CA2104387A1 - Fatty acid monoglyceride polyglycol ether sulphosuccinates, their method of preparation and their use - Google Patents

Abstract

ABSTRACT OF THE DISCLOSURE

The invention concerns fatty acid monoglyceride polyglycol ether sulphosuccinates of general formula (1), wherein R may be the same or different and stands for H
or -CH3, R1 stands for (.alpha.) or (.beta.), R2 stands for R1 or H, R3 is an acyl residue with 8 to 22 carbon atoms which is optionally substituted and/or contains multiple bonds, a, b and c may be the same or different and are equal to 0 to 10, a + b + c being greater than or equal to 1, and X+
stands for H+ or a cation. The invention also concerns their preparation and their use.

Description

WO 92/18470 -- 1 ~ PCT/EP92~00047 The invention relates to novel fatty acid mono-glyceride polyglycol ether sulfosuccinates, a process for their preparation, and their use a3 cleaning agents and for cosmetic preparations.
Cosmetic preparations, in particular those which come within the area of hair and body cleaning, such a3 shower baths, foam baths, hair shampoo~ and liquid ~oap~, contain as cleaning components mainly anionic surfactants such as carboxylate~, alkylsulfates and alkyl ether sulfate~, and sulfosuccinates.
These preparations should clean the skin surface, preferably only the film adhering to it, which may consist of bodily secretions such as perspiration and fats, ~kin flakes or deposited dirt from the environment.
Th~ cleaning agents should in no case dry out the skin, irritate it or impair its natural function.
However, since the preparations in their frequent - in recent years almost daily - use can lead to irrita-tions-o~ the skin, to improve skin compatibility and compatibility with the mucous membrane of the eye fre-quently so-called mild surfactants are additionally u~ed, such as, for example, betaines, protein derivatives, ampholytes, alkyl ether carboxyIa~es and sulfosuccinates.
In p~rticular for baby care compositions and baby shampoos, particular value i~ placed on extremely low .
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2 1 ~ t7 contents of substances irritating the skin and mucousmembrane of the eye. The conventional anionic surfactants used because of their excellent cleaning and foam-formation properties can indeed be substantially moderated in their irritant action by mean~ of the known mild co-surfactant~, but in practice Lmprovements are still required, in particular in respect of compatibility with the mucous membrane of the eye.
In high concentrations or on their own, the mild surfactants are indeed #ubstantially irritation-free, but then exhibit no practical foaming and cleaning properties and unsatisfactory viscosities.
A further criterion for the utility of the surface-active substance~ is their toxicity. The toxicity resides in the ~urfactants themselve~ or their product~
fonmed by interaction with the constituents of the recipe.
Thus, the fatty acid alkanolamides which until now tended to be additionally used because of their advantageou~ application and skin-caring properties have recently still been employed only reluctantly in cosmetic preparations since the re~idual content o~ free diethanolamine remaining during preparation cannot be excluded and thus gives rise to nitrosamine formation (EP-A-0,306,843). N-Nitrosamine~ axe carcinogenic in anLmal experiments.
As a result of increased environmental awareness, products are furthermore required which are based on natural renewable raw materials, exhibit no toxicity and 2 ~ ~ 3 ~ ~

can be broken down in the municipal sewage plants rapidly and completely without toxic intermediates.
The products introduced in practice based on E~olyhydric alcohols such as, for example, the mono-a~nd/or difatty acid ester alkoxylates based on glycerol do have low toxicities and are mild products which do not irritate the skin, but which in re~pect of their cleaning action do not fulfill the requirements in practice.
The object of the present invention i8 to over-come these disadvantages of the prior art and to make available mild, skin-compatible cleaning agents for domestic use and industry, and cosmetic preparation~, in particular those which come within the area of hair and body cleaning.
This object i8 achieved by the sulfosuccinates based on glycerol and containing alkoxylated e~ter groups additionally used according to the invention. The inven-tion relates to fatty acid monoglyceride polyglycol ether sulfosuccinates of the general formula (1) H~C-O-(CHR-CHs-O)~-R~
HC-O~CHR-CHs-O~ b -Rs ( 1 ) Hs~-O~CHR-CH2-O)c~Ra in which R is identical or different ~ or -C~3 - R1 is -CO-CH-CHz-COO-x- or -CO-CHs-CH-COO-~
loa - x- soa - x R2 is R' or ' .

