Monomers for thermosetting epoxy resins or adhesives

Abstract

The present invention relates to epoxy precursors, a process for their preparation, and their use as monomers for the preparation of thermosetting resins or corresponding adhesives.

Description

[0001]DESCRIPTION OF MONOMERS FOR THERMOSETTING EPOXY RESINS OR ADHESIVES FIELD OF THE INVENTION The field of the present invention is the synthesis of epoxy precursors and their use as monomers for the preparation of thermosetting resins or associated adhesives. More specifically, the present invention relates to the use of polyfunctional phenolic aromatic compounds derived from renewable resources, and not from petroleum, natural gas, coal, or other fossil resources, exhibiting improved environmental and safety properties (HSE properties) and resulting in thermosetting resins that do not exhibit performance degradation in use. STATE OF THE ART Currently, among the polyfunctional phenolic aromatic compounds, one can notably mention bisphenol A diglycidyl ether (DGEBA or BADGE), manufactured from bisphenol A (BPA) and epichlorohydrin (ECH).BPA is classified as a Carcinogenic, Mutagenic, and Reprotoxic (CMR) substance, specifically a category 2 reprotoxicant and an endocrine disruptor. In recent years, several solutions have been implemented to develop compounds with a low environmental footprint and reduce their toxicity. For example, in 2007, Solvay introduced the EPICEROL® process for the bio-based production of hydroxyethyl starch (HES) from glycerol. BPA can also be obtained by reacting phenol, obtained by distilling forestry industry waste, with acetone produced through fermentation (SuperSap® prepolymer from Entropy Resins). However, using bio-based and renewable BPA does not alter the inherent danger of this substance, which remains classified as CMR regardless of its origin.Therefore, it is preferable to improve the properties with new, less polluting and non-toxic precursors for humans, rather than implementing a "drop-in" product-for-product substitution that would retain the potential hazards of the products used. Furthermore, in certain applications, such as food contact (coatings for metal containers, tanks, etc.) or the rehabilitation of aging drinking water pipes by spray lining, the potential leaching of BPA from the degradation of thermosetting materials based on DGEBA is a concern for public authorities. (Rajarsärkkä et al. Water Res. 2016, 103, 133-140; Cantoni et al. Sci. Total Environ. 2021, 783, 146908; Lipke et al. Eur. J. Pharm. Biopharm. 2016, 101, 1-8).TECHNICAL PROBLEM The technical problem that the present invention aims to solve is therefore to obtain new polyfunctional epoxidized aromatic phenolic compounds from renewable resources that exhibit improved HSE properties. SUMMARY OF THE INVENTION Thus, a first object of the invention is a compound of formula (I):. in which: - R1 and R3, identical, denote a group with the following formula (II): in which -E represents a single bond or a C1-C12 hydrocarbon divalent group possibly comprising one or more heteroatoms; - X1, X2 and X3, identical or different, represent a hydrogen atom, a C1-C6 alkyl or a C6-C aryl 14, and / or -X1 and X3 or X2, or a carbon atom from the divalent hydrocarbon group of E and X3 or X2 can be bonded together with the carbon atoms of the epoxide group to form a C4-C8 carbocycle or a heterocycle with 5 to 8 members; - the symbol (*) represents the point of attachment of group (II) to the rest of the compound of formula (I); - R5 represents -O-X4, with X4 representing a C1-C18 alkyl, a C6-C14 aryl, a C3-C7 cycloalkyl, or a (C6-C14)aryl-(C1-C6)alkyl; - R2, R4, and R6, whether identical or different, represent a hydrogen atom or a C1-C alkyl. 24 A second object of the invention is a process for preparing a compound of formula (I) according to the invention, comprising a step b) of bringing the following compounds into contact: - a compound of the following formula (I-2): in which: - R1' and R3' of formula (I-2) denote an -OH group; - R5 represents -O-X4, with X4 representing a C1-C18 alkyl, a C6-C14 aryl, a C3-C7 cycloalkyl, or a (C6-C14)aryl-(C1-C6)alkyl; - R2, R4, and R6, identical or different, represent a hydrogen atom or a C1-C24 alkyl; - a compound of the following formula (II-1): in which: - Y2 represents a function capable of reacting with an -OH group to form an ether bond; - E represents a single bond or divalent hydrocarbon group in the C1-C12 range, possibly comprising one or more heteroatoms; - X1, X2, and X3, identical or different, represent a hydrogen atom, a C1-C6 alkyl group, or a C6-C aryl group. 14, and / or -X1 and X3 or X2, or a carbon atom from the divalent hydrocarbon group of E and X3 or X2 can be linked together with the carbon atoms of the epoxy group to form a C4 to C8 carbocycle or a heterocycle having 5 to 8 members. A third object of the invention is the use of a compound of formula (I) according to the invention as a precursor of polymeric materials, in particular thermosetting materials, or as an adhesive. A fourth object of the invention is a process for preparing a thermosetting material comprising a polymerization step of a compound of formula (I) according to the invention; optionally, the process further comprises a crosslinking step. A fifth object of the invention is a thermosetting material obtainable by the preparation process described above. DEFINITIONS In this document, unless expressly stated otherwise, all percentages (%) indicated are percentages (%) in moles.Any range of values ​​designated by the expression "between a and b" as well as by the expression "from a to b" means the range of values ​​from a to b (that is, including the strict bounds a and b). For the purposes of this invention, "hydrocarbon chain" means a chain comprising one or more carbon atoms and one or more hydrogen atoms. For the purposes of this invention, "Cx-Cy alkyl group" means a monovalent, saturated, linear or branched hydrocarbon chain comprising x to y carbon atoms; x and y being integers. For example, for C1-C6 alkyl groups, we can cite methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isoamyl, neopentyl, or hexyl groups, preferably methyl, ethyl, propyl, or isopropyl.For example, C1-C12 alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isoamyl, neopentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl. For example, C1-C4 alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, and tert-butyl. A "Cx-Cy cycloalkyl group," as used in the present invention, is a saturated cyclic hydrocarbon chain comprising x to y cyclic carbon atoms. A cycloalkyl may be monocyclic or bicyclic, preferably monocyclic. Examples of C3-C7 cycloalkyl groups include cyclopropyl, cyclopentyl, cyclohexyl, and cycloheptyl. The term "C1-Cj aryl" refers to an aromatic hydrocarbon group containing from i to j carbon atoms, where i and j are integers. This group may have one or more fused rings.Advantageously, this refers to phenyl. For the purposes of this invention, a "Cx-Cy carbocycle" is defined as a saturated