Continuous or semi-continuous process for producing pre-activated organogel slurries

Abstract

The present invention relates to a continuous or semi-continuous process for preparing a pre-activated organogel slurry wherein the process comprises: (1) mixing at least one amide compound with at least one liquid carrier to provide a mixture wherein the mixing is carried out at a temperature T1 lower than the activation temperature of the amide compound; the present invention relates to a method for producing an amide compound, comprising (1) preparing a mixture of amide compounds, (2) continuously flowing the mixture through a heat exchanger to raise its temperature to a temperature T2 at least equal to the activation temperature of the amide compound, thereby obtaining a slurry, (3) filling the slurry into a container maintained at or above the activation temperature, and (4) retrieving and cooling the container.

Description

Technical Field

[0001] The present invention relates to a continuous or semi-continuous process for producing a preactivated organogelator slurry, the process comprising:

[0002] (1) mixing at least one amide compound with at least one liquid carrier to provide a mixture, wherein the mixing is performed at a temperature T1, wherein the temperature T1 is lower than the activation temperature of the amide compound;

[0003] (2) allowing the mixture to flow continuously through a heat exchanger to raise its temperature to a temperature T2 that is at least equal to the activation temperature of the mixture to obtain a slurry;

[0004] (3) filling the slurry into a container maintained at or above the activation temperature; and

[0005] (4) Retrieve and cool the container. Background Art

[0006] A variety of rheological additives have been used to increase the viscosity of mastic, glue or adhesive compositions, coating compositions (such as paints, varnishes, gel coats or inks), or molding compositions or even electrolyte compositions. Among them, polyamide powders, powders of hydrogenated castor oil-based derivatives, fumed silica, precipitated calcium carbonate or ground calcium carbonate can be mentioned. Fumed silica and calcium carbonate are inorganic in nature and require the mixture to be dispersed at very high speeds. However, these inorganic fillers exhibit problems with sedimentation and stability over time, which have a negative effect on the mechanical properties of the final system. Another particular disadvantage of polyamide powders and hydrogenated castor oil derivative powders is that the system needs to be activated during the production of the final composition by the user (formulator). This activation requires high-speed shearing, as well as heating corresponding to a temperature increase of up to about 120° C. according to the product, and also requires the necessary minimum time according to the temperature conditions and the system to develop the best final rheological properties.

[0007] The Applicant has proposed rheological additives that do not require an activation phase by the end user, since they are present in the form of a pre-activated slurry that can simply be blended into the final recipe (formulation) to provide it with thixotropic properties.

[0008] Thus, EP 1935934 proposes a rheological additive comprising at least one fatty acid diamide introduced in powder form and at least one organic plasticizer.

[0009] An improvement has been proposed in which the diamide comprises the reaction product of 12-hydroxystearic acid (HSA) and a linear aliphatic diamine and the plasticizer is replaced by a reactive (meth)acrylic-based solvent comprising at least one cycloaliphatic group (EP 3371253).

[0010] Subsequently, it was suggested to replace 12-HSA from castor oil with 14-hydroxyeicosanoic acid (14-HEA) from Lesquerella seeds (US 2015 / 0274644).

[0011] All of the abovementioned additives impart to the composition into which they are incorporated a thixotropic behavior characterized by pronounced shear thinning, ie a decrease in viscosity when the shear increases, followed by a recovery of the viscosity over time (equivalent to the hysteresis effect).

[0012] They provide excellent properties to the final composition, characterized by high viscosity at rest, good stability of this viscosity on storage, good resistance to settling, ease of application and extrusion, and good resistance to sagging after application. In addition, these rheological additives have been shown to be directly usable in a variety of solvent-based (solvent-based) or solvent-free formulations. However, they have always been prepared by a batch process comprising a first step of mixing the diamide with a plasticizer or a reactive or non-reactive solvent in an open container at a temperature below room temperature to obtain a homogeneous mixture, followed by a second step of closing the container and heating the mixture in an oven at an activation temperature (i.e., 35-120° C.) for 1-100 hours.

[0013] The activation step is sometimes difficult to control and reproduce, which can result in a slurry that is not always easy to disperse in the final formulation and whose rheological properties can vary depending on the container used to prepare it. In addition, the batch process is expensive in terms of time and energy, and the start-up and shutdown of production are tedious, which has a negative impact on its economic viability. Moreover, considering that the reaction container needs to be placed in an oven afterwards, only small amounts of diamide and plasticizer or solvent can be prepared. Further, the process limits the use of solvents to those with low vapor pressure, which is necessary to prevent the internal pressure of the container from increasing during heating or decreasing excessively during cooling.

[0014] Because of these safety issues, the process would not be applicable to reactive solvents such as methyl methacrylate unless expensive containers capable of withstanding such pressures were used.

[0015] It would therefore be desirable to provide a cost-effective and safe process for activating such rheological additives which is more reproducible and versatile and which can be used on an industrial scale even when using solvents with low vapor pressures. Summary of the invention

[0016] The inventors have demonstrated that pre-activated slurries of organogelators based on amide compounds can be prepared in a reproducible manner and on a large scale using a continuous or semi-continuous process including an activation step performed in a continuous flow mode.

[0017] Therefore, the present invention relates to a process for producing a preactivated organogelator slurry, wherein the process comprises:

[0018] (1) mixing at least one amide compound with at least one liquid carrier to provide a mixture, wherein the mixing is performed at a temperature T1 that is lower than the activation temperature of the amide compound,

[0019] (2) continuously flowing the mixture through a heat exchanger to raise its temperature to a temperature T2 at least equal to the activation temperature of the amide compound to obtain a slurry,

[0020] (3) filling the slurry into a container maintained at or above the activation temperature, and

[0021] (4) Retrieve and cool the container. DETAILED DESCRIPTION

[0022] The present invention relates to a process for producing a preactivated organogelator slurry.

[0023] An organogelator (also called a rheological additive or a thixotropic agent) may correspond to an organic molecule of low molecular weight (i.e., less than 2000 g / mol) that is capable of forming a thermoreversible organogel in an organic liquid, in particular at relatively low concentrations (i.e., less than 1% by weight based on the weight of the organic liquid). An organogelator may modify the rheology of a formulation into which it is introduced. In particular, an organogelator may impart a pseudoplastic or thixotropic effect to the formulation. Thus, an organogelator may increase the viscosity of the formulation when the formulation is at rest (no shear stress applied), and may reduce the viscosity of the formulation when the formulation is subjected to shear stress. The increase and decrease in viscosity may be determined relative to a control formulation that does not contain any organogelator.