2 ~ 7 R3 is an acyl radical having 8 - 22 C
atoms, preferably 12 - 18 C atom~, which is optionally substituted and~or contains mnltiple bcnds a, b and c can be identical or different O - 10, preferably O - 5, where a ~ b + c iq 21, prefersbly ~2, in particular in the range 5-- 15, and x~ is H' or a cation.
The invention further relates to a proce3~ for the preparation of compound~ of the general formula (1).
The invention additionally relates to aqueous hair cleaning and care compositions, washing-up liquids, skin-care composition~ and cleaning compositions, which are characterized in that they contain 1 - 10 parts by weight of at least one of the compounds of the general formula (1), defined amounts of at least one surfactant from the group ~on3isting o~ the nonionic, amphoteric, zwitterionic and ionic ~ur~actants, preferably 0.1 to 30 parts by weight, if appropriate 0.1 to 15 parts by weight of one of the customary agents from the group consisting of the additives and auxiliari2s, thickening agents, fragrances, preservative~, colorants, plant extracts and, if appropriate, water to 100.
Further subjects of the invention are charac-terized by the claims.
-- - A starting substance for the preparation of the compounds of the general formula (I) according to the invention i8 glycerol. Depending on the requirements of ~ .

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2i~i~.3`~7 _ 5 _ the final product, a highly purified quality or the commercially available product of technical purity can be employed here.
Glycerol can be esterified or transesterified in a fir~t step either with a fatty acid or a fatty acid ester or reacted with alkylene oxides to give the poly-oxyalkylene alcohols (J. Am. Oil Che. Soc., ~sic] 38, 517-520 (1961), US Patent 3,640,998).
The compound~ according to the invention have degree~ of alkoxylation with a, b and c of in each case O - 10, preferably O - S, where a+b+c can be 1 - 20, preferably 1 - 15. These values are to be considered as statistical mean values.
The fatty acids used are the monoba~ic acids having 8 - 22 C ato~ - preferably the naturally occur-ring acids - such a~ lauric acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, ricin-oleic acid, coconut fatty acid or mixture3 thereof (cf.
J. Am. Oil Chem. Soc. 38, 517-520 (1961) and ~P-A-O-l90 779).
The reaction to give the sulfo~uccinate i8 carried out using maleic anhydride and sub~equent sulfo-nation with ~odium ~ulfite according to proces~es known per se (German Offenlegung~schrift 2 700 072).
In this reaction, stirring i8 carried out at 60 - 80C using one mol of maleic anhydride per mol of hydroxyl group to be reacted until reaction of the anhydride i8 complete. The maleic acid hemie~ter i8 then added to an aqueous sodium sulfite ~olution (1 equivalent 2 ~ 3 7 of sulfite per equivalent ~f hemiester) and sulfonated at 60 - 80C until the sulfite has completely reacted. The aqueous product is then adjusted to neutral p~.
In general, the proces is carried out according to the invention such that in a first step the glycerol a:Lkoxylates are prepared by addition of alkylene oxides to glycerol in the presence of an alkaline catalyst at temperatures of 120 - 180C, that in the following second ~tep the glycerol alkoxylate fatty acid esters are prepared by esterification or transesterification with fatty acids or fatty acid ester~ re~pectively at 140 - 180C, if appropriate in the presence of a cata-lyst, and in a third step the hemie~ter i8 prepared by addition of maleic anhydride at 60 - 80C and this is reacted in a last step at 60 - 80C with aqueous sodium sulfite solution to give the salt of the corresponding sulfonic acid.
The compounds according to the invention are represented in idealized form by the general formula (I).
In addition to the monoesters indicated, the technical mixturefi still contain small amounts of the di- and pos~ibly triesters, and the degree~ of alkoxylation indicated are also statistical mean values.
Purification is not necessary for use according to the invention~ i.e. the technical mixtures can ~e directly further used as such.
The mixtures according to the invention for cleaning purpoees and cosmetics are in general present as aqueous composition~ or a~ aqueou~ alcoholic solutions, h~
~, _ 7 creams, emulsion or gels ànd can additionally contain the auxiliaries and additive3 customary in each case for adaptation to the intended application purpose, which are additlonally used for the preparation of cleaning agents and cosmetic preparations in the area of hair and body cleaning, i.e. are cu~tomary for shower baths, foam baths, shampoos, liquid soap~, baby care composition~ and detergents as well a~ for mild cleaning age-nts such as washing-up liguids for manual use, neutral cleaners and all-purpose cleaners.
A further advantage lie~ in the fact that if anionic and cationic compounds are simultaneously present in a recipe this displays both a cleaning and caring action.
Additionally, these recipes in the modern opinion approach a multilaterally utiliæable composition, since in addition to hair cleaning and ~imultaneous hair care they also have a cleaning and caring effect on the skin.
When the compounds according to the invention are addi-tionally used, they can thus fulfill the requirements in practice for body/hair-care shampoos without problems.
For the cosmetic applications, the surfactants, fragrances, pre~ervatives, colorants, plant extracts or other cosmetic additive~ cust~mary in these sectors can additionally be used.
Suitable surfactants in addition to the known betaines, amphoteric and nonionic compounds for ~the cleaning recipes are in particular the anionic surfactants ~uch as carboxylates, alkylsulfates, alkyl ~' ' .

