FR2778405A1 - N- (DIALKYLAMINO) ALKYL ALPHA CARBOXAMIDES, COMPOSITIONS CONTAINING SAME, PROCESSES FOR PREPARATION AND USES - Google Patents

Abstract

The invention concerns the use of alpha hydroxy carboxylic acid (AHA) derivatives as washing and/or conditioning agents for the skin and the hair. The invention also concerns novel AHA derivatives, compositions, in particular cosmetic and hair compositions containing them, and methods for preparing them.

Description

DESCRIPTION

  The invention relates to the use of alpha hydroxy acid derivatives

  carboxylic agents as washing agents for human skin and / or

hair.

  More specifically, the alpha hydroxy carboxylic acid derivatives

  belong to the group consisting of N- (dialkylamino) alkyl alpha carboxamides and their derivatives obtained by reaction (s) of acylation and / or quaternization, by reaction

  acylation and betainment and by acylation and oxidation reaction.

  The subject of the invention is also specific alpha hydroxy carboxylic acid derivatives, the cosmetic or capillary compositions containing

  said derivatives, and processes for their preparation.

  Cationic, zwitterionic and N-oxide surfactants are

  widely used in the field of cosmetics.

  Cationic surfactants are in particular sought for their conditioning function of the skin and the hair. Thus, when they are applied to the damp hair, the interactions between the hair are reduced and disentangling at the time of drying and combing is facilitated. These surfactants also make it possible to improve the texture and the softness of the hair, to avoid the formation of forks, to contribute to a better state of the hair, to prevent the damage due to

  external aggression, and to reduce the effects of static electricity by neutralizing

  apparent anionic charges. This last property can moreover

  be improved by the addition of an N-oxide derivative.

  Zwitterionic compounds are very mild to the skin and mucous membranes and reduce the irritation caused by anionic surfactants. They are also soluble in water and have good compatibility with other surfactants. In addition, just like cationic compounds, they contribute to

  to preserve the microbiological quality of the formulations by their bacteriostati-

  than. Finally, being electrically neutral, they have good insensitivity to

  variations in the ionic strength of the medium and their behavior is weakly

temperature.

  The compounds of the N-oxide type make it possible, just like the zwitterionic compounds, to adjust the viscosity of the formulations. They can also be foam boosters, but they are their emollient properties

which are the most sought after.

  It is also known that alpha hydroxy carboxylic acids (AHAs)

  exert a beneficial action on the skin.

-2-

  Human skin is composed of the outer epidermis and the subcutaneous dermis.

  located above the fatty tissues.

  The epidermis has four distinct layers: stratum corneum, stratum granulosum, stratum spinosum and basal stratum. The stratum corneum is the outer layer of the epidermis. It is composed of keratinocytes in phase

  terminal differentiation (corneocytes) and. lipids that fill the spaces

these intercellulars.

  In contact with AHA, cohesion of corneocytes of the stratum corneum and decreased which has the effect of causing desquamation. The skin is thus

smooth, soft and shiny.

  The desired effect, however, requires the application of relatively high AHA content composition (of the order of 2 to 15%) which causes some

  subjects irritation and tingling unpleasant.

  There are already known uses of AHA derivatives.

  In WO-A-95/05154, compositions for washing the skin and hair which contain an alpha hydroxy di- or tricarboxylic acid derivative in which either the hydroxyl group is esterified with an acyl residue or at least one

  a carboxylate function is esterified with an alkyl group.

  EP-A-0 327 379 describes humectants which can be used in cosmetic compositions which are amide derivatives obtained by reaction of a

  carboxylic acid or an ester of this acid with a N, Ndisubsti-

  killed. Seymour L. et al. (J.Am.Chem.Soc., Vol 81, pp.3083-3088, (1959)) describe

  the use of aminoalkylamides derived from glycolic, lactic and methyllactic acids

  as depressant agents of the central nervous system.

  These compounds are prepared by reaction of the ethyl ester of the acid

  carboxylic acid with a dialkylamine, followed by a quaternization step.

  In JP-A-06 234 714, amides of carboxylic acids, in particular glycolic acid, are used as activators for bleaching tissues.

by peroxides.

  In US-A-5 456 846, it is proposed to soften the laundry by means of salts

  quaternary ammonium amides or glyceric acid esters.

  Finally, in JP-A-06 228 070, the use of carboxybetaines is described.

  as humectants in cosmetic compositions. Carboxybene

  some are derivatives of carboxylic and hydroxycarboxylic acids.

  It goes without saying that there is a great need to seek to use products

  surfactant properties and low irritancy for

cosmetic and capillary

  The present invention therefore proposes to use N (dialkylamino) alkyl alpha

  hydroxycarboxamides and their derivatives as washing and / or conditioning agents

skin and hair.

  The invention relates firstly to the use as washing agents for human skin and / or hair conditioning of compounds belonging to the group consisting of: (i) compounds of formula: [Hi Z fNH - (CH2) pN J (R) R2 n (ii) the compounds of formula: [H 2 Z- [NH-IC 2 -NR] nX (11A) [H] 2 -NH - (CH 2) pN (R 2) (iii) compounds of formula: ## STR2 ## compounds of formula: ## STR1 ## compounds of formula: ## STR1 ## ## STR2 ## (v) the compounds of formula: ## STR2 ## in which ) compounds of formula: ## STR1 ## wherein

  Z represents the di- or polyvalent residue of an alpha hydroxy carboxylic acid

than,

  R represents an aliphatic chain, linear or branched, saturated or unsaturated

in C1-C21,

  R1, R2 and R3, which may be identical or different, represent a C1-C6 alkyl radical;

  C4, X represents a halogen atom or a group of formula -SO3-O-R3, R3 having the meaning given above, m is an integer ranging from 1 to 10, n, p and r, which are identical or different, are integers that can range from 1 to 4. The preferred compounds which are suitable for use according to the invention are the compounds of formulas (I), (II A), (II B), (III), (IV) and (V) in which Z is a residue of alpha hydroxy carboxylic acid chosen from the residues of formula: R4

-O-C-C-

  R5 0 in which: R4 and R5, identical or different, represent a hydrogen atom, a C1-C4 alkyl radical, or a radical of formula:

-L CH C-

R6 0

  in which R6 represents a hydrogen atom or -O-, and t is equal to 0, 1, 2 or 3. By way of example of residue Z, mention may be made of the residues of glycolic acids,

  lactic, 2-methyllactic, 2-hydroxybutanoic, 2-hydroxypentanol, 2 hydroxy

  hexanoic, malic, citramalic, tartaric, tartronic and citric.

  Even more advantageously, the compounds that can be used according to the invention are the compounds of formulas (I), (II A), (II B), (III), (IV) and (V) in which: Z represents a residue of alpha hydroxy carboxylic acid selected from

  residues of glycolic, lactic, 2-methyllactic, malic, tartaric, tartronic

that and citric, -5-

  R represents a linear or branched, saturated or unsaturated aliphatic chain

  C6-C21, R1, R2 and R3, which may be identical or different, represent a methyl, ethyl or propyl radical, R1 and R2 being preferably identical, X represents Cl, Br, I or a group of formula - SO3-O- R3, R3 having the meaning given above, m is an integer ranging from 1 to 8, n is an integer ranging from 1 to 3, pest is 3,

remains equal to 1.

  By way of examples of preferred acyl radicals of formula R-CO-, mention may be made of the octanoyl, decanoyl, 10-undecenoyl, lauroyl and palmitoyl radicals.

  stearoyl, oleoyl, eicosanoyl and behenoyl.

  The subject of the invention is also the preferred compounds of formula (III) and

  the compounds of formula (IV) and (V) described above.

  Another subject of the invention relates to compositions intended to be applied to the skin and the hair which comprise said compounds. These compositions are characterized in that they comprise: - (A) at least one compound of formula (III), (IV) or (V), and

  - (B) a vehicle compatible with a topical application.

  The content of compound (A) in the composition according to the invention may vary from 0.01 to 50% by weight of the composition, preferably 0.1 to 30% by weight and

more preferably from 1 to 25% by weight.

  The vehicle (B) is generally selected from cosmetically acceptable vehicles well known to those skilled in the art. The vehicle facilitates the distribution of the compounds (A) on the surface of the skin or the hair and also makes it possible to adjust

  the concentration of active material at the desired level.

  The vehicle is usually water or an organic solvent compatible with

  a topical application. By way of example, mention may be made of acetone and isopropyl alcohol.

  that, the triglycerides of C6-C24 fatty acids, the glycol ethers, the esters of

  polyalkylene glycol and C2-C4 acids, and volatile silicones.

  The compositions according to the invention may contain, in addition: one or more other surfactants well known to those skilled in the art, for example anionic, cationic, amphoteric or nonionic surfactants. The amount of these surfactants can reach 49.99% by weight of the composition, preferably 20 to 49.90% by weight, additives which can modify the physical characteristics or

chemical composition.

