WO1999058105A1

WO1999058105A1 - Surface active agents for cosmetic formulations

Info

Publication number: WO1999058105A1
Application number: PCT/EP1999/002951
Authority: WO
Inventors: Rolf Kuratli
Original assignee: Ciba Specialty Chemicals Holding Inc.
Priority date: 1998-05-08
Filing date: 1999-04-30
Publication date: 1999-11-18
Also published as: JP2002514585A; AU4136799A; EP1075250A1

Abstract

A personal care formulation which is obtainable from the reaction of an ethylenically unsaturated sulfonic acid or carboxylic acid or anhydride thereof with a nonionic surfactant of the formula (1): R1-O-(alkylene-O)n1-R2, in which R1 is C8-C22alkyl or C8-C18alkenyl; R2 is hydrogen, C1-C4alkyl, a cycloaliphatic radical having at least 6 C atoms or benzyl; and n1 is a number from 1 to 60; and if appropriate with sugar derivatives, the preparation of these agents, their use in cosmetic formulations, and cosmetic formulations comprising the surface active agents.

Description

Surface Active Agents for Cosmetic Formulations

The present invention relates to multifunctional surface active agents, the preparation of these agents, their use in cosmetic formulations, and cosmetic formulations comprising the surface active agents.

Due to it's especially good foam forming ability, sodium lauryl sulphate is particularly useful for application in personal care compositions such as hand lotions, facial washing creams, shaving creams, shampoos, shampoo gels, shower creams, shower gels, foam bath liquids, miscible or soluble bath oils or liquid soaps. However, it is well known that sodium lauryl sulphate can lead to distinct irritation of the human skin.

Typically, such a shower gel has, for example, the following composition:

a) sodium lauryl sulphate (28%) 34-60 wt.% b) lauric acid amidopropyl betain (30%) 8-16 wt.% c) lauric acid monoglyceride (20%) 1-5 wt% d) lauryl alcohol ethoxylate 0.1-0.5 wt.% e) perfume oil 0.5-2 wt.% f) sodium chloride 2-10 wt.% g) preservative 0.05-0.5 wt.% h) water to 100

Surprisingly, it has now been found that reaction products of an ethylenically unsaturated sulfonic acid or carboxylic acid or anhydride thereof and certain nonionic surfactants and, if appropriate, sugar derivatives are surface active agents which are capable of replacing, completely or in part, component (a) mentioned in the above shower gel composition. The composition thus obtained exhibits the same good effects without the detrimental skin irritation.

The present invention therefore relates to a surface active agent which is obtainable from the reaction of, based on the total weight of the cosmetic formulation, 2.5 to 19.6 % by weight of an ethylenically unsaturated sulfonic acid or carboxylic acid or anhydride thereof, with 20 to 95 % by weight of a nonionic surfactant of the formula (1) R O-(alkylene-0)_n-R₂

in which

Ri is C₈-C₂₂alkyl or C₈-C₁₈alkenyl;

R₂ is hydrogen; C C₄alkyl; a cycloaliphatic radical having at least 6 C atoms or benzyl;

"alkylene" is an alkylene radical having 2 to 4 carbon atoms; and n_! is a number from 1 to 60; and with

0 to 60 % by weight of sugar derivatives.

Substituents Ri and R in the formula (1 ) are advantageously the hydrocarbon radical of an unsaturated or preferably saturated aliphatic monoalcohol having 8 to 22 carbon atoms. The hydrocarbon radical can be straight-chain or branched.

Preferably, R, and R₂ are an alkyl radical having 9 to 14 C atoms.

Aliphatic saturated monoalcohols are naturally occurring alcohols, for example lauryl alcohol, myristyl alcohol, cetyl alcohol or stearyl alcohol, and synthetic alcohols, for example 2- ethylhexanol, 1 ,1 ,3,3-tetramethylbutanol, octan-2-ol, isononyl alcohol, trimethylhexanol, trimethylnonyl alcohol, decanol, C₉-Cnθxo alcohol, tridecyl alcohol, isotridecyl alcohol or linear primary alcohols (Alfols) having 8 to 22 carbon atoms. Some representatives of these Alfols are Alfol (8-10), Alfol (9-11), Alfol (10-14), Alfol (12-13) or Alfol (16-18). ("Alfol" is a registered trademark.)

