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 production 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 degrade in performance during use, and whose end-of-life management can be facilitated.STATE OF THE TECHNOLOGY: Currently, among polyfunctional phenolic aromatic compounds, one can notably cite bisphenol A diglycidyl ether (BADGE), manufactured from bisphenol A (BPA) and epichlorohydrin (ECH). These two precursors are classified as Carcinogenic, Mutagenic, and Reprotoxic (CMR), namely category 2 reprotoxic and endocrine disruptor for BPA, and category 1B carcinogen for ECH. In recent years, several solutions have been implemented to develop compounds with a low environmental footprint and reduce their toxicity. Thus, in 2007, Solvay presented the EPICEROL® process for the bio-based production of ECH from glycerol. BPA, on the other hand, can be obtained by the reaction of phenol obtained by distillation of waste from the forestry industry and acetone produced by fermentation (SuperSap® prepolymer from Entropy Resins).However, the use of bio-based and renewable BPA and ECH does not change the hazard of these substances, which remain classified as CMR regardless of their origin. Therefore, it is preferable to improve their 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 hazard 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 epichlorohydrin, chlorinated residues contained in DGEBA-based thermosetting materials, and BPA resulting from the degradation of DGEBA-based thermosetting materials 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. DESCRIPTION OF THE INVENTION Thus, a first object of the invention is 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, 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 a group of formula (II) identical to R1 and R3 or -O-X4, with X4 representing a C1-C18 alkyl, a C2-C18 alkenyl, or a C6-C14 aryl. or a (C6-C14)aryl-(C1-C6)alkyl, preferably R5 represents a group of formula (II) identical to R1 and R3; -R2, R4 and R6, identical or different, represent a hydrogen atom or a C1-C24 alkyl.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 epoxidation of a compound of formula (I-2). in which: - R1'' and R3'' are identical and designate a group according to the following formula (II-2): 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 epoxide group to form a C4-C8 carbocycle or a heterocycle having 5 to 8 members; - the symbol (*) represents the point of attachment of the group of formula (II-2) to the rest of the compound of formula (I-2); - R5'' denotes a group identical to R1'' and R3'', or -O-X4, with X4 representing a C1-C18 alkyl, a C2-C18 alkenyl, a aryl at C6-C14 or a (C6-C14)aryl-(C1-C6)alkyl; - R2, R4 and R6, identical or different, represent a hydrogen atom or a C1-C24 alkyl, preferably a hydrogen atom or a C1-C12 alkyl,preferably a hydrogen atom or a C1-C6 alkyl group, preferably a hydrogen atom or a C1-C4 alkyl group, more preferably a hydrogen atom. 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 process according to the fourth object. DEFINITIONS In the present 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 (i.e., including the strict limits 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. By "alkyl group at C, x -C yFor the purposes of this invention, "x" refers to a monovalent, saturated, linear or branched hydrocarbon chain comprising x to y carbon atoms, where x and y are integers. Examples of C1-C6 alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isoamyl, neopentyl, and hexyl, preferably methyl, ethyl, propyl, or isopropyl. Examples of 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, for C1-C4 alkyl groups, we can cite methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, or tert-butyl. The expression "C1-Cj aryl" designates an aromatic hydrocarbon group containing from i to j carbon atoms, i and j being integers.This group may comprise one or more fused rings. Advantageously, this is 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 spiro-fused 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.For the purposes of this invention, the term "Cx-Cy alkenyl group" means a monovalent, linear or branched hydrocarbon chain comprising at least one double bond and x to y carbon atoms. Examples include ethenyl, propenyl, allyl, butenyl, pentenyl, and preferably allyl hexenyl groups. "Heteroatom" means any atom other than carbon or hydrogen, such as sulfur, nitrogen, or oxygen atoms. "Halogen atom" or "halogen" means, for the purposes of this invention, fluorine, chlorine, bromine, and iodine atoms. "Stereoisomer" means, for the purposes of this invention, 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 called