  By way of example of such additives, mention may be made of: fatty substances such as natural or synthetic oils, thickeners and gelling agents, active ingredients such as moisturizing agents, antioxidants, preservatives, * perfumes, and

ò the dyes.

  Depending on the nature of the vehicle and any additives, the compositions of

  The invention may have a solid, semi-solid or liquid appearance.

  The solid compositions may be in the form of a stick, a bread of

  cleaning, an impregnated pad or a moisturizing mask.

  The semi-solid compositions may be a milk obtained by dispersion of a fatty phase in an aqueous phase or vice versa, or a suspension or emulsion of soft consistency such as a cream, an ointment or a gel. The liquid compositions as for them can be a foaming lotion

or not foaming.

  As examples of cosmetic compositions, mention may be made of foaming baths, shower gels and mild liquid soaps. These compositions are also likely to have the properties of smoothing the skin, to give it

  softness, shine, shine and contribute to his good health.

  By way of example of hair compositions, mention may be made of shampoos, for example soft and frequently used, and after-shampoos which have particular

  property of conditioning hair, lotions and emulsions

the damaged hair.

  The preparation of the compounds of formula (I), (II A), (II B), (III), (IV) and (V) is

summarized in Figure 1.

  The processes that lead to their obtaining will be better understood at the

  light of the description which follows. These processes constitute another object of the invention.

  tion. A - Preparation of the compounds of formula (I) The process of preparation consists in reacting: an alkyl ester of alpha hydroxy carboxylic acid of formula: ## STR2 ## in which Z, m and n have the meaning given above and R7 represents a C1-C4 alkyl radical; and an amine of formula: ## STR3 ## in which R1, R2 and p have the meaning given previously to form the compound of formula: [H] Z [NH- (CH 2) pN] (I) The molar ratio of the amine of formula (VII) to the alkyl ester of alpha hydroxy carboxylic acid of formula ( VI) is generally between 0.8n and 3n,

  Preferably In and 2n, where n is the total number of ester functions.

  The reaction may be carried out in the presence of a solvent such as dimethyl

  formamide or an alcohol containing up to 6 carbon atoms, for example methanol, ethanol, propanol or isopropanol. However, we prefer to perform the

reaction in the absence of solvent.

  The process is generally carried out at a temperature of between 10 and 180 ° C., preferably 20 ° C. and 150 ° C., at atmospheric pressure and

  for a period ranging from 1 hour to 5 days, preferably 3 to 24 hours.

  At the end of the reaction, the reaction medium which contains the compound of formula (I) is recovered. The reaction medium may optionally undergo a concentration step, for example at a temperature that may vary from 50 to 200 ° C., and

  under a vacuum between 0.007 and 101.325 kPa.

  The compound of formula (I) may be used as such or undergo an addition step.

  purification, for example by distillation or recrystallization.

  B - Preparation of the compounds of formula (II A The process of preparation consists in reacting: the compound of formula: ## STR2 ## in which Z, R 1, R 2 , m, n and p have the meaning given above, and a quaternization agent of formula:

R3X (VIII)

  in which R3 and X have the meaning given above, to form the compound of formula:

0 2 0 / R!]

  The molar ratio of the compound of formula (I) to the quaternizing agent of formula (VIII) is generally between 1: 0, 80n and 1: 3n, preferably 1: 0, 9n

  and 1: 2n, where n is the total number of tertiary amine functions to quaternize.

  The reaction can be carried out in the presence of a solvent chosen from alcohols such as methanol, ethanol, propanol, isopropanol, butanol or isobutanol, ether oxides such as tetrahydrofuran or ethylene glycol dimethyl ether, and halogenated hydrocarbons such as dichloromethane, dichloroethane or chloroform. Alcohols such as isopropanol,

  halogenated hydrocarbons and ether-oxides.

  Advantageously, the reaction solvent is anhydrous. He's embarrassed-

  0.1 to 30 equivalents by weight, preferably 0.1 to

  20 equivalents, for 1 equivalent by weight of the compound of formula (I).

  The process is generally carried out at a temperature of between 10 and 80 ° C., preferably 20 ° to 70 ° C., for a duration that can vary from 0.5 ° C.

at 48 hours.

  At the end of the reaction, the reaction medium containing the compound of formula (II A) may optionally be treated with water in order to hydrolyze the excess

  quaternization agent. The reaction medium may undergo a concentration step

  tion, for example at a partial pressure of between 0.013 and 101.325 kPa, preferably 0.013 and 4 kPa. The residue obtained can then be solubilized with deionized and freeze-dried water which has the effect of improving the appearance of the solid.

resulting.

  It is possible that at the end of the reaction, a demixing of the reaction medium is observed. It then suffices to recover the compound of formula (II A) by decantation and, if appropriate, to wash it, for example by trituration in a

  said reaction solvents.

  C - Preparation of the compounds of formula (II B) The process of preparation consists in reacting: the compound of formula: [H] Z -NH (CH 2) pN () in which Z, R 1, R 2, m , n and p have the meaning given above, and an acylating agent of formula:

R-C-R8 (IX)

  where R has the meaning given above, and R8 represents an atom

  halogen, preferably Cl, or a diglyceryl radical whose acyl residues,

  or different, contain from 2 to 22 carbon atoms, preferably 7 to 22 carbon atoms, a -O-CO-Rg group wherein Rg represents a linear or branched hydrocarbon chain, saturated or unsaturated C 1 -C 21, of preference

  C6-C21, or a group -O-R10 in which R10 represents a C1-C6 alkyl radical;

  C4. to form the compound of the formula R-C-2 -NH- (CH 2) p -N I (11B) R - m LR 2 n When the acylating agent of formula (IX) is an acid anhydride, it is preferred to

that it be symmetrical (R = Rg).

  When the acylating agent is an ester, the radicals R and R 10 are preferably

  differently. This agent can be prepared in particular from acid cuts.

  C12 / C14, C16 / C18 or C12 to C18.

  The molar ratio of the compound of formula (I) to the acylating agent of formula (IX) and generally between 1: 095m and 1: 10m, preferably 1: 0.95m and 1: 6m, m being the number of total of alcohol functions to acylate. When the acylating agent

  is an acyl halide, a molar ratio ranging from 1: 0.95m to 1: 2m is preferred.

  The acylation reaction may be carried out in the presence of a solvent chosen from pyridine, ether-oxides such as tetrahydrofuran or ether

  dimethyl ethylene glycol, and halogenated hydrocarbons such as dichlo-

- 10 -

  romomethane, dichloroethane or chloroform. Halocarbons are preferred

  Genoa. The aforementioned solvent is advantageously anhydrous. It is generally used in a proportion of 0.1 to 30 equivalents by weight, preferably 0.1 to 20 equivalents, for 1 equivalent by weight of the compound of formula (I).

  The acylation reaction can also be carried out in the presence of a carbon

  alkali metal or alkaline earth metal hydrogencarbonate, eg potassium carbonate, sodium carbonate, hydrogen carbonate,

  potassium and sodium hydrogencarbonate.

  The molar ratio of carbonate or hydrogencarbonate to the compound of formula (I) is generally between 0.4m and 10Om, preferably 0.4m and 2m,

  where m is the total number of alcohol functions to be esterified.

  When the acylating agent is an acid anhydride or an acyl halide, the reaction is carried out at a temperature of between -10.degree. C. and +60.degree. C., preferably

  -5 and +30 C, and at atmospheric pressure.

  When the acylating agent is an ester, the reaction is carried out at a temperature of

  between 60 and 180 ° C., preferably 70 ° C. and 160 ° C., and at a pressure of

  between 0.013 and 101.325 kPa, preferably 0.013 and 10 kPa.

  The duration of the reaction may vary from 1 to 120 hours, preferably 2 to

48 hours.

  During the reaction, it is possible to add a phase transfer catalyst chosen from nonionic, cationic or anionic surfactants, by

  amines and compounds containing ammonium or phosphonium

  nium, crown ethers, cryptands, aminopolyethers, phosphorylsul-

  foxydes and esters of glycol or sorbitan.

  Examples of ammonium compounds that may be mentioned include hexadecyl trimethyl ammonium chloride, benzyl trimethyl ammonium chloride, trioctyl methyl ammonium chloride, tricapryl methyl ammonium chloride, tetrabutyl ammonium sulfate and tetrabutyl ammonium chloride or bromide. Preferably, hexadecyl trimethyl ammonium chloride, tricapryl methyl ammonium chloride and tetrabutyl ammonium chloride or bromide are used. The phase transfer catalyst content is generally between 0.01n and 1% by weight of compound of formula (I), n being the total number of

alcohol functions to esterify.

  At the end of the reaction, the reaction medium containing the compound of formula (II B) may, if appropriate, undergo one or more filtration and / or

  washing and / or removing excess solvent or reagent.

- 11 -

  The compound of formula (II B) can be further subjected to purification, for example by distillation, in particular under reduced pressure, by

  chromatography on a silica column or by recrystallization.

