Novel plasticizers, process for the preparation thereof, and use thereof

Abstract

The invention relates to the use of a composition comprising at least one derivative compound which is derived from cashew nut shell oil (CNSL) and which has at least one ester function and / or at least one epoxide function, as a plasticizer for cellulose acetate, for the preparation of a plastic material comprising or consisting of cellulose acetate.

Description

[0001] DESCRIPTION

[0002] Title: New plasticizing agents, their preparation process and their use

[0003] The present invention relates to novel compounds in the field of plastic materials, as plasticizing agents, in particular cellulose acetate. The invention also relates to a process for preparing such plastic materials.

[0004] CONTEXT OF THE INVENTION

[0005] 'Plastic materials are mostly of petroleum origin. In most cases, they are not biodegradable, leading to plastic pollution ending up in the oceans and problematic management in terms of recycling.

[0006] However, today, consumers are increasingly concerned about ecological and health issues, and are therefore expecting environmentally friendly materials that are safe for their health.

[0007] In this context, we now find on the market plastics containing components of plant origin, such as bio-sourced plastics, most of which come from wheat, corn, beetroot, sugar cane or potatoes, i.e. from intensive cultivation whose production competes with human food.

[0008] There is therefore a need to provide consumers with alternative plastic materials that are sustainably bio-sourced, ecological and biodegradable and have thermoplastic properties equivalent to those of plastics from the petroleum industry.

[0009] Cellulose is one of the most abundant biopolymers. Substitution of hydroxyl groups in cellulose with other functional groups is essential to achieve thermoplastic properties. Cellulose derivatives are characterized by their degree of substitution (DOS), i.e., the average number of substituent groups present per anhydroglucopyranose unit (AGU). The DOS can range from 0 (no hydroxyl groups are replaced) to 3 (all hydroxyl groups are replaced).

[0010] Cellulose acetate is a substitution with acetyl groups (-COCH3). Cellulose acetate is one of the most common cellulose derivatives in industry, due to its many properties. It is a transparent, glossy, non-flammable, and strong polymer with good dimensional stability and high resistance to heat and chemicals. The formula for cellulose acetate with a DS of 2.0 is as follows, where n represents the number of monomers, or the degree of polymerization:

[0011] To meet the desired technical properties of plastics, additives are often added to cellulose acetate. Among the additives, plasticizers are small organic molecules that reduce its brittleness, improve its flexibility by reducing its crystallinity and lowering its glass transition and melting temperature.

[0012] The ideal plasticizer sought must be able to significantly reduce the glass transition temperature (Tg), must be biodegradable, non-volatile and non-toxic, and must migrate little over time. To achieve effective plasticization, compatibility between the plasticizer and the polymer is a major factor. Indeed, if the plasticizer and the polymer have a strong compatibility, this can lead to the establishment of bonds that would lead to a stiffening of the material. However, they must be sufficiently compatible so that the plasticizer does not migrate prematurely.

[0013] In biopolymer-based films, an incompatibility generally appears, which is evidenced by the biopolymer / plasticizer phase separation, presented in the form of drops exuded on the surface of the film.

[0014] Cashew Nut Shell Oil or CNSL is a natural oil derived from cashew nut shells. The main components of raw CNSL are phenolic compounds: anacardic acid, cardol and cardanol. Methyl cardol is also present, but in trace amounts. Each of these compounds is itself a mixture of products, substituted by an alkyl or alkenyl chain, said alkenyl chain having 1, 2 or 3 double bonds (Diagram anacardic acid cardol methyl cardol cardanol

[0015] 65% 15 to 20% trace 10%

[0016] Scheme 1 - Chemical structures of the main constituents of CNSL.

[0017] CNSL can be classified into 2 types, depending on the extraction method used:

[0018] • CNSL extract, obtained by extraction using a solvent,

[0019] • Technical CNSL, obtained by hot processes, in particular by high temperature roasting, eg >250°C.

[0020] To date, the valorization of CNSL oil remains to be done given the potential presented by the components that constitute it.

[0021] One of the aims of the invention is the use of compounds derived from natural products as plasticizing agents for biopolymers.

[0022] Another aim of the invention is the use of compounds derived from plant sources as plasticizing agents allowing compatibility with biopolymers, in order to obtain biodegradable plastic materials.

[0023] Another aim of the invention is the use of compounds obtained from natural compounds contained in agricultural production waste for their recovery.

[0024] Yet another aim of the present invention is to provide a plastic material from bio-sourced materials which does not come from intensive cultivation, the production of which competes with human food.

[0025] Yet another object of the invention is a process for preparing such plastic materials. A first object of the present invention is the use of a composition comprising at least one compound derived from CNSL which comprises at least one ester function and / or at least one epoxide function, as a plasticizing agent for cellulose acetate, for the preparation of a plastic material comprising or consisting of cellulose acetate.

[0026] The inventors have surprisingly found that compounds derived from cashew nut shells, currently little or not at all used, as well as products inspired by these compounds, with similar structures, can be transformed into derivatives with interesting properties as plasticizing agents.

[0027] Indeed, phenolic compounds present in cashew nut shell oil (CNSL) can be esterified and / or peroxidized to lead to compounds that can be used as plasticizing agents for cellulose acetate to form plastic materials.

[0028] Technical CNSL contains a reduced amount of anacardic acid, due to partial decarboxylation during roasting. In some cases, decarboxylation is even complete, and the CNSL no longer contains anacardic acid.

[0029] By "crude, undecarboxylated CNSL" we mean CNSL that has not undergone, or has only partially undergone, decarboxylation of anacardic acid. Crude, undecarboxylated CNSL is therefore characterized by the presence of anacardic acid in the mixture.

[0030] The CNSL, a cashew nut shell oil, used in the present invention is preferably a "crude CNSL", not having undergone decarboxylation, or a CNSL having undergone only partial decarboxylation of anacardic acid.

[0031] In other words, the CNSL used in the present invention is preferably a "CNSL" comprising at least 5% by mass of anacardic acid, or in which the sum of the percentage of anacardic acid, cardol, and methyl cardol is at least 15% by mass.

[0032] By "at least 5% by mass of anacardic acid" is also meant: at least 10% by mass, at least 20% by mass, at least 30% by mass, at least 40% by mass, at least 50% by mass, preferably at least 60% by mass.

[0033] By "the sum of the percentage of anacardic acid, cardol, and methyl cardol is at least 15% by mass" is also meant: at least 25% by mass, at least 35% by mass, at least 45% by mass, at least 55% by mass, at least 65% by mass, preferably at least 75% by mass.

[0034] By “CNSL derivative” we therefore mean a compound, or compounds, obtained from CNSL.

[0035] Indeed, it is possible to isolate anacardic acid or cardol, or methyl cardol, or cardanol in order to provide "pure" CNSL-derived compounds.

[0036] In this context, CNSL can be used as a mixture which is converted into derivative compounds of interest followed optionally by separation and purification.

[0037] By "CNSL derivative which comprises at least one ester function" is meant a compound derived from CNSL having an ester group, i.e. a group of formula -COOR formed from a carbon atom linked simultaneously to an oxygen atom by a double bond and to an alkoxy group, i.e. an oxygen linked to a carbon chain.

[0038] By "CNSL derivative which comprises at least one epoxide function" is meant a compound derived from CNSL having an epoxide group along a carbon chain, i.e. a group comprising an oxygen bridged on a carbon-carbon bond. i By "plasticizing agent" is meant an additive in the form of chemical compounds capable of creating interactions with cellulose acetate and modifying the properties of the biopolymer.

[0039] There are two main categories of plasticizing agents: - external plasticizers which are incorporated as an additive into a plastic compound, without the existence of covalent bonds between the polymer and the plasticizing agent; the latter can therefore be lost by evaporation, migration or extraction;

[0040] - internal plasticizers, more advantageous, are chemical groups incorporated by chemical reaction or grafting into a polymer for the purpose of plasticizing it; internal plasticizers generally have bulky structures providing structural materials that are bulkier enough to prevent the polymer chains from coming together.

[0041] The material obtained after plasticization is generally amorphous and can be used in conventional material shaping processes over a temperature range from that of the glass transition to that of degradation.

[0042] Advantageously in the present invention, the cellulose acetate used is preferably a cellulose acetate with a degree of substitution DS varying from 1.5 to 3.0, preferably 2.0 to 2.8, in particular 2.5.

[0043] The range "1.5 to 3.0" includes the ranges: 1.5 to 1.6; 1.6 to 1.7; 1.7 to 1.8; 1.8 to 1.9; 1.9 to 2.0; 2.0 to 2.1; 2.1 to 2.2; 2.2 to 2.3; 2.3 to 2.4; 2.4 to 2.5; 2.5 to 2.6; 2.6 to 2.7; 2.7 to 2.8; 2.8 to 2.9; 2.9 to 3.0.

[0044] The term "plastic material" means a material consisting of a polymer matrix mixed with additives, colorants or fillers with thermoplastic properties that allow it to be shaped and that exhibits properties of strength, transparency and lightness. Plastic materials can be presented in particular in the form of films, fabrics, or objects of defined shape.

[0045] By "plastic material comprising cellulose acetate" is meant that in said plastic material, part of the polymer matrix is ​​based on cellulose acetate.

[0046] By "plastic material made of cellulose acetate" is meant that the polymer matrix is ​​made of cellulose acetate without any other plastic material and further includes additives, colorants or fillers.

[0047] According to another particular embodiment, the present invention relates to the use as defined above, of a composition in which the compound derived from CNSL comprises at least one ester function and does not comprise an epoxide function, as a plasticizing agent for cellulose acetate, for the preparation of a plastic material comprising or consisting of cellulose acetate.

[0048] According to another particular embodiment, the present invention relates to the use as defined above, of a composition in which the compound derived from CNSL comprises an epoxide function and does not comprise an ester function for the preparation of a plastic material comprising or consisting of cellulose acetate.

[0049] According to another particular embodiment, the present invention relates to the use as defined above, of a composition in which the compound derived from CNSL comprises at least one ester function and comprises at least one epoxide function, as a plasticizing agent for cellulose acetate, for the preparation of a plastic material comprising or consisting of cellulose acetate.