or instanominated non-aromatic cyclic hydrocarbon group comprising x to y carbon atoms. A carbocycle may be monocyclic or polycyclic. When the carbocycle is polycyclic, it comprises at least two, advantageously two or three, fused, bridged, or spiral rings. For example, it may be a saturated carbocycle, particularly at C3-C8. Examples include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, and cyclooctane. It may also be an unsaturated carbocycle, that is, one comprising at least one carbon-carbon double or triple bond, particularly at C3-C8. Examples include the groups cyclopropene, cyclobutene, cyclopentene, cyclohexene, 1,4-cyclohexadiene, cycloheptene, cycloheptyne, cyclooctene, and cyclooctyne.By "heterocycle having x to y links", we mean, in the sense of the present invention, a non-aromatic cycle having x to y links, saturated or unsaturated, monocyclic or polycyclic, (including rings), of which one or more, advantageously 1 to 4, even more advantageously 1 or 2, cyclic atom(s) is / are a heteroatom, such as for example sulfur, nitrogen or oxygen atoms, the other cyclic atoms being carbon atoms. These may include, in particular, the pyrrolidine, piperidine, piperazine, morpholine, pyrazolidine, imidazolidine, azepane, thiazolidine, isothiazolidine, oxazocane, thiazepane, and benzimidazolone groups. For the purposes of this invention, "(C1-Cj)aryl-(Cx-Cy)alkyl" means an aryl group C1-Cj, as defined above, linked to the rest of the molecule via a Cx-Cy alkyl group, as defined above. Examples include the benzyl and 1-phenylethyl groups.The term "heteroatom" refers to any atom other than carbon or hydrogen, such as sulfur, nitrogen, or oxygen atoms. The term "halogen atom" or "halogen" refers, for the purposes of this invention, to fluorine, chlorine, bromine, and iodine atoms. The term "stereoisomer" refers, for the purposes of this invention, to a configurational isomer, and in particular a geometric or optical isomer. Geometric isomers result from the different positions of substituents on a double bond, which may then have a Z or E configuration. Optical isomers result, in particular, from the different spatial positions of substituents on a carbon atom containing four different substituents. This carbon atom then constitutes a chiral or asymmetric center. Optical isomers include diastereomers and enantiomers.Optical isomers that are mirror images of each other but not superimposable are designated as "enantiomers." Optical isomers that are not mirror images of each other are designated as "diastereomers." A mixture containing equal amounts of two individual enantiomeric forms of opposite chirality is designated as a "racemic mixture." According to the present invention, the disclosed compounds encompass all stereoisomers of said compounds. "Room temperature" is understood, for the purposes of this invention, to be a temperature generally ranging from 15°C to 40°C, preferably from 20°C to 30°C, and in particular from approximately 25°C. The compounds mentioned in the description may be of fossil origin or bio-based. In the latter case, they may be, in whole or in part, derived from biomass or obtained from renewable raw materials derived from biomass.Similarly, the compounds mentioned can also be derived from the recycling of materials already used; that is, they can be partially or totally produced through a recycling process, or obtained from raw materials themselves derived from a recycling process. For the purposes of this invention, the term "a" or "an," as in the expression "a chain" or "an atom," for example, means "one or more" or "at least one." "Approximately" is understood in this description to mean that the value in question may be 10% lower or higher, in particular 5%, and especially 1% higher, than the value indicated. DETAILED DESCRIPTION OF THE INVENTION For the purposes of this invention, the various embodiments presented in the description as a whole can be used alone or in combination with one another, without any limitation on the combinations.Compound of formula (I) The object of the present invention relates to a compound of formula (I):. in which: - R1 and R3 are identical and designate a group according to the following formula (II): in which -E represents a single bond or a C1-C12 hydrocarbon divalent group possibly comprising one or more heteroatoms; - X1, X2, and X3, identical or different, represent a hydrogen atom, a C1-C6 alkyl, or a C6-C14 aryl, and / or - X1 and X3 or X2, or a carbon atom from the hydrocarbon divalent group of E and X3 or X2, may be bonded together with the carbon atoms of the epoxide group to form a C4-C8 carbocycle or a heterocycle having 5 to 8 members; - the symbol (*) represents the point of attachment of group (II) to the rest of the compound of formula (I); - R5 represents -O-X4, with X4 representing a C1-C18 alkyl, a C6-C14 aryl, a C3-C7 cycloalkyl, or a (C6-C14)aryl-(C1-C6)alkyl ;- R2, R4 and R6, identical or different, represent a hydrogen atom or an alkyl in C1-C24.Advantageously, R2, R4 and R6 represent, identical or different, a hydrogen atom or an alkyl group in C1-C12, preferably in C1-C6, more preferably in C1-C4. Preferably, R2, R4 and R6 represent a hydrogen atom. E may represent a divalent hydrocarbon group in C1-C12, in particular in C1-C10, in particular in C1-C8, preferably in C1-C6, preferably in C1-C4, typically in C1 or C2, possibly comprising one or more heteroatoms, in particular an alkyl group in C1-C12, in particular in C1-C10, in particular in C1-C8, preferably in C1-C6, preferably in C1-C4, typically in C1 or C2, possibly comprising one or more heteroatoms. When present, heteroatoms are preferably chosen from S, O and N, especially from O and N, preferably are O. Preferably, E does not include any heteroatoms. E can represent –(CH2)n- with n an integer equal to 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12.Preferably, X1, X2 and X3, whether identical or different, represent a hydrogen atom or a C1-C6 alkyl. Advantageously, X1 represents a hydrogen atom. Advantageously, X2 and X3 each represent a hydrogen atom or a C1-C6 alkyl group, such as a methyl group. Advantageously, X1 represents a hydrogen atom and X2 and X3, whether identical or different, represent a hydrogen atom or a C1-C6 alkyl group, preferably a hydrogen atom, or a C1-C4 alkyl group, preferably a hydrogen atom or a methyl group. In one embodiment, X1, X2, and X3 represent a hydrogen atom. In another embodiment, X1 represents a hydrogen atom and X2 and X3, whether identical or different, represent a C1-C6 alkyl group, preferably a C1-C4 alkyl group, preferably a methyl group.When X1 and X3 or X2, or a carbon atom of the divalent hydrocarbon group of E and X3 or X2 are bonded together with the carbon atoms of the epoxide group to form a C4-C8 carbocycle or a heterocycle having 5 to 8 members, the C4-C8 carbocycle or heterocycle having 5 to 8 members is advantageously saturated, and preferably is a C4-C8 carbocycle, advantageously a cyclopentane, a cyclohexane or a cycloheptane, more preferably a