  D - Preparation of compounds of formula (III) The compounds of formula (III) can be prepared according to two embodiments. In the first mode, the compound of formula (IIA) is subjected to

acylation reaction.

  More specifically, the process consists in reacting: the compound of formula: ## STR1 ## in which Z, R 1, R2, R3, X, m, n and bridge the meaning given above, and an acylating agent of formula:

R-C-R8 (IX)

we

  in which R and R8 have the meaning given above.

  The conditions of the reaction are the same as those described above for the preparation of the compounds of formula (II B). The value of the weight ratio or the molar ratio shall be understood as referring to the compound of formula

(I1 A).

  The reaction can be carried out in the absence of any basic compound, i.e.

  say of a base, a solvent or a basic precursor. In this case, an exchange of contrion is likely to intervene partially or totally. Thus, starting from an acid chloride, the compound of formula (III) obtained will be in methane form

  sulfate, chloride or a mixture of these two forms.

  In the second embodiment, the compound of formula (II)

  B) to a quaternization reaction.

  More specifically, the process consists in reacting: the compound of formula: ## STR2 ## in which Z, R, R 1, R 2, m, n and p the meaning given above, and a quaternization agent of formula:

R3X (VIII)

  in which R3 and X have the meaning given above.

  The conditions of the reaction are the same as those described above for the preparation of the compounds of formula (11A). The value of the weight ratio or the indicated molar ratio shall be understood as referring to the

formula (11 B).

  At the end of one or the other of the aforementioned embodiments, the compound of formula: n [R] -MZ [NH] CHCH2> pN-R2O6 (III) m -M R3 E Preparation of the compounds of formula (IV) The preparation process consists in reacting: the compound of formula: ## STR2 ## in which Z, R, R 1, R 2, m, n and p have the meaning given above, and a compound of formula: Y- (CH 2) r -CO-O -R 11 (X)

  wherein R11 represents a hydrogen atom or an alkali metal, Y represents

  a halogen atom, preferably Cl or Br, and r has the meaning given above, in a solvent chosen from water, C 1 -C 6 alcohols and hydroalcoholic mixtures, to form betaine of formula: -13 ## STR1 ## The molar ratio of the compound of formula (II B) to the compound of formula (X) is generally between 1: 0. , 95n and 1: 10n, preferably 1: 1n and 1: 2n, where n is the number of tertiary amine functions to betain. The amount of solvent is generally chosen so as to obtain a final betaine concentration of between 1 and 50%, preferably 5 and 40%.

  the total weight of the solution or the dispersion obtained at the end of the reaction.

  The process is generally carried out at a temperature of

  between 20 and 110 C, preferably 60 and 100 C. The pH of the reaction medium is generally

  preferably maintained between 6 and 11, preferably 6.5 and 8, for example by means of an alkaline hydroxide such as sodium or potassium hydroxide, preferably in aqueous solution whose concentration is between 30 and 50% in weight. The reaction can be carried out in the presence of a salt resulting from the combination of a halide ion and an alkaline ion, for example KI, and / or a transfer catalyst.

  phase, for example tetrabutyl ammonium bromide.

  The duration of the reaction can vary from 1 to 24 hours, preferably 2 and

12 hours.

  The betaine of formula (IV) thus formed can be used as it is or undergo one or more subsequent treatments, for example a concentration step (removal of the solvent under reduced pressure, lyophilization, etc.) or a purification step (filtration of salts formed or added to facilitate precipitation,

  chromatography on a silica column, ...).

  F - Preparation of compounds of formula (V) The preparation process consists of reacting: the compound of formula: ## STR2 ## in which Z, R 2 , R1, R2, m, n and p have the meaning given above, and an oxidizing agent, in a solvent chosen from water, C 1 -C 6 alcohols and hydroalcoholic mixtures,

- 14 -

  optionally in the presence of a complexing agent to form the compound of formula: ## STR1 ## example of the oxidant, mention may be made of hydrogen peroxide and

  compounds generating hydrogen peroxide. Hydrogen peroxide is preferred.

  Hydrogen peroxide is generally used in the form of an aqueous solution having a concentration by weight of between 5 and 70%, preferably

8et60%.

  The molar ratio of the compound of formula (II B) to the oxidant is generally

  between 1: 0.95n and 1: 1.25n, preferably 1: 1n and 1: 1.15n, n being the

  total number of amine functions to N-oxyder.

  The preferred solvent for the reaction is water.

  The amount of solvent used is generally chosen so as to obtain a final concentration of compound of formula (V) of between 1 and 50%, preferably 5 and 35% of the total weight of the solution or dispersion obtained at the end.

of reaction.

  The complexing agent is generally chosen from carboxymethyl amine derivatives, such as nitrilotriacetic acid (NTA) and ethylenediamine tetraacetic acid (EDTA), alpha hydroxy carboxylic acids such as those defined above by Z , more particularly glycolic acid, lactic acid, malic acid, tartaric acid and citric acid, and acids

  dicarboxylic acids such as succinic acid and maleic acid.

  EDTA and alpha hydroxy carboxylic acids are preferred.

  The weight ratio of the complexing agent to the compound of formula (II B) is

  generally between 10-2n: 1 and 10-5n: 1, preferably 10-3n: 1 and 10-4n: 1. The process is generally carried out at a temperature of

  between 20 and 100 ° C., preferably 50 and 90 ° C.

  The pH of the reaction medium is maintained between 6 and 10, preferably 6 and 9, for example by means of an alkaline hydroxide such as sodium or potassium hydroxide, preferably in aqueous solution, the concentration of which is

between 30 and 50% by weight.

  The reaction is conducted at atmospheric pressure. We can possibly

  operate under an inert atmosphere, eg under argon or nitrogen.

- 15 -

  The duration of the reaction can vary from 0.5 to 24 hours, preferably 1 to

12 hours.

  The compound of formula (V) thus formed can be used as it is or undergo a complementary stage of concentration of the solvent, for example by evaporation under reduced pressure or by lyophilization, or a purification step, for example by chromatography on a silica column. The compounds of formula (I), (II A), (II B), (III), (IV) and (V) thus obtained have properties of washing and / or conditioning of the skin and the hair.

  The following examples illustrate the invention. In these examples

  the following methods of analysis are used.

  Thin layer chromatography The RF is measured by silica thin layer chromatography (Alugram, # 818133, MACHEREY-NAGEL). The migration solvent is methanol and the migration spots are revealed by spraying with a solution of

  ninhydrin at 0.5% in n-butanol and heating at 120 ° C. for 2 minutes.

  Nuclear Magnetic Resonance (NMR) Spectra are made using a BRUCKER AC

  multinucleus at 200.13 MHz (1H) and 50.32 MHz (13C) in deuterated chloroform

  for the compounds of formula (I), (IIB) and (III), in deuterated dimethyl sulphoxide for the compounds of formula (IIA) and in deuterated methanol for

compounds of formula (IV) and (V).

  The internal reference is tetramethylsilane. Chemical shifts

* are expressed in ppm.

  Infrared Spectrography (IR) The spectra are made using a PERKIN ELMER 1720X Fourier transform apparatus, on a film between two NaCl pellets for the compounds

  liquid or dispersion in KBr (2% pellet) for solid compounds.

  Values are expressed as a number of waves per centimeter.

Melting temperature

  It is measured on a BOCHI device, and expressed in C (not corro-

  EGE). Surface tension of water (Y) The surface tension of water is measured by tensiometry according to ISO 304 modified in that the dimensions of the rectangular plate are 25 mm x mm x 0.1 mm. The surface tension is expressed in mN / m. Foaming Power The foaming power is measured by bubbling nitrogen at a constant rate (100 ml / min.) Through a sinter (water permeability: 60 ml / h at atmospheric pressure) placed at the base of the a graduated cylinder (320 mm x 70 mm) and thermostated containing 100 ml of aqueous solution of surfactant. The foaming power is defined by the minimum concentration of surfactant which makes it possible to produce a volume of

400 ml foam.

  EXAMPLES 1 to 5: Preparation of the compounds of formula (I) (p = 3, R1 =

R2 = CH3)

  In a 1-liter reactor, 1 mole of alpha-hydroxy acid alkyl ester is introduced as follows: ethyl glycolate (104.11 g, reference 36, 484-3, ALDRICH): example 1 - ethyl lactate (118.13 g, Ref E3,410-2, ALDRICH): Example 2 - dimethyl malate (162.14 g, reference 37, 431-8, ALDRICH): Example 3 - diethyl tartrate (206.19) Ref # 21,396-9 ALDRICH): Example 4 - Triethyl citrate (276.29 g, Ref 10.929-0, ALDRICH): Example 5 - and 3-dimethylaminopropylamine (Ref D14,500; ALDRICH) 1.5 moles (188.75 ml, 153.27 g): Examples 1 and 2 - 3 moles (377.51 ml, 306.54 g): Examples 3 and 4 - 4.5 moles (566, 27 ml, 459.81 g): Example 5

  After 24 hours (Examples 1, 2 and 4) or 72 hours (Examples 3 and 5) of agonist

  at 25 ° C., the compound of formula (I) is recovered by concentration under

  reduced pressure (2.4 kPa / 30 C, then 2.4 kPa / 60 C and 7 Pa / 60 C).

