Composition of a crosslinkable organic binder comprising at least one diamide

Abstract

The invention relates to the use of a particular diamide in the manufacture of a composition comprising at least one crosslinkable organic binder. It also relates to a composition comprising at least one crosslinkable organic binder and at least one diamide as defined above, as well as its uses, particularly in the manufacture of a coating, chosen in particular from paints, varnishes, inks, and gelled finishing coatings; a glue or adhesive; a sealant; a sealant; a chemical sealant; a molded object; an object obtained by 3D printing; preferably a coating.

Description

Title of the invention: Crosslinkable organic binder composition comprising at least one diamide technical field

[0001] The invention relates to the use of a particular diamide in the manufacture of a composition comprising at least one crosslinkable organic binder. It also relates to a composition comprising at least one crosslinkable organic binder and at least one diamide as defined above, as well as its uses, particularly in the manufacture of a coating, chosen in particular from among paints, varnishes, inks, and gel coats; a glue or adhesive; a sealant; a sealant; a chemical sealant; a molded object; an object obtained by 3D printing; preferably a coating.

[0002] A number of rheological additives have been used to increase the viscosity of sealant, glue or adhesive compositions, coating compositions, or molding compositions. These include polyamide powders, powders of hydrogenated castor oil derivatives, fumed silica, precipitated calcium carbonates, and ground calcium carbonates. Inorganic fillers require very high-speed dispersion of the mixture and present stability and sedimentation problems over time, resulting in negative effects on the mechanical properties of the final system. Polyamide powders and powders of hydrogenated castor oil derivatives, on the other hand, require system activation by the user (formulator) during the preparation of the final composition.This activation includes high-speed shearing and heating corresponding to temperature increases of up to approximately 120°C depending on the product, for a minimum duration depending on the temperature conditions and the system, in order to develop optimal final rheological properties.

[0003] The Applicant has already proposed rheology additives that confer thixotropic properties to a formulation after an activation phase.

[0004] Thus, a rheology additive or organogestor in the form of a diamide, which is in powder form and is activated in an organic solvent that may be a reactive diluent or a plasticizer, has been proposed in particular in WO 2015 / 011375. This diamide is the reaction product of a cycloaliphatic diamine, an acyclic diamine, optionally an aromatic diamine, a hydroxylated fatty acid, and optionally a non-hydroxylated monocarboxylic acid.

[0005] Although these solutions have proven satisfactory in most applications While some applications are being considered, it remains necessary for certain applications, particularly in the formulation of coatings such as paints, to increase the run resistance of coatings obtained from these systems. Furthermore, it would be desirable to improve the thixotropic properties of these formulations.

[0006] In this context, it appeared to the Applicant that the use of diamides obtained from a cycloaliphatic diamine and a mixture of hydroxylated and non-hydroxylated monocarboxylic acids made it possible to prepare diamides satisfying these needs. Summary of the invention

[0007] The present invention thus relates to the use of a diamide in the manufacture of a composition comprising at least one crosslinkable organic binder, characterized in that said diamide is obtained from a reaction mixture comprising:

[0008] a) at least one cycloaliphatic diamine at C6 to C[8,

[0009] b) at least one monocarboxylic acid hydroxylated at C3 to C36,

[0010] c) at least one non-hydroxylated monocarboxylic acid at C2 to C12,

[0011] the reaction mixture being devoid of acyclic diamine in C2 to C[2.

[0012] The invention also relates to a composition comprising at least one crosslinkable organic binder and at least one diamide as defined above.

[0013] It also relates to the use of this composition in the manufacture of a coating, chosen in particular from among gelled paints, varnishes, inks and finishing coatings (“gel coats”); a glue or adhesive; a sealant; a sealing agent; a chemical sealant; a molded object; an object obtained by 3D printing; preferably a coating.

[0014] The diamide used according to the invention gives the composition containing it excellent properties characterized by high viscosity at rest, good stability of this viscosity during storage, good resistance to sedimentation, ease of application and extrusion, and good resistance to sagging after application. Furthermore, this rheological additive can be used in a variety of solvent-based or solvent-free formulations, including those with high pigment and / or filler content. DETAILED DESCRIPTION

[0015] The invention relates to a diamide intended to be used in or for the manufacture of a composition comprising at least one crosslinkable organic binder.

[0016] This diamide is obtained from a reaction mixture comprising:

[0017] a) at least one cycloaliphatic diamine at C6 to C18,

[0018] b) at least one monocarboxylic acid hydroxylated at C3 to C36,

[0019] c) at least one non-hydroxylated monocarboxylic acid at C2 to C12,

[0020] the reaction mixture being devoid of acyclic diamine in C2 to Ci2.

[0021] In the context of this description, the term “diamide” includes a mixture of symmetric and / or asymmetric diamides resulting from the reaction of one or more diamines with one or more carboxylic acids.

[0022] Component a) present in the reaction mixture comprises at least one C6 to C18 cycloaliphatic diamine. "C6 to C18 cycloaliphatic diamine" means a compound comprising 6 to 18 carbon atoms, two primary amine groups (-NH2), and at least one non-aromatic ring. The cycloaliphatic diamine preferably comprises at least one 6-membered non-aromatic ring, which may be bonded, bridged, or fused to another non-aromatic ring.

[0023] Examples of cycloaliphatic diamines suitable as component a) include C6 to C[2] cycloaliphatic diamines and in particular: cyclohexane-1,2-, -1,3- or -1,4-diamine; 2- or 4-methylcyclohexane-1,3-diamine; Isophoronediamine; 1,2-, 1,3-, or 1,4-bis(aminomethyl)cyclohexane; decahydronaphthalenediamine; bis(3-methyl-4-aminocyclohexyl)methane (BMACM); bis(4-aminocyclohexyl)methane (BACM); 1-{[4-(aminomethyl)cyclohexyl]oxy}propan-2-amine; and mixtures thereof. Preferred cycloaliphatic diamines are chosen from: cyclohexane-1,3- or -1,4-diamine, 1,3- or 1,4-bis(aminomethyl)cyclohexane, isophoronediamine, bis(4-aminocyclohexyl)methane, and mixtures thereof. Most preferably, the cycloaliphatic diamine is 1,3-bis(aminomethyl)cyclohexane (or 1,3-BAC).

[0024] Component a) may in particular represent from 50 to 100%, preferably from 55 to 95%, more preferably from 60 to 90% in moles, relative to the total number of moles of components a) and d).