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2~ 7 ether sulfates, alkylsulfonates, alkyl ether sulfonates and alkylsulfosuccinates. Preferred according to the invention are alkylamidobetaines such as REWOTERICR
1~ AM B 13 and AM B 14, carboxyglycinate~ such as REWOTERIC~ AM 2 C NM, carboxypropionates such as REWOTERIC~ AM KSF 40, sulfobetaines such as REWOTERICR AM CAS, anionic surfactants such as ether sulfates REWOPOLR 2~ NL 3, ether carboxylates such a3 REWOPOLR CLN 100, sulfo~uccinates such as REWOPOLR SB FA 30, REWOPOLR SBZ, REWODERM~ 3) SPS ~
nonionic surfactant such as glycerol fatty acid ester ethoxylates such as REWODERMR ES 90, glycerol mono-stearate such as REWOMULR ') MG, cetyl alcohol (O~ 2~ 3)~
') ~ trademarks of REWO Chemische Werke GmbH, Steinau an der Stra~e).
In addition to the compound~ accorting to the invention, which are employed in amounts of 1 - 10 parts by weight, in particular 2 - 8 parts by weight, in shampoo~, and 1 - 7 parts by weight, preferably 1 - S parts by weight, in creams, the other surfactants in the shampoos are customarily additionally used in amounts of 1 - 20 parts by weight, pre~erably 1 - 15 parts by weight, and in the cream~ in amounts of 1 - 10 parts ~y weight, preferably 2 - 5 parts by weight.
The thickeners employed are 1 - 8 parts by weight of the compounds cu~tomary in this sector such as glycerol fatty acid ester ethoxylates, ~atty~ alcohol ethoxylates, fatty acld alkylolamides and the customary alkali metal, alkaline ~arth metal and ammonium salts, :. ~

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' 2 ~ e i 7 g which are soluble in water at 20C in amounts of at least 1% by weight, such as, in particular, NaCl and NH~Cl.
The abbreviations used in the following examples have the following meaning:
AN = acid number ~N = hydrolysis number OHN = hydroxyl number B-D = Benzavlon These analytical values are determined ~y the following methods which are generally customary in this sector: -Acid number LAN ?
The acid number i8 a measure of the content of free acids of a fat or of technical fatty acids and indicates the milligrams of potassium hydroxide which are necessary in order to neutralize l gram of substance.
The values are determined by the DGF standard method C-V4.

Content of dry matter The content i8 determined by heating and drying at 105C to constant weight.

Hydroly~is Number IHN) The hydrolysi~ number i8 a measure of the free and bound acids contained in fats and technical fatty acids. It indicates the number of milligrams of potassium hydroxide whi~h is ~sic] necessary in order to hydrolyze ...

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:L gram of substance or technical fatty acids (mg of l~OH/g). The values are determined by the standard methods of the German Society for Fat Chemistry (DGF): DGF C-V3.

Elydroxyl number_LOHN~
The hydroxyl number is used to determine the content. of hydroxyl group5 and indicates the number of milligrams of potassium hydroxide which i8 r8ic] neces-sary in order to neutralize the acetic acid consume* by one gram of substance during the acetylation (mg of XOH/g3. The values are determined by the DGF ~tandard method DGF C-V17a.

Benzavlon deterSLent The content of detergent (B-D) indicated in the following examples i8 titrated by the customary two-phase titration with benzalkonium chloride again~t Methylene ~lue as an indicator (cf. S. R. Epton, Nature (London)~
160, 1967, page 795).