cyclohexane. Advantageously, X4 represents a C1-C12 alkyl, a phenyl, a cyclohexyl or a phenyl-(C1-C6)alkyl, preferably a C1-C6 alkyl, a phenyl or a benzyl, preferably a C1-C4 alkyl, more preferably a methyl or an ethyl.Advantageously, the compound according to the invention is a compound of formula (I) in which: - R1 and R3 are identical and designate a group of formula (II) in which: - E represents a C1-C12 alkyl, preferably C1-C4, optionally comprising one or more heteroatoms; - X1, X2 and X3, identical or different, represent a hydrogen atom or a C1-C6 alkyl; - the symbol (*) represents the point of attachment of group (II) to the rest of the compound of formula (I); - R5 represents -O-X4, with X4 representing a C1-C18 alkyl, preferably a C1-C6 alkyl, preferably a C1-C4 alkyl, more preferably a methyl or a. éthyle ; - R2, R4, and R6, whether identical or different, represent a hydrogen atom or a C1-C12 alkyl group; preferably, R2, R4, and R6 each represent a hydrogen atom. Even more advantageously, the compound of formula (I) is chosen from the group formed, ,and their mixtures. Process for preparing a compound of formula (I) In a first embodiment, the process for preparing a compound of formula (I) according to the invention comprises a step b) of bringing the following compounds into contact: - a compound of the following formula (I-2): in which: - R1' and R3' of formula (I-2) denote an -OH group; - R5 represents -O-X4 with X4 representing a C1-C18 alkyl, a C6-C14 aryl, a C3-C7 cycloalkyl or a (C6-C14)aryl-(C1-C6)alkyl; and - R2, R4 and R6 are identical to those of formula (I); - a compound of the following formula (II-1): in which: - Y2 represents a function capable of reacting with an -OH group to form an ether bond, and -E, X1, X2 and X3 are identical to those of formula (II). In this embodiment, the compound of formula (I-2) can be prepared by an ether bond formation reaction to obtain the substituent R5 from the compound of formula (I-1) defined below. Thus, the compound of formula (I) can be prepared by a preparation process comprising two successive ether bond formation reactions. The preparation process described below is suitable for preparing all kinds of compounds of formula (I). The compound of formula (I) can therefore be prepared in two steps from the compound of formula (I-1): in which: - R1', R3', R5' of formula (I-1), denote an -OH group, and - R2, R4 and R6 are identical to those of formula (I). The compound of formula (I-1) is preferably phloroglucinol.The first step (a) is a step of bringing the compound of formula (I-1) into contact with a compound Y1-X4, in which -Y1 represents a functional group capable of reacting with an -OH group to form an ether bond, and -X4 is as defined previously. The functional groups Y1 are well known to those skilled in the art. For example, Y1 can represent an -OH group or a halogen atom, the halogen preferably being a bromine or chlorine atom. Preferably, Y1 represents an -OH group. The conditions of this step (a) are a transposition of the usual conditions for ether bond formation reactions. This reaction can be carried out in an organic solvent, for example, a polar and aprotic solvent such as tetrahydrofuran, or a polar solvent such as toluene. When Y1 represents an -OH group, the compound Y1-X4 can also act as the solvent for the reaction, particularly when X4 represents a C1-C alkyl group. 18Advantageously, when X4 represents a C1-C6 alkyl group, Y1-X4 acts as the solvent; preferably when X4 represents a C1-C4 alkyl group, it acts as the solvent, more preferably a methyl or ethyl group. Y1-X4 is therefore preferentially methanol or ethanol. The reaction can be carried out under acidic conditions, for example in the presence of a strong Brønsted acid such as sulfuric acid, and preferably at a temperature ranging from 0 to 90 °C, preferably from 20 °C to 70 °C, typically around 50 °C. The reaction time can range from 1 hour to 40 hours. Step a) can therefore be represented by the following scheme. Step a) therefore leads to obtaining a compound of formula (I-2) in which: - R1' and R3' are identical to those of formula (I-1), - R5 represents -O-X4 with X4 representing a C1-C18 alkyl, a C6-C14 aryl, a C3-C7 cycloalkyl or a (C6-C14)aryl-(C1-C6)alkyl, and - R2, R4 and R6 are identical to those of formula (I). Step b), which is the second step when step a) is implemented, is a step of contacting the compound of formula (I-2) as defined above with a compound of formula (II-1) as follows: as defined previously. This step therefore leads to obtaining a compound of formula (I) according to the invention. The functional groups Y2 are well known to those skilled in the art. For example, Y2 can represent an -OH group or a halogen atom, the halogen preferably being a bromine or chlorine atom. Preferably, Y2 represents a chlorine or bromine atom. The conditions of this step b) are a transposition of the usual conditions for ether bond formation reactions, which are not necessarily identical to those of step a). This reaction can be carried out in an organic solvent, for example, a polar and aprotic solvent such as tetrahydrofuran (THF), dimethylformamide (DMF), or acetonitrile. The compound of formula (II-1) can also act as the solvent when it is in liquid form under the reaction conditions.Preferably, when E represents a -CH2- group, X1, X2, and X3 represent a hydrogen atom, and Y2 represents a chlorine or bromine atom, then the compound of formula (II-1) also acts as a solvent. The reaction can be carried out at a temperature ranging from 20 to 150 °C, preferably from 50 °C to 120 °C, typically about 90 °C. The reaction time can range from 15 minutes to 10 hours, typically about 2 hours. According to a second embodiment, the compound of formula (I) can be prepared by a process comprising an epoxidation step of a compound of formula (I-3) defined below; this step thus yields a compound of formula (I). This epoxidation step is preferably preceded by an ether bond formation step to obtain the ether functions of the groups of formula (II); it yields the compound of formula (I-3).This step is advantageously preceded by an ether bond formation step in order to form the ether bond of the R5 group to obtain compound (I-1). The compound of formula (I) can be prepared in three steps from the compound of formula. (I-1) : as defined previously. The first step a') is identical to step a) as defined previously. Step a') yields a compound of formula (I-2) with the following formula: Step b'), which is the second step when step a' is implemented, is a step of contacting the compound of formula (I-2) with a compound according to the following formula (II-2): in which: - Y2 represents a functional group capable of reacting with an -OH group to form an ether bond as defined previously, and - E, X1, X2, and X3 are as defined previously. The conditions of this step b') are a transposition of the usual conditions for ether bond formation reactions. This reaction can be carried out in an organic solvent, for example, a polar and aprotic solvent