FR2735384A1 - SURFACTORY COMPOSITION BASED ON POLYACOXYLATED AMIDOAMINES - Google Patents

Abstract

A surfactant composition containing a mixture of polyalkoxylated amidoamines having average formulae (1) and (2), wherein each R<1> is independently a C2-22 hydrocarbon group, straight or branched alkyl or alkenyl, cycloalkyl or alkylaryl, each R<2> is independently hydrogen or a C1-4 alkyl radical, and p, q, r, s and t, which are the same or different, are integers or fractional numbers from 1 to 50, particularly 1.1 to 25 and preferably 2 to 20. The composition may be used as a detergent, particularly in cosmetics, and is preferably used in combination with at least one anionic surfactant in order to reduce its skin and eye irritancy.

Description

SURFACTORY COMPOSITION BASED ON POLYALCOXYLATED AMIDOAMINES
The present invention relates to surfactant compositions based on polyalkoxylated amidoamines. It also relates to their use, preferably in combination with at least one surfactant of anionic type in surfactant compositions which are of interest in particular for applications in detergents and in cosmetics.

formules dans lesquelles: -R1, identiques ou différents, représentent un groupe hydrocarboné en C2-C22 alkyle ou alkényle linéaire ou ramifié, cycloalkyle ou alkylaryle, - R2, identiques ou différents, représentent l'hydrogène ou un radical alkyle en C1-C4, - p, q, r, s et t, identiques ou différents, représentent des nombres entiers ou fractionnaires, compris entre 1 et 50, plus particulièrement compris entre 1,1 et 25, et de préférence compris entre 2 et 20, ledit mélange comportant respectivement de 99,9 à 0,1 % en poids de produit de formule (1) pour 0,1 à 99,9 % en poids de produit de formule (2).A subject of the present invention is therefore a mixture of polyalkoxylated amidoamines of medium formulas (I) and (2):

formulas in which: -R1, identical or different, represent a hydrocarbon group in C2-C22 alkyl or alkenyl linear or branched, cycloalkyl or alkylaryl, - R2, identical or different, represent hydrogen or a C1-C4 alkyl radical, - p, q, r, s and t, which are identical or different, represent whole or fractional numbers, between 1 and 50, more particularly between 1.1 and 25, and preferably between 2 and 20, said mixture comprising respectively from 99.9 to 0.1% by weight of product of formula (1) for 0.1 to 99.9% by weight of product of formula (2).

The mixtures of polyalkoxylated amidoamines forming the subject of the invention have the advantage of being surfactants very well tolerated by biological systems and generally have good foaming, dispersing and detergent powers, which makes their field of application. very varied application.

In addition, it has been discovered that the mixture of polyalkoxylated amidoamines according to the invention, combined with the anionic surfactants usually used in cleaning formulations, makes it possible to significantly reduce the irritant potential of such formulations. Such effects are observed in particular in cosmetic cleaning formulations, such as shampoos, shower gels, bubble baths, liquid soaps, in household cleaning formulations such as liquids for hand washing dishes, cleaning textiles, floors or more metals.

However, other characteristics and advantages of the present invention will emerge more clearly on reading the description and the examples which follow.

The present invention therefore relates to a surfactant composition comprising a mixture of polyalkoxylated amidoamines of formulas (1) and (2) defined above.

According to a preferred variant of the present invention, the radical R2 represents hydrogen or a methyl radical.

A particularly advantageous variant of the invention consists of compositions having an amidoamide content of formula (1) of between 70 and 99% by total weight of the composition. Preferably, the content of amidoamines of formula (1) is between 95 and 99% relative to the total weight of the composition.

formules dans lesquelles R1 a la définition donnée ci-dessus.These polyalkoxylated amidoamines of formulas (1) and (2) can be prepared for example by polycondensation of alkylene oxide on a mixture of amidoamines of formulas (3) and (4):
R1- CO - NH- (CH2) 2-NH- (CH2) 2-OH (3)

formulas in which R1 has the definition given above.

This operation can be carried out at a temperature of the order of 70 to 1800C, preferably of the order of 110 to 150 "C, by continuously adding the activated derivative of alkylene glycol in a proportion of the order from 1 to 50 molar equivalents of alkylene oxide relative to the amidoamines of formulas (3) and (4), more particularly of the order of 1.1 to 25 molar equivalents. Preferably, this proportion is of the order of 2 to 20 molar equivalents Such a process is for example described in the patent
US -A 2,681,354.

This operation can also be carried out in the presence of a third solvent. By way of example of a solvent, mention may be made of saturated aliphatic hydrocarbons, such as heptane or octane, aromatic hydrocarbons, such as toluene, cumene, ketones such as in particular 2-octanone, secondary alcohols. or tertiary, such as isopropanol, tertiobutanol, and water.

The reaction can be carried out in the absence of a catalyst, or if necessary in the presence of a catalyst. This catalyst can be acidic, preferably of the Lewis acid type, such as, for example, boron trifluoride, tin tetrachloride or antimony pentachloride. It is also possible to use a basic catalyst chosen in particular from alkali metal hydroxides, such as NaOH, KOH, alkali metal or alkaline earth metal alcoholates, such as sodium methoxide or else potassium tert-butoxide. Likewise, as suitable catalysts, mention may be made of rare earth derivatives, such as in particular phosphates, carbonates and lanthanum oxides.

If a catalyst is employed, the amounts used correspond to about 0.05 to 10%, preferably about 0.1 to 1% by weight based on the reaction mass.

Another mode of preparation of said polyalkoxylated amidoamines of formulas (1) and (2) consists in reacting a polyalkylene oxide monohalohydrin, such as monochlorohydrins-1, 2 or monobromhydrins-1, 2 of polyethylene oxide, exhibiting a average degree of polycondensation from 1 to 50, more particularly from 1.1 to 25 and preferably from 2 to 20, on the mixture of amidoamines of formulas (3) and (4) above.

Polyalkylene oxide monochlorohydrins-1,2 are the preferred raw materials.

This operation can be carried out at a temperature of the order of 70 to 1800C, preferably of the order of 110 to 150 "C, by continuous addition of the monohalohydrin in a proportion of the order of 1 to 50 equivalents. molars of activated alkylene glycol derivative relative to the mixture of amidoamines of formulas (3) and (4), more particularly of the order of 1.1 to 25 molar equivalents, and preferably of the order of 2 to 20 molar equivalents.

This reaction can optionally be carried out in the presence of a third solvent. By way of example of a solvent, mention may be made, inter alia, of saturated aliphatic hydrocarbons, such as heptane, octane, aromatic hydrocarbons, such as toluene, cumene, ketones, such as 2-octanone. , secondary or tertiary alcohols, such as isopropanol, tertiobutanol, and water.

It may be necessary to neutralize the halogen formed continuously, using a base chosen for example from alkali metal or alkaline earth hydroxides, tertiary amines such as triethylamine. If desired, the halides formed can be separated from the medium by any known method, such as in particular precipitation with a third solvent of the alcohol type such as isopropyl alcohol, or else electrodialysis.

The amidoamines of general formulas (3) and (4) can be prepared by any means known to those skilled in the art. Thus, by way of example, one can carry out a hydrolysis of an imidazoline of general formula (5):

The hydrolysis consists in reacting the compound (5) with water, in the presence or absence of a catalyst. In such a case, the catalyst can be of the basic or acidic type within the meaning of Bronstead.

Among the basic catalysts, mention may be made of alkali metal or alkaline earth metal hydroxides, such as the hydroxides of Na, K, Ca, Mg, for example. It is also possible to use, as catalyst, salts of linear or branched carboxylic acids containing from 1 to 18 carbon atoms1, such as in particular acetate, formate, benzoate, Na or K. Amines, substituted or not. , such as for example NH3, N (C2H5) 31 N (CH2CH20H) 3, (HOCH2CH2) 2-N-CH2CH2-N (CH2CH2) 20H, are suitable for carrying out the reaction.

Among the acid catalysts, mention may be made of any mineral or organic acid whose pKa is less than 4. More particularly, it is recommended to use formic, lactic, citric and hydrochloric acids.

The hydrolysis reaction can optionally be carried out in the presence of an organic third solvent such as alcohols, ketones, ethers, saturated or aromatic hydrocarbons. Preferably, the solvent is chosen from alcohols. Thus, methanol, ethanol, propanol or else isopropanol are particularly suitable for carrying out this reaction.

The amounts of water used in the reaction can vary from 1 to 1000 molar equivalents with respect to the compound (5). More particularly, they are of the order of 1 to 200 molar equivalents relative to the compound (5) and preferably of 1 to 50.

The amount of basic catalyst, if it is used, is more particularly between 0.1 and 20 mol% relative to the compound (5) and preferably between 1 and 5 mol% relative to the same reference.

In the case where an acid catalyst is used, it is used in amounts more particularly between 1 and 100 mol% relative to the compound (5) and preferably between 5 and 96 molar relative to the same reference. .

The reaction can be carried out at atmospheric pressure or under autogenous pressure at temperatures between 20 and 200 "C, more particularly between 60 to 140" C, preferably between 80 to 120 ° C.

The ratios between the two amidoamines of formulas (3) and (4) can be adjusted according to the hydrolysis conditions. Thus, the production of the amidoamine of formula (4) is promoted by carrying out the reaction with a small amount of water, or a small amount of base, or even a low temperature. On the other hand, the reverse conditions favor the formation of the amidoamine of formula (3).

If one wishes to further enrich in amidoamine (3), one can proceed to a heat treatment which favors the rearrangement (4) in (3). This treatment consists in subjecting the mixture to a temperature between 60 and 120 ° C., more particularly at a temperature between 80 and 100 ° C., for a period of 2 to 10 hours.

