Surfactant composition based on glycine betaine amide salts, method for preparing same and uses thereof

Abstract

The present invention relates to a surfactant composition based on a glycine betaine amide salt, as well as to the method for preparing same. It also relates to its use as a wetting agent, particle dispersant and / or corrosion inhibitor and / or for improving the disinfecting power and / or the remanence of the disinfectant effect of antimicrobial substances and / or the insecticidal effect and / or the remanence of insecticidal substances, as well as in the manufacture of various products intended for the treatment and / or cleaning of the body, plants or hard surfaces, the treatment of water and the extraction of oil.

Description

SUBJECT OF THE INVENTION The present invention relates to a surfactant composition based on glycine betaine amide salts, and also to the process for preparing same. It also relates to the use thereof as a wetting agent, particle dispersant and / or corrosion inhibitor and / or for improving the disinfectant power of antimicrobial substances and / or the effect of insecticidal substances, and also for the manufacture of various products intended for the treatment and / or cleaning of the body, of plants or of hard surfaces, for the treatment of water or for the extraction of petroleum. BACKGROUND OF THE INVENTION Surfactants are indispensable raw materials for the manufacture of a variety of products. Among these, cationic surfactants admittedly represent a market that is not as extensive as that of anionic or nonionic surfactants, but they are nevertheless of interest in multiple applications, in particular in the manufacture of detergent and cosmetic products, as well as in water treatment. Patents US-7,829,521 and WO 2013 / 188508 have proposed biodegradable cationic surfactants based on glycine betaine amides, and also a process preparing them. The latter consists in protonating glycine betaine with the aid of an acid, then esterifying it with the aid of a short alcohol, before carrying out an aminolysis reaction on this product with the aid of at least one fatty amine, which may in particular be of vegetable origin. It thus makes it possible to obtain cationic amphiphilic molecules without the conventional step of quaternizing a tertiary amine using methylating agents that are generally toxic. Other similar surfactants are presented in the publication by F. Goursaud et al. in Green Chem., 2008, 10, 310-320. By modifying the operating conditions described in WO 2013 / 188508, the Applicant was able to obtain a surfactant composition enriched in glycine betaine amide and depleted in alkylammonium salts, which has been found to have a lower surface tension than the surfactant compositions described in this document and a better environmental profile. This surfactant composition, described in the application EP 3 584 303, is therefore suitable for numerous applications. However, it has been observed that the prior art surfactant compositions contained a residual short alcohol (such as butanol or hexanol), and also esters and ethers of this alcohol, in addition to the desired glycine betaine amide salt, residual glycine betaine and possibly residual acid and an ammonium salt of the fatty amine used. These alcohols, ethers and esters are poorly watersoluble, or even completely water-insoluble, compounds, which cause difficulties in formulating these surfactants, manifesting in the appearance of a supernatant. In order overcome this drawback, it has been envisaged to remove the residual alcohol by distillation before the aminolysis step. However, this costly solution is not satisfactory from an industrial perspective. In addition, it does not make it possible to remove all of the alcohol, since, under the neutral or basic pH conditions under which this surfactant composition is typically used, the abovementioned ester tends to hydrolyze to liberate additional alcohol. In this context, the Applicant has developed an improved process for synthesizing glycine betaine amides which is not only environmentally friendly and capable of being implemented on an industrial scale under acceptable economic conditions, but which also leads to surfactants which are easier to formulate in an aqueous medium. The process according to the invention comprises a first step of esterifying glycine betaine with the aid of a polyol, in particular glycerol. Although this step is known per se (C. Journoux et al., Green Chemistry, 19(23), 2017), it has never been envisaged that it could be included in a more global process for preparing glycine betaine amides, much less with a view to solving the abovementioned problem. SUMMARY OF THE INVENTION A subject of the invention is a process for preparing a surfactant composition, comprising the successive steps consisting in: (1) reacting glycine betaine or a salt thereof with at least one polyol, in the presence of an organic or inorganic acid, at a temperature of from 100 to 180°C; (2) cooling the reaction medium; (3) adding one or more alkylamines containing from 8 to 36 carbon atoms to the reaction medium; and (4) recovering the surfactant composition thus obtained. In contrast to the processes of the prior art, the process according to the invention does not