ether carboxylates and sulfosuccinates.
Especially for baby care agents and baby shampoos and preparations for sensitive skin, particular value is 2 ~ 8 2 placed on extremely low contents of substances irrita~ing the skin and eye mucosa. The anionic surfactants conventionally used because of their excellent cleaning and foam-forming properties can be rendered substantially milder in their irritant action by means of the known mild cosurfactants, but in practice improvements, in particular in the way of eye mucosa compatibility, are still required.
In high concentrations or on their own, the mild surfactants are substantially irritation-free, but then do not have foaming and cleaning properties suitable for practical use and have unsatisfactory viscosities.
A further criterion for the utilizability of the surface-active substances is their toxicity. The toxicity lies in the surfactants themselves or products thereof formed by interaction with the constituents of the recipe.
As a result of increased environmental awareness, products are additionally required which are based on natural, renewable raw substances, have no toxicity whatsoever and can be rapidly and completely degraded in municipal sewage plants without toxic intermediates.
GB Patent 2,011,462 di~closes polyalkoxylated mono- and dicarboxylates of ~-methylglucosides, the only surfactant disclosed being GLUCAMATE-SSE-20 from Amerchol - a mixture of the mono- and distearate of ~-methyl-glucoside. It is used in ~kin-compatible preparations for removing make-up from the eyes.

~ ~ 206~ 2 German Published Specification 3,336,760 describes mixtures of at least one oligomeric alkyl-glucoside ether containing an alkyl radical having 8 - 10 C atoms, ethoxylated methylglucoside dioleate, alkyl- or hydroxyalkyl polyglycosides containing an alkyl radical having 11 - 18 C atoms and between 3 - 25 glycoside units and at least one nonionic polymer from the group comprising the alkyl celluloses, polyhydroxyalkyl celluloses, poly-~-alanines and polyvinylpyrrolidone as mild hair- and body-cleaning agents.
In practice, high molecular weight compounds sometimes exhibit application problems: they are very often difficult to dissolve in water and necessitate a relatively large outlay on incorporation; occasionally it is difficult to obtain the desired viscosity immediately or the formulations tend to be "stringy" and produce a sticky feeling on the skin. Some of these disadvantages can be due to preparation and could possibly be overcome by appropriate apparatus measures and careful monitoring of the course of the process.
The ob~ect of the present invention is to overcome these disadvantages of the prior art and to make available mild, skin-compatible cosmetic preparations, in particular those which come within the area of hair- and body-cleaning.
This ob~ect is achieved by the alkoxylated sulfosuccinates containing ester groups and based on alkyl glycosides additionally used according to the 206~g~

invention. The invention therefore relates to the use of alkylglycoside sulfosuccinates of the general formula (l) Rq C~2 -O- (CH~ -CH-~- ), 4 _~<2 r 1 1 ;, (t~L~ H3 ) -n- ! -CH (: H-(~ ?.
/
C~ -- CH
L
R3 ~ 2 (OC2 H3 ) -~i o- (r2 H3 R4 R' R is a linear, saturated or unsaturated hydrocarbon radical having 1 - 18, preferably 1 - 10, in particular 1 - 4 C atoms or -(CHz-CH-O)x-Rl where R1 iB H or R and x i8 1 - 1 0, preferably 1 - 5.
R2 i8 a linear, saturated or unsaturated acyl radical having 8 - 22 C atoms, preferably 12 - 18 C atoms R3, independently of one another, are H and at least once can be the radical tCO-CH( S03- )-CH2-COO-]2R+ and R4, independently of one another, can be H or CHa n is a number between 1 and 6, preferably 1 and 3 and y~ - 4 can be 0 - S, where n (yl+yZ+y4 ) +y3 = n(1-20)+y3, preferably n(l-lO)+y3, in particular n(1-3)+y3, and R+ is any desired cation of an alkali metal (Na), alkaline earth metal, ammonium or H

2~644~2 for the production of cosmetic preparations and cleaning agents.
The invention further relates to aqueou~
preparation~ containing A) 5 - 20 % by weight of at least one of the compounds according to the general formula ~1) ?~