The imidazolines of general formula (5) are prepared from the reaction of a derivative of a fatty acid (acid, ester, acid chloride) and aminoethyl ethanolamine according to conditions known to those skilled in the art. 'art.

As has been indicated previously, the mixtures of polyalkoxylated amidoamines which are the subject of the invention are surfactants very well tolerated by biological systems, and have good foaming, dispersing and detergent powers. In addition, it has been discovered that this mixture, when it is combined with the anionic surfactants generally used in cleaning formulations, makes it possible to significantly reduce the irritant potential of the latter.

The content of the mixture of polyalkoxylated amidoamines according to the invention, relative to the anionic surfactants, can vary over a wide range. However, it is recommended to use 1 part of mixture of polyalkoxylated amidoamines per 0.1 to 100 parts, and more particularly from 1 to 20 parts, of anionic surfactants.

The anionic surfactants which can be used are more particularly the water-soluble salts of alkylsulphates, of alkylsulphonates, of alkylarylsulphonates, of alkylarylsulphonates, of alkylethersulphates, alkylisethionates and alkyltaurates or their salts, alkylcarboxylates, alkylether alkylcarboxylates, alkylsulfosuccinates or alkylsuccinamates, alkylsarcosinates, salicylated derivatives of protein hydrolysates, acylaspartates.

A subject of the present invention is also the cosmetic compositions based on the polyalkoxylated amidoamines which are the subject of the invention.

The term cosmetic composition or formulation is understood to mean all cosmetic products or preparations such as those described in "Illustrative list by category of cosmetic products", of European directive no. 7617681CEE of July 27, 1976, known as "cosmetic directive".

The polyalkoxylated amidoamines, which are the subject of this invention, can be used more particularly in formulations of lotions, cleansing milks, make-up removing compositions, care creams, creams or lotions for protection against the sun and ultraviolet radiation, foams, etc. styling gels or any formulation used for styling or to facilitate combing the hair, hair or body shampoos, facial or body cleansing gels, liquid soaps, foaming bath compositions, formulations used for cleaning teeth or oral cavity, such as mouthwashes or toothpaste. Said polyalkoxylated amidoamines can also be used alone or in combination in the formulation of soaps or toilet bars. Due to their cationic activity at acid pH, they can also be used for the preparation of rinsing formulations or conditioning balms for hair or skin.

Cosmetic compositions in general generally contain surfactants which serve to disperse, emulsify, solubilize and stabilize various compounds used for their emollient or humectant properties. These surfactants are used in these compositions at concentrations varying from 0.05 to 10% by weight of the preparation.

Among the humectants, there may be mentioned, without intending to be limited, glycerol, sorbitol, urea, collagen, gelatin, aloe vera, hyaluronic acid.

The emollients are generally chosen from alkylmonoglycerides, alkyldiglycerides, triglycerides such as oils extracted from plants and vegetables (palm, copra, cottonseed, soybean, sunflower, olive and grape seed oils , sesame, peanut, castor, etc.) or oils of animal origin (tallow, fish oils, etc.), derivatives of these oils such as hydrogenated oils, lanolin derivatives, mineral oils or paraffinic oils, perhydrosqualane, squalene, diols such as 1-2-propanediol, 1-3-butanediol,
Cetyl alcohol, Stearyl alcohol, Oleic alcohol, polyethylene glycols or polypropylene glycols, fatty esters such as isopropyl palmitate, ethyl2-hexyl cocoate, myristyl myristate, lactic acid esters, Stearic acid, Behenic acid, Isostearic acid, silicone oils grouping together cyclic polydimethylsiloxanes, ao hydroxylated polydimethylsiloxanes, ao trimethylsilyllated polydimethylsiloxanes, polyorganosiloxanes such as polyalkylmethylsiloxylsiloxanes, polymethylsiloxanes, polydimethylsiloxanes , silicone waxes, silicone copolyethers (such as the SILBIONE 70646 oil marketed by the company RHONE-POULENC or DC 1908 marketed by DOW CORNING) or mixed silicone derivatives such as mixed polyalkylmethylsiloxane-silicone copolymer copolyethers.

To these compounds, powders or mineral particles can be added. By way of example of such compounds, mention may be made of calcium carbonate, inorganic oxides in powder form or in colloidal form, that is to say particles of smaller size or of the order of one micrometer, sometimes of a few tens of nanometers, such as titanium dioxide, silica, aluminum salts, generally used as antiperspirants, kaolin, talc, clays and their derivatives.

Preservatives such as methyl, ethyl, propyl and butyl esters of p-hydroxybenzoic acid, sodium benzoate, GERMABENB or any chemical agent preventing bacterial proliferation or mold and traditionally used in cosmetic compositions, can also be used. used. In general, they are introduced into these compositions in an amount of 0.01 to 3% by weight.

As an alternative to these chemical agents, it is sometimes possible to use agents which modify the activity of water and greatly increase the osmotic pressure, such as carbohydrates or salts.

To protect the skin or the hair from the aggressions of the sun and UV rays, we can add to these formulations sun filters which are either chemical compounds which strongly absorb UV radiation such as the compounds authorized in European directive N "76/768. / EEC, its annexes and subsequent amendments to this directive, either titanium dioxide or cerium oxides in the form of powder or colloidal particles.

Perfumes, dyes or pigments can also be added.

There may also be viscosifying or gelling polymers, such as in particular the crosslinked polyacrylates CARBOPOL) marketed by GOODRICH, cellulose derivatives such as hydroxypropylcellulose, carboxymethylcellulose, guars and their derivatives, carob, tara or gum. cassia, xanthan gum, alginates, carrageenans, chitin derivatives such as chitosan.

In the particular case of dentifrices, the formulations comprise the composition according to the invention in an amount representing 0.1 to 5% by total weight of the formulation. The composition according to the invention can be used alone or as a mixture with the usual surfactants for this type of formulations, such as anionic, nonionic or zwitterionic surfactants, such as alkylbétaines or alkylamidopropylbétaines, or amphoterics, or even combinations of these. compounds. These surfactants which are used as foaming agents during the use of the formulation, as well as for their cleaning power, disinfectant. Sometimes, they are used specifically for a "therapeutic" action like the alkyl sarcosinates which protect the teeth by inhibiting the enzymatic activity of bacteria responsible for infections of the teeth or gums.

The formulations for dentifrices further comprise abrasive agents, such as silica or calcium carbonate, in a content of between 5 and 25% by total weight of the formulation.

The dentifrice compositions can also comprise from 5 to 85% of so-called humectants such as glycerol, sorbitol, polyethylene glycols, lactilol, xylitol.

The rheological behavior of the dental paste, that is to say its viscosity, its hold on the brush, the ease of its extrusion at the outlet of the tube or the dispenser, the non-stringing character of the paste, is controlled by thickening agents such as certain silica used for this purpose (TIXOSIL 4349 marketed by RHONE
POULENC) and / or polymers used alone or in combination such as xanthan gum, guar gum, cellulose derivatives, for example carboxymethylcellulose, crosslinked polyacrylates such as CARBOPOL) distributed by
GOODRICH, alginates or carrageenans, VISCARIN). The total of the thickening agents usually represents 0.1 to 15% by weight of the composition of a dentifrice.

Therapeutic agents such as certain fluorine or potassium salts, flavors, sweetening agents and water are also generally found associated with these various constituents.

The polyalkoxylated amidoamines of this invention can also be used in toilet bar formulations, referred to as bar soaps or soaps.

Conventional toilet bar compositions generally comprise fatty acid salts used in combination with surfactants of the invention and optionally surfactants other than the salts of fatty acids or the fatty acids themselves. These compositions may likewise be based on these other surfactants, such as, for example, sodium C 8 -C 22 alkylisethionates or sodium C 8 -C 22 alkyl sulphates.

To these compositions, it is also possible to add various constituents useful for reducing irritation or aggression on the skin, such as alkali metal salts or isethionates, or for promoting hydration of the skin, such as certain carbohydrates, of the skin type. glycerol or sorbitol for example, polyethylene glycol or polypropylene glycol, alkoxylated derivatives of sugars or their derivatives (methyl glucose for example), water-soluble or water-dispersible polymers such as collagen or certain non-allergenic derivatives of animal or plant proteins (hydrolysates wheat proteins for example), natural hydrocolloids (guar gum, locust bean, tara ...) or resulting from fermentation processes such as xanthan gum and derivatives of these polycarbohydrates such as modified celluloses (for example hydroxyethylcellulose, carboxymethylcellulose, cationic celluloses such as POLYMER JAR%) sold by the company UNION CARBIDE), derivatives of guar or carob as their cationic derivatives (JAGUAR C1 3S),
JAGUAR Cl 62 sold by RHONE-POULENC) or nonionic derivatives (for example hydroxypropylguar), anionic derivatives (carboxymethylguar) or mixed nonionic / anionic derivatives such as carboxy-hydroxypropyl-guars or nonionic / cationic. Synthetic polymers such as polyacrylates or synthetic cationic polymers known under the generic CTFA name of “Polyquatemium”, for example the polymers MIRAPOL Au 56 or MIRAPOL 550 from the company RHONE-POULENC, can also be added alternately or in combination.

Metal sequestering agents, more particularly calcium sequestering agents such as citrate ions, or emollient agents, such as silicones or oils or fatty substances used for this purpose in the cosmetics industry (oils minerals, fatty acid esters, triglycerides, silicones in particular).

To these ingredients are generally added one or more perfumes, dyes and / or opacifying agents such as pigments such as titanium oxide particles.

Bactericidal or fungicidal agents can also be incorporated into the composition in order to improve the disinfection of the skin.

In a toilet bar whose formulation consists mainly of monocarboxylic fatty acid soaps (sodium, potassium, mono-, di- or triethanolamine salts); the fatty acid soap contents are generally more than 25% by weight of the formulation, generally from 30 to 95% by weight.