[0050] According to another particular embodiment, the present invention relates to the use as defined above of a composition comprising at least one compound derived from CNSL which comprises at least one ester function and / or at least one epoxide function, as a primary plasticizing agent for cellulose acetate, for the preparation of a plastic material comprising or consisting of cellulose acetate. The expression "primary plasticizer" designates a molecule reducing the glass transition temperature and the modulus of elasticity of a polymer when it is added without other plasticizers. It is characterized by a chemical compatibility with the polymer that it plasticizes, which allows it to be solubilized therein to represent from 30 to 60% by mass relative to the total mass of the material.

[0051] A primary plasticizer is defined in contrast to a secondary plasticizer, which alone does not sufficiently reduce the glass transition temperature and the modulus of elasticity. Its properties depend on the application for which the material is developed. A secondary plasticizer requires the use of a primary plasticizer to form a plastic material. The compatibility of the secondary plasticizer with the polymer is significantly lower than that of the primary plasticizer. This incompatibility can lead, in particular, to the exudation of the secondary plasticizer, and this phenomenon can be avoided by adding the primary plasticizer.

[0052] According to another particular embodiment, the present invention relates to the use as defined above of a composition comprising at least one compound derived from CNSL which comprises at least one ester function and / or at least one epoxide function and not comprising linear ether functions, as primary plasticizing agent for cellulose acetate, for the preparation of a plastic material comprising or consisting of cellulose acetate.

[0053] According to another particular embodiment, the present invention relates to the use as defined above of a composition comprising cardol, as primary plasticizing agent for cellulose acetate, for the preparation of a plastic material comprising or consisting of cellulose acetate.

[0054] According to another particular embodiment, the present invention relates to the use as defined above of a composition, comprising at least one compound of formula (1) as primary plasticizing agent for cellulose acetate for the preparation of a plastic material comprising or consisting of cellulose acetate, formula (1) in which

[0055] • R is chosen from:

[0056] - a hydrogen atom or

[0057] - a CO-R1 group,

[0058] • Ro is chosen from:

[0059] - a linear alkyl group of 15 carbon atoms, optionally comprising 1 to 3 epoxide functions or,

[0060] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0061] • R2 is chosen from:

[0062] - a hydrogen atom,

[0063] -a carboxylic acid function COOH,

[0064] - -CO-O-R5 of formula

[0065] • Rs is chosen from:

[0066] - a hydrogen atom,

[0067] - an alcohol function -OH formula

[0068] • R4 is chosen from:

[0069] - a hydrogen atom or

[0070] - a methyl group CH3;

[0071] • Ri, Rs and Re, identical or different, are chosen from:

[0072] - a linear alkyl group of 1 to 30 carbon atoms, optionally comprising 1 to 6 epoxide functions, or

[0073] - a linear alkenyl group of 2 to 24 carbon atoms, optionally comprising 1 to 6 epoxide function(s), said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atom(s),

[0074] Ro, Ri, R5 and Re optionally comprising one to six substituent(s) chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, provided that at least one of the groups OR, R2 or R3 is an ester function and / or at least one of Ro, Ri, Rs or Re comprises at least one epoxide function or at least one of the compounds of the following formulas:

[0075] By "epoxide function" we mean a group comprising an oxygen bridged over a carbon-carbon bond.

[0076] By "alkenyl function" we mean an unsaturated C=C group, namely at least one carbon-carbon double bond(s).

[0077] We understand that x and y are positive integers and that x indicates the number of epoxide functions present in the Ro group and that y indicates the number of epoxide functions present in the Ro group. The number of epoxide or alkenyl functions present in the Ro group cannot be greater than 3.

[0078] When y is 0, it means that there is no epoxide group on the Ro group.

[0079] By “linear alkyl group of 1 to 30 carbon atoms” is meant a carbon chain of 1 to 30 carbon atoms.

[0080] By "optionally comprising from 1 to 6 epoxide functions" is meant that the carbon chain comprises from 0 to 6 epoxide functions. In other words, the carbon chain either comprises no epoxide function or comprises from 1 to 6 oxygen atom(s) bridged to the carbon atoms of the carbon chain.

[0081] By “linear alkenyl group of 2 to 24 carbon atoms” is meant a linear carbon chain of 2 to 24 carbon atoms comprising at least one alkenyl function, namely at least one carbon-carbon double bond(s).

[0082] An alkyl group of 1 to 5 carbon atoms means a linear or branched alkyl group comprising 1 to 5 carbon atoms. These include methyl, ethyl, propyl, butyl, and pentyl. The definition of propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl includes all possible isomers. For example, the term butyl includes n-butyl, / so-butyl, sec-butyl, and tert-butyl.

[0083] By "alkyl group of 1 to 3 carbon atoms" is meant a linear or branched alkyl group comprising 1 to 3 carbon atoms. These are methyl, ethyl, propyl and isopropyl groups.

[0084] According to another particular embodiment, the present invention relates to the use as defined above of a composition comprising at least one compound of formula (1) as a primary plasticizing agent for cellulose acetate for the preparation of a plastic material comprising or consisting of cellulose acetate,

[0085] (1) formula (1) in which

[0086] • R is chosen from:

[0087] - a hydrogen atom or

[0088] - a CO-R1 group,

[0089] • Ro is chosen from:

[0090] - a linear alkyl group of 15 carbon atoms, optionally comprising 1 to 3 epoxide functions or,

[0091] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0092] • R2 is chosen from:

[0093] - a hydrogen atom,

[0094] -a carboxylic acid function COOH, formula 3 is chosen from:

[0095] - a hydrogen atom,

[0096] - an alcohol function -OH formula 4 is chosen from:

[0097] - a hydrogen atom or - a methyl group CH3;

[0098] • Ri, R5 and Re, identical or different, are chosen from:

[0099] - a linear alkyl group of 1 to 30 carbon atoms, optionally comprising 1 to 6 epoxide functions, or

[0100] - a linear alkenyl group of 2 to 24 carbon atoms, optionally comprising 1 to 6 epoxide function(s), said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atom(s),

[0101] Ro optionally comprising one to six substituent(s) chosen from -OH, -OR? or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms,

[0102] Ri, R5 and R6 optionally comprising one or two substituent(s) chosen from -OH, -OR7 or OCOR7, provided that at least one of the groups OR, R2 or R3 is an ester function and / or at least one of Ro, Ri, 5 or R6 comprises at least one epoxide function or at least one of the compounds of the following formulas:

[0103] According to another particular embodiment, the present invention relates to the use as defined above, of a composition comprising at least one compound of formula (1), as a plasticizing agent for cellulose acetate for the preparation of a plastic material comprising or consisting of cellulose acetate, formula (1) in which

[0104] • R is chosen from:

[0105] - a hydrogen atom or

[0106] - a CO-R1 group,

[0107] • Ro is chosen from:

[0108] - a linear alkyl group of 15 carbon atoms, optionally comprising 1 to 3 epoxide functions or,

[0109] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0110] • R2 is chosen from:

[0111] - a hydrogen atom, formula

[0112] - a carboxylic acid function COOH,

[0113] • R3 is chosen from:

[0114] - a hydrogen atom,

[0115] - an alcohol function -OH, formula,

[0116] • R4 is chosen from:

[0117] - a hydrogen atom or

[0118] - a methyl group CH3;

[0119] • Ri, R5 and Rs, identical or different, are chosen from:

[0120] - a linear alkyl group of 1 to 30 carbon atoms, optionally comprising 1 to 6 epoxide functions, or

[0121] - a linear alkenyl group of 2 to 24 carbon atoms, optionally comprising 1 to 6 epoxide function(s), said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atom(s),

[0122] Ri, R5 and R6 optionally comprising one or two substituent(s) chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, provided that at least one of the groups OR, R2 or R3 is an ester function and / or at least one of Ro, Ri, Rs or Re comprises at least one epoxide function.

[0123] According to another particular embodiment, the present invention relates to the use as defined above, of a composition comprising at least one compound of formula (1), as a primary plasticizing agent for cellulose acetate for the preparation of a plastic material comprising or consisting of cellulose acetate, formula (1) in which

[0124] • R is chosen from:

[0125] - a hydrogen atom or

[0126] - a CO-R1 group,

[0127] • Ro is chosen from:

[0128] - a linear alkyl group of 15 carbon atoms, optionally comprising 1 to 3 epoxide functions or,

[0129] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0130] • R2 is chosen from:

[0131] - a hydrogen atom, formula - a carboxylic acid function COOH,

[0132] • R3 is chosen from:

[0133] - a hydrogen atom,

[0134] - an alcohol function -OH, formula,

[0135] • R4 is chosen from:

[0136] - a hydrogen atom or

[0137] - a methyl group CH3;

[0138] • Ri, R5 and R6, identical or different, are chosen from:

[0139] - a linear alkyl group of 1 to 30 carbon atoms, optionally comprising 1 to 6 epoxide functions, or

[0140] - a linear alkenyl group of 2 to 24 carbon atoms, optionally comprising 1 to 6 epoxide function(s), said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atom(s),

[0141] Ri, Rs and Re optionally comprising one or two substituent(s) chosen from -OH, -OR7 or OCOR7, in which R? is an alkyl group of 1 to 3 carbon atoms, provided that at least one of the groups OR, R2 or R3 is an ester function and / or at least one of Ro, Ri, R5 or Re comprises at least one epoxide function.

[0142] According to another particular embodiment, the present invention relates to the use as defined above, of a composition comprising at least one compound of formula (1b), as primary plasticizing agent for cellulose acetate for the preparation of a plastic material comprising or consisting of cellulose acetate, formula (1 b) in which

[0143] • R is chosen from:

[0144] - a hydrogen atom,

[0145] - a CO-R1 group,

[0146] • Ro is chosen from:

[0147] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0148] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0149] • R2 is chosen from:

[0150] - a hydrogen atom, formula

[0151] - a carboxylic acid function COOH,

[0152] • R3 is chosen from:

[0153] - a hydrogen atom,

[0154] - -OC-O-R6 of formula

[0155] - an alcohol function -OH,

[0156] • R4 is chosen from:

[0157] - a hydrogen atom,

[0158] - a methyl group CH3,

[0159] • Ri, R5 and Re, identical or different, are chosen from:

[0160] - a linear alkyl group of 1 to 30 carbon atoms, or

[0161] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s),

[0162] Ro optionally comprising one to six substituent(s) chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms,

[0163] Ri, R5 and Re optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 or OCOR7, provided that at least one of the groups OR, R2 or R3 is an ester function.