such as tetrahydrofuran, or a polar solvent such as toluene. Step b') can be carried out with a compound molar ratio of formula (I-2):compound according to formula (II-2) ranging from 1.9 to 5, preferably ranging from 2 to 4, typically ranging from 2.1 to 2.4.Step b') can therefore be represented by the following diagram. Step a) therefore leads to obtaining a compound of formula (I-3) in which: - R1'' and R3'' are identical and designate a group according to the following formula (II-3): in which: - E, X1, X2, and X3 are as defined previously; - the symbol (*) represents the point of attachment of the group of formula (II-3) to the rest of the compound of formula (I-3); - R2, R4, R5, and R6 are identical to those of formula (I). Step c'), which is the third step when steps a') and b') are carried out, is a step of contacting the compound of formula (I-3) as defined previously with an epoxidizing agent. In the context of the present invention, the epoxidizing agent is a compound or a mixture of compounds that allows the transformation of the C=C double bond of the compound of formula (I-3) into an epoxide function. This step therefore leads to obtaining a compound of formula (I) as defined previously. Epoxidizing agents are numerous and known to those skilled in the art. For example,The epoxidizing agent is metachloroperbenzoic acid (MCPBA). The conditions of this epoxidation step c') are a transposition of the usual conditions for epoxidation reactions. This reaction can be carried out in an organic solvent, preferably polar and aprotic, such as dichloromethane, and preferably at room temperature. The duration of the reaction can range from 1 hour to 50 hours. In all embodiments, the compound (I) thus obtained can be separated from the reaction mixture by methods well known to those skilled in the art, such as extraction, evaporation of the solvent, or precipitation and filtration. The same applies to the compound of formula (I-2) obtained at the end of step a) or a') and to the compound (I-3) obtained at the end of step b'). The compounds can also be purified, if necessary, by techniques well known to those skilled in the art, such as recrystallization if the compound is crystalline.by distillation, by silica gel column chromatography, or by high-performance liquid chromatography (HPLC). Use of a compound of formula (I) and process for preparing thermosetting materials. Compounds of formula (I) are particularly interesting precursors for the preparation of polymer materials, and especially thermosetting polymer materials. A thermosetting material is a polymer material obtained by a polymerization step that makes the material irreversibly rigid. This hardening is due to significant cross-linking between the polymer chains. Cross-linking is a chemical reaction that creates covalent chemical bonds between polymer chains that are not initially linked by covalent bonds. This reaction is generally initiated by heat, pressure, or a change in pH.radiation and most often requires a crosslinking agent. The crosslinking of linear or branched polymer chains is accompanied by an increase in the molecular dimensions of the chains, particularly their molar masses, and leads to the formation of a network of crosslinked polymers. Thermosetting polymers have very good mechanical properties, particularly strength, and can also be used as adhesives. Thus, another object of the invention relates to the use of a compound of formula (I) for the preparation of a thermosetting material. Also,Another object of the invention relates to a process for preparing a thermosetting material comprising a polymerization step of a compound of formula (I). This polymerization can be carried out with at least one monomer M different from the compound of formula (I). This monomer M has at least two reactive functions that can react with the epoxide functions present in the compound of formula (I). These functions are well known to those skilled in the art. For example, amine, amide, carboxylic acid, and derivative functions such as acid anhydrides, isocyanates, polymer mercaptans, and phenols can be cited. The monomer M can preferably be chosen from diamines such as urea and its derivatives, dicyandiamide, or aliphatic diamines with a cyclohexyl center such as isophorone diamine or those marketed under the names Priamine 1071 or Priamine 1075. The monomer M can be chosen from acid anhydrides, aromatic amines,Cycloaliphatic amines, primary aliphatic amines, and carboxylic acids. The following acid anhydrides may be cited: hexahydrophthalic anhydride, succinic anhydride, maleic anhydride, chlorendic anhydride, nadic anhydride, tetrachlorophthalic anhydride, pyromellitic dianhydride, 1,2,3,4-cyclopentaetetracarboxylic acid dianhydride, glutaric anhydride, phthalic anhydride, and aliphatic acid polyanhydrides such as polyazelaic polyanhydride or polysebatic polyanhydride. The following aromatic amines may be cited: 4,4'-aminodiphenylsulfone, also called DDS, 4,4'-methylene-bis(2,6-diethylaniline), 4,4'-(phenylenediisopropyl)-bis(2,6-dipropylaniline), 4,4'-methylenebis(2-isopropyl-6-methylaniline) also called M-MIPA, 4,4'-methylenebis(2,6-diethylaniline) also called M-DEA, 4,4'-methylenebis(3-chloro-2,6-diethylaniline) also called M-CDEA, 4,4'-(phenylenediisopropyl)-bis(2,6-dimethylaniline), 4,4'-(phenylenediisopropyl)-bis(2,6-diethylaniline), 4,4'-(phenylenediisopropyl)-bis(2,6-dipropylaniline), 4,4'-(phenylenediisopropyl)-bis(2,6-diisopropylaniline), 4,4'-(phenylenediisopropyl)-bis(2,6-dimethyl-3-chloroaniline), 4,4'-(phenylenediisopropyl)-bis(2,6-diethyl-3-chloroaniline), 4,4'-(phenylenediisopropyl)-bis(2,6-dipropyl-3-chloroaniline), 4,4'-(phenylenediisopropyl)-bis(2,6-dipropyl-3-chloroaniline), 3,3'-(phenylenediisopropyl)-bis(2,6-dimethylaniline), 3,3'-(phenylenediisopropyl)-bis(2,6-diethylaniline), 3,3'-(phenylenediisopropyl)-bis(2,6-dipropylaniline), 3,3'-(phenylenediisopropyl)-bis(2,6-dimethyl-3-chloroaniline), 3,3'-(phenylenediisopropyl)-bis(2,6-diethyl-3-chloroaniline), 3,3'-(phenylenediisopropyl)-bis(2,6-dipropyl-3-chloroaniline), 3,3'-(phenylenediisopropyl)-bis(2,6-diisopropylaniline), and 3,3'-(phenylenediisopropyl)-bis(2,6-Diisopropyl-3-chloroaniline). The following cycloaliphatic amines can be cited: 1,3-cyclohexanediamine, 1,4-cyclohexanediamine, 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, bis(aminomethyl)norbornane, 4,4'-diaminodicyclohexylmethane also known as PACM, 3,3'-dimethyl-4,4'-dicyclohexylmethane also known as MACM, isophorone diamine also known as IPDA, and menthane diamine. The primary aliphatic amines can be cited: ethylenediamine, diethylenetriamine, triethylenetetramine, piperazinoethylethylenediamine, aminoethyldiaminoethylpiperazine, aminoethylpiperazine, and aminoethylethanolamine. (AEEA marketed by DowChemical), polyetheramine-type amino monomers prepared from ethylene oxide, propylene oxide, or a mixture of ethylene oxide / propylene oxide (such as the Jeffamines series marketed by Huntsman), 4.7,10-trioxatridecan-l,13-diamine, polytetrahydrofuranamine (marketed by