POLYESTERAMINES ET POLYESTERQUATS

Description

[0001] The present invention relates to compounds having polyesteramine and polyesterquat structures. Such structures are novel, and compounds with such a structure can be used in many fields of application, for example, as surfactants, corrosion inhibitors, and the like.

[0002] Fatty alkylamines and quaternary ammonium compounds are particularly useful chemicals employed in a wide variety of industries. Among their many possible applications, they can be used as biocides, hair care products, textile softeners, or antistatic additives for plastics. Their strong adsorption properties on mineral or metallic surfaces or other solid particles make them particularly interesting as wetting agents, corrosion inhibitors, collectors for ore enrichment, acid etching additives for phosphate rock, fertilizers and surface or internal treatment additives for mineral salts, anti-caking agents for hydrates, clay modifiers, lubricant additives, or adhesion promoters.They may also exhibit viscosifying, emulsifying or stabilizing properties useful for the oil and gas industry (demulsifying agents, surfactants for increased oil recovery, surfactants for fracture fluids, surfactants for acidifying fluids, surfactants for improving the injectivity of produced water, surfactants for drilling muds), the bitumen emulsion or detergent industry.

[0003] These fatty alkylamines and quaternary ammonium compounds are well known in industry, and research continues to find new products. Over the past 30 years, another family of compounds containing heavier molecular weight nitrogen has been described in the literature. These compounds are amines and quaternary ammonium compounds with a polymeric or oligomeric structure.

[0004] For example, patent EP0035263 describes a reaction product between a dicarboxylic acid and an ethoxylated fatty amine, said product being used as a fabric softener. In patent EP0144975, the same reaction product can be quaternized and used as a hair conditioner.

[0005] Application WO2008 / 089906 describes a reaction product of a fatty acid with a diacid and an (alkyl)polyethanolamine, said reaction product being subsequently quaternized and used as a collector for the flotation of non-sulfide ores.

[0006] Similarly, JP08-291281 describes reaction products of C1-C22 alkylamines alkoxylated with diacids (or anhydrides) followed by a quaternary reaction, said products being used as an antistatic agent in composite resins, particularly for the automotive industry.

[0007] WO 2011 / 147855 further describes a reaction product of a fatty alcohol with a diacid and an (alkyl)polyethanolamine, optionally followed by a partial or complete quaternary reaction, such a product being typically used for the flotation of silicates. The fatty alcohol can be replaced by an alkylated fatty amine having a single alkoxylated chain with a single terminating -OH group.

[0008] Therefore, there is still a need for new oligomeric compounds or cationic polymers for use in the application areas listed above, said compound being more easily prepared, more stable, less expensive to synthesize and also exhibiting better environmental properties in terms of toxicity and biodegradability, and having improved technical performance.

[0009] Therefore, the present invention relates to a compound that can be obtained by the esterification condensation of: A / an alkoxylated fatty amine of formula (I), or of the partial or total quaternary product of said alkoxylated fatty amine of formula (I): in which: R 1< is selected from a hydrocarbyl group having 8 to 24 carbon atoms, preferably 10 to 24, more preferably 12 to 24 carbon atoms, and a group of formula R 4< -O-(A'O) w -T-, in which R 4< is a hydrocarbyl group having 8 to 24 carbon atoms, preferably 12 to 24 carbon atoms, w represents an integer in the range of 0 to 20, preferably 0 to 10, more preferably 0 to 6, and even more preferably 0 to 4, A'O is an alkylenoxy group containing 2 to 4 carbon atoms, preferably 2 or 3 carbon atoms, more preferably 2 carbon atoms;T is an alkylene with 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, preferably any 2 or 3 carbon atoms; AO is an alkylenoxy group containing 2 to 4 carbon atoms, preferably 2 or 3 carbon atoms, more preferably 2 carbon atoms; B is chosen from a C1-C4 alkyl, aryl, or arylalkyl group (e.g., phenyl, phenylalkyl, such as benzyl); m is an integer from 1 to 20, preferably from 1 to 10, more preferably from 1 to 6, and even more preferably from 1 to 4, inclusive; n is an integer from 1 to 20, preferably from 1 to 10, more preferably from 1 to 6, and even more preferably from 1 to 4, inclusive; s is 1, 2, or 3, preferably 2 or 3, and y is an integer from 0 to 5, preferably from 0 to 3, more preferably y is 0 or 1, even more preferably y is 0, B / with a dicarboxylic acid, or a derivative thereof, of formula (II): ;in which D is chosen from -F, -Cl, Br and -OR3<, where R3< is hydrogen or a C1-C4 alkyl group, R2< is chosen from the group consisting of: ∘ a direct bond, ∘ a linear or branched hydrocarbon chain, saturated or unsaturated at C1-C20 optionally substituted by one or more -OH group(s), preferably an alkylene radical of formula -(CH2)z-, in which z is an integer from 1 to 20, preferably from 1 to 10, preferably from 2 to 6, and preferably 4, a substituted alkylene radical, said alkylene radical being substituted by 1 or 2 -OH groups, an alkenylene radical having from 1 to 20, preferably from 1 to 10 carbon atoms, a substituted alkenylene radical, said radical alkenylene being substituted by 1 or 2 methyl and / or methylene groups, ∘ a cycloalkylene group,∘ cycloalkenylene and ∘ arylene C / with an (alkyl)alkanolamine derivative of formula (III) or of the partial or total quaternary product of said (alkyl)alkanolamine derivative of formula (III): , wherein: A"O represents an alkylenoxy group containing from 2 to 4 carbon atoms, preferably 2 or 3 carbon atoms, more preferably 2 carbon atoms; u represents an integer from 1 to 20, preferably from 1 to 10, more preferably from 1 to 6, and even more preferably from 1 to 4, inclusive; u' represents an integer from 1 to 20, preferably from 1 to 10, more preferably from 1 to 6, and even more preferably from 1 to 4, inclusive; R 7< is chosen from a hydrocarbyl group having 1 to 7, preferably 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, an aryl or arylalkyl group (for example, a phenyl or naphthyl group), a group of formula H-(OA") v - (where v represents an integer from 1 to 20, preferably from 1 and 10, more preferably between 1 and 6, and even more preferably between 1 and 4, inclusive limits), HO(CH 2 ) q - and a group of formula (IV) in which R 8< and R 9<, identical or different, are chosen from a hydrocarbyl group having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, and q is an integer from 1 to 10, preferably from 2 to 6 inclusive, and preferably among all q is 2 or 3, or R 8< and R 9<, together with the nitrogen atom to which they are bonded, form a ring of 5, 6, or 7 atoms, optionally comprising one or more heteroatom(s) chosen from oxygen, nitrogen, or sulfur.

[0010] In this description, "hydrocarbyl" means a linear or branched, saturated or unsaturated hydrocarbyl chain.

[0011] In a preferred embodiment, compounds of the invention can be obtained by esterification condensation as defined above, wherein, in the fatty amine of formula (I), R<1> comprises 8, or more than 8, carbon atoms, typically from 8 to 24 carbon atoms, preferably from 10 to 24, more preferably from 12 to 24 carbon atoms, inclusive, and in the (alkyl)alkanolamine derivative of formula (III), R<7> comprises 6 carbon atoms or less, typically from 1 to 6 carbon atoms, more preferably from 1 to 4 carbon atoms, inclusive.

[0012] In a further preferred embodiment, compounds of the invention can be obtained by esterification condensation as defined above, wherein, in the fatty amine of formula (I) and in the (alkyl)alkanolamine derivative of formula (III), R1< and R7< are such that the difference in the number of carbon atoms they comprise is greater than 2, typically from 2 to 23, preferably from 5 to 23, more preferably from 10 to 23, inclusive.