[0024] In order to exhibit pseudoplastic or thixotropic properties, the organogelator must be activated. This activation generally involves applying specific heating conditions under shear for a certain period of time. This activation step is generally performed by the end user, i.e., a formulator who wishes to impart thixotropic or pseudoplastic properties to a formulation by adding an organogelator. For example, the end user may activate the organogelator before introducing it into the formulation, or the end user may activate the organogelator in situ (directly in the formulation).

[0025] Advantageously, the process of the present invention provides a pre-activated form of the organogelator slurry. The wording "pre-activated" should be understood to mean that the organogelator has thixotropic or pseudoplastic properties and is therefore ready for direct use by the end user. Thus, the pre-activated organogelator can be simply mixed into the formulation and will not require further activation to exhibit pseudoplastic or thixotropic properties.

[0026] The preactivated organogel obtained by the process of the present invention is in the form of a slurry. The wording "slurry" should be understood as follows: the preactivated organogel is dispersed in a liquid carrier, preferably, the preactivated organogel is in the form of an organogel. An organogel can be defined as a non-crystalline, non-glassy, ​​thermally reversible solid or semi-solid (jelly-like) material consisting of an organic liquid that is trapped in a three-dimensional cross-linked network that is self-assembled based on a structural agent (in this case an amide compound) through non-covalent interactions (such as hydrogen bonds, van der Waals forces, π-π stacking ion pairing, solvophobic effects and / or ion coordination). These interactions lead to the formation of a three-dimensional network of microfibrils that fix the organic liquid. The organogel is stable for several months at 25°C, i.e., there is no bulk phase separation. Under heating and stirring, the 3D network can be reversibly decomposed, the viscosity of the organogel can be reduced, and when the heating under stirring is stopped, the 3D network of microfibrils can be reformed.

[0027] The preactivated organogelator slurry obtained by the process of the present invention comprises at least one amide compound and at least one liquid carrier.

[0028] The amide compound can be selected from monoamides and / or diamides. Monoamides are compounds with one amide bond (-NH-C(=O)-). Such compounds can be the reaction product of at least one monoamine and at least one monocarboxylic acid. Diamides are compounds with two amide bonds (-NH-C(=O)-). Such compounds can be the reaction product of at least one diamine and at least one monocarboxylic acid. Asymmetric diamides can be obtained by reacting a mixture of diamines with monocarboxylic acids. When the reaction involves a mixture of diamines and / or a mixture of monocarboxylic acids, a mixture of diamides can be obtained.

[0029] Suitable amide compounds can be obtained by polycondensation between:

[0030] a) at least one selected from aliphatic C2 to C 24 Monoamines and / or diamines, cycloaliphatic C6 to C 18 Monoamine and / or diamine, aromatic C6 to C 18 Amines of monoamines and / or diamines and combinations thereof;

[0031] b) at least one hydroxylated C3 to C 36 Monocarboxylic acid;

[0032] c) optionally, at least one saturated linear non-hydroxylated C2 to C 18 Monocarboxylic acid.

[0033] The amide compound may be optionally combined with hydrogenated castor oil. In this case, the content of the amide compound may be in the range of 10 to 99 wt %, preferably 20 to 99 wt %, relative to the total weight of the amide compound and hydrogenated castor oil.

[0034] Component (a) includes at least one amine selected from monoamines, diamines and mixtures thereof. As used herein, a monoamine is a compound with a single secondary amine group (-NH2), and a diamine is a compound with two secondary amine groups. When component (a) comprises a monoamine, the reaction product comprises a monoamide. When component (a) comprises a diamine, the reaction product comprises a diamide. When component (a) comprises a monoamine and a diamine, the reaction product comprises a monoamide and a diamide. When component (a) comprises a mixture of diamines, the reaction product comprises a mixture of diamides.

[0035] Component (a) comprises at least one selected from aliphatic C2 to C 24 Monoamines and / or diamines, cycloaliphatic C6 to C 18 Monoamine and / or diamine, aromatic C6 to C 18 Amines of monoamines and / or diamines and combinations thereof.

[0036] As used herein, aliphatic C2 to C 24 The monoamines, respectively diamines, are non-cyclic monoamines, respectively diamines, containing 2 to 24 carbon atoms. The aliphatic monoamines and / or diamines may be linear or branched, preferably linear. The aliphatic monoamines and / or diamines preferably contain 2 to 12 carbon atoms, more preferably 2 to 8 carbon atoms, even more preferably 2 to 6 carbon atoms.

[0037] Examples of the aliphatic diamine include 1,2-ethylenediamine, 1,3-propylenediamine, 1,4-tetramethylenediamine, 1,5-pentamethylenediamine, 1,6-hexamethylenediamine, 1,8-octamethylenediamine, 1,12-dodecamethylenediamine, and combinations thereof; preferably 1,2-ethylenediamine or 1,6-hexamethylenediamine; more preferably 1,6-hexamethylenediamine.

[0038] As examples of suitable linear aliphatic monoamines for component (a), mention may be made of ethylamine, propylamine, butylamine, pentylamine, hexylamine, ethanolamine and combinations thereof, preferably ethylamine, propylamine, hexylamine or ethanolamine.

[0039] As used herein, a cycloaliphatic C6 to C 18The monoamines, respectively diamines are monoamines, respectively diamines, which contain 6 to 18 carbon atoms and at least one nonaromatic ring. The cycloaliphatic monoamines and / or diamines preferably contain at least one 6-membered nonaromatic ring, which may be bridged or fused to further nonaromatic rings.

[0040] As examples of cycloaliphatic diamines suitable for use as component (a), there may be mentioned C6 to C 12 Cycloaliphatic amines, and in particular: cyclohexane-1,3-, -1,4- or -1,2-, and in particular -1,3- or -1,4-diamine; 2- or 4-methylcyclohexane-1,3-diamine; isophoronediamine; 1,2-, 1,3- or 1,4-bis(aminomethyl)cyclohexane (derived from the hydrogenation of m-, p- or o-xylenediamine, respectively), preferably 1,3- or 1,4-bis(aminomethyl)1,4-cyclohexane; decahydronaphthalenediamine; bis(3-methyl-4-aminocyclohexyl)methane (BMACM); bis(4-aminocyclohexyl)methane (BACM); 1-{[4-(aminomethyl)cyclohexyl]oxy}propan-2-amine; and combinations thereof. Preferred cycloaliphatic diamines are selected from: cyclohexane-1,3- or -1,4-diamine, 1,2-, 1,3- or 1,4-bis(aminomethyl)cyclohexane, isophoronediamine or bis(4-aminocyclohexyl)methane.

[0041] As examples of cycloaliphatic monoamines suitable as component (a), mention may be made of cyclohexylamine, isophoramine, and combinations thereof.