Preparation of the compounds according to_the invention Example 1 92 g (1 mol) of glycerol are treated with 0.5 g of potassium hydroxide and treated with 330 g (7.5 mol) of ethylene oxide at 140 - 170C with stirring, ~lacuna]
that the pressure in the reaction ve~sel does not exceed 4 bar. A pale liquid havinq a hydroxyl number (OHN) of 410 mg of ~OH/g re~ults.

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Example 2 410 g (1 mol) of the compound from Example 1 are t;reated with 207 g (1 mol) of coconut fatty acid (C~-Cl8) and heated to 180C. The water of reaction formed i~
continuously removed by distillation; if necessary the reaction i8 completed by applying a vacuum. A pale yellow liquid .having the following analytical numbers is obtained:
O~N 197 mg of K0~/g Hydrolysis number (HN) 91 mg of K0~/g Example 3 598 g (1 mol) of ester from Example 2 are treated with 98 g (1 mol) of maleic anhydride at 60 - 80C and stirred at this temperature for 2 h. The maleic acid hemiester i~ then added to a 60C solution of 560 g of water and 126 g (1 mol) of Na2S03 and stirred at 60 - 70C
until the S02 content of the solution is <0.01%. A clear, pale solution having the following analytical numbers i~
formed:

Solid~ content 62%
Benzavlon detergent (B-D) 31%

Example 4 299 g (0.5 mol) of ester from Bxample 2 are reacted with 98 g (1 mol) o~ ma1eic anhydride as described in Example 3 and the product i8 then sulfonated in 520 g of water and 126 g of Na2S03. A clear, pale 2 i ~

yellow liquid having the following analytical numbers i8 formed:

Solid~ content 48%
B-D 42%

~xample 5 460 g (5 mol) of glycerol are reacted with 0.9 g of potassium hydroxide and 550 g (12.5 mol) of ethylene oxide analogously to Example 1. The liquid product ha~ an OHN of 859 mg of KOH/g.

Exam2~e 6 392 g (2 mol) of ethoxylate from Example 5 are treated analogously to Example 2 with 417 g (2 mol) of coconut fatty acid (C~_C1B)-~ he pale yellow liquid has the following ana-lytical data:

- OHN 271 mg of RO~/g HN 146 mg of KO~/g Examp~e 7 414 g (1 mol) of the ester from Example 6 are reacted with 196 g (2 mol) of maleic anhydride analo-gously to Example 3 and then sulfonated in 886 g of water and 252 g of Na2SO3. The slightly turbid, pale yellow product has the following analytical data:

:' ' ;~ ' .. ' Solids content 49.9%

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Example 8 460 g ~5 mol) of glycerol are treated with 0.9 g of potassium hydroxide and reacted with 2,200 g (50 mol) of ethylene oxide analogously to Example 1. The product ha6 an O~N of 331 mg of KO~/g.

Example 9 508 g (1 mol) of the ethoxylate are esterified with 208 g (1 mol) of coconut fatty acid (C~-C1d) analogously to Example 2. ~he pale yellow ester has the following analytical numbers:

O~N 165 mg of XO~/g HN 79 mg of ROH/g Example 10 - 698 g (1 mol) of the ester from Example 9 are ~acted with 196 g (2 mol) of maleic anhydride analo-gously to Example 3 and then sulfonated in a solution of 1~150 g of water and 252 g (1 mol) of Na2SO3. A pale, liquid product having the following analytical numbers i8 formed: -Solid~ content 49.8%
B-D 44%

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Example 11 410 g (1 mol) of the ethoxylate from Example 1 are ~e~terified analogou~ly to Example 2 with 218 g (1 mol) of coconut fatty acid (C~2-Cl,3). The pale yellow, liquid product has the following analytical data.

OHN 183 mg of XOH/g Hydrolysis number (HN) 93 ~g of KOH/g .
Example 12 306 g (~.5 mol) of the compound from Example 11 are reacted with ~8 g (1 mol) of maleic anhydride and sulfonated in 542 g of water and 126 g (1 mol) of Na2SO3 analogously to Example 3. The pale yellow product has the following analytical data:

Solids content 49.6 B-D 40~

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The formulations below can be prepared by sLmply stirring the recipe constituent~ into water.
All recipe~ are given in percentage by weight calculated on solid.