BASF), polyamidoamines, polyaminoimidazolines, unbranched or hyperbranched polyethyleneimines (PEI) and polyalkyleneamines. The following carboxylic acids may be cited: carboxylic acids comprising 2 to 40 carbon atoms, such as linear diacids (glutaric, adipic, pimelic, suberic, azelaic, sebacic, dodecanedioic and their higher mass homologues) as well as their mixtures, or fatty acid derivatives, trimers (oligomers of 3 identical or different monomers) and mixtures of dimers and trimers of fatty acids, in particular of vegetable origin. These compounds result from the oligomerization of unsaturated fatty acids such as: undecylenic, myristoleic, palmitoleic, oleic, linoleic, linolenic, ricinoleic, eicosenoic, and docosenoic acids, which are commonly found in pine, rapeseed, corn, sunflower, and soybean oils.Grape seed, flax, jojoba, as well as eicosapentaenoic and docosahexaenoic acids found in fish oils. Aromatic carboxylic acids with 2 to 40 carbon atoms, such as aromatic diacids like phthalic acid, trimellitic acid, terephthalic acid, or naphthalenedicarboxylic acid, can also be mentioned. This polymerization step of a compound of formula (I) can lead directly to a thermosetting material, or it can lead to a predominantly linear polymer chain that will subsequently require an additional crosslinking step to obtain the thermosetting material. Optionally, the preparation process includes an additional crosslinking step with a crosslinking agent, also called a curing agent. The compound of formula (I) is divalent,Indeed, it has two formula groups (II) and therefore two epoxide functions. When the monomer M is trivalent, the monomer M and the compound of formula (I) are introduced in a molar proportion (I):M ranging from 6:1 to 1:6, preferably ranging from 5:1 to 1:5, even more preferably from 4:1 to 1:4, typically about 3:1. When the monomer M is divalent, the monomer M and the compound of formula (I) are introduced in a molar proportion (I):M ranging from 6:1 to 1:6, preferably ranging from 4:1 to 1:4, even more preferably from 3:1 to 1:2, typically about 2:1. Advantageously, the monomer M and the compound of formula (I) are introduced in a molar proportion equivalent to the reactive functions of the monomer M as defined above: epoxide functions of the compound of formula (I) (abbreviated proportion in M, R :(I) R) ranging from 0.8:1 to 1:0.8, preferably from 0.9:1 to 1:0.9, typically about 1:1. The reaction can take place in an organic solvent, more preferably polar, in a mass quantity ranging from 0% to 1000% by mass of the mass of the monomers involved, preferably ranging from 5% to 500% by mass of the monomers involved, preferably still ranging from 10% to 50% by mass of the monomers involved. In the case where the solvent is a polar organic solvent, it is preferably aprotic, chosen by a person skilled in the art as enabling the solubilization of the monomer(s) and possibly the polymer produced, and with a sufficiently high boiling point to carry out the reaction under the required conditions, such as dimethyl sulfoxide, tetrahydrofuran, dichloromethane, acetone, acetonitrile, trifluorotoluene or diphenyl ether.When this solvent is miscible with water, the solvent may consist of a mixture of the aprotic solvent with water, for example, a dimethyl sulfoxide / water mixture. The polymerization reaction can be carried out at a temperature ranging from 20 °C to 220 °C, preferably from 40 °C to 200 °C, preferably from 50 °C to 160 °C or from 60 °C to 120 °C, more preferably from 70 °C to 100 °C, typically around 80 °C. The reaction time can range from 10 minutes to 4 hours, typically around 60 minutes. At the end of the process according to the invention, the polymer produced can be recovered in a known manner, stored if necessary, and possibly processed for subsequent uses by techniques known to those skilled in the art. The polymer thus obtained can exhibit a glass transition temperature (Tg) ranging from 0°C to 200°C, preferably from 20°C to 200°C.The glass transition temperature (Tg) can be measured by any method known to those skilled in the art, particularly the one described in the examples. Another object of the invention relates to a polymer obtainable by the polymerization step of a compound of formula (I) as defined above. Optionally, the polymer has undergone the additional crosslinking step as defined above. Those skilled in the art can determine the structure of the polymer obtained based on the nature of the monomers M, the compounds of formula (I), and optionally the crosslinking agents used. This polymer is preferably a thermosetting material. The polymer thus obtained can have a glass transition temperature (Tg) ranging from 0°C to 250°C, preferably from 20°C to 250°C, and preferably from 20°C to 200°C.Another object of the invention relates to the use of a compound of formula (I) as a precursor of polymeric materials, in particular thermosetting materials, or as an adhesive. It is understood that, when used as an adhesive, the compound of formula (I) must be brought into contact with a crosslinking agent to obtain the desired effect. The aforementioned features of the present invention, as well as others, will be better understood upon reading the following description of several illustrative and non-limiting embodiments of the invention. EXAMPLES The following examples illustrate particular embodiments of the invention without limiting its scope.The following abbreviations are used in the examples: - AHEW – amine hydrogen equivalent weight - d – diameter - DCM – dichloromethane - DMF – dimethylformamide - HMBC – heteronuclear multiple-bond correlation - HSQC – heteronuclear single quantum coherence - l – length - MCPBA – metachloroperbenzoic acid - TA – room temperature - TMBAC – trimethylbenzylammonium chloride - TMS – tetramethylsilane - THF – tetrahydrofuran - v / v – volume / volume 1. Materials and Methods 1.1. Characterization of Molecules Structural analysis and determination of the molar purities of the synthetic molecules are carried out by NMR analysis. Spectra are acquired on an "Avance 3400 MHz BRUKER" spectrometer equipped with a "BBFO-zgrad 5 mm broadband probe". The NMR experiment. 1Quantitative H uses a simple 30° pulse sequence and a 3-second repetition delay between each of the 64 acquisitions. Samples are solubilized in a deuterated solvent, deuterated chloroform (CDCl3), unless otherwise specified. The deuterated solvent is also used for the lock signal. For example, calibration is performed on the proton signal of deuterated CDCl3 at 7.20 ppm relative to a TMS reference at 0 ppm. The NMR spectrum 1 H coupled with 2D HSQC experiments 1 H / 13 C and HMBC 1 H / 13 These techniques allow for the structural determination of molecules. Molar quantifications are performed using the 1D NMR spectrum. 