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    • 专利摘要:
    The present invention relates to a process for the preparation of a surfactant composition based on the glycine ester betaine salt, as well as the composition. thus obtained. It also relates to the use of this composition as a wetting agent, dispersing of particles and / or corrosion inhibitor and / or for improving the disinfecting power of antimicrobial substances, as well as in the manufacture of various products intended for the treatment and / or the cleaning of the body, plants or hard surfaces, water treatment, road surfacing or oil extraction. It further relates to a product comprising the above composition.
    公开号:FR3088930A1
    申请号:FR1871892
    申请日:2018-11-27
    公开日:2020-05-29
    发明作者:Freddy PESSEL；Francis Galle；Pierre-Yves Divet；Xavier Roussel
    申请人:Surfactgreen SAS；
    IPC主号:
    专利说明:

    Title of the invention: Process for the preparation of a surfactant composition based on the glycine ester salt of betaine and composition thus obtained [0001] OBJECT OF THE INVENTION [0002] The present invention relates to a process for preparing a surfactant composition based on glycine ester salt betaine, as well as the composition thus obtained. It also relates to the use of this composition as a wetting agent, dispersing of particles and / or corrosion inhibitor and / or for improving the disinfecting power of antimicrobial substances, as well as in the manufacture of various products intended for the treatment and / or cleaning of bodies, plants or hard surfaces, water treatment, road surfacing or petroleum extraction. It further relates to a product comprising the above composition.
    BACKGROUND OF THE INVENTION [0004] Surfactants are essential raw materials for the manufacture of a variety of products. Among these, cationic surfactants certainly represent a less extensive market than 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.
    Due to their toxicity, certain surfactants such as dimethyldialkylammonium salts, present in most fabric softeners, see their use limited, or even abandoned, in certain European countries such as Germany and the Netherlands. Under ecological pressure, producers of surfactants must offer products that are less polluting, more biodegradable and have the lowest possible ecotoxicity. In addition to environmental constraints, consumers want to have the most natural products possible.
    In this context, glycine betaine, an inexpensive natural substance, constitutes a raw material of choice for the preparation of surfactants. Derived from the sugar beet molasses, obtained after sucrose extraction, it currently remains a by-product of the sugar industry. The grafting on glycine betaine of fatty alcohols and amines provides access to cationic amphiphilic molecules without the conventional stage of quaternization of a tertiary amine using generally toxic methylating agents.
    It was thus proposed in US Pat. No. 7,829,521 of betaine glycine esters obtained by reaction of betaine glycine with at least two equivalents of a sulfonic acid, such as methanesulfonic acid, and an alcohol comprising at least 18 carbon atoms. The cationic surfactants thus obtained are present in a mixture with the residual reagents and this mixture can optionally be enriched with glycine ester betaine by treatment with an organic solvent and / or purified on a column of silica gel. It is thus possible to obtain an octadecyl ester or octadecenyl glycine betaine with a yield of about 70% or 85%, respectively. These have a surface tension of around 37 mN / m and are more particularly intended for cosmetic application.
    Other similar surfactants and also with a shorter chain (lauric ester) are presented in the publication by L. Goursaud et al in Green Chem., 2008, 10, 310-320. These surfactants are also prepared in the presence of an amount of methanesulfonic acid of at least two equivalents, relative to the amount of glycine betaine used, which is described as being necessary for obtaining an acceptable yield. (at least 70%). Here again, the surface tension of the esters obtained after purification is very high (from 32 to 37 mN / m).
    The lauric ester of glycine betaine is also described, alone or in admixture with the corresponding myristic ester, in patent application WO 2013/188508. In this document, it is demonstrated (Table 5) that the crude reaction mixture has a lower surface tension than the pure glycine ester betaine, making it possible to consider its use in household detergents. This reaction mixture contains in all cases less than 65% by weight of glycine ester betaine and / or more than 20% by weight of residual sulfonic acid (Table 4). However, it has been demonstrated by the present inventors that the adjustment of these two parameters makes it possible to further lower the surface tension of these mixtures.
    After extensive research, the inventors have thus developed a modified process for the preparation of glycine ester salts of betaine in which the esterification reaction is carried out in the presence of a reduced amount of acid and more high temperature. This process makes it possible to obtain surfactant compositions having lower surface tensions and possibly a higher proportion of glycine ester betaine than the surfactant compositions described in the prior art, without appreciably affecting the yield of the reaction. This process can also be implemented in a shorter time and does not require a step of purifying the product obtained.