[0042] As used herein, aromatic C6 to C 18 The monoamines, respectively diamines, are monoamines, respectively diamines, which contain 6 to 18 carbon atoms and at least one aromatic ring. The aromatic monoamines and / or diamines preferably contain at least one 6-membered aromatic ring, which may be bridged or fused to another aromatic ring.

[0043] As suitable and preferred examples of aromatic diamines as component (a), there may be mentioned C6 to C 14 Aromatic amines, and especially: m- or p-xylylenediamine, m- or p-phenylenediamine, m- or p-toluenediamine, 3,4'- or 4,4'-diaminodiphenyl ether, 4,4'-diaminodiphenylmethane and combinations thereof.

[0044] As aromatic monoamines, benzylamine, xylidine and toluidine may be mentioned.

[0045] Preferably, component (a) comprises at least one C2 to C 24 , especially C2 to C 12 , more particularly C2 to C8 linear aliphatic diamines; and optionally at least one selected from cycloaliphatic C6 to C 18 Diamine, aromatic C6 to C 18 Other diamines of diamines and combinations thereof.

[0046] Component (b) comprises at least one hydroxylated C3 to C 36 Monocarboxylic acids are compounds containing 3 to 36 carbon atoms, a single carboxyl group (-COOH) and one or more hydroxyl groups (-OH), preferably a single hydroxyl group. 36 The monocarboxylic acids may be saturated or unsaturated, in which case the trans form is preferred, preferably saturated.

[0047] The hydroxylated monocarboxylic acid is preferably selected from C 16 To C 22 Monohydroxylated monocarboxylic acids, preferably 14-hydroxyeicosanoic acid and / or 9-, 10- and / or 12-hydroxystearic acid (9-HSA, 10-HSA and / or 12-HSA). 12-Hydroxystearic acid can be obtained by hydrogenating castor oil and then hydrolyzing the resulting hydrogenated castor oil. 14-Hydroxyeicosanoic acid can be derived from Lesquerella oil produced by extraction from Lesquerella seeds, and thus from the cultivation of Lesquerella. Lesquerella oil is typically transesterified with methanol, the resulting product is then hydrogenated and finally hydrolyzed to provide 14-hydroxyeicosanoic acid. An example of a polyhydroxylated monocarboxylic acid is 9,10-dihydroxystearic acid.

[0048] Preferably, component (b) comprises 12-hydroxystearic acid.

[0049] Component (c) is optional and comprises at least one saturated linear non-hydroxylated C2 to C 18 A monocarboxylic acid, i.e. a linear saturated compound, contains 2 to 18 carbon atoms, a single carboxyl group (-COOH) and no hydroxyl group (-OH). The non-hydroxylated monocarboxylic acid preferably contains 2 to 15 carbon atoms, more preferably 6 to 12 carbon atoms. As examples of non-hydroxylated monocarboxylic acids suitable for component (c), mention may be made of: acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, heptanoic acid, caprylic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid and stearic acid. The following non-hydroxylated monocarboxylic acids are preferred: caproic acid, caprylic acid, nonanoic acid and decanoic acid.

[0050] According to one embodiment of the present invention, the amide compound is a diamide compound obtained by polycondensation between 12-hydroxystearic acid and 1,6-hexamethylenediamine.

[0051] The polycondensation reaction between the above components (a) and (b) and optionally (c) can be carried out at a temperature in the range of 140 to 250° C., preferably 150 to 200° C. The reaction is preferably carried out under an inert atmosphere. The molar ratio between the amine groups of component (a) and the carboxyl groups of components (b) and (c) is typically in the range of 0.9 to 1.1 and preferably 1:1. In addition, if component (c) is present, the molar ratio of component (b) to component (c) is generally in the range of 1:2 to 4:1.

[0052] This polycondensation reaction allows the recovery of the amide compound. By this expression, it is intended to specify one or more monoamide compounds, one or more diamide compounds and mixtures thereof. Preferred amide compounds are diamide compounds optionally mixed with monoamide compounds.

[0053] The amide compound obtained after the polycondensation reaction is typically in solid form. In order to facilitate the mixing of the amide compound with the liquid carrier in the first step of the process of the present invention, the amide compound is preferably in the form of a granular material. In particular, the amide compound may be in powder form or in a micronized form. For example, the amide compound may be micronized by mechanical grinding (ball milling) or air flow milling. Preferably, the amide compound has a volume particle size Dv(90) of less than 30 μm, preferably less than 25 μm, more preferably less than 20 μm, and even more preferably less than 15 μm. In particular, Dv(90) may be between greater than 5 μm and less than 30 μm. The Dv(90) particle size may be understood as a volume-based size distribution comprising 90% of the particles present in a given sample. The size may be determined by laser diffraction using the method described herein.

[0054] Then, the amide compound can be converted into a pre-activated organogelator slurry using the process according to the present invention. In particular, the amide compound can be mixed with a liquid carrier and heated to a temperature equal to or higher than its activation temperature to allow its molecules to self-assemble through non-covalent bonds, thereby obtaining microfibrils.

[0055] The first step of the process of the present invention involves the use of a liquid carrier. The liquid carrier can be used to at least partially solubilize or disperse the amide compound.

[0056] The liquid carrier may be any organic compound that is liquid at temperature T1 (e.g., 30° C.). Preferably, the liquid carrier is an organic compound that is always liquid in the temperature range of 0° C. to T1 (e.g., 0 to 30° C.). Preferably, the liquid carrier is an organic compound that is always liquid in the temperature range of T1 to T2 (e.g., 30° C. to 120° C.).

[0057] The liquid carrier may comprise one or more plasticizers, one or more reactive solvents and one or more non-reactive solvents, or mixtures thereof.In the present specification, the wording "plasticizer" or "solvent" therefore encompasses both individual compounds and mixtures of compounds, unless otherwise stated.

[0058] As used herein, the term "solvent" means a compound that is capable of at least partially solubilizing an amide compound, optionally under heating conditions. The solvent is preferably an aprotic organic solvent. Even more preferably, the solvent is a polar aprotic organic solvent.

[0059] As used herein, the term "reactive solvent" means a solvent comprising a reactive functional group, i.e., a functional group capable of reacting with at least one component of the formulation added to the preactivated organogelator slurry. For example, the reactive solvent may comprise at least one polymerizable carbon-carbon double bond and / or at least one epoxy ring.

[0060] As used herein, the term "non-reactive solvent" means a solvent that is inert to the components of the formulation added to the preactivated organogelator slurry. Typically, the non-reactive solvent does not contain reactive functional groups as defined above.

[0061] As used herein, the term "plasticizer" means a compound capable of modifying the mechanical and / or thermal properties of a formulation added to a preactivated organogelator slurry, optionally under heating conditions. For example, a plasticizer may have one or more of the following effects on a formulation added to a preactivated organogelator slurry: reducing viscosity, reducing glass transition temperature, increasing flexibility, etc.