  The compounds according to Examples 1, 2 and 4 are purified by distillation

  (Examples 1 and 2) and by recrystallization (Example 4).

  The characteristics of this compound are given below: * Example 1: N (3-dimethylaminopropyl) glycolamide - Yield: 91.7% - Melting point: 54-55 ° C (hexane) - Distillation: 155-160 ° C. 7 Pa

  IR: 3293, 2947, 1652, 1539, 1464, 1263, 1159, 1079, 1040, 822

- NMR

2 1 3 4 5 CH3

HO-CH2-C-NH-CH2-CH2-CH2-N '

o CH3

  1H: 7.46 (NH); 6.05 (OH); 3.95 (H2); 3.28 (H3); 2.29 (H5); 2.16 (H6);

1.64 (H4)

  13c: 172.703 (Cl); 61.951 (02); 57.172 (C5); 45.159 (C6); 37.338

(03); 26.895 (04).

  Example 2: N- (3-dimethylaminopropyl) lactamide - Yield: 91.9% Distillation: 144-148 ° C at 7 Pa

  IR: 3299, 2942, 2861, 2776, 1656, 1533, 1463, 1366, 1314, 1263,

1157, 1126, 1075, 1041, 972, 843

- NMR

2 1 4 5 6 CH3

HO-CH-C-NH-CH2-CH2-CH2 - N

3 CH3 0 CH3

  1H: 7.50 (NH); 5.13 (OH); 4.13 (H2); 3.28 (H4); 2.33 (H6); 2.20 (H7);

1.67 (H5); 1.35 (H3)

  13c: 175.395 (Cl); 67.774 (C2); 57,101 (06); 45.036 (07); 37.379

(04); 26.720 (05); 21.095 (03).

  * Example 3: N- (3-dimethylaminopropyl) malamide - Yield: 81.4%

  IR: 3304, 3084, 2944, 2862, 2819, 2779, 2361, 1708, 1651, 1538,

  1464, 137, 1309, 1264, 1183, 1101, 1040, 975, 839.

NMR

2 1 5 6 7 / CH3

HO-CH-C - NH-CH2 - CH2-CH2-N

O CH3

4 CH3

3 CH2-C-NH-CH2-CH2-CH2-N

o 5 6 7 CH3

  1H: 7.68 (NH); 4.31 (H2); 3.27 (H5); 2.44-2.72 (H3); 2.26-2.35 (H7);

2.18 (H8); 1.63 (H6)

  13c: 173.019 (Cl); 171, 759 (04); 69.306 (02); 57.657 (07); 45.384

  (08); 39.295 (03); 38.009 (05); 26.924 (06).

  Example 4: N- (3-dimethylaminopropyl) tetraamide - Yield: 71.3% Melting point: 19-120 ° C (ethyl acetate)

  IR: 3304, 3084, 2944, 2862, 2819, 2779, 2361, 1708, 1651, 1538,

  1464, 137, 1309, 1264, 1183, 1101, 1040, 975, 839.

- NMR

- 18 -

2 1 5 6 7 CH3

HO CH C NH CH2 CH2 CH2 N

O CH3

1 CH3

HO CH -C-NH-CH2 -CH2 --- CH2 -N

2 O 5 6 7 CH3

  1H: 7.70 (NH); 6.6-6.5 (OH); 4.41 (H2); 3.24 (H5); 2.26 (H7); 2.12 (H8)

  13c: 173.029 (01); 72.208 (02); 57,342 (07); 45.247 (08); 37.835

(05); 26.912 (06).

  Example 5: N- (3-dimethylaminopropyl) citramide - Yield: 95%

  IR: 3301, 3102, 2945, 2764, 1653, 1539, 1461, 1373, 1262, 1186,

1100, 1041, 975, 908, 842.

NMR

2 1 5 6 7 CH3

CH 2 -C-NH-CH 2 -CH 2 -CH 2 -N

0 12 CH3

O 12 3 4 9 10 1l CH3

HO - C-C-NH-CH 2 -CHH 2 -CH 2 -N

O CH3

1 5 6 7 CH3

2 CH 2 -C-NH-CH 2 -CH 2 -CH 2 -N

0 CH3

8

  1H: 7.80 (NH-09); 7.56 (NH-C5); 3.17 (H5 + H9); 2.65-2.42 (H2); 2.24

  (H7 + H11); 2.13-2.12 (H8 + H12); 1.56 (H6 + H10).

  13c: 173.855 (04); 170.574 (01); 75,383 (03); 57.852 (07); 57.768

  (011); 45.522 (012); 45.415 (08); 42.795 (02); 38.470 (05 + C9); 26.718

(C10); 26.606 (06).

  EXAMPLES 6 to 9: Preparation of the compounds of formula (11A) (p = 3,

R1 = R2 = R3 = CH3, X = CH3OSO3)

  In a 500 ml reactor, 0.1 mole of the alpha hydroxycarbonate is introduced.

  Boxamide of formula (I) according to Example 1 (16.3 g): Example 6 Example 2 (17.5 g): Example 7 - Example 3 (30.3 g): Example 8 Example 4 (31.9 g): Example 9 -19 ml of anhydrous dichloromethane and dropwise, with stirring of dimethyl sulphate (Ref D18.630-9, ALDRICH): -0.11 mol (10, 40 ml, 13.87 g): Examples 6 and 7 - 0.22 moles (20.81 ml, 27.75 g): Examples 8 and 9 After two hours of stirring at 25 ° C., the biphasic reaction medium obtained - Naked is decanted and the oily residue minority (upper phase in Examples 6, 7 and 8, lower phase in Example 9) is washed with chloroform (by trituration) and then concentrated under vacuum (2.4 kPa / 50C; examples 6 and 7) or taken up with 1 ml of methanol, concentrated under vacuum (2.4 kPa / 30 ° C.), taken up again with 200 ml of dichloromethane, decanted and concentrated again under vacuum

(2.4 kPa / 50 C - Examples 8 and 9).

  The compound of formula (11A) which has the following characteristics is recovered:

  Example 6: N- (3-trimethylammoniumpropyl) glycol

mide - Yield: 85%

  IR: 3359, 2949, 1669, 1541, 1482, 1345, 1226, 1059, 1009, 913, 755,

667, 610

- RIMN

2 1 3 4 5 e) 3

  HO-CH2-C-NH-CH2-CH2-CH2-N-CH3 CH3OSO3

O CH3

  1H: 7.90 (NH); 3.81 (H2); 3.41 (H7); 3.28 (H5); 3.25 (H3); 3.05 (H6);

1.86 (H4)

  Example 7 N- (3-trimethylammoniumpropyl) lactamide methyl sulfate Yield: 80%

  IR: 3360, 2950, 1652, 1539, 1483, 1370, 1250, 1222, 1125, 1060,

-RMN CH3 2 1 4 5 6 C 8 e

  HO-CH-C-NH-CH 2 -CH 2 -CH 2 -N - CH 3 CH 3 OSO 3

3 CH3 0 CH3

  1H: 7.86 (NH); 5.43 (OH); 3.98 (H2); 3.43 (H8); 3.29 (H6); 3.16 (H4);

3.07 (H7); 1.87 (H5); 1.23 (H3)

  Example 8 N- (3-trimethylammoniumpropyl) malamide methyl sulfate Yield: 75%

  IR: 3323, 3039, 2950, 2836, 1651, 1538, 1485, 1368, 1224, 1059,

1009, 971, 915, 755, 611, 580.

- NMR

- 20 -

2 1 5 6 7 ECH3 9

  HO CH C NH CH2 CH2 CH2 N CH3 CH3OSO3

0 CH3

4 th CH3 9

  3 CH2 - C-NH-CH2-CH2-CH2-N-CH3 CH3OSO3

o 5 6 7 \ CH

O CH3

  1H, 7.98; 7.95 (NH); 5.69 (OH); 4.23 (H2); 3.41 (H9); 3.26 (H7); 3.14

  (H5); 3.05 (H8); 2.49; 2.37 (H3); 1.85 (H6).

  13C: 173.589 (Cl); 170.143 (C4); 68,557 (C2); 63.340 (C7); 52.989

  (C9); 52.14 (C8); 40.713 (C3); 35.397; 35.266 (C5); 22.829 (C6).

  Example: N- (3-trimethylammoniumpropyl) tartramide methyl sulfate Yield: 60%

  IR: 3347, 3041, 2950, 1651, 1539, 1487, 1256, 1134; 1060, 1008,

914, 821,760.