require a distillation step aiming to remove the residual alcohol from step (1), nor any equipment enabling the water to be distilled during step (1) without simultaneously removing the alcohol, which is volatile. It therefore does not require any pressure control during this step either. It follows that this process is economically more attractive than the known processes for synthesizing glycine betaine amides. A subject of the invention is also a surfactant composition that can be obtained according to this process and contains or consists of: (a) from 40% to 75% by weight of glycine betaine amide salt of formula (1): Xn-[(CH3)3N+-CH2-CONH-R]n, (b) from 8% to 40% by weight of polyol, (c) from 0.5% to 5% by weight of glycine betaine of formula (2): (CH3)3N+-CH2-COO-, (d) optionally, from 0.1% to 10% by weight of salt of glycine betaine ester of polyol of formula (3): Xn-[(CH3)3N+-CH2-COOR']n where R' is a polyol residue, (e) optionally, from 0.1% to 30% by weight of alkylammonium salt of formula (4):  Xn- [NH3+R]n, (f) optionally, from 0.1% to 5% by weight of an organic or inorganic acid salt, relative to the total dry weight of the surfactant composition, where: R is a saturated or unsaturated linear alkyl group comprising from 8 to 36 carbon atoms, X is an organic or inorganic anion, and n is 1 or 2. In addition to its biodegradability (according to the standard OECD 310), its low surface tension and its good foaming power, which are comparable to those of surfactants obtained according to the processes of the prior art, the surfactant composition according to the invention has the advantage of being more soluble in water. Another subject of the invention is the use of the abovementioned surfactant composition as a wetting agent, particle dispersant and / or corrosion inhibitor and / or for improving the disinfectant power and / or the persistence of the disinfectant effect of antimicrobial substances and / or for improving the effect and / or the persistence of insecticidal substances. A subject of the invention is also the use of this composition for the manufacture of plastics or products intended: - for the treatment and / or cleaning of the body, of plants or of hard surfaces, in particular cosmetic products, products for washing vehicles, household products, industrial cleaning products, fiber sizing products and plant protection products; - for the treatment of water; - for the extraction of petroleum. DETAILED DESCRIPTION Surfactant composition The process according to the invention comprises the successive steps consisting in: (1) reacting glycine betaine or a salt thereof with at least one polyol, in the presence of an organic or inorganic acid, at a temperature of from 100 to 180°C; (2) cooling the reaction medium; (3) adding one or more alkylamines containing from 8 to 36 carbon atoms to the reaction medium; and (4) recovering the surfactant composition thus obtained. The first step of this process consists in esterifying glycine betaine, or trimethylglycine. The glycine betaine can be of vegetable or synthetic origin. Although glycine betaine exists on the market in protonated form (as the hydrochloride), it is preferable to use glycine betaine in zwitterionic form according to the invention. It is then necessary to protonate it, in the process according to the invention, with the aid of an organic or inorganic acid. The acid may in particular be chosen from inorganic acids such as hydrochloric acid, sulfuric acid, perhalohydric acids, such as perchloric acid, and mixtures thereof. In a variant, it may be chosen from organic acids, such as alkyl sulfuric acids, for example decyl or lauryl sulfuric acid; arylsulfonic acids, such as benzenesulfonic acid, para-toluenesulfonic acid; alkylsulfonic acids, such as triflic acid, methanesulfonic acid, ethanesulfonic acid, decylsulfonic acid, laurylsulfonic acid or camphorsulfonic acid; sulfosuccinic acid; and mixtures thereof. Lewis acids may also be used. Preferably, it is an organic acid, more preferentially an alkylsulfonic acid and in particular methanesulfonic or ethanesulfonic acid. During the esterification, the acid function of the salified betaine is reacted with a polyol, to result in a glycine betaine ester of polyol which is in salt form. The term "polyol" is understood to mean a linear, cyclic or branched saturated monomeric or polymeric compound containing at least two alcohol (OH) functions. Advantageously, the polyol used according to the invention consists of a hydrocarbon chain optionally interrupted by one or more oxygen atoms and bearing at least two alcohol functions. "Hydrocarbon chain" is understood to mean a structure comprising only carbon and hydrogen atoms. The polyol according to the invention generally comprises at least one primary and / or secondary alcohol function; preferably, it comprises at least one primary alcohol function. Advantageously, the polyol has a melting point of at most 180°C, preferably at most 160°C, and better still at most 150°C, as measured by differential scanning calorimetry according to the standard OECD 102. In addition, it is preferable for the polyol to have a solubility in water at 25°C of at least 25 g / L. Examples of such polyols may be chosen from: linear or branched C2-C6 diols such as ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 1,3-butanediol, 2-methyl-1,3-propanediol, 2-methyl-1,2-propanediol, 1,5-pentanediol, neopentyl glycol, 1,6-hexanediol, 3-methyl-1,5-pentanediol; triols such as glycerol, trimethylolpropane, 1,2,6-hexanetriol; tetrols such as erythritol; hydrogenated sugars such as sorbitol, xylitol, mannitol and maltitol; polyglycerols; polyethylene glycols, preferably having a molar mass ranging from 106 to 8000 g / mol, such as diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, tripropylene glycol, tetrapropylene glycol, PEG-32, PEG-75 and PEG-180; and mixtures thereof. Glycerol is preferred for use in this invention. Glycerol is a biobased reactant that is readily available and less expensive than some alcohols of petrochemical origin. The introduction of the reactants during the first step is not critical. Thus, in one embodiment of the invention, the polyol is mixed with the glycine betaine before the introduction of the acid. Indeed, the polyol may be a coproduct of the extraction of sugar beet vinasse used for producing the glycine betaine. Such a mixture is available in particular from the company Altilis under the commercial reference Betafin® LQD GL. In another embodiment, the glycine betaine is first reacted with the acid before the introduction of the polyol. The esterification reaction is generally carried out in the absence of any solvent, the polyol constituting both the reactant and the medium. Use may generally be made of from 1.0 to 4 equivalents, for example from 1.2 to 2 equivalents, of polyol and / or of from 1.0 to 1.5 equivalents of acid, for example from 1.0 to 1.2 equivalents of acid, per 1 equivalent of glycine betaine. The esterification can be carried out at a temperature of from 100 to 180°C, preferentially from 120 to 170°C, more preferentially from 140 to 160°C, under atmospheric pressure or under reduced pressure (for example from 30 to 200 mbar), for a duration ranging generally from 2 h to 10 h, preferentially from 5 h to 8 h. In contrast to the processes of the prior art using butanol or hexanol instead of a polyol, it is not necessary to use a Dean-Stark apparatus or to precisely control the pressure, insofar as the polyols are not volatile. The sole purpose of reducing the pressure is to distill the water in order to shift the equilibrium of the reaction. During this reaction, one or more of the alcohol functions (hydroxyl groups) of the polyol are esterified with the glycine betaine. In addition, oligomerization of the polyol may occur. It is thus possible to obtain a mixture of glycine betaine esters resulting from the reaction of different alcohol functions of the polyol, or even of these oligomers. The degree of conversion of the glycine betaine into glycine betaine ester is advantageously measured by 1H NMR. The esterification reaction is typically halted when a degree of conversion of at least 90%, generally of from 95% to 99%, has been reached. At the end of this esterification step, it is possible to neutralize the reaction medium, in order to avoid or limit the formation of an ammonium salt between the amine added in the following step and the residual acid or the residual protonated glycine betaine. This is because the formation of this ammonium salt reduces the availability of the fatty amine for the aminolysis reaction and its presence in the surfactant composition obtained at the end of the process may not be desirable due to environmental constraints. This neutralization step can be implemented by adding any suitable base to the reaction medium, such as an organic or inorganic sodium salt, in particular sodium carbonate, sodium hydrogencarbonate or calcium carbonate. In this step, the reaction medium can be heated to a temperature of from 40 to 150°C, for example from 60 to 80°C. After cooling the reaction medium (whether neutralized or otherwise), for example to 20100°C, one or more C8-C36 alkylamines are then added to the reaction medium. Examples of such amines are: dodecylamine (or laurylamine), tetradecylamine, hexadecylamine, octadecylamine, oleylamine, docosanylamine, eicosanylamine, dimer diamines (derived from dimer fatty acids), in particular C36 dimer diamines (such as those available from Cargill under the commercial reference Priamine®), and mixtures thereof. Examples of such mixtures are amines derived from coconut oil. In this step, the alkylamine is advantageously used in the molten form. The amount of alkylamine(s) added can, for example, represent from 0.9 to 1.5 equivalents and preferably from 1.0 to 1.2 equivalents, per 1 equivalent of glycine betaine initially employed. This aminolysis reaction is typically carried out at a temperature of from 50 to 180°C and preferably from 80 to 120°C, at atmospheric pressure. Insofar as the reaction medium does not contain alcohol, it is indeed not necessary, in parallel with the aminolysis reaction, to remove the alcohol by distillation under reduced pressure, in contrast to the processes of the prior art. The aminolysis reaction can be conducted over a period of time of from 0.5 to 7 hours, in particular from 1 to 3 hours. In one embodiment of the invention, the neutralization step described above can be implemented in a variant at the end of the aminolysis step. In this case, sodium