[0062] Examples of non-reactive solvents are: xylene; alcohols such as methanol, ethanol, butanol and benzyl alcohol; cyclic saturated hydrocarbons such as cyclopentane, cyclohexane, methylcyclohexane, ethylcyclohexane, dimethylcyclohexane, trimethylcyclohexane and decalin; alkyl esters of monocarboxylic acids such as methyl formate, methyl acetate, ethyl acetate, butyl acetate, hexyl acetate, heptyl acetate, methyl propionate, ethyl propionate, pentyl propionate and ethyl ethoxypropionate; alkyl esters of dicarboxylic acids such as methyl glutarate, methyl succinate and methyl adipate; lactones such as γ-butyrolactone; ethers such as dimethoxyethane (DME), methyl ethers of oligoethylene glycols of 2 to 5 oxyethylene units, 1,3-dioxolane, dioxane, dibutyl ether and tetrahydrofuran; ketones such as cyclohexanone; Phosphates or sulfites; Nitriles such as acetonitrile, pyruvonitrile, propionitrile, methoxypropionitrile, dimethylaminopropionitrile, butyronitrile, isobutyronitrile, valeronitrile, pivalonitrile, isovaleronitrile, glutaronitrile, methoxyglutaronitrile, 2-methylglutaronitrile, 3-methylglutaronitrile, adiponitrile and malononitrile; Carbonates such as ethylene carbonate, propylene carbonate, butylene carbonate, dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate, diphenyl carbonate, methylphenyl carbonate, dipropyl carbonate, methylpropyl carbonate, ethylpropyl carbonate, vinylene carbonate, fluoroethylene carbonate, trifluoropropylene carbonate; and mixtures thereof.

[0063] Examples of mixtures of non-reactive solvents are mixtures of xylene with ethanol or butanol, for example in a mass ratio of 1:1 to 4:1.

[0064] In the case where a reactive solvent is used, it is typically selected from an ethylenically unsaturated compound (i.e., a compound containing a polymerizable carbon-carbon double bond) or an epoxide (i.e., a compound containing an epoxy ring). A polymerizable carbon-carbon double bond is a carbon-carbon double bond that can react with another carbon-carbon double bond in a polymerization reaction. The polymerizable carbon-carbon double bond is generally selected from acrylates (including cyanoacrylates), methacrylates, acrylamides, methacrylamides, maleates, fumarates, itaconates, allyls, propenyls, vinyls, and combinations thereof, preferably selected from acrylates, methacrylates, and vinyls, more preferably selected from acrylates and methacrylates.

[0065] In particular, the reactive solvent may contain one or more ethylenically unsaturated compounds selected from (meth)acrylic monomers, styrenic monomers, vinyl monomers, olefinic monomers, unsaturated polyacids or derivatives thereof, and mixtures thereof.

[0066] As used herein, the term "(meth)acrylic monomer" refers to a monomer containing a carbon-carbon double bond conjugated to a carbonyl (-C(=O)-) bond. Such a monomer typically comprises a (meth)acryloyl group. Preferably, the (meth)acrylic monomer is a monofunctional (meth)acrylic monomer, i.e., it comprises only one (meth)acryloyl group. The term "(meth)acryloyl" refers to an acryloyl group (-C(=O)-CH=CH2) or a methacryloyl group (-C(=O)-C(CH3)=CH2). The (meth)acrylic monomer may be selected from alkyl (meth)acrylates (particularly methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, tert-butyl (meth)acrylate or 2-ethylhexyl (meth)acrylate); cycloaliphatic (meth)acrylates (particularly dicyclopentadienyl (meth)acrylate, norbornenyl (meth)acrylate, isobornyl (meth)acrylate (IBO (M)A), tert-butyl cyclohexanol (meth)acrylate (TBCH (M)A), tricyclodecane methanol mono (meth)acrylate and 3,3,5-trimethylcyclohexanol (meth)acrylate (TMCH (M)A)); hydroxyalkyl (meth)acrylates (particularly 2-hydroxyethyl (meth)acrylate); (meth)acrylic acid; (meth)acrylamide; (meth)acrylonitrile; or mixtures thereof.

[0067] As used herein, the term "styrene monomer" refers to a monomer containing a carbon-carbon double bond at the alpha position of the aromatic ring. The styrene monomer may be selected from styrene, α-methylstyrene, tert-butylstyrene, o-, m- or p-methylstyrene, o-, m- or p-ethylstyrene, o-methyl-p-isopropylstyrene, p-chlorostyrene, p-bromostyrene, o-, p-dichlorostyrene, o-, p-dibromostyrene, o-, m- or p-methoxystyrene, optionally substituted indene, optionally substituted vinylnaphthalene, acenaphthylene, stilbene, vinylanthracene or a mixture thereof.

[0068] As used herein, the term "vinyl monomer" refers to a monomer containing a vinyl group (-CH=CH2) which is not conjugated with a carbonyl (C=O) group or an aromatic group. Vinyl monomers differ from olefin monomers in that they contain at least one heteroatom (i.e., an atom other than carbon or hydrogen). The vinyl monomer may be selected from vinyl halides (particularly vinyl chloride); vinyl esters (particularly vinyl acetate, vinyl formate, vinyl propionate, vinyl butyrate, vinyl isobutyrate, vinyl pivalate, vinyl valerate, vinyl hexanoate, vinyl octanoate, vinyl 2-ethylhexanoate, vinyl nonanoate, vinyl laurate, vinyl stearate, and vinyl versatate, i.e., esters of branched monocarboxylic acids having 6, 9, 10, or 11 carbon atoms, available from Hexion under reference number EH, 9. 10 or 11); vinyl ether (especially methyl-, ethyl-, butyl- or isobutyl vinyl ether) or a mixture thereof.

[0069] As used herein, the term "olefin monomer" refers to a non-aromatic hydrocarbon monomer containing one or more carbon-carbon double bonds. The olefin monomer can be selected from ethylene, propylene, 1-butene, isobutylene, diisobutylene, 1-nonene, 1-decene, butadiene or a mixture thereof.

[0070] As used herein, the term "unsaturated polyacid" refers to a compound comprising at least one carbon-carbon double bond and at least two carboxyl groups, wherein the carbon-carbon double bond is conjugated with at least one of the carboxyl groups. The term "unsaturated polyacid derivative" refers to a compound capable of, for example, generating an unsaturated polyacid in situ by hydrolysis or ring opening. Examples of applicable unsaturated polyacid derivatives include alkyl esters and cyclic anhydrides of unsaturated polyacids. Unsaturated polyacids or derivatives thereof may be selected from fumaric acid, maleic acid, itaconic acid, aconitic acid, mesaconic acid, anhydrides thereof, and mixtures thereof.