    The synthesis process used according to the invention is simple, effective, respectful of the environment, without solvent or polluting discharge, and easily transposable on an industrial scale to obtain in a reproducible manner a particularly effective surfactant composition.
    Summary of the invention The subject of the invention is a process for the preparation of a surfactant composition, comprising the successive stages consisting in:
    (1) reacting betaine glycine or one of its salts with a linear or branched fatty alcohol, saturated or unsaturated, containing from 8 to 22 carbon atoms, in the presence of an organic or inorganic acid;
    (2) cooling the reaction medium to a temperature of 20 to 90 ° C; and (3) recovering the surfactant composition thus obtained, characterized in that the organic or inorganic acid represents from 1.1 to 2.0 molar equivalent relative to the number of moles of glycine betaine and in that that the reaction is carried out at a temperature of 150 to 180 ° C.
    It also relates to the surfactant composition obtained according to this process, containing the following constituents:
    (A) from 65 to 85% by weight, preferably from 70 to 80% by weight, of glycine ester salt of betaine, (b) from 1 to 20% by weight, for example of 1 to 9% by weight or from 10 to 20% by weight of fatty alcohol, (c) from 1 to 20% by weight, for example from 5 to 15% by weight of organic or inorganic acid, and (d) from 1 to 20% by weight, for example from 2 to 15% by weight, of glycine betaine, relative to the total weight of these four constituents.
    The invention also relates to the use of the above-mentioned surfactant composition as a wetting agent, particle dispersant and / or corrosion inhibitor and / or to improve the disinfecting power and / or the persistence of the disinfecting effect of antimicrobial substances.
    It also relates to the use of this composition for the manufacture of plastics or of products intended:
    - treatment and / or cleaning of the body, plants or hard surfaces, in particular cosmetic products, vehicle wash products, household products, industrial cleaning products, sizing products fibers and phytosanitary products;
    - water treatment;
    - road surfaces; or [0028] - oil extraction.
    It further relates to a product comprising the above composition and at least one constituent chosen from: (a) anionic surfactants, nonionic surfactants and their mixtures and / or (b) antimicrobial agents.
    In addition to its low surface tension, the surfactant composition obtained according to the invention has the advantage of being biodegradable (according to OECD standard 301), slightly toxic for the environment (according to OECD standards 201 and 202) and for the man.
    Description of the embodiments Process [0032] The surfactant composition according to the invention can be prepared according to a process for the esterification of glycine betaine, or trimethylglycine. The glycine betaine can be of vegetable or synthetic origin. It is necessary to protonate it beforehand using an organic or inorganic acid, insofar as it is in zwitterionic form (presence of a carboxylate function). The acid can in particular be chosen from inorganic acids such as hydrochloric acid, sulfuric acid, perhalohydric acids, such as perchloric acid, and mixtures thereof. Alternatively, it can be chosen from organic acids, such as alkyl sulfuric acids, for example decyl or lauryl sulfuric acid; arylsulfonic acids, such as benzene sulfonic acid, paratoluene sulfonic acid, camphosulfonic acid; alkylsulfonic acids, such as triflic acid, methane sulfonic acid, ethanesulfonic acid, decylsulfonic acid, laurylsulfonic acid; sulfosuccinic acid; and their mixtures. Lewis acids can also be used. Preferably, it is an alkylsulfonic acid and in particular methanesulfonic acid, insofar as it is easily biodegradable.
    During the esterification, the acid function of the salified betaine is reacted with a fatty alcohol, to lead to a glycine ester betaine in the form of salt. By fatty alcohol is meant a linear or branched alcohol (preferably linear), saturated or unsaturated, comprising from 8 to 22 carbon atoms. Examples of such fatty alcohols can be chosen from the group consisting of: caprylic alcohol (C8: 0), decyl alcohol (C10: 0), undecyl alcohol (Cl 1: 0), lauric alcohol (C12: 0), myristic alcohol (C14: 0), cetyl alcohol (C16: 0), palmitoleic alcohol (C16: l), stearic alcohol (C18: 0), oleic alcohol (C18: 1), linoleic alcohol (C18: 2), linolenic alcohol (C18: 3), arachidic alcohol (C20: 0), arachidonic alcohol (C20: 4), behenic alcohol (C22: 0), hexyldecanol, octyldodecanol and their mixtures. Mixtures of usable fatty alcohols can be produced from one or more vegetable oils and in particular soybean, olive, sunflower, corn, palm, copra, cotton, flax, wheat germ, safflower or rapeseed, for example. Particular examples of fatty alcohols which can be used according to the invention are lauric alcohol, alone or in mixture with myristic alcohol, as well as oleic alcohol. It is preferred not to use stearic alcohol.