[0164] According to another particular embodiment, the present invention relates to the use as defined above, of a composition comprising at least one compound of formula (1b), in which the group R odoes not include epoxy function.

[0165] According to another particular embodiment, the present invention relates to the use as defined above, of a composition comprising at least one compound of formula (1 d), as primary plasticizing agent for cellulose acetate for the preparation of a plastic material comprising or consisting of cellulose acetate, formula (1d) in which:

[0166] • R is chosen from:

[0167] - a hydrogen atom

[0168] - a CO-R1 group,

[0169] • Roep is chosen from:

[0170] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0171] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, optionally comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0172] Roep optionally comprising one to six substituent(s) chosen from -OH, OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms

[0173] • R2 is chosen from:

[0174] - a hydrogen atom,

[0175] - a carboxylic acid function COOH, or formula

[0176] • R3 is chosen from:

[0177] - a hydrogen atom, - an alcohol function OH, or

[0178] - -OC-O-Re of formula

[0179] 5t°Y Re 0

[0180] • R4 is chosen from:

[0181] - a hydrogen atom,

[0182] - a methyl group CH3,

[0183] • Ri, R5 and Re, identical or different, are chosen from:

[0184] - a linear alkyl group of 1 to 30 carbon atoms, optionally comprising 1 to 6 epoxide function(s), or

[0185] - a linear alkenyl group of 2 to 24 carbon atoms, optionally comprising 1 to 6 epoxide function(s), said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atom(s),

[0186] Ri, R5 and Re optionally comprising one or two substituent(s) chosen from -OH, -OR? or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, provided that at least one of the groups OR, R2 or R3 is an ester function and at least one of the groups Roep, Ri, Rs or Re comprises at least one epoxide function.

[0187] According to another particular embodiment, the present invention relates to the use as defined above, of a composition comprising at least one compound of formula (1 d), as primary plasticizing agent for cellulose acetate for the preparation of a plastic material comprising or consisting of cellulose acetate,

[0188] OR ep formula (1d) in which:

[0189] • R is chosen from:

[0190] - a hydrogen atom

[0191] - a CO-R1 group,

[0192] • Roep is chosen from:

[0193] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0194] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, optionally comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3

[0195] • R2 is chosen from:

[0196] - a hydrogen atom,

[0197] - a carboxylic acid function COOH, or formula

[0198] R3 is chosen from:

[0199] - a hydrogen atom,

[0200] - an alcohol function OH, or

[0201] - -OC-O-Re of formula

[0202] • R4 is chosen from:

[0203] - a hydrogen atom,

[0204] - a methyl group CH3,

[0205] • Ri, R5 and R6, identical or different, are chosen from:

[0206] - a linear alkyl group of 1 to 30 carbon atoms, optionally comprising 1 to 6 epoxide function(s), or

[0207] - a linear alkenyl group of 2 to 24 carbon atoms, optionally comprising 1 to 6 epoxide function(s), said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atom(s),

[0208] Roep optionally comprising one to six substituent(s) chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms,

[0209] Ri, R5 and RB optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 or OCOR7, provided that at least one of the OR, R2 or R3 groups is an ester function and at least one of the R groups Oep , Ri, Rs or R6 comprises at least one epoxide function.

[0210] According to another particular embodiment, the present invention relates to the use as defined above, of a composition in which the compound of formula (1 b) is chosen from the compounds of the following formulas (2), (3), (4), (5) and (6), in which R o is chosen from:

[0211] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0212] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3.

[0213] R4 is chosen from:

[0214] - a hydrogen atom, or

[0215] - a methyl group CH3

[0216] Ri, Rs and Re are chosen from:

[0217] - a linear alkyl group of 1 to 30 carbon atoms, or - a linear alkenyl group of 2 to 24 carbon atoms, said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atoms, said group R o optionally comprising one to six substituent(s) chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s) said groups R1, R5 and R6 optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 or OCOR7,

[0218] According to another particular embodiment, the present invention relates to the use as defined above, of a composition in which the compound of formula (1c) is chosen from the compounds of formulas (7), (8), and (9) below, in which R Oep is chosen from:

[0219] - a linear alkyl group of 15 carbon atoms comprising 1 to 3 epoxide functions, or

[0220] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 2, comprising y epoxide functions, y varying from 1 to 2, x + y being less than or equal to 3

[0221] Roep optionally comprising one to six substituent(s) chosen from -OH, OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms

[0222] According to another particular embodiment, the present invention relates to the use as defined above, of a composition in which the compound of formula (1d) is chosen from the compounds of formulas (10), (11), (12), (13) and (14) below, • in which Ro ep is chosen from:

[0223] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0224] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3

[0225] • R4 is chosen from:

[0226] - a hydrogen atom,

[0227] - a methyl group CH3

[0228] • Laugh P , Rs ep and R 6ep are chosen from:

[0229] - a linear alkyl group of 1 to 30 carbon atoms, optionally comprising 1 to 6 epoxide function(s), or

[0230] - a linear alkenyl group of 2 to 24 carbon atoms, optionally comprising from 1 to 6 epoxide function(s), said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atom(s), said Ro group epoptionally comprising one to six substituent(s) chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s), said groups Ri ep , Rs ep be ep optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 or OCOR7, provided that at least one of the R groups Oep , Laugh P , CSR P or R 6ep has at least one epoxy function.

[0231] We understand that:

[0232] - in formula (10), at least one of R Oep or Ri ep has at least one epoxy function,

[0233] - in formula (11), at least one of Ro ep or R5e P has at least one epoxy function,

[0234] - in formula (12), at least one of the Ro ep or Ri ep has at least one epoxy function,

[0235] - in formula (13), at least one of the Roe P , Laugh P or R5e P has at least one epoxy function,

[0236] - in formula (14), at least one of the Ro ep , Laugh P or Re ep has at least one epoxy function.

[0237] According to another particular embodiment, the present invention relates to the use as defined above, of a composition in which the compound of formula (1 b) is chosen from the compounds of formulas (2), (3), (4), (5) and (6) in which:

[0238] - Ro is chosen from:

[0239] - Ri, R5 and Re are chosen independently of one another from: o an alkyl group of 1 to 30 carbon atoms, o a linear alkenyl group of 2 to 24 carbon atoms, said alkenyl group being optionally substituted by an alkyl chain of 1 to 5 carbon atoms, said group Ro optionally comprising one to six substituent(s) chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s), said groups Ri, R5 and R6 optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR? or OCOR7, provided that at least one of the groups OR, R2 or R3 is an ester function.

[0240] It is understood that the left end of the o groups is linked to the phenolic group and the right end of the Ro groups is free.

[0241] According to another particular embodiment, the present invention relates to the use as defined above, of a composition in which the compound of formula (1c) is chosen from the compounds of formulas (7), (8) and (9), in which:

[0242] - Roep is chosen from: said Ro groupings ep optionally comprising 1 to 6 substituent(s) chosen from -OH, -OR7 and OCOR7

[0243] We understand that the left end of the Roep groups is linked to the phenolic group and the right end of the R groups Oep is free.

[0244] According to another particular embodiment, the present invention relates to the use as defined above, of a composition in which the compound of formula (1d) is chosen from the compounds of formulas (10), (11), (12), (13) or (14) in which:

[0245] Roep is chosen from:

[0246]

[0247] - Riep, Rsep and Reep are chosen independently of one another from: o an alkyl group of 1 to 30 carbon atoms, optionally comprising from 1 to 6 epoxide functions, o a linear alkenyl group of 2 to 24 carbon atoms, in particular comprising from 1 to 6 epoxide functions, said alkenyl group being optionally substituted by an alkyl chain of 1 to 5 carbon atoms, said Ro group ep optionally comprising one to six substituent(s) chosen from -OH, -OR? or ÔCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s), said groups Riep, Rsep and R 6ep optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 or OCOR7, provided that at least one of the Ro groups ep , Riep, Rsep or Reep has at least one epoxide function.

[0248] According to another particular embodiment, the present invention relates to the use as defined above, of a composition in which the compound of formula (1) is chosen from the compounds of the following formulas:

[0249] According to another particular embodiment, the present invention relates to the use as defined above, wherein at least one compound of formula (2), (3), (4), (5), (6), (7), (8), (9), (10), (11), (12), (13) or (14) is derived from CNSL, in particular from crude non-decarboxylated CNSL.

[0250] According to another particular embodiment, the present invention relates to the use as defined above, in which said composition comprises at least two compounds of formulae (2), (3), (4), (5), (6), (7), (8), (9), (10), (11), (12), (13) or (14).

[0251] A second subject of the present invention is a process for preparing a plastic material comprising or consisting of cellulose acetate, comprising a step of mixing cellulose acetate with a composition comprising at least one cellulose acetate plasticizing agent, said composition comprising as plasticizing agent at least one compound derived from CNSL as defined above according to the invention or at least one compound of formula (1) as defined above, to obtain said plastic material.

[0252] Another subject of the present invention is a process for preparing a plastic material comprising or consisting of cellulose acetate, comprising a step of mixing cellulose acetate with a composition comprising at least one primary plasticizing agent for cellulose acetate, said composition comprising as primary plasticizing agent at least one compound derived from CNSL as defined above according to the invention or at least one compound of formula (1) as defined above, to obtain said plastic material.

[0253] According to another particular embodiment, the present invention relates to a process for preparing a plastic material comprising or consisting of cellulose acetate, comprising a step of mixing cellulose acetate with a composition comprising at least one primary plasticizing agent for cellulose acetate, in an extruder, said composition comprising as primary plasticizing agent at least one compound derived from CNSL as defined above according to the invention or at least one compound of formula (1) as defined above, to obtain said plastic material.

[0254] Advantageously, the preparation of the plastic material can be carried out without solvent.

[0255] According to another particular embodiment, the present invention relates to a process as defined above in which the concentration rate by weight of the primary plasticizing agent is from 20 to 40%, preferably from 25 to 32%.