[0013] It is understood that dicarboxylic acids or derivatives thereof of formula (II) further include their corresponding anhydride forms. It is further understood that when the alkylenoxy chain contains more than one alkylenoxy group, the alkylenoxy groups may be identical or different. Similarly, when y is greater than one, the repeating motifs may be identical or different.

[0014] The present invention further relates to the compound of the present invention (which can be obtained by reaction between the alkoxylated fatty amine of formula (I), the dicarboxylic acid or a derivative thereof of formula (II), and the (alkyl)alkanolamine derivative of formula (III)), after a further reaction in which some or all of the nitrogen atoms are quaternized by reaction with a reagent of formula R 5< X, in which R 5< is selected from a C 1-C 6 hydrocarbyl group, preferably a C 1-C 4 alkyl group, phenyl and phenylalkyl, such as benzyl, and X is any leaving group known in the art and, preferably, X is generally selected from halogens, sulfates, carbonates, and the like.

[0015] Formula (1) below is a possible representation of the compounds of the present invention, as described above, which can be obtained by the esterification condensation of the alkoxylated fatty amine of formula (I) (comprising its partial or total quaternary product), with the dicarboxylic acid, or a derivative thereof, of formula (II), and with a derivative of (alkyl)alkanolamine of formula (III) (comprising its partial or total quaternary product).

[0016] Therefore, and in a second aspect, the present invention relates to a compound of general formula (1): in which: R2<, R5<, and X are as defined above, test 0 or 1. p is an integer in the range of 1 to 15, preferably from 1 to 10, more preferably from 1 to 5, inclusive. QO represents an alkylenoxy group containing from 2 to 4 carbon atoms, preferably 2 or 3 carbon atoms, more preferably 2 carbon atoms, given that all the Qs present in the compound of formula (1) may be identical or different. q1, q2, q3, q4, identical or different from each other, each represent an integer from 1 to 20, preferably from 1 to 10, more preferably from 1 to 6, and even more preferably from 1 to 4, inclusive. Each group R10<, independently of the others, represents R7< as previously defined or a group R1< -(G)y- in which R1< and y are such as previously defined and G represents a group of formula (IV): in which B, R 5 , X, t and s are such as defined above, the group (CH 2 ) s is a spacer between the two nitrogen atoms to which it is bonded, knowing that at least one of the R groups 10 represent 7 , and at least one other of the R groups 10 represent 1 -(G) y - and each t is independent of the others.

[0017] In a particular embodiment, the alkoxylated fatty amine of formula (I) has the formula (IA): which is the alkoxylated fatty amine of formula (I) in which y represents 0, and R 1< , AO, m and n are as defined above, as well as its corresponding partially or totally quaternary derivatives.

[0018] In another particular embodiment, the (alkyl)alkanolamine derivative of formula (III) has formula (IIIA): which is the (alkyl)alkanolamine of formula (III) in which u and u' each represent 1, A"O is ethylenoxy, and R7< is as defined above. In the compound of formula (IIIA) above, R7< is preferably a hydrocarbyl group having 1 to 4 carbon atoms. The compound of formula (IIIA) above further covers its corresponding partially or totally quaternary derivatives.

[0019] The dicarboxylic acid derivative of general formula (II) described may be a dicarboxylic acid or dicarboxylic acid derivative or any anhydride known to those skilled in the art, and typically a dicarboxylic acid, a halide (e.g., a chloride) of a dicarboxylic acid, a diester of a dicarboxylic acid, or a cyclic anhydride of a dicarboxylic acid. The most suitable derivatives are the dicarboxylic acids and their corresponding cyclic anhydrides.

[0020] Illustrative examples of dicarboxylic acid derivatives of general formula (II) include oxalic acid, malonic acid, succinic acid, glutaric acid, glutaconic acid, adipic acid, muconic acid, pimelic acid, phthalic acid and its isomers, tetrahydrophthalic acid, malic acid, maleic acid, fumaric acid, suberic acid, mesaconic acid, sebacic acid, azelaic acid, tartaric acid, itaconic acid, glutinic acid, citraconic acid, brassylic acid, dodecanedioic acid, traumatic acid, thapsic acid, their corresponding acid chlorides, their corresponding methyl or ethyl esters, and their corresponding cyclic anhydrides, and mixtures thereof.

[0021] Preferred dicarboxylic acid derivatives of general formula (II) are chosen from among those mentioned above: oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, phthalic acid and its isomers, tetrahydrophthalic acid, malic acid, tartaric acid, itaconic acid, their corresponding acid chlorides, their corresponding methyl or ethyl esters, and their corresponding cyclic anhydrides, as well as mixtures thereof.

[0022] Alkoxylated fatty amines of formula (I) are available or can be prepared according to a process known in the literature, and can, for example, be easily prepared by alkoxylation of fatty amines of formula (a): in which R 1< , B, s and y are such as defined above.

[0023] Illustrative examples of fatty amines adapted according to formula (a) for use as starting materials for the preparation of alkoxylated fatty amines of formula (I) include, but are not limited to, fatty amines of formula (a1) in which y represents 0 and fatty amines of formula (a2) in which y represents 1, s represents 3 and B represents methyl: R1 < -NH2 (a1) in which R 1< is such as defined above.

[0024] Particular examples of amines of formula (a1) are amines of formula (a3): R4<-OT-NH2(a3), in which R4<, and T are as defined above and w is 0.

[0025] More specific examples of the amines of formula (a) mentioned above include, but are not limited to, 2-ethylhexylamine, 2-propylheptylamine, n-octylamine, n-decylamine, n-dodecylamine, (coco-alkyl)amine, (palm oil-alkyl)amine, n-tetradecylamine, n-hexadecylamine, n-octadecylamine, oleylamine, (tallow-alkyl)amine, (hydrogenated tallow-alkyl)amine, (rapeseed-alkyl)amine, (soybean-alkyl)amine, erucylamine, N-(n-decyl)-N-methyltrimethylenediamine, N-(n-dodecyl)-N-methyltrimethylenediamine, N-(coco-alkyl)-N-methyltrimethylenediamine, N-(rapeseed-alkyl)-N-methyl-trimethylenediamine, N-(soybean-alkyl)-N-methyl-trimethylenediamine, N-(tallow-alkyl)-N-methyl-trimethylenediamine, N-(hydrogenated tallow-alkyl)-N-methyl-trimethylenediamine, N-erucyl-N-methyltrimethylenediamine and isotridecyloxypropylamine, as well as mixtures thereof.

[0026] According to one embodiment of the invention, the amines mentioned above are fatty amines obtained from oil or natural acids (vegetable or animal) and mixtures thereof, for example coconut fatty acids, tallow fatty acids, rapeseed oils, soybean oils and palm oils.

[0027] These fatty amines are then typically alkoxylated with 2 to 40, preferably 2 to 20, more preferably 2 to 12, and even more preferably 2 to 8 EO (ethylene oxide motifs), and / or 2 to 40, preferably 2 to 20, more preferably 2 to 12, and even more preferably 2 to 8 PO (propylene oxide motifs), and / or 2 to 40, preferably 2 to 20, more preferably 2 to 12, and even more preferably 2 to 8 BO (butylene oxide motifs). Blocks with EO are generally added first and PO and / or BO last, or blocks with PO and / or BO added first and EO last, or with mixtures of EO and PO and / or BO to produce alkoxylated products randomly of general formula (I). Alkoxylation can be carried out by any suitable process known in the art using, for example, an alkali catalyst, such as potassium hydroxide (KOH), or an acid catalyst or even without a catalyst.