    The esterification reaction is generally carried out in the absence of solvent. The water produced during the reaction also contributes to the solubilization of the glycine betaine in the reaction mixture.
    For the implementation of this reaction, one can use from 0.8 to 2 equivalents, for example from 0.9 to 1.0 equivalent, or as a variant from 1.1 to 1.8 equivalent, preferably in this case from 1.2 to 1.6 equivalent and, better, from 1.3 to 1.5 equivalent of fatty alcohol. In any case, 1.1 to 2.0 equivalent is used, for example 1.3 to 1.9 equivalent, and preferably 1.5 to 1.7 equivalent of organic or inorganic acid, for 1 equivalent glycine betaine. The esterification is carried out at a temperature of 150 to 180 ° C. In a preferred embodiment of the invention, the glycine betaine, the fatty alcohol and the organic or inorganic acid are mixed at a temperature of 160 to 180 ° C, for example 170 ° C, then the temperature of the mixture is lowered from 10 to 20 ° C, up to 140-160 ° C, for example at 150 ° C, before the start of the reaction. The reaction can be carried out at atmospheric pressure or preferably under reduced pressure, for example at a pressure of 10 to 600 mbar. The pressure will generally be lower the longer the chain length of the fatty alcohol involved. Those skilled in the art will in any event be able to adjust the pressure chosen so as to eliminate the water formed during the reaction and to shift the balance towards the formation of the ester. The reaction medium is then cooled to a temperature of 20 to 90 ° C.
    The surfactant composition thus obtained, which contains at least 65% by weight, generally from 65 to 85% by weight, for example from 70 to 80% by weight, of at least one ester salt, is then recovered. glycine betaine of formula X n [(CH3) 3N + -CH2-COOR] n where: X is an organic or inorganic anion, R is an alkyl radical corresponding to the fatty alcohol R-OH used in the reaction of esterification, and n is 1 or 2.
    The anion X is derived from the acid XH described above and can therefore in particular be a chloride, a sulfate, a perchlorate, an alkylsulfate ion, in particular decylsulfate or laurylsulfate, an arylsulfonate ion, especially benzene sulfonate, paratoluene sulfonate , camphosulfonate, an alkylsulfonate ion, in particular triflate, methanesulfonate, ethanesulfonate, decylsulfonate, laurylsulfonate, or a sulfosuccinate ion. It is preferred according to the invention that X is chosen from alkylsulfonates and arylsulfonates, in particular from methanesulfonate, triflate, paratoluenesulfonate and camphosulfonate ions. It is advantageously the methanesulfonate ion.
    The radical R can in turn be chosen from octyl (C8: 0), decyl (C10: 0), undecyl (Cl 1: 0), lauryl (C12: 0), myristyle (C14: 0) groups , cetyl (C16: 0), palmitoleyl (Cl6: 1), stearyl (Cl8: 0), oleyl (Cl8: 1), linoleyl (Cl8: 2), linolenyl (Cl8: 3), arachidyl (C20: 0), arachidonyl (C20: 4), behenyl (C22: 0), hexyldecyl and octyldodecyl.
    It is understood that, in the case where several fatty alcohols are used in the esterification reaction, the surfactant composition obtained according to the invention will comprise several salts of glycine esters betaine. The expression a glycine ester salt betaine must therefore be understood, in the context of this description and unless otherwise indicated, as referring to one or more of these salts.