( CC: H J ) ~ ^ U _ r I \, / !
! ;
R3Y2 (OC2r~ O ~-(C2:;3O)YI?.
I ~ R ~
R is a linear, saturated or unsaturated hydrocarbon radical having 1 - 18, preferably 1 - 10, in particular 1 - 4 C atom~ or -(CH2-CH2-0)x-Rl where Rl i8 H or R and x i~
1 - 10, preferably 1 - 5.
R2 is a linear, saturated or unsaturated acyl radical having 8 - 22 C atoms, preferably 12 - 18 C atoms R3,independently of one another, are H and at lea~t once can be the radical [C0-CH(S03-)-CH2-C00-]2X~ and R4,independently of one another, can be H or -CH3 n is a number between l and 6, preferably 1 and 3 and yl~4 can be 0 - 5, where n(yl+y2+y4)+y3= n(l-20)+y3, preferably n(l-lO)~y3, ~064~82 ~+ is any desired cation of an alkali metal (Na), alkaline earth metal, ammonium or H
B) 1 - 5 % by weight of at least one thickener C) O - 10 ~ by weight of an electrolyte salt D) O - 10 % by weight of customar~ auxiliaries and additives.
E) 55 - 94 ~ by weight of water.
Further embodiments of the invention are characterized by the claims.
One starting substance for the preparation of the additionally used compounds of the general formula (1) according to the invention are commercial monomers and oligomers of glucose, for example glucose syrup from Cerestar.
The degree of polymerization of the glucose varies according to the process and manufacturer and is in the range 1 - 10 (n = 1 - 10), such that the compounds according to the invention are also mixtures of these various degrees of polymerization. Although the maximum degree of polymerization i8 at n = about 10, the largest part has a degree of polymerization (n~ of lesa than 5.
The mean value of n can therefore also be a decimal number, that is to say lie between two integers.
The degrees of polymerization claimed according to the invention of n = 1 to 6 therefore also comprise the comparatively small amounts with values >6. Those preferred according to the invention are degrees of polymerization where n ~3 and in particular 1 - 2 with a 206~8~

center around 1 - l.S.
These glycosides are etherified or transetherified by generally customary processes (cf.
US Patent 4,704,453, EP-A-0,301,298).
The group R of the glycoside is preferably an alkyl or alkenyl group having 1 - 10, in particular 1 -4 C atoms, and can optionally be replaced by higher groups having up to 18 C atoms. R can furthermore be a polyether group of the structure -(CH2-CH2-O-~x-Rl, in which R1 is H or R and x can assume values between 1 - 10, preferably 1 - 5.
In a second step the reaction of one mol of fa~ty acid or fatty acid methyl or fatty acid ethyl ester respectively is carried out per glycoside unit. Instead of the fatty acids or their methyl or ethyl esters, the natural fats and oils, that is to ~ay their glycerol esters, can also be employed.
The fatty acids used are the monobasic acids having 8 - 22 C atoms - preferably the naturally occurring acids - such as lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, ricinoleic acid, coconut fatty acid or their mixtures (compare J. Am. Oil Chemists' Soc. 38, 517 - 520 (1961) and EP-A 0,190,779).
The glycoside esters are alkoxylated, preferably ethoxylated or propoxylated, by processes known per se (J. Am. Oil Chemists' Soc. 38, 517 - 520 (1961), US
Patent 3,640,998). The ethoxylation or propoxylation can .

.

2~482 also be carried ou~ before the introduction of the ester function. The amounts of ethylene oxide and/or propylene oxide are chosen such that the rate of addition is between 1 and 20 per glycoside molecule, values according to the invention preferably being >5, in particular 8 - 25. The reaction to give the sulfosuccinate is carried out with maleic anhydride and subsequent sulfonation with sodium sulfite according to processes known per se (compare German Published Specification 2,700,072).
Reaction is carried out in this case with one mol of maleic anhydride per mol of hydroxyl group to be reacted at 60 - 80C until the reaction is complete. The maleic acid hemiester is then added to an agueous sodium sulfite solution (1 equivalent of sulfite per equivalent of hemiester) and sulfonated at 60 - 80C until the sulfite has completely reacted. The aqueous product is then adjusted to neutral pH.
While commercial sulfosuccinates can only be dissolved in water in concentrations up to about 40 % by weight, the compounds according to the invention surprisingly have the advantage that they can be prepared in concentrations of 50 % by weight and higher as clear, low-viscosity solutions.
These compounds, which can be additionally used on their own or in a mixture, can be employed in concentrations of 5 - 20, preferably of 6 - 12 % by weight, relative to the total mixture.