ethoxide or any other base having a sufficiently high pKa to deprotonate the fatty amine salt is advantageously used as the base. Thus, the process according to the invention advantageously comprises an additional step of adding a base between steps (2) and (3) or between steps (3) and (4). The surfactant composition thus obtained is then recovered, and this may optionally be diluted in water before use. This process makes it possible to obtain a surfactant composition comprising, and preferably consisting of: (a) from 40% to 75% by weight, preferably from 50% to 70% by weight, of glycine betaine amide salt of formula (1): Xn-[(CH3)3N+-CH2-CONH-R]n, (b) from 8% to 40% by weight, preferably from 10% to 35% by weight, more preferentially from 25% to 35% by weight, of polyol, (c) from 0.5% to 5% by weight, preferably from 1% to 3% by weight, of glycine betaine of formula (2): (CH3)3N+-CH2-COO-, (d) optionally, from 0.1% to 10% by weight of salt of glycine betaine ester of polyol of formula (3): Xn-[(CH3)3N+-CH2-COOR']n where R' is a polyol residue, (e) optionally, from 0.1% to 30% by weight, in particular from 1% to 20% by weight or from 0.1% to 0.5% by weight, of alkylammonium salt of formula (4): Xn-[NH3+R]n, (f) optionally, from 0.1% to 5% by weight of an organic or inorganic acid salt, relative to the total dry weight of the surfactant composition, where: R is a saturated or unsaturated linear alkyl group comprising from 8 to 36 carbon atoms, X is an organic or inorganic anion, and n is 1 or 2. "Polyol residue" is understood to mean the unit derived from the polyol which is incorporated into the polyol ester salt after esterification of the polyol with the glycine betaine. The compound (f) is present in the case where the process according to the invention comprises a step of neutralization with the aid of a base and is the product of reaction of this base with the acid used in the esterification step. It is preferable in all cases for the surfactant composition according to the invention to contain less than 5% by weight, advantageously less than 3% by weight, more preferentially less than 1% by weight, or even none at all, of saturated or unsaturated linear or branched (preferably linear) alcohol comprising from 8 to 36 carbon atoms. Uses The surfactant composition according to the invention can be used in a variety of applications as a wetting agent, particle dispersant and / or corrosion inhibitor and / or for improving the disinfectant power of antimicrobial substances and / or the effect of insecticidal substances. It can in particular be used for the manufacture of plastics or various products intended in particular: - for the treatment and / or cleaning of the body, of plants, of textiles or of hard surfaces, in particular cosmetic products, such as shampoos, liquid soaps, bubble baths and shower gels; products for washing vehicles such as automobiles, trucks, trains, buses or planes; household products such as detergents for windows, wall surfaces, floors or dishware; laundry detergents or fabric softeners; industrial cleaning products; fiber sizing products; plant protection products; pigmented products such as paints or varnishes; - for the treatment of water; - for the extraction of petroleum. When it is used in the cleaning of hard surfaces, such as windows or bodywork surfaces, or textiles, it was in particular observed that the composition according to the invention accelerated the subsequent drying of the surface without leaving behind traces of limescale on drying. In addition, when the surface is a vehicle, it was observed that the cleaning of fine brake dust on the wheels was improved compared to conventional cationic surfactants. Lastly, the effectiveness of the composition according to the invention in alkaline medium makes it possible to avoid the drawbacks associated with the use of acidic compositions, in particular their corrosive effect. In the case of the treatment of water, the composition according to the invention makes it possible to detach the biofilm without destroying the effectiveness of the ion-exchange resins, in contrast to conventional cationic surfactants which moreover have a not insignificant impact on the environment given their lack of biodegradability, or their slower biodegradability. This ability to detach biofilms can also be exploited in petroleum extraction processes. In cosmetic applications, the composition according to the invention is compatible with the conventional anionic surfactants and makes it possible to improve the creamy nature of the foam they generate. It also protects iron aerosol devices against corrosion. In the manufacture of plastics, the composition according to the invention makes it possible to impart electrostatic properties on the surface of the plastic, without affecting its recyclability on account of its biobased nature. When it is used in the manufacture of plant protection products, the composition according to the invention makes it possible to improve the persistence of the active ingredients and the water resistance of products such as herbicides, pesticides or plant growth modifiers, which can thus be used in smaller amounts. This composition can thus be added, in a form diluted to 25% in water, in a proportion of 0.4% by weight, to a