    More specifically, the surfactant composition obtained according to the invention contains:
    (A) from 65 to 85% by weight, preferably from 70 to 80% by weight, of glycine ester salt of betaine, (b) from 1 to 20% by weight, for example of 1 to 9% by weight or from 10 to 20% by weight of fatty alcohol, (c) from 1 to 20% by weight, for example from 5 to 15% by weight of organic or inorganic acid, and (d) from 1 to 20% by weight, for example from 2 to 15% by weight, of glycine betaine, relative to the total weight of these four constituents.
    Advantageously, these constituents represent a total of 90 to 100%, and preferably 95 to 100% of the weight of the composition. The rest of the constituents of the composition can in particular consist of a fatty alcohol ether, of formula RO-R where R is as defined above.
    The surfactant composition obtained according to the invention can in particular comprise the above constituents in the following proportions:
    - in the case where the fatty alcohol is lauric alcohol: from 70 to 80% by weight of lauric ester salt of glycine betaine, from 0.1 to 15% by weight of lauric alcohol, 10 to 15% by weight of organic or inorganic acid and from 1 to 10% by weight of glycine betaine;
    - in the case where the fatty alcohol is a mixture of lauric and myristic alcohols: from 65 to
    75%, preferably 70 to 75% by weight of lauric and myristic ester salts of glycine betaine, from 1 to 20%, for example from 1 to 9% by weight or from 10 to 20% by weight of alcohols lauric and myristic, from 10 to 20%, preferably from 10 to 15% by weight of organic or inorganic acid and from 1 to 15% by weight of glycine betaine;
    - in the case where the fatty alcohol is oleic alcohol: from 70 to 80%, preferably from 70 to
    75% by weight of oleic ester salt of glycine betaine, from 1 to 20%, for example from 5 to 10% by weight or from 11 to 20% by weight of oleic alcohol, from 5 to 15% by weight d organic or inorganic acid and from 1 to 15% by weight of glycine betaine.
    It was observed that the use of alcohol in default, compared to glycine betaine, in the process according to the invention made it possible to obtain surfactant compositions which, in addition to their lower surface tension, by comparison with the compositions of the prior art, exhibited better solubility in water. These surfactant compositions are thus more fluid and more transparent, which is advantageous in the case where the composition is intended to be sprayed or impregnated on a fibrous support such as wipes.
    Uses The surfactant composition obtained according to the invention has a surface tension value of less than 30 mN / m, or even less than 25 mN / m and generally greater than 20 mN / m, measured according to the NF standard. EN 14370.
    It is thus possible to envisage its use in a variety of applications as a wetting agent, particle dispersant and / or corrosion inhibitor and / or to improve the disinfecting power of antimicrobial substances. It can in particular be used for the manufacture of plastics or of various products intended in particular:
    - treatment and / or cleaning of the body, plants, textiles or hard surfaces, in particular cosmetic products, such as shampoos, liquid soaps, bubble baths and shower gels; vehicle wash products such as automobiles, trucks, trains, buses or airplanes; household products such as detergents for windows, wall surfaces, floors or dishes; care products for textiles; industrial cleaning products; fiber sizing products; phytosanitary products; pigmented products such as paints or varnishes;
    - water treatment;
    - the coating of roads, in particular bituminous emulsions;
    - Oil extraction.
    In the case of water treatment, the composition according to the invention makes it possible to take off the biofilm without destroying the effectiveness of ion exchange resins, unlike conventional cationic surfactants which also have a non-negligible environmental impact taking into account their lack of biodegradability, or their slower biodegradability. This ability to take off biofilms can also be used in petroleum extraction processes.
    In cosmetic applications, the composition according to the invention is compatible with conventional anionic surfactants and improves the creaminess 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 confer electrostatic properties on the surface of the plastic, without affecting its recycling capacities taking into account its biobased nature.
    When used in the manufacture of phytosanitary products, the composition according to the invention makes it possible to improve the persistence of the active materials and the water resistance of the products such as herbicides, pesticides or modifying agents. plant growth, which can be used in smaller quantities. This composition can thus be added, in diluted form to 25% in water, at a rate of 0.4% by weight, in a product containing an acid medium, for example.
    The composition according to the invention can also be used in a process for extracting, storing, storing or refining petroleum to limit corrosion of the equipment. In this application, it can be added to petroleum up to 500 to 1000 ppm, for example.