enantiomers. Optical isomers that are not mirror images of each other are called 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. By "room temperature", for the purposes of the present invention, is understood to be a temperature generally ranging from 15°C to 40°C, preferably from 20°C to 30°C, in particular about 25°C.The compounds mentioned in the description may be of fossil origin or bio-based. In the latter case, they may be partially or totally derived from biomass or obtained from renewable raw materials derived from biomass. Similarly, the compounds mentioned may also come from the recycling of already used materials; that is, they may be partially or totally derived from 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" in this description means that the value in question may be 10% lower or higher, in particular 5%, and especially 1% higher, than the stated value.DETAILED DESCRIPTION OF THE INVENTION In the context of the present invention, the various embodiments presented in the description as a whole can be used alone or in combination with each other, without limitation of combination. 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, 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 a group of formula (II) identical to R1 and R3 or -O-X4, with X4 representing a C1-C12 alkyl. 18 , a C2-C alkenyl 18 , an aryl at C6-C 14 or a (C6-C 14)aryl-(C1-C6)alkyl, preferably R5, represents a group of formula (II) identical to R1 and R3; -R2, R4, and R6, identical or different, represent a hydrogen atom or a C1-C2 alkyl. Advantageously, R2, R4, and R6, identical or different, represent a hydrogen atom or a C1-C2 alkyl. 12E may represent a C1-C12 hydrocarbon divalent group, particularly at C1-C10, possibly comprising one or more heteroatoms, especially an alkyl group at C1-C12, particularly at C1-C10, possibly comprising one or more heteroatoms. When present, the heteroatoms are preferably chosen from S, O, and N, particularly from O and N, preferably O. Preferably, E does not comprise a heteroatom. E may represent a C1-C4 hydrocarbon divalent group, typically at C2, or a C5-C10 group, typically at C8, possibly comprising one or more heteroatoms. E may represent an alkyl in C1-C4, typically at C2, or in C5-C10, typically at C8, possibly comprising one or more heteroatoms.When present, heteroatoms are preferably chosen from S, O, and N, especially from O and N, preferably 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. E can advantageously represent a single bond or a C1-C12 alkyl, especially a C1-C10 alkyl. X1, X2, and X3, identical or different, can represent a hydrogen atom or a C1-C6 alkyl. Advantageously, X2 and X3 each represent a hydrogen atom. Advantageously, X1 represents a hydrogen atom or a C1-C6 alkyl, such as a methyl.Advantageously, X1, X2, and X3, whether identical or different, represent a hydrogen atom or a C1-C6 alkyl group, preferably a hydrogen atom or a methyl group, 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, preferably a saturated C4-C8 carbocycle, advantageously a cyclopentane, cyclohexane, or cycloheptane. When E represents a single bond, then X1, X2, and X3, whether identical or different, preferably represent a hydrogen atom or a C1-C6 alkyl group, preferably a hydrogen atom or a methyl group. Advantageously, at least one of X1, X2 and X3, preferably X1, represents a C1-C6 alkyl, more advantageously a methyl.When E represents a C1-C12 hydrocarbon divalent group possibly comprising one or more heteroatoms, then X1, X2 and X3, identical or different, preferably represent a hydrogen atom or a C1-C6 alkyl, preferably a hydrogen atom or a methyl, more preferably a hydrogen atom, and / or X1 and X3 or X2, or a carbon atom of the hydrocarbon divalent group of E and X3 or X2 may be linked together, with the carbon atoms of the epoxide group, to form a C4-C8 carbocycle or a heterocycle having 5 to 8 links, preferably a C4-C8 carbocycle.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 the heterocycle having 5 to 8 members is advantageously saturated, and preferably is a cyclopentane, a cyclohexane or a cycloheptane, more preferably a cyclohexane. Advantageously, X4 represents a C1-C12 alkyl, an allyl, a phenyl or (C6)aryl-(C1-C6)alkyl, preferably a C1-C6 alkyl, an allyl, 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, R3 and R5 of formula (I) are identical and designate a group according to formula (II) in which: - E represents a single bond or a C1-C12 alkyl optionally comprising one or more heteroatoms; - X1, X2 and X3, identical or different, represent a hydrogen atom or a C1-C6 alkyl, and / or - X1 and X3 or X2, or a carbon atom of the divalent hydrocarbon group of E and