Unsaturated aliphatic monoalcohols are, for example, dodecenyl alcohol, hexadecenyl alcohol or oleyl alcohol.

The alcohol radicals can be present individually or in the form of mixtures of two or more components, for example mixtures of alkyl and/or alkenyl groups which are derived from soya fatty acids, palm kernel fatty acids or tallow oils.

(alkylene-O)-chains are preferably divalent radicals of the formulae CH₃ CH₃

-(CH₂-CH₂-0)-, -(CH-CH₂-0)-, or -(CH₂-CH-0)- .

Examples of a cycloaliphatic radical are cycloheptyl, cyclooctyl or, preferably, cyclohexyl.

Nonionic surfactants are preferably compounds of the formula

^γι ^γ2 _{3 4} i i i i

(2) R₃-0-(CH-CH-0)^-(CH-CH-0)-^R₄

in which

R₃ is C₈-C₂₂alkyl;

R₄ is hydrogen or C C alkyl;

Yι, Y₂. Y3 and Y_4> independently of one another are hydrogen, methyl or ethyl; n₂ is a number from 0 to 8; and n₃ is a number from 2 to 40.

Particulary preferred important nonionic surfactants are those of the formula (2) in which

R₃ is C₉-C₁₄alkyl;

R₄ is C C₄alkyl;

Y1. Y2- Y3 and Y₄, independently of one another are hydrogen, methyl or ethyl, where one of the radicals Y^ Y₂, Y₃ or Y₄ is always hydrogen; and n₂ and n₃, independently of one another are an integer from 4 to 8.

The nonionic surfactants of the formulae (1 ) and (2) can be employed as mixtures. Thus, for example, surfactant mixtures are fatty alcohol ethoxylates of the formula (1) which do not have closed end groups, i.e. compounds of the formula (1) in which

Ri is C₈-C₂₂alkyl,

R₂ is hydrogen and the alkylene-O-chain is the radical -(CH₂-CH₂-O)- and fatty alcohol ethoxylates of the formula (2) which have closed end groups.

Examples of the nonionic surfactants of the formulae (1) and (2) are reaction products of a C₁₀-Cι₃-fatty alcohol, for example a C₁₃oxo alcohol, with 3 to 10 mol of ethylene oxide, propylene oxide and/or butylene oxide, with a reaction product of 1 mol of a C₁₃-fatty alcohol with 6 mol of ethylene oxide and 1 mol of butylene oxide, it being possible in each case for the addition products to have end groups closed by CrC₄alkyl, preferably methyl or butyl.

The nonionic surfactants of the formula (1) are prepared in a manner known per se, for example by reaction of a fatty alcohol with alkylene oxides. The corresponding nonionic surfactants which have closed end groups are prepared by subsequent reaction of the resulting adduct with an alkyl halide R₂-Hal, R₄-Hal or R₆-Hal, preferably with C_rC₄alkyl chloride.

Both monocarboxylic acids and dicarboxylic acids and anhydrides thereof, as well as sulfonic acids which in each case contain an ethylenically unsaturated aliphatic radical and preferably not more than 7 carbon atoms, can be employed as ethylenically unsaturated monomeric sulfonic acids or carboxylic acids or anhydrides thereof, or their mixtures, which are suitable for reaction with the nonionic surfactants of the formulae (1 ) and (2). Monocarboxylic acids having 3 to 5 carbon atoms, for example acrylic acid, methacrylic acid, α-haloacrylic acid, 2- hydroxyethylacrylic acid, α-cyanoacrylic acid, crotonic acid and vinylacetic acid, or acrylamide, are preferred. Ethylenically unsaturated dicarboxylic acids are preferably fumaric acid, maleic acid or itaconic acid, and furthermore mesaconic acid, citraconic acid, gluconic acid and methylmalonic acid. Maleic anhydride may be mentioned in particular as an anhydride of these acids.

Monomeric sulfonic acids which are used for the reaction are, for example, vinylsulfonic acid or 2-acrylamido-2-methylpropanesulfonic acid.