[0256] The 20-40% range includes the following ranges: 20-22%; 22-24%; 24-26%; 26-28%; 28-30%; 30-32%; 32-34%; 34-36%; 36-38%; 38-40%.

[0257] The 25-32% range includes the following ranges: 25-26%; 26-27%; 27-28%; 28-29%; 29-30%; 30-31%; 31-32%.

[0258] According to another particular embodiment, the present invention relates to a process as defined above in which the cellulose acetate and the primary plasticizing agent are mixed using an extruder.

[0259] Advantageously, the extruder is set at a temperature of 150 to 190°C and at a rotation speed of 150 to 200 rpm, preferably around 160 rpm.

[0260] The extruder is, by way of non-limiting example, a twin screw type extruder (22), a Noztek Touch extruder.

[0261] According to another particular embodiment, the present invention relates to a process for preparing a plastic material comprising or consisting of cellulose acetate, comprising a step of mixing cellulose acetate with a composition comprising at least one primary plasticizing agent for cellulose acetate, in a solvent, to form a solution, said composition comprising as primary plasticizing agent at least one compound derived from CNSL as defined above according to the invention or at least one compound of formula (1) as defined above, to obtain said plastic material in the solvent.

[0262] According to another particular embodiment, the present invention relates to a process as defined above, in which the cellulose acetate is chosen with a degree of substitution DS varying from 1.5 to 3.0, preferably 2.0 to 2.8, in particular 2.5.

[0263] The range "1.5 to 3.0" includes the ranges: 1.5 to 1.6; 1.6 to 1.7; 1.7 to 1.8; 1.8 to 1.9; 1.9 to 2.0; 2.0 to 2.1; 2.1 to 2.2; 2.2 to 2.3; 2.3 to 2.4; 2.4 to

[0264] 2.5; from 2.5 to 2.6; from 2.6 to 2.7; from 2.7 to 2.8; from 2.8 to 2.9; from 2.9 to 3.0.

[0265] According to another particular embodiment, the present invention relates to a process as defined above, in which the solvent used is chosen from acetone, methanol, ethanol, ethyl acetate, tetrahydrofuran (THF), methyltetrahydrofuran (Me-THF), butanone, butyl acetate or chloroform, in particular acetone.

[0266] According to another particular embodiment, the present invention relates to a method as defined above, in which the mixing step is carried out at room temperature, from 20 to 30°C, at atmospheric pressure (1 atm or 101,325 Pa).

[0267] The process for preparing the plastic material according to the invention requires few steps and the mixing of cellulose acetate and the primary plasticizing agent can be carried out at room temperature, from 20 to 30°C. Advantageously, it does not require a heating step for the incorporation of the plasticizing agent.

[0268] According to another particular embodiment, the present invention relates to a method as defined above, further comprising a step of evaporating said solvent from said solution, to obtain said plastic material.

[0269] Advantageously, the solvent evaporation step is carried out at room temperature, from 20 to 30°C, at atmospheric pressure (1 atm or 101,325 Pa).

[0270] According to another particular embodiment, the present invention relates to a process as defined above, in which the total quantity by weight of cellulose acetate and primary plasticizing agent represents from 1 to 50% of the solution by weight, in particular from 10 to 30%, preferably 10%.

[0271] The range from 1 to 50% includes the ranges: from 1 to 5%; from 5 to 10%; from 10 to 15%; from 15 to 20%; from 20 to 25%; from 25 to 30%; from 30 to 35%; from 35 to 40%; from 40 to 45%; from 45 to 50%.

[0272] According to another particular embodiment, the present invention relates to a process as defined above, in which the ratio between the quantity of primary plasticizing agent by weight and cellulose acetate by weight varies from 1 to 50% by weight, in particular from 10 to 30%, preferably approximately 30%.

[0273] According to another particular embodiment, the present invention relates to a process for preparing a plastic material comprising or consisting of cellulose acetate, comprising a step of mixing cellulose acetate with a composition comprising at least one primary plasticizing agent for cellulose acetate, in a solvent, to form a solution, said composition comprising as primary plasticizing agent at least one compound derived from CNSL according to the invention or at least one compound of formula (1) as defined above according to the invention, to obtain said plastic material in the solvent, optionally further comprising a step of evaporating said solvent from said solution, to obtain said plastic material, and / or wherein the total amount by weight of cellulose acetate and primary plasticizing agent represents from 1 to 50% of the solution by weight, in particular from 10 to 30, preferably 10%;and / or wherein the ratio of the amount of primary plasticizing agent by weight to cellulose acetate by weight ranges from 1 to 50% by weight, in particular from 10 to 30%, preferably about 30%.;

[0274] The processes for preparing plastics by incorporating a plasticizing agent into a matrix based on cellulose acetate of the prior art and known to those skilled in the art can be adapted for the preparation of a plastic material comprising or consisting of cellulose acetate, comprising as plasticizing agent at least one compound derived from CNSL as defined above according to the invention or at least one compound of formula (1) as defined above.

[0275] According to another particular embodiment, the present invention relates to a process as defined above, in which, in the composition comprising the primary plasticizing agent, the latter is a compound of formula (2) formula (2) in which Ro represents:

[0276] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0277] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3, formula (2) in which Ri represents:

[0278] - a linear alkyl group of 1 to 30 carbon atoms, or

[0279] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s)

[0280] Ri optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms Ro optionally comprising one to six substituent(s) chosen from -OH, -OR7 or OCOR7, and further comprising a step A of preparing said compound of formula (2) from a compound of formula (15) with an acid of formula (16): formula (15) in which R o represents:

[0281] - a linear alkyl group of 15 carbon atoms optionally comprising from 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3, formula (16) in which Ri represents:

[0282] - a linear alkyl group of 1 to 30 carbon atoms, or

[0283] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl functions, said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atoms,

[0284] Ri optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR? or OCOR?, in which R? is an alkyl group of 1 to 3 carbon atoms Ro optionally comprising one to six substituent(s) chosen from -OH, -OR? or OCOR?.

[0285] According to another particular embodiment, the present invention relates to a method as defined above, in which, in the composition comprising the plasticizing agent, the latter is a compound of formula (2), and comprising the following steps:

[0286] • a step A of preparation of compound (2) consisting of an esterification of the compound of formula (15) with an acid of formula (16) to obtain the compound of formula (2),

[0287] • a step of mixing cellulose acetate with a composition comprising at least one cellulose acetate plasticizing agent in a solvent to form a solution, said composition comprising as plasticizing agent said compound of formula (2), to obtain said plastic material in the solvent,

[0288] • a step of evaporating said solvent from said solution to obtain said plastic material.

[0289] As a non-limiting example, step A of esterification of cardanol, (1 equivalent) with an acid (1 equivalent) can be carried out in the presence of dimethylamino pyridine (DMAP) and two equivalents of 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC), in which the mixture is stirred for 4 hours.

[0290] As a non-limiting example, step A of esterification of cardanol (1 equivalent) with an acid (1 equivalent) can be carried out in the presence of one equivalent of propylphosphonic anhydride (T3P) at 80°C in ethyl acetate, the mixture obtained being stirred for approximately 4 hours.

[0291] As a non-limiting example, step A of esterification of cardanol (1 equivalent) with an acid (1 equivalent) can be carried out in the presence of triethylamine (Et3N) in dichloromethane (DCM) at 0°C, for approximately 18 hours.

[0292] According to another particular embodiment, the present invention relates to a process as defined above, in which, in the composition comprising the primary plasticizing agent, the latter is a compound of formula (3) formula (3) in which Ro represents:

[0293] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0294] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3, formula (3) in which R5 represents:

[0295] - a linear alkyl group of 1 to 30 carbon atoms, or

[0296] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s),

[0297] Rs optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms Ro optionally comprising one to six substituent(s) chosen from -OH, -OR7 or OCOR7, and further comprising a step B of preparing a compound of formula (3) from a compound of formula (17) and an alcohol of formula (18): formula (17) in which R o represents:

[0298] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0299] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3, formula (18) in which R5 represents:

[0300] - a linear alkyl group of 1 to 30 carbon atoms, or

[0301] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s),

[0302] Rs, in addition to the -OH group represented in formula (18), optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms

[0303] Ro optionally comprising one to six substituent(s) chosen from -OH, -OR7 or OCOR7,

[0304] According to another particular embodiment, the present invention relates to a method as defined above, in which, in the composition comprising the plasticizing agent, the latter is a compound of formula (3), and comprising the following steps:

[0305] • a preparation step B of compound (3) consisting of an esterification of the compound of formula (17) with compound (18) to obtain a compound of formula (3),

[0306] • a step of mixing cellulose acetate with a composition comprising at least one cellulose acetate plasticizing agent in a solvent to form a solution, said composition comprising as plasticizing agent said compound of formula (3), to obtain said plastic material in the solvent,

[0307] • a step of evaporating said solvent from said solution to obtain said plastic material.

[0308] As a non-limiting example, the first step B of esterification of anacardic acid (1 equivalent) with alcohol (in excess) can be carried out in the presence of sulfuric acid in a mixture stirred and heated to reflux under argon for approximately 1 day.

[0309] According to another particular embodiment, the present invention relates to a process as defined above, in which, in the composition comprising the primary plasticizing agent, the latter is a compound of formula (4)

[0310] O

[0311] R<^OO rj^y ^OH

[0312] (4) formula (4) in which Ro represents:

[0313] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0314] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3. formula (4) in which Ri represents:

[0315] - a linear alkyl group of 1 to 30 carbon atoms, or

[0316] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s),

[0317] Ri optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR? or OCOR?, in which R? is an alkyl group of 1 to 3 carbon atoms Ro optionally comprising one to six substituent(s) chosen from -OH, -OR? or OCOR?, and further comprising a step C of preparing a compound of formula (4) from a compound of formula (17) and an acid of formula (19):

[0318] (17) (19) formula (17) in which Ro represents: - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0319] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3, formula (19) in which Ri represents:

[0320] - a linear alkyl group of 1 to 30 carbon atoms, or

[0321] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), said group Ri optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR? or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, said group Ro optionally comprising one to six substituent(s) chosen from -OH, -OR7 or OCOR7;

[0322] According to another particular embodiment, the present invention relates to a method as defined above, in which, in the composition comprising the plasticizing agent, the latter is a compound of formula (4), and comprising the following steps:

[0323] • a preparation step C of the compound of formula (4) consisting of a step of esterification of the compound of formula (17) with the compound (19) to obtain the compound of formula (4),

[0324] • a step of mixing cellulose acetate with a composition comprising at least one cellulose acetate plasticizing agent in a solvent to form a solution, said composition comprising as plasticizing agent said compound of formula (4), to obtain said plastic material in the solvent,

[0325] • a step of evaporating said solvent from said solution to obtain said plastic material.