In a toilet bar whose formulation is based on other main constituents than fatty acid soaps, such as in particular Cg-C22 alkyl or alkenyl isethionates, as well as alkylsulphates, alkylethersulphates, alkylbetaines, alkylamidopropylbetaines, the alkylampho-acetates, -diacetates, propionates or -dipropionates used to reduce the irritation which may be caused by other surfactants, mainly anionic surfactants, the amount of these constituents can be up to 60%, or even 95%.

It should be noted that for this type of composition, the formulation contains from 0 to 50% by weight, preferably from 1 to 40% by weight of fatty acid soaps.

1 to 15% of Cg-C22 free fatty acids can also be introduced into all soap compositions, as superfatting agents or to modify the appearance and creaminess of the foam during washing.

Waxes such as paraffin waxes, natural waxes such as beeswax or ozokerite or silicone waxes can also be found in these compositions. These waxes are advantageously used to improve the appearance, the hold, the processability and the storage life of toilet bars.

In the case of formulations for shampoos, and more generally detergent compositions for personal use, the compositions may comprise, in addition to the amidoamines of the invention, the usual additives present in these types of formulation.

Mention may in particular be made of: anionic surfactants, such as water-soluble salts of alkylsulphates, of alkylethersulphates, alkylisethionates and alkyltaurates or their salts, alkylcarboxylates, alkylsulphosuccinates or alkylsuccinamates, alkylsarcosinates, alkylated derivatives of protein hydrolysates, acylaspartates, alkyl and or alkyl ether and or alkylaryl ether phosphate esters; the cation being an alkali metal or alkaline earth metal (sodium, potassium, lithium, magnesium), a substituted or unsubstituted ammonium residue (methyl-, dimethyl-, trimethyl-, tetramethylammonium, dimethylpiperidinium ...) or derivative of an alkanolamine (monoethanolamine, diethanolamine, triethanolamine ...) ;; - zwitterionic or amphoteric surfactants, such as alkylbétaines, alkyldimethylbétaines, alkylamidopropylbétaines, alkylamidopropyldimethyl betaines, alkyltrimethylsulfobetaines, imidazoline derivatives such as alkylamphoacetates, alkylamphoacetines, alkylamphultionphidropaidropamidates or alkylamphultionphultionphidropamidropamidates, alkyls, alkylspropionphidopaïroamidylates or else the condensation products of fatty acids and protein hydrolysates; - nonionic surfactants, such as polyoxyethylenated derivatives of Cg-C22 aliphatic or arylaliphatic alcohols, alkylpolysaccharides having a C6-C30 hydrophobic group, preferably C10-C16 and a polysaccharide group, for example polyglycoside, such as hydrophilic group as well as from 1 to 3 sugar units, alkylated derivatives of amino sugars, such as alkylglucamides produced by the amidification reaction of a fatty acid with N-methylglucamine; - Amides derived from fatty acids generally used for their ability to improve the foaming of the compositions or to increase the viscosity of said compositions; - cationic conditioning agents, improving the combability, styling, feel and volume of the hair, such as synthetic cationic polymers of the type MIRAPOL A154N) or MIRAPOL 550qu marketed by RHONE-POULENC, natural cationic polymers such as cationic derivatives guar (JAGUAR Cl 35 *, JAGUAR Cl 62 * sold by RHONE-POULENC) or cationic cellulose derivatives (POLYMER Je400 * sold by UNION CARBIDE); - conditioning or shine agents such as organopolysiloxanes, used as such or in solution in one of their usual solvents (silicone oils of low masses, highly branched paraffinic oils, fatty esters, for example of the isopropyl palmitate type, etc. ); - anti-dandruff agents, such as pyridinethiones, more especially zinc pyridinethione, compounds based on selenium such as selenium sulphide or OCTOPYROX *, marketed by HOECHST; - antiparasitic agents (anti-lice), such as LINDANE or various pyrethrins used for this purpose.

These compositions can also contain agents modifying the appearance or the viscosity of the formulations such as pearlscent compounds based on polyethylene glycol stearate or polymers improving the viscosity or stability such as the CARBOPOL * marketed by GOODRICH, hydrocolloids and their derivatives such as guar or modified guars, carob, xanthan gum, cellulose derivatives (hydroxyethylcellulose, carboxymethylcellulose).

The compositions can also contain electrolytes, as compounds making it possible to adjust the viscosity of the latter, such as sodium chloride or else ammonium chloride.

The conventional compositions of shampoos, shower gels, cleansing gels and bubble baths, containing the amidoamines of the invention, can consist of (percentages by weight):
mixture of amidoamines of the invention 1 - 15%
0 - 15% anionic surfactant
amphoteric surfactant 0 - 10%
0 - 5% fatty acid alkanolamide
thickening agent 0 - 5%
conditioning agent o - 3%
fragrance 0-2%
preservative 0-2%
anti-dandruff agent 0 - 2% electrolyte 0-6%
100% supplement water
A subject of the present invention is also the detergent compositions based on the polyalkoxylated amidoamines forming the subject of the invention, said polyalkoxylated amidoamines possibly being present in an amount, for example, of approximately 1 to 80% of the weight of said compositions, and of preferably about 1 to 40%.

The term “detergent composition” is understood to mean any detergent formulation, powder or liquid, intended for use both in a washing machine, in a dishwasher and for household cleaning in general.

In combination with said polyalkoxylated amidoamines of the invention, other additives of the type of those described below may be present in the detergent compositions.

- SURFACTANTS other, in amounts corresponding to approximately 1 - 50% by weight relative to the detergent composition, such as: anionic surfactants
salts of saturated or unsaturated Cg-C24 fatty acids, preferably Cg-C20 alkylbenzenesulphonates, primary or secondary C8- alkyl sulphonates
C22, alkylglycerol sulphonates, sulphonated polycarboxylic acids described in GB-A-1 082 179, paraffin sulphonates, N-acyl N-aikyltaurates, phosphate esters of alkyl and / or alkyl ether and / or of alkylaryl ether, isethionates, alkylsuccinamates, alkylsulfosuccinates, monoesters or diesters of sulfosuccinates, N-acyl sarcosinates, alkylglycoside sulfates, alkyl polyethoxycarboxylates; the cation being an alkali metal or alkaline earth metal (sodium, potassium, lithium, magnesium), a substituted or unsubstituted ammonium residue (methyl dimethyl-, trimethyl-, tetramethylammonium, dimethylpiperidinium ...) or derivative of an alkanolamine (monoethanolamine , diethanolamine, triethanolamine ...) ;; alkyl ester sulfonates of formula R-CH (SO3M) -COOR ', where R represents a Cg-20, preferably C10-C16, alkyl radical, R' represents a C1-C6, preferably C1 -C3 alkyl radical , and M represents an alkaline cation (sodium, potassium, lithium), substituted or unsubstituted ammonium (methyl-, dimethyl-, trimethyl-, tetramethylammonium, dimethylpiperidinium ...) or derivative of an alkanolamine (monoethanolamine, diethanolamine, triethanolamine. ..) Mention may very particularly be made of methyl ester sulfonates in which the R radical is C14-C16; alkylsulphates of formula ROSO3M, where R represents an alkyl or hydroxyalkyl radical in C1 0-C24, preferably in C1 2-C20 and very particularly in C1 2-
C18, M representing a hydrogen atom or a cation of the same definition as above, as well as their ethoxylenated (OE) and / or propoxylenated (OP) derivatives, having on average from 0.5 to 6 units, preferably from 0, 5 to 3 OE and / or OP patterns ;; alkyl amide sulfates of formula RCONHR'OSO3M where R represents a C2-C22, preferably C6-C20, alkyl radical, R 'represents a C2-C3 alkyl radical,
M represents a hydrogen atom or a cation of the same definition as above, as well as their ethoxylenated (EO) and / or propoxylenated (OP) derivatives, having on average from 0.5 to 60 EO and / or OP units; non-ionic surfactants. polyoxyalkylenated alkylphenols (polyethoxyethylenated, polyoxypropylenated, polyoxybutylenated) in which the alkyl substituent is C6C12 and containing from 5 to 25 oxyalkylene units; by way of example, mention may be made of TRITON X-45, X-1 14, X-100 or
X-102 marketed by ROHM & HAAS Cy .; glucosamides, glucamides, glycerolamides; polyoxyalkylenated Cg-C22 aliphatic alcohols containing from 1 to 25 oxyalkylene units (oxyethylene, oxypropylene); by way of example, we can cite the
TERGITOL 15-S-9, TERGITOL 2SL-6 NMW marketed by Union Carbide Corp.,
NEODOL 45-9, NEODOL 23-65, NEODOL 45-7, NEODOL 45-4 marketed by
SHELL CHEMICAL Cy., KYRO EOB marketed by THE PROCTER & GAMBLE Cy ;; . products resulting from the condensation of ethylene oxide or propylene oxide with propylene glycol, ethylene glycol and / or glycerol, such as
PLURONIC marketed by BASF; products resulting from the condensation of ethylene oxide or of propylene oxide with ethylenediamine, such as TETRONIC sold by BASF; amine oxides such as C10418 alkyl oxides of dimethylamines, oxides of Cg-C22 alkoxy ethyl dihydroxy ethylamines; the alkylpolyglycosides described in US-A-4,565,647; . C8-C20 fatty acid amides; . ethoxylated fatty acids; . ethoxylated fatty amides; . ethoxylated amines; cationic surfactants .alkyltrimethylammonium, dialkyldimethylammonium, alkyidimethylbenzylammonium, alkyldimethylethylammonium halides, Quart Esters; amphoteric and zwittenonlaues surfactants
alkylbetaines, α kyldimethylbetaines, alkylamidopropylbetaines, alkylamidopropyldimethylbetaines, alkyltrimethylsulphobetaines, imidazoline derivatives such as alkylamphoacetates, alkylamphodiacetates, alkylamphopropylbetaines, alkylamphodipropidopropionates, alkylamphodipropidopropionates and alkylamphodipropidopropionates, alkylamphodi and hydroxypropidopropionates protein hydrolysates.