[0028] Examples of marketed formula (I) products include Noramox®< SD20, Noramox®< SD15, Noramox®< S11, Noramox®< S5, Noramox®< S7, Noramox®< S2, Noramox®< SH2, Noramox®< O2, Noramox®< O5, Noramox®< C2, Noramox®< C5, and Noramox®< C15. All of these marketed products are available from CECA SA. Other examples of marketed formula (I) products include Tomamine®< E-17-5 and Tomamine®< ET-2, marketed by Air Products.

[0029] (Alkyl)alkanolamine derivatives of formula (III) are available or can be prepared according to a process described in the literature. Illustrative examples of suitable (alkyl)alkanolamine derivatives of formula (III) include, but are not limited to, triethanolamine, methyldiethanolamine, ethyldiethanolamine, propyldiethanolamine, butyldiethanolamine, isobutyldiethanolamine, pentyldiethanolamine, phenyldiethanolamine, hexyldiethanolamine, heptyldiethanolamine, and their corresponding alkoxylation products.

[0030] Other examples of amines suitable as starting materials for the preparation of alkoxylated derivatives of formula (III) include, without limitation, methylamine, ethylamine, propylamines, butylamines, pentylamines, hexylamines, heptylamines, dimethylaminoethylamine, diethylaminoethylamine, dimethylaminopropylamine (DMAPA), diethylaminopropylamine (DEAPA), dipropylaminopropylamine, dibutylaminopropylamine (DBAPA), 1-(3-aminopropyl)-2-pyrolidine, 3-morpholinopropylamine, 1-(3-aminopropyl)piperidine, and 1-(3-aminopropyl)pipecoline. Some of these alkoxylated derivatives of formula (III) are novel and, as such, form part of the present invention.

[0031] A suitable process for preparing the products for use in the present invention includes the steps of mixing at least one compound of formula (II) with at least one compound of formula (III) as defined above and at least one compound of formula (I) as defined above, and conducting a condensation reaction by esterification between the compounds in the mixture.

[0032] As will be apparent to those skilled in the art, other processes in which compounds of formula (I), (II), and (III) react sequentially with one another in different orders are also suitable. For example, it is possible to conduct a condensation reaction by esterification between compounds of formula (I) and (II) first, and then to conduct another condensation reaction by esterification of this condensation product with a compound of formula (III) in a further step. Another suitable process involves conducting a condensation reaction by esterification between compounds of formula (II) and (III) first, and then to conduct another condensation reaction by esterification of this condensation product with a compound of formula (I) in a further step.

[0033] Other alternative processes include conducting a condensation reaction by esterification, such as, for example, between: a. a condensation reaction product between compounds of formula (II) and (III) and b. a condensation reaction product between compounds of formula (I) and (II) c. optionally conducting another condensation reaction by esterification of the reaction product compounds of step a and step b above together with at least one compound of formula (I) and / or formula (II) and / or formula (III).

[0034] More generally, the compounds of formula (1) of the present invention can be prepared from esterification condensation reaction(s) in which at least one compound of formula (I) and at least one compound of formula (II) and at least one compound of formula (III) react in one or more simultaneous and / or sequenced and / or alternating esterification condensation reaction(s).

[0035] The esterification condensation reaction occurring between compounds of formula (II) and formulas (I) and (III) is a reaction known as such in the art. The reaction is preferably carried out in the presence of an esterification catalyst, such as a Brønstedt acid or a Lewis acid, for example methanesulfonic acid, para-toluenesulfonic acid, hypophosphoric acid, citric acid or boron trifluoride (BF3).

[0036] When a dicarboxylic acid derivative of formula (II), in which D is OR 3 < , is used, the reaction is a transesterification which, alternatively, can be carried out in the presence of an alkali catalyst. Alternatively, other conventional techniques known to those skilled in the art can be used with other derivatives of dicarboxylic acids, for example, from their anhydrides or acid chlorides.

[0037] As will be apparent to those skilled in the art, the various esterification reactions can be carried out with or without the addition of solvents. If solvents are present during the reaction, they must be inert to esterification, for example, toluene or xylene, and the like.

[0038] The esterification condensation reaction between components (I), (II), and (III) can be carried out at any temperature under known operating conditions and, for example, typically in the range of 60°C to 300°C, preferably from 120°C to 280°C, and generally for a duration ranging from 1 hour to several hours, preferably from 2 hours to 20 hours. The esterification condensation reaction can be carried out at atmospheric pressure; alternatively, the reaction can optionally be carried out at a reduced pressure, for example, from 500 Pa to 20,000 Pa.

[0039] In a specific embodiment of the present invention, the molar ratio between reactants [(I) + (III)] and (II) is 2:1 to 1:2, preferably 1.5:1 to 1:1.5, and most preferably 1.4:1 to 1:1.4.

[0040] According to another specific embodiment of the present invention, the molar ratio between reactants [(I) + (III)] and (II) is 2:1 to 1:1, preferably 2:1 to 1.2:1, and preferably among all 2:1 to 1.3:1.

[0041] According to another additional embodiment, the molar ratio between (I) and (III) is 15:1 to 1:15, preferably 10:1 to 1:10, more preferably 4:1 to 1:4, and most preferably 2:1 to 1:2.

[0042] When a quaternary product is desired, the preparation process may further include at least one step consisting of the addition of an alkylating agent to the condensation reaction product and the carrying out of said quaternary reaction of the condensation product, according to techniques known in art.

[0043] As such, when all the t's are 0 in formula (1), the product is a tertiary polyesteramine compound, and when all the t's are 1, the product is a quaternary polyester polyammonium compound, resulting from the quaternarization of the compound in which t is 0. As will appear to the person skilled in the art, when some of the t's are 0 and some of the t's are 1, the product is a partially quaternarized polyesteramine compound.

[0044] For the quaternary reaction step, preferred alkylating agents are chosen from compounds of formula R 5< X. Illustrative examples of such alkylating agents include, but are not limited to, methyl chloride, methyl bromide, methyl iodide, dimethyl sulfate, diethyl sulfate, dimethyl carbonate and benzyl chloride, the preferred alkylating agents of all being methyl chloride, dimethyl sulfate, diethyl sulfate or benzyl chloride and mixtures thereof, preferably methyl chloride and / or dimethyl sulfate.

[0045] According to one variant, quaternarization can be carried out on the fatty amine of formula (I) and / or on the (alkyl)alkanolamine derivative of formula (III) before conducting the esterification condensation reaction(s) with the dicarboxylic acid or a derivative thereof of formula (II). Other variants include quaternarization of intermediate compounds obtained during sequential or alternating esterification condensation reactions. One or more total or partial quaternarization reactions can be carried out after any of these intermediate steps.

[0046] Quaternary reactions are generally carried out in water and / or in one or more organic solvents, such as ethanol, isopropanol (IPA), ethylene glycol monobutyl ether, di(ethylene glycol) monobutyl ether (BDG), monoethylene glycol (MEG), diethylene glycol (DEG), or mixtures thereof. Preferred solvents include isopropanol (IPA), ethanol, and mixtures thereof.

[0047] The quaternary reaction temperature is appropriately in the range of 20 °C to 100 °C, preferably at least 40 °C, more preferably at least 50 °C, and most preferably at least 55 °C, and preferably at most 90 °C. The quaternary reaction is typically carried out for a duration ranging from several tens of minutes to several tens of hours, preferably from one hour to 100 hours, more preferably from one hour to 30 hours.

[0048] The quaternary reaction can be partial or complete. Monitoring of the quaternary reaction is generally carried out by observing the decrease in the total alkalinity of the reaction medium. "Total quaternary" is achieved when the total alkalinity is less than or equal to 0.2 meqlg, preferably less than or equal to 0.1 meqlg, and more preferably less than or equal to 0.05 meqlg, as measured by titration with hydrochloric acid.