Explanation of the surfactants employed by CTFA name~:
1 ~ disodium PEG-4 cocoamido MIPA-sulfosuccinate 2 3 disodiumlauroamphodiacetate tsic]
(and) sodium lauryl sulfate (and) hexylene glycol 3 - cocoamidopropyl hydroxysultaine

4 = ricinoleamidopropyltrimonium methosulfate

5 = PEG-200 qlyceryl tallowate mod.

6 - disodium laureth sulfosuccinate

7 = sodium laureth sulfate

8 3 cocoamidopropyl betaine

9 3 PEG-200 glyceryl tallowate

10 = disodiumcocoamphodiacetate [sic]

11 - PEG-80 glyceryl tallowate ~2 ~ cocoamidopropyl betaine 13 - glyceryl stearate 14 - laureth-6 , . .

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Analytical_methods:

Hardness compatibility: DIN 53 905 Skin compatibility (Zein test):
Gotte, Ern~t, Chem. Phys. Appl. Surface Active Subst.
Proc. Int. Congr. 4 (1964) 83-90:
c 200 mg of N/100 ml ~ non irritant 200-400 mg of N/100 ml 3 slightly irritant > 400 mg of N/100 ml - irritant Surface tension:
Dr. R. Hen~ch; Fats, Soaps, Coating~, 72 (1970), pp.

ELB: Determination according to W. C. Griffin ("Calculation of ~urface Active Agents by HLB", Journal Soc. Cosm. Chem. 1, 311 (1949)) vi8~:08ity:
~rookfield rotary viscometer (cup and spindle) measured at 20C according to the details of the apparatus manufacturer.
Determination of the ~oaming pow~r according to Ross Miles based on DIN 53902 Part 2 with the modifica-tion that the following measu~ements and amounts were used:

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Internal diameter of the outlet nozzle: 3.5 mm Hleight of fall of the sample solution: 940 mm Amount of the sample solutior. initially introduced: 50 ml Amount of the sample solution running in: 200 ml Measurement temperature: 40C
Solvent: demineral-~ized water asic recipe: Skin cleanina composition and make-up remover for sen~itive skin Compound according to the invention 2 - 8 parts by weight REWOTERICR* AM B 14 12) 2 - 8 Hydroxyethylcellulose 0.2 - 1.5 Demin. water to 100 .

Basic recipe: Skin cream Compound according to the invention 1 - 5 parts by weight Glycerol monostearate 2 - 10 Cetyl alcohol 1 - 4 "
Paraffin oil 3.5E ~~;---- 4 - 12 Glycerol 1 - 5 Demin. water to 100 " ' .
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Preservative as required Basic recipe: Washing-up liquid Compound according to the invention 1 - 5 parts by weight REWOPOLR *NL 3-28 ') 1 - 30 "
REWOTERICR AM CAS 3 ) 1 ~ 5 -~
REWOPOLR LA 6 ~4 ~ 1 ~ 10 N
Demin. water to 100 Basic recipe: Shower bath Compound according to the invention 2 - 8 parts by weight REWOTERICR AM G 30 2~ 5 - 15 "
REWOTERICR AM CAS 3) 2 ~ 6 "
REWOQUATR* RTM 50 ') 1 - 3 "
REWODERMR* Li 5 75 5) 1 - 4 "
Demin.- water to 100 Basic recipe: ~air shampoo Compound according to the invention 2 - 8 parts by weight REWOPOLR NL 3-28 ~) . 4 - lO "
REWOTERICR AM B 13 9) 2 ~ 8 n REWODERMR Li 420-70 9) 1 ~ 4 Demin. water to 100 ': :

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Basic recipe: aby shampoo C'ompound according to t:he invention 2 - 8 parts by weight REWOTERICR AM 2 C NM 1~) 2 - 8 "
REWOTERICR AM B 13 ~) 4 - 12 "
REWOPOL~ NL 3-28 " 2 - 10 "
RBWODERMR Li 48-50 1~ 1 - 4 . n Demin. water to 100 * c Trademarks of REWO Chemie Werke Gmb~, Steinau an der Stra~e , .

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~ Y~3~ 7 ~e~t recipe: Shower bath The examples according to the invention have been asse~sed in the test recipe by a test panel of .20 persons (female and male) with respect to - foaming power - feel of the skin - feel of the dried skin Skin compatibility: reduction of the Zein values in the recipe of Tabl3 4.