2 ~ 8 2 The number of anionic groups in the molecule is affected by the manner in which the glycoside molecules are linked to one another. If the glycoside rings are linked to one another in the 1,4- or 1,3-position, it is simpler for steric reason~ to substitute all the hydroxyl groups than if the linkage is effected in the 1,6- or 1,2-position.
Although theoretically 2n+1 anionic groups can be introduced into the glycoside ester, 2n to n groups are preferred according to the invention.
The mixtures according to the invention are in general aqueous compositions or aqueous alcoholic solutions, creams, emulsions or gels and can still contain the auxiliaries and additives customary in each case for adaptation to the intended application and which, apart from in aqueous cleaning agents, such as mild washing-up liquids used by hand, are in particular additionally used for the production of cosmetic preparations in the area of hair- and body-cleaning, that i8 to say for shower baths, foam baths, shampoos, liquid soaps, baby care agents and baby detergents.
These are foam stabilizers such as polysaccharides, carboxyvinyl polymers, polyvinyl-pyrrolidones, fatty acid partial glyceride polyglycol ethers, protein-fatty acid condensates; pearl luster and clouding agents such as fatty alcohols, ethylene glycol distearates, monoesters of polyhydric alcohols with higher fatty acid~, polystyrene emulsions; complexing -'' 2 ~ 2 agents or sequestering agents such as salts of ethylene-diaminetetraacetic acid; preservatives such as sorbic acid, citric acid, ascorbic acid, chlorhexidine, 8-hy-droxyquinoline and its salts, benzalkonium chloride, dimethylalkylbenzylammonium chloride and small amounts of fragrances, colorants, skin cosmetic active substances, vegetable extracts and buffer substances.
Thickeners additionally used according to B) can according to the invention be commercial fatty acid partial glyceride polyglycol ethers such as REWODERNP LI
420, REWODERNP LI 48 (trademark of REWO Chemische Werke GmbH, Steinau an der Strafle3 in amounts from 1 to 10, preferably from 2 to 4 % by weight, relative to the total mixture.
Suitable electrolyte salts are all alkali metal, alkaline earth metal and ammonium salts which are soluble at 20C in amounts of at least 1 % by weight. Those preferred are sodium chloride, magnesium chloride and ammonium chloride, which can be additionally employed in amounts up to about 10 % by weight, preferably 1 - 5 % by weight, relative to the total formulation.
The content of wash-active substance (B-WAS) given in the following examples is titrated by the customary two-phase titration with benzalkonium chloride against Methylene Blue as indicator (cf. S. R. Epton, Nature (London), 160, 1967, p. 795).
~ he hydrolysis number is a measure of the free and bound acids contained in fats and technical fatty . . 20~82 acids. It gives the number of milligrams of potassium hydroxide which axe necessa~y to hydrolyze 1 gram of substance or technical fatty acids (mg of ROH/g). The values are determined by the standard methods of the German Society for Fat Chemistry (DGF): DGF C-V3.
The hydroxyl value is used to determine the content of hydroxyl groups and gives the number of milligrams of potassium hydroxide which are necessary to neutralize the acetic acid consumed by 1 gram of substance during the acetylation (mg of KOH/g). The values are determined by the DGF standard method DGF
C-V17A.
The solids content is determined by drying to constant weight at 105C.

Pre~aration of the compounds accordina to the invention Exam~le 1 Preparation of butvlalucoside coconut fatty acid ester 8 g of R2CO3 are added to 826 g (3.5 mol) of n-butyl~lucoside and the reaction mixture is heated to 120C. 750 g of coconut methyl ester are added dropwise to the reaction mixture at 50 mbar over the course of 2 h and it is then reacted for 4 h at 120C and 30 mbar.
The resulting methanol is immediately removed by distillation during the course of this. A yellow, highly viscous material having the following analytical data results:

.