- NMR

2 1 5 6 7 E CH3 9 th

  HO-CH-C-NH-CH2-CH2-CH2-N-CH3 CH3OSO3

O CH3

6 7 E / CH3 9 e

  HO-CH-C-NH-CH 2 -CH 2 -CH 2 -N-CH 3 CH 3 OSO 3

O o8 CH3

  1H: 7.95 (NH); 5.63 (OH); 4.26 (C2); 3,405; 3,400 (C9); 3.23 (C7);

3.16 (C5); 3.04 (C8); 1.87 (C6).

  13C: 172.248 (C1); 72.785 (C2); 63.456 (C7); 52.891 (C9); 52.213

(C8); 35.273 (C5); 22.896 (C6).

  EXAMPLES 10 to 12: Preparation of the compounds of formula (LiB) (p = 3,

R1 = R2 = CH3)

  A - Process using an acyl chloride

  a- preparation of O-dodecanoyl N- (3-dimethylaminopropyl) glycola-

  mide (Example 10) 0.1 mol of the alpha hydroxy carboxamide according to Example 1 (16.3 g), 350 ml of chloroform, 0.13 mol (17.96 g) are introduced into a 1-liter reactor. ) of potassium carbonate (Ref 20.9619, ALDRICH) and dropwise 0.12 mole

  dodecanoyl chloride (26.26 g, reference 15,693-0, ALDRICH).

  After stirring for 8 hours at 25 ° C., the reaction medium is filtered through glass.

  sintered n 3 and the filtrate is washed successively with an aqueous solution of hydrogen

  10% by weight sodium bicarbonate (80 ml x 3) and water (80 ml x 3).

-21 -

  The organic phase is recovered and dried (anhydrous magnesium sulphate

  dre), and concentrated (2.4 kPa / 40 C) and purified by distillation.

  O-dodecanoyl N- (3-dimethylaminopropyl) glycolamide having the following characteristics is recovered: - Yield: 63% - Distillation: 190-200.degree. C. under 7 Pa

  IR: 3302, 3084, 2931, 2856, 2817, 2767, 1749, 1669, 1540, 1465,

1378, 1262, 1157, 1115, 1041, 722

-RMN6

2 1 3 4 5 CH3

0 - CH 2 -C - NH-CH 2 -CH 2 -CH 2 -N

JO CH3

1 '2 3 4 5 6 7 8 9 10 1 1 12

  <O.C-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH3

  1H: 7.45 (NH); 4.49 (H2); 3.35 (H3); 2.36 (H5); 2.31 (H2 '); 2.19 (H6);

  1.63 (H4); 1.60 (H 3 '); 1.32 (H4 '); 1.21 (H5'-H11 '); 0.83 (H12 ')

  13C: 172.286 (C1 '); 167.070 (C1); 62.871 (C2); 58.876 (C5); 45.450

  (C6); 39.296 (C3); 33.974 (C2 '); 31.893 (C10 '); 29.577; 29.428 (C6'-C8 ');

  29.308; 29.246 (C5 '+ C9'); 29.147 (C4 '); 25.668 (C4); 24.788 (C3 '); 22, 665 (C11 ');

14.088 (C12 ').

  b- preparation of O-alkanoyl N- (3-dimethylaminopropyl) lactamide

(Examples 11 and 12).

  The procedure of Example 10 modified above is carried out in that the alpha hydroxy carboxamide according to Example 2 (17.5 g), undecenoyl chloride (24.33 g; 16, 166-7, ALDRICH, Example 11) or oleoyl chloride (36.11 g, Ref 36.785-0, ALDRICH, Example 12) and shaken for

16 hours to 30 degrees C.

  The O-alkanoyl N- (3-dimethylaminopropyl) lactamide recovered has the following characteristics: * Example 1 1: O-undecenoyl N- (3-dimethylaminopropyl) lactamide - Yield: 71.6% - Distillation: 200-210 ° C under 134 Pa

  IR: 3306, 2980, 2930, 2859, 2818, 2767, 1743, 1664, 1536, 1460,

  1372, 1242, 1160, 1100, 1041, 995, 910, 862.

- NMR

- 22 -

2 1 4 5 6 CH3

O CH C NH-CH 2 CH 2 -CH 2 -N

3CH CH30 CH3

1 2 3 4 5 6 7 8 9 10 '1 1

  C CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH CH2

O

  1H: 7.63 (NH); 5.81 (H10 '); 5.20 (H2); 4.94 (H11 '); 3.36 (H4); 2.40

  (H6); 2.36 (H2 '); 2.24 (H7); 2.04 (H9 '); 1.67 (H5); 1.64 (H3 '); 1.45 (H3); 1.30

(H4'-H8 ').

  13C: 172.274 (C1 '); 170.413 (C1); 139.115 (C10 '); 114.191 (Cl ');

  357 (C2); 58.842 (C6); 45.461 (C7); 39.306 (C4); 34.306; 33.769 (C9 +)

  C2 '); 29.274; 29.199; 29.104; 29.034; 28.877 (04'-C8 '); 25.754 (C5); 24, 838

(C3 '); 18.062 (C3).

  Example 12: O-oleoyl N- (3-dimethylaminopropyl) lactamide - Yield: 83% - Distillation: 200-220 C under 7 Pa

  IR: 3309, 2927, 2854, 1744, 1666, 1536, 1461, 1374, 1260, 1100,

1041, 863, 722

- NMR

2 1 4 5 6, CH3

O-CH-C-NH-CH 2 -CH 2 -CH 2 -N

3 CH3 0 CH3

11 2 3 4 5 6 7 8 9

  O, .C-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH

CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH

18 17 16 15 14 13 12 11 10 '

  1H at 7.62 (NH); 5.35 (H9 + H10); 5.20 (H2); 3.37 (H4); 2.41 (H6): 2.37

  (H2 '); 2.25 (H7); 2.10 (H8 + H11); 1.68 (H5); 1.65 (H3 '); 1.46 (H3); 1, 31-1.27

(H4'-H7 ', H12'-H17'); 0.88 (H18 ').

  13C: 172.223 (C1 '); 170.401 (C1); 130.018; 129.675 (C9 '+ C10');

  70,298 (C2); 58.643 (C6); 45.326 (C7); 34.245 (C2 '); 39.14 (C4); 31.875

  (C16 '); 29.731; 29.655; 29.490; 29.285; 29.149; 29.066 (C4'-C7 ', C12'C15');

  27.188; 27.124 (C8 '+ C11'); 25.707 (C5); 24.803 (C3 '); 22.646 (C17 '); 18, 009

(C3); 14.074 (C18 ').

  B - Method Using a Methyl Ester In a 100 ml reactor equipped with a mechanical stirring device, a descending condenser, a 50 ml recovery flask, 34.435 mmol (6 g) of the alpha hydroxy carboxamide according to Example 1, 169.65 mmol (33.7 g, 37.8 ml, 4.92 molar equivalents) of

- 23 -

  methyl (ELF ATOCHEM), 34.73 mmol (4.8 g) of potassium carbonate and 0.219 mmol (88.4 mg, 0.1 ml) of tricapryl methyl ammonium chloride (Aliquat

33; Ref. 20.561 to 3; Aldrich).

  After partial evacuation (2.4 kPa), the reaction medium is heated at 100 ° C. for 24 hours, filtered on a cake of celite and concentrated under vacuum.

(0.9 kPa / 95 C).

  The residue is chromatographed on a silica column (230-400 Mesh

  ASTM; eluent: ethyl acetate then methanol).

  O-undecenoyl N- (3-dimethylaminopropyl) lactamide is recovered in a yield of 85.3%. This compound has the same characteristics as

Example 1 1.

  EXAMPLES 13 to 16: Preparation of compounds of formula (III) (p = 3, R 1 = R 2 = R 3 = CH 3 and X = CH 3 OSO 3 or CH 3 OSO 3 / Cl) A - By acylation of a compound of formula (1 / A) In a 100 ml reactor is charged with 0.01 mol (3 g) of N- (3-trimethylammoniumpropyl) lactamide methyl sulfate according to Example 7 and 0.012 mol of

  dodecanoyl chloride (2.62 g, 2.78 ml, 15.993-0, ALDRICH).

  After stirring for 72 hours at 25 ° C., 100 ml of chloroform is added to the reaction medium and the mixture is filtered on n-3 sintered glass. The filtrate is concentrated under vacuum (2.4 kPa / 40 ° C.) and the residue is purified by chromatography. fast on a column

  silica (230-400 Mesh ASTM, eluent: methanol).

  Methyl sulfate / O-dodecanoyl chloride N- (3-trimethylammoniumpropyl) lactamide (Example 8), which is predominantly in the form of chloride, is recovered, the complementary counterion being the methylsulphate form. This compound has the following characteristics: Yield: 65%

  IR: 3294, 2920, 1733, 1668, 1548, 1484, 1467, 1374, 1102, 1042, 969

NMR

2 1 4 5 6 CH3 8 G

  O-CHC-NH-CH 2 -CH 2 -CH 2 -N-CH 3 CH 3 OSO 3 Cl

3 CH3 0 CH3

  C-CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 3

0 2 3 4 5 6 7 8 9 10 '1i' 12

0

  1H: 8.62 (NH); 4.99 (H2); 3.53 (H6); 3.39 (H8); 3.31 (H4); 3.21 (H7);

  2.34 (H2 '); 2.02 (H5); 1.56 (H3 '); 1.23 (H4'-H11 '); 1.42 (H3); 0.85 (H12 ').