    The invention also relates to a product, for example chosen from those described above, comprising a composition according to the invention and at least one compound chosen from: anionic surfactants, nonionic surfactants, antimicrobial agents and their mixtures. Examples of anionic surfactants are: sulfate salts of ethoxylated fatty alcohols, sulfosuccinates, sarcosinates, alkyl- and dialkylphosphates, fatty acid soaps and mixtures thereof. The nonionic surfactants can for example be chosen from: esters of fatty acids and of polyols such as esters of fatty acids and of glycerol optionally polyethoxylated, esters of fatty acids and of sorbitan optionally polyethoxylated, esters of fatty acids and polyoxyethylene, esters of fatty acids and sucrose such as sucrose stearate, ethers of fatty alcohol and polyoxyethylene, ethers of fatty alcohols and sugar, in particular alkylpolyglucosides (APG), polysiloxanes modified polyethers, and mixtures thereof. The antimicrobial agents can be chosen from quaternary ammoniums, aldehydes (such as glutaraldehyde and formaldehyde), ethanol, halogenated derivatives, oxidants, phenolic compounds, parabens, isothiazolones (or isothiazolinones), benzoates, imidazoline, hydantoin, guanidine, organic acids such as lactic acid, and mixtures thereof.
    This product is advantageously in the form of an aqueous solution or an aqueous gel. Alternatively, it may be in the form of an oil-in-water or water-oil emulsion or even a paste. In any event, the aqueous phase contained in this product advantageously has a pH ranging from 1 to 8, in particular from 1 to 5. This product can be packaged in any device suitable for the intended use and in particular in a pump bottle , a tube, a jar, an aerosol device or a wipe.
    It advantageously contains from 0.1 to 25% by weight, for example from 1 to 10% by weight, of surfactant composition according to the invention.
    The product according to the invention may also comprise, in addition to the aforementioned antimicrobial agents and surfactants, and depending on the application envisaged, at least one ingredient chosen from: phytosanitary or cosmetic active agents, enzymes, chelating agents, thickeners, fatty substances (oils, waxes and / or pasty), fillers, preservatives, pigments and dyes, antioxidants, optical brighteners, and mixtures thereof.
    Examples The invention will be better understood in the light of the following examples, which are given purely by way of illustration and are not intended to limit the scope of the invention, defined by the appended claims.
    Example 1: Synthesis of a surfactant composition according to the invention [0070] Glycine betaine (1.0 eq) and a fatty alcohol are introduced into a reactor. The set temperature at the level of the mixture is fixed at 170 ° C and the pressure is reduced to 30 mbar. Once the pressure and temperature set points have been reached, a 70% methanesulfonic acid solution (1.6 eq) is added to the reaction mixture. As soon as the addition is complete, the set temperature is reduced to 150 ° C and the pressure is maintained at a value of 10 to 600 mbar, depending on the alcohol used. Four hours after the start of the introduction of the acid, the reaction mixture is allowed to cool to 80 ° C., then the product is recovered, cooled to room temperature, and the reaction yield is determined by N NMR.
    This process was carried out using, as fatty alcohol, either lauric alcohol, or a mixture of lauric alcohol and myristic alcohol, or oleic alcohol. These were used either in excess (1.4 equivalent) or in default (0.9 equivalent) compared to glycine betaine.
    The surface tension measurement was carried out according to standard NL EN 14370, using a Krüss tensiometer with a platinum ring suspended horizontally. Before each measurement, the ring is thoroughly cleaned and flame dried. The sample cup is a conical PTEE container placed in a temperature-controlled enclosure at 25 ° C. The sample is prepared with Milli-Q water and continuously stirred with a magnetic bar before each measurement.
    The products obtained had the following mass composition:
    [Tables 1]
    Excess alcohol Alcohol in default Component R = C12: 0 R = C12: 0 /C14: 0 R = C18: 1 R = C12: 0 R = C12: 0 /C14: 0 R = C18: 1 Betainyl ester mesylate 74% 72% 72% 77% 70% 72% Residual fatty alcohol 11% 13% 16% 1% 4% 6% Residual acid 12% 11% 9% 14% 14% 12% Glycine betaine residual 3% 4% 3% 8% 12% 10% Yield 1 hour 93% 90% 92% 93% 86% 83% Surface tension atCMC(mN / m) 21 at pH3 21.8 at pH 3 29 at pH 3 21 at pH3 21.8 at pH 3 29h3
    (1) Calculated with respect to glycine betaine (excess alcohol) or fatty alcohol (alcohol in default) It is observed that the reaction yield is always greater than or equal to 75%. Furthermore, the surface tension at CMC of the compositions obtained according to the invention does not depend on the quantity of fatty alcohol used, which makes it possible to use a lower quantity of alcohol. Insofar as the latter has a significant impact on the cost of the process, this is an undeniable economic advantage of the process according to the invention. In addition, the residual fatty alcohol reducing the solubility in water of the surfactant compositions, the use of alcohol in default in the process according to the invention makes it possible to obtain more fluid and transparent compositions.