1 Quantitative H. The ERETIC quantification method consists of measuring the mass percentage of one or more species present in a sample by external calibration, using as a standard a reference tube of triphenylphosphate (TPP) at 48.5 mmol / L in acetone-d6. An NMR spectrum1 Quantitative H-scanning with a single 30° pulse is recorded with a D1 recycling delay of 62 seconds between each of the 16 scans. The sample to be analyzed is precisely weighed and dissolved in a precise volume of the appropriate deuterated solvent (approximately 10 mg / mL). A series of NMR spectra is then acquired. 1 A single 30° pulse H scan with the same number of scans (usually 8), the same RG, and different D1 values ​​(usually 5 / 10 / 15, or even 20s) is recorded and then superimposed to ensure the quantitative nature of the measurement. An NMR spectrum is then produced. 1H with a single 30° pulse is then recorded on the same tube using the adapted D1 (from the previous test) at 64 or 128 scans. The TPP signal is integrated onto the reference spectrum, which counts as 15 protons and is recorded as "Define as ERETIC reference". The most isolated and resolved signal(s) of each species identified in the sample spectrum are also integrated. Using the ERETIC (Calculate Concentration) module of Topspin, it is necessary to enter the precise volume of solvent used, the number of protons assigned to each of the integrated signals, and the molar mass of each species corresponding to the integrated signals. The concentration of the species in the sample is calculated directly by this module. This value is compared to the theoretical concentration (mmol / L) calculated using the sample weight, the solvent volume, and the molar masses of each species. 1.2. Chemical Compounds All compounds are from a commercial source (Sigma-Aldrich). 2. Synthesis of Compound A (2,2'-(((5-ethoxy-1,3-phenylene)bis(oxy))bis(methylene))bis(oxirane))) The synthesis of compound A is carried out in two steps starting from phloroglucinol. 2.1. Synthesis of compound A-1 (5-ethoxybenzene-1,3-diol) Under argon protection, a suspension of phloroglucinol (20.00 g; 159 mmol) in anhydrous ethanol (240 mL) is stirred at room temperature (20–22 °C) to obtain a pale yellow solution. Concentrated sulfuric acid (30 mL) is added dropwise over 20–25 minutes. The temperature of the mixture is gradually raised to 50–55 °C. Then, still under argon protection, the mixture is refluxed for 20 hours. The ethanol is then evaporated under vacuum (Tbain = 50 °C, 20 mbar), and the residue is carefully poured into distilled water (300 mL). The aqueous phase is extracted with ethyl acetate (3 × 120 mL). The collected organic phases are washed with distilled water (2x70 mL) and concentrated under reduced pressure (Tbain = 40°C, 25 mbar) to obtain an orange-brown oil.The product of interest is isolated by silica column chromatography (230-400 mesh, l = 40 cm, d = 4.5 cm) using a gradient of ethyl acetate and petroleum ether (v / v, 1:3 to 1:2 to 1:1). After evaporation (Tbain = 40 °C, 8 mbar), a yellow oil is obtained, which partially crystallizes upon prolonged storage. For further purification, the crude oil is mixed with distilled water (30 mL) and vigorously shaken at room temperature for 10-15 minutes. The resulting precipitate is filtered, washed with distilled water (3 x 10 mL), and air-dried. An off-white solid (7.860 g; 51 mmol) is obtained. Yield: 32%, melting point: 84-85 °C, purity: 93% (1H NMR). NMR attribution (CDCl3):. Table 1 №δ 1H (ppm) δ 13C (ppm)1 5.92 95.8 2 / 157,3 3 5.92 94.9 4 / 160,8 5 3.81 63.76 1.25 14.62.2. Synthesis of compound A TMBAC (1.368 g, 7.33 mmol) is added to a mixture of 5-ethoxybenzene-1,3-diol (compound A-1; 5.650 g, 36.6 mmol) and epichlorohydrin (102 g, 1099 mmol). The reaction mixture is heated to Tbain = 90 °C for 1 hour. An aqueous solution of NaOH (7.33 g NaOH in 29.32 g water) is then added, and the biphasic mixture is heated to Tbain = 90 °C for another hour. The aqueous phase is then separated, while the organic phase is washed with brine (30 mL) and then with distilled water (2 x 30 mL). After separation and concentration under reduced pressure (Tbain = 50 °C, 25 mbar), a yellow-orange oil is obtained. The target product is isolated by silica column chromatography (230-400 mesh, l = 27 cm, d = 4.5 cm) by eluating with a mixture of ethyl acetate and petroleum ether (v / v, 1:1) without gradient.The fractions of interest are collected and concentrated under reduced pressure (Tbain = 40 °C, 5 mbar) to produce a transparent oil (4.606 g, 17.30 mmol). Yield: 47%, purity: 92% (NMR-). 1 H). NMR attribution (CDCl3): Table 2 №δ 1H (ppm) δ 13C (ppm)1 1.31 14.72 3.90 63.5 3 / 160,7 4 6.04 94.4 5 / 160,2 6.04 94.07 3.81 and 4.11 68.73. Synthesis of the compound (2,2'-(((5-methoxy-1,3-phenylene)bis(oxy))bis(methylene))bis(oxirane))) The synthesis of compound A is carried out in two steps starting from phloroglucinol. 3.1. Synthesis of compound B-1 (5-methoxybenzene-1,3-diol) Product (B-1) (5-methoxybenzene-1,3-diol, CAS 2174-64-3) is commercially available or can be synthesized from phloroglucinol according to the procedure described in the article AngewandteChemie, International Edition 2014, 53, 7832-7837. 3.2. Synthesis of compound B TMBAC (1.106 g, 5.92 mmol) is added to a mixture of 5-methoxybenzene-1,3-diol (compound B-1; 4.15 g, 29.6 mmol) and epichlorohydrin (82 g, 888 mmol). The reaction mixture is heated at Tbain = 90 °C for 1 hour. An aqueous solution of NaOH (5.92 g NaOH in 29.6 g water) is then added, and the resulting biphasic mixture is heated at Tbain = 90 °C for another hour. The aqueous phase is then separated, while the organic phase is washed with brine (30 mL) and then with distilled water (2 x 30 mL). After separation and concentration under reduced pressure (Tbain = 50 °C, 5 mbar), a yellow-orange oil is obtained. The target product is isolated by silica column chromatography (230-400 mesh, length 22 cm, diameter 4.5 cm) eluent with a mixture of ethyl acetate and petroleum ether (v / v, 2:1) without gradient.The fractions of interest are collected and concentrated under reduced pressure (Tbain = 40 °C, 5 mbar) to produce a slightly yellowish oil. After 48 hours at room temperature, this oil partially crystallizes. A mixture of ethyl acetate and petroleum ether (v / v, 1:1, 10 mL, at 0 °C) is then added, and the resulting suspension is stirred at 1–3 °C for 10–12 minutes. The precipitate is filtered, washed with a mixture of ethyl acetate and petroleum ether (v / v, 1:1, 2 x 5 mL, at 0 °C), and air-dried. A white solid (0.467 g, 1.85 mmol) is obtained. Yield: 6%, melting point: 61-62 °C, purity: 96% (1H NMR). NMR assignment (CDCl3): Table 3 №δ 1H (ppm) δ 13C (ppm)1 3.70 55.4. 2 / 161,5 3 6.06 94.1 4 / 160,3 5 6.06 94.16 3.84 and 4.12 68.87 3.24-3.30 50.08 2.68 and 2.83 44.74. Synthesis of compound C [3,3'-(((5-ethoxy-1,3-phenylene)bis(oxy))bis(methylene))bis(2,2-dimethyloxirane)] The synthesis of compound C is carried out in two steps starting from phloroglucinol and compound (C-2) with the following formula: Compound (C-2) can be prepared in two steps from isoprene. 4.1. Synthesis of compound C-1 (1-bromo-3-methylbut-2-ene) Product C-1, 1-bromo-3-methylbut-2-ene, CAS [870-63-3], is commercially available or can be synthesized from isoprene according to the procedure described in the article *Journal of the Chemical Society*, Perkin Transactions I, 1985, 2307-2326. 