[0049] In one embodiment, preferred compounds of formula (1) are those in which: R2< is chosen from the group consisting of a divalent hydrocarbyl radical having from 1 to 10, preferably from 2 to 6, and preferably from all 4 carbon atoms, inclusive, when R10< is R7<, R7< is chosen from a hydrocarbyl group having 1 to 4 carbon atoms, preferably 1 to 2 carbon atoms and preferably from all R7< is methyl, when R10< is R1< -(G)y-, y = 0 and R1< is chosen from a hydrocarbyl group having 8 to 24 carbon atoms, preferably 12 to 24 carbon atoms, QO represents an ethoxy group and p, q1, q2, q3, q4, t, R5< are as defined above.

[0050] According to another embodiment, preferred compounds of formula (1) are those in which all the "t"s are equal to 1, i.e. all nitrogen atoms are quaternized (meaning "total quarternarization"), all other variable groups and integers being as defined above.

[0051] According to another embodiment, preferred compounds of formula (1) are those in which all "t"s are equal to 1, and R 5< is chosen from methyl and ethyl, all other variable groups and integers being such as defined above.

[0052] According to another additional embodiment, preferred compounds of formula (1) are those in which all "t"s are equal to 1, R 5< is chosen from methyl and ethyl, and X is chosen from halogens and sulfates (e.g., methosulfates), all other variable groups and integers being such as defined above.

[0053] According to another embodiment, preferred compounds of formula (1) are those in which q1, q2, q3 and q4, independently of each other, are identical or different, and are chosen from 1, 2, 3, 4, 5 and 6, p is in the range from 1 to 10, inclusive, and all other variable and integer groups are as defined above.

[0054] Compounds of formula (1) particularly preferred according to the present invention are those obtained by condensation reaction(s) by simultaneous / sequential / alternating esterification(s) of: at least one compound of formula (I), in which y = 0, and R1 is chosen from a hydrocarbyl group having 8 to 24 carbon atoms, preferably 10 to 24, more preferably 12 to 24 carbon atoms, at least one compound of formula (II), and at least one compound of formula (III), in which R7 is a hydrocarbyl group having 1 to 7, preferably 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, as well as their partial or total quaternary reaction products.

[0055] The preferred compounds of formula (1) according to the present invention are those obtained by condensation reaction(s) by simultaneous / sequential / alternating esterification(s) of: at least one compound of formula (I), in which y = 0, R1 is selected from a hydrocarbyl group having 8 to 24 carbon atoms, preferably 10 to 24, more preferably 12 to 24 carbon atoms, and AO is ethoxy; at least one compound of formula (II), and at least one compound of formula (III), in which R7 is a hydrocarbyl group having 1 to 7, preferably 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, and AO is ethoxy; as well as their partial or total quaternary reaction products.

[0056] Compounds of formula (1) particularly preferred according to the present invention are those obtained by condensation reaction(s) by simultaneous / sequential / alternating esterification of: at least one compound of formula (I), in which y = 0, R1 is selected from a hydrocarbyl group having 8 to 24 carbon atoms, preferably 10 to 24, more preferably 12 to 24 carbon atoms, AO is ethoxy, and m and n, each independently of each other, identical or different, represent an integer from 1 to 10, preferably 1 to 6, more preferably 1 to 4, inclusive; at least one compound of formula (II), selected from diacids (D represents -OH) and their corresponding anhydrides, in which R2 is a divalent hydrocarbyl radical having from 1 to 14, more preferably from 1 to 10, even more preferably from 1 to 8 carbon atoms, inclusive; and at least one compound of formula (III), in which R7 is a hydrocarbyl group having 1 to 7, preferably 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, A"O is ethoxy, and u and u' each represent 1, as well as their total quaternary reaction products with methyl chloride.

[0057] Typical preferred compounds of formula (1) according to the present invention are those obtained by condensation reaction(s) by simultaneous / sequential / alternating esterification(s) of: at least one compound of formula (I) selected from n-octylamine, n-decylamine, n-dodecylamine, (coco-alkyl)amine, (palm oil-alkyl)amine, n-tetradecylamine, n-hexadecylamine, n-octadecylamine, oleylamine, (tallow-alkyl)amine, (hydrogenated tallow-alkyl)amine, (rapeseed-alkyl)amine, (soybean-alkyl)amine, erucylamine, alkoxylated with 2 to 20, preferably 2 to 10 EO (ethylene oxide motifs), and / or 2 to 20, preferably 2 to 10 PO (propylene oxide motifs), at least one compound of formula (II) selected from malonic acid, succinic acid, glutaric acid, glutaconic acid, adipic acid, muconic acid, pimelic acid, phthalic acid and its isomers, tetrahydrophthalic acid, malic acid, maleic acid, fumaric acid, suberic acid, mesaconic acid, sebacic acid, azelaic acid, tartaric acid, itaconic acid, glutinic acid, citraconic acid, brassylic acid,dodecanedioic acid, traumatic acid, thapsic acid, their corresponding acid chlorides, their corresponding methyl or ethyl esters, and their corresponding cyclic anhydrides, as well as mixtures thereof, and at least one compound of formula (III) selected from methyldiethanolamine, ethyldiethanolamine, propyldiethanolamine, butyldiethanolamine, isobutyldiethanolamine, pentyldiethanolamine, hexyldiethanolamine, heptyldiethanolamine, as well as their corresponding alkoxylation products, , as well as their partial or total quaternary reaction products.

[0058] Preferred compounds of formula (1) according to the present invention are those obtained by simultaneous / sequential / alternating condensation reaction(s) by esterification of: at least one compound of formula (I) selected from n-dodecylamine, (coco-alkyl)amine, (palm oil-alkyl)amine, n-tetradecylamine, n-hexadecylamine, n-octadecylamine, oleylamine, (tallow-alkyl)amine, (hydrogenated tallow-alkyl)amine, (rapeseed-alkyl)amine, (soybean-alkyl)amine, erucylamine, alkoxylated with 2 to 20, preferably 2 to 10 EO (ethylene oxide motifs), at least one compound of formula (II) selected from malonic acid, succinic acid, glutaric acid, glutaconic acid, adipic acid, muconic acid, pimelic acid, phthalic acid and its isomers, tetrahydrophthalic acid, malic acid, maleic acid, fumaric acid, suberic acid, mesaconic acid, sebacic acid, azelaic acid, tartaric acid, itaconic acid, glutinic acid, citraconic acid, brassylic acid, dodecanedioic acid, traumatic acid, thapsic acid, and their corresponding acid chlorides,their corresponding methyl or ethyl esters, and their corresponding cyclic anhydrides, as well as mixtures thereof, and at least one compound of formula (III) selected from methyldiethanolamine, ethyldiethanolamine, propyldiethanolamine, butyldiethanolamine, isobutyldiethanolamine, pentyldiethanolamine, hexyldiethanolamine, heptyldiethanolamine, and their corresponding ethoxylation products, , as well as their partial or total quaternary reaction products.

[0059] The preferred compounds of formula (1) according to the present invention are those obtained by condensation reaction(s) by simultaneous / sequential / alternating esterification(s) of: at least one compound of formula (I) selected from n-dodecylamine, (coco-alkyl)amine, (palm oil-alkyl)amine, n-tetradecylamine, n-hexadecylamine, n-octadecylamine, oleylamine, (tallow-alkyl)amine, (hydrogenated tallow-alkyl)amine, (rapeseed-alkyl)amine, (soybean-alkyl)amine, erucylamine, alkoxylated with 2 to 20, preferably 2 to 10 EO (ethylene oxide motifs), at least one compound of formula (II) selected from malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, maleic acid, fumaric acid, suberic acid, sebacic acid, azelaic acid, brassylic acid, dodecanedioic acid, their corresponding cyclic anhydrides, and at least one compound of formula (III) selected from methyldiethanolamine, ethyldiethanolamine, propyldiethanolamine, butyldiethanolamine, isobutyldiethanolamine, pentyldiethanolamine, hexyldiethanolamine, heptyldiethanolamine, as well as their total quaternary reaction products with methyl chloride.