    By comparison, the products described in documents WO 2013/188508 and US7,829,521 and in the publication by Goursaud et al (Green Chem., 2008, 10, 310-320) had the following characteristics:
    [Tables!]
    Component R = C12: 0 R = C12: 0 / C14:0 R = C18: 1Goursaud WO'508 WO'508 US'521 Goursaud Yield 95% - - 85% 85% Surface tension at CMC (mN / m) 32 27 24 36.6 37
    These products were obtained, according to these documents, by reacting betaine glycine with 1.0 to 1.5 equivalents of alcohol in the presence of 2 to 3 equivalents of methanesulfonic acid, at a temperature of 120 to 140 ° C and under a pressure of 30 to 100 mbar, for a reaction time of 6 to 8 hours. The products obtained by Goursaud and in US'521 have also been purified.
    It thus appears that the products obtained according to the invention, using a lower amount of methanesulfonic acid and a higher temperature, have, in a totally unexpected manner, improved properties, making it possible to envisage their use in a diversity of applications. These products are also obtained with a yield of the same order of magnitude (greater than 80%) as those of the prior art but in a shorter time, which represents an undeniable advantage from the industrial point of view.
    EXAMPLE 2 Formulations Several types of products can be prepared using surfactant compositions according to the invention, based respectively on lauric acid ester (GBE Cl2), on a mixture of lauric and myristic acids ( GBE C12 / 14) or oleic acid (GBE C18: 1).
    Household detergent 80% Lactic acid 2.00% [0084] GBE C12 / 14 0.40% [0085] Hydroxyethyl cellulose 0.30% [0086] Chelating agent 0.20% [0087] Fragrance 0, 20% [0088] Dye 0.01% [0089] Deionized water qs 100.00% [0090] This product can be used for cleaning hard surfaces.
    Shampoo
    [0092] GBEC 18: 1 30.00% [0093] Coconut diethanolamide 5.00% [0094] Citric acid qs pH 5 [0095] conservative qs [0096] Water qs 100.00% [0097] WC product [0098] Phosphoric acid 85% 5.90% [0099] Hydrochloric acid 37% 13.50% [0100] GBEC 12: 0 3.00% [0101] Perfume 0.20% [0102] Dye 0.01% [0103] Water qs 100.00% [0104] Hair conditioner [0105] GBE C12: 0 / C14: 0 3.00% [0106] Cetyl / stearyl alcohols 5.00% [0107] Citric acid qs pH 2.5-3.0 [0108] 0.25% fragrance [0109] Dye 0.02% [ΟΠΟ] Preservative 0.01% [YES] Water qs 100.00% [0112] Ohvtosanitary adjuvant (emulsifiable concentrate) [0113] GBEC 12: 0 6.00% [0114] GBEC18: 1 8.00% [0115] Anti-foaming agent 0.10% [0116] Rapeseed methyl ester qs 100.00%
    Claims [Claim 1] Process for the preparation of a surfactant composition, comprising the successive stages consisting in:1. reacting betaine glycine or one of its salts with a linear or branched fatty alcohol, saturated or unsaturated, containing from 8 to 22 carbon atoms, in the presence of an organic or inorganic acid;2. cooling the reaction medium to a temperature of 20 to 90 ° C; and3. recover the surfactant composition thus obtained,characterized in that the organic or inorganic acid represents from 1.1 to 2.0 molar equivalent relative to the number of moles of glycine betaine and in that the reaction is carried out at a temperature of 150 to 180 ° C. [Claim 2] Method according to claim 1, 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 benzene sulfonic acid, paratoluene sulfonic acid, camphosulfonic acid, alkylsulfonic acids, such as triflic acid, methanesulfonic acid, ethanesulfonic acid, decylsulfonic acid, laurylsulfonic acid, sulfosuccinic acid, and mixtures thereof, preferably the acid is methanesulfonic acid. [Claim 3] Process according to claim 1 or 2, characterized in that the fatty alcohol is chosen from the group consisting of: caprylic alcohol (C8: 0), decyl alcohol (C10: 0), undecyl alcohol (Cl 1: 0), lauric alcohol (C12: 0), myristic alcohol (C14: 0), cetyl alcohol (C16: 0), palmitoleic alcohol (Cl6: 1), stearic alcohol ( Cl8: 0), oleic alcohol (C18: 1), linoleic alcohol (C18: 2), linolenic alcohol (C18: 3), arachidic alcohol (C20: 0), arachidonic alcohol ( C20: 4), behenyl alcohol (C22: 0), hexyldecanol, octyldodecanol and mixtures thereof. [Claim 4] Method according to any one of Claims 1 to 3, characterized in that 0.8 to 2 equivalents are used, for example from 0.9 to 1.0