  13C: 173.700 (C1 '); 171.966 (C1); 70,390 (C2); 64.321 (C6); 53.174

  (C7); 50, 290 (C8); 36.004 (C4); 34.212 (C2 '); 31.934 (C10 '); 29.671; 29, 571;

- 24 -

  29.369; 29.218 (C4'-C9 '); 24.967 (03 '); 23.043 (05); 22,700 (C11 '); 17, 914 (03);

14.118 (012 ').

  B - By quaternization of a compound of formula (IB) a - preparation of O-dodecanoyl methyl sulfate N- (3-trimethylammonium propyl) glycolamide (Example 14)

  In a 100 ml reactor, 0.01 mole (3.41 g) of O-dodecane is introduced.

  canoyl N- (3-dimethylammoniumpropyl) glycolamide according to Example 10, 50 ml of dichloromethane and, dropwise with stirring, 0.012 mol (1.08 ml, 1.51 g) of

dimethyl sulfate.

  After stirring for 6 hours at 30 ° C., the reaction medium is concentrated

(101.325 kPa / 40 C and 67 Pa / 70 C).

  O-Dodecanoyl methyl sulfate N- (3-trimethylammonium) is recovered.

  nium propyl) glycolamide having the following characteristics: Yield: 62%

  IR: 3359, 2949, 1669, 1541, 1482, 1345, 1226, 1059, 1009, 913, 755,

667, 610.

- NMR 2 1 3 4 5 CH 3 7

* O-CH2-C-NH-CH2-CH2-CH2-N-CH3 CH3OSO3

0 CH3

  C - C, H2-CH2-CH2 -CH2-C, -CH2C H2-CH2 -CH2-CH2-CH2-CH3

// 2 3 4 5 6 7 8 9 10 'il 12 o

  1H 7.71 (NH); 4.48 (H2); 3.90 (H7); 3.61 (H7); 3.44 (H5); 3.31 (H3);

  3.11 (H6); 2.36 (H2 '); 1.99 (H4); 1.54 (H3); 1.25 (H4'-H11 '); 1.18 (H, 5H10 '); 0.80

(H12 ').

  : 173.587 (Cl '); 168.445 (Cl); 62.656 (C2); 64.435 (C5); 54.456

  (07); 53.162 (06); 35.918 (03); 33.896 (02 '); 31,890 (010 '); 29.614; 29, 520;

  (C6 'C8'); 29.321; 29.321 (C 5 + 09 '); 29.154 (04 '); 24.852 (03 '); 23.033 (04);

22.659 (011 '); 14.090 (012 ').

  b- preparation of O-undecenoyl methyl sulfate N- (3-trimethylammoniumpropyl) lactamide (Example 15) The procedure of Example 14 modified above is carried out in that O-undecenoyl N is used. - (3-dimethylaminopropyl) lactamide according to

Example 11.

  The O-undecenoyl methyl sulfate N- (3-trimethylammoniumpropyl) lactamide obtained has the following characteristics: Yield: 70%.

  IR: 3480, 2927, 2856, 1738, 1673, 1546, 1483, 1462, 1388, 1225,

1101, 1061, 1009, 912, 831, 756.

-RMN CH3

2 1 4 5 6 CH3 8

  O-CH-C-NH-CH 2 -CH 2 -CH 2 -N-CH 3 CH 3 OSO 3

3 CH30 CH3

  C-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH = C, H2

O 2 3 4 5 6 7 8 9 10 11

  1H: 7.77 (NH); 5.80 (H10 '); 4.96 (H2 + H11 '); 3.68 (H8); 3.47 (H6);

  3.28 (H4); 3.18 (H7); 2.39 (H2 '); 2.03 (H5 = H9 '); 1.57 (H3 '); 1.28 (H4'H8 '); 1.43

  (H3). 13c: 173.649 (Cl '); 172.165 (Cl); 139.154 (C10 '); 114.207 (C11 ');

  70.454 (C2); 64.430 (C6); 54.641 (C8); 53.221 (07); 35.853 (C4); 34.10; 33.790

  (C2 '+ C9'); 29.344; 29.258; 29.117; 29.084; 28.910 (C4'-C8 '); 24.880 (03 ');

23.080 (05); 17.739 (03).

  c- preparation of O-oleoyl methyl sulfate N- (3-trimethylammonium propyl) lactamide (Example 16) The procedure of Example 14 modified above is carried out in that O-oleoyl N is used. - (3-dimethylaminopropyl) lactamide according to Example 12, 0.015 mol (1.36 ml, 1.89 g) of dimethyl sulfate and that the reaction medium is

stirred for 48 hours at 40 C.

  O-Oleoyl methyl sulfate N- (3-trimethylammonium propyl) lactam

  mide obtained has the following characteristics: - Yield: 68%

  IR: 3302, 2921, 1740, 1671, 1546, 1466, 1374, 1217, 1008, 969, 853,

752.-RMN CH3

2 1 4 5 6 CH3 8

  OO-CH-C-NH-CH 2 -CH 2 -CH 2 -N-CH 3 CH 3 OSO 3

3 CH30 CH3

2 3 4 5 6 7 8

  C --H2 H2- CH2 -CH2-CH2-CH2- - H2

 0 g9 'CH l0' CH

H3C-CH2-CH2-CH2-CH2-CH2-CH2-CH2

18 17 16 15 14 13 12 11l

- 26 -

  1H: 7.83 (NH); 5.26 (H9 + H10); 4.94 (H2); 3.67 (H8); 3.42 (H6); 3.25

  (H4); 3.11 (H7); 2.35 (H2 '); 2.1-1.9 (H5 + H8 + H11).

  EXAMPLES 17 to 21: Preparation of the compounds of formula (IV) (p = 3, r = 1 and R1 = R2 = CH3) In a 100 ml three-necked flask equipped with a magnetic stirrer, a

  pH probe, an ascending condenser, 20 mmol of O-acyl N- (3-

  dimethylaminopropyl) carboxamide of formula (II B) identified as follows: O-undecenoyl N- (3-dimethylaminopropyl) glycolamide (6.53 g) prepared under the conditions of Example 11 modified in that one uses the alpha hydroxy carboxamide of Example 1: Example 17 - O-dodecanoyl N- (3-dimethylaminopropyl) glycolamide (6.85 g) according to Example 10: Example 18 - O-undecenoyl N- (3-dimethyl) aminopropyl) lactamide (7.10 g) according to Example 11: Example 19 - O-dodecanoyl N- (3-dimethylaminopropyl) lactamide (7.13 g) prepared under the conditions of Example 10 modified in that the alpha hydroxy carboxamide of Example 2 is used: Example 20 - O-oleoyl N- (3-dimethylaminopropyl) lactamide of Example 12: Example 21 30 ml of demineralized water are then introduced and the mixture is heated the middle

  Reaction at 75 ° C. 21 mmol (2.45 g) of sodium chloroacetate (Ref.

  29.113 to 7; ALDRICH) and the medium is heated at 90 ° C. for 7 hours.

  The solution is lyophilized and betaine of formula (IV) is recovered.

  The characteristics of betaine are presented below:

  Example 17: O-undecenoyl N- (3-dimethyl ammonium methane carboxy-

  late propyl) glycolamide - Yield: 75% -RMN CH37E 2 1 3 4 5 C H7 8 e

O-CH2-C-NH-CH2-CH2-CH2-N-CH2 -CO2

O CH3

  C-CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 CH 2 -CH-CH 2

'2 3 4 5 6 7 8 9 10' 11 '

O

  1H: 4.96 (HCl); 5.81 (H10 '); 4.56 (H2); 3.83 (H7); 3.64 (H5); 3.34 (H3);

  3.26 (H6); 2.47 (H2 '); 2.05 (H9 '); 2.00 (H4); 1.64 (H3 '); 1.33 (H4'-H8 ').

- 27 -

  : 176.447 (01 '); 172.212 (01); 170.416 (C8); 141.714 (010 '); 116.336

  (C11 '); 66.630 (07); 65,206 (02); 65,010 (05); 53.439 (06); 38.646 (03); 36.462

  (09 '); 36.196 (02 '); 32.005; 31.951; 31.852; 31.744; 31.678 (04'-08 '); 27.417

(03 '); 25.734 (04).