[0326] As a non-limiting example, step C of esterification of anacardic acid (1 equivalent) with an acid (1 equivalent) can be carried out in the presence of dimethylamino pyridine (DMAP) and two equivalents of 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC), the mixture being stirred for approximately 4 hours.

[0327] As a non-limiting example, step C of esterification of anacardic acid (1 equivalent) with an acid (1 equivalent) can be carried out in the presence of one equivalent of propylphosphonic anhydride (T3P) in ethyl acetate at 80°C, for approximately 4 hours.

[0328] As a non-limiting example, step C of esterification of anacardic acid (1 equivalent) with an acid (1 equivalent) can be carried out in the presence of triethylamine (Et3N) in dichloromethane (DCM) at 0°C, for approximately 18 hours.

[0329] According to another particular embodiment, the present invention relates to a process as defined above, in which, in the composition comprising the primary plasticizing agent, the latter is a compound of formula (5) formula (5) in which Ro represents:

[0330] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0331] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0332] Ri and R5 represent:

[0333] - a linear alkyl group of 1 to 30 carbon atoms, or

[0334] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s),

[0335] Ri and R5 optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR? or OCOR?, in which R? is an alkyl group of 1 to 3 carbon atoms Ro optionally comprising one to six substituent(s) chosen from -OH, -OR? or OCOR?, and further comprising a step D of preparing a compound of formula (5) from a compound of formula (17) with an alcohol of formula (18) and an acid of formula (19): formula (17) in which Ro represents:

[0336] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0337] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3, formulas (18) and (19) in which Ri and Rs independently represent:

[0338] - a linear alkyl group of 1 to 30 carbon atoms, or

[0339] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), said groups Ri optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR? or OCOR?, in which R? is an alkyl group of 1 to 3 carbon atoms

[0340] Rs, in addition to the -OH group represented in formula (18), optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR? or OCOR? said Ro group optionally comprising one to six substituent(s) chosen from -OH, -OR? or OCOR?.

[0341] According to another particular embodiment, the present invention relates to a method as defined above, in which, in the composition comprising the plasticizing agent, the latter is a compound of formula (5), and comprising the following steps:

[0342] • a preparation step D of the compound of formula (5) consisting of: i) a first step of esterification of the compound of formula (17) with a compound (18) to obtain the intermediate compound:

[0343] OH O c ii) a second esterification step with a compound of formula (19) to obtain the compound of formula (5),

[0344] O

[0345] O ar

[0346] (5)

[0347] • a step of mixing cellulose acetate with a composition comprising at least one cellulose acetate plasticizing agent in a solvent to form a solution, said composition comprising as plasticizing agent said compound of formula (5), to obtain said plastic material in the solvent,

[0348] • a step of evaporating said solvent from said solution to obtain said plastic material.

[0349] By way of non-limiting example, the first step D of esterification i) of anacardic acid (1 equivalent) with alcohol (in excess) can be carried out in the presence of sulfuric acid in a mixture stirred and heated to reflux under argon for approximately 1 day.

[0350] As a non-limiting example, the second esterification step D ii) with an acid (1 equivalent) can be carried out in the presence of dimethylamino pyridine (DMAP) and two equivalents of 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC), the mixture obtained being stirred for 4 hours.

[0351] As a non-limiting example, the second esterification step D ii) with an acid (1 equivalent) can be carried out in the presence of one equivalent of propylphosphonic anhydride (T3P) in ethyl acetate at 80°C, for approximately 4 hours.

[0352] As a non-limiting example, the second esterification step D ii) with an acid (1 equivalent) can be carried out in the presence of triethylamine (Et3N) in dichloromethane (DCM) at 0°C, for approximately 18 hours.

[0353] According to another particular embodiment, the present invention relates to a method as defined above, in which, in the composition comprising the primary plasticizing agent, the latter is a compound of formula (6) formula (6) in which Ro represents:

[0354] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0355] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being lower R4 represents:

[0356] - a hydrogen atom,

[0357] - a methyl group CH3,

[0358] Ri and Re represent independently, in particular which may be identical:

[0359] - a linear alkyl group of 1 to 30 carbon atoms, or

[0360] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s),

[0361] Ri and Re optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms Ro optionally comprising one to six substituent(s) chosen from -OH, -OR7 or OCOR7, and further comprising a step E of preparing said compound of formula (6) from a compound of formula (20) with an acid of formula (21) and an acid of formula (22): formula (20) in which Ro represents:

[0362] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0363] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0364] R4 represents:

[0365] - a hydrogen atom,

[0366] - a methyl group CH3, formulas (21) and (22) in which Ri and Re represent independently, in particular which may be identical:

[0367] - a linear alkyl group of 1 to 30 carbon atoms, or

[0368] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s),

[0369] Ri and Re optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms Ro optionally comprising one to six substituent(s) chosen from -OH, -OR7 or OCOR7.

[0370] According to another particular embodiment, the present invention relates to a method as defined above, in which, in the composition comprising the plasticizing agent, the latter is a compound of formula (6), and comprising the following steps:

[0371] • a preparation step E of the compound of formula (6) consisting of an esterification of the compound of formula (20) with an acid of formula (21) and an acid of formula (22), in particular the acids of formulas (21) and (22) being identical, to obtain the compound of formula (6),

[0372] • a step of mixing cellulose acetate with a composition comprising at least one cellulose acetate plasticizing agent in a solvent to form a solution, said composition comprising as plasticizing agent said compound of formula (2), to obtain said plastic material in the solvent,

[0373] • a step of evaporating said solvent from said solution to obtain said plastic material.

[0374] As a non-limiting example, the esterification step E of cardol (1 equivalent) with two acids (2 equivalents) can be carried out in the presence of two equivalents of propylphosphonic anhydride (T3P) in ethyl acetate at 80°C, for approximately 4 hours.

[0375] According to another particular embodiment, the present invention relates to a process as defined above, in which, in the composition of the primary plasticizing agent, the latter is a compound of formula (7) formula (7) in which R Oep represents:

[0376] - a linear alkyl group of 15 carbon atoms comprising 1 to 3 epoxide functions, or

[0377] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 2, comprising y epoxide functions, y varying from 1 to 2, x + y being less than or equal to 3,

[0378] Roep optionally comprising one to six substituent(s) chosen from -OH, -OR? or OCORz, in which R? is an alkyl group of 1 to 3 carbon atoms and further comprising a step F of preparing said compound of formula (7) from a compound of formula (15) formula (15) in which Ro represents:

[0379] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0380] Ro optionally comprising one to six substituent(s) chosen from -OH, -OR? or OCOR?, in which R? is an alkyl group of 1 to 3 carbon atoms,

[0381] Thus, said compound of formula (15) comprises at least one additional alkenyl function compared to the compound of formula (7), said function being epoxidized to form said compound of formula (7). It is understood that the compound of formula (15) may be a compound already having epoxide functions but that the latter comprises at least one additional alkenyl function compared to the compound of formula (7).

[0382] According to another particular embodiment, the present invention relates to a method as defined above, in which, in the composition comprising the plasticizing agent, the latter is a compound of formula (7), and comprising the following steps:

[0383] • a preparation step F consisting of a step of epoxidation of a compound of formula (15) to obtain the compound of formula (7):

[0384] • a step of mixing cellulose acetate with a composition comprising at least one cellulose acetate plasticizing agent in a solvent to form a solution, said composition comprising as plasticizing agent said compound of formula (7), to obtain said plastic material in the solvent,

[0385] • a step of evaporating said solvent from said solution to obtain said plastic material.

[0386] By way of non-limiting example, the epoxidation step F of cardanol (1 equivalent) is carried out in the presence of formic acid (3 equivalents), sulfuric acid (0.01 equivalent) and hydrogen peroxide (2 equivalents) with stirring and heating at 65°C for approximately 3 hours.

[0387] For example, according to the following reaction scheme:

[0388] As a non-limiting example, the epoxidation step F of cardanol (1 equivalent) is carried out in the presence of 70% metachloroperbenzoic acid (mCPBA) (2 equivalents) in dichloromethane (DCM) mixed cold (0°C) then stirred at room temperature for approximately 18 hours.

[0389] According to another particular embodiment, the present invention relates to a process as defined above, in which, in the composition comprising the primary plasticizing agent, the latter is a compound of formula (8) formula (8) in which Roep represents:

[0390] - a linear alkyl group of 15 carbon atoms comprising 1 to 3 epoxide functions, or

[0391] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 2, comprising y epoxide functions, y varying from 1 to 2, x + y being less than or equal to 3, Roep optionally comprising one to six substituent(s) chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, and further comprising a step G of preparing a compound of formula (8) from a compound of formula (17) formula (17) in which R o represents:

[0392] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0393] Ro optionally comprising one to six substituent(s) chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms.

[0394] Thus said compound of formula (17) comprises at least one additional alkenyl function compared to the compound of formula (8), said function being epoxidized to form said compound of formula (8).

[0395] It is understood that the compound of formula (17) may be a compound already having epoxide functions but that the latter comprises at least one additional alkenyl function compared to the compound of formula (8).

[0396] According to another particular embodiment, the present invention relates to a method as defined above, in which, in the composition comprising the plasticizing agent, the latter is a compound of formula (8), and comprising the following steps:

[0397] • a preparation step G of the compound of formula (8) consisting of a step of epoxidation of the compound of formula (17) to obtain the compound of formula (8)

[0398] • a step of mixing cellulose acetate with a composition comprising at least one cellulose acetate plasticizing agent in a solvent to form a solution, said composition comprising as plasticizing agent said compound of formula (8), to obtain said plastic material in the solvent,

[0399] • a step of evaporating said solvent from said solution to obtain said plastic material.