- BUILDERS AGENTS, in amounts corresponding to approximately 5-50%, preferably approximately 5-30% by weight for liquid detergent formulas, or approximately 10-80%, preferably 15-50% by weight for detergent formulas in powders, such as: Inorganic bullders. polyphosphates (tripolyphosphates, pyrophosphates, orthophosphates, hexametaphosphates) of alkali metals, ammonium or alkanolamines; . tetraborates or borate precursors; . silicates, in particular those exhibiting a SiO21Na2O ratio of the order of 1.6 / 1 to 3.2 / 1 and the layered silicates described in US Pat. No. 4,664,839; . alkaline or alkaline earth carbonates (bicarbonates, sesquicarbonates) ;; . cogranules of hydrated alkali metal silicates and alkali metal carbonates (sodium or potassium) rich in silicon atoms in the Q2 or Q3 form, described in EP-A488 868; . crystalline or amorphous aluminosilicates of alkali metals (sodium, potassium) or of ammonium, such as zeolites A, P, X among others; zeolite A with a particle size of the order of 0.1-10 micrometers is preferred; water-soluble polyphosphonates, such as 1-hydroxy-1 ethane, diphosphonates, or alternatively methylene diphosphonate salts; water-soluble salts of carboxylic polymers or copolymers or their water-soluble salts such as:
polycarboxylate ethers (oxydisuccinic acid and its salts, monosuccinic tartaric acid and its salts, tartaric disuccinic acid and its salts;
hydroxypolycarboxylate ethers;
citric acid and its salts, Mellitic acid, Succinic acid and their salts;
salts of polyacetic acids (ethylenediaminetetraacetates, nitnlotriacetates,
N- (2 hydroxyethyl) -nitrilodiacetates); C5-C20 alkyl succinic acids and their salts such as, for example, 2-dodecenylsuccinates, lauryl succinates;
polyacetal carboxylic esters ;;
polyaspartic acid, polyglutamic acid and their salts; polyimides derived from the polycondensation of aspartic acid and / or glutamic acid; polycarboxymethylated derivatives of glutamic acid or of other amino acids.

- BLEACHING AGENTS, in amounts of approximately 0.1-20%, preferably approximately 1-10% by weight, optionally combined with BLEACH ACTIVATORS, in amounts of approximately 0.1-60%, preferably of about 0.5-40% by weight, such as: bleaching agents, perborates such as sodium perborate monohydrate or tetrahydrate; peroxygen compounds such as sodium carbonate peroxyhydrate, pyrophosphate peroxyhydrate, urea peroxyhydrate, sodium peroxide, sodium persulfate. Such compounds are preferably combined with a bleach activator generating in situ in the washing medium, a peroxycarboxylic acid. Among these activators, there may be mentioned tetraacetylethylene diamine, tetraacetyl methylenediamine, tetraacetyl glycoluryl, p-acetoxybenzene sulfonate sodium, pentaacetyl glucose, octaacetyl lactose, for example;
percarboxylic acids and their salts (called "percarbonates") such as magnesium monoperoxyphthalate hexahydrate, magnesium metachloroperbenzoate, 4-nonylamino-4-oxoperoxybutyric acid, 6-nonylamino-6oxoperoxycaproic acid, diperoxydodecanedioacid, peroxysuccinic acid nonylamide, Decyldiperoxysuccinic acid.

May also be mentioned non-oxygen bleaching agents, acting by photoactivation in the presence of oxygen, agents such as sulfonated aluminum and / or zinc phthalocyanines;
These agents can be combined with at least one of the anti-fouling or anti-redeposition agents mentioned below.

ANTI-SOILING AGENTS, in amounts of the order of 0.01-10%, preferably approximately 0.1-5%, and most particularly of the order of 0.2-3% by weight, such as: cellulose derivatives such as cellulose hydroxyethers, methylcellulose,
Ethylcellulose, hydroxypropyl methylcellulose, hydroxybutyl methylcellulose; polyvinylesters grafted onto polyalkylene backbones such as polyvinyl acetates grafted onto polyoxyethylene backbones (EP-A-219 048); polyvinyl alcohols ;; polyester copolymers based on ethylene terephthalate and / or propylene terephthalate and polyoxyethylene terephthalate units, with a molar ratio (number of units) of ethylene terephthalate and / or propylene terephthalate / (number of units) polyoxyethylene terephthalate of the order of 1/10 to 10/1, preferably of the order of 1/1 to 9/1, the polyoxyethylene terephthalates having polyoxyethylene units having a molecular weight of the order of 300 to 5000, preferably of the order of 600 to 5000 (US-A3,959,230, US-A-3,893,929, US-A-4,116,896, US-A4 702,857, US-A-4,770,666) ;; sulfonated polyester oligomers obtained by sulfonation of an oligomer derived from ethoxylated allylic alcohol, from dimethyl terephthalate and from 1,2 propylene diol, exhibiting from 1 to 4 sulfonated groups (US Pat. No. 4,968,451);
polyester copolymers based on propylene terephthalate and polyoxyethylene terephthalate units and terminated by ethyl or methyl units (US-A4 711 730) or polyester oligomers terminated by alkylpolyethoxy groups (US-A-4,702,857) or anionic sulfopolyethoxy groups (US-A4 721 580), sulfoaroyl (US-A-4 877 896) ;; polyesters-polyurethanes obtained by reacting a polyesters with a number molecular mass of 300-4000, obtained from adipic acid and / or terephthalic acid and / or sulfoisophthalic acid, and a diol of mass less than 300, on a prepolymer containing terminal isocyanate groups, obtained from a polyoxyethylene glycol with a molecular mass of 600-4000 and a diisocyanate (FR-A-2 334698).

- ANTI-REDEPOSITION AGENTS, in amounts of approximately 0.01-10% by weight for a powder detergent composition, of approximately 0.01 - 5% by weight for a liquid detergent composition, agents such as: monoamines or ethoxylated polyamines, polymers of ethoxylated amines (US-A-4,597,898, EP-A-1,984); carboxymethylcellulose; sulfonated polyester oligomers obtained by condensation of isophthalic acid, of dimethyl sulfosuccinate and of diethylene glycol (FR-A-2 236 926); polyvinylpyrollidones.

- CHELATANTS of iron and magnesium, in amounts of the order of 0.1-10%, preferably of the order of 0.1-3% by weight, agents such as: aminocarboxylates such as ethylenediaminetetraacetates, hydroxyethyl ethylenediaminetriacetates, nitrilotriacetates; aminophosphonates such as nitrilotris (methylene phosphonates); polyfunctional aromatic compounds such as dihydroxydisulfobenzenes.

- POLYMERIC DISPERSANTS, in an amount of the order of 0.1-7% by weight, to control the calcium and magnesium hardness, agents such as: water-soluble salts of polycarboxylic acids with a molecular mass of around 2000 to 100,000, obtained by polymerization or copolymerization of ethylenically unsaturated carboxylic acids, such as acrylic acid, maleic acid or anhydride,
Fumaric acid, Itaconic acid, Aconitic acid, Mesaconic acid, Citraconic acid, Methylenemalonic acid, and in particular polyacrylates with a molecular mass of the order of 2000 to 10,000 (US-A -3 308 067), copolymers of arylic acid and maleic anhydride with a molecular mass of the order of 5000 to 75000 (EP-A-66 915); polyethylene glycols with a molecular mass of the order of 1,000 to 50,000.

- FLUORESCENCE AGENTS (BRIGHTENERS), in an amount of approximately 0.05-1.2% by weight, agents such as derivatives of stilbene, pyrazoline, coumarin, fumaric acid, cinnamic acid, azoles, methinecyanines, thiophenes, and those in particular described in "The production and application of fluorescent brightening agents" (M. Zahradnik, published by John Wiley & Sons, New York-1982-).

- FOAM REGULATING AGENTS, in amounts which may range up to 5% by weight, agents such as: monocarboxylic fatty acids, C1 0-C24 or their alkali, ammonium or alkanolamine salts, triglycerides of fatty acids; . saturated or unsaturated aliphatic, alicyclic, aromatic or heterocyclic hydrocarbons, such as paraffins, waxes; N-alkylaminotriazines; monostearylphosphates, monostearyl alcohol phosphates; polyorganosiloxane oils or resins optionally combined with silica particles.

- SOFTENING AGENTS, in amounts of approximately 0.5-10% by weight, agents such as clays.

- ENZYMES in a quantity which can range up to 5 mg by weight, preferably of the order of 0.05 - 3 mg of active enzyme / g of detergent composition, enzymes such as: proteases, amylases, lipases, cellulases, peroxidases (US-A-3,553,139,
US-A4 101,457, US-AQ 507,219, US-A4 261,868.

- OTHER ADDITIVES such as:. alcohols, chosen in particular from methanol, ethanol, propanol, isopropanol, propanediol, ethylene glycol, glycerin; buffering agents; .perfumes; pigments.

The polyalkoxylated amidoamines of the invention can also be used as a surface agent for textiles (lubrication, flame retardant, softening, etc.), as a surface agent for metals (anti-corrosion, lubrication, detergency, etc.), as an agent. antistatic for fibers and films of mineral or organic polymers.

They can also advantageously form part of the composition of formulations used for cleaning optical lenses or accessories coming into prolonged contact with the mucous membranes or the eyes.