product containing a neutral or alkaline medium, for example. The composition according to the invention can also be used in a process for the extraction, storage, intermediate storage or refining of petroleum in order to limit the corrosion of equipment. In this application, it can be added to the petroleum up to an amount of 500 to 1000 ppm, for example. The products described above, comprising a composition according to the invention, may also include at least one compound chosen from: anionic surfactants, nonionic surfactants, antimicrobial agents and / or insecticidal substances, and mixtures thereof. Examples of anionic surfactants are: ethoxylated fatty alcohol sulfate salts, sulfosuccinates, sarcosinates, alkyl and dialkyl phosphates, fatty acid soaps, and mixtures thereof. The nonionic surfactants can for example be chosen from: fatty acid esters of polyols such as optionally polyethoxylated fatty acid esters of glycerol, optionally polyethoxylated fatty acid esters of sorbitan, fatty acid esters of polyoxyethylene, fatty acid esters of sucrose such as sucrose stearate; fatty alcohol polyoxyethylene ethers, fatty alcohol sugar ethers, especially alkylpolyglucosides (APGs), polyether-modified polysiloxanes, and mixtures thereof. The antimicrobial agents can be chosen from quaternary ammoniums, aldehydes (such as glutaraldehyde and formaldehyde), ethanol, halogenated derivatives, oxidizing agents, phenolic compounds, parabens, isothiazolones (or isothiazolinones), benzoates, imidazoline, hydantoin, guanidine, organic acids such as lactic acid, and mixtures thereof. The insecticidal substances can be chosen from organophosphorus agents (such as acephate, chlorpyrifos or bromophos), nicotinoids, pyrethroids (such as permethrin, bifenthrin or fenvalerate), monoterpenes (such as p-menthane-3,8-diol), organohalogen compounds (such as lindane, dicofol or toxaphene), N,N-diethyl-3-methylbenzamide, pyrethrin derivatives (such as pyrethrin I, pyrethrin II or jasmolin I), sulfones, sulfonates, formamidines, benzoylureas, rotenones, alkaloids, quassin, ryanidone, aconitine, geraniol, and mixtures thereof. Depending on the envisaged application, these products can additionally comprise at least one ingredient chosen from: plant protection or cosmetic active agents, enzymes, chelating agents, thickeners, fatty substances (oils, waxes and / or pastes), fillers, preservatives, pigments and dyes, antioxidants, optical brighteners, and mixtures thereof. These products are advantageously in the form of an aqueous solution or aqueous gel. In a variant, they can be in the form of an oil-in-water or water-in-oil emulsion or even a paste. In any case, the aqueous phase present in these products advantageously has a pH ranging from 1 to 12, in particular from 8 to 12 and preferably from 9 to 11. These products can be packaged in any device suitable for the envisaged use and in particular in a pump bottle, a tube, a pot, an aerosol device or a wipe. They advantageously contain from 0.1% to 25% by weight, for example from 1% to 10% by weight, of surfactant composition according to the invention. FIGURES Figure 1 illustrates the appearance of a 5% solution in water of a surfactant composition according to the invention (on the right) and of a comparative surfactant composition (on the left). EXAMPLES The invention will be better understood in light of the examples that follow, which are given purely by way of illustration and are not intended to limit the scope of the invention, which is defined by the appended claims. Example 1: Synthesis of a surfactant composition based on betainylaminododecane salt Betainylaminododecane mesylate is produced from glycine betaine in a one-pot process involving two reaction steps, as illustrated below: Example 1-1: synthesis from glycine betaine and glycerol 5 A 100-mL two-necked round-bottom flask equipped with a distillation assembly is charged with glycerol (15.725 g, 170.8 mmol, 2.0 eq) and glycine betaine (10.001 g, 85.4 mmol, 1.0 eq). The setpoint temperature is fixed at 150°C and the pressure is reduced to 200 mbar. Once the temperature and pressure conditions have been reached, a 70% methanesulfonic acid solution (11.839 g, 86.2 mmol, 1.01 eq) is introduced. Once the introduction has ended, the pressure is gradually decreased to 30 mbar. 10 The degree of conversion is monitored by 1H NMR analyses. At 6h00 of reaction time, the degree of conversion is 95%. The setpoint temperature is fixed at 100°C. Once the mixture is at 100°C, the assembly is returned to atmospheric pressure and dodecylamine (16.005 g, 86.3 mmol, 1.01 eq), melted beforehand, is added. The reaction mixture is then heated at 100°C with vigorous stirring at atmospheric pressure for 1h30. 