4.2. Synthesis of compound C-2 (3-(bromomethyl)-2,2-dimethyloxirane) The compound C-2,3-(bromomethyl)-2,2-dimethyloxirane can be obtained according to the procedure described in the article Organic Process Research & Development 2005, 9, 278-287. NMR attribution (CDCl3): Table 4 №δ 1H (ppm) δ 13C (ppm)1 3.13 and 3.37 29.62 2.94 62.0 3 / 60,1 4 1.17 and 1.21 18.0 and 24.34.3. Synthesis of compound A-1 (5-ethoxybenzene-1,3-diol) The synthesis of compound A-1 from phloroglucinol is described in section 2.1 of the examples. 4.4. Synthesis of Compound C A solution of 5-ethoxybenzene-1,3-diol (compound A-1; 0.848 g, 5.50 mmol) and 3-(bromomethyl)-2,2-dimethyloxirane (compound C-2; 2.179 g, 13.20 mmol) in anhydrous acetonitrile (30 mL) is degassed by bubbling with argon for 8–10 minutes. Potassium carbonate (2.281 g, 16.50 mmol) is then added in a portion. Still under argon protection, the reaction mixture is refluxed for 8 hours. Once complete, inorganic salts are filtered and washed with acetone (2 × 10 mL). The permeate is concentrated under reduced pressure (Tbain = 40 °C, 10 mbar) to yield a brown oil. The target product is isolated by silica column chromatography (230-400 mesh, l = 20 cm, d = 1.5 cm) by eluting with a gradient-free mixture of ethyl acetate and petroleum ether (v / v, 1:3).The fractions of interest are collected and concentrated under reduced pressure (Tbain = 40 °C, 5 mbar) to obtain a colorless and transparent oil (0.671 g, 2.08 mmol). Yield: 38%, mass purity: greater than 90% (1H NMR). NMR assignment (CDCl3):. Table 5 №δ 1H (ppm) δ 13C (ppm)1 1.33 14.72 3.93 63.5 3 / 160,8 4 6.07 94.2 5 / 160,4 6 6.07 94.57 3.97 and 4.01 67.08 3.06 60.5 9 / 58,2 10 1.28 and 1.33 18.9 and 24.65. Synthesis of compound D (2,2'-(((5-ethoxy-1,3-phenylene)bis(oxy))bis(ethane-2,1-diyl))bis(oxirane)) The synthesis of compound D is carried out in two steps starting from phloroglucinol and compound (D-1) with the following formula: Compound (D-1) can be prepared in one step from 4-bromo-1-butene. 5.1. Synthesis of compound D-1 (1-bromo-3-methylbut-2-ene) Compound D-1, 2-(2-bromoethyl)oxirane, can be obtained according to the procedure described in the article Organic & Biomolecular Chemistry 2021, 19, 8578-8585. NMR attribution (CDCl3): Table 6 δ1H (ppm) δ13C (ppm) 3.44 28.72 1.98 and 2.08 35.33 3.02 16.74 2.50 and 2.76 50.4 5.2. Synthesis of compound A-1 (5-ethoxybenzene-1,3-diol) The synthesis of compound A-1 from phloroglucinol is described in section 2.1 of the examples. 5.3. Synthesis of compound D A solution of 5-ethoxybenzene-1,3-diol (compound A-1; 1.00 g, 6.49 mmol) and 2-(2-bromoethyl)oxirane (compound D-1; 2.35 g, 15.58 mmol) in anhydrous acetonitrile (35 mL) is degassed by bubbling with argon for 8–10 minutes. Potassium carbonate (2.69 g, 19.47 mmol) is then added in a single portion. Still under argon protection, the reaction mixture is refluxed for 8 hours. After reflux, inorganic salts are filtered and washed with acetone (2 × 12 mL). The permeate is concentrated under reduced pressure (Tbain = 40 °C, 10 mbar) to yield a brown oil. The target product is isolated by silica column chromatography (230-400 mesh, 23 cm long, 1.5 cm diameter) using a gradient-free mixture of ethyl acetate and petroleum ether (v / v, 1:3). The fractions of interest are collected and concentrated under reduced pressure (Tbain = 40 °C, 5 mbar) to obtain a colorless and transparent oil (0.82 g, 2.79 mmol).Yield: 43%, mass purity: greater than 89% (1H NMR). NMR attribution (CDCl3):. Table 7 №δ 1H (ppm) δ 13C (ppm)1 1.32 14.72 3.91 63.5 3 / 160,6 4 6.05 94.1 5 / 160,3 6 6.05 94.37 4.03 64.68 1.94 and 2.10 32.49 3.09-3.15 49.610 2.45 and 2.70 47.06. Synthesis of compound E ((1,3,5-tris(2-(2-oxiran-2-yl)ethoxy)benzene) The synthesis of compound E is carried out in one step from phloroglucinol and compound (D-1). A solution of 2-(2-bromoethyl)oxirane (compound D-1; 0.838 g; 5.55 mmol) in anhydrous DMF (10 mL) is stirred at room temperature by bubbling with argon for 8–10 minutes. Phloroglucinol (0.2 g; 1.59 mmol) is added in one portion, and the reaction mixture is cooled to 0°C. Under argon protection, NaH (60% mineral oil dispersion; 0.213 g; 8.88 mmol) is added in several portions over 15 minutes. The resulting medium is stirred at 0°C for 30 minutes and at 80°C for an additional 5 hours. Once complete, the reaction mixture is mixed with distilled water (100 mL) and extracted with ethyl acetate (2 × 40 mL). The collected organic phases are concentrated under reduced pressure (T bain(= 33°C, 5 mbar) to produce a yellow-orange oil. The target product is isolated by silica column chromatography (l = 25 cm, d = 2 cm) using a mixture of DCM and ethyl acetate (5:1, v / v). The fractions of interest are combined and evaporated again under reduced pressure (Tbain = 30°C, 5 mbar). A clear oil (0.065 g; 0.19 mmol) is obtained. Yield: 12%, purity: 93% (NMR- 1 H). NMR attribution (CDCl3): Table 8 №δ 1H (ppm) δ 13C (ppm)1 2.53 and 2.78 46.92 3.09 49.53 1.92 and 2.08 32.24 4.03 64.5 5 / 160.7 6 6.08 94.27. Synthesis of compound F (1,3,5-tris((3-methyloxiran-2-yl)methoxy)benzene) The synthesis of compound F is carried out in two steps starting from phloroglucinol and compound (F-1) with the following formula: Compound (F-1) can be prepared in one step from 4-bromo-1-butene. 7.1. Synthesis of compound F-1 (2-bromomethyl)-3-methyloxirane Compound F-1, (2-bromomethyl)-3-methyloxirane, can be obtained, for example, according to the procedure described in the article Tetrahedron Letters 2003, 44, 3075-3080. NMR attribution (CDCl3): Table 9 δ1H (ppm) δ13C (ppm) 3.24 and 3.34 32.42 2.92 58.23 2.87 56.64 1.28 17.37.2. Synthesis of compound F A solution of phloroglucinol (1.01 g, 8.0 mmol) and 2-(bromomethyl)-3-methyloxirane (compound F-1; 4.59 g, 30.4 mmol) in anhydrous acetonitrile (40 mL) is degassed by bubbling argon for 10 minutes. Then, potassium carbonate (4.49 g, 32.5 mmol) is added in a single portion. Still under argon protection, the reaction mixture is refluxed for 12 hours. Once this is complete, inorganic salts are filtered and washed with acetone (2 x 20 mL). The permeate is concentrated under reduced pressure (T bain= 40°C, 5 mbar) to produce an orange-brown oil. The target product is isolated by silica column chromatography (230-400 mesh, 25 cm length, 1.5 cm diameter) by eluting with a gradient-free mixture of ethyl acetate and petroleum ether (v / v, 1:3). The fractions of interest are collected and concentrated under reduced pressure (T bain = 40°C, 5 mbar) to obtain a colorless and transparent oil (0.73 g, 2.17 mmol). Yield: 27%, purity: greater than 91% (1H NMR). NMR attribution (CDCl3): Table 10 №δ 1H (ppm) δ 13C (ppm)1 1.26 17.22 2.87 55.03 2.95 57.34 3.91 and 4.05 67.2 5 / 160.56.07 94.48. Evaluation of Compound (A) Properties. The properties of compound (A) with respect to DGEBA were evaluated in thermosetting materials. Different amine derivatives (crosslinking