[0071] Alternatively, the reactive diluent may be a cardanol derivative or a glycidyl ether.

[0072] As used herein, the term "cardaol derivative" refers to a compound obtained by chemically modifying cardaol. Cardaol is a bio-based phenolic lipid extracted from cashew nut shell liquid (a byproduct of cashew processing). Cardaol comprises a phenolic ring substituted with an unsaturated fatty chain and can be chemically modified by a variety of reactions. The OH group of the phenolic ring can be converted into an ester group, a phosphate group, an ether or a glycidyl ether. Alternatively, the unsaturated fatty chain can be epoxidized. Examples of applicable cardaol derivatives include -{3-[(8E)-pentadeca-8-ene-1-yl]phenoxymethyl}oxirane (Cardolite NC-513) or [(7Z)-pentadeca-7-ene-1-yl]phenol (Cardolite NX-2022).

[0073] As used herein, the term "glycidyl ether" refers to a A compound having a glycidyl ether group.

[0074] Glycidyl ethers can be obtained by reacting alcohols or polyols with epichlorhydrin. Examples of suitable glycidyl ethers include C4-C 20Alkyl glycidyl ethers (e.g., octyl, decyl, dodecyl, tetradecyl or hexadecyl glycidyl ether), 1,2- or 1,3-propylene glycol diglycidyl ether, 1,2-, 1,3- or 1,4-butanediol diglycidyl ether, 1,5-pentanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, 1,8-octanediol diglycidyl ether, 1,9-nonanediol diglycidyl ether, 1,10-decanediol diglycidyl ether Water glyceryl ether, 1,12-dodecanediol diglycidyl ether, 2-methyl-1,3-propanediol diglycidyl ether, neopentyl glycol diglycidyl ether, 2,2-diethyl-1,3-propanediol diglycidyl ether, 3-methyl-1,5-pentanediol diglycidyl ether, 3,3-dimethyl-1,5-pentanediol diglycidyl ether, 2,4-diethyl-1,5-pentanediol diglycidyl ether, 3,3-butylethyl-1 ,5-pentanediol diglycidyl ether, glycerol triglycidyl ether, trimethylolmethane triglycidyl ether, trimethylolethane triglycidyl ether, trimethylolpropane triglycidyl ether, di(trimethylolpropane) tetraglycidyl ether, pentaerythritol tetraglycidyl ether, cyclohexane diglycidyl ether, cyclohexane-1,4-dimethanol diglycidyl ether, tricyclodecane dimethanol diglycidyl ether, isosorbide diglycidyl ether, catechol diglycidyl ethers, resorcinol diglycidyl ether, cardol glycidyl ether, phloroglucinol triglycidyl ether, pyrogallol triglycidyl ether, tris(hydroxyphenyl)methane triglycidyl ether, tris(hydroxyphenyl)ethane triglycidyl ether, hydrogenated bisphenol diglycidyl ether, bisphenol diglycidyl ether, glycidyloxypropyl trimethoxysilane, and mixtures thereof.

[0075] According to one embodiment, the reactive solvent is a monofunctional (meth) acrylic monomer, preferably an alkyl (meth) acrylate or a cycloaliphatic (meth) acrylate. The preactivated organogelator syrup obtained from these monomers is particularly suitable as an additive for compositions based on epoxyamine two-component reaction systems, wherein the reactive solvent is capable of reacting with the amine (curing agent) of the epoxyamine system.

[0076] In case a plasticizer is used, the plasticizer is preferably selected from polar organic plasticizers, which generally contain at least one polar group selected from ether groups and / or ester groups and / or epoxy groups.

[0077] The plasticizer comprising at least one ether group may be chosen from polyethers, such as homopolymers and / or copolymers of ethylene oxide and / or propylene oxide, and / or blends of said polyethers (homopolymers and / or copolymers) and / or derivatives thereof, these derivatives including, in particular, said polyethers blocked at the chain ends by C1 (methoxy) to C4 (butoxy) alkoxy or C2 (acetate) to C4 (butyrate) ester groups, said polyethers having a weight average molecular weight Mw ranging from 150 to 6000 and preferably from 1000 to 3000. The expression "copolymer" is understood to include both random copolymers and block copolymers.

[0078] The plasticizer containing at least one ester group may be selected from C4 to C 21 Monoesters and / or polyesters (multifunctional esters) obtained from an alcohol and a unit or polyacid having a functionality ranging from 1 to 4, the alcohol being optionally alkoxylated, for example having 1 to 10 alkoxy units selected from oxyethylene units (OE) and / or oxypropylene (OP) units, the acid being selected from: (a) an organic acid selected from a C6 to C 10 Aromatic acids with a chain length of C4 to C 18 Fatty acids with a range of chain lengths (excluding the –CO2H functional group) and / or fatty acids with C6 to C 10 (a) cycloaliphatic acids of a wide range of chain lengths (excluding the -CO2H functional group); and (b) inorganic acids.

[0079] Esters of aromatic acids may be selected from phthalic acid esters (phthalates) and trimellitic acid esters (trimellitic esters). Esters of fatty acids may be selected from adipic acid esters (adipates), citric acid esters (citric acid esters), sebacic acid esters (sebacates) and azelaic acid esters (azelacates). Esters of cycloaliphatic acids may be selected from tetrahydrophthalic acid esters (tetrahydrophthalates) and hexahydrophthalic acid esters (hexahydrophthalates). Esters of inorganic acids may be selected from sulfonic acid esters (sulfonates), especially C 10 To C 21 Alkyl sulfonates, sulfuric acid esters (sulfates), sulfite esters (sulfites), phosphoric acid esters (phosphates), phosphonic acid esters (phosphonates) and phosphinic acid esters (phosphinates).

[0080] Finally, in case the plasticizer comprises at least one epoxy group, it may be chosen from epoxidized vegetable oils such as epoxidized soybean oil or epoxidized linseed oil and epoxidized fatty acid alkyl esters such as epoxidized methyl oleate, epoxidized isopentyl stearate or epoxidized 2-ethylhexyl stearate.

[0081] Among the preferred plasticizers, mention may be made of a compound comprising at least one C6 to C 10Those containing aromatic ester groups, in particular plasticizers selected from monoalkyl and / or dialkyl phthalates, and even more preferably selected from dialkyl phthalates or hexahydrophthalates, wherein the alkyl groups are identical or different and are selected from C7 to C 18 Alkyl, and preferably C 10 To C 12 The most preferred plasticizers in this class (dialkyl (hexahydro) phthalates) are diisoundecyl phthalate and diisononyl hexahydrophthalate. The most preferred polyethers are homopolymers of propylene oxide (polypropylene glycol) with a weight average molecular weight Mw ranging from 1000 to 3000, and more particularly polypropylene glycol (PPG) with a Mw equal to 2000, and / or derivatives thereof, chosen from monoesters, preferably C2 to C4 monoesters, or C1 to C4 monoethers, such as monomethoxylated or monoethoxylated polypropylene glycol.