[0060] The compounds of formula (1) according to the invention offer numerous advantages, including their relatively easy preparation process, which can be implemented even on an industrial scale. Most compounds of formula (1) can be readily prepared from inexpensive and readily available starting materials.

[0061] The compound obtained by the esterification condensation of the alkoxylated fatty amine of formula (I) (comprising its partial or total quaternary product) with the dicarboxylic acid, or a derivative thereof, of formula (II), and with an (alkyl)alkanolamine derivative of formula (III) (comprising its partial or total quaternary product), and more particularly the compound of formula (1), as defined above and according to the present invention, possesses numerous interesting properties. As such, it can be used, by way of illustration only and without limitation, as a surfactant, biocide, corrosion inhibitor, wetting agent, and the like.

[0062] As such, the compound that can be obtained by the esterification condensation of the alkoxylated fatty amine of formula (I) (including its partial or total quaternary product) with the dicarboxylic acid, or a derivative thereof, of formula (II), and with an (alkyl)alkanolamine derivative of formula (III) (including its partial or total quaternary product), and more particularly the compound of formula (1) as defined above, can be used in various applications, among which uses may be mentioned as a collector for ore enrichment (flotation), as a corrosion inhibitor, for example in the field of oil and gas production, as a viscosifier, emulsifier or stabilizer useful for the oil and gas industry (such as a demulsifying agent, surfactant to improve oil recovery, surfactant for fracturing fluids,surfactant for acidifying fluids, surfactant to improve the injectivity of produced water, surfactant for drilling muds, and the like), as a clay modifier, as an adhesion promoter, as an anti-caking additive, for example in the field of oil and gas production, as an additive in hair care products, as a fabric softener, as an antistatic agent in polymers, as a bitumen emulsion additive, as a cationic detergent, for example in the field of industrial detergents, car washing, as an additive for fertilizers, as an anti-caking agent for hydrates, as a lubrication additive or adhesion promoter, and the like.

[0063] The invention will become clearer from the following examples, which are given by way of illustration only and are not intended to limit the scope of protection sought as defined by the appended claims. Throughout the description, examples, and claims, all value ranges are to be understood as "inclusive limits" (i.e., the limits are included within said ranges), unless otherwise specifically stated. Method for measuring acid value :

[0064] In all the following examples, the acid value is measured by potentiometric titration using a potassium hydroxide solution as the reagent and isopropyl alcohol as the solvent.

[0065] In a 250 mL beaker, approximately 10 g of the sample to be analyzed is precisely weighed (Sw, accuracy to the nearest mg), and 70 mL of isopropyl alcohol is added. The mixture is stirred and gently heated, if necessary, to obtain a homogeneous sample. The titrator's combined reference glass electrode is introduced into the solution, which is then stirred with a magnetic stirrer. The acid-base titration of the sample is performed using a 0.1 N aqueous potassium hydroxide (KOH) solution, and the pH change is recorded on the titrator. The equivalence point is determined graphically using methods known to those skilled in the art, and the volume (VKOH, in mL) of potassium hydroxide solution used to reach this point is determined. The acid value (AV) is then obtained according to the following calculation: AV= Normalité de la solution de KOH mol / L × 56,1 × V KOH Sw Method for measuring total alkalinity :

[0066] In all the following examples, the total alkalinity value is measured by potentiometric titration using hydrochloric acid solution as the reagent and isopropyl alcohol as the solvent.

[0067] In a 100 mL polypropylene beaker, approximately 3 g of the sample to be analyzed are precisely weighed (accuracy to the mg, Sw to the g) and 60 mL of isopropyl alcohol are added. The mixture is stirred and gently heated, if necessary, to obtain a homogeneous sample. Once the solution has cooled to room temperature, the combined reference glass electrode of the titrator is introduced into the solution, which is then stirred with a magnetic stirrer. The sample is titrated using a 0.2 N hydrochloric acid (HCl) solution of precisely known normality (N, in m³ eq. mL⁻¹). The pH change is recorded on the titrator. The equivalence point is determined using methods known to those skilled in the art, and the volume (VHCl, in mL) of hydrochloric acid solution used to reach this point is determined. The total alkalinity (Alk) value is then obtained using the following calculation: Alk meq / g = VHCL ∗ n Sw EXAMPLE 1: Synthesis of a product A (according to the invention)

[0068] In a 4 L round-bottom flask are introduced 1196.7 g (2.5 moles) of ethoxylated tallow amine (5OE) supplied by Arkema under the trade name Noramox ®< S5, 715.2 g (3.45 moles) of methyldiethanolamine (> 99%) supplied by Taminco and 0.5 g of an aqueous solution of hypophosphorous acid at 50% by weight.

[0069] The mixture is heated to 80 °C with nitrogen bubbling. The bubbling is stopped and 756.8 g (5.18 moles) of adipic acid are then introduced under stirring.

[0070] After 15 minutes, the temperature of the mixture is raised to 120 °C over a period of 1 hour, and the pressure in the vessel is gradually decreased until a pressure of 6.66 kPa (50 mm Hg) is reached. The temperature is then raised to 190 °C, and the temperature and pressure are maintained until virtually all the acid is consumed (acid number < 5).

[0071] The system is then cooled to recover 2482.3 g of crude orange / brown liquid reaction product containing the desired esteramine, with the amines and diacid having not reacted. EXAMPLE 2 : synthesis of product B (according to the invention)

[0072] In a 4 L round-bottom flask are introduced 1420.1 g (2.97 moles) of ethoxylated tallow amine (5OE) supplied by Arkema under the trade name Noramox ®< S5, 353.2 g (2.97 moles) of methyldiethanolamine (> 99%) supplied by Taminco and 0.5 g of an aqueous solution of hypophosphorous acid at 50% by weight.

[0073] The mixture is heated to 80 °C with nitrogen bubbling. The bubbling is stopped and 650 g (4.45 moles) of adipic acid are then introduced under stirring.

[0074] After 15 minutes, the mixture temperature is raised to 160 °C and maintained for 4 hours. The temperature is then raised to 190 °C, and the temperature and pressure are maintained until virtually all the acid is consumed (acid number < 5). The pressure in the vessel is then gradually reduced until a pressure of 6.66 kPa (50 mm Hg) is reached, and the temperature and pressure are maintained for a further 2 hours.

[0075] Finally, the system is cooled and the pressure is brought back to atmospheric pressure in order to recover 2260 g of crude orange / brown liquid reaction product containing the desired esteramine, with the amines and diacid having not reacted. EXAMPLE 3: Synthesis of a product C (according to the invention)

[0076] In a 6L glass reactor, 2022 g of the esteramine A product obtained in Example 1 are introduced with 453 g of isopropyl alcohol. Methyl chloride is added until the pressure in the vessel reaches 290 kPa. The temperature is maintained at 80–85 °C until the reaction is complete.