The polyalkoxylated amidoamines of the invention can also be used, alone or in combination with other surfactants or additives, in agrochemical formulations as emulsifiers or dispersants of plant protection active materials. Such formulations are in particular described in the commercial brochure “Auxiliaries for Agrochemical Formulations” published by RHONE-POULENC
GERONAZZO SpA, and can be suspensions, emulsions, emulsifiable concentrates, suspo-emulsions, redispersible granules, or even gels. Such a list is of course not exhaustive. Agrochemical active ingredients which may be concerned are herbicides, insecticides, fungicides, such as those described in "The Pesticide Manual" (9 "edition, CR Workling and RJHance, eds, published by The British Crop. Protection Council).

Concrete but nonlimiting examples of the present invention will now be presented.

EXAMPLES
The measurements of the dispersing, detergent and emulsifying powers of the polyalkoxylated amidoamines of the invention were carried out as follows:
DISPERSING POWER
PRINCIPLE
The dispersing power is quantified by noting the stability over time of a powder dispersed in an aqueous medium (hard water at 30 "HT, ie containing 120 mg of Ca ++ per liter) using a suspensivity test.

Suspensivity is defined as the quantity of particles remaining in suspension after a given time in a column of liquid of given height, expressed as a percentage relative to the quantity present at the start. This test, derived from the method
CIPAC (Collaborative International Pesticides Analytical Council Ltd) MT 15-1970-, has been adapted for a draft standard by the Commission for Test Methods (ASPA) "Method for evaluating the dispersing power of surfactants".

This test makes it possible to classify the surfactants as dispersing agents or not.

PROCEDURE - Solid in suspension
The powder selected is rutile titanium oxide RL 6849 marketed by RHONE
POULENC. It is a surface treated white pigment. It is coated with silica (SiO2: 0.79%) and alumina (Al2O3: 2.82%) and has been surface treated with an organic treatment which makes this pigment compatible with lipophilic media. This product is not dispersible in water.

The main properties of RL 68 * are defined as follows:
- Average particle size: 0.35 um
10% <0.17 ijm
90% <1.02 ijm
-TiO2total 93.8
- pH 7.2
- Specific surface 15.5 m2 / g
- Density 3.9 to 4.1 g / cm3 - Preparation of a concentrated pre-dispersion
2.5 g of TiO2 are weighed out in a 50 ml beaker. 0.50 or 0.75 or 1.25 grams of hard water containing 10% by mass of the product to be tested is added, so as to obtain a mixture containing 2, 3 or 5% of this product relative to the oxide titanium. So:
For 2% of product, it is necessary ... ..: 0.50 g of 10% solution
For 3% of product, it is necessary ..... ... 0.75 g of 10% solution
For 5% of product, it is necessary .... ........: 1.25 g of 10% solution.

The whole is dispersed manually using a glass stirrer, adding, if necessary, a little water at 30 ° C. until a very smooth and homogeneous flowable paste is obtained.

- diluted disDersion
The concentrated dispersion is poured into a 250 ml graduated cylinder with ground-glass stopper, rinsing the beaker with water at 30 "HT. The level of the test tube is made up to 250 ml with the same hard water at 30" HT. .

The concentration of titanium oxide dispersed in water is then 1% by weight.

The test tube, held by the neck and its stopper, is twisted 30 times in a row, in about 5 seconds for each phase. It is left to stand for 1 hour at laboratory temperature.

After this time has elapsed, the upper 225 ml are withdrawn, taking care not to stir the suspension. The aspiration is carried out with a sufficiently long glass tube, connected to a water pump via a vacuum flask with a capacity of 3 liters. The lower 25 ml are then poured into an aluminum capsule (70 × 20 mm), the empty weight of which has previously been measured with a balance accurate to within 1/10 mg. The test tube is rinsed with distilled water, and the rinsing water is collected in the capsule.

The capsule is placed for drying in an oven at 105 ° C. for 3 hours.

- Calculation of suspensivity
Mg is the mass initially introduced in grams of the TiO2 powder and of the product to be tested,
M1 is the mass of the dry extract found in the lower 25 ml of the test tube, weighed on a precision balance to 1/10 of a mg.

The suspensivity is given by the following calculation formula:
suspensivity = (MOM1) 1225 x 250 / mu x 100
We consider that:
a suspensivity greater than 90%, with 3% of product to be tested relative to TiO2, corresponds to a good dispersant;
a suspensivity greater than 90%, with 5% of product to be tested relative to TiO2, corresponds to an average dispersant;
a suspensivity of less than 90% with 5% of product to be tested compared to
TiO2 is a bad dispersant.

DETERGENT POWER
PRINCIPLE
The test simulates a simplified machine wash, using a tergotometer. It consists in washing samples of soiled tissue at 40 ° C. in a standard and uniform manner, with only the product to be tested and sodium bicarbonate to stabilize the pH. The washing lasts thirty minutes and the detergency is evaluated by measuring the whiteness of the pieces of fabric, before and after washing, using a colorimeter.

EQUIPMENT AND MATERIAL
Material: - Tergotometer: "US TESTING Co Inc" HOBOKEN NJ Model 7243.

- Ice machine for ironing fabric samples after washing.

- "Dr Lange LUCI 100" color measuring device.

Fabrics
Standard fabrics are manufactured by the CFT (Center For Test materials) or by the company "Test Fabric". They have the following characteristics:
Standard soiled fabrics (soiling) number of pieces per test
- Soiled cotton CS-3 CFT (wine) 2
- Soiled cotton K 10D CFT (mineral oil and carbon black) 2
- Soiled cotton AS-2 CFT (mineral oil and carbon black) 2
- Polyester cotton EMPA 104 CFT (mineral oil and carbon black) 2
- Polyester Dacron type 54 Test Fabric (mineral oil and carbon black) 2
Standard white fabrics - Cotton CN 1 white, not soiled, from CFT 5 - Polyester cotton PCN 1, white, not soiled, from CFT 5, i.e., for each test, a total of 20 pieces of fabric.

Products - "LABS", technical sodium dodecylbenzenesulphonate (ALDRICH) is the reference product.

- PROLABO Rectapur 99% NaHCO3 sodium bicarbonate. Used to stabilize the pH of cleaning baths around 8.6.

PROCEDURE
Detergency test
The tergotometer is a device made up of 4 stainless steel 2-liter pots on which are fitted stirrers that are set at 50 cycles per minute (100 back and forth). The pots are placed in a tank of water regulated at 40 "C.

In each pot we put 1 liter of permuted water containing:
- 1 gram of surfactant
- 1 gram of baking soda.

When the water is at temperature, the pots are introduced into the thermostatted bath, simultaneously triggering the agitation and a stopwatch.

At the end of washing (30 minutes) the baths are recovered (250 cc) for pH control.

The fabrics are rinsed three times in tap water, then hand-wrung and dried flat individually between two sheets of white absorbent paper.

The fabrics are again put between two sheets of clean absorbent paper, and ironed in the ice machine at a temperature close to 110 "C.

Color measurement
The measurements are carried out with the "LUCI 100" colorimeter before and after washing according to the "L", "a", "b" system (scale from black to white, from green to red, and from blue to yellow) to measure the detergent power of the surfactants tested (increase in the whiteness of soiled pieces of fabric).

Calculation of the deterence
The DE (detergency) value is calculated for each type of fabric by making the geometric sum of the color differences DL, Da and Db before and after washing on soiled fabrics:
Is
detergency DE = (DL2 + Da2 + Db2) 112
EMULSIFYING POWER
The test described below makes it possible to determine whether or not a product has good emulsifying properties with respect to a given lipophilic phase.

PROCEDURE
The emulsifying power is determined using a 100 ml graduated cylinder with ground-glass stopper. The test tube is filled with 90 ml of distilled water. 10 ml of the “oil” + surfactant mixture are added with a pipette. 20 successive reworkings are carried out while holding the test piece by its stoppered end. The behavior of the mixture is observed after 1 minute, 5 minutes, 15 minutes and 1 hour.

The quantity of emulsifier product to be tested used is approximately 1900 relative to the total mixture.

Under these severe test conditions (no optimization of the concentration of the product to be tested, little energy supplied to the system), a good emulsifier gives a milky dispersion that is stable for at least 5 minutes. The creaming phenomenon is slow and no significant coalescence or lightening is observed over the entire height of the specimen for at least 24 hours.

EXAMPLE i:
The cocoyl radical means that a cut of fatty acids originating from copra was used for the synthesis. Its composition is as follows:

<tb> I <SEP> number <SEP> of <SEP> carbon <SEP> I <SEP> 8 <SEP> 10 <SEP> 12 <SEP> 8 <SEP> | <SEP> 14 <SEP> | <SEP> 12 <SEP> 16 <SEP> 16 <SEP> 18
<tb><SEP>%<SEP> molar <SEP> 9.1 <SEP> 5.8 <SEP> 48.5 <SEP> 17.7 <SEP> 9.0 <SEP> 9.4
<tb> a) hydrolysis of N- (2-hydroxyethyl) -undecyl 2-imidazoline
The hydrolysis of N- (hydroxyethyl-2) -undecyl imidazoline was carried out under the following conditions:
Water (10% by weight) is added to N- (2-hydroxyethyl) -undecyl imidazoline. The gel thus obtained is stirred in the absence or presence of sodium hydroxide. Samples are taken over time and the composition of the reaction medium is determined by H1 NMR analysis, based on the relative importance of the signals corresponding to the methylene-α protons of imidazoline (2.04 ppm), of N ((( (2-hydroxyethyl) 2-amino) ethyl) -dodecamide (1.97 ppm), and N- (2-aminoethyl) -N (2-hydroxyethyl) -dodecamide (2.22 ppm).