Sugar derivatives are monosaccharides, disaccharides, trisaccharides or oligosaccharides. In the context of the present invention, monosaccharide is to be understood as meaning an aldopentose, aldohexose, aldotreose, ketopentose or ketohexose. The compounds mentioned can also be in the form of lactones, for example D(+)-gluconic acid δ-lactone.

Examples of an aldopentose are D-ribose, D-arabinose, D-xylose or D-lyose; examples of an aldohexose are D-allose, D-altrose, D-glucose, D-mannose, D-gulose, D-idose, D-galactose, D-talose, L-fucose or L-rhamnose; examples of a ketopentose are D-ribulose or D-xylulose; - 5 -

examples of a tetrose are D-erythrose or threose; and examples of a ketohexose are D-psicose, D-fructose, D-sorbose or D-tagatose.

Examples of a disaccharide are trehalose, maltose, isomaltose, cellobiose, gentiobiose, saccharose, lactose, chitobiose, N,N-diacetylchitobiose, palatinose or sucrose.

Example of a trisaccharide are raffinose, panose or maltotriose.

Examples of an oligosaccharide are maltotetraose, maltohexaose and chitoheptaose.

Particularly preferred sugar derivatives are enolizable saccharides, for example fructose or palatinose. Sugar acids, for example gluconic acids (D-gluconic acid and salts thereof), glucaric acids (mucic acid), and glucuronic acids (D-glucuronic acid and D-galacturonic acid) can also be used according to the invention.

The individual components are preferably employed in the following amounts for the reaction:

50 to 90 % by weight of one or more nonionic surfactants,

5 to 13 % by weight of an ethylenically unsaturated sulfonic acid or carboxylic acid or anhydride thereof,

0 to 30 %, in particular 1 to 15 % by weight of sugar derivatives and

1 to 60, in particular 1 to 20 % of water.

The surface active agent according to the invention preferably corresponds to the reaction product of 5 to 13 % by weight of acrylic acid or methacrylic acid and 50 and 90 % by weight of the nonionic surfactant of the formula (2) and 0 to 30 % by weight of gluconic acid.

The surface active agent according to the invention is prepared by reaction of the nonionic surfactant of the formula (1) with an ethylenically unsaturated sulfonic acid or carboxylic acid or anhydride thereof at temperatures from 30 to 100°C, preferably 80 to 95°C, using a catalyst. In particular, the ratio of nonionic surfactant or several nonionic surfactants to ethylenically unsaturated sulfonic acid or carboxylic acid or anhydride thereof is 8:1 to 1 :1 , in particular 6:1 to 3:1.

The reaction is advantageously carried out in an inert atmosphere, for example in the presence of nitrogen.

Organic initiators which form free radicals are preferably used as catalysts for this reaction. Suitable initiators for carrying out the free radical polymerization are, for example, symmetric aliphatic azo compounds, such as azo-bis-isobutyronitrile, azo-bis-2-methylvaleronitrile, 1 ,1 - azo-bis-1-cyclohexanenitrile and 2,2-azo-bis-isobutyric acid alkyl esters; symmetric diacyl peroxides, for example acetyl, propionyl or butyryl peroxide, benzoyi peroxide, bromo-, nitro-, methyl- or methoxy-substituted benzoyi peroxides and lauroyl peroxides; symmetric peroxydicarbonates, for example diethyl, diisopropyl, dicyclohexyl and dibenzyl peroxydicarbonate; tert-butyl peroctoate, tert-butyl perbenzoate or tert-butylphenyl peracetate, and peroxydicarbamates, such as tert-butyl N-(phenylperoxy)-carbamate or tert- butyl N-(2,3-dichloro- or 4-chlorophenyl-peroxy)-carbamate. Other suitable peroxides are: tert-butyl hydroperoxide, di-tert-butyl peroxide, cumene hydroperoxide, di-cumene peroxide and tert-butyl perpivalate. Another suitable compound is potassium persulfate, which is preferably employed for the preparation of the detergent base according to the invention.

The catalysts are as a rule employed in amounts of 0.01 to 1 % by weight, based on the starting substances.

In another preparation variant, the ethylenically unsaturated sulfonic acid or carboxylic acid is initially introduced into the reaction vessel in a high concentration in a first stage and the fatty alcohol ethoxylate and, if appropriate, the sugar derivative are then incorporated into the formulation.