[0077] A complete reaction is achieved when the total alkalinity is less than or equal to 0.2 m eq.g⁻¹. The reactor is then allowed to cool to 65 °C and the pressure is reduced to atmospheric pressure. Nitrogen is bubbled through the mixture for 2 hours before 2095.9 g of the crude brown reaction product, still containing 6.7 wt% isopropyl alcohol, is collected. EXAMPLE 4: Synthesis of a product D (according to the invention)

[0078] In a 6L glass reactor, 1803.7 g of the esteramine B product obtained in Example 2 are introduced with 788.3 g of isopropyl alcohol. Methyl chloride is added until the pressure in the vessel reaches 290 kPa. The temperature is maintained at 80–85 °C until the reaction is complete.

[0079] A complete reaction is achieved when the total alkalinity is less than or equal to 0.2 m eq.g⁻¹. The reactor is then allowed to cool to 65 °C and the pressure is reduced to atmospheric pressure. Nitrogen is bubbled through the mixture for 2 hours before 2206.6 g of the crude brown reaction product, still containing 17.3 wt% isopropyl alcohol, is collected. EXAMPLE 5 : synthesis of a product E (according to the invention)

[0080] In a 4 L dry autoclave, 595 g (5 M) of MDEA (methyldiethanolamine) and 6 g of KOH (50 wt% aqueous solution) are added. The reactor is then sealed and filled with a nitrogen atmosphere, and the seal is protected against leaks. The MDEA and catalyst are dehydrated to less than 1000 ppm water. The pressure is then increased to 75 kPa and 25 °C with nitrogen. The temperature in the reactor is then raised to 90 °C with stirring. Next, the temperature is raised again to 120 °C, and 40 g to 50 g of ethylene oxide are added. Additional ethylene oxide, for a total of 1100 g (25 M), is added over 3 hours at 140 °C to 150 °C. After the addition of ethylene oxide, the reaction mixture is maintained at this temperature for 30 min ("baking"), then the liquid phase is subjected to nitrogen distillation. At the end of the reaction, the reactor is cooled to 60 °C and 1655 g of MDEA 5 EO are obtained.

[0081] In a 4 L round-bottom flask are introduced 1420.3 g (2.97 moles) of ethoxylated tallow amine (5OE) supplied by Arkema under the trade name Noramox ®< S5, 745.5 g (2.97 moles) of MDEA 5OE (synthesized as described above) and 0.5 g of an aqueous solution of hypophosphorous acid at 50 wt%.

[0082] The mixture is heated to 80 °C with nitrogen bubbling. The bubbling is stopped and 650 g (4.45 moles) of adipic acid are then introduced under stirring.

[0083] After 15 minutes, the mixture temperature is raised to 160 °C and maintained for 4 hours. The temperature is then raised to 190 °C, and the temperature and pressure are maintained until virtually all the acid is consumed (acid number < 5). The pressure in the vessel is then gradually reduced until a pressure of 6.66 kPa (50 mm Hg) is reached, and the temperature and pressure are maintained for a further 2 hours.

[0084] Finally, the system is cooled and the pressure is brought back to atmospheric pressure in order to recover 2654.5 g of crude orange / brown liquid reaction product containing the desired esteramine, with the amines and diacid having not reacted. EXAMPLE 6 : synthesis of a product F (according to the invention)

[0085] In a 6L glass reactor, 2050 g of the esteramine E product obtained in Example 5 are introduced with 615 g of isopropyl alcohol. Methyl chloride is added until the pressure in the vessel reaches 290 kPa. The temperature is maintained at 80–85 °C until the reaction is complete.

[0086] A complete reaction is achieved when the total alkalinity is less than or equal to 0.2 m eq.g⁻¹. The reactor is then allowed to cool to 65 °C and the pressure is reduced to atmospheric pressure. Nitrogen is bubbled through the mixture for 2 hours before 2496.9 g of the crude brown reaction product, still containing 12.4 wt% isopropyl alcohol, is collected. EXAMPLE 7 : synthesis of a product G (according to the invention)

[0087] In a 4 L dry autoclave, 510 g (5 M) of DMAPA (dimethylaminopropylamine) and 5 g (1 wt%) of water are added. The reactor is then sealed and filled with a nitrogen atmosphere, and the seal is protected against leaks. The pressure is then increased to 100 kPa and 30°C with nitrogen. The temperature in the reactor is then raised to 120°C with stirring. 40 g of ethylene oxide are added. The temperature is increased linearly until the reaction begins. Additional ethylene oxide, for a total of 1100 g (25 M), is added over 4 hours at 150–160°C. After the addition of the ethylene oxide, the reaction mixture is held at this temperature for 30 min ("baking"), and then the liquid phase is subjected to nitrogen distillation. At the end of the reaction, the reactor is cooled to 60 °C and 1570 g of DMAPA 5 EO are obtained.

[0088] In a 4 L round-bottom flask are introduced 1196.1 g (2.5 moles) of ethoxylated tallow-amine (5OE) supplied by Arkema under the trade name Noramox ®< S5, 805.4 g (2.5 moles) of DMAPA 5OE (synthesized as described above) and 0.5 g of an aqueous solution of hypophosphorous acid at 50 wt%.

[0089] The mixture is heated to 80 °C with nitrogen bubbling. The bubbling is stopped and 547.9 g (3.75 moles) of adipic acid are then introduced under stirring.

[0090] After 15 minutes, the mixture temperature is raised to 160 °C and maintained for 4 hours. The temperature is then raised to 190 °C, and the temperature and pressure are maintained until virtually all the acid is consumed (acid number < 5). The pressure in the vessel is then gradually reduced until a pressure of 6.66 kPa (50 mm Hg) is reached, and the temperature and pressure are maintained for a further 2 hours.

[0091] Finally, the system is cooled and the pressure is brought back to atmospheric pressure in order to recover 2413.9 g of crude orange / brown liquid reaction product containing the desired esteramine, with the amines and diacid having not reacted. EXAMPLE 8 : synthesis of a product H (according to the invention)

[0092] In a 6L glass reactor, 2040 g of the esteramine E product obtained in Example 5 are introduced with 600 g of isopropyl alcohol. Methyl chloride is added until the pressure in the vessel reaches 290 kPa. The temperature is maintained at 80–85 °C until the reaction is complete.

[0093] A complete reaction is achieved when the total alkalinity is less than or equal to 0.2 m eq.g⁻¹. The reactor is then allowed to cool to 65 °C and the pressure is reduced to atmospheric pressure. Nitrogen is bubbled through the mixture for 2 hours before 2396.7 g of the crude brown reaction product, still containing 12.9 wt% isopropyl alcohol, is collected. EXAMPLE 9: Synthesis of products I to R (according to the invention)

[0094] Following the same procedure as in Example 1, the following products were prepared from the compounds listed in Table 1 below: Table 1: compounds and quantities used to synthesize products I to R according to the invention Alkoxylated fatty amine of formula (I) Weight of (I) (in g) Dicarboxylic acid, or derivative, of formula (II) Weight of (II) (in g) Derivative of (alkyl)-alkanolamine with formula (III) Weight of (III) (in g) Product Product weight (in g) NoxS5 717,7 Ac. Ad. 657,5 MDEA 932,9 I 2145,6 NoxS5 956,9 Ac. Ad. 730,5 MDEA 829,2 J 2336,1 NoxS5 1435,4 Anh. succ. 450,5 MDEA 621,9 K 2345,4 NoxS5 1435,4 Anh. Malé. 441,5 MDEA 621,9 L 2336,2 NoxS5 1435,4 Ac.Séb. 909,9 MDEA 621,9 M 2804,5 NoxS2 1039,4 Ac. Ad. 657,5 MDEA 621,9 N 2156,3 NoxS11 1446,4 Ac. Ad. 438,3 MDEA 414,6 O 2190,8 NoxC5 1320,9 Ac. Ad. 657,5 MDEA 621,9 P 2437,7 NoxS5 1435,4 Ac. Ad. 657,5 TEA 447,6 Q 2378,1 NoxS11 1446,4 Ac. Ad. 438,3 MDEA5OE 502,0 R 2278,2 NoxS5 is an ethoxylated tallow amine (5OE) supplied by Arkema under the trade name Noramox®< S5. NoxS2 is an ethoxylated tallow amine (2OE) supplied by Arkema under the trade name Noramox®< S2. NoxS11 is an ethoxylated tallow amine (110E) supplied by Arkema under the trade name Noramox®< S11. NoxC5 is an ethoxylated coco-amine (5OE) supplied by Arkema under the trade name Noramox®< C5. MDEA is methyldiethanolamine (> 99%) supplied by Taminco. TEA is triethanolamine (> 99%) supplied by Taminco. MDEA is methyldiethanolamine (> 99%) supplied by Taminco. MDEA 5 OE is as described in Example 5. Ac. Ad. denotes adipic acid, Anh. Succ. denotes succinic anhydride, and Anh. Male. refers to maleic anhydride. EXAMPLE 10: Synthesis of products 5 to AB (according to the invention)