The molar ratio (RM) described in the table below is as follows:
RM = N - ((2-hydroxyethyl) 2-amino) ethyl) -dodecamide
N- <aminoethyl-2) -N- (hydroxyethyl-2) -dodecamide

<tb> tests <SEP> NaOH <SEP> temperature <SEP> duration <SEP> conversion <SEP> RM
<tb><SEP> (molar%) <SEP> eC) <SEP> (hrs) <SEP> (%)
<tb><SEP> 1 <SEP> 0 <SEP> 25 <SEP> 100 <SEP> 86 <SEP> 1.1
<tb><SEP> 2 <SEP> 1 <SEP> 80 <SEP> 5 <SEP> 80 <SEP> 3
<tb><SEP> 3 <SEP> 1 <SEP> 95 <SEP> 5 <SEP> 89 <SEP> 3
<tb><SEP> 4 <SEP> 2 <SEP> 95 <SEP> 5 <SEP> 95 <SEP> 4.9
<tb><SEP> 5 <SEP> 5 <SEP> 95 <SEP> 5 <SEP> 96 <SEP> 7.3
<tb> b) hydrolysis of N- (2-hydroxyethyl) cocoyl imidazoline
The cocoyl imidazoline is heated to 80 ° C., then the necessary quantities of water and sodium hydroxide are added, then the reaction medium is heated to 90 ° C. for a given time. The composition is determined by liquid chromatography with an evaporative light scattering detector.

<tb> tests <SEP> NaOH <SEP> water <SEP> duration <SEP> conversion <SEP> ratio
<tb><SEP> (mol%) <SEP> (% <SEP> Weight) <SEP> (hrs) <SEP> (%) <SEP> molar
<tb><SEP> 6 <SEP> 2.5 <SEP> 11 <SEP> 2 <SEP> 96 <SEP> 10.2
<tb><SEP> 7 <SEP> 2,5 <SEP> 20 <SEP> 2 <SEP> 99 <SEP> 196 <SEP>
<tb><SEP> 8 <SEP> 2.5 <SEP> 33 <SEP> 2 <SEP> 99 <SEP> 188 <SEP>
<tb><SEP> 9 <SEP> 2.5 <SEP> 50 <SEP> 2 <SEP> 99 <SEP> 15
<tb>

EXAMPLES 2
Ethoxylation procedure
Hydrolysis procedure
Hydroxyethyl cocoyl imidazoline (1784 g) is hydrolyzed in the presence of water (10% by weight) and 86% potassium hydroxide (8.7 g) for 110 minutes at 800C.

Analysis of the reaction medium shows a conversion of 92% and an MR molar ratio, as defined in Example 1, equal to 12.8.

Example 2a:
Procedure for Ibmidoamine 1.2 OE
The reaction mass is then brought to 1000C and ethylene oxide (325 g) is added over 20 minutes. The product is then left to stand at 120 ° C. for 30 minutes.

The water is then distilled by flushing with nitrogen at a temperature of 110 ° C. for 40 minutes. The water content is 0.3% (Karl-Fischer).

Analysis of the reaction medium by liquid phase chromatography with an evaporative light scattering detector shows that the residual amidoamine content is less than 0.1% by weight.

This gives the mixture N - ((bis (2-hydroxyethyl) amino-2) ethyl) -dodecamide / N ((bis (2-hydroxyethyl) amino) ethyl) - N '- (2-hydroxyethyl) -dodecamide according to weight contents of 95% and 5% respectively and in the form of a pale yellow liquid (mixture hereinafter called the product (or composition or surfactant) of Example 2a).

Its physical properties are as follows: - cntiaue micellar concentration: 0.045 g / l (20 "C - pH = 7) - superhclel tension 27.5 mN / m (20" C - 1 9/1 - pH = 7) - wetting power: 2.5 g / l (20 "C - distilled water - pH = 7, NFT 73-406 ISO 8022) - foaming power: (20" C - 1 g / l - distilled water - pH = 6, NFT 73-404 ISO 696)
volume of foam at 30 seconds = 350 ml;
at 3 minutes = 330ml;
at 5 minutes = 330 ml.

- dispersing power: (dispersion of TiO2 - pH = 7)
calcium water 30 HT,
without addition of 1 EO amidoamine, the suspensivity is: 2.3%
with 3% """" 35.5%
with 5% """" 98.9%
The product is a good dispersant.

- emulsifying power:
xylene time
1 minute stable
5 minutes stable
15 minutes stable
1 hour stable
By way of comparison, by replacing, in xylene (HLB required of 14), the product of
Example 2 has the same amount of nonylphenol containing 10 ethylene oxides (HLB
of the order of 14), it is observed that one obtains under the same operating conditions,
a milky emulsion, stable for 15 minutes; after 1 hour, 4 ml of
creaming.

Example 2b:
Procedure for amidoamine 6.8 OE
The mixture of N - ((bis (2-hydroxyethyl) ami no-2) ethyl> -dodecamide and N - ((bis (2-hydroxy-ethyl) amino) ethyl) -N '- (2-hydroxyethyl) -dodecamide , obtained as described in the preceding example, is heated to 16000 and ethylene oxide (1600 g) is added over 2 hours, followed by a stage of 30 minutes at 16000. After neutralization of the catalyst with acetic acid, the reaction medium is filtered through absorbent earth (Clarcel DIC).

The average number of ethylene oxide calculated from the ethylene oxide feed is 6.8.

A mixture of N - ((bis (poly (oxy-ethanediyl-1,2) amino-2) ethyl) aodecamide and
N - ((bis (poly (1,2-oxy-ethanediyl) amino) ethyl) -N '- (poly (1,2-oxy-ethanediyl)) - dodecamide (mean degree of ethoxylation 6.8) according to weight contents of 95% and 5% respectively and in the form of an orange-yellow liquid (mixture hereinafter called the product (or composition or surfactant) of Example 2b).

Its physical properties are as follows: - critical micellar concentration: 0.07 g / l (20 "C - pH = 7) - surface tension: 33.2 mN / m (20" C - 1 gii - pH = 7) - wetting power: 5.2 g / l (20 "C - distilled water - pH = 7, NFT 73-406 ISO 8022)
1.0 g / l (50 "C - distilled water - pH = 7) - foaming stirrer: (20" C - 1 g / l - distilled water - pH = 6, NFT 73-404 ISO 696)
volume of foam at 30 seconds = 260 ml; at 3 minutes = 250 ml;
at 5 minutes = 250 ml.

- detergent power: (simulated washing using a tergotometer)
The cumulative detergency, measured on the different types of fabrics, results in
following results, taking laurylbenzene sulfonate (LABS) for reference with
a detergency "DE" equal to 100:
LABS DE = 100
NaHCO3 DE = 39.9
amidoamine 6.80 EO (product of example 2b) DE = 102.6
The detergent power of the product according to the invention is therefore at least equal to that of the
LABS.

EXAMPLE 3
The object of this example is to show the ability of the compounds according to the invention to clean metal surfaces, and more generally hard surfaces.

The test used for degreasing metal plates is as follows: i / lubricating plates
Pre-degreased steel plates from Q-Panel "(R-36, type Dull matte finish, dimensions 0.8 x 76 x 152 mm) are used.

The plates are immersed for 2 minutes in an oil then suspended for draining for 24 hours.

The test is carried out with two oils:
- TOTAL 200 Neutral paraffinic oil.

- PHYTOROB PHT rapeseed oil (triglyceride).

2 / washing and rinsing
The greased plates are immersed in the detergent solution at 500C.

The detergent solution is a solution in deionized water, comprising 20 g / l of a basic detergent, of the type of Parco detergents (Parker) free from additional surfactant, to which 1 g / l of surfactant to be tested has been added.

The plates are rinsed with running water for 5 seconds for each side (water flow rate 2 Vmin). The temperature is 15 to 17 "C.

One or more wash-rinse cycles can be carried out.

The surfactants tested are
- product of example 2b (product according to the invention)
- ethoxylated nonylphenol comprising 10 ethylene oxide units (IGEPAL NP10).

31 Rating
The detergent power of the surfactant associated with the basic solution is measured by the so-called water film evaluation method (ASTM F 22-65). The detergent power is proportional to the surface of the plate covered by a continuous film of water after rinsing.

The marks awarded range from 0 to 4. The mark 0 corresponds to a total absence of wetting (ie an absence of degreasing), the note "4" corresponds to a total wetting of the plate on both sides (ie a complete degreasing) .

4 / The results are as follows.

a) paraffin oil:
The ratings awarded were after a wash cycle with a total immersion time of one minute.

PARCO detergent without additional surfactant 0
IGEPAL NP10 4 product of Example 2b 4 b) rapeseed oil.

Ratings were assigned after several wash cycles, for a total immersion time of 10 minutes.

PARCO detergent without additional surfactant 0
IGEPAL NP10 4 product of example 2b 4
The product according to the invention has remarkable detergent characteristics equivalent to those of IGEPAL NP10. It should be noted that the conventional surfactants used in this application only give a rating of 4 after a total immersion time of 15 minutes.

EXAMPLE 4
The object of this example is to measure the detergent power in hand washing-up liquid applications.

The detergent power was measured by an ASTM dishwashing detergency test.

The principle is to observe the evolution of the level of foam in the detergent bath during the washing of soiled plates. We note the number of dishes washed when there is no foam left on the surface of the bath. Each formula is tested twice; if the two results do not differ by more than one base, the result is considered significant.

Conditions: 2 grams of dirt (margarine + flour) per plate
water hardness 390 ppm CaCO3 * product A: sodium lauryl ether sulfate (2 moles of ethylene oxide) and
product of Example 2a; * product B: sodium lauryl ether sulfate (2 moles of ethylene oxide) and
product of example 2b
(mean degree of ethoxylation 6.8).