[0082] Typically, the amide compound is present in a weight ratio relative to the liquid carrier ranging from 5:1 to 1:20, preferably from 2:1 to 1:15, more preferably from 1:1 to 1:10, and even more preferably from 1:3 to 1:6.

[0083] More specifically, the process of the present invention includes a first step (also referred to as a mixing step) of mixing an amide compound with a liquid carrier to provide a mixture. This step can be carried out in a tank or reactor equipped with a stirring system such as a rotating impeller and optionally one or more baffles. For example, the amide compound and the liquid carrier can be stirred at 1000-3000rpm, preferably at 1500-2000rpm. The stirring can be carried out for 10 minutes to 1 hour, for example, 15 to 30 minutes. Alternatively, the mixing step can be carried out in a static mixer, for example, in a pipe or tube equipped with a static element, which redistributes the fluid in the lateral direction of the mainstream direction (i.e., radial and tangential directions). For example, the amide compound can be introduced into a continuous flow of a liquid carrier flowing through a static mixer. The mixing step is carried out at a temperature T1, which is lower than the activation temperature of the amide compound. Preferably, the temperature T1 should be at least 10°C, or at least 20°C, or at least 30°C lower than the activation temperature of the amide compound. It is advantageous to select such a temperature so that the viscosity of the mixture does not increase significantly in the mixing step (which will not lead to premature activation of the amide compound). In one embodiment, T1 is at most 30°C, preferably at most 25°C, even more preferably 0 to 25°C. In the mixing step, the temperature of the mixture can be adjusted to be kept below T1 by any appropriate method such as a cold bath or a double-jacket cooling system. The temperature regulation can be used to avoid overheating caused by shearing during the mixing of the amide compound and / or to avoid premature and uncontrolled activation of the amide compound. The mixing step can be performed until a uniform mixture is obtained. The uniformity of the mixture can be characterized by the following: for a volume of no more than 1 liter prepared on a laboratory scale, when the amide compound is mixed with a liquid carrier at a shear rate preferably between 2 and 6 m / s-1, there is no sedimentation or visible particles.

[0084] In the second step of the process according to the invention, the above mixture flows continuously through a heat exchanger to raise its temperature to a temperature T2 (also referred to as an activation step). Thus, the temperature of the mixture when entering the heat exchanger may be at most T1, which is lower than the activation temperature of the amide compound (e.g., 0 to 30°C), and the temperature of the mixture when leaving the heat exchanger is T2 (e.g., 35 to 120°C). The temperature T2 is at least equal to the activation temperature of the amide compound, i.e., a temperature sufficient to form an organic gel. The activation temperature can be easily determined by a person skilled in the art according to the properties of the amide compound and the liquid carrier used. For example, a person skilled in the art can apply heat to a mixture of amide and a liquid carrier in a container and observe when the gel point is reached. The temperature T2 is typically in the range of 35 to 120°C, for example, 50 to 100°C. During its stay in the heat exchanger, the temperature of the mixture is gradually increased by the heat exchange fluid circulating in the heat exchanger. The temperature of the heat exchange fluid when entering the heat exchanger may be equal to the temperature T2. The heat exchange fluid may circulate in co-current or countercurrent relative to the flow of the mixture. When the mixture leaves the heat exchanger, it is in the form of a slurry. The residence time of the mixture in the heat exchanger depends inter alia on the flow rate of the mixture, the target activation temperature, the flow of the heat exchange fluid and the size of the heat exchanger. Typically, the residence time may be less than 1 hour, preferably 30 seconds to 50 minutes, and more preferably 1 minute to 30 minutes. The activation step may be carried out in any suitable heat exchanger that allows a continuous flow of the mixture and allows the residence time of the mixture to be adjusted. For example, the heat exchanger may be selected from a double pipe heat exchanger, a coil heat exchanger, a shell and tube heat exchanger or a plate heat exchanger. The flow rate of the mixture may be adjusted to a set value according to the size of the heat exchanger so that the residence time is within a predetermined optimal range.

[0085] The continuous flow of the mixture through the heat exchanger can be driven by a pump. The pump can be placed upstream of the heat exchanger. The type of pump used is not critical, so that, for example, non-clogging pumps, impeller-type pumps, disc flow pumps, rotary piston pumps, eccentric single-rotor screw pumps, cylindrical diaphragm pumps, etc. can be used. It is also not of critical importance whether the mixture is pumped in laminar or turbulent flow.

[0086] The slurry material thus obtained after the second step is filled into a container maintained at a temperature equal to or higher than the activation temperature (such as temperature T2). Then, the container is retrieved and cooled before being used for formulation. Thus, the process of the present invention allows the preparation of pre-activated organogelator slurry by a continuous process. In an embodiment of the present invention, a semi-continuous process can be used in the case where the slurry is not fully activated when leaving the heat exchanger. Therefore, the process may further include the step of transferring the container to an oven to complete the activation of the amide compound; typically carried out at a previously set temperature (temperature T2) and for a predetermined period of time, and then retrieved and cooled.

[0087] In any case, activation is considered complete when the gel point is reached, i.e. when the consistency of the slurry reaches a plateau value and does not subsequently vary significantly. The thus activated gel (also called preactivated organogelator slurry) can be characterized first by a rather simple test, i.e. by inserting a wooden spatula into the gel or slurry to be tested, the spatula remaining vertical and motionless if the product being tested is sufficiently activated, the gel or slurry remains a single phase and does not ooze out the liquid carrier. More specifically, the viscosity of the activated slurry is such that the maximum penetration value of the slurry formed is less than 15 mm, preferably less than 10 mm, measured according to ASTM standard D 217 (2010) under the following conditions: temperature 23° C., cone 30 degrees, test speed 5 mm / s, and penetration force 0.4 N. Alternatively, it can be considered that the appropriate viscosity has been reached when the dynamic elastic modulus E' of the slurry is at least 104 Pa at 23° C. and 1 Hz.

[0088] An example of an apparatus that can be used to perform the process of the present invention is shown in the accompanying drawings.