[0025] Component b) present in the reaction mixture comprises at least one C3- to C36-hydroxylated monocarboxylic acid. "C3- to C36-hydroxylated monocarboxylic acid" means a compound comprising from 3 to 36 carbon atoms, a single carboxy group (-COOH), and one or more hydroxy groups (-OH), preferably a single hydroxy group. This C3- to C36-hydroxylated monocarboxylic acid may be saturated or unsaturated; it is preferably saturated.

[0026] The hydroxylated monocarboxylic acid b) is preferably selected from monohydroxylated monocarboxylic acids in C16 to C22, such as: 12-hydroxystearic acid (12-HSA), 9-hydroxystearic acid (9-HSA), 10-hydroxystearic acid (10-HSA), 14-hydroxyeicosaneic acid (14-HEA) or mixtures thereof, preferably 12-hydroxystearic acid or a mixture of 12-hydroxystearic acid with one or more compounds selected from 9-hydroxystearic acid (9-HSA), 10-hydroxystearic acid (10-HSA) and 14-hydroxyeicosaneic acid (14-HEA). 12-Hydroxystearic acid can be obtained by hydrogenation of castor oil followed by The hydrolysis of the resulting hydrogenated castor oil. 14-Hydroxyeicosanoic acid can be derived from lesquerolic oil produced by extraction from Lesquerella seeds. Lesquerella oil is typically transesterified with methanol, then the resulting product is hydrogenated and finally hydrolyzed to give 14-hydroxyeicosanoic acid. An example of a polyhydroxylated monocarboxylic acid is 9,10-dihydroxystearic acid.

[0027] Preferably, component b) comprises, or is made up of, 12-hydroxystearic acid.

[0028] Component b) may in particular represent from 10 to 90% by moles, preferably from 20 to 80%, more preferably from 30 to 70% by moles, relative to the total number of moles of components b) and c).

[0029] Component c) comprises at least one non-hydroxylated monocarboxylic acid in the C2-C12 position. A "non-hydroxylated monocarboxylic acid in the C2-C12 position" is defined as a compound comprising 2 to 12 carbon atoms, a single carboxyl group (-COOH), and no hydroxyl groups (-OH). The non-hydroxylated monocarboxylic acid is preferably linear and saturated. The non-hydroxylated monocarboxylic acid preferably comprises 2 to 5 carbon atoms, or 3 to 12 carbon atoms, more preferably 3 to 5 carbon atoms. Optionally, at least one C3-C5 monocarboxylic acid may be associated with the acetic acid or with at least one C6-C12 monocarboxylic acid. Examples of non-hydroxylated monocarboxylic acids suitable as component c) include: acetic, propionic, butanoic, pentanoic, hexanoic, heptanoic, octanoic, nonanoic, decanoic, undecanoic, dodecanoic acid and mixtures thereof.

[0030] Component c) may in particular represent from 10 to 90% by moles, preferably from 20 to 80%, more preferably from 30 to 70% by moles, relative to the total number of moles of components b) and c).

[0031] The reaction mixture is free of C2 to C[2] acyclic diamine. "C2 to C[2] acyclic diamine" means a compound comprising 2 to 12 carbon atoms, two primary amine groups (-NH2), and no ring. "Free of C2 to C[2] acyclic diamine" means a reaction mixture containing less than 1%, in particular less than 0.5%, more particularly less than 0.1%, or even 0% by weight, of C2 to C[2] acyclic diamine relative to the total weight of the reaction mixture. Examples of acyclic diamines in C2 to C12 are: ethylenediamine, 1,3-diaminopropane, 1,4-diaminobutane, 1,5-diaminopentane, 1,6-diaminohexane, 1,7-diaminoheptane, 1,8-diaminooctane, 1,9-diaminononane, 1,10-diaminodecane, 1,11-diaminoundecane, 1,12-diaminododecane and their mixtures.

[0032] In one embodiment of the invention, the reaction mixture comprises in addition to a component (d) comprising at least one C6 to C18 aromatic diamine. A "C6 to C18 aromatic diamine" is defined as a compound comprising 6 to 18 carbon atoms, two primary amine groups (-NH2), and at least one aromatic ring, preferably at least one 6-membered aromatic ring, which may be bonded or fused to another aromatic or non-aromatic ring. Examples of aromatic diamines include C6 to C1M aromatic diamines, notably m- or p-xylylenediamine, m- or p-phenylenediamine, m- or p-tolylenediamine, 3,4'- or 4,4'-diaminodiphenyl ether, 4,4'-diaminodiphenylmethane, and their combinations. m- or p-xylylenediamine (m- or p-XDA) is advantageously used, and more preferably m-xylylenediamine (m-XDA).

[0033] When component d) is present in the reaction mixture, it may in particular represent from 1 to 50% by moles, preferably from 5 to 45% by moles, more preferably from 1 to 40% by moles, relative to the total number of moles of components a) and d).

[0034] The polycondensation reaction between components a), b), c), and optionally d), as described above, can be carried out at a temperature ranging from 140 to 250°C, preferably from 150 to 200°C. The reaction is preferably conducted under an inert atmosphere. The molar ratio between components a) and d) and components b) and c) is generally between 0.9 and 1.1 and is preferably 1:1.

[0035] The diamide obtained after the polycondensation reaction is typically in solid form. It can be micronized by mechanical milling (ball milling, knife milling), optionally followed by sieving, or by air jet. Preferably, the diamide has a volumetric particle size Dv(90) less than or equal to 30 pm, preferably less than or equal to 25 pm, more preferably less than or equal to 20 pm, and even more preferably less than or equal to 15 pm. In particular, Dv(90) can be between 1 pm and 30 pm. The particle size Dv(90) is understood as the volume-based particle size distribution that includes 90% of the particles present in a given sample. This size can notably be determined by laser diffraction.

[0036] The quantity of diamide in the binder composition may in particular range from 0.5 to 20%, in particular from 1 to 15%, more particularly from 2 to 10%, by weight of diamide relative to the total weight of said composition.

[0037] Diamide can notably be used as an organogestor. An organogestor (also called a rheological additive or thixotropic agent) is typically an organic molecule of low molecular weight (i.e., less than 2000 g / mol) that is capable of forming a reversible gel in an organic liquid, particularly at relatively low concentrations (i.e., less than 1% by weight relative to the weight of the organic liquid). An organogestor can modify the rheology of a formulation into which it is introduced. In particular, an organo-freezer can impart a pseudoplastic or thixotropic effect to this formulation. Consequently, an organo-freezer can increase the viscosity of the formulation when the formulation is at rest (no shear stress is applied). The viscosity of the formulation decreases when the formulation is subjected to shear stress. The increase and decrease in viscosity can be determined relative to a control formulation containing no organo-freezer.