<tb>

<SEP> products <SEP> A <SEP> A <SEP> B <SEP> B <SEP> LESNa <SEP> Product
<tb><SEP> commercial
<tb><SEP> LESNa / (LESNa <SEP> + <SEP> 0.5 <SEP> 0.75 <SEP> 0.5 <SEP> 0.75 <SEP> 1
<tb><SEP> product)
<tb> number <SEP> of plates <SEP> 16-17 <SEP> 19-19 <SEP> 10-10 <SEP> 12-13 <SEP> 15-15 <SEP> 18-19
<tb><SEP> washed
<tb><SEP> aspect <SEP> formula <SEP> ~ <SEP><SEP> gel <SEP> ~ <SEP><SEP> gel <SEP> liquid <SEP> liquid <SEP> liquid <SEP> liquid
<tb>
LESNa = sodium lauryl ether sulfate.

It is observed that the product A according to the invention achieves the performance levels of the commercial product but with the advantage of being completely harmless to the user.

EXAMPLE 5
The object of this example is the evaluation of compositions intended for cosmetic applications.

The level of ocular irritation of the products of Examples 2a and 2b was evaluated by in vitro test in comparison with non-irritating or mildly irritating surfactants such as cocoamphodiacetates (for example Miranol C2M *, marketed by Rhone
Poulenc) (irritation data published in Journal of the American College of
Toxicology, Volume 9, number 2, 1990, p121 and following).

The test used is the erythrocyte hemolysis test.

The procedure used is that described by RW LEWIS in the article A comparison of two cytotoxicity tests for predicting the ocular irritancy of surfactants ", published in
Toxicology in Vitro, Vol. 7, No. 2, pp 155-158 (1993), Pergamon Press Ltd.

The concentrations of surfactant hemolyzing 50% of the erythrocyte population (denoted TC50 in the publication cited above) are:

<tb> Example <SEP> Products <SEP> TCSO <SEP>
<tb><SEP> (mg / l) <SEP>
<tb><SEP> Miranol <SEP> C2Me <SEP> 350
<tb><SEP> 2a <SEP> N - ((bis (2-hydroxyethyl) amino-2) ethyl) <SEP> dodecarnid <SEP> and <SEP> 458
<tb><SEP> N - ((bis (2-hydroxyethyl) amino) ethyl) -N '- (2-hydroxyethyl) - <SEP>
<tb><SEP> dodecamide
<tb><SEP> 2b <SEP> N - ((bis (poly (oxy-ethanediyl-1 <SEP> .2) amino-2) ethyl) -dodecamide <SEP> and <SEP> 696
<tb><SEP> N - ((bis (poly (oxy-ethanediyl- <SEP> 1 <SEP>, 2) amino) ethyl) -N '- (poly (oxy- <SEP>
<tb><SEP> ethan <SEP> ediyl- <SEP> 1 <SEP>, 2)) - dodFcamide <SEP>
<tb><SEP> (average degree <SEP><SEP> of ethoxylation <SEP> 6.8)
<tb>
These concentrations measured for the products of Examples 2a and 2b show that a higher concentration of the products of Examples 2a and 2b is required with respect to that of Miranol C2M * to hemolyze 50% of the red blood cells; the products of Examples 2a and 2b are therefore less irritating than Miranol C2M *, itself slightly irritating to the eye.

The classification established by the publication referenced above shows that the products of Examples 2a and 2b belong to the category of mildly irritating products.

The products of Examples 2a and 2b can be used to reduce the irritant potential of solutions of anionic surfactants generally used in the formulations of shampoos, bubble baths or washing up liquid by hand.

For example1 the TC50 concentration for sodium lauryl ether sulfate (2 moles
ethylene oxide) is 295 mg / l.

The following tables show the evolution of TC50 concentrations as a function of
compositions of mixtures:
product A: sodium lauryl ether sulfate (2 moles of ethylene oxide)
product B: product of example 2a
product C: product of example 2b

<tb> A <SEP> (%) <SEP> B <SEP> (%) <SEP> TC <SEP> 50 <SEP> (mg / l) <SEP>>
<tb><SEP> 100 <SEP> 0 <SEP> 295
<tb><SEP> 75 <SEP> 25 <SEP> 429
<tb><SEP> 50 <SEP> 50 <SEP> 512
<tb><SEP> 25 <SEP> 75 <SEP> 475
<tb><SEP> O <SEP> 100 <SEP> 458
<tb>

<tb> A <%) <SEP> C <SEP> (%) <SEP> TC <SEP> 50 <SEP> (mgll) <SEP>
<tb><SEP> 100 <SEP> 0 <SEP> 295
<tb><SEP> 75 <SEP> 25 <SEP> 409
<tb><SEP> 50 <SEP> 50 <SEP> 446
<tb><SEP> 25 <SEP> 75 <SEP> 556
<tb><SEP> 0 <SEP> 100 <SEP> 696
<tb>
EXAMPLES 6
These examples illustrate the preparations of compositions intended for cosmetic applications.

Example 6a:
Gel toothpaste composition
The four phases A, B, C and D are prepared separately by mixing the following compounds:
Phase A:
- water 20.65% by weight
-caraghenanne 1%
- NaF 0.23%
- sodium benzoate 0.5%
- sodium saccharinate 0.02% Phase B:
- sorbitol 30.0%
- glycerin 20.0%
- maltilol 5.0% Phase C:
- silica TIXOSIL 73 17.0%
Phase D: flavor 1.0%
- 30% aqueous solution of 4.5%
surfactant of example 2a
- coloring 0.1%
The components of phase A are dispersed with vigorous stirring at 50 ° C. Phase B is then added and then the silica. The introduction of phase D is carried out with moderate stirring and under vacuum to prevent the formation of bubbles. A dental paste is thus obtained which is well tolerated by the mucous membranes.

Example 6b:
Preparation of a gel toothpaste composition
The procedure is as above except for the fact that phases C and D are as follows: PhaseC.

- silica TIXOSIL 73 17.5%
Phase D:
- sodium lauryl sulphate 2.0%
- 30% solution of 2% surfactant
from example 2a
Example 6c:
Preparation of a composition for mouthwash.

The three phases A, B and C are prepared separately by mixing the following compounds: PhaseA.

- water 74.78% by weight
- allantoin 0.05%
- glycerin 10.0%
- maltilol 5.0%
- NaF 0.05%
- mallow extract 0.10%
Phase B:
- polysorbate 60 0.6%
- flavor 0.05%
methanol 8.0%
PhaseC.

- surfactant of Example 2b 1.0%
- sodium saccharin 0.015%
- sodium benzoate 0.3%
- lactic acid quantity necessary to obtain a pH of 6.4
The mouthwash composition is obtained by simply mixing phases A, B and C.

Example 6d:
Preparation of a mouthwash composition - ethanol 6.0% - glycerol 2.0% - sodium benzoate 2.0% - sodium bicarbonate 1.5% - sodium saccharinate 0.2% - allantoin 0.3% - xanthan gum (Rhodicare X 401) 0.2% - surfactant from example 2a 2.5% - water-soluble mint flavoring 2% - polysorbate 20 1% - coloring sufficient quantity to obtain the coloring
desired - citric acid quantity sufficient to have a pH of 4.7 - distilled water 100% complement
The composition is prepared by simply mixing the components. We mix the water and
xanthan gum with vigorous stirring and then introduced with moderate stirring the
other constituents of the composition.

Example 6e:
Preparation of a composition for 2 in 1 liquid toothpaste
The composition is as follows: - xanthan gum (Rhodicare X 401) 0.3% - sorbitol (70% solution in water) 69.4% - sodium monofluorophosphate 0.76% - sodium saccharinate 0.2% - benzoate 0.2% - silica Tixosil 73 15.0% - coloring agent sufficient quantity to obtain the coloring
desired - aroma sufficient quantity to obtain the fragrance
desired - surfactant from Example 2b 4.2% - 100% additional water
The sodium salts are dissolved in water and the sorbitol is added with vigorous stirring, then the xanthan gum.

The resulting mixture is left to stand for 30 minutes and then the silica and the dye are introduced with stirring for 15 minutes.

The solution is degassed in vacuo for 45 minutes after which the flavor and surfactant are added in vacuo with moderate stirring.

EXAMPLES 7
The purpose of these examples is to evaluate the characteristics of washing bases comprising the compositions according to the invention.

Example 7a:
The formulation of the washing base is as follows: sodium lauryl ether sulfate 9% composition of example 2a 3% deionized water 88%
The percentages are given by dry weight.

The formulations were neutralized with citric acid or lactic acid to obtain a pH of 6 and the viscosities of the resulting compositions were measured.

In each case, the compositions obtained are clear.

The results are as follows:
lactic acid: viscosity 180 mPa.s.

citric acid: viscosity 6050 mPa.s.

Example 7b:
The same washing base formulation is used as for Example 7a and the pH of those is adjusted to 6 by adding citric acid.

Variable amounts of electrolyte were then added: sodium chloride and ammonium chloride and the viscosity was measured (Brookfield needle No. 4, 10 rpm).

By way of comparison, the same manipulations were carried out with a washing base comprising the same amount of Miranol Ultra C32 using sodium chloride.

The results are as follows:

<tb><SEP> NaCI <SEP> (%) <SEP> 0.7 <SEP> 1 <SEP> 2 <SEP> 3
<tb> viscosity <SEP> (mPa.s)
<tb><SEP> 7b <SEP> 390 <SEP> 7410 <SEP> 350 <SEP> 0
<tb><SEP> Miranol <SEP> Ultra <SEP> C32 <SEP> O <SEP> 0 <SEP> 5000 <SEP> 33000
<tb>
It is observed that the washing base comprising the composition according to the invention requires less electrolyte than Miranol in order to obtain a high viscosity.