X3 or X2 can be linked together, with the carbon atoms of the epoxide group, to form a saturated C4-C8 carbocycle; -The symbol (*) represents the point of attachment of group (II) to the rest of the compound of formula (I);- R2, R4 and R6, identical or different, represent a hydrogen atom or a C1-C12 alkyl, preferably R2, R4 and R6 represent a hydrogen atom. Even more advantageously, the compound of formula (I) is chosen from the group formed. of , , , et their mixtures. Process for preparing a compound of formula (I) According to a first embodiment, the compound of formula (I) can be prepared by a process comprising an epoxidation step of a compound of formula (I-2) defined below; this step thus yields a compound of formula (I). This epoxidation step is preferably preceded by an esterification step allowing the ester functions of the groups of formula (II) to be obtained; it yields the compound of formula (I-2). The preparation process described below is suitable for preparing all kinds of compounds of formula (I). For example, this preparation process allows the preparation of compounds of formula (I) both when R5 represents -O-X4 and when R5 represents a group of formula (II) identical to R1 and R3. The compound of formula (I) can be prepared in two steps from the compound of formula (I-1) : in which: - R1' and R3' denote an -OH group, - R5' denotes an -OH or -O-X4 group, with X4 identical to that of formula (I), and - R2, R4 and R6 are identical to those of formula (I). The compound of formula (I-1) is preferably phloroglucinol or a compound of formula (I-1) in which R5' denotes -O-X4, with X4 identical to that of formula (I). The first step a) is a step of contacting the compound of formula (I-1) with a compound according to the following formula (II-1): in which: - Y represents a group halogen atom, with R arepresenting a C1-C6 alkyl group, and -E, X1, X2, and X3 are as defined previously. When Y represents a halogen atom, it preferably represents a chlorine atom. Preferably, Y represents an -OH group. The conditions for this esterification step a) are a transposition of the usual conditions for esterification or transesterification reactions, for example, the conditions for Steglich esterification in the presence of dicyclohexylcarbodiimide (DCC) or N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide (EDC) as the coupling agent and 4-dimethylaminopyridine (DMAP) as the catalyst. This reaction can be carried out in an organic solvent, preferably polar and aprotic, such as tetrahydrofuran, and preferably at a temperature ranging from 0 to 40 °C. The reaction time can range from 1 to 30 hours.When R5' designates an -OH group, step a) can be carried out with a compound molar ratio of formula (I-1):compound according to formula (II-1) ranging from 2.9 to 5, preferably from 3.1 to 4, typically about 3.6. When R5' designates -O-X4, step a) can be carried out with a compound molar ratio of formula (I-1):compound according to formula (II-1) ranging from 1.9 to 5, preferably from 2 to 4, typically from 2.1 to 2.4. 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 and designate a group according to the following formula (II-2): in which: - E, X1, X2, and X3 are as defined previously; - the symbol (*) represents the point of attachment of the group of formula (II-2) to the rest of the compound of formula (I-2); - R5'' denotes a group identical to R1'' and R3'', or -O-X4, with X4 identical to that of formula (I); - R2, R4, and R6 are identical to those of formula (I). Advantageously, R5'' denotes a group identical to R1'' and R3''. Step b), which is the second step when step a) is carried out, is a step of contacting the compound of formula (I-2) 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-2) into an epoxide function. This step therefore leads to obtaining a compound of formula (I) as defined previously. Epoxidation 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 b) 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 a second embodiment, the process for preparing a compound of formula (I) according to the invention comprises a step d) of contacting the following compounds: - a compound of formula (I-1) as defined above; - a compound of formula (III-1) as follows:. in which: - Y2 represents a functional group capable of reacting with an -OH group to form an ester bond, and -E, X1, X2, and X3 are identical to those of formula (II). Y2 advantageously represents a -C(O)-Y group, with Y as defined previously. In this embodiment, when R5' designates an -O-X4 group, the compound of formula (I-1) can be prepared by an ether bond-forming reaction to obtain the substitute R5 from a compound of formula (I-0) which corresponds to