[0038] In order to exhibit pseudoplastic or thixotropic properties, a diamide-type organoge must be activated. This activation generally involves applying specific heating conditions under shear for a certain duration.

[0039] Thus, in a first embodiment of the invention, the diamide is in micronized form, as described above, and is activated prior to its addition to or within the organic binder composition. Activation allows the self-assembly of its molecules by non-covalent bonds in order to obtain thixotropic or pseudoplastic properties. The diamide can, for example, be activated by heating at a temperature of 40 to 120°C, more generally 50 to 80°C, for a period of 15 minutes to one hour, in particular 20 to 30 minutes, with a shear rate corresponding to a tangential speed of 4 to 10 ms (i.e., approximately 1000 to 4000 rpm, for example 1500 to 3000 rpm). Alternatively, the diamide can be subjected to a shearing step at room temperature and then placed in an oven at a temperature within the ranges indicated above.

[0040] In a second embodiment, the diamide is in the form of a pre-activated paste in an organic solvent, which is added to the organic binder composition. The term "pre-activated" means that the organogestant possesses thixotropic or pseudoplastic properties. Consequently, a pre-activated organogestant can simply be mixed into a formulation and will not require any further activation to exhibit pseudoplastic or thixotropic properties.

[0041] By "paste" or organogel, we mean a reversible, non-crystalline, and non-glassy solid or semi-solid (gelatinous type) material composed of an organic liquid trapped in a three-dimensional network based on the self-assembly of a structurer (in this case, a diamide) through non-covalent interactions (such as hydrogen bonds, Van der Waals interactions, ir-ji stacking ion pairing, solvophobic forces, and / or ionic coordination). These interactions lead to the formation of a 3D network of microfibrils that immobilize the organic liquid. The organogel can be stable at 25°C for several months, i.e., there is no overall phase separation. During heating and / or stirring, the 3D network can be reversibly fragmented, the organogel can become less viscous, and when heating and / or stirring ceases, the 3D network of microfibrils can re-form.

[0042] In particular, the diamide can be pre-activated in an organic solvent or a mixture of organic solvents and by heating to a temperature equal to or above its activation temperature to allow the self-assembly of its molecules by non-covalent bonds in order to obtain microfibrils.

[0043] The organic solvent can be any organic compound that is liquid at 30°C, preferably within the temperature range of 0°C to 30°C. The organic solvent can comprise one or more plasticizers, one or more reactive solvents, one or more non-reactive solvents, or mixtures thereof. In this description, the term "a plasticizer" or "a solvent" thus covers both a single compound and a mixture of compounds, unless otherwise specified.

[0044] As used here, the term "solvent" refers to a compound capable of at least partially solubilizing the diamide, possibly under heating conditions. The solvent is preferably a polar organic solvent. A polar organic solvent is considered to be a solvent comprising at least one polar group, for example, an alcohol or ester group.

[0045] For the purposes of this document, the term “reactive solvent” means a solvent that includes a reactive functional group, that is, a functional group capable of reacting with at least one component of the formulation (the binder composition) into which the pre-activated organogel paste is added. For example, a reactive solvent may include at least one polymerizable carbon-carbon double bond and / or at least one epoxide ring.

[0046] As used here, the term "non-reactive solvent" refers to a solvent that is inert with respect to the components of the formulation into which the pre-activated organo-freezer paste is added. Generally, a non-reactive solvent is devoid of reactive functional groups as defined above.

[0047] In the sense used here, the term "plasticizer" refers to a compound capable of modifying the mechanical and / or thermal properties of the formulation into which the pre-activated organofreezer paste is added, possibly under heating conditions. For example, a plasticizer may have one or more of the following effects: decreased viscosity, decreased glass transition temperature, increased flexibility, etc.

[0048] Examples of non-reactive solvents are: xylene; alcohols such as methanol, ethanol, butanol, and benzyl alcohol; saturated cyclic 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, the methyl propionate, ethyl propionate, amyl 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), oligoethylene glycol methyl ethers of 2 to 5 oxyethylene units, 1,3-dioxolane, dioxane, dibutyl ether and tetrahydrofuran; ketones such as cyclohexanone; phosphoric acid esters or sulfite esters; nitriles, such as acetonitrile, pyruvonitrile, propionitrile, methoxypropionitrile, dimethylaminopropionitrile, butyronitrile, risobutyronitrile, valeronitrile, pivalonitrile, risovaleronitrile, glutaronitrile, methoxyglutaronitrile, 2-methylglutaronitrile, 3-methylglutaronitrile, adiponitrile and malononitrile;Carbonates such as ethylene carbonate, propylene carbonate, butylene carbonate, dimethyl carbonate, diethyl carbonate, ethyl and methyl carbonate, diphenyl carbonate, methylphenyl carbonate, dipropylene carbonate, methylpropyl carbonate, ethylpropyl carbonate, vinylene carbonate, fluoroethylene carbonate, trifluoropropylene carbonate; and mixtures thereof.

[0049] Examples of non-reactive solvent mixtures are mixtures of xylene with ethanol or butanol, for example in a weight ratio of 1:1 to 4:1.

[0050] In the case where a reactive solvent is used, it is generally chosen from an ethylenically unsaturated compound (i.e., a compound comprising a polymerizable carbon-carbon double bond) or an epoxide (i.e., a compound comprising 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.

[0051] In particular, the reactive solvent may comprise one or more ethylenically unsaturated compounds selected from a (meth)acrylic monomer, a styrenic monomer, a vinyl monomer, an olefinic monomer, an unsaturated polyacid or a derivative thereof, and mixtures thereof.

[0052] As used herein, the term "(meth)acrylic monomer" refers to a monomer comprising a carbon-carbon double bond conjugated to a carbonyl bond (-C(=O)-). Such monomers generally comprise a group (meth)acryloyl. Preferably, the (meth)acrylic monomer is a monofunctional (meth)acrylic monomer, that is, it comprises only one (meth)acryloyl group. The term (meth)acryloyl group is used interchangeably to refer 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 among the alkyl (meth)acrylates (in particular methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, tert-butyl (meth)acrylate, or (meth)acrylate of 2-ethylhexyl); cycloaliphatic (meth)acrylates (including di-cyclopentadienyl (meth)acrylate, norbornyl (meth)acrylate, isobomyl (meth)acrylate (IBO(M)A), tert-butyl cyclohexanol (meth)acrylate (TBCH(M)A), tricyclodecane methanol mono(meth)acrylate and 3,3,5-trimethylcyclohexanol (TMCH(M)A) (meth)acrylate); hydroxyalkyl (meth)acrylates (including 2-hydroxyethyl (meth)acrylate); (meth)acrylic acid; (meth)acrylamide; (meth)acrylonitrile; and mixtures thereof.