2~6~482 Hydrolysis value 110 mg of KO~/g Hydroxyl value 430 mg of KOH/g Example 2 Preparation of the PolyethYlene oxide ether 463 g of (1.05 mol) of butylglucoside ester from Example 1 are treated with 2.3 g of KOH and treated in portions with 464 g (10.5 mol) of ethylene oxide at 120C
in an autoclave so that the pressure is at most 5 bar. A
highly viscous yellow material having the following analytical values results:
Hydrolysis value 54 mg of KOH/g Hydroxyl value 223 mg of KOH/g Exam~le 3 Pre~aration of the sulfosuccinate 258 g (0.3 mol) of butylglucoside ester ethoxylate from Example 2 are stirred with 57.6 g (0.6 mol) of maleic anhydride at 70C for 2 h. The maleic acid hemiester is then added to a solution of 350 g of water at 60C containing 74.1 g (0.6 mol) of Na2SO3 and stirred at this temperature until the SOz content of the solution is <0.01 %. A clear solution having a 48.3 ~
solids content and 43.5 ~ Benzavlon wash-active substance (B-WAS) results.
The following examples were carried out following Examples 1 - 3.

2~482 ExamPle 4 258 g (0.3 mol) of butylglucoside ester ethoxylate from Example 2 are reacted as described in Example 3 with 29 g (0.3 mol) of maleic anhydride and then sulfonated in a solution of 300 g of water containing 37 g (0.3 mol) of Na2S03. The solution has a solids content of 49 % and a B-WAS of 41 %.

Example 5 258 g (0.3 mol) of butylglucoside ester ethoxylate from Example 2 are reacted as described in Example 3 with 87 g (0.9 mol) of maleic anhydride and then sulfonated with a solution of 400 g of water containing 111 g (0.9 mol) of Na2S03. The solution has a solids content of 47 % and a B-WAS of 43 %.

Example 6 200 g (0.3 g mol) of butylglucoside ester ethoxylate (as example 2, but ~Y = 5) are reacted with 59 g (0.6 mol) of maleic anhydride at 80C. A~ described in Example 1, the hemiester is then sulfonated in a solution of 330 g of water and 77 g (0.61 mol) of Na2S03.
The sulfosuccinate has 49 % solids and a B-WAS of 41 %.

Example 7 200 g (0.3 mol) of the butylglucoside ester ethoxylate as described in Example 6 are reacted with 88.5 g (0.9 mol) of maleic anhydride at 80C. Analogously 2~S~g2 to Example 3, the sulfonation is carried out in 400 g of water and 116 g of Na2SO3. The sulfosuccinate has 50 %
solids and a B-WAS of 44 %.

Example 8 200 g (0.3 mol) of butylglucoside ester ethoxylate as in Example 6 are reacted with 29.5 g (0.3 mol) of maleic anhydride at 75C. Analogously to Example 3, sulfonation is carried out in 270 g of water containing 38 g (0.3 mol) of Na2SO3. The sulfosuccinate has 48.2 ~ solids together with 28.1 % B-WAS.

Example 9 220 g (0.5 mol) of butylglucoside ester from Example 1 are reacted analogously to Example 3 with 49 g (0.5 mol) of maleic anhydride and then sulfonated in 500 g of water containing 63 g (0.5 mol) of Na2SO3. The sulfosuccinate has 38.3 ~ solids and a B-WAS of 23.2 %.

Example 10 238 g (1 mol) of butylglucoside are treated with 0.5 g of potassium hydroxide and treated in portions with 440 g (10 mol) of ethylene oxide at 140C in an autoclave 80 that the maximum pressure does not exceed 5 bar. A
viscous~ yellow product having a hydroxyl value of 360 results.

2~4~

Example 11 678 g (1 mol) of the product from Example 10 are treated with 3 g of K2CO3 and heated to 120C under an N2 atmosphere. Under a vacuum of 100 mbar, 210 g (0.95 mol) of coconut methyl ester are added dropwise to the reaction solution over the course of about 2 h and the mixture is then reacted for a further 4 h at 120C. The resulting methanol is continuously removed from the system. A pale-yellow, viscous material having the following analytical values re~ults:
Hydrolysis value 60 Hydroxyl value 240 Example 12 890 g (l mol) of butylglucoside ethoxylate ester from Example 11 are reacted as described in Example 3 with 98 g (1 mol) of maleic anhydride and then sulfonated with a solution of 1100 g of water and 126 g of Na2SO3. A
pale solution having a solids content of 49 % and a B-WAS
of 31 % results.

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- 2~482 All recipes are given in percent by weight calculated relative to solids.