    权利要求:
    Claims (1)
    [1" id="c-fr-0001]
    Claims [Claim 1] Process for the preparation of a surfactant composition, comprising the successive stages consisting in:1. reacting betaine glycine or one of its salts with a linear or branched fatty alcohol, saturated or unsaturated, containing from 8 to 22 carbon atoms, in the presence of an organic or inorganic acid;2. cooling the reaction medium to a temperature of 20 to 90 ° C; and3. recover the surfactant composition thus obtained,characterized in that the organic or inorganic acid represents from 1.1 to 2.0 molar equivalent relative to the number of moles of glycine betaine and in that the reaction is carried out at a temperature of 150 to 180 ° C. [Claim 2] Method according to claim 1, 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 benzene sulfonic acid, paratoluene sulfonic acid, camphosulfonic acid, alkylsulfonic acids, such as triflic acid, methanesulfonic acid, ethanesulfonic acid, decylsulfonic acid, laurylsulfonic acid, sulfosuccinic acid, and mixtures thereof, preferably the acid is methanesulfonic acid. [Claim 3] Method according to claim 1 or 2, characterized in that the fatty alcohol is chosen from the group consisting of: caprylic alcohol (C8: 0), decyl alcohol (C10: 0), undecyl alcohol (Cl 1: 0), lauric alcohol (C12: 0), myristic alcohol (C14: 0), cetyl alcohol (C16: 0), palmitoleic alcohol (Cl6: 1), stearic alcohol ( Cl8: 0), oleic alcohol (C18: 1), linoleic alcohol (C18: 2), linolenic alcohol (C18: 3), arachidic alcohol (C20: 0), arachidonic alcohol ( C20: 4), behenyl alcohol (C22: 0), hexyldecanol, octyldodecanol and mixtures thereof. [Claim 4] Method according to any one of Claims 1 to 3, characterized in that 0.8 to 2 equivalents are used, for example from 0.9 to 1.0
    equivalent, or alternatively from 1.1 to 1.8 equivalent, preferably in this case from 1.2 to 1.6 equivalent and, better, from 1.3 to 1.5 equivalent of fatty alcohol, for 1 equivalent of glycine betaine. [Claim 5] Process according to any one of Claims 1 to 4, characterized in that 1.3 to 1.9 equivalent, and preferably 1.5 to 1.7 equivalent of organic or inorganic acid, are used for 1 equivalent glycine betaine. [Claim 6] Surfactant composition obtained according to the process according to any one of Claims 1 to 5. [Claim 7] Composition according to Claim 6, characterized in that it contains the following constituents:at. from 65 to 85% by weight, preferably from 70 to 80% by weight, of glycine ester salt of betaine,b. from 1 to 20% by weight, for example from 1 to 9% by weight or from 10 to 20% by weight, of fatty alcohol,vs. from 1 to 20% by weight, for example from 5 to 15% by weight of organic or inorganic acid, andd. from 1 to 20% by weight, for example from 2 to 15% by weight, of glycine betaine,relative to the total weight of these four constituents. [Claim 8] Composition according to Claim 7, characterized in that these constituents represent in total from 90 to 100%, and preferably from 95 to 100% of the weight of the composition. [Claim 9] Composition according to any one of Claims 6 to 8, characterized in that it has a surface tension value of less than 30 mN / m, or even less than 25 mN / m and generally greater than 20 mN / m, measured according to standard NF EN 14370. [Claim 10] Use of the surfactant composition according to any one of Claims 6 to 9 as a wetting agent, particle dispersing agent and / or corrosion inhibitor and / or for improving the disinfecting power and / or the persistence of the disinfecting effect of antimicrobial substances. [Claim 11] Use of the composition according to any one of Claims 6 to 9 for the manufacture of plastics or of products intended:• treatment and / or cleansing of the body, plants orhard surfaces, in particular cosmetic products, vehicle wash products, household products,
    industrial cleaning products, fiber sizing products and phytosanitary products;
    • water treatment;
    • road surfacing; or • petroleum extraction.