[0053] As used herein, the term "styrenic monomer" refers to a monomer that contains a carbon-carbon double bond in the alpha position relative to an aromatic ring. The styrenic monomer may be selected from styrene, alpha-methylstyrene, tert-butylstyrene, ortho-, meta- or para-methylstyrene, ortho-, meta- or para-ethylstyrene, ro-methyl-p-isopropylstyrene, p-chlorostyrene, p-bromostyrene, o,p-dichlorostyrene, o,p-dibromostyrene, ortho-, meta- or para-methoxystyrenes, optionally substituted indenes, optionally substituted vinylnaphthalenes, acenaphthylene, diphenylethylene, vinylanthracene and mixtures thereof.

[0054] As used here, the term "vinyl monomer" refers to a monomer that contains a vinyl group (-CH=CH2) that is not conjugated to a carbonyl group (C=O) or an aromatic group. Vinyl monomers are distinguished from olefinic monomers in that they comprise at least one heteroatom, that is, an atom other than carbon or hydrogen.The vinyl monomer can be chosen from among the vinyl halides (in particular vinyl chloride); vinyl esters (including vinyl acetate, vinyl formate, vinyl propionate, vinyl butyrate, vinyl isobutyrate, vinyl pivalate, vinyl pentanoate, vinyl hexanoate, vinyl octanoate, vinyl 2-ethylhexanoate, vinyl pelargonate, vinyl laurate, vinyl stearate and vinyl versatate, i.e. esters of branched monocarboxylic acids having 6, 9, 10 or 11 carbon atoms (including those available under the references VeoVa® EH, VeoVa® 9, VeoVa® 10 or VeoVa® 11 from Hexion); vinyl ethers (including methyl, ethyl, butyl or isobutyl vinyl ether) and mixtures thereof.

[0055] As used herein, the term "olefinic monomer" refers to a non-aromatic hydrocarbon monomer that contains one or more carbon-carbon double bonds. The olefinic monomer may be selected from ethylene, propene, 1-butene, isobutylene, diisobutylene, 1-nonene, 1-decene, butadiene, or mixtures thereof.

[0056] As used herein, the term "unsaturated polyacid" refers to a compound comprising at least one carbon-carbon double bond and at least two carboxy groups, the carbon-carbon double bond being conjugated to at least one of the carboxy groups. The term "unsaturated polyacid derivative" refers to a compound capable of yielding an unsaturated polyacid in situ, for example, by hydrolysis or ring opening. Examples of suitable unsaturated polyacid derivatives include alkyl esters of unsaturated polyacids and cyclic anhydrides. The unsaturated polyacid or its derivative may be chosen from fumaric acid, maleic acid, itaconic acid, aconitic acid, mesaconic acid, their anhydrides and mixtures thereof.

[0057] Alternatively, the reactive solvent may be a cardanol derivative or a glycidyl ether.

[0058] As used here, the term “cardanol derivative” refers to a compound obtained by mo Chemical modification of cardanol. Cardanol is a bio-based phenolic lipid extracted from cashew nuts (a byproduct of cashew nut processing). Cardanol comprises a phenol ring substituted with an unsaturated fatty chain and can be chemically modified by various reactions. The OH group of the phenolic ring can be converted to an ester group, a phosphate group, an ether, or a glycidyl ether. Alternatively, the unsaturated fatty chain can be epoxidized. Examples of suitable cardanol derivatives include {3-[(8E)-pentadec-8-en-l-yl]phenoxymethyl}oxirane (Cardolite NC-513) or the [(7Z)-pentadec-7-en-l-yl] phenol (Cardolite® NX-2022).

[0059] As used herein, the term "glycidyl ether" refers to a compound comprising a glycidyl ether group of formula:

[0060] [Chem.l]

[0061] Glycidyl ethers can be obtained by reacting an alcohol or a polyol with epichlorohydrin. Examples of suitable glycidyl ethers include C4-C2O alkyl glycidyl ethers (such as octyl, decyl, dodecyl, tetradecyl, or hexadecylglycidyl ether), 1,2- or 1,3-propylene glycol diglycidyl ether, 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, 1,12-dodecanediol diglycidyl ether, and ether 2-methyl-1,3-propanediol diglycidyl ether, neopentylglycol 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-pentane diol diglycidyl ether, glycerol triglycidyl ether, trimethylolmethane triglycidyl ether, trime- triglycidyl ether, thylolethane, trimethylolpropane triglycidyl ether, di(trimethylolpropane) tetraglycidyl ether, pentaerythritol diglycidyl ether, cyclohexane diglycidyl ether, cyclohexane-1,4-dimethanol diglycidyl ether, tricyclodecane diethanol diglycidyl ether, isosorbide diglycidyl ether, pyrocatechol diglycidyl ether, resorcinol diglycidyl ether, cardol diglycidyl 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.

[0062] According to one embodiment, the reactive solvent is a monofunctional (meth)acrylic monomer, preferably an alkyl (meth)acrylate or a cycloaliphatic (meth)acrylate. The pre-activated organofreezer paste obtained from these monomers is particularly suitable as an additive for compositions comprising, as an organic binder, a component of a two-component epoxy / amine reactive system, in which the reactive solvent is capable of reacting with the amine of the epoxy / amine system.

[0063] In the case where a plasticizer is used, said plasticizer is preferably chosen from a polar organic plasticizer which generally comprises at least one polar group chosen from an ether group and / or an ester group and / or an epoxy group.

[0064] Plasticizers comprising at least one ether group may be selected from polyethers, such as homopolymers and / or copolymers of ethylene oxide and / or propylene oxide and / or a mixture of said polyethers (homopolymers and / or copolymers) and / or derivatives thereof, these derivatives including, among others, said polyethers blocked at the end of the chain by an alkoxy group from C1 (methoxy) to C4 (butoxy), or by an ester group from C2 (acetate) to C4 (butyrate), said polyethers having a weight-average molecular weight Mw ranging from 150 to 6000 and preferably from 1000 to 3000. The term "copolymer" should be interpreted as including both statistical copolymers and block copolymers.