Statement of the surfactants employed according to the Cosmetic, Toiletry and Fragrance Association (CTFA) standards:
1) Disodium laureth sulfosuccinate 2) Sodium laureth sulfate 3) Cocoamidopropyl betaine 4) PEG-80 glyceryl tallowate 5) Glyceryl stearate 6) PEG-200 glyceryl tallowate mod.

7) Disodium cocoamphodiacetate Basic reciPe~ hair shamPoo Example 4 or 12 2 - 6 parts by weight REWOPOL~ NL 3-28 6 - 15 "
REWODERM~ LI S 756) 1 - 3 "
demin. water to 100 Basic reciPe, babv shampoo or shampoo for sensitive skin Example 4 or 12 3 - 8 parts by weight REWOTERIC AM 2 C NM7) 2 - 10 "

REWOTERIC AM B 13 H3) 4 - 8 "
REWODERM? LI 48-504) 1 - 4 "
demin. water to 100 -- 2 ~ 8 2 Basic recipe cream Example 4 or 12 1 - 5 parts by weight Glycerol monodistearate 2 - lO "
Cetyl alcohol l - 4 "
Paraffin oil 3.5E 4 - 12 "
Glycerol 1 - 5 "
demin. water to 100 Preservative as required Basic recipe shower bath Example 4 or 12 2 - 10 parts by weight REWOTERIC AM B 13 2 - 8 "
REWOPOL NL 3-28 5 - 15 "
REWODERN~ LI 48-50 1 - 4 "
demin. water to lOO

Basic reci~e washina-up lia,uid Example 12 l - 5parts by weight REWOPOL NL 3-28 1 - 30 "
REWOTERIC AM CAS 1 - 5 "
REWOPOL LA 6 1 - 10 "
demin. water to lOO

Application check Shower bath The glyco~ide derivatives developed have been asse~sed in the test recipe by a test panel of 20 persons (female and male) with respect to 2~6~

- foaming power, foam structure - feeling of the wet skin - feeling of the dried skin for skin compatibility (zein ~alues) compare:
Z. Gotte "Hautvertraglichkeit von Tensiden, gemessen am Loseverm~genfur Zein~(skin compatibility of surfactants, measured by dissolving power for zein) Chem. Phys. Appl.
Surface Active Subst. Proc. Int. Congr. 4 (1964~ 83 - 90.
Assessment scheme: ~ 200 mg of N/100 ml = non-irritating 200 - 400 mg of ~100 ml = slightly irritating > 400 mg of N/100 ml = irritating Plate washina test 1. Princi~le The number of artificially soiled plates which can be cleaned in a washing-up liquid solution until the liquor is exhausted is determined.

2. Production of the test soilina 2.0 parts by weight of technical oleic acid, 49.9 parts by weight of wheatmeal flour and 0.1 part by weight of the dye Sudan Red are successively stirred into a melt of 48.0 parts by weight of lard at S0C and homogenized.

3. Coatina the Plate The plates are first washed, rinsed with clear water and additionally rinsed with isopropanol. 2 g of .

~ - 20~82 the test soiling at 40C are then uniformly distributed on each dried plate on the inner surface using a brush and then stored for 24 h at 20C and 65 ~ relative atmospheric humidity.

4. Pre~aration of the washina liauors Washing liquor A:

8 1 of tap water at 50C having a German hardness ~dH) of 10 and a content of the test substance to be checked of 0.02 ~ by weight (relative to solids) is placed in a bowl and stirred for 2 min with a blade stirrer at 300 rpm in such a way that sufficient foam results.

Washing liquor Bs 10 1 of cold tap water (20C 10dH) which is continuously replaced by running fresh water (5 l/min) are placed in a second bowl.

S. Washina ~rocess The soiled plates are washed in 6uccession for 30 seconds each under the surface of the washing liquor A
using the washing brush. They are then rinsed by simple immersion in liquor B. Washing is carried out until liquor A is exhausted. This is recognized by the disappearance of the foam, the visually recognizable remaining of soil particles on the washed plates or the floating of black or red fat particles on the surface of ~ , ' , ' - ' .
.

2 ~ 8 2 the liquor A.

6 ! Assessment The number of plates washed perfectly clean is determined by sub~ective assessment of at least 3 persons. The following are stated:
Number of plates as stated Concentration of the washing liquor in g/l 0.02 % solids content Water hardness in mmol of Ca~/l 10dH
Washing temperature in C 50 , ~ ' :
.