After the reaction, the reaction product obtained is partly neutralized to a pH of 3 to 10, preferably 4 to 5, with an inorganic and/or organic base, for example sodium hydroxide solution, potassium hydroxide solution, magnesium hydroxide, ethanolamine or triethanolamine. Bases which are used are, for example, 1 to 8 % by weight inorganic or organic bases, for example sodium hydroxide, magnesium hydroxide, ethanolamine, triethanolamine, N,N,N,N-tetrakis(2-hydroxypropyl)-ethyleneamine or 1-amino-1- deoxysorbitol, or mixtures thereof. Water is added to 100 % by weight.

Further auxiliaries, for example hydrotropic agents, higher fatty alcohols and the like, can be incorporated after the reaction in order to improve the specific properties, for example flow properties, foam properties and the like.

The surface active agent is outstandingly suitable for the preparation of cosmetic formulations, for example hand lotions, facial washing creams, shaving creams, shampoos, shampoo gels, shower creams, shower gels, foam bath liquids, miscible or soluble bath oils or liquid soaps, by the customary processes. The invention furthermore relates to the use of the surface active agent according to the invention for the preparation of cosmetic formulations.

The invention also relates to a cosmetic formulation which is typically a liquid or cream and can be obtained by stirring together the various components thereof, at an elevated temperature if desired.

The invention also relates to a cosmetic preparation, comprising a surface active agent as defined in claim 1 with cosmetically tolerable carriers or auxiliaries.

Optionally, the surface active agent according to the invention may simultaneously replace not only of sodium lauryl sulphate, but also the nonionic surfactant and defoamer components. The use of only one component facilitates metering and leads to a simplification of the preparation process for the cosmetic formulations.

Another variability of the cosmetic formulation in respect of its properties can be achieved by using different nonionic surfactants of the formula (1) and (2) for the preparation of the surface active agent according to the invention. The sugar-acrylic acid polymers are known complexing agents of very good biological degradeability and therefore do not accumulate in effluents. - 8 -

The following examples serve to illustrate the invention.

A. Preparation of the surface active agents according to the invention

Example 1 :

555.7 g of deionized water,

119.9 g of adduct from one part of a C₁₃-oxo alcohol and 9 parts of EO and

75.70 g of adduct from one part of a C₁₃-oxo alcohol and 10 parts of EO are initially introduced into a 1 litre reaction vessel with a heating jacket at 20 - 30°C and are heated up to 90°C.

At an internal temperature of 90°C, 195.6 g of acrylic acid, in the course of 3 hours, and 1.2 g of potassium persulfate, dissolved in 29.0 g deionized water, in the course of 195 minutes, are simultaneously metered in.

When metering of the catalyst solution has ended, the mixture is subsequently stirred at 90°C for a further 30 minutes and then cooled to room temperature.

At an internal temperature of 70°C,

22.9 g of sodium hydroxide solution (30 %) are added and the mixture is stirred until a clear homogeneous solution is formed.

Example 2:

80.8 g of deionized water,

750.0 g of adduct from one part of a C^ -fatty alcohol and 4 parts of EO are initially introduced into a 1 litre reaction vessel with a heating jacket at 20 -

30°C and are heated up to 90°C.

At an internal temperature of 90°C, 125.0 g of acrylic acid, in the course of 3 hours, and 1.2 g of potassium persulfate, dissolved in 29.0 g of deionized water, in the course of 195 minutes, are simultaneously metered in.

At an internal temperature of 70°C, 14.0 g of sodium hydroxide solution (30 % strength) are added and the mixture is stirred until a clear, homogeneous solution is formed.

Example 3:

80.8 g of deioinized water.

450.0 g of adduct from one part of a C^-fatty alcohol and 4 parts of EO and

300.0 g of adduct from one part of a decyl alcohol and 3 parts of EO are initially introduced into a 1 litre reaction vessel with a heating jacket at 20 -

30°C and are heated up to 90°C.