[0089] As shown in the figure, the apparatus includes a reaction vessel 1 equipped with a stirring device 2, such as a stainless steel or copper tank equipped with a rotating impeller. On a laboratory scale, a round bottom container equipped with a PTFE stirrer can be used. The reaction vessel is fluidly connected to a container (not shown) containing an amide compound and a liquid carrier, respectively, and is supplied to the reaction vessel 1 by a pump (not shown). The reaction vessel is immersed in a cold bath to keep the temperature inside the reaction vessel at a temperature T1 in the range of 0 to 5°C. The uniform mixture prepared in the reaction vessel 1 is transferred to a heat exchanger 4, such as a coil heat exchanger, by a pump 3 (e.g., a peristaltic pump), and the heat exchanger 4 is connected to a hot bath 5 maintained at 60-65°C. The heat exchanger is installed so that the mixture flows through the coil, and the hot water flows around the coil in a closed loop. The mixture is kept flowing continuously in the heat exchanger until it reaches a temperature T2 at least equal to the activation temperature, in this case 60-65°C. The residence time of the mixture in the heat exchanger 4 is controlled by adjusting the flow rate of the mixture by pump 3. Thus, an activated slurry is produced, which leaves the heat exchanger 4 through a conduit 6 and is divided into containers 8, such as sample vials, three of which are shown in the figure. These containers are kept at a temperature T2, i.e. 60-65° C., by a heat bath 7 and are collected after they have been filled. Optionally, an oven 9 is provided to keep the containers at a temperature T2 to complete the activation if necessary.

[0090] The preactivated organogel slurry as described above can be added to a formulation, which can be a coating composition, a molding composition or an electrolyte composition. The coating composition can be applied to various substrates and used as a protective coating and / or a decorative coating and / or a surface treatment coating. The coating composition can be selected from paints, varnishes, colored or colorless gel coatings, inks, PVC-based plastisols. Alternatively, it can be a cement, glue, adhesive or sealant composition. In another embodiment, the coating composition can be a cosmetic composition such as nail polish. In yet another embodiment, the coating composition can be a photocurable composition for stereolithography or 3D printing objects (particularly by inkjet). The coating composition can be applied to the substrate by spraying, for example using a spray gun, or using a brush or roller. In the case where the formulation is a molding composition, it can be selected from a molding composition of a composite, such as a molding composition of a SMC or BMC or a laminated composite, such as a hull or a composite plate. Examples of electrolyte compositions for lithium-ion batteries have been described in FR 3 103637. They may contain lithium salts and electrolytic additives such as fluoroethylene carbonate (FEC) or vinylidene carbonate.

[0091] The preactivated organogelator slurry may be present in these formulations at a weight content ranging from 1% to 30%, and preferably from 2% to 25%, and the amide compound may be present as a dry active substance at a weight content ranging from 0.2% to 8%, and preferably from 1% to 6%, relative to the weight of the formulation.

[0092] The formulation may contain further components such as, for example, fillers, plasticizers, wetting agents or pigments.

[0093] Typically, the formulation includes an organic reactive binder. The above preactivated organogelator slurry can be used with an organic reactive binder that crosslinks by a free radical route (whether under radiation, by heat or by an initiation system based on peroxides or hydrogen peroxide), and can also be used with an organic reactive binder that crosslinks by reaction with a reactive amino component by Michael addition reaction (e.g. epoxyamine two-component reactive adhesive).

[0094] Thus, according to one embodiment, the organic reactive binder is crosslinkable, either by heat or by irradiation under radiation such as UV radiation (in the presence of at least one photoinitiator) and / or EB radiation (electron beam, without initiator), including self-crosslinkable at room temperature, or is non-crosslinkable. The organic reactive binder may be one-component crosslinkable (only one reactive component) or two-component crosslinkable (based on two components that react with each other by mixing during use).

[0095] The organic reactive binder can be selected from at least one epoxy / amine (crosslinkable two-component) reaction system, unsaturated polyesters, vinyl esters, epoxidized resins, reactive silicone resins, alkyd resins grafted with polyesters or polyamides or of the diurea / diurethane type, or ungrafted alkyd resins, polyurethanes or silicones, crosslinkable two-component polyurethanes, poly(poly)siloxanes, polysulfide polymers, reactive acrylic polymers, (meth)acrylate multifunctional oligomers or acrylic oligomers or allyl multifunctional oligomers, butyl rubber, polychloropene or SBR type elastomers, or silanized prepolymers, preferably silanized polyethers or silanized polyurethanes, or silanized polyether / polyurethanes with -OH or CO2H functional groups.

[0096] In a more particular case, the organic reactive binder can be selected from the following crosslinkable two-component reaction systems: epoxy / amine or epoxy / polyamide systems, comprising at least one epoxy resin containing at least two epoxy groups and at least one amino or polyamide compound containing at least two amino groups; polyurethane systems, comprising at least one polyisocyanate and at least one polyol; polyol / melamine systems; and polyester systems based on at least one epoxy or one polyol reacted with at least one corresponding acid or anhydride.

[0097] According to other specific circumstances, the organic reactive binder can be a crosslinkable two-component polyurethane system or a crosslinkable two-component polyester system, which starts from an epoxy / carboxylic acid or anhydride reaction system, or starts from a polyol / carboxylic acid or anhydride system, or a polyol / melamine reaction system, wherein the polyol is a hydroxylated acrylic resin, or a polyester or polyether polyol.

[0098] According to one embodiment, the formulation is a coating composition selected from mastics, glues, adhesives or sealant compositions, which is self-crosslinkable and based on polyether / silane or polyurethane / silane organoreactive binders.

[0099] Typically, the formulation is prepared by adding the above-mentioned preactivated organogelator slurry to the remaining ingredients of the formulation, and then homogenizing the mixture using a kneader and / or a planetary mixer and / or a high-speed disperser, without applying a heat activation treatment in this step, wherein "high speed" refers to a tangential speed in the range of 2 to 15 m / s-1. BRIEF DESCRIPTION OF THE DRAWINGS

[0100] Figure 1 Apparatus useful for carrying out the continuous or semi-continuous process of the present invention is shown.

[0101] Example

[0102] In order to better understand the present invention, the following examples are provided for illustrative purposes only and are not intended to limit the scope of the present invention, which is determined by the appended claims.