<tb>

<SEP> NH4CI <SEP> (%) <SEP> 0.7 <SEP><SEP> 1 <SEP> 2 <SEP> 3 <SEP>
<tb> viscosity <SEP> (mPa.s)
<tb><SEP> 7b <SEP> 1100 <SEP> ~ <SEP><SEP> 12880 <SEP> 610 <SEP> 80
<tb>
Example 7c: evaluation of the foaming power of the washing base described in Example 7a in
using the modified Ross-Miles test (NF T73-404) explained below:
The measurements are carried out on solutions comprising the products of Example 2a
with sodium lauryl ether sulfate in respective proportions of 2/10.

The pH of the composition is adjusted to 6 with citric acid.

The concentration of the solution is 1 gram per liter of dry matter.

The foaming power is measured under two conditions, in distilled water and in hard water (0.1% CaCl2).

The results are as follows:

<tb><SEP> average <SEP> of <SEP> heights <SEP> of <SEP> foam <SEP> (ml)
<tb> time <SEP> distilled <SEP> water <SEP> hard <SEP> water
<tb> 30 <SEP> seconds <SEP> 340 <SEP> 380
<tb> 5 <SEP> minutes <SEP> L <SEP><SEP> 325 <SEP> 370
<tb>
The foaming power of the washing base comprising the composition according to the invention exhibits good foaming power at 20 ° C., improved in the presence of calcium chloride.

Example 7d:
Evaluation of the foam enhancer effect on a soap
The object of this example is to evaluate the enhancing power of the foam of the composition of Example 2a on potassium laurate.

To measure this effect, a test by successive reversals is carried out, consisting in carrying out the following steps:
50 ml of the test solution are poured into a 250 ml test tube.

30 reversals are then carried out (back and forth) at the rate of one reversal per second, after which the height of foam generated by the test is measured.

Formulations tested: (1) potassium laurate at 0.1% dry matter lauric acid 0.084%
KOH 0.024% additional water at 100% (2) potassium laurate at 0.1% dry matter and 0.03% of the composition of Example 2a lauric acid 0.084%
KOH 0.024% composition according to example 2a 0.03% 100% additional water
The results are as follows: (1) foam height = 10 ml (2) foam height = 33 ml.

It is therefore observed that the composition according to the invention promotes the formation of foam in a soap formulation.

Example 7e:
The object of this example is to evaluate the creaminess of the foam of the compositions according to the invention.

This was carried out by measuring the viscosity and the results were compared with those obtained for various products such as sodium cocoamphoacetate (Miranol Ultra C 32), sodium laurylethersulfate with 2 ethylene oxide units (Empicol ESB / 3M), laurylpolyglucose (Plantaren 1200 UP).

The test conditions are as follows:
Solutions comprising 0.1% dry matter in distilled water are prepared.

100 ml of the solutions to be tested are mixed for 30 seconds in a mixer
Kenwood at top speed.

The foam thus obtained is poured into a 600 ml beaker and the viscosity of the foam is measured over a period of 1, 3 and 5 minutes, using a Brooldield apparatus (needle No. 4, 20 rpm ).

The results are as follows:

<tb><SEP> viscosity <SEP> composition <SEP> Plantaren <SEP> Empicol <SEP> Miranol <SEP> Ultra <SEP> C32
<tb><SEP> example <SEP> 2a <SEP> 1200 <SEP> UP <SEP> ESB
<tb> àt = lmn <SEP> 670 <SEP> 470 <SEP> 490 <SEP> 570
<tb> to = <SEP> 3 <SEP> my <SEP> 790 <SEP> 590 <SEP> 730 <SEP> 800
<tb> to <SEP> t <SEP> = <SEP> 5 <SEP> mn <SEP> 940 <SEP> 590 <SEP> 960 <SEP> 980
<tb> aspect <SEP> of <SEP> foam <SEP> stable <SEP> foam <SEP> enough <SEP> foam <SEP> shiny <SEP> to <SEP> foam <SEP> to <SEP> bubbles
<tb> the <SEP> foam <SEP> compact <SEP> liquid <SEP> coarse <SEP> bubbles <SEP> ~ <SEP><SEP> fine
<tb>
The creaminess of the foam obtained with the composition according to the invention and its stability are superior to those of Empicol ESB and Miranol Ultra C32.

Example 71:
The aim of this example is to compare the effects on the foam and on the hair of the compositions according to the invention with known amphoteric products.

1 / sensory evaluation test of the foam
The test protocol is as follows:
About 2 ml of the test solution are taken and applied to dry hands. A small amount of water is then added and the formulation foamed.

After a first assessment of the criteria, a further small amount of water is added and frothed again.

The criteria are again assessed and the results are averaged.

The hands are washed in cold water and dried before a new application of the product to be tested.

The preferred formulation is then noted (two proposals are made at most).

The formulations to be tested are 10% solutions in water of the following products, the pH of which has been adjusted to 6 by adding citric acid:
solution A: composition of example 2a
solution B: Lauryl polyglucose (Plantaren 2000 / Henkel)
solution C: Sodium amphoacetate (Miranol Ultra C 32 / Rhone-Poulenc)
solution D: Cocoamidopropylbetaine (Tegobetain L7 / Goldschmidt)
The results, corresponding to the average of the 7 judges, are collated in the table below::

<tb><SEP> Foam <SEP> solution <SEP> A <SEP> solution <SEP> B <SEP> solution <SEP> C <SEP> solution <SEP> D
<tb> Quantity <SEP> + <SEP> + <SEP> + <SEP> +
<tb> smoothness <SEP> and <SEP> creamy <SEP> 0 <SEP> ~ <SEP><SEP> + <SEP> + <SEP> +
<tb> Aspect <SEP> homogeneous <SEP> homogeneous <SEP> homogeneous <SEP> heterogeneous <SEP>
<tb> size <SEP> of <SEP> bubbles <SEP> fine <SEP> coarse <SEP> fine <SEP> fine
<tb> facility <SEP> of <SEP> rinsing <SEP> + <SEP> + <SEP> + <SEP> +
<tb><SEP> soft <SEP> blocking <SEP> blocking <SEP> blocking
<tb>
The preferred product is solution A according to the invention with regard to the softness and smoothness of the foam. The amount of foam obtained with solution A is comparable to that obtained with commercial products.

2 / Derformance test
The objective is to compare the effects of the solution on the hair of the solution according to the invention with commercial products.

The criteria tested are the glide (ease of gliding of the comb through the hair in the dry state), the smoothness (softness of the hair to the touch) and the spring of the curl (tone, vigor of the curl and waves of the hair).

The test protocol are as follows: (a) The strands of hair are pretreated to damage them. This consists of washing with sodium lauryl ether sulfate. 5 washing-drying cycles are carried out.

(b) the damaged locks are then soaked for 5 minutes in 200 ml of the solution to be tested at 30 ° C. They are rinsed with lukewarm water for 1 minute and then dried in a hair dryer at the maximum power of the apparatus for 180 seconds.

(c) The locks are then compared in pairs on a panel of 15 judges.

The solutions treated are solutions A, C and D defined previously in point 1 /.

The results are shown below: Pelanablllté of the dry wick (criterion of the glide).

* 13 out of 15 judges preferred solution A over solution C,
* 10 out of 15 judges preferred solution A over solution D.

* The product of solution A is perceived as more slippery than that of solution
C (99% confidence interval) and we see a tendency of that of the solution
A to be more slippery than that of solution D (no significant difference).

sensonal evaluation of the touch of the wick (center of the smooth).

* 8 out of 15 judges preferred solution A over solution C,
* 12 out of 15 judges preferred solution A over solution D.

* There is a tendency for the product of solution A to be smoother than that of solution C (no significant difference) and that of solution A is perceived as smoother than that of solution D (confidence interval of 95 %).

The results of the sensory tests carried out show that the product according to the invention has significant advantages for its application in cosmetics, in particular conditioning properties of the hair.

Claims (11)

1 - Surfactant composition comprising a mixture of polyalkoxylated amidoamines of medium formulas (I) and (2):

in which: - R1, identical or different, represent a C2-C hydrocarbon group, linear or branched alkyl or alkenyl, cycloalkyl or alkylaryl, - R2, identical or different, represent hydrogen or a C1 C4 alkyl radical, - p, q, r, s and t, which are identical or different, represent whole or fractional numbers, equal to or greater than 1, preferably of the order of 1.1 to 50. said mixture comprising respectively from 99.9 to 0.1% by weight of product of formula (1) per 0.1 to 99.9% by weight of product of formula (2). 2 - Composition according to claim 1, characterized in that it has an amidoamide content of formula (1) of between 70 and 99% by total weight of the composition, and preferably, a content of between 95 and 99% by relative to the total weight of the composition. 3 - Composition according to any one of the preceding claims, characterized in that the radical R2 represents hydrogen or a methyl radical. 4 - Composition according to any one of the preceding claims, characterized in that it further comprises at least one anionic surfactant. 5 - Composition according to the preceding claim, characterized in that the content of the mixture of polyalkoxylated amidoamines is 1 part by weight per 0.1 to 100 parts, and more particularly from 1 to 20 parts, of anionic surfactant. 6 - Use of a composition according to any one of claims 1 to 5 in cosmetic compositions. 7 - Use of a composition according to any one of claims 1 to 5 in detergent compositions. 8 - Use of a composition according to the preceding claim in detergent compositions for textiles and metals. 9 - Use of a composition according to the preceding claim in detergent compositions for dishes or hard surfaces. 10 - Use of the mixture of polyalkoxylated amidoamines forming the subject of any one of claims 1 to 5. for reducing the irritation of solutions of anionic surfactants in the fields of cosmetics and detergents. 11 - Use of a surfactant composition according to any one of claims 1 to 3 in agrochemical formulations.