agents) were combined with this new monomer to study its thermal properties in formulations and compare them to DGEBA-based formulations: • Priamine 1071 (pf < -30 °C, AHEW = 140 g / eq), • DICY (dicyandiamide) (pf = 208-211 °C, AHEW = 21 g / eq), • IPDA (isophorone diamine) (pf = 10 °C, AHEW = 42.575 g / eq). The protocol for evaluating thermal properties in formulation was carried out as follows. The monomer was weighed with the corresponding diamine (1 equivalent relative to the reactive functions). The mixture was dissolved in a DMSO:water mixture (% mass = 74:26) at a mass concentration between 10 and 12%. The DMSO was added to the mixture followed by the water.After homogenization, the mixture was then placed in a vacuum oven (5 mbars) with a slight flow of nitrogen at 120 °C for 60 to 100 minutes (preheating step). A piece of the material, obtained after preheating, was taken to continue the second part of the reaction in the DSC (aluminum crucible with T. réaction < T décomposition ), under helium at 40 mL / min at 80 or 210 °C for 60 minutes. The glass transition temperature (Tg) of the resulting material is then measured by DSC, under helium at 40 mL / min, according to the méthode :1. Cooling from 25 °C to -150 °C at -50 °C / min, 2. Isothermal at -150 °C for 18 min, 3. Heating from -150 °C to +250 °C at 50 °C / min, 4. Isothermal at -150 °C for 18 min, 5. Heating from -150 °C to +250 °C at 50 °C / min. The Tg was measured on ramp #5. Several tests were carried out by varying the monomer used, the crosslinking agent (the diamine) used, and certain reaction conditions. These tests are summarized in the table below. Table 11 E ssai 1 2 3 4 5 6 Monomer Compound (A) according to the invention DGEBAPriamine Priamine Diamine DICY IPDA DICY IPDA1071 1071 molar equivalent molecule 1:2 1:2 diamine: molar equivalent monomer function 1:1 1:1 (NH:epoxide) Dispersion solvents D MSO:Eau = 74:26 (% mass:% mass) Mass of reactants (%) 12.6 9.8 10.4 12 12 12 Preheating time 1 00 60 (min) Temperature 1 20 120 Preheating (°C) Reaction time (min) 60 60 Reaction temperature 2 00 210(°C) Tg (°C) 23 125 98 24 140 100 The glass transition temperature of materials prepared from compound (A) compared to those prepared from DGEBA is similar, regardless of the crosslinking agent (Priamine 1071, DICY, and IPDA). These results demonstrate that the use of the monomers according to the invention makes it possible to obtain thermosetting materials with properties equivalent to those obtained with a reference monomer such as DGEBA, without the drawback of being derived from bisphenol A, and thus exhibiting improved HSE properties for the precursor of compound (A). The variety of glass transition temperatures obtained makes it possible to consider the use of thermosetting materials derived from these monomers in all kinds of application fields.

Claims

1. CLAIMS 1. Formula compound (I): in which: - R1 and R3, identical, denote a group of the following formula (II): in which -E represents a single bond or a C1-C12 hydrocarbon divalent group possibly comprising one or more heteroatoms; - X1, X2, and X3, identical or different, represent a hydrogen atom, a C1-C6 alkyl, or a C6-C14 aryl, and / or -X1 and X3 or X2, or a carbon atom from the hydrocarbon divalent group of E and X3 or X2, can be bonded together with the carbon atoms of the epoxy group to form a C4-C8 carbocycle or a heterocycle having 5 to 8 members; - the symbol (*) represents the point of attachment of group (II) to the rest of the compound of formula (I); - R5 represents -O-X4, with X4 representing a C1-C18 alkyl, a C6-C14 aryl, a C3-C7 cycloalkyl, or a (C6-C14)aryl-(C1-C6)alkyl ;- R2, R4 and R6, identical or different, represent a hydrogen atom or an alkyl in C1-C24.2.A compound according to claim 1, characterized in that R2, R4 and R6, identical or different, represent a hydrogen atom or a C1-C12 alkyl, preferably a hydrogen atom or a C1-C6 alkyl, preferably a hydrogen atom or a C1-C4 alkyl, more preferably a hydrogen atom.

3. A compound according to claim 1 or 2, characterized in that E represents a C1-C12 hydrocarbon divalent group, in particular C1-C10, in particular C1-C8, preferably C1-C6, preferably C1-C4, typically C1 or C2, optionally comprising one or more heteroatoms.

4. A compound according to any one of claims 1 to 3, characterized in that X4 represents a C1-C12 alkyl, a phenyl, a cyclohexyl or a phenyl-(C1-C6)alkyl, preferably a C1-C6 alkyl, a phenyl or a benzyl, preferably a C1-C4 alkyl, more preferably a methyl or an ethyl. 5.A compound according to any one of claims 1 to 4, characterized in that X1, X2 and X3, identical or different, represent a hydrogen atom or a C1-C6 alkyl, preferably X1 represents a hydrogen atom and X2 and X3, identical or different, represent a hydrogen atom or a C1-C6 alkyl, such as a methyl.

6. A compound according to any one of claims 1 to 5, selected from the group consisting of . , and their mixtures.

7. A process for preparing a compound of formula (I) according to any one of claims 1 to 6, comprising a step b) of contacting the following compounds: - a compound of the following formula (I-2): in which: - R1' and R3' of formula (I-2) denote an -OH group; - R5 represents -O-X4, with X4 representing a C1-C18 alkyl, a C6-C14 aryl, a C3-C7 cycloalkyl, or a (C6-C14)aryl-(C1-C6)alkyl; and - R2, R4, and R6, whether identical or different, represent a hydrogen atom or a C1-C24 alkyl; - a compound of the following formula (II-1): in which: - Y2 represents a function capable of reacting with an -OH group to form an ether bond; - E represents a single bond or C1-C12 hydrocarbon divalent group possibly comprising one or more heteroatoms; - X1, X2 and X3, identical or different, represent a hydrogen atom, a C1-C6 alkyl group or a C6-C14 aryl group, and / or -X1 and X3 or X2, or a carbon atom from the hydrocarbon divalent group of E and X3 or X2 can be bonded together, with the carbon atoms of the epoxide group, to form a C4 to C8 carbocycle or a heterocycle having 5 to 8 members. 8.A process according to claim 7, further comprising a step a) preceding step b), step a) being a step of bringing the following compounds into contact: - a compound of the following formula (I-1) in which: - R1', R3' and R5' denote an -OH group, and - R2, R4 and R6, identical or different, represent a hydrogen atom or a C1-C24 alkyl; - a compound Y1-X4 in which - Y1 represents a function capable of reacting with an -OH group to form an ether bond, and -X4 represents a C1-C18 alkyl, a C6-C14 aryl, a C3-C7 cycloalkyl or a (C6-C. 14)aryl-(C1-C6)alkyl.

9. Use of a compound of formula (I) according to any one of claims 1 to 6 as a precursor of polymeric materials, in particular thermosetting materials, or as an adhesive.

10. A process for preparing a thermosetting material comprising a polymerization step of a compound of formula (I) according to any one of claims 1 to 6, optionally the process further comprising a crosslinking step.

11. A thermosetting material obtainable by the process according to claim 10.

Images