the compound of formula (I-1) in which R5' is replaced by an -OH group. Thus, according to this embodiment, the compound of formula (I) can be prepared by a preparation process comprising two successive reactions: a first ether bond-forming reaction and a second ester bond-forming reaction. The compound of formula (I) can therefore be prepared in two steps from the compound of formula (I-0). The compound with formula (I-0) is preferentially phloroglucinol.The first step (c) is a step involving contacting the compound of formula (I-0) 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 (c) 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, more preferably a methyl or ethyl group. Y1-X4 is therefore preferably 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 about 50 °C. The reaction time can range from 1 hour to 40 hours. Step d), which is the second step when step c), is a step of contacting the compound of formula (I-1) as defined above with a compound of formula (III-1) as follows: as defined previously. This step therefore leads to obtaining a compound of formula (I) according to the invention. The conditions of this step d) are such as those defined for step a). The compound (I) thus obtained can be separated from the reaction medium by methods well known to those skilled in the art, such as, for example, by extraction, evaporation of the solvent, or by precipitation and filtration. The same applies to the compound of formula (I-2) obtained at the end of step a) or to the compound of formula (II) obtained at the end of step c) when it is carried out. The compounds can also be purified if necessary by techniques well known to those skilled in the art, such as by recrystallization if the compound is crystalline, by distillation,by silica gel column chromatography or 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 polymeric materials, especially thermosetting polymeric materials. A thermosetting material is a polymeric 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, and phenols may be cited. The monomer M may preferably be chosen from among diamines such as urea and its derivatives or aliphatic diamines with a cyclohexyl center such as those marketed under the names Priamine 1071 or Priamine 1075. The monomer M may be chosen from among 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-dipropyl-aniline), 4,4'-methylene-bis(2-isopropyl-6-methyl-aniline) also called M-MIPA, 4,4'-methylene-bis(2,6-diethyl-aniline) also called M-DEA, 4,4'-methylene-bis(3-chloro-2,6-diethyl-aniline) also called M-CDEA, 4,4'-(phenylene-diisopropyl)-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 called PACM, 3,3'-dimethyl-4,4'-dicyclohexylmethane also called MACM, isophorone diamine also called IPDA, and menthane diamine. The primary aliphatic amines can be cited: ethylenediamine, diethylenetriamine, triethylenetetramine, piperazinoethylethylenediamine, aminoethyldiaminoethylpiperazine, aminoethylpiperazinoethylethylenediamine, 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, and jojoba oils, as well as eicosapentaenoic and docosahexaenoic acids found in fish oils, can be used. 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. When the compound of formula (I) is divalent, that is, when this compound has two groups of formula (II) and therefore two epoxide functions, then the preparation process preferably includes an additional crosslinking step with a crosslinking agent.also called a hardening agent. When the compound of formula (I) is trivalent, that is, when this compound has three groups of formula (II) and therefore three epoxide functions, then crosslinking can occur during polymerization with the monomer M. The thermosetting material can thus be obtained in a single polymerization step, and it is the monomer M that also acts as the crosslinking agent in such a case. When the monomer M is trivalent and the compound of formula (I) is divalent, the monomer M and the compound of formula (I) are introduced in a molar proportion (I): ranging from 6:1 to 1:6, preferably 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 and the compound of formula (I) is divalent, the monomer M and the compound of formula (I) are introduced in a molar proportion (I): Mallant 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. When the monomer M is divalent and the compound of formula (I) is trivalent, the monomer M and the compound of formula (I) are introduced in a molar proportion (I): ranging from 6:1 to 1:6, preferably from 2:1 to 1:2, even more preferably from 1.5:1 to 1:1.3, typically about 1.3:1. When the monomer M is trivalent and the compound of formula (I) is trivalent, the monomer M and the compound of formula (I) are