[0095] Following the same procedure as in Example 3, the quaternary chloromethyl ammonium derivatives of products I to R were prepared from the compounds shown in Table 2 below: Table 2 : compounds and quantities used to synthesize products S to AB according to the invention Reactive product Product weight (in g) Weight of isopropanol (in g) Product obtained Weight of product obtained (in g) Isopropanol content of the product (% by weight) I 1800,2 540,1 S 2187,7 14,8 % J 1900,5 570,2 T 2255,1 13,9 % K 1900,2 570,1 U 2286,4 14,2 % L 1900,1 570,0 V 2258,0 13,1 % M 2200,3 660,1 W 2556,7 11,6 % N 1800,4 540,1 X 2176,8 14,4 % 0 1800,1 540,0 Y 2111,6 12,8 % P 2000,1 600,0 Z 2350,2 12,3 % Q 2000,3 600,1 AA 2322,0 11,1 % R 1800,4 540,1 AB 2142,7 14,1 %

Claims

1. Compound which may be obtained by esterification condensation of: A / an alkoxylated fatty amine of formula (I), or the product of partial or total quaternization of said alkoxylated fatty amine of formula (I): in which: R1 is chosen from a hydrocarbyl group containing 8 to 24 carbon atoms, preferably 10 to 24 and more preferably 12 to 24 carbon atoms, and a group of formula R4-O-(A'O)w-T-, in which R4 is a hydrocarbyl group containing 8 to 24 carbon atoms and preferably 12 to 24 carbon atoms, w represents an integer in the range from 0 to 20, preferably from 0 to 10, more preferably from 0 to 6 and even more preferably from 0 to 4, A'O is an alkylenoxy group containing 2 to 4 carbon atoms, preferably 2 or 3 carbon atoms, more preferably 2 carbon atoms; T is alkylene with 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms and most preferably 2 or 3 carbon atoms, AO is an alkylenoxy group containing 2 to 4 carbon atoms, preferably 2 or 3 carbon atoms, more preferably 2 carbon atoms, B is chosen from a C1-C4 alkyl, an aryl and an arylalkyl (for example phenyl or phenylalkyl, such as benzyl) group, m represents an integer between 1 and 20, preferably between 1 and 10, more preferably between 1 and 6, and even more preferably between 1 and 4, limits inclusive, n represents an integer between 1 and 20, preferably between 1 and 10, more preferably between 1 and 6, and even more preferably between 1 and 4, limits inclusive, s is 1, 2 or 3, preferably 2 or 3, and y is an integer from 0 to 5, preferably from 0 to 3, more preferably y is 0 or 1, even more preferably y is 0, B / with a dicarboxylic acid, or a derivative thereof, of formula (II): in which D is chosen from -F, -Cl, Br and -OR3, in which R3 is hydrogen or a C1-C4 alkyl group, R2 is chosen from the group constituted by: a direct bond, a linear or branched, saturated or unsaturated C1-C20 hydrocarbon-based chain optionally substituted with one or more -OH groups, preferably an alkylene radical of formula -(CH2)z-, in which z is an integer from 1 to 20, preferably from 1 to 10, preferably from 2 to 6 and most preferably equal to 4, a substituted alkylene radical, said alkylene radical being substituted with 1 or 2-OH groups, an alkenylene radical containing from 1 to 20 and preferably from 1 to 10 carbon atoms, a substituted alkenylene radical, said alkenylene radical being substituted with 1 or 2 methyl and / or methylene groups, a cycloalkylene group, cycloalkenylene and arylene C / with an (alkyl)alkanolamine of formula (III) derivative or product of partial or total quaternization of said (alkyl)alkanolamine derivative of formula (III): in which: A"0 represents an alkylenoxy group containing from 2 to 4 carbon atoms, preferably 2 or 3 carbon atoms, more preferably 2 carbon atoms, u represents an integer between 1 and 20, preferably between 1 and 10, more preferably between 1 and 6, and even more preferably between 1 and 4, limits inclusive, u' represents an integer between 1 and 20, preferably between 1 and 10, more preferably between 1 and 6, and even more preferably between 1 and 4, limits inclusive, R7 is chosen from a hydrocarbyl group containing 1 to 7, preferably 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, an aryl or arylalkyl group (for example, a phenyl or naphthyl group), a group of formula H-(OA")v- (in which v represents an integer between 1 and 20, preferably between 1 and 10, more preferably between 1 and 6, and even more preferably between 1 and 4, limits inclusive), HO(CH2)q-, and a group of formula (IV): in which R8 and R9, which may be identical or different, are chosen from a hydrocarbyl group containing 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, and q is an integer from 1 to 10, preferably from 2 to 6, limits inclusive, and most preferably q is 2 or 3, or R8 and R9, together with the nitrogen atom to which they are attached, form a 5-, 6- or 7-membered ring, optionally including one or more heteroatoms chosen from oxygen, nitrogen and sulfur.

2. Compound according to Claim 1, in which the radical R1 of the fatty amine of formula (I) includes 8 or more than 8 carbon atoms, typically from 8 to 24 carbon atoms, preferably from 10 to 24, more preferably from 12 to 24 carbon atoms, limits inclusive, and the radical R7 of the (alkyl)alkanolamine derivative of formula (III) includes 6 carbon atoms or less, typically from 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, limits inclusive.

3. Compound according to Claim 1 or Claim 2, in which the radical R1 and the radical R7 of the fatty amine of formula (I) and of the (alkyl)alkanolamine derivative of formula (III), respectively, are such that the difference in the number of carbon atoms they include is greater than 2, typically from 2 to 23, preferably from 5 to 23, more preferably from 10 to 23, limits inclusive.

4. Compound according to any one of Claims 1 to 3, in which some or all of the nitrogen atoms also react with a reagent of formula R5X, in which R5 is chosen from a C1-C6 hydrocarbyl group, preferably a C1-C4 alkyl, a phenyl and a phenylalkyl, such as benzyl, group, and X is chosen from halogens, sulfates, carbonates, and the like.

5. Compound according to any one of Claims 1 to 4, in which the alkoxylated fatty amine of formula (I) is of formula (IA): which is the alkoxylated fatty amine of formula (I) in which y represents 0 and R1, AO, m and n are as defined in Claim 1, and also the corresponding partially or totally quaternized derivatives thereof.

6. Compound according to any one of Claims 1 to 5, in which the (alkyl)alkanolamine derivative of formula (III) is of formula (IIIA): which is the (alkyl)alkanolamine of formula (III) in which u and u' each represent 1, A"O is ethylenoxy and R7 is as defined in Claim 1, and is preferably a hydrocarbyl group containing 1 to 4 carbon atoms, and also the corresponding partially or totally quaternized derivatives thereof.