At an internal temperature of 70°C, 14.0 g of sodium hydroxide solution (30 %) are added and the mixture is stirred until a clear, homogeneous solution is formed. - 10 -

Example 4:

80.8 g of deionized water,

520.0 g of adduct from one part of a C^-fatty alcohol and 3 parts of EO and

239.0 g of adduct from one part of a C^-fatty alcohol and 5 parts of EO are initially introduced into a 1 litre reaction vessel with a heating jacket at 20 - 30°C and are heated up to 90°C.

At an internal temperature of 70°C,

14.0 g of sodium hydroxide solution (30 %) are added and the mixture is stirred until a clear, homogeneous solution is formed.

Example 5:

157.5 g of deionized water,

208.0 g of adduct from one part of a C₁₃-oxoalcohol and 3 parts of EO,

208.0 g of adduct from one part of a C₁₃-oxoalcohol and 10 parts of EO and

208.0 g of adduct from one part of a decyl alcohol and 6 parts of EO/4 parts of PO are initially introduced into a 1 litre reaction vessel with a heating jacket at 20 -

30°C and are heated up to 90°C.

At an internal temperature of 90°C, 187.0 g of acrylic acid, in the course of 3 hours, and 1.5 g of potassium persulfate, dissolved in

30.0 g of deionized water, in the course of 195 minutes, are simultaneously metered in.

When metering of the catalyst solution has ended, the mixture is subsequently stirred at 90°C for a further 30 minutes and then cooled to room temperature. - 11 -

Example 6:

94.8 g of deionized water,

375.0 g of adduct from one part of a C^-fatty alcohol and 3 parts of EO and

375.0 g of adduct from one part of a C^-fatty alcohol and 5 parts of EO are initially introduced into a 1 litre reaction vessel with a heating jacket at 20 - 30°C and are heated up to 90°C.

At an internal temperature of 90°C, 125.0 g of acrylic acid, in the course of 3 hours, and 1.2 g of potassium persulfate, dissolved in

29.0 g of deionized water, in the course of 195 minutes, are simultaneously metered in.

Example 7:

154.0 g of deionized water,

375.0 g of adduct from one part of a C₁₃-oxo alcohol and 6 parts of EO,

156.0 g of adduct from one part of a decyl alcohol and 6 parts of EO/4 of PO and

78.0 g of sodium gluconate are initially introduced into a 1 litre reaction vessel with a heating jacket at 20 - 30°C and are heated up to 90°C.

At an internal temperature of 90°C, 195.0 g of acrylic acid, in the course of 3 hours, and 2.0 g of potassium persulfate, dissolved in

40.0 g of deionized water, in the course of 195 minutes, are simultaneously metered in.

When metering of the catalyst solution has ended, the mixture is subsequently stirred at 90°C for a further 30 minutes and then cooled to room temperature. - 12 -

Example 8:

66.0 g of deionized water,

375.0 g of adduct from one part of a C₁₃oxoalcohol and 6 parts of EO,

156.0 g of decyl alcohol-6EO/4PO and

78.0 g of sodium gluconate are initially introduced into a 1 litre reaction vessel with a heating jacket at 20 - 30°C and are heated up to 90°C

At an internal temperature of 90°C, 195.0 g of acrylic acid, in the course of 3 hours, and 4.8 g of potassium persulfate, dissolved in

125.0 g of deionized water, in the course of 195 minutes, are simultaneously metered in.

Example 9:

193.8 g of deionized water,

375.0 g of adduct from one part of a C₁₃oxo alcohol and 6 parts of EO,

156.0 g of adduct from one part of a decyl alcohol and 6 parts of EO/4PO and

50.0 g of D-gluconic acid lactone are initially introduced into a 1 litre reaction vessel with a heating jacket at 20 - 30°C and are heated up to 90°C.

At an internal temperature of 90°C, 195.0 g of acrylic acid, in the course of 3 hours, and 1.2 g of potassium persulfate, dissolved in 29.0 g of deionized water, in the course of 195 minutes, are simultaneously metered in.