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- 206~2 Hair_shampoo The glycoside derivatives developed have been assessed in the recipe by 10 volunteers experienced in application for:
- Combability - Volume of the hair and hold of the hairstyle Recipe 1 2 3 Example 4 4.5 _ _ Example 12 _ 4.5 _ REWOPOI~ NL 3-282) 10.5 10.5 15 REWODERM~ LI S 756) 2 2 2 demin. water 83 83 83 pH ad~usted with citric acid to 6.5 6.5 6.5 Combability 5 6 2 Volume of the hair Hold of the hairstyle 6 5 3 Assessment of combability:
1 - 3 Difficult to comb through: the hair offers considerable resistance to the combing process 4 - 7 The hair can be combed through relatively easily, combing resistance is decrea~ed, adequate for a conditioning shampoo depending on the hair type 8 - 10 Reserved for the subsequent aftertreatment by so-called hair-rinse agents 20~82 Assessment of the hair volume and of the hold of the _airstyle 1 - 3 The hair is dry or dull and lifeless; poor hold of the hairstyle 4 - 7 The hair is soft and bouffant at the same time together with a good hold of the hairstyle 8 - 10 The hair i8 soft and smooth, but too loose, as a result the hairstyle does not hold well.
- The assessment was carried out by a graded point system, where the abovementioned assessment represents the arithmetic mean.

Skin cream Use of aqueous sulfosuccinates based on glycoside as emulsifiers in 0/W emulsions HLB value Example 4 about 16 Example 12 about 16 Determination according to W.C. Griffin ("Calculation of Surface Active Agents by HLB", Journal Soc. Cosm.
Chem. 1, 311 (1949)).

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2 ~ 8 2 Assessment of the properties on the skin by 10 volunteers; more than 80 % assessed the stable test recipes 1 and 2 - as easy to spread on the ~kin - as easily absorbed into the skin - the skin is smooth and soft, without becoming sticky and greasy. The comparison recipe No. 4 is not assessed the same and is furthermore unstable.

Babv shamPoo or hair and bodv shampoo for sensitive skin Recipe 1 2 3 Example 4 6 _ _ Example 12 _ 6 _ REWOTERIC~ AM 2C NM7) 6 6 6 REWOTERIC~ AM B 133) 4 4 4 REWODERM~ LI 48-504~ 2 2 2 REWOPOL2 NL 3-282) _ _ 6 demin. water to 100 to 100 to 100 pH adjusted with citric acid to 6.5 6.5 6.5 Zein values, mg of N/100 ml ~70 ~70 about 150 Skin roughness according to slight slight di~tinct Padberg~) rough- rough- rough-ening ening ening The recipe shown is a "non-irritating" washing solution only "slightly roughening" the skin. The assessment "slightly roughening" is the lowest which can --- 2 ~ 8 2 be obtained with surfactants by the method shown.
Testing of skin compatibility according to Padberg, J. Soc. Cosm. Chem. 20, 719 - 728 (1969) Assessment of skin roughness according to Padberg:
Grade 1 very slight roughening - does not differ from the blank area Grade 2 slight roughening - % Padberg below 50 Grade 3 distinct roughening - % Padberg over 50 Grade 4 heavy roughening - does not differ significantly from the sodium lauryl sulfate area (comparison substance) ' -~' ' .

20~82 Test recipe: Skin-compatible washina-up aaents for manual use Recipe 1 2 3 4 .

Example 12 _ 3 1.5 _ REWOPOI~ NL 3-28 7) 18 18 18 18 REWOTERIC~ AM CAS 3) 1 . 5 _ 1.5 _ REWOPOL LA 6 4) 1 . 5 _ _ 3 Water to 100 to 100 to 100 to 100 Plate washing test Number of plates 12 20 18 12 Zein values (skin compat-ibillty) 220 lg5 220 250 .
'~

Foam height (mm) 195/185 190/180 195/190 190/180 + 0.S ml of Olive oil 190/180 190/180 195/185 190/180 + 1.0 ml of Olive oil 190/185 190/180 190/180 190/180 :' . .
- ... ~.