  Example 18: O-dodecanoyl N- (3-dimethylammonium methane carboxyl propyl) glycolamide Yield: 74%

- NMR

CH3 2 1 3 4 5 eCH37 8 th

O-CH2-C-NH-CH2-CH2-CH2-N-CH2-CO2

O CH3

  CC - C HH2CH2 - C H2 -CH2-C CH2-CHH2-CH2-CH2-CH2-CH2-CH3

// 2 3 4 5 6 7 8 9 10, 1il 12

  1H: 4.55 (H2); 3.81 (H7); 3.62 (H5); 3.34 (H3); 3.25 (H6); 2.46 (H2 ');

  1.98 (H4); 1.65 (H3 '); 1.30 (H4'-H11 '); 0.91 (H12 ').

  13C: 174.779 (01 '); 170.570 (C1); 168.781 (C8); 64.874 (C7); 63.527

  (02); 63,290 (C5); 51.593 (C6); 36.958 (C3); 34,530 (C2 '); 33.019 (C10 ');

  , 693; 30.588; 30.573; 30.422; 30.391 (C, 5'-09 '); 30.143 (C4 '); 25.778 (C3 ');

  24.070 (C4); 23.690 (011 '); 14.435 (012 ').

  Example 19: O-undecenoyl N- (3-dimethyl ammonium methane carboxy

  late propyl) lactamide - Yield: 85%

- NMR

2 1 4 5 6 o CH38 9

O-CH-C-NH-CH2-CH2-CH2-N-CH2-CO2

3 CH3 O CH3

  C-CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 CH 2 -CH 2 CH 2 CH 2 -CH = CH 2

O / 2 3 4 5 6 7 8 9 10 '11il 2

  1H: 5.80 (H10 '); 4.97 (H2); 4.95 (H11 '); 3.82 (H8); 3.61 (H6); 3.32 (H4);

  2.42 (H2 '); 2.02 (H9 '); 1.99 (H5); 1.61 (H3 '); 1.43 (H3); 1.32 (H4'-H8 ').

  13C: 174.655 (C1 '); 173.862 (C1); 168.648 (C9); 139.940 (C10 '); 114.723

  (C11 '); 71.529 (C2); 64.964 (C8); 63.309 (C6); 51.660 (C7); 36.881 (C4); 34.738

  (C9 '); 34.669 (C2 '); 30.288; 30.222; 30.016; 30.016 (C5'-C8 '); 29.941 (C4 ');

  720 (C3 '); 23.990 (C5); 18.050 (C3).

- 28 -

  EXAMPLE 20 O-Dodecanoyl N- (3-dimethyl ammonium methane carboxy)

  late propyl) lactamide - Yield: 83%

- NMR

2 1 4 5 6 0CH38 9

O-CH - C-NH-CH 2 -CH 2 -CH 2 -N-CH 2 -CO 2

3CH30 CH3

  C-CH2-CH2-CH2-C, H2-C, H2-CH2-CH2-CH2-CH2-CH2-CH3

2 3 4 5 6 7 8 9 10 11il 12

O

  1H at 4.96 (H2); 3.81 (H8); 3.60 (H6); 3.31 (H4); 3.25 (H7); 2.42 (H2 ');

  1.98 (H5); 1.62 (H3 '); 1.43 (H3); 1.29 (H4'-H11 '); 0.89 (H12 ').

  13C: 176.483 (C1 '); 175, 706 (C1); 170.395 (C9); 73, 294 (C2); 66.638

  (C8); 65.060 (C6); 53.405 (C7); 38.612 (C4); 36.408 (C2 '); 34.668 (C10 ');

  32.336; 32.336; 32.218; 32.066; 32.024 (C5'-C9 '); 31.790 (C4 '); 27.474 (C3 ');

  738 (C5); 25.340 (C11 '); 19.727 (C3); 16.095 (C12 ').

  Example 21: O-oleoyl N- (3-dimethylammonium methane carboxylate propyl) lactamide - Yield: 86%

- NMR

CH3

2 1 4 5 6 E CH38 9

O - CH-C-NH-CH 2 -CH 2 -CH 2 -N-CH 2 -CO 2

3 CH3 0 CH3

2 '3' 4 '5' 6 '7' 8 '

C-CH2_CH2-CH2-CH2-CH2-CH2-CH2

f / O0 9'g CH 'CH

H3C0-CH2-CH2-CH2-CH2-CH2-CH2-CH2

1817 16 15 14 13 12 11il

  1H: 5.33 (H9 + HO10); 4.97 (H2); 3.82 (H8); 3.60 (H6); 3.31 (H4); 3.25

  (H7); 2.42 (H2 '); 2.02 (H5 + H8 + H11); 1.62 (H3 '); 1.43 (H3); 1.33-1.29 (H4'-H7'-

H12'-H17 '); 0.89 (H18 ').

  13C: 176.405 (C1 '); 175.658 (C1); 170.424 (C9); 132.522; 132.418

  (C9 + C10 '); 73.287 (C2); 66.680 (C8); 65.068 (C6); 53.438 (C7); 38.634 (C4);

  36.445 (C2 '); 34.703 (C16 '); 32.488; 32.466; 32.261; 32.095; 31,995; 31, 865;

  31.823; 31.688; 29.904; 29.804 (C4'-C8 '; C11'-C15')); 27.503 (C3 '); 25, 745 (C5);

  , 386 (C17 '); 19.802 (C3); 16,199 (C18 ').

  EXAMPLE 22 Preparation of a compound of formula (V) (p = 3, R1 = R2

= CH3)

  In a 100 ml three-necked flask equipped with a magnetic stirrer, a dropping funnel, an ascending condenser and a thermometer, mmoles (7.13 g) of O-dodecanoyl N- (3- dimethylaminopropyl) lactamide (prepared under the conditions of Example 10 modified in that the alpha hydroxy carboxamide of Example 2 is used). 20 ml of water, 5 mg of EDTA (Ref E2.628-2, ALDRICH) are then introduced and, with stirring, the reaction medium is heated to 70 ° C. 6.9 g are poured dropwise. an aqueous solution at 10% by weight of

  hydrogen peroxide (0.75 g, 22 mmol) containing 5 mg of EDTA.

  After stirring for 5 hours at 70 ° C., the reaction medium is lyophilized and

  recovering O-dodecanoyl N- (3-dimethylamine N-oxide propyl) lactamide.

  The characteristics of this compound are presented below: - Yield: 70%

- RF = 0.41

-RMN CH3 2 I 4 5 6 CH e

O - CH-C-NH-CH2-CH2-CH2-N -> - O

3 CH3 0 CH3

  C-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH3

O 2 3 4 5 6 7 8 9 10 11 12

  1H: 4.96 (H2); 3.35-3.26 (H4 + H6); 3.16; 3.15 (H7); 2.41 (H2 '); 2.04 (H5);

  1.62 (H3 '); 1.42 (H3); 1.29 (H4'-H11 '); 0.90 (H12 ').

  13c: 174.953 (Cl '); 174,256 (Cl); 71.852 (C2); 69.652 (06); 58.920

  (C7); 37.730 (04); 35.026 (02 '); 33.354 (010 '); 31.016; 31.016; 30.890; 30.751

  , 699; 30.461 (C4'-09 '); 26.126 (03 '); 25.098 (05); 24.019 (C11 '); 18.380 (03);

14,740 (012 ').

- 30 -

  EXAMPLE 23: Lowering the surface tension of water Surface tension (y (mN / m) Example 13 (80 mg / l) 26 (100 mg / l) Example 21 33 (20 mg / l) ORAMIX-NS- 10 26 (330 mg / I) (APG; SEPPIC)

  MIRANOL 33 (200 mg / l) (cocoamphodiacetate; Rhone-Poulenc) GENAPOLZRO 27 (100 mg / l) (30E lauryl ether sulfate; HOECHST) 26 (115 mg / l) EXAMPLE 24 Foaming power Minimum concentration (mg / l) Example 20 40 Example 21 32

ORAMIX-NS-10 40

(APG; SEPPIC)

MIRANOL 65

  (cocoamphodiacetate, Rhone-Poulenc)

- 31 -

Claims (28)