introduced in a molar proportion (I): ranging from 6:1 to 1:6, preferably 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 40 °C to 200 °C, preferably from 50 °C to 160 °C, preferably from 60 °C to 120 °C, more preferably from 70 °C to 100 °C, typically about 80 °C. The reaction time can range from 10 minutes to 4 hours, typically about 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 10 °C to 50 °C, preferably from 20 °C to 35 °C. The Tg can be measured by any method known to those skilled in the art, in particular that 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 advantageously has a glass transition temperature (Tg) ranging from 0°C to 200°C, preferably from 10°C to 200°C, preferably from 0°C to 50°C, typically from 20°C to 35°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 - DCC – N,N'-dicyclohexylcarbodiimide - DMAP – 4-dimethylaminopyridine - DMF – dimethylformamide - DMSO – dimethyl sulfoxide - DSC – Differential Scanning Calorimetry - EDC – N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride - HMBC – heteronuclear multiple-bond correlation - HSQC – heteronuclear single quantum coherence - l – length - MCPBA – metachloroperbenzoic acid - TA – room temperature - 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. The spectra are acquired on an "Avance 3400 MHz BRUKER" spectrometer equipped with a "broadband BBFO-zgrad 5 mm" 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 on 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 of the 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 of the species. 100 with 1.2. Chemical Compounds All compounds are from commercial sources (Sigma-Aldrich and BLD Pharmatech). 2. Synthesis of compound A (benzene-1,3,5-triyl tris(3-(oxiran-2-yl)propanoate) The synthesis of compound A is carried out in two steps starting from phloroglucinol. 2.1. Synthesis of compound A-1 Under argon protection, a solution of phloroglucinol (3.00 g; 23.8 mmol) in anhydrous THF (150 mL) is cooled slightly to 10 °C. Then, the following are added in the specified order: 4-pentenoic acid (8.57 g; 86.0 mmol), DCC (15.46 g; 74.9 mmol), and finally DMAP (0.872 g; 7.14 mmol). The reaction mixture is stirred at 10–15 °C for 1 hour and then for another 12–14 hours at 22–24 °C. The precipitate is then filtered and washed with DCM (3 x 20 mL). The permeate is concentrated under reduced pressure (T bain(=30 °C, 5 mbar) to lead to a two-phase system comprising a yellow-orange oil and a white solid (residual dicyclohexylurea). The product is isolated by silica column chromatography (l = 28 cm, d = 4.5 cm) by eluting with a mixture of petroleum ether and ethyl acetate (v / v, 3:1). The fractions of interest are combined and concentrated under reduced pressure (Tbain = 40 °C, 4 mbar) to obtain a colorless, transparent oil (5.794 g, 15.56 mmol). Yield: 65%, purity: 98% (1H NMR). NMR attribution (CDCl3): Table 1 №δ 1H (ppm) δ 13C (ppm)1 5.74-5.90 136.12 4.99-5.10 116.13 2.38-2.46 28.74 2.58 33.5 5 / 170,7 6 / 151,1 7 6.75 112.72.2. Synthesis of compound A To a solution of benzene-1,3,5-triyl tris(pent-4-enoate) (compound A-1; 5.794 g, 15.56 mmol) in DCM (150 mL), MCPBA (13.420 g; ≤77%) is added in portions over 20 minutes. The reaction mixture is stirred at 22–24 °C for 24 hours. The resulting precipitate is then filtered and washed through DCM (3 x 20 mL). The permeate is stirred with an aqueous solution of Na₂SO₃ (30 g in 120 mL of water) for 5 hours. After separation, the aqueous phase is extracted through DCM (2 x 30 mL). The combined organic phases are stirred with an aqueous solution of NaHCO₃ (30 g in 120 mL of water) for 5 hours. After separation, the aqueous phase is extracted by DCM (2 x 30 mL). The combined organic phases are washed with demineralized water (30 mL) and finally evaporated under reduced pressure (Tbain = 40 °C, 5 mbar) to produce a yellowish oil.The target product is isolated by silica column chromatography (l = 30 cm, d = 4.5 cm) by eluting with a mixture of petroleum ether and ethyl acetate (v / v, 1:2). The fractions of interest are combined, concentrated under reduced pressure (Tbain = 40 °C, 10 mbar), and then dried under deep vacuum (TA, 14 h, 0.15 mbar). A clear oil (4.803 g, 11.42 mmol) is obtained. Yield: 73%. This product crystallizes slowly at room temperature to give a white solid with a melting point of 45.9 °C. The purity is 93% (1H NMR). NMR attribution (CDCl3): Table 2 №δ 1H (ppm) δ 13C (ppm)1 2.50 and 2.74 47.02 2.95-3.02 51.03 1.71-1.85 and 1.99-2.12 27.44 2.63 30.5 5 / 170,6 6 / 151,0 7 6.79 112.73. Synthesis of compound B (benzene-1,3,5-triyl tris(9-(oxiran-2-yl)nonanoate) The synthesis of compound B is carried out in two steps starting from phloroglucinol. 