[0065] The polyethers most particularly preferred are polyethers which are homopolymers of propylene oxide (polypropylene glycols) of average molecular mass by weight Mw ranging from 1000 to 3000, and more particularly polypropylene glycol (PPG) of Mw equal to 2000, and / or its derivatives chosen from among the monoesters, preferably the monoesters in C2 to C4, or the monoethers in Ci to C4, such as monomethoxylated or monoethoxylated polypropylene glycol.

[0066] Plasticizers comprising at least one ester group may be chosen from monoesters and / or polyesters (polyfunctional esters) obtained from C4 to C2i alcohols, possibly alkoxylated alcohols, for example with 1 to 10 chosen alkoxy motifs from among oxyethylene (OE) and / or oxypropylene (OP), and from among mono- or polyacids with functionalities ranging from 1 to 4, chosen from:

[0067] i) organic acids selected from aromatic acids having a chain length (without CO2H) ranging from C6 to C10 and / or aliphatic acids having a chain length (without -CO2H function) ranging from C4 to C10 and / or cycloaliphatic acids having a chain length (without -CO2H function) ranging from C6 to C10, and

[0068] ii) inorganic acids.

[0069] Aromatic acid esters may be selected from phthalic (phthalates) and trimellitic (trimellitates) esters. Aliphatic acid esters may be selected from adipic (adipates) esters, citric (citrates) esters, sebacic (sebacates) esters, and azelaic (azelates) esters. Cycloaliphatic acid esters may be selected from tetrahydrophthalic (tetrahydrophthalates) esters and hexahydrophthalic (hexahydrophthalates) esters. Inorganic acid esters can be selected from sulfonic esters (sulfonates), including alkylsulfonates in C10 to C2i, sulfuric esters (sulfates), sulfinic esters (sulfinates), phosphoric esters (phosphates), phos-phonic esters (phosphonates) and phosphinic esters (phosphinates).

[0070] Finally, in the case where the plasticizer includes at least one epoxy group, it can be chosen from epoxidized vegetable oils such as epoxidized soybean oil or epoxidized linseed oil, and epoxidized alkyl esters of fatty acids such as epoxidized methyl oleate, epoxidized isoamyl stearate or 2-ethylhexyl stearate.

[0071] Among the preferred plasticizers, mention may be made of those comprising at least one C6 to C10 aromatic acid ester group, in particular plasticizers selected from mono- and / or dialkyl phthalates, and even more preferably from dialkyl phthalates, or hexahydrophthalates, in which said alkyls are identical or different and selected from alkyls in C7 to C8, and preferably alkyls in C10 to C12. The most preferred plasticizers in this family of dialkyl (hexahydro)phthalates are diisoundecyl phthalate and diisononyl hexahydrophthalate.

[0072] Usually, the diamide is present in a weight ratio, relative to the organic solvent, ranging from 1:1 to 1:10 and preferably from 1:3 to 1:6.

[0073] The diamide as described above is added to a composition comprising at least one crosslinkable organic binder (sometimes referred to herein as a "formulation"). As used herein, the term "binder" refers to a material or substance that ensures the plasticity and cohesion of the various constituents of a formulation after drying and / or hardening. As used herein, the term "organic binder" refers to a binder comprising carbon and hydrogen atoms. As used herein, the term "crosslinkable organic binder" refers to an organic binder that is capable of forming one or more covalent bonds with itself and / or with another molecule.

[0074] The organic binder can be an ethylenically unsaturated binder crosslinkable by radical means or an organic binder crosslinkable by chemical reaction (in particular by epoxy-amine reaction, by alcohol-isocyanate reaction, by amine-isocyanate reaction, by carbonyl-amine reaction, by carbonyl-hydrazide reaction, by Michael addition, by aza-Michael or by thio-Michael addition, by thiol-ene or thiol-yne reaction, by cycloaddition reaction, by polycondensation).

[0075] Thus, according to one embodiment, the organic binder is crosslinkable, either chemically (by reaction with atmospheric moisture or with another molecule), or thermally (in the presence of a radical initiator such as a peroxide or an azo compound), or by redox reaction (in the presence of an oxidant such as a peroxide and a reductant such as a ferrous compound, a carboxylic acid, sodium sulfite, sodium bisulfite, sodium metabisulfite, sodium hydroxymethanesulfinate, or rongalite), or by irradiation under radiation such as UV radiation (in the presence of at least one photoinitiator) and / or EB radiation (electron beam, without an initiator), including self-crosslinking at room temperature. The organic binder can be crosslinkable by itself or in combination with another component of the formulation (multi-component system).

[0076] Generally, the binder comprises at least one monomer or at least one polymer (including oligomers) having at least one functionality selected from a polymerizable carbon-carbon double bond, a carbon-carbon triple bond, a reactive group enabling its self-crosslinking or its reaction with another component of the formulation, and combinations thereof. Examples of suitable reactive groups are amino, amido, hydroxyl, thiol, epoxy, oxetane, carboxyl, carbonyl, urea, cyclic carbonate, cyclic anhydride, silyl, isocyanate, azide, and combinations thereof. It may thus comprise at least one monomer or at least one polymer selected from: an ethylenically unsaturated monomer (such as those described above for the reactive solvent), an ethylenically unsaturated oligomer, an unsaturated polymer (in particular an unsaturated polyester, an alkyd resin, a uralkyd, or a modified alkyd),an oleoresin (in particular rosin or resin acid), an epoxide (such as those described previously for the reactive solvent), an epoxy resin, a polyol, a polyol polymer (in particular a hydroxylated acrylic resin, a polyester polyol or a polyether polyol), a polyisocyanate, urea-formaldehyde, a phenolic resin, a hydrazide, an amine (in particular melamine), a dicyandiamide, a hydroxyalkylamide, a silylated polymer (in particular a silylated polyurethane, a silylated polysiloxane, a silylated polysulfide, a silylated polyether, a silylated polyether / urethane, a silylated polyester, a silylated polybutadiene), an acrylic resin functionalized with a reactive group (in particular as described previously), a styrene-acrylic resin functionalized with a group, reactive (in particular as described above), a poly(vinyl chloride), a polychloroprene or SBR type elastomer or butyl rubber, and mixtures thereof, without this list being exhaustive.

[0077] For example, the organic binder composition according to the invention can be a single-component sealant composition based on silylated polymer and preferably based on silylated polyether or silylated polyurethane, such as the products marketed by KANEKA under the names MS POLYMER® and SILYL®.