15 The reaction mixture is then recovered and has the composition indicated in Table 1. [Table 1] Constituent Molar mass (g / mol) % by weight Betainylaminododecane mesylate 380.588 57.2% Dodecylammonium mesylate 281.455 8.5% Glyceryl betainate mesylate 287.327 0.7% Glycine betaine 117.148 2.2% Glycerol 92.094 31.3% Example 1-2: synthesis from sugar beet vinasses A 50-mL round-bottom flask equipped with a distillation assembly is charged with Betafin® LQD GL [10.0 g containing: glycerol (31.2 mmol, 1.46 eq); glycine betaine (21.3 mmol, 1.0 eq)] and a 70% methanesulfonic acid solution (3.481 g, 25.4 mmol, 1.2 eq). The mixture is stirred and the setpoint temperature is fixed at 160°C. The pressure is decreased to 30 mbar in 35 min. The degree of conversion is monitored by 1H NMR analyses. At 7h30 of reaction time, the degree of conversion is 96%. The setpoint temperature is fixed at 100°C. Once the mixture is at 100°C, the assembly is returned to atmospheric pressure and dodecylamine (5.099 g, 27.5 mmol, 1.3 eq), melted beforehand, is added. The reaction mixture is then heated to 130°C with vigorous stirring at atmospheric pressure for 2 hours. The reaction mixture is then recovered and has the composition indicated in Table 2. [Table 2] Constituent Molar mass (g / mol) % by weight Betainylaminododecane mesylate 380.588 64.2% Dodecylammonium mesylate 281.455 13.8% Glyceryl betainate mesylate 287.327 0% Glycine betaine 117.148 2.7% Glycerol 92.094 19.4% Example 2: Synthesis of a surfactant composition based on C12-C18 betainylaminoalkane salts A 1-L reactor equipped with a distillation assembly is charged with glycerol (117.056 g, 1.271 mol, 2.0 eq) and glycine betaine (74.450 g, 0.636 mol, 1.0 eq). The mixture is stirred and heated to 150°C at a pressure of 200 mbar. Once the temperature and pressure conditions have been reached, a 70% methanesulfonic acid solution (88.100 g, 0.642 mmol, 1.01 eq) is introduced into the reactor. Once the introduction has ended, the pressure is gradually decreased to 30 mbar. The degree of conversion is monitored by 1H NMR analyses. At 5h30 of reaction time, the degree of conversion is 99%. The reaction mixture is cooled to 100°C. Once the mixture is at 100°C, the reactor is returned to atmospheric pressure and cocoamine (114.100 g, 0.580 mmol, 0.91 eq) and octadecylamine (17.131 g, 0.064 mol, 0.1 eq), melted beforehand, are added. The reaction mixture is then heated to 150°C with vigorous stirring at atmospheric pressure for 1 hour. The reaction mixture is then recovered by draining the reactor and has the composition indicated in Table 3. [Table 3] Constituent Molar mass (g / mol) % by weight Betainylaminoalkane mesylate 399.216 51.4% Alkylammonium mesylate 300.083 12.0% Glyceryl betainate mesylate 287.327 6.6% Glycine betaine 117.148 2.0% Glycerol 92.094 28.1% Example 3: Synthesis of a surfactant composition based on betainylaminooctadec-9-ene salt A 250-mL reactor equipped with a distillation assembly is charged with Betafin® LQD GL [100.478 g containing: glycerol (336.7 mmol, 1.57 eq); glycine betaine (214.4 mmol, 1.0 eq)]. The mixture is stirred and heated to 90°C at atmospheric pressure. Once the temperature has been reached, a 70% methanesulfonic acid solution (35.2 g, 256.4 mmol, 1.2 eq) is introduced into the reactor. Once the introduction has ended, the setpoint temperature is fixed at 150°C and the pressure is gradually decreased. After 1h15 of reaction, the pressure is 60 mbar. The degree of conversion is monitored by 1H NMR analyses. At 7h00 of reaction time, the degree of conversion is 93%. The reaction mixture is cooled to 100°C. Once the mixture is at 100°C, the reactor is returned to atmospheric pressure and oleylamine (74.155 g, 277.2 mmol, 1.29 eq), melted beforehand, is added. The reaction mixture is then heated to 150°C with vigorous stirring at atmospheric pressure for 2 hours. The reaction mixture is then recovered by draining the reactor and has the composition indicated in Table 4. [Table 4] Constituent Molar mass (g / mol) % by weight Betainylaminooctadec-9-ene mesylate 462.734 62.7% Oleylammonium mesylate 363.601 18.9% Glyceryl betainate mesylate 287.327 1.3% Glycine betaine 117.148 2.4% Glycerol 92.094 14.7% Example 4: Synthesis of a surfactant composition based on betainylaminododecane salt Betainylaminododecane mesylate is produced from glycine betaine in a one-pot process involving three reaction steps, as illustrated below: Glycerol (2.0 eq) 70% MSA (1.01 eq) 150°C Reduced P 1 / Na2CO3 (0.02 eq) 70°C, atm. P 2 / Dodecylamine (0.9 eq) 70-100°C atm P The experiment is carried out in a 100 mL vessel with baffles, equipped with a turbine-form stirrer blade, a temperature probe and a distillation assembly. The vessel is charged with glycerol (23.58 g, 0.256 mol, 2.0 eq) and glycine betaine (15.00 g, 0.128 mol, 1.0 eq). The setpoint temperature of the reaction mixture is fixed at 150°C and the pressure is reduced to 200 mbar. Once the temperature and pressure conditions have been reached, a 70% methanesulfonic acid solution (17.75 g, 0.129 mol, 1.01 eq) is introduced via a dropping funnel attached to one of the necks of the lid of the vessel. Once the introduction has ended, the pressure is gradually decreased to 30 mbar. The degree of conversion is monitored by 1H NMR analyses. At 6h00 of reaction time, the degree of conversion is 97.7%. The setpoint temperature is fixed at 70°C. Once the mixture is at 70°C, the assembly is returned to atmospheric pressure and sodium carbonate (0.27 g, 2.6 mmol, 0.02 eq) is added. The reaction mixture is then heated at 70°C with vigorous stirring at atmospheric pressure for 30 minutes. Dodecylamine (21.36 g, 0.115 mol, 0.9 eq), melted beforehand, is then added. The reaction mixture is then heated to 100°C with vigorous stirring at atmospheric pressure for 5 h. The reaction