Table 3 Recipe 1 2 3 _ _ _ Example 4 _ 4 Example 3 _ _ 4 REWOPOLR SB Z I ) 4 _ REWOTERICR AM G 3 o2 ~ 10 . 5 10 . S 10 . 5 REWOTERICR AM (.~.S3 ) 3 3 3 REWOQUAq!R RTM 50 ~) 1 1 ~EWODE~MR Li S 7 5 5 ~ 2 . 3 2 . 3 2 . 3 Demin. water to lO0 to 100 to 100 pH, adjusted with citric acid 6.5 6. 5 6 . 5 , .... _ Vi~cosity [mPas] 3,000 4,000 3,000 Foam height tmml 195/185 205/195 200/195 -- . _ . __ Foaming power A) good good good Foam structure A~ fine bub- creamy; fine cr0amy, fine bles bubble~ bubble3 Feel of the ~kin, wet ~kin A) relatively ~mooth ~mwoth . smooth Feel of the ~kin, dry .
skin ~) relatively~mooth smooth . ~mooth .
~) 5 The assessment wa~ carried out by a graduated a~sessment ~ystem, the abovementioned assessment representing the arithmetic mean value.

-~ Foamlng power:
Determination of the amount of foam formed on rubbing between the moist hands (hand wa~hing) ..

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~ u~ . 7 Test recipe: Hair shampoo The examples according to the invention have been ,ass~ssed in the recipe by 10 test persons experienced in the use for - combability - volume of the hair and set of the hairstyle.

Table S
Recipe 1 2 3 Exa~ple 4 _ 3 Example 10 _ _ 3 REWOPOL~ NL 3-28 7) 8 6 6 REWOTER~CR AM B 13 B) 5 4 4 REWODERMR ~i 420-70 9) 2.1 2.1 2.1 DQmln. wat~r to 100 to 100 to 100 p~, adju~ted with citr~c acid 6.5 6.5 6.5 Combability 3 5-6 5-6 .
Volume of th~ hair Set of the hair~tyle 3-4 6 6 _ Vi~co~ity lmPa ~ ~3,000 -1,400 -1,400 Foaming power ~mm] 195/185 195J185 195~185 Assessment of the combability:
1 - 3: difficult to comb through, the hair offers con-- siderable resistance to the combing process 4 - 7: the hair can be combed through relatively well, the combing resi6tance i8 reduced, depending on the type of hair sufficient for a conditioning shampoo 8 - 10: reserved for the following aftertreatment by 80-called hair rinse compositions " ' ' . ,. "

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As~essment of the hair volume and of the set of the hairstyle ~ 3: the hair i~ dry or dull and lifeless, poor set of the hairstyle . ..
4 - 7: the hair i8 soft and full, with at the same time a good set of the hairstyle r a - lo: the hair is soft and straight, but too loose, as a result the set of the hairstyle is not good.

The assessment wa~ carried out according to a graduated points system, the abovementioned assessment representing the arithmetic mean value.

Test recipe: Baby shamPoo or hair and body shampoo for sensitive s~in Table 6 Recipe 1 2 3 Example 4 _ 3 _ Example 7 _ _ 3 REWOTERICR AM 2 C NM 10~ 3.5 3.5 3.5 REWOTERICR~ AM B 13 ~) 7 7 7 REWopoLR) NL 3-28 7) 7.5 4.5 4.5 ~E~ODERMR) Li 48-50 11) 3 3 3 Demin. water to 100 to 100 to 100 _ pH, adjusted with citric acid 6.5 6.5 6.5 Fo~ming power mm 1~5/185 200/190 200/190 ,,,,, ,_ ..
ze~n value~, mg of N/100 ml (skin compatibility) ~70 ~70 ~70 Foam structure coarse fine fine bubble~ bubbles bubbles ._ Feel of the skin, wet and somewhat smooth smooth dry skin rough soft ~oft Test recipe: Skin cleaning _composition and make-up remover for sensitive skin Table 7 Recipe l 2 3 -Example 3 _ _ 4 Example 4 _ 4 _ REWOPOLR SB FA 30 6 ) 4 _ _ REWOTERIC AM B 14 12) 4.5 4.5 4.5 ~ydroxyethylcellulose 0.5 0.5 0.5 Demin. water to lO0 to 100 to lO0 p~ , adjusted with citric 6.5 6.S 6.5 acid -__ . _ ____ - ... _ Zein value~ mg of N/100 ml (ski~ compatibility) about 170 50 ~ 50 , .~ .