[0078] In a more particular case, said crosslinkable organic binder may be chosen from a component of one of the following two-component systems: epoxy-amine or epoxy-polyamide systems comprising at least one epoxy resin having at least two epoxy groups and at least one amine or polyamide compound having at least two amine groups (resulting in particular from the condensation of an acid dimer with a polyamine); polyurethane systems comprising at least one polyisocyanate and at least one polyol; polyol-melamine systems in which the polyol is optionally a hydroxylated acrylic resin, a polyester or a polyether polyol; polyester systems based on at least one epoxy or a reactive polyol with at least one corresponding acid or anhydride.

[0079] The composition comprising the crosslinkable organic binder and the diamide described above can be used in the manufacture of a coating, selected in particular from among paints, varnishes, inks and gel coats; an adhesive; a sealant; a sealant; a chemical sealant; a molded object; an object obtained by 3D printing; preferably a coating. The composition can, for example, be applied to various substrates by spraying, for example with a spray gun, or by brush or roller.

[0080] The pre-activated organoge paste may be present in these compositions at a content of 1 to 30%, and preferably 2 to 25% by weight, and said diamide may be present as dry active material (either in the form of micronized powder, or as a constituent of the pre-activated paste) at a content of 0.2 to 8%, and preferably 1 to 6% by weight, relative to the weight of said formulation.

[0081] The composition may include other components, such as fillers, plasticizers, wetting agents or pigments.

[0082] In one embodiment of the invention, the composition is prepared by adding the pre-activated organofreezer paste described above to the remaining constituents of said composition, and then homogenizing the mixture with a mixer and / or a planetary mixer and / or a high-speed disperser, without the need, at this stage, to apply a thermal activation treatment, where "high speed" means tangential speeds ranging from 2 to 15 ms*. This embodiment is particularly well suited to the formulation of epoxy, acrylic, or resin-based paints. alkyd. The end user can activate the organogestor before its introduction into said formulation or the end user can activate the organogestor in situ (directly in the formulation).

[0083] In a preferred embodiment of the invention, the diamide is introduced into the composition in micronized form and an activation step is carried out by the formulator. The activation conditions may, in particular, be as described above. EXAMPLES

[0084] The invention will be better understood in light of the examples below, which are given for purely illustrative purposes and are not intended to limit its scope. Raw materials used

[0085] [Tables 1] Product Function Commercial Reference Supplier Hexamethylenediamine (HMDA) Reagent Hexamethylenediamine 98% Aldrich 1,3-Bis(aminomethyl)cyclohexane (1,3-B AC) Reagent 1,3-BAC ITOCHU Ethylenediamine (EDA) Reagent Ethylenediamine > 99.5% (GC) Aldrich 12-Hydroxystearic acid (12-HSA) Reagent 12-HSA Jayant Agro Heptanoic acid (C7) Reagent OLERIS® n-Heptanoic acid Arkema Hexanoic acid (C6) Reagent Capric acid UNIOLEO FA 1099 Unilever Propionic acid (C3) Reagent ACS Reagent >995% Aldrich Acetic Acid (C2) Reagent Acetic Acid 100% Aldrich h3PO2 Antioxidant H3PO2 (50% by weight) Febex Epoxy Resin Binder Araldite® GZ 7071X75 Huntsman Epoxy Resin Binder Araldite® GY 783 BD Huntsman STP Resin (Silyl Terminated Polyether) Binder MS POLYMER® S203H Kaneka Degassing Agent Byk® A530 Byk Dispersant Disperbyk® 110 Byk Titanium Dioxide Pigment Tiona® 595 Tronox Zinc Phosphate Pigment ZP 10 Heucophos Talc Additive Finntalc® MO5 Mondo Minerals Silica Filler C-400 Sibelco n-Butanol Solvent n-Butanol Aldrich Polyamide Hardener Crayamid® 140 Arkema, Diisooundecyl phthalate Plasticizer JAYFLEX DIUP ExxonMobil Xylene Solvent Xylene (Synthetic Grade) Aldrich Methods and tests used

[0086] The formulations are evaluated using the following tests: Spill resistance test:

[0087] This test is performed using a smear tester (Levelling / Sagging Tester from Sheen Instruments) which determines a coating's resistance to smearing due to gravity. This tester, made of stainless steel and equipped with a flat blade, has notches of increasing value. The test consists of depositing different strips of paint of parallel thickness onto a contrast card using the smear tester. The contrast card is immediately placed vertically, with the thinnest film at the top. The thickness at which the strips meet indicates the tendency to smear. Viscosity evaluation:

[0088] This test is performed using a Brookfield® RV viscometer at 25°C (movement: S 4). The rotation speed of the moving part is set to 1 rpm (revolutions per minute) and the viscosity of each paint after stabilization is measured. The operation is repeated at speeds of 5 rpm, 10 rpm, 50 rpm, and 100 rpm. Gelation test:

[0089] This test is performed using a Kinexus Pro rheometer (Malvem). A stress sweep from 0.1 to 15,000 Pa is carried out at 25°C under a frequency of 1 Hz, and the elastic modulus (G' (in Pa)) is measured to evaluate the structural level (i.e., the strength) of the gel formed. The air gap is set to 1 mm for the plane-to-plane geometry used. A visual assessment of the gel's appearance is also performed. Preparation and characterization of diamides

[0090] Example 1: Diamide based on 1,3-BAC, 12-HSA, propionic acid and acetic acid

[0091] 345.49 g (1.10 mol) of 12-hydroxystearic acid, 20.36 g (0.27 mol) of pro-acid Pionic acid and 16.49 g (0.27 mol) of acetic acid were introduced under a stream of nitrogen into a 1-liter round-bottom flask equipped with a thermometer, a Dean-Stark apparatus, a condenser, and a stirrer. 0.41 g of an aqueous H3PO2 solution (50 wt%) was added.

[0092] The mixture was heated to 120°C, still under a flow of nitrogen. 117.24 g (0.82 mol) of 1,3-BAC were introduced dropwise, with stirring while maintaining the temperature below 140°C. After the addition of the diamine, the mixture was heated to 190°C, still under a flow of nitrogen. The removed water began to accumulate. The reaction was carried out in a Dean Stark apparatus at 150°C. The reaction was monitored by measuring the acid value and amine value. When the acid and amine values ​​were below 10 (in mg KOH / g), the reaction mixture was cooled to 150°C and then poured into a silicone mold. Once cooled to room temperature, the product was ground by opposed-air jet micronization.