mixture is then recovered and has the composition indicated in Table 5 below. [Table 5] Constituent Molar mass (g / mol) % by weight Betainylaminododecane mesylate 380.588 57.4% Dodecylammonium mesylate 281.455 4.6% Glyceryl betainate mesylate 287.327 1.8% Glycine betaine 117.148 2.0% Glycerol 92.094 32.9% Sodium mesylate 118.082 1.4% Example 5: Synthesis of a surfactant composition based on betainylaminododecane salt Betainylaminododecane mesylate is produced from glycine betaine in a one-pot process involving three reaction steps, as illustrated below: Glycerol (2.0 eq) 70% MSA (1.01 eq) 150°C Reduced P 1 / Dodecylamine (0.9 eq) 100°C, atm. P 2 / EtONa (0.2 eq) 70°C, atm. P The experiment is carried out in a 100 mL vessel with baffles, equipped with a turbine-form stirrer blade, a temperature probe and a distillation assembly. The vessel is charged with glycerol (23.597 g, 0.2562 mol, 2.0 eq) and glycine betaine (15.001 g, 0.1280 mol, 1.0 eq). The setpoint temperature of the reaction mixture is fixed at 150°C and the pressure is reduced to 200 mbar. Once the temperature and pressure conditions have been reached, a 70% methanesulfonic acid solution (17.775 g, 0.1295 mol, 1.01 eq) is introduced via a dropping funnel attached to one of the necks of the lid of the vessel. Once the introduction has ended, the pressure is gradually decreased to 30 mbar. The degree of conversion is monitored by 1H NMR analyses. At 7 h of reaction time, the setpoint temperature of the reaction mixture is fixed at 100°C. Once the mixture is at 100°C, the assembly is returned to atmospheric pressure and dodecylamine (21.369 g, 0.1153 mol, 0.9 eq), melted beforehand, is added. The reaction mixture is then heated at 100°C with vigorous stirring at atmospheric pressure for 3 hours. The setpoint temperature of the reaction mixture is fixed at 70°C. Once the mixture is at 70°C, a first addition of sodium ethoxide (21% solution, 5.73 mL, 0.0154 mol, 0.12 eq) is carried out. After 1 h of reaction, a second addition of sodium ethoxide (21% solution, 2.39 mL, 0.0064 mol, 0.05 eq) is carried out. After 1 h of reaction, a third addition of sodium ethoxide (21% solution, 1.43 mL, 0.0038 mol, 0.03 eq) is carried out. After 1 h of reaction, the reaction mixture is concentrated under vacuum in order to distill the ethanol. The mixture obtained then has the composition indicated in Table 6 below. [Table 6] Constituent Molar mass (g / mol) % by weight Betainylaminododecane mesylate 380.588 62.0% Dodecylammonium mesylate 281.455 0.3% Glyceryl betainate mesylate 287.327 0.2% Glycine betaine 117.148 2.5% Glycerol 92.094 32.7% Sodium mesylate 118.082 2.3% Example 6: Properties of the surfactant compositions 6-1: Surface tension The surface tension of the surfactant compositions of Examples 1-1 to 3 was measured using a goniometer according to the pendant drop method described in the standard EN ISO 19403-3 (2020). Results: [Table 7] Example Surface tension at 1% w / w (mN / m) 1-1 37.3 1-2 32 2 35.6 3 34.3 6-2: Solubility in water The solubility in water was evaluated for a surfactant according to the invention (TA1), having the following composition: 5                                              [Table 8] Composition by mass Betainylaminododecane mesylate 58.4% Laurylammonium mesylate 9.5% Glyceryl betainate mesylate 0.0% Glycine betaine 3.1% Glycerol 29.0% in comparison with a prior art surfactant (TA2) obtained from hexanol and having the following composition: [Table 9] Composition by mass Betainylaminododecane mesylate 56.9% Laurylammonium mesylate 9.9% Hexyl betainate mesylate 3.3% Glycine betaine 1.0% Hexanol 29.0% 10 These surfactants TA1 and TA2 were diluted in a proportion of 5% by weight in water. As shown in Figure 1, the solution obtained using the surfactant TA1 (on the right) remained clear, while that obtained using surfactant TA2 (on the left) exhibited particles in suspension, 15 reflecting poor dissolution of the surfactant in water. Example 7: Formulations Several types of products can be prepared using the surfactant compositions according to the invention, where CTx denotes the surfactant composition prepared according to Example x above. Household detergent 80% lactic acid                    2.00% CT1-1                         0.40% Hydroxyethylcellulose              0.30% Chelating agent                    0.20% Fragrance                        0.20% Colorant                         0.01% Deionized water              qs 100.00% This product can be used for cleaning hard surfaces. Vehicle bodywork shampoo CT2                  3-5% Ethoxylated alcohol        0-5% Chelating agent*           5-10% Sodium hydroxide         0.5-2% Water            qs    100% * Dissolvine® GL from AkzoNobel or Trilon® M from BASF This product can be applied to a vehicle and then, after a leave-on time of 5 minutes, be rinsed off under high pressure. Water treatment MEA (monoethanolamine)                          5-10% CT3                                          20-25% Anti-redeposition polymer                             10-25% Water                                         qs 100% Hair conditioner [Table 10] Ingredients % Material CT5 4% Olive oil 5.00% Cetearyl alcohol 3% Panthenol 0.15% Citric acid Fragrance 0.05% Preservative 0.01% Demineralized water qs 100%