Claims

1. The use of alkylglycoside sulfosuccinates of the general formula (1) R is a linear, saturated or unsaturated hydrocarbon radical having 1 - 18 C atoms or where R1 is H or R and x is 1 - 10 R2 is a linear, saturated or unsaturated acyl radical having 8 - 22 C atoms R3, independently of one another, are H and at least once can be the radical [CO-CH(SO3-)-CH2-COO-]2K+ and R4, independently of one another, can be H or CH3 n is a number between 1 and 6 and y1-4 can be 0 - 5, where n(y1+y2+y4)+y3 = n(1-20)+Y3, and K+ is any desired cation of an alkali metal (Na), alkaline earth metal, ammonium or H

for the production of cosmetic preparations.

2. The use of alkylglycoside sulfosuccinates as claimed in claim 1, wherein R is an alkyl radical having 1 - 4 C atoms R2 is an acyl radical of the mixture of natural coconut fatty acids R3, independently of one another, are H and at least once can be the radical (CO-CH(SO3-)-CH2-COO-]2X+ and R4, independently of one another, can be H or CH3 n is 1 - 2 y1-4 is 0 - 5, where n(y1+y2+y4)+y3 = n(1-3)+y3 K+ is any desired cation of an alkali metal (Na), alkaline earth metal, ammonium or H, for the production of cosmetic preparations and cleaning agents.

3. An aqueous preparation containing A) 5 - 20 % by weight of at least one of the compounds according to the general formula (1) R is a linear, saturatea or unsaturatea hydrocarbon radical having 1 - 18 C atoms or -(CH2-CH-O)X-R1 where R1 is H or R and x is 1 - 10 R2 is a linear, saturated or unsaturated acyl radical having 8 - 22 C atoms R3,independently of one another, are H and at least once can be the radical [CO-CH(SO3-)-CH2-COO-]2K+ and R4,independently of one another, can be H or CH3 n is a number between 1 and 6 and y1-4 can be 0 - 5, where n (y1+y2+y4)+y3 = n(1-20)+Y3, and K+ is any desired cation of an alkali metal (Na), alkaline earth metal, ammonium or H
B) 1 - 5 % by weight of at least one thickener C) 0 - 10 % by weight of an electrolyte salt D) 0 - 10 % by weight of customary auxiliaries and additives E) 55 - 94 % by weight of water.

4. An aqueous hair-cleaning agent, containing a) 1 - 10 parts by weight of at least one of the compounds of the general formula (1) and b) 1 - 20 parts by weight of at least one surfactant from the group comprising the nonionic, amphoteric, zwitterionic or ionic surfactants and optionally c) 0.1 - 10 parts by weight of thickeners, fragrances, preservatives, colorants, vegetable extracts and other additives and auxiliaries and d) water to 100.

5. An aqueous shower bath, containing a) 1 - 10 parts by weight of the compounds of the general formula (1) b) 1 - 20 parts by weight of at least one nonionic, amphoteric, zwitterionic or ionic surfactant and c) 0.1 - 10 parts by weight of thickeners, fragrances, preservatives, colorants, vegetable extracts and other additives and auxiliaries and optionally d) water to 100.

6. An aqueous washing-up liquid, containing a) 1 - 10 parts by weight of at least one of the compounds of the general formula (1) and b) 1 - 30 parts by weight of at least one surfactant from the group comprising the nonionic, amphoteric, zwitterionic and ionic surfactants and optionally c) 0.1 - 10 parts by weight of thickeners, fragrances, preservatives, colorants, vegetable extracts and other additives and auxiliaries and optionally d) water to 100.

7. A skin cream, containing a) 1 - 10 parts by weight of at least one of the compounds of the general formula (1) and b) 1 - 10 parts by weight of at least one surfactant from the group comprising the nonionic, - 34 _ amphoteric, zwitterionic and ionic surfactants and optionally c) 0.5 - 20 parts by weight of vegetable or mineral oils, or ester oils d) 1 - 10 parts by weight of consistency-imparting agent e) 0.5 - 5 parts by weight of fragrances, colorants or preservatives f) water to 100.

8. A baby shampoo, containing a) 1 - 10 parts by weight of at least one of the compounds of the general formula (1) and b) 0.1 - 20 parts by weight of at least one surfactant from the group comprising the nonionic, amphoteric, zwitterionic and ionic surfactants and optionally c) 0.1 - 10 parts by weight of thickeners, fragrances, preservatives, colorants, vegetable extracts and other additives and auxiliaries and optionally d) water to 100.