[0093] For Examples 2 to 12, the same procedure was used, but with the proportions of reactants shown in Table 2 below:

[0094] [Tables2] Example Diamine / Acid Reagents Mole 1 1,3-BAC 12-Hydroxystearic Acid Propionic Acid Acetic Acid 0.82 1.10 0.27 0.27 2 1,3-BAC 12-Hydroxystearic Acid Acetic Acid 0.83 1.11 0.55 3 1,3-BAC 12-Hydroxystearic Acid Propionic Acid 1.10 1.10 1.10 4 1,3-BAC 12-Hydroxystearic Acid Hexanoic Acid 1.10 1.10 1.10 5 1,3-BAC 12-Hydroxystearic Acid Heptanoic Acid 1.10 0.80 1.40 6 (comparative) Hexamethylenediamine 12-Hydroxystearic Acid Propionic acid Acetic acid 0.86 1.15 0.29 0.29 7 (comparative) Hexamethylenediamine 12-Hydroxystearic acid Acetic acid 0.87 1.16 0.58 8 (comparative) 1,3-BAC Hexamethylenediamine 12-Hydroxystearic acid Propionic acid Acetic acid 0.41 0.43 1.12 0.28 0.28 9 (comparative) Ethylenediamine 12-Hydroxystearic acid Propionic acid Acetic acid 0.95 1.27 0.32 0.32 10 Ethylenediamine 1.05 (comparative) 12-Hydroxystearic acid Propionic acid 1.05 1.05 11 Ethylenediamine 1.00 (comparative) 12-Hydroxystearic acid Hexanoic acid 1.10 0.90 12 Hexamethylenediamine 1.10 (comparative) 12-Hydroxystearic acid Heptanoic acid 0.80 1.40

[0095] Evaluation of rheological performance in a paint formulation

[0096] The prepared diamides were evaluated in high solids (or high dry extract) reactive epoxy paint formulations in xylene. 1) Preparation of paint formulations

[0097] A so-called "millbase" formulation was prepared in the proportions shown in Table 3 below and in the following manner:

[0098] The following successive operations were carried out in a dispersing bowl (Dispermill® 2075 yellow line, supplier: Erichsen) heated by a double-jacketed system:

[0099] 1.1) Introduction of epoxy binders, dispersant and degassing agent. Homogenization was carried out for 2 minutes at 800 rpm.

[0100] 1.2) Introduction of fillers and pigments, followed by grinding at 3000 rpm for 30 minutes using a 7 cm blade. The double-walled bowl allowed this step to be carried out at room temperature with a water bath at 20°C.

[0101] 1.3) Introduction of solvent (butanol) and homogenization.

[0102] [Tables3] A-Millbase COMPOSITION Function % by weight Araldite® GZ 7071X75 Binder 17.3 Araldite® GY 783 BD Binder 12.9 Byk® A530 Degassing agent 0.5 Disperbyk® 110 Dispersant 0.5 Tiona 595 (Titanium dioxide) Pigment 6 ZP 10 (Zinc phosphate) Pigment 7.5 Finntalc MO5 Filler 9.4 Silica C-400 Filler 19.0 n-Butanol Solvent 5.4 Diamide Rheology additive 0.8 TOTAL 79.3 2) Activation of the diamide in the formulation

[0103] 24 hours after the preparation of the millbase, the formulation was again dispersed using a 4 cm blade at 3000 rpm. The diamide to be evaluated was introduced into the millbase and activated in situ at 55°C, for 20 minutes and at 3000 rpm.

[0104] The evaluation was carried out 24 hours after activation and 30 minutes after the addition of the hardener diluted in xylene to the millbase (see Table 4).

[0105] [Tables4] B-Composition of the hardener % by weight Crayamid® 140 8.8 Xylene 11.9 TOTAL 20.7

[0106] The paints thus obtained were adjusted in application viscosity with a xylene / butanol mixture (1 / 1 by weight) to about 0.4 P or about 40 mPa.s (more precisely to 0.37-0.38 P or 37-38 mPa.s) measured on cone 4 at 25°C at 2500 s 1 using a Brookfield® CAP 1000 viscometer. The amount of 1 / 1 xylene / butanol mixture used for viscosity adjustment may vary, but generally by less than 1% variation from one test to another.

[0107] After adjustment, the paint was mixed / homogenized at 1500 rpm for 2 minutes, then left to stand for 30 minutes before evaluation 24 hours later late.

[0108] 3) Evaluation of the rheology of epoxy paint formulations

[0109] Different paint formulations were prepared, according to the proportions in Tables 3 and 4, with the diamides mentioned in Table 2 and at 55 °C, according to the protocol described above.

[0110] The results of the resistance to dripping test and the rheological evaluation (viscosity and thixotropy index TI 1 / 10 and TI 5 / 50) are presented in Table 5 below. [YES] [Tables 5] Amide evaluated Brookfield viscosity at 25 °C (mPa·s) at different rotation speeds (1.5, 10, 50 and 100 rpm) Thixotropic index Sagging resistance 1 5 10 50 100 TI 1 / 10 TI 5 / 50 (pm) 1 21 200 6 360 4 100 1 680 1 216 5.17 3.79 550 6 (comparative) 11 400 3 800 2 520 1 156 906 4.52 3.29 425 8 (comparative) 13 000 4 120 2 680 1 204 916 4.85 3.42 425 2 17 000 5 240 3 360 1 440 1 066 5.05 3.64 450 7 (comparative) 15 200 4 920 3 200 1 396 1 050 4.75 3.52 425

[0112] These results show that the cycloaliphatic diamine-based diamides according to the invention (Examples 1 and 2) exhibit better rheological performance than an acyclic diamine-based diamide, used alone (Examples 6 and 7, respectively) or in a mixture (Example 8) with a cycloaliphatic diamine, in particular higher resistance to sagging and viscosity, as well as better thixotropic behavior. Furthermore, when the diamide is prepared from a mixture of non-hydroxylated C2 and C3 monocarboxylic acids (Example 1), its resistance to sagging is significantly higher than when it is prepared from a single C2 monocarboxylic acid (Example 2).

[0113] Evaluation of gelling strength in an STP resin / plasticizer mixture

[0114] The prepared diamides were evaluated in formulations containing a resin STP and a plasticizer.

[0115] 1) Preparation of mixtures containing 5% diamide

[0116] The formulation was prepared in the proportions shown in Table 6 below and in the following manner:

[0117] The binder, plasticizer, and diamide were introduced into a dispersing bowl (Dispermill® 2075 yellow line, supplier: Erichsen) whose temperature was regulated by a double-jacketed system at 25°C. Homogenization was carried out for 5 minutes at 1000 rpm. The mixture was then placed in an oven heated to 40°C for 2 hours before evaluating the gelling properties.