[0103] Embodiment 1:

[0104] product:

[0105]

[0106] Synthesis Example 1: Preparation of diamide compound

[0107] 49.96 grams of HMDA (i.e. 0.43 moles, 0.86 amine equivalents) and 271.1 grams of 12-HSA (i.e. 0.86 moles, 0.86 acid equivalents) were placed in a nitrogen atmosphere in a 1-liter round-bottom flask equipped with a thermometer, a Dean-Stark apparatus, a condenser and a stirrer. The mixture was heated to 200°C under a nitrogen stream. Water was collected in a Dean-Stark apparatus at 150°C. The reaction was monitored by acid number and amine number. When the acid number and amine number were less than 10 mg KOH / g, the reaction mixture was cooled to 150°C and then discharged into a silicone-treated mold. After cooling to room temperature, the product was mechanically micronized by grinding and sieving to obtain a fine and controlled particle size with a volume particle size Dv90 below 10 μm. The particle size can be measured by dry laser particle size analyzer using Mastersizer MS3000 (Malvern Panalytical) under the following conditions:

[0108] Measuring range: 0.1 to 3500 μm

[0109] Optical model: 1.30-0i

[0110] Analysis mode: MS3000: Standard / fine powder peak

[0111] Shading: 0.3% to 10%

[0112] Number of measurements: 3 times

[0113] Laboratory Equipment:

[0114] -Comparative ratio

[0115] The following equipment is used to reproduce the process disclosed in

[0122] -

[0123] of US2015 / 0274644:

[0116]

[0117] According to the embodiment of the present invention

[0118] like Figure 1The apparatus shown and described in relation thereto is used to replicate the process according to the invention, wherein the reactor is a 500 mL round bottom vessel and the sample vials are 100 mL conical flasks.

[0119] Example 1 (comparative)

[0120] 70 grams of diamide compounds prepared in Synthesis Example 1 and 280 grams of solvent mixture (xylene: ethanol, 3: 1) are placed in a 500 mL metal pan and carried out at room temperature (20 ° C). Using an ATPDispermill disperser equipped with a 3 cm diameter paddle, the product is mixed at a speed of 1500 rpm (or rpm) for 30 minutes at a temperature not exceeding 20 ° C by adjusting the temperature through a cold water circulation. Activation is carried out by carefully closing the pan and placing it in an oven preheated to 60 ° C for 24 hours. After cooling and standing for 4 hours, the slurry is hard enough to keep the metal scraper in a vertical position.

[0121] Example 2 (according to the present invention)

[0122] 40 g of the diamide compound prepared in Synthesis Example 1 and 160 g of a solvent mixture (xylene:ethanol, 3:1) were placed in a round-bottom container.

[0123] The flask was then placed at 5°C with mechanical stirring for 30 minutes.

[0124] The mixture was then pumped to a coil distillation condenser preheated to 60 °C using a peristaltic pump.

[0125] At the other end of the pipe, the slurry is collected into a sample vial that is also preheated to 60°C. Once the sample vial is filled, the sample vial is removed from the hot bath. Optionally, in a semi-continuous process, the sample vial can then be placed in an oven preheated to 60°C for 1 hour. After cooling and standing for 4 hours, the slurry is hard enough to hold the metal scraper in a vertical position.

Claims

1. A process for producing a preactivated organogelator slurry, wherein the process comprises: (1) mixing at least one amide compound with at least one liquid carrier to provide a mixture, wherein the mixing is performed at a temperature T1 that is lower than the activation temperature of the amide compound, (2) continuously flowing the mixture through a heat exchanger to raise its temperature to a temperature T2 at least equal to the activation temperature of the amide compound, thereby obtaining a slurry, (3) filling the slurry into a container maintained at or above the activation temperature, and (4) Retrieve and cool the container.

2. The process according to claim 1, characterized in that The temperature T1 is at most 30°C, preferably at most 25°C, even more preferably from 0 to 25°C.

3. The process according to claim 1 or 2, characterized in that Step (1) is carried out under stirring at 1000-3000 rpm, preferably 1500-2000 rpm.

4. The process according to claim 3, characterized in that Stirring is performed for 10 minutes to 1 hour, for example 15 to 30 minutes.

5. The process according to any one of claims 1 to 4, characterized in that The temperature T2 is in the range of 35 to 120°C, for example, 50 to 100°C.

6. The process according to any one of claims 1 to 5, characterized in that The residence time of the mixture in the heat exchanger of step (2) is less than 1 hour, preferably 30 seconds to 50 minutes, and more preferably 1 minute to 30 minutes.

7. The process according to any one of claims 1 to 6, characterized in that Between steps (3) and (4), it further comprises the following step: transferring the container to an oven to complete activation of the amide compound.

8. The process according to any one of claims 1 to 7, characterized in that The amide compound is obtained by polycondensation between: a) at least one amine selected from aliphatic C2 to C 24 Monoamines and / or diamines, cycloaliphatic C6 to C 18 Monoamine and / or diamine, aromatic C6 to C 18 Monoamines and / or diamines, and combinations thereof, b) at least one hydroxylated C3 to C 36 Monocarboxylic acid, c) optionally, at least one saturated linear non-hydroxylated C2 to C 18 Monocarboxylic acid.

9. The process according to any one of claims 1 to 8, characterized in that The component (a) comprises at least one C2 to C 24 , especially C2 to C 12 , more particularly C2 to C8 linear aliphatic diamines; and optionally at least one selected from cycloaliphatic C6 to C 18 Diamine, aromatic C6 to C 18 Other diamines of diamines and combinations thereof.

10. The process according to any one of claims 1 to 9, characterized in that Component (b) includes at least one C 16 To C 22 Monohydroxylated monocarboxylic acids, preferably 14-hydroxyeicosanoic acid and / or 9-, 10- and / or 12-hydroxystearic acid (9-HSA, 10-HSA and / or 12-HSA).

11. The process according to any one of claims 1 to 10, characterized in that The amide compound is a diamide compound obtained by polycondensation of 12-hydroxystearic acid and 1,6-hexamethylenediamine.

12. The process according to any one of claims 1 to 11, characterized in that The liquid carrier includes one or more plasticizers, one or more reactive solvents, one or more non-reactive solvents, or mixtures thereof.

13. The process according to any one of claims 1 to 11, characterized in that The liquid carrier comprises a plasticizer, in particular a plasticizer selected from polar organic plasticizers bearing at least one ether group, ester group and / or epoxy group.

14. The process according to any one of claims 1 to 13, characterized in that The liquid carrier includes a reactive solvent, in particular a reactive solvent selected from (meth)acrylic monomers, styrene monomers, vinyl monomers, olefin monomers, unsaturated polyacids or derivatives thereof, and mixtures thereof.

15. The process according to any one of claims 1 to 14, characterized in that Liquid carriers include non-reactive solvents, particularly non-reactive solvents selected from the group consisting of xylene; alcohols such as methanol, ethanol, butanol and benzyl alcohol; cyclic saturated hydrocarbons such as cyclopentane, cyclohexane, methylcyclohexane, ethylcyclohexane, dimethylcyclohexane, trimethylcyclohexane and decalin; alkyl esters of monocarboxylic acids such as ethyl acetate, butyl acetate, hexyl acetate and heptyl acetate, ethyl propionate, pentyl propionate and ethyl ethoxypropionate; alkyl esters of dicarboxylic acids such as methyl glutarate, methyl succinate and methyl adipate; and mixtures thereof.

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