[0400] By way of non-limiting example, the epoxidation step G of anacardic acid (1 equivalent) is carried out in the presence of formic acid (3 equivalents), sulfuric acid (0.01 equivalent) and hydrogen peroxide (2 equivalents) with stirring and heating at 65°C for approximately 3 hours.

[0401] As a non-limiting example, the epoxidation step G of anacardic acid (1 equivalent) is carried out in the presence of 70% metachloroperbenzoic acid (mCPBA) (2 equivalents) in dichloromethane (DCM) mixed cold (0°C) then stirred at room temperature for approximately 18 hours.

[0402] According to another particular embodiment, the present invention relates to a process as defined above, in which, in the composition comprising the primary plasticizing agent, the latter is a compound of formula (9) formula (9) in which Ro ep represents:

[0403] - a linear alkyl group of 15 carbon atoms comprising 1 to 3 epoxide functions, or

[0404] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 2, comprising y epoxide functions, y varying from 1 to 2, x + y being less than or equal to 3,

[0405] Roep optionally comprising one to six substituent(s) chosen from -OH, -OR? or OCOR?, in which R? is an alkyl group of 1 to 3 carbon atoms, R4 represents:

[0406] - a hydrogen atom,

[0407] - a methyl group CH3, and further comprising a step of preparing H said compound of formula (9) from a compound of formula (20) formula (20) in which Ro represents:

[0408] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0409] Ro optionally comprising one to six substituent(s) chosen from -OH, -OR? or OCOR?, in which R? is an alkyl group of 1 to 3 carbon atoms

[0410] R4 represents:

[0411] - a hydrogen atom,

[0412] - a methyl group CH3.

[0413] Thus the compound of formula (20) comprising at least one additional alkenyl function compared to the compound of formula (9), said function being epoxidized to form said compound of formula (9).

[0414] It is understood that the compound of formula (20) may be a compound already having epoxide functions but that the latter comprises at least one additional alkenyl function compared to the compound of formula (9).

[0415] According to another particular embodiment, the present invention relates to a process as defined above, in which in the composition comprising the plasticizing agent, the latter is a compound of formula (9), and comprising the following steps: • A step of preparation H of the compound of formula (9) consisting of a step of epoxidation of the compound of formula (20) to obtain the compound of formula (9),

[0416] Roep

[0417] (9)

[0418] • a step of mixing cellulose acetate with a composition comprising at least one cellulose acetate plasticizing agent in a solvent to form a solution, said composition comprising as plasticizing agent said compound of formula (4), to obtain said plastic material in the solvent,

[0419] • a step of evaporating said solvent from said solution to obtain said plastic material.

[0420] As a non-limiting example, the H epoxidation step of cardol (1 equivalent) is carried out in the presence of formic acid (3 equivalents), sulfuric acid (0.01 equivalent) and hydrogen peroxide (2 equivalents) with stirring and heating at 65°C for approximately 3 hours.

[0421] As a non-limiting example, the H epoxidation step of cardol (1 equivalent) is carried out in the presence of 70% metachloroperbenzoic acid (mCPBA) (2 equivalents) in dichloromethane (DCM), mixed cold (0°C) then stirred at room temperature for approximately 18 hours.

[0422] According to another particular embodiment, the present invention relates to a method as defined above, in which, in the composition comprising the primary plasticizing agent, the latter is a compound of formula (10) formula (10) in which Ro ep represents:

[0423] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0424] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0425] Roep optionally comprising one to six substituent(s) chosen from -OH, -OR? or OCOR?, in which R? is an alkyl group of 1 to 3 carbon atoms, Rie P represents:

[0426] - a linear alkyl group of 1 to 30 carbon atoms, optionally comprising 1 to 6 epoxide function(s), or

[0427] - a linear alkenyl group of 2 to 24 carbon atoms, optionally comprising 1 to 6 epoxide function(s), said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atom(s),

[0428] Laugh P optionally comprising one or six substituent(s), in particular one or two, chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, provided that at least one of the groups Roep or Ri epcomprises at least one epoxide function, and further comprising a step A of preparing a compound of formula (2) from a compound of formula (15) with an acid of formula (16): formula (2) and (15) in which R o represent:

[0429] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0430] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0431] Ro optionally comprising one to six substituent(s) chosen from -OH, -OR? or OCOR?, in which R? is an alkyl group of 1 to 3 carbon atoms, formula (2) and (16) in which Ri represent:

[0432] - a linear alkyl group of 1 to 30 carbon atoms, or

[0433] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s),

[0434] Ri optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, and further comprising a step I of preparing the compound of formula (10) from a compound of formula (2), provided that at least one of the groups R o or Ri has an alkenyl function,

[0435] Thus the compound of formula (2) comprises at least one additional alkenyl function compared to the compound of formula (10), said function being epoxidized to form said compound of formula (10).

[0436] It is understood that the compound of formula (2) may be a compound already having epoxide functions but that the latter comprises at least one additional alkenyl function compared to the compound of formula (10).

[0437] The additional epoxide function of the compound of formula (10) is located at the same position as the additional alkenyl function of the compound (3). In simpler terms, the compound of formula (10) is derived from an epoxidation of an alkenyl function present in the compound of formula (3).

[0438] This embodiment comprises a step A of esterification of cardanol of formula (15) with an acid of formula (16) followed by an epoxidation of at least one alkenyl function in the compound of formula (2).

[0439] Advantageously, epoxidations of several alkenyl functions present in compound (2) can be carried out to obtain compound (10). These epoxidations can be successive or simultaneous.

[0440] It is also possible to isolate compounds with different degrees of epoxidation using methods known to those skilled in the art.

[0441] According to another particular embodiment, the present invention relates to a method as defined above, in which, in the composition comprising the plasticizing agent, the latter is a compound of formula (10), and comprising the following steps:

[0442] • a preparation step A of the compound of formula (2) consisting of a step of esterification of the compound of formula (15) with an acid of formula (16) to obtain the compound of formula (2), a preparation step I of the compound of formula (10) which consists of a compound of formula (2) step to obtain the compound of formula (10),

[0443] • a step of mixing cellulose acetate with a composition comprising at least one cellulose acetate plasticizing agent in a solvent to form a solution, said composition comprising as plasticizing agent said compound of formula (10), to obtain said plastic material in the solvent,

[0444] • a step of evaporating said solvent from said solution to obtain said plastic material.

[0445] As a non-limiting example, the esterification step A of cardanol, (1 equivalent) with an acid (1 equivalent) can be carried out in the presence of dimethylamino pyridine (DMAP) and two equivalents of 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC), the mixture obtained being stirred for 4 hours.

[0446] As a non-limiting example, the esterification step A of cardanol (1 equivalent) with an acid (1 equivalent) can be carried out in the presence of one equivalent of propylphosphonic anhydride (T3P) at 80°C in ethyl acetate, for approximately 4 hours.

[0447] As a non-limiting example, the esterification step A of cardanol (1 equivalent) with an acid (1 equivalent) can be carried out in the presence of triethylamine (Et3N) in dichloromethane (DCM) at 0°C, for approximately 18 hours.

[0448] By way of non-limiting example, step I of epoxidation of compound (2) (1 equivalent) is carried out in the presence of formic acid (3 equivalents), sulfuric acid (0.01 equivalent) and hydrogen peroxide (2 equivalents) with stirring and heating at 65°C for approximately 3 hours.

[0449] As a non-limiting example, step I of epoxidation of compound (2) (1 equivalent) is carried out in the presence of 70% metachloroperbenzoic acid (mCPBA) (2 equivalents) in dichloromethane (DCM), mixed cold (0°C) then stirred at room temperature for approximately 18 hours.

[0450] For example, following the following reaction scheme:

[0451] According to another particular embodiment, the present invention relates to a method as defined above, in which, in the composition comprising the primary plasticizing agent, the latter is a compound of formula ( formula (11) in which Roep represents:

[0452] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0453] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0454] Roep optionally comprising one to six substituent(s) chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms Rsep represents:

[0455] - a linear alkyl group of 1 to 30 carbon atoms, optionally comprising 1 to 6 epoxide function(s) or

[0456] - a linear alkenyl group of 2 to 24 carbon atoms, optionally comprising 1 to 6 epoxide function(s), said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atom(s),

[0457] R 5epoptionally comprising one to six substituent(s), in particular one or two, substituent(s) chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, provided that at least one of the groups Roep or Rsep comprises at least one epoxide function, and further comprising a preparation step B of a compound of formula (3) from a compound of formula (17) and an alcohol of formula (18): R5OH

[0458] (3) (17) (18) formulas (3) and (17) in which Ro represent:

[0459] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0460] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0461] Ro optionally comprising one to six substituent(s) chosen from -OH, -OR? or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, formulas (3) and (18) in which R5represents:

[0462] - a linear alkyl group of 1 to 30 carbon atoms; or

[0463] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), said group Rs, in addition to the -OH group represented in formula (18), optionally comprising one to six substituent(s), in particular one or two, substituent(s) chosen from -OH, -OR? and OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s), and further comprising a step J of preparing a compound of formula (11) from a compound of formula (3), provided that at least one of the groups R oor R5 contains an alkenyl function,

[0464] Thus the compound of formula (3) comprises at least one additional alkenyl function compared to the compound of formula (11), said function being epoxidized to form said compound of formula (11).

[0465] It is understood that the compound of formula (3) may be a compound already having epoxide functions but that the latter comprises at least one additional alkenyl function compared to the compound of formula (11).

[0466] The additional epoxide function of the compound of formula (11) is located at the same position as the additional alkenyl function of the compound (3). In simpler terms, the compound of formula (11) is derived from an epoxidation of an alkenyl function present in the compound of formula (3).

[0467] This embodiment comprises a step B of esterification of anacardic acid of formula (17) with an alcohol of formula (18) to obtain the ester of formula (3) followed by an epoxidation of at least one alkenyl function of the compound of formula (3).

[0468] Advantageously, epoxidations of several alkenyl functions present in compound (3) can be carried out to obtain compound (11). These epoxidations can be successive or simultaneous.

[0469] It is also possible to isolate compounds with different degrees of epoxidation using methods known to those skilled in the art.