When metering of the catalyst solution has ended, the mixture is subsequently stirred at 90°C for a further 30 minutes and then cooled to room temperature. - 13 -

Example 10:

417.00 g of adduct from one part of a C^-oxo alcohol and 3 parts of EO,

417.00 g of adduct from one part of a C^-oxo alcohol and 5 parts of EO and

10.00 g of adduct from one part of a C₁₃-oxo alcohol and 10 parts of EO are initially introduced into a 1 litre reaction vessel with a heating jacket at 20 - 30°C and are heated up to 90°C

At an internal temperature of 90°C, 105.0 g of acrylic acid, in the course of 3 hours, and 2.0 g of potassium persulfate, dissolved in

49.0 g of deionized water, in the course of 195 minutes, are simultaneously metered in.

Example 11 :

343.0 g of deionized water.

76.0 g of adduct from one part of a C₁₃-oxo alcohol and 9 parts of EO,

48.0 g of adduct from one part of a C₁₃-oxo alcohol and 10 parts of EO and

368.0 g of adduct from one part of a C_1Q-fatty alcohol and 6 parts of EO/1 of BuO-methyl ether are initially introduced into a 1 litre reaction vessel with a heating jacket at 20 - 30°C and are heated to 90°C.

At an internal temperature of 90°C, 124.0 g of acrylic acid, in the course of 3 hours, and 1.0 g of potassium persulfate, dissolved in 25.0 g of deionized water, in the course of 195 minutes, are simultaneously metered in.

At an internal temperature of about 70°C,

15.0 g of sodium hydroxide solution (30 % strength) are added and the mixture is cooled further.

The reaction products prepared in Examples 1 to 1 1 can be neutralized with sodium hydroxide solution, potassium hydroxide solution, organic amines (ethanolamine or triethanolamine), magnesium hydroxide and the like. It is possible to adjust the pH to between 3.0 and 10.0. - 14 -

The water contained in the reaction product is preferably removed, if necessary, in a falling film evaporator.

B. Preparation of a shower gel

Example 12:

Ingredients:

A: 10.0% Lanol 1688 (cetearyl octanoate)

3.0% Sepigel 305 (polyacrylamide)

1.0% Dimethicone

B: 8.0% Proteol VS 22 (sodium cocoyl hydrolized soy protein)

5.0% Oramix NS 10 (decyl glucoside)

1.0% Perfume

8.0% Amonyl 675 SB (cocamidopropyl hydroxysultaine) 40.0% Surface active agent obtainable from Examples 1 to 11

3.5% Acrysol 22 (acrylates/steareth-20 methacrylate copolymer)

0.3% Sepicide HB (phenoxyethanol)

0.2% Sepicide Cl (imidazolidinyl urea) to 100% water to pH 7 sodium hydroxide

The ingredients of the fatty phase A are mixed and the ingredients B added successively with constant stirring, resulting in a smooth, shiny ivory coloured emulsion with excellent stability.

Example 13

Similar results are obtained when the 40% of surface active agent obtainable from Examples 1 to 11 of Example 12 is replaced by a mixture containing 30% of this surface active agent and 10% sodium lauryl sulphate. - 15 -

C. Preparation of a shampoo

Example 14

Ingredients:

A: 1.0% Montanov 68 (cetearyl alcohol)

1.0% Tricetylammonium chloride

1.0% Dimethicone

B: 17.0% Water

C: 33.5% Surface active agent obtainable from Examples 1 to 11 0.5% Perfume

D: 11.0% Amonyl 380 BE (cocamidopropyl betaine) 0.08% Kathon CG (methylchloroisothiazolinone)

E: 0.3% Hydroxyethylcellulose 30.0% Water

F: 1.2% Acrysol 22 (acrylates/steareth-20 methacrylate copolymer) to 100.0% Water

to pH 7.2 Sodium hydroxide

Ingredients A are melted and emulsified in B with heating. To this emulsion, C is then added, the mixture being carefully homogenised, after which D is added. E and F are prepared separately and then added to the formulation, which is finally neutralised to give a white, opaque viscous gel with excellent stability.

- 16 -

Example 15

Ingredients:

8.9% Surface active agent obtainable from Examples 1 to 11

4.0% Montein LCQ (cocamidopropyl dimethylaminohydroxypropyl hydrolized collagen)

4.5% Proteol UCO (sodium/TEA undecylenoyi collagen amino acids)

1.5% Oramix L 30 (sodium lauryl sarcosinate)

6.0% Amonyl 675 SB (cocamidopropyl hydroxysultaine)

0.4% Perfume to 100.0% Water to pH 5 Lactic acid

The ingredients are mixed in the order indicated under rapid stirring, resulting in a clear liquid shampoo.