7. Compound according to any one of Claims 1 to 6, in which the (alkyl)alkanolamine derivatives of formula (III) comprise, but are not limited to, triethanolamine, methyldiethanolamine, ethyldiethanolamine, propyldiethanolamine, butyldiethanolamine, isobutyldiethanolamine, pentyldiethanolamine, phenyldiethanolamine, hexyldiethanolamine, heptyldiethanolamine, and also the corresponding alkoxylation products thereof.

8. Compound according to any one of Claims 1 to 7, in which the dicarboxylic acid derivative of general formula (II) is chosen from a dicarboxylic acid, a dicarboxylic acid halide, a dicarboxylic acid diester or a cyclic anhydride of a dicarboxylic acid.

9. Compound according to any one of Claims 1 to 8, in which illustrative examples of dicarboxylic acid derivatives of general formula (II) comprise oxalic acid, malonic acid, succinic acid, glutaric acid, glutaconic acid, adipic acid, muconic acid, pimelic acid, phthalic acid and isomers thereof, tetrahydrophthalic acid, malic acid, maleic acid, fumaric acid, suberic acid, mesaconic acid, sebacic acid, azelaic acid, tartaric acid, itaconic acid, glutinic acid, citraconic acid, brassylic acid, dodecanedioic acid, traumatic acid, thapsic acid, the corresponding acid chlorides thereof, the corresponding methyl or ethyl esters thereof, and the corresponding cyclic anhydrides thereof, and also mixtures thereof.

10. Compound according to any one of Claims 1 to 9, in which the mole ratio between the reagents [(I) + (III)] and (II) is from 2:1 to 1:2, preferably from 1.5:1 to 1:1.5 and most preferably from 1.4:1 to 1:1.4.

11. Compound according to any one of Claims 1 to 9, in which the mole ratio between the reagents [(I) + (III)] and (II) is from 2:1 to 1:1, preferably from 2:1 to 1.2:1 and most preferably from 2:1 to 1.3:1.

12. Compound according to any one of Claims 1 to 11, in which the mole ratio between (I) and (III) is from 15:1 to 1:15, preferably from 10:1 to 1:10, more preferably from 4:1 to 1:4 and most preferably from 2:1 to 1:2.

13. Compound of general formula (1): in which: R2 is chosen from the group constituted by: a direct bond, a linear or branched, saturated or unsaturated C1-C20 hydrocarbon-based chain optionally substituted with one or more -OH groups, preferably an alkylene radical of formula -(CH2)z-, in which z is an integer from 1 to 20, preferably from 1 to 10, preferably from 2 to 6 and most preferably equal to 4, a substituted alkylene radical, said alkylene radical being substituted with 1 or 2 - OH groups, an alkenylene radical containing from 1 to 20 and preferably from 1 to 10 carbon atoms, a substituted alkenylene radical, said alkenylene radical being substituted with 1 or 2 methyl and / or methylene groups, a cycloalkylene group, cycloalkenylene and arylene R5 is chosen from a C1-C6 hydrocarbyl group, preferably a C1-C4 alkyl group, a phenyl group and a phenylalkyl group, such as benzyl, X is chosen from halogens, sulfates, carbonates, and the like, t is 0 or 1, p is an integer in the range from 1 to 15, preferably from 1 to 10, more preferably from 1 to 5, limits inclusive, QO represents an alkylenoxy group containing from 2 to 4 carbon atoms, preferably 2 or 3 carbon atoms, more preferably 2 carbon atoms, given that all the Q groups present in the compound of formula (1) may be identical or different, q1, q2, q3 and q4, which may be identical to or different from each other, each represent an integer between 1 and 20, preferably between 1 and 10, more preferably between 1 and 6 and even more preferably between 1 and 4, limits inclusive, each group R10, independently of each other, represents R7 or a group R7-(G)y-, R7 is chosen from a hydrocarbyl group containing 1 to 7, preferably 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, an aryl or arylalkyl group (for example, a phenyl or naphthyl group), a group of formula H-(OA")v- (in which v represents an integer between 1 and 20, preferably between 1 and 10, more preferably between 1 and 6, and even more preferably between 1 and 4, limits inclusive), HO(CH2)q-, and a group of formula (IV): in which R8 and R9, which may be identical or different, are chosen from a hydrocarbyl group containing 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, and q is an integer from 1 to 10, preferably from 2 to 6, limits inclusive, and most preferably q is 2 or 3, or R8 and R9, together with the nitrogen atom to which they are attached, form a 5-, 6- or 7-membered ring, optionally including one or more heteroatoms chosen from oxygen, nitrogen and sulfur, R1 is chosen from a hydrocarbyl group containing 8 to 24 carbon atoms, preferably 10 to 24 and more preferably 12 to 24 carbon atoms, and a group of formula R4-O-(A'O)w-T-, in which R4 is a hydrocarbyl group containing 8 to 24 carbon atoms and preferably 12 to 24 carbon atoms, w represents an integer in the range from 0 to 20, preferably from 0 to 10, more preferably from 0 to 6 and even more preferably from 0 to 4, A'O is an alkylenoxy group containing 2 to 4 carbon atoms, preferably 2 or 3 carbon atoms, more preferably 2 carbon atoms; T is alkylene with 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms and most preferably 2 or 3 carbon atoms, y is an integer from 0 to 5, preferably from 0 to 3, more preferably y is 0 or 1, even more preferably y is 0, and G represents a group of formula (IV): in which R5, X and t are as defined above, B is chosen from a C1-C4 alkyl, an aryl and an arylalkyl (for example phenyl or phenylalkyl, such as benzyl) group, and s is 1, 2 or 3, preferably 2 or 3, given that at least one of the groups R10 represents R7, and at least one other of the groups R10 represents R1-(G)y- and each t is independent of the others.

14. Compound according to Claim 13, in which: R2 is chosen from the group consisting of a divalent hydrocarbyl radical containing from 1 to 10, preferably from 2 to 6 and most preferably 4 carbon atoms, limits inclusive, when R10 is R7, R7 is chosen from a hydrocarbyl group containing 1 to 4 carbon atoms, preferably 1 to 2 carbon atoms and most preferably R7 is methyl, when R10 is R1-(G)y-, y = 0 and R1 is chosen from a hydrocarbyl group containing 8 to 24 carbon atoms, preferably 12 to 24 carbon atoms, QO represents an ethoxy group and p, q1, q2, q3, q4, t, R5 and X are as defined in Claim 13.

15. Compound according to Claim 13 or Claim 14, in which all the "t" are equal to 1.

16. Compound according to any one of Claims 13 to 15, which is obtained from simultaneous / sequential / alternating esterification condensation reaction(s) of: at least one compound of formula (I), in which y = 0 and R1 is chosen from a hydrocarbyl group containing 8 to 24 carbon atoms, preferably 10 to 24 and more preferably 12 to 24 carbon atoms, at least one compound of formula (II), and at least one compound of formula (III), in which R7 is a hydrocarbyl group containing 1 to 7 and preferably 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, and also the products of partial or total quaternization reaction thereof.

17. Use of a compound according to any one of Claims 1 to 16 as a collector for ore enrichment (flotation), as a corrosion inhibitor, as a viscosity enhancer, emulsifier or stabilizer that is useful for the oil and gas industry, as a clay modifier, as an adhesion promoter, as an antiagglomerant additive, as an additive in haircare products, as a fabric softener, as an antistatic agent in polymers, as a bitumen emulsion additive, as a detergency cationic agent, as a fertilizer additive, as an antiagglomerant for hydrates, as a lubrication or adhesion-promoting additive, and the like.