[0470] According to another particular embodiment, the present invention relates to a method as defined above, in which, in the composition comprising the plasticizing agent, the latter is a compound of formula (11), and comprising the following steps:

[0471] • a preparation step B of the compound of formula (3) consisting of an esterification B of the compound of formula (17) with a compound (18) to obtain the compound of formula (3),

[0472] • a preparation step J of the compound of formula (11) consisting of an epoxidation of the compound of formula (3) to obtain the compound of formula (11)

[0473] • a step of mixing cellulose acetate with a composition comprising at least one cellulose acetate plasticizing agent in a solvent to form a solution, said composition comprising as plasticizing agent said compound of formula (11), to obtain said plastic material in the solvent,

[0474] • a step of evaporating said solvent from said solution to obtain said plastic material.

[0475] As a non-limiting example, the first B of esterification of anacardic acid, (1 equivalent) with alcohol (in excess) can be carried out in the presence of sulfuric acid in a mixture stirred and heated to reflux under argon for approximately 1 day.

[0476] By way of non-limiting example, step J of epoxidation of compound (3) (1 equivalent) is carried out in the presence of formic acid (3 equivalents), sulfuric acid (0.01 equivalent) and hydrogen peroxide (2 equivalents) with stirring and heating at 65°C for approximately 3 hours.

[0477] As a non-limiting example, step J of epoxidation of compound (3) (1 equivalent) is carried out in the presence of 70% metachloroperbenzoic acid (mCPBA) (2 equivalents) in dichloromethane (DCM), mixed cold (0°C) then stirred at room temperature for approximately 18 hours.

[0478] According to another particular embodiment, the present invention relates to a method as defined above, in which, in the composition comprising the primary plasticizing agent, the latter is a compound of formula (12) formula (12) in which R Oep represents:

[0479] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0480] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0481] Roep optionally comprising one to six substituent(s) chosen from -OH, -OR? or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms,

[0482] Laugh P represents:

[0483] - a linear alkyl group of 1 to 30 carbon atoms, optionally comprising

[0484] 1 to 6 epoxy function(s), or

[0485] - a linear alkenyl group of 2 to 24 carbon atoms, optionally comprising 1 to 6 epoxide function(s), said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atom(s),

[0486] Laugh P optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, provided that at least one of the groups Roep or Ri ep comprises at least one epoxide function, and further comprising a step C of preparing a compound of formula (4) from a compound of formula (17) and an acid of formula (19): formulas (4) and (17) in which Ro represent:

[0487] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0488] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0489] Ro optionally comprising one to six substituent(s) chosen from -OH, -OR7 or OCORz, in which R7 is an alkyl group of 1 to 3 carbon atoms, formulas (4) and (19) in which Ri represents:

[0490] - a linear alkyl group of 1 to 30 carbon atoms, or

[0491] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), said group Ri optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 and OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s), provided that at least one of the groups R o or Ri comprises an alkenyl function, and further comprising a step K of preparing a compound of formula (12) from a compound of formula (4).

[0492] Thus the compound of formula (4) comprises at least one additional alkenyl function compared to the compound of formula (12), said function being epoxidized to form said compound of formula (12).

[0493] It is understood that the compound of formula (4) may be a compound already having epoxide functions but that the latter comprises at least one additional alkenyl function compared to the compound of formula (12).

[0494] The additional epoxide function of the compound of formula (12) is located at the same position as the additional alkenyl function of the compound (4). In simpler terms, the compound of formula (12) is derived from an epoxidation of an alkenyl function present in the compound of formula (4).

[0495] This embodiment comprises a step C of esterification on the phenol function of anacardic acid of formula (17) with a carboxylic acid of formula (19) to obtain the ester of formula (4) followed by an epoxidation of at least one alkenyl function of the compound of formula (4).

[0496] Advantageously, epoxidations of several alkenyl functions present in compound (4) can be implemented to obtain compound (12). These epoxidations can be successive or simultaneous.

[0497] It is also possible to isolate compounds with different degrees of epoxidation using methods known to those skilled in the art.

[0498] According to another particular embodiment, the present invention relates to a method as defined above, in which, in the composition comprising the plasticizing agent, the latter is a compound of formula (12), and comprising the following steps:

[0499] • a preparation step C of the compound of formula (4) consisting of a step of esterification of the compound of formula (17) with a compound (19) to obtain the compound of formula (4),

[0500] • a preparation step K of preparing the compound of formula (12) consisting of a step of epoxidation of the compound of formula (4) to obtain the compound of formula (12),

[0501] O

[0502] Rûep

[0503] (12)

[0504] • a step of mixing cellulose acetate with a composition comprising at least one cellulose acetate plasticizing agent in a solvent to form a solution, said composition comprising as plasticizing agent said compound of formula (12), to obtain said plastic material in the solvent,

[0505] • a step of evaporating said solvent from said solution to obtain said plastic material.

[0506] As a non-limiting example, the esterification step C of anacardic acid (17) (1 equivalent) with an acid (1 equivalent) can be carried out in the presence of dimethylamino pyridine (DMAP) and two equivalents of 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC), the mixture obtained being stirred for 4 hours.

[0507] As a non-limiting example, the esterification step C of anacardic acid (17) (1 equivalent) with a carboxylic acid (1 equivalent) can be carried out in the presence of one equivalent of propylphosphonic anhydride (T3P) at 80°C in ethyl acetate, for approximately 4 hours.

[0508] As a non-limiting example, the esterification step C of anacardic acid (17) (1 equivalent) with an acid (1 equivalent) can be carried out in the presence of triethylamine (Et3N) in dichloromethane (DCM) at 0°C, for approximately 18 hours.

[0509] By way of non-limiting example, step K of epoxidation of compound (4) (1 equivalent) is carried out in the presence of formic acid (3 equivalents), sulfuric acid (0.01 equivalent) and hydrogen peroxide (2 equivalents) with stirring and heating at 65°C for approximately 3 hours.

[0510] As a non-limiting example, step K of epoxidation of compound (4) (1 equivalent) is carried out in the presence of 70% metachloroperbenzoic acid (mCPBA) (2 equivalents) in dichloromethane (DCM), mixed cold (0°C) then stirred at room temperature for approximately 18 hours.

[0511] According to another particular embodiment, the present invention relates to a method as defined above, in which, in the composition comprising the primary plasticizing agent, the latter is a compound of formula (13) formula (13) in which Roep represents:

[0512] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0513] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0514] Roep optionally comprising one to six substituent(s) chosen from -OH, -OR? or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, Riep and Rsep independently represent:

[0515] - a linear alkyl group of 1 to 30 carbon atoms, optionally comprising 1 to 6 epoxide function(s), or

[0516] - a linear alkenyl group of 2 to 24 carbon atoms, optionally comprising 1 to 6 epoxide function(s), said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atom(s),

[0517] Riep and Rsep optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, provided that at least one of the groups Roep, Riep or Rsep comprises at least one epoxide function, and further comprising a step D of preparing a compound of formula (5) from a compound of formula (17) with an alcohol of formula (18) and an acid of formula (19), formulas (5) and (17) in which Ro represents:

[0518] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0519] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0520] Ro optionally comprising one to six substituent(s) chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, formulas (5), (18) and (19) in which Ri and Rs independently represent:

[0521] - a linear alkyl group of 1 to 30 carbon atoms, or

[0522] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), said group Ri, optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR? and OCOR?, in which R? is an alkyl group of 1 to 3 carbon atom(s), said group Rs, in addition to the -OH group represented in formula (18), optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR? and OCOR7, provided that at least one of the groups R o , R1 or R5 comprises an alkenyl function and further comprising a step L of preparing a compound of formula (13) from a compound of formula (5).

[0523] Thus the compound of formula (5) comprises at least one additional alkenyl function compared to the compound of formula (13), said function being epoxidized to form said compound of formula (13).

[0524] It is understood that the compound of formula (5) may be a compound already having epoxide functions but that the latter comprises at least one additional alkenyl function compared to the compound of formula (13).

[0525] The additional epoxide function of the compound of formula (13) is located at the same position as the additional alkenyl function of the compound (5). In simpler terms, the compound of formula (13) is derived from an epoxidation of an alkenyl function present in the compound of formula (5).

[0526] This embodiment comprises a step D of esterification on the acid function and on the phenol function of anacardic acid of formula (17) with an alcohol of formula (18) and a carboxylic acid of formula (19) to obtain the compound of formula (5) followed by an epoxidation of at least one alkenyl function of the compound of formula (5).

[0527] Advantageously, epoxidations of several alkenyl functions present in compound (5) can be carried out to obtain compound (13). These epoxidations can be successive or simultaneous.

[0528] It is also possible to isolate compounds with different degrees of epoxidation using methods known to those skilled in the art.

[0529] According to another particular embodiment, the present invention relates to a method as defined above, in which, in the composition comprising the plasticizing agent, the latter is a compound of formula (13), and comprising the following steps:

[0530] • a preparation step D of the compound (5) consisting of: i) a first step of esterification of the compound of formula (17) with a compound (18) to obtain an intermediate compound of formula (3), ii) a second esterification step with a compound of formula (19) to obtain the compound of formula (5), • a preparation step L of the compound of formula (13) consisting of an epoxidation step of the compound of formula (5) to obtain the compound of formula (13)

[0531] • a step of mixing cellulose acetate with a composition comprising at least one cellulose acetate plasticizing agent in a solvent to form a solution, said composition comprising as plasticizing agent said compound of formula (13), to obtain said plastic material in the solvent,

[0532] • a step of evaporating said solvent from said solution to obtain said plastic material.

[0533] By way of non-limiting example, the first step D of esterification i) of anacardic acid, (1 equivalent) with alcohol (in excess) can be carried out in the presence of sulfuric acid in a mixture stirred and heated to reflux under argon for approximately 1 day.

[0534] By way of non-limiting example, the second esterification step D ii) with an acid (1 equivalent) can be carried out in the presence of dimethylamino pyridine (DMAP) and two equivalents of 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC), the mixture obtained being stirred for 4 hours.

[0535] As a non-limiting example, the second esterification step D ii) with an acid (1 equivalent) can be carried out in the presence of one equivalent of propylphosphonic anhydride (T3P) in ethyl acetate at 80°C, for approximately 4 hours.