  1. Use as washing and / or conditioning agents for the skin and hair of compounds belonging to the group consisting of: (i) compounds of formula: [H] Z {NH- (CH 2) pN '( In R2 n (ii) compounds of formula: [H] Z- [NH - (CH2) PN - R2 nX (II1A) n R3 (iii) compounds of formula: RC - Z NH- (CH2) pN (II B) 0M R2 n (iv) compounds of formula: RC-Z-NH- (CH2) p -N-R2J nX (III) R3 (v) compounds of formula: RCZ-NH- ( CH2) pN-R2 E (IV) L oj m (CH2) rC-2 n k jm r-   (vi) compounds of formula: ## STR2 ## wherein - 32 -   Z represents the di- or polyvalent residue of an alpha hydroxy carboxylic acid,   R represents an aliphatic chain, linear or branched, saturated or unsaturated   C1-C21, R1, R2 and R3, which may be identical or different, represent a C1-C4 alkyl radical, X represents a halogen atom or a group of formula -SO3-O-R3, R3 having the meaning given above, m is an integer ranging from 1 to 10, n, p and r, identical or different, are integers ranging from 1 to 4. 2. Use according to claim 1, in which the residue Z is chosen from the residues of formula: R4 O ...-- C..C   R5 O in which: R4 and R5, which may be identical or different, represent a hydrogen atom, a C1-C4 alkyl radical, or a radical of formula: CH C-   Wherein R6 is hydrogen or -O-, and t is 0, 1, 2 or 3. 3. Use according to claim 2, wherein Z is selected from   residues of glycolic, lactic, 2-methyllactic, 2hydroxybutanoic acids, 2-   hydroxypentanoic, 2-hydroxyhexanoic, malic, citramalic, tartaric, tartrate nique and citric.   The use according to claim 3, wherein: Z represents an alpha hydroxy carboxylic acid residue selected from   residues of glycolic, lactic, 2-methyllactic, malic, tartaric, tartronic that and citric, - 33 -   R represents a linear or branched, saturated or unsaturated aliphatic chain   C 6 -C 21, R 1, R 2 and R 3, which may be identical or different, represent a methyl, ethyl or propyl radical, R 1 and R 2 being preferably identical, X represents Cl, Br, I or a group of formula - SO 3 O R3, R3 having the meaning defined above, m is an integer ranging from 1 to 8, n is an integer ranging from 1 to 3, pest equal to 3, remains at 1.   5. Use according to one of claims 2 to 4, wherein the radical   R-CO- is selected from octanoyl, decanoyl, 10-undecenoyl, lauroyl,   palmitoyl, stearoyl, oleoyl, eicosanoyl and behenoyl.   6. Compound of formula: R-C] Z NH- (CH2) p -N-R2 nX (111) m n R3s "in which   Z represents the di- or polyvalent residue of an alpha hydroxy carboxylic acid that of formula: R4 -O-C-C--   R5 0 in which: R4 and R5, identical or different, represent a hydrogen atom, a C1-C4 alkyl radical, or a radical of formula: -CH C-   Wherein R6 represents a hydrogen atom or -O-, and t is 0, 1,2 or 3, - 34 -   R represents an aliphatic chain, linear or branched, saturated or unsaturated in Cl-C21,   R1, R2 and R3, which may be identical or different, represent a C1-C6 alkyl radical;   C4, X represents a halogen atom or a group of formula - SO3-O-R3, R3 having the meaning given above, m is an integer ranging from 1 to 10, n and p, which may be identical or different, are integers that can range from 1 to 4. Compounds according to claim 6, wherein Z represents a   residue selected from the residues of glycolic, lactic, 2-methyllactic, 2-   hydroxybutanoic, 2-hydroxypentanoic, 2-hydroxyhexanoic, malic, citrama-   liquefied, tartaric, tartaric and citric.   Compounds according to claim 7, wherein: Z represents an alpha hydroxy carboxylic acid residue selected from   residues of glycolic, lactic, 2-methyllactic, malic, tartaric, tartronic that and citric,   R represents a linear or branched, saturated or unsaturated aliphatic chain   C 6 -C 21, R 1, R 2 and R 3, which may be identical or different, represent a methyl, ethyl or propyl radical, R 1 and R 2 being preferably identical, X represents Cl, Br, I or a group of formula -SO 3 -O- R3, R3 having the meaning given above, m is an integer ranging from 1 to 8, n is an integer ranging from 1 to 3, pest equal to 3.   9. Compounds according to one of claims 6 to 8, wherein the radical   cal R-CO- is selected from octanoyl, decanoyl, undecenoyl,   lauroyl, palmitoyl, stearoyl, oleoyl, eicosanoyl and behenoyl.   10. Compounds of the formula: ## STR2 ## where ## STR2 ## or ## STR1 ## (V) Wherein:   Z represents the di- or polyvalent residue of an alpha hydroxy carboxylic acid than,   R represents an aliphatic chain, linear or branched, saturated or unsaturated   C 1 -C 21, R 1 and R 2, which may be identical or different, represent a C 1 -C 4 alkyl radical, m is an integer ranging from 1 to 10, n, p and r, which may be identical or different, are whole numbers. may vary from 1 to 4. 11. Compounds according to claim 10, in which the residue Z is chosen from the residues of formula: R4 -O-C-c-   i; R5 0 in which: R4 and R5, identical or different, represent a hydrogen atom, a C1-C4 alkyl radical, or a radical of formula: -CH C- -   LR6Jt wherein R6 represents a hydrogen atom or -O-, and t is equal at 0, 1,2 or 3.   12. Compounds according to claim 11, in which Z is chosen from the residues of glycolic acid, lactic acid, 2-methyllactic acid, 2-hydroxybutanoic acid, 2-hydroxypentanoic acid, 2-hydroxyhexanoic acid, malic acid, citramalic acid and tartaric acid. tartronic and citric. - 36 -   Compounds according to claim 12, wherein: Z represents an alpha hydroxy carboxylic acid residue selected from   residues of glycolic, lactic, 2-methyllactic, malic, tartaric, tartronic   Citric acid, R represents a linear or branched aliphatic chain, saturated or unsaturated, C 6 -C 21, R 1 and R 2, identical or different, represent a methyl, ethyl or propyl radical, R 1 and R 2 being preferentially identical, m is an integer ranging from 1 to 8, n is an integer ranging from 1 to 3, pest is 3, remains equal to 1.   14. Compounds according to one of claims 10 to 13, in which the   radical is selected from octanoyl, decanoyl, undecenoyl, lauroyl,   palmitoyl, stearoyl, oleoyl, eicosanoyl and behenoyl.   15. Compositions, in particular cosmetics and capillaries, which comprise NEET:   - (A) at least one compound according to claims 6 and 10, and   - (B) a vehicle compatible with a topical application.   Compositions according to claim 15, wherein the content of   Compound (A) varies from 0.01 to 50% by weight of the composition.   Compositions according to claim 16, wherein the content of   Compound (A) ranges from 0.1 to 30% by weight of the composition.   18. Compositions according to one of claims 15 to 17, in which   the vehicle (B) is water or an organic solvent such as acetone, isopropyl alcohol,   that, the triglycerides of C6-C24 fatty acids, the glycol ethers, the esters of   polyalkylene glycol and C2-C4 acids, and volatile silicones. -37 -   19. Composition according to one of claims 15 to 18 which contains in   in addition to one or more other surfactants and / or additives.   Compositions according to claim 19, wherein the surfactant content can reach 49.99% by weight of the composition. 21. A process for the preparation of the compounds according to claim 6, which comprises reacting: the compound of formula: ## STR2 ## in which Z, R, R 1, R 2, m, n and p have the meaning given above, and a quaternization agent of formula: R3X (VIII)   in which R3 and X have the meaning given above.   22. The method of claim 21, wherein the molar ratio of the compound of formula (II B) to the quaternizing agent of formula (VIII) is understood between 1: 0.80n and 1: 3n.   23. Process for the Preparation of Compounds of Formula: RC-Z NH- (CH2) pN-R2 nX (III) wherein R3 n is the reaction of the compound of formula: [H] Z-NH - (CH2) PN \ R2 nX (11 A) R3 and an acylating agent of formula: R-C-R8 (IX) O   In which formulas in which Z, R, R 1, R 2, R 3, X, m, n and p have the meaning given above, and R 8 represents a halogen atom, a diglyceryl radical whose acyl residues, which are identical or different, contain 2 to 22 carbon atoms, a group -O-C00-R9 in which Rg represents a linear or branched hydrocarbon chain, saturated or unsaturated C1-C21, or a -O-R10 group in which R10   represents a C1-C4 alkyl radical.   24. The method of claim 23, wherein the molar ratio of the compound of formula (II A) to the acylating agent of formula (IX) is generally understood. between 1: 0.95m and 1: 10m.   25. Process for preparing compounds of formula: R - C-- -N-R2 (I V)   RC-Z- $ NH- (CH 2) p N -R 2 e (IV) 0 mi (CH 2) n -CO 2 n which consists of reacting: the compound of formula: R, [RC-2-NH- (CH 2) pN '(11 B) and a compound of formula: Y- (CH 2) n -CO-O-R 11 (X) in a solvent selected from water, C1-C6 alcohols and hydroalcoholic mixtures, formulas in which Z, R, R1, R2, m, n, p and r have the meaning given above, R11 represents a hydrogen atom or an alkali metal, and Y represents a halogen atom.   The process according to claim 25, wherein the molar ratio of the compound of formula (II B) to the compound of formula (X) is generally understood between 1: 0.95n and 1: 10n.   -39 - 27. Process for the preparation of compounds of formula: R - C Z - NH- (CH 2) P - N - R 2 (V)   Wherein the compound of formula: ## STR1 ## wherein Z, R, R 1 , R2, m, n and bridge the meaning given above, and an oxidant, in a solvent chosen from water, C 1 -C 6 alcohols and hydroalcoholic mixtures,   - optionally in the presence of a complexing agent.   28. The method of claim 27, wherein the molar ratio of the compound of formula (II B) to the oxidant is generally between 1: 0.95n and 1: 25n.