    [Claim 12] Product comprising the composition according to any one of claims 6 to 9 and at least one constituent chosen from: (a) anionic surfactants, nonionic surfactants and their mixtures and / or (b) antimicrobial agents.
    类似技术:
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    同族专利:
    公开号 | 公开日
    CN113383061A|2021-09-10|
    WO2020109710A1|2020-06-04|
    BR112021009583A2|2021-08-17|
    CA3120188A1|2020-06-04|
    EP3887493A1|2021-10-06|
    FR3088930B1|2021-11-19|
    US20220024855A1|2022-01-27|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US7829521B2|2004-05-04|2010-11-09|Eiffage Travaux Publics|Surfactant composition method for production thereof and cosmetic comprising said composition|
    WO2009150369A2|2008-05-21|2009-12-17|Ceca Sa|Additives for bituminous products|
    WO2013188508A1|2012-06-13|2013-12-19|S. C. Johnson & Son, Inc.|Green glycine betaine derivative compounds and compositions containing same|
    WO2015003968A1|2013-07-10|2015-01-15|L'oreal|Glycine-betaine amide and ester derivatives as deodorising active substances, and cosmetic compositions containing same|
    WO2015078890A1|2013-11-28|2015-06-04|Societe D'exploitation De Produits Pour Les Industries Chimiques Seppic|Novel emulsifying composition with cationic nature|WO2022018362A1|2020-07-22|2022-01-27|Surfactgreen|Use of a glycine betaine derivative as a pediculicidal agent|
    FR3112946A1|2020-07-31|2022-02-04|Surfactgreen|Use of a cosmetic composition containing a glycine betaine derivative for protecting the skin against external aggressions|
    法律状态:
    2019-11-18| PLFP| Fee payment|Year of fee payment: 2 |
    2020-05-29| PLSC| Publication of the preliminary search report|Effective date: 20200529 |
    2020-11-23| PLFP| Fee payment|Year of fee payment: 3 |
    2021-11-08| PLFP| Fee payment|Year of fee payment: 4 |
    优先权:
    申请号 | 申请日 | 专利标题
    FR1871892A|FR3088930B1|2018-11-27|2018-11-27|Process for preparing a surfactant composition based on glycine betaine ester salt and composition thus obtained|FR1871892A| FR3088930B1|2018-11-27|2018-11-27|Process for preparing a surfactant composition based on glycine betaine ester salt and composition thus obtained|
    CN201980077792.3A| CN113383061A|2018-11-27|2019-11-25|Process for the preparation of a surfactant composition based on a glycine betaine ester salt and composition thus obtained|
    EP19868174.4A| EP3887493A1|2018-11-27|2019-11-25|Process for preparing a surfactant composition based on a glycine betaine ester salt, and composition thus obtained|
    CA3120188A| CA3120188A1|2018-11-27|2019-11-25|Process for preparing a surfactant composition based on a glycine betaine ester salt, and composition thus obtained|
    US17/296,999| US20220024855A1|2018-11-27|2019-11-25|Process for preparing a surfactant composition based on a glycine betaine ester salt, and composition thus obtained|
    BR112021009583-7A| BR112021009583A2|2018-11-27|2019-11-25|method of preparing a glycine betaine ester salt-based surfactant composition and composition thus obtained|
    PCT/FR2019/052801| WO2020109710A1|2018-11-27|2019-11-25|Process for preparing a surfactant composition based on a glycine betaine ester salt, and composition thus obtained|
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