3.1. Synthesis of Compound B-1 Under argon protection, a solution of phloroglucinol (3.00 g; 23.8 mmol) in anhydrous THF (150 mL) is cooled slightly to 10 °C. Then, the following are added in the specified order: 10-undecenoic acid (15.78 g; 86.0 mmol), DCC (15.46 g; 74.9 mmol), and finally DMAP (0.872 g; 7.14 mmol). The reaction mixture is stirred at 10–15 °C for 1 hour and then for another 12–14 hours at 22–24 °C. The precipitate is then filtered and washed through a filter with DCM (3 x 20 mL). The permeate is concentrated under reduced pressure (Tbain = 30 °C, 5 mbar) to yield a slightly yellowish solid. This material is dissolved in a mixture of pentane and ethyl acetate (75 mL; 20:1, v / v) and filtered through silica (l = 5 cm) by eluting with 150 mL of the previously mentioned mixture. This procedure is repeated four times in series.Finally, the permeate is concentrated under reduced pressure (Tbain = 40°C, 8 mbar) to produce a clear oil. A colorless oil (8.59 g, 13.75 mmol) is obtained. Yield: 58%, mass purity: 94% (1H NMR). NMR assignment (CDCl3):. Table 3 δ1H (ppm) δ13C (ppm) 4.90 115.22 5.75 140.23 1.98 34.64 1.32 29.95 1.25 29.99 1.66 25.510 2.46 35.211 / 172.312 / 152.213 6.75 113.73 2. Synthesis of Compound B To a solution of benzene-1,3,5-triyl tris(undec-10-enoate) (compound B-1; 5.00 g, 8.00 mmol) in DCM (100 mL), MCPBA (6.90 g, ≤ 77%) is added in portions over 10–12 minutes. The reaction mixture is stirred at 22–24 °C for 24 hours. The resulting precipitate is then filtered and washed through DCM (3 x 15 mL). The permeate is stirred with an aqueous solution of Na₂SO₃ (15 g in 100 mL of water) for 5 hours. After separation, the aqueous phase is extracted with DCM (30 mL). The combined organic phases are stirred with an aqueous solution of NaHCO₃ (15 g in 100 mL of water) for 5 hours. After separation, the aqueous phase is extracted by DCM (30 mL). The combined organic phases are washed with demineralized water (30 mL) and finally evaporated under reduced pressure (Tbain = 40 °C, 5 mbar) to produce a yellowish oil.This crude product is solubilized in a mixture of pentane and ethyl acetate (20 mL, 3:1, v / v) and filtered through a silica layer (approx. 5 cm) by eluting with the previously mentioned mixture (50 mL). The permeate is then concentrated under reduced pressure (Tbain = 40°C, 7 mbar) to obtain a colorless oil (3.274 g, 4.87 mmol). Yield: 61%, mass purity: 94% (1H NMR). NMR attribution (CDCl3): Table 4 δ1H (ppm) δ13C (ppm) 1 2.40 and 2.68 46.42 2.84 51.23 1.46 31.54 1.39 24.65-8 1.25-1.35 28.19 1.65 23.810 2.46 33.311 / 171.112 / 151.113 6.75 112.04. Synthesis of compound C (benzene-1,3,5-triyl tris(7-oxabicyclo[4.1.0]heptane-3-carboxylate)) The synthesis of compound C is carried out in two steps starting from phloroglucinol. 4.1. Synthesis of compound C-1(benzene-1,3,5-triyl tris(cyclohex-3-ene-1-carboxylate)) Under argon protection, a solution of phloroglucinol (4.00 g, 31.7 mmol) in anhydrous THF (200 mL) is cooled to 10 °C. Then, the following are added in the specified order: 3-cyclohexene-1-carboxylic acid (14.55 g, 113 mmol), EDC (21.67 g, 113 mmol), and finally DMAP (1.16 g, 9.5 mmol). The reaction mixture is stirred at 10–15 °C for 1 hour and then left overnight at room temperature. The precipitate is then filtered twice and washed with DCM (2 x 40 mL). The permeate is concentrated under reduced pressure (Tbain = 40 °C, 50 mbar) to yield a yellow oil. It is redissolved in DCM (130 mL) and washed with distilled water (5 x 130 mL) until the EDC adduct disappears. The organic phase is dried with Na₂SO₄ and concentrated under reduced pressure. A slightly yellowish solid (12.5 g, 23.0 mmol) is obtained. Yield: 73%, mass purity: 83% (1H NMR), melting point: 66 °C. NMR assignment (CDCl₃): Table 5 №δ 1H (ppm) δ 13C (ppm)1 6.76 112.6 2 / 151,2 3 / 173,54 2.71 39.45 2.31 27.26 5.66 124.87 5.66 126.78 2.09 24.29 1.75 24.94.2. Synthesis of Compound C: A solution of benzene-1,3,5-triyltris(cyclohex-3-ene-1-carboxylate) (compound C-1; 12.0 g, 22.1 mol) in DCM (250 mL) is cooled to 0 °C. After cooling, MCPBA (28.84 g, ≤ 77%) is slowly added so as not to exceed 10 °C in the medium. The reaction mixture is stirred at room temperature overnight. Then, the resulting precipitate is filtered and washed with DCM (2 x 50 mL). The permeate is stirred for 7 h with a 10% concentrated aqueous Na₂SO₃ solution (250 mL). After separation, the aqueous phase is extracted with DCM (2 x 60 mL). The organic phases are combined and stirred with an aqueous NaHCO₃ solution (60 g in 240 mL of water) overnight. After separation, the aqueous phase is extracted with DCM (2 x 60 mL). The combined organic phases are washed with distilled water (60 