Claims

- 17 -What is claimed is:

1. A personal care formulation containing a surface active agent which is obtainable from the reaction of, based on the total weight of the personal care formulation,

2.5 to 19.6 % by weight of an ethylenically unsaturated sulfonic acid or carboxylic acid or anhydride thereof with

20 to 95 % by weight of a nonionic surfactant of the formula

C) R O-(alkylene-0)_n-R₂

in which

R_T is C₈-C₂₂alkyl or C₈-C₁₈alkenyl;

R₂ is hydrogen; d-C^alkyl; a cycloaliphatic radical having at least 6 C atoms or benzyl;

"alkylene" is an alkylene radical having 2 to 4 carbon atoms; and ni is a number from 1 to 60; and

0 to 60 % by weight of sugar derivatives.

2. A personal care formulation according to claim 1 , in which the (alkylene-O) chains in formula (1) are divalent radicals of the formulae

3 ^^3

-(CH₂-CH₂-0)-, _₍CH_CH₂-0). or -(CH₂-CH-0)-

3. A personal care formulation according to claim 1 , in which the nonionic surfactant has the formula

^╬│╬╣ ^╬│a Y_{3 4}

I I I I

(2) R₃-0-(CH-CH-0)-_s-fCH-CH-0)-^R₄

in which

R₃ is C₈-C₂₂ alkyl;

R₄ is hydrogen or C C₄alkyl;

Y╬╣, Y₂. Y₃ and Y₄, independently of one another are hydrogen, methyl or ethyl; n₂ is a number from 0 to 8; and n₃ is a number from 2 to 40. - 18 -

4. A personal care formulation according to claim 3, in which the nonionic surfactant has the formula (2) in which

R₃ is C₉-C₁₄alkyl;

R₄ is d-C₄alkyl;

Y╬╣, Y_2> Y₃ and Y₄, independently of one another are hydrogen, methyl or ethyl, where one of the radicals Y^ Y₂, Y₃ or Y₄is always hydrogen; and n₂ and n₃, independently of one another are an integer from 4 to 8.

5. A personal care formulation according to any one of claims 1 to 4, in which a monocarboxylic acid having 3 to 5 carbon atoms is used as the ethylenically unsaturated carboxylic acid.

6. A personal care formulation according to claim 5, in which methacrylic acid or acrylic acid is used as the monocarboxylic acid.

7. A personal care formulation according to any one of claims 1 to 6, in which an enolizable saccharide or sugar acid is used as the sugar derivative.

8. A personal care formulation according to claim 7, in which gluconic acid is used as the sugar derivative.

9. A personal care formulation according to any one of claims 1 to 8, which is obtainable from

50 to 90 % by weight of one or more nonionic surfactants,

5 to 13 % by weight of an ethylenicallly unsaturated sulfonic acid or carboxylic acid or anhydride thereof,

0 to 30 % by weight of sugar derivatives and

1 to 60 %of water.

10. A care formulation according to claim 9, which is obtainable from 50 to 90 % by weight of one or more nonionic surfactants, - 19 -

1 to 15 % by weight of sugar derivatives and

1 to 20 %of water.

11. A personal care formulation according to any one of claims 1 to 10, which is obtainable from 5 to 13 % by weight of acrylic acid or methacrylic acid and 50 to 90 % by weight of the nonionic surfactant of the formula (2) and 0 to 30 % by weight of gluconic acid.

12. A personal care formulation according to any one of claims 1 to 11 , wherein the reaction is carried out in the presence of a catalyst and at a temperature of 30 to 100┬░C.

13. A personal care formulation according to claim 12, in which potassium persulfate is used as the catalyst.

14. A personal care formulation according to any one of claims 1 to 13 which is a hand lotion, facial washing cream, shaving cream, shampoo, shampoo gel, shower cream, shower gel, foam bath liquid, miscible or soluble bath oil or liquid soap.

15. A cosmetic preparation, comprising a surface active agent as defined in claim 1 with cosmetically tolerable carriers or auxiliaries.