Claims

1. A process for preparing a surfactant composition, comprising the successive steps consisting in:(1) reacting glycine betaine or a salt thereof with at least one polyol, in the presence of an organic or inorganic acid, at a temperature of from 100 to 180°C;(2) cooling the reaction medium to a temperature of from 20 to 100°C;(3) adding one or more alkylamines containing from 8 to 36 carbon atoms to the reaction medium; and(4) recovering the surfactant composition thus obtained.

2. The process as claimed in claim 1, characterized in that the polyol consists of a hydrocarbon chain optionally interrupted by one or more oxygen atoms and bearing at least two alcohol functions, preferably at least one primary alcohol function.

3. The process as claimed in claim 1 or 2, characterized in that the polyol is chosen from: linear or branched C2-C6 diols such as ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 1,3-butanediol, 2-methyl-1,3-propanediol, 2-methyl-1,2-propanediol, 1,5-pentanediol, neopentyl glycol, 1,6-hexanediol, 3-methyl-1,5-pentanediol; triols such as glycerol, trimethylolpropane, 1,2,6-hexanetriol, 1,2,4-butanetriol; tetrols such as erythritol; hydrogenated sugars such as sorbitol, xylitol, mannitol and maltitol; polyglycerols; polyethylene glycols, preferably having a molar mass ranging from 106 to 8000 g / mol, such as diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, tripropylene glycol, tetrapropylene glycol, PEG-32, PEG-75 and PEG-180; and mixtures thereof; preferably, the polyol is glycerol.

4. The process as claimed in any one of claims 1 to 3, characterized in that the acid is chosen from: inorganic acids, such as hydrochloric acid, sulfuric acid, perhalohydric acids, such as perchloric acid, and mixtures thereof; organic acids, such as alkyl sulfuric acids, for example decyl or lauryl sulfuric acid; arylsulfonic acids, such as benzenesulfonic acid, paratoluenesulfonic acid; alkylsulfonic acids, such as triflic acid, methanesulfonic acid, ethanesulfonic acid, decylsulfonic acid, laurylsulfonic acid or camphorsulfonic acid;sulfosuccinic acid; and mixtures thereof; or Lewis acids; preferably, the acid is an organic acid, more preferentially an alkylsulfonic acid and in particular methanesulfonic or ethanesulfonic acid.

5. The process as claimed in any one of claims 1 to 4, characterized in that the alkylamine is chosen from: dodecylamine, tetradecylamine, hexadecylamine, octadecylamine, oleylamine, docosanylamine, eicosanylamine, C36 dimer diamines and mixtures thereof, in particular coconut oil derivatives.

6. The process as claimed in any one of claims 1 to 5, characterized in that it additionally comprises a step of adding a base between steps (2) and (3) or between steps (3) and (4).

7. A surfactant composition capable of being obtained according to the process as claimed in any one of claims 1 to 6, characterized in that it comprises, and preferably consists of:(a) from 40% to 75% by weight, preferably from 50% to 70% by weight, of glycine betaine amide salt of formula (1): Xn-[(CH3)3N+-CH2-CONH-R]n,(b) from 8% to 40% by weight of polyol,(c) from 0.5% to 5% by weight of glycine betaine of formula (2): (CH3)3N+-CH2-COO-,(d) optionally, from 0.1% to 10% by weight of salt of glycine betaine ester of polyol of formula (3): Xn-[(CH3)3N+-CH2-COOR']n where R' is a polyol residue,(e) optionally, from 0.1% to 30% by weight of alkylammonium salt of formula (4): Xn-[NH3+R]n,(f) optionally, from 0.1% to 5% by weight of an organic or inorganic acid salt, relative to the total dry weight of the surfactant composition, where:R is a saturated or unsaturated linear alkyl group comprising from 8 to 36 carbon atoms,X is an organic or inorganic anion, and n is 1 or 2.

8. The composition as claimed in claim 7, characterized in that it contains less than 5% by weight, advantageously less than 3% by weight, more preferentially less than 1% by weight, or even none at all, of saturated or unsaturated linear or branched (preferably linear) alcohol comprising from 8 to 36 carbon atoms.

9. The use of the composition as claimed in claim 7 or 8 as a wetting agent, particle dispersant and / or corrosion inhibitor and / or for improving the disinfectant power and / or the persistence of the disinfectant effect of antimicrobial substances and / or the effect of insecticidal substances.

510. The use of the composition as claimed in claim 7 or 8 for the manufacture of plastics or products intended:- for the treatment and / or cleaning of the body, of plants or of hard surfaces, in particular cosmetic products, products for washing vehicles, household products, industrial cleaning 10 products, fiber sizing products and plant protection products;- for the treatment of water;- for the extraction of petroleum.

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