mL) and finally evaporated under reduced pressure (T bain(= 40°C, 5 mbar) to conduct an oil that crystallizes slowly at room temperature. A white solid (11.5 g, 21.0 mmol) is obtained. Yield 95%, mass purity: 91% (1H NMR), melting point: 118 °C. According to the NMR analysis, it is likely that the coexisting endo- and exo- forms generate similar but distinct peaks. NMR attribution (CDCl3): Table 6 №δ 1H (ppm) δ 13C (ppm)1 6.73 112.4l' 6.74 112.5 2 / 151,0 2' / 151.0 3 / 172,9 3' / 172.24 2.69 35.94' 2.43 37.45 2.02-2.33 26.95' 2.22-2.26 26.36 3.22 51.86' 3.16 50.57 3.13 51.27' 3.14 51.48 1.84-1.96 22.68' 1.79-2.21 23.29 1.48 22.69' 1.67 20.85. Synthesis of compound D (benzene-1,3,5-triyl tris(2-methyloxirane-2-carboxylate)) The synthesis of compound D is carried out in two steps starting from phloroglucinol. 5.1. Synthesis of compound D-1 The compound D-1 (1,1',1''-(1,3,5-benzenetriyl) tris(2-methyl-2-propenoate) can be obtained according to the protocol described in US document 20200317870. NMR attribution (CDCl3): Table 7 №δ 1H (ppm) δ 13C (ppm)1 7.09 114.2 2 / 151,6 3 / 125,3 4 / 135,45 5.92 and 6.29 128.76 2.01 18.45.2 Synthesis of Compound D. To a solution of (1,1',1''-(1,3,5-benzenetriyl)tris(2-methyl-2-propenoate) (compound D-1; 3.00 g, 9.08 mmol) in DCM (100 mL), MCPBA (7.84 g, ≤ 77%) is added in portions over 8-10 minutes. The reaction mixture is stirred at 22-24 °C for 24 hours. The resulting precipitate is then filtered and washed through DCM (2 x 10 mL). The permeate is stirred with an aqueous solution of Na₂SO₃ (10 g in 50 mL of water) for 5 hours. After separation, the aqueous phase is extracted through DCM (30 mL). The collected organic phases are stirred with an aqueous solution of NaHCO3 (10 g in 50 mL of water) for 5 hours. After separation, the aqueous phase is extracted by DCM (30 mL). The combined organic phases are washed with demineralized water (3 x 20 mL) and finally evaporated under reduced pressure (Tbain = 40 °C, 5 mbar) to yield a colorless oil (3.257 g; 8.61 mmol).Yield 95%, mass purity: greater than 75% (1H NMR). NMR attribution (CDCl3):. Table 8 №δ 1H (ppm) δ 13C (ppm)1 6.8 113.0 2 / 151,4 3 / 168,6 4 / 53,65 2.80 and 3.18 53.16 1.60 17.26. Evaluation of the properties of compound (A) The properties of compound (A) with respect to DGEBA were evaluated in thermosetting materials. Different amine derivatives (crosslinking agent) were combined with this new monomer to study its thermal properties in formulation and thus compare them to DGEBA-based formulations: • Priamine 1071 (pf < -30 °C, AHEW = 140 g / eq), • Urea (pf = 132-135 °C, AHEW = 15 g / eq). The protocol for thermal properties in formulation was carried out as follows. The monomer was weighed with the corresponding diamine (1 equivalent with respect to the reactive functions). The mixture was dissolved in a DMSO:water mixture (% mass = 74:26) at a mass concentration between 10 and 12%. 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 portion of the material, obtained after preheating, was taken to continue the second part of the reaction in the DSC (aluminum crucible with reaction temperature < decomposition temperature), under helium at 40 mL / min at 80 or 210 °C for 60 minutes. The glass transition temperature (Tg) of the material obtained was then measured by DSC, under helium at 40 mL / min, according to the method: 1. cooling from 25 °C to -150 °C at -50 °C / min, 2. isothermal from -150 °C for 18 min, 3. heating from -150 °C to +250 °C at 50 °C / min, 4. isothermal from -150 °C for 18 min, 5. The heating process was carried out from -150 °C to +250 °C at 50 °C / min. The Tg was measured on the last heating ramp. Several tests were performed by varying the monomer used, the crosslinking agent (the diamine) used, and certain reaction conditions. These tests are summarized in the table below. Table 9 E. ssai 1 2 3 4 Compound (A) according to Monomer DGEBA the invention Priamine Priamine D iamine UréeUrea 1071 1071 molar equivalent molecule1:1.33 1:2diamine:monomer molar equivalent function 1 :1 1:1 (NH:epoxide) Mass. reactants (%) 9.6 12.44 12 12 Preheating time (min) 100 100 60 60 Preheating temperature 120 120 120 120 (°C) Reaction time (min) 60 60 60 60 Reaction temperature (°C) 80 80 210 210 Tg (°C) 33.97 21.32 29.80 23.59 The glass transition temperature of materials prepared from compound (A) compared to those prepared from DGEBA have a similar glass transition temperature, regardless of the crosslinking agent (Urea or Priamine 1071). These results demonstrate that the use of 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 disadvantage of being derived from bisphenol A and epichlorohydrin and thus having improved HSE properties.