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The use of the sùlfosuccinates according to the invention in the present recipe yields a very good skin-compatible cleaning composition, which is seen in the low Zei~ value in comparison to the standard sulfosuccinate REWOPOLR SB FA 30.

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Assessment of the properties on the skin by 10 test persons; more than 80% assessed the test recipes 3 and 4 as - .good to spread on the ~kin - readily absorbing into the skin - the skin becomes smooth and soft without being tacky or greasy.
The Comparison Recipe 1 is assessed to be the same, the Recipe 2 is unstable.

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Claims (10)

Patent claims

1. Fatty acid monoglyceride polyglycol ether sulfo-succinates of the general formula (1) (1) in which R is identical or different H or -CH, R1 is or R2 is R1 or H
R3 is an acyl radical having 8 - 22 C atoms which is optionally substituted and/or contains multiple bonds a, b and c can be identical or different 0 -10, where a + b + c is ?1, and x+ is H+ or a cation.

2 . Compounds of the general formula (1) according to claim 1, characterized in that R is H
R1 and R2 are or R3 is an acyl radical having 8 - 18 C atoms a+b+c is 2 - 15 and x+ is a cation.

3. Compounds of the general formula (1) according to claim 2, characterized in that a+b+c is 5 - 10, R3 is an acyl radical having 8 - 18 C atoms from the natural mixture of the coconut fatty acids.

4. Process for the preparation of the compounds of the general formula (1) (1) in which R is identical or different H or -CH.
R1 is or R2 is R1 or H
R3 is an acyl radical having 8 - 22 C atoms which is optionally substituted and/or contains multiple bonds a, b and c can be identical or different 0 -10, where a + b + c is ?1, and x+ is H+ or a cation, characterized in that in a first step the glycerol alkoxylates are prepared by addition of alkylene oxides to glycerol in the presence of an alkaline catalyst at temperatures of 120 - 180°C, in that in the following second step the glycerol alkoxylate fatty acid esters are prepared by esterification or transesterification with fatty acids or fatty acid esters respectively at 140 - 180°C, if appropriate in the presence of a cata-lyst, and in a third step the hemiester is prepared by addition of maleic anhydride at 60 - 80°C and this is reacted in a last step at 60 - 80°C with aqueous sodium sulfite solution to give the salt of the corresponding sulfonic acid.

5. Process according to claim 4, characterized in that in a first step the alkoxylates are prepared and in a second step the esters are prepared.

6. Aqueous hair cleaning compositions, containing a) 1 - 10 parts by weight of at least one of the com-pounds of the general formula (1) and b) 1 - 20 parts by weight of at least one surfactant from the group consisting of the nonionic ampho-teric, zwitterionic, ionic surfactants and if appropriate c) 0.1 - 10 parts by weight of thickeners, fragrances, preservatives, colorants, plant extracts and other additives and auxiliaries and d) water-to 100.

7. Aqueous shower shampoo, 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, ionic surfactant and c) 0.1 - 10 parts by weight of thickeners, fragrances, preservatives, colorants, plant extracts and other additives and auxiliaries and if appropriate d) water to 100.

8. Aqueous washing-up liquid, containing a) 1 - 10 parts by weight of at least one of the com-pounds of the general formula (1) and b) 1 - 30 parts by weight of at least one surfactant from the group consisting of the nonionic, empho-teric [sic], zwitterionic, ionic surfactants and if appropriate c) 0.1 - 10 parts by weight of thickeners, fragrances, preservatives, colorants, plant extracts and other additives and auxiliaries and if appropriate d) water to 100.

9. Skin cream, containing a) 1 - 10 parts by weight of at least one of the com-pounds of the general formula (1) and b) 1 - 10 parts by weight of at least one surfactant from the group consisting of the nonionic, ampho-teric, zwitterionic, ionic surfactants and if appropriate c) 2 - 10 parts by weight of plant or mineral oils, ester oils d) 1 - 5 parts by weight of consistency-imparting agents e) 0.5 - 5.0 parts by weight of fragrances, colorants, preservatives f) water to 100.

10. 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 consisting of the nonionic, ampho-teric, zwitterionic, ionic surfactants and if appropriate c) 0.1 - 10 parts by weight of thickeners, fragrances, preservatives, colorants, plant extracts and other additives and auxiliaries and if appropriate d) water to 100.