[0118] [Tableauxô] Composition Function % by mass Diamide Organofreezer 5.0 MS Polymer - S203H Crosslinkable organic binder 47.5 Diisoundecyl phthalate (DIUP) Plasticizer 47.5 TOTAL 100 2) Evaluation of gelling strength

[0119] Different mixtures were prepared, according to the proportions in Table 7, with the diamides in Table 2. The results of the evaluation of the gelling strength are presented in Table 7 below.

[0120] [Tables?] Evaluated Amide G'max (Pa) Gel Appearance* 1 21.7 + 3 283.0 ++ 4 332.0 ++ 5 500.1 ++ 6 (comparative) 0.12 - 8 (comparative) 5.9 - 9 (comparative) 0.47 - 10 (comparative) 21.1 + 11 (comparative) 2.6 - 12 (comparative) 3.9 -

[0121] *The appearance of the gel was assessed visually and using G' values:

[0122] - gelled liquid (with G' > 100 Pa): « ++ »

[0123] - viscous liquid (with 20 < G' < 100 Pa): « + »

[0124] - liquid (with G' < 20 Pa): « - »

[0125] These results show that diamides based on cycloaliphatic diamine and a mixture of non-hydroxylated monocarboxylic acids at C2 and C3 (Example 1) are more effective organofreezers than their counterparts based on acyclic diamine used alone (Example 6 or 9) or in combination with a cycloaliphatic diamine (Example 8). This observation is also confirmed when the diamides based on cycloaliphatic diamine contain a single non-hydroxylated monocarboxylic acid at C3 (Example 3 vs. Example 10), C6 (Example 4 vs. Example 11), or C7 (Example 5 vs. Example 12). They allow, in all cases, the gelling of the STP / plasticizer mixture to form gels with elastic moduli > 280 Pa. In comparison, acyclic diamine-based diamides (ethylene diamine or hexamethylene diamine) do not increase, or only very slightly increase, the viscosity of the mixture.

Claims

Demands

1. Use of a diamide in the manufacture of a composition comprising at least one crosslinkable organic binder, characterized in that said diamide is obtained from a reaction mixture comprising: a) at least one C6 to Ci8 cycloaliphatic diamine, b) at least one C3 to C36 hydroxylated monocarboxylic acid, c) at least one C2 to Ci2 non-hydroxylated monocarboxylic acid, the reaction mixture being devoid of C2 to Ci2 acyclic diamine.

2. Use according to claim 1, characterized in that component a) comprises at least one C6 to C18 cycloaliphatic diamine selected from: cyclohexane-1,2-, -1,3- or -1,4-diamine; 2- or 4-methylcyclohexane-1,3-diamine; isophoronediamine; 1,2-, 1,3- or 1,4-bis(aminomethyl)cyclohexane; decahydronaphthalenediamine; bis(3-methyl-4-aminocyclohexyl)methane; bis(4-aminocyclohexyl)methane; 1-{[4-(aminomethyl)cyclohexyl]oxy}propan-2-amine, and mixtures thereof; preferably cyclohexane-1,3- or -1,4-diamine, 1,3- or l,4-bis(aminomethyl)cyclohexane, isophoronediamine, bis(4-aminocyclohexyl)methane, and mixtures thereof; more preferably l,3-bis(aminomethyl)cyclohexane.

3. Use according to claim 1 or 2, characterized in that component b) comprises at least one C3 to C36 hydroxylated monocarboxylic acid selected from: 12-hydroxystearic acid, 9-hydroxystearic acid, 10-hydroxystearic acid, 14-hydroxyeicosaneic acid or mixtures thereof, preferably 12-hydroxystearic acid or a mixture of 12-hydroxystearic acid with one or more compounds selected from 9-hydroxystearic acid, 10-hydroxystearic acid and 14-hydroxyeicosaneic acid.

4. Use according to any one of claims 1 to 3, characterized in that component c) comprises at least one non-hydroxylated monocarboxylic acid comprising from 2 to 5 carbon atoms, or from 3 to 12 carbon atoms, more preferably from 3 to 5 carbon atoms.

5. Use according to any one of claims 1 to 4, characterized in that the reaction mixture further comprises a component d) comprising at least one C6-Ci8 aromatic diamine, said C6-Ci8 aromatic diamine being preferably selected from m- or p-xylylenediamine, m- or p-phenylenediamine, m- or p-tolylenediamine, 3,4'- or 4-4'-diaminodiphenyl ether, 4,4'-diaminodiphenylmethane and combinations thereof, preferably m- or p-xylylenediamine, more preferably m-xylylenediamine.

6. Use according to any one of claims 1 to 5, characterized in that the diamide is in the form of a pre-activated paste in an organic solvent.

7. Use according to any one of claims 1 to 5, characterized in that the diamide is in micronized form.

8. Use according to any one of claims 1 to 7, characterized in that the crosslinkable organic binder comprises at least one monomer or at least one polymer selected from: an ethylenically unsaturated monomer; an ethylenically unsaturated oligomer; an unsaturated polymer, in particular an unsaturated polyester, an alkyd resin, a uralkyd or a modified alkyd; an oleoresin, in particular rosin or a resin acid; an epoxide; an epoxy resin; a polyol; a polyol polymer, in particular a hydroxylated acrylic resin, a polyester polyol or a polyether polyol; a polyisocyanate; urea-formaldehyde; a phenolic resin; a hydrazide; an amine, in particular melamine; a dicyandiamide; a hydroxyalkylamide; a silylated polymer, in particular a silylated polyurethane, a silylated polysiloxane, a silylated polysulfide, a silylated polyether, a silylated polyether / urethane, a silylated polyester, a silylated polybutadiene;an acrylic resin functionalized with a reactive group; a styrene-acrylic resin functionalized with a reactive group; a poly(vinyl chloride); a polychloroprene or SBR type elastomer or butyl rubber; and mixtures thereof.

9. Composition comprising at least one crosslinkable organic binder and at least one diamide as defined in any one of claims 1 to 8.

10. Use of the composition according to claim 9 for the manufacture of a coating, selected in particular from gelled paints, varnishes, inks and finishing coatings; of a glue or adhesive; of a sealant; of a sealant; of a chemical sealant; of a molded object; of an object obtained by 3D printing; preferably of a coating.