Claims

CLAIMS 1. Formula compound (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-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 linked together, with the carbon atoms of the epoxide group, to form a C4 to C8 carbocycle or a heterocycle having 5 to 8 links; - the symbol (*) represents the point of attachment of group (II) to the rest of the compound of formula (I); - R5 represents a group of formula (II) identical to R1 and R3 or -O-X4, with X4 representing a C1-C18 alkyl, a C2-C18 alkenyl, a C6-C14 aryl or a (C6-C14)aryl-(C1-C6)alkyl, preferably R5 represents a group of formula (II) identical to R1 and R3; -R2, R4 and R6, identical or different, represent a hydrogen atom or a C1-C2 alkyl.

2. Compound according to claim 1, characterized in that R2, R4 and R6, identical or different, represent a hydrogen atom or a C1-C4 alkyl, preferably, R2, R4 and R6 represent a hydrogen atom.

3. Compound according to claim 1 or 2, characterized in that E represents a C1-C4 hydrocarbon divalent group, typically in C2, or in C5-C10, typically in C8, optionally comprising one or more heteroatoms, preferably E represents a C1-C4 alkyl, typically in C2, or in C5-C10, typically in C8, optionally comprising one or more heteroatoms.

4. A compound according to any one of claims 1 to 3, characterized in that X1, X2 and X3, whether identical or different, represent a hydrogen atom or a C1-C6 alkyl group, preferably a hydrogen atom or a methyl group, 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, preferably a saturated C4-C8 carbocycle, advantageously a cyclopentane, cyclohexane or cycloheptane. 5.Composed according to any one of claims 1 to 4, chosen from the group constituted,. , , et their mixtures.

6. A process for preparing a compound of formula (I) according to any one of claims 1 to 5, comprising a step b) of epoxidizing a compound of formula (I- in which: - R1'' and R3'' are identical and designate a group according to the following formula (II-2): 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 epoxide group to form a C4-C8 carbocycle or a heterocycle having 5 to 8 members; - the symbol (*) represents the point of attachment of the group of formula (II-2) to the rest of the compound of formula (I-2); - R5'' denotes a group identical to R1'' and R3'', or -O-X4, with X4 representing a C1-C18 alkyl, a C2-C18 alkenyl, a C6-C14 aryl or (C6-C14)aryl-(C1-C6)alkyl;- R2, R4 and R6, whether identical or different, represent a hydrogen atom or an alkyl in C1-C24, preferably a hydrogen atom or an alkyl in C1-C12, preferably a hydrogen atom or an alkyl in C1-C6, preferably a hydrogen atom or an alkyl in C1-C4, more preferably still a hydrogen atom.; 7. A process according to claim 6, further comprising a step a) preceding step b), step a) being a step of bringing the following compounds into contact: - a compound of formula (I-1) in which: - R1' and R3' denote an -OH group, - R5' denotes an -OH or -O-X4 group, with X4 as defined in claim 6, and - R2, R4 and R6 are as defined in claim 6; with - a compound according to the following formula (II-1): in which: - Y represents a group halogen atom, with Ra representing a C1-C6 alkyl, and -E, X1, X2 and X3 are as defined in claim 6.

8. Use of a compound of formula (I) according to any one of claims 1 to 5 as a precursor of polymeric materials, in particular thermosetting materials, or as an adhesive.

9. Process for preparing a thermosetting material comprising a polymerization step of a compound of formula (I) according to any one of claims 1 to 5, optionally the process further comprises a crosslinking step.

10. Thermosetting material that can be obtained by the process according to claim 9.

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