[0536] As a non-limiting example, the second esterification step D ii) with an acid (1 equivalent) can be carried out in the presence of triethylamine (Et3N) in dichloromethane (DCM) at 0°C, for approximately 18 hours.

[0537] By way of non-limiting example, step L of epoxidation of compound (5) (1 equivalent) is carried out in the presence of formic acid (3 equivalents), sulfuric acid (0.01 equivalent) and hydrogen peroxide (2 equivalents) with stirring and heating at 65°C for approximately 3 hours.

[0538] As a non-limiting example, step L of epoxidation of compound (5) (1 equivalent) is carried out in the presence of 70% metachloroperbenzoic acid (mCPBA) (2 equivalents) in dichloromethane (DCM), mixed cold (0°C) then stirred at room temperature for approximately 18 hours.

[0539] For example, according to the following 3-step reaction scheme:

[0540] Esterification 1 Esterification 2 Epoxidation According to another particular embodiment, the present invention relates to a process as defined above, in which, in the composition comprising the primary plasticizing agent, the latter is a compound of formula (14)

[0541] Roep

[0542] (14) formula (14) in which Ro ep represents:

[0543] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0544] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0545] Roep optionally comprising one to six substituent(s) chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms,

[0546] R4 is chosen from:

[0547] - a hydrogen atom,

[0548] - a methyl CH3 group,

[0549] Riep and Rsep represent independently, in particular which may be identical:

[0550] - a linear alkyl group of 1 to 30 carbon atoms, optionally comprising 1 to 6 epoxide function(s) or

[0551] - a linear alkenyl group of 2 to 24 carbon atoms, optionally comprising 1 to 6 epoxide function(s), said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atom(s),

[0552] Riep and Reep optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, provided that at least one of the Ro groups ep, Riep or Reep comprises at least one epoxide function, and further comprising a step E of preparing the compound of formula (6) from a compound of formula (20) with an acid of formula (21) and an acid of formula (22): formulas (6) and (20) in which R o represent:

[0553] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0554] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0555] Ro optionally comprising one to six substituent(s) chosen from -OH, -OR? or OCOR7, in which R7is an alkyl group of 1 to 3 carbon atoms, R4represents:

[0556] - a hydrogen atom,

[0557] - a methyl group CH3 formulas (6), (21) and (22) in which Ri and Re independently represent:

[0558] - a linear alkyl group of 1 to 30 carbon atoms, or

[0559] - a linear alkenyl group of 2 to 24 carbon atoms, comprising 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), said group R4 optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 and OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s), provided that at least one of the groups R o , Ri or Re comprises an alkenyl function and further comprising a step M of preparing the compound of formula (14) from a compound of formula (6).

[0560] Thus the compound of formula (6) comprises at least one additional alkenyl function compared to the compound of formula (14), said function being epoxidized to form said compound of formula (14).

[0561] It is understood that the compound of formula (6) may be a compound already having epoxide functions but that the latter comprises at least one additional alkenyl function compared to the compound of formula (14).

[0562] The additional epoxide function of the compound of formula (14) is located at the same position as the additional alkenyl function of the compound (6). In simpler terms, the compound of formula (14) is derived from an epoxidation of an alkenyl function present in the compound of formula (6).

[0563] This embodiment comprises a step E of esterification on the two alcohol functions of the compound of formula (20) with two fatty acids of formula (21) and (22) to obtain the diester of formula (6) followed by an epoxidation of at least one alkenyl function of the compound of formula (6).

[0564] Advantageously, epoxidations of several alkenyl functions present in compound (6) can be carried out to obtain compound (14). These epoxidations can be successive or simultaneous.

[0565] It is also possible to isolate compounds with different degrees of epoxidation using methods known to those skilled in the art.

[0566] According to another particular embodiment, the present invention relates to a method as defined above, in which, in the composition comprising the plasticizing agent, the latter is a compound of formula (14), and comprising the following steps:

[0567] • a preparation step E of the compound of formula (6) consisting of an esterification of the compound of formula (20) with an acid of formula (21) and an acid of formula (22), in particular the acids of formulas (21) and (22) are identical, to obtain the compound of formula (6),

[0568] • a preparation step M of the compound of formula (14) consisting of an epoxidation of the compound of formula (6) to obtain the compound of formula (14),

[0569] Roep

[0570] (14)

[0571] • a step of mixing cellulose acetate with a composition comprising at least one cellulose acetate plasticizing agent in a solvent to form a solution, said composition comprising as plasticizing agent said compound of formula (14), to obtain said plastic material in the solvent,

[0572] • a step of evaporating said solvent from said solution to obtain said plastic material.

[0573] As a non-limiting example, the esterification step E of cardol (1 equivalent) with two acids (2 equivalents) can be carried out in the presence of two equivalents of propylphosphonic anhydride (T3P) in ethyl acetate at 80°C, for approximately 4 hours.

[0574] By way of non-limiting example, step M of epoxidation of compound (6) (1 equivalent) is carried out in the presence of formic acid (3 equivalents), sulfuric acid (0.01 equivalent) and hydrogen peroxide (2 equivalents) with stirring and heating at 65°C for approximately 3 hours.

[0575] As a non-limiting example, step M of epoxidation of compound (6) (1 equivalent) is carried out in the presence of 70% metachloroperbenzoic acid (mCPBA) (2 equivalents) in dichloromethane (DCM), mixed cold (0°C) then stirred at room temperature for approximately 18 hours.

[0576] For example according to the following diagram:

[0577] Esterification Epoxidation

[0578] A third subject of the present invention is a plastic material comprising cellulose acetate capable of being obtained by a process according to the invention as defined above.

[0579] A fourth subject of the present invention is a compound of formula (1) formula (1) in which

[0580] • R is chosen from: - a hydrogen atom

[0581] - a CO-R1 group,

[0582] • Ro is chosen from:

[0583] - a linear alkyl group of 15 carbon atoms, optionally comprising 1 to 3 epoxide functions or,

[0584] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0585] • R2 is chosen from:

[0586] - a hydrogen atom,

[0587] - -CO-O-Rs of formula

[0588] O 5

[0589] - a carboxylic acid function COOH

[0590] • R3 are independently chosen from:

[0591] - a hydrogen atom,

[0592] - -OC-O-Re of formula

[0593] - an alcohol OH function,

[0594] • R4 is chosen from:

[0595] - a hydrogen atom,

[0596] - a methyl group CH3,

[0597] • Ri, R5 and Re, identical or different, are chosen from:

[0598] - a linear alkyl group of 2 to 30 carbon atoms, optionally comprising 1 to 6 epoxide function(s), or

[0599] - a linear alkenyl group of 2 to 24 carbon atoms, optionally comprising 1 to 6 epoxide function(s), said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atom(s),

[0600] Ro, Ri, Rs and Re optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR? or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, provided that at least one of the groups OR, R2 or R3 is an ester function and / or at least one of Ro, Ri, Rs or Re comprises at least one epoxide function and provided that when the compound of formula (1) is: then the compound comprises at least one epoxide function, the following compounds being excluded:

[0601]

[0602] According to another particular embodiment, the present invention relates to a compound as defined above, of formula chosen from the following formulas (3), (4), (5) and (6),

[0603] Ro represents:

[0604] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0605] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0606] R4 is chosen from:

[0607] - a hydrogen atom,

[0608] - a methyl group CH3

[0609] Ri, s and Ro are chosen from:

[0610] - a linear alkyl group of 2 to 30 carbon atom(s), or

[0611] - a linear alkenyl group of 2 to 24 carbon atoms, said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atom(s), in particular in which:

[0612] Ro is chosen from:

[0613] said group R o optionally comprising 1 to 6 substituent(s) chosen from -OH, -OR7 and OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s), said groups Ri, R5 and Re optionally comprising 1 to 6 substituent(s), in particular one or two, chosen from -OH, -OR7 and OCOR7.

[0614] According to another particular embodiment, the present invention relates to a compound as defined above, of formula chosen from the following formulas (8) and (9),

[0615] (8) (9)

[0616] Roep represents:

[0617] - a linear alkyl group of 15 carbon atoms comprising from 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 2, comprising y epoxide functions, y varying from 1 to 2, x + y being less than or equal to 3, said group Ro ep optionally comprising 1 to 6 substituent(s) chosen from -OH, -OR? and OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s). in particular in which:

[0618] Roep is chosen from:

[0619] According to another particular embodiment, the present invention relates to a compound as defined above, chosen from the following formulas (10), (11), (12), (13) and (14),

[0620] (13) (14) Roep represents:

[0621] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0622] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0623] R4 is chosen from:

[0624] - a hydrogen atom,

[0625] - a methyl group CH3

[0626] Riep, Rsep and Reep are independently chosen from: o an alkyl group of 2 to 30 carbon atoms, optionally comprising from 1 to 6 epoxide functions, o a linear alkenyl group of 2 to 24 carbon atoms, in particular comprising from 1 to 6 epoxide functions, said alkenyl group being optionally substituted by an alkyl chain of 1 to 5 carbon atoms, provided that at least one of the groups Roep, Riep, Rsep or Rsep comprises at least one epoxide function, in particular in which

[0627] Roep is chosen from: the said Ro group ep optionally comprising 1 to 6 substituent(s) chosen from -OH, -OR? and OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s) said groups Ri ep , Rsep and Roep optionally comprising 1 to 6 substituent(s), in particular one or two, chosen from -OH, -OR7 and OCOR7.

[0628] According to another particular embodiment, the present invention relates to a compound as defined above, chosen from the following formulas (11), (12), (13) and (14),

[0629] Roep represents:

[0630] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0631] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0632] R4 is chosen from:

[0633] - a hydrogen atom,

[0634] - a methyl group CH3

[0635] Riep, Rsep and Reep are independently chosen from: o an alkyl group of 2 to 30 carbon atoms, optionally comprising from 1 to 6 epoxide functions, o a linear alkenyl group of 2 to 24 carbon atoms, in particular comprising from 1 to 6 epoxide functions, said alkenyl group being optionally substituted by an alkyl chain of 1 to 5 carbon atoms, provided that at least one of the R groups Oep , Ri ep , Rsep or Rsep comprises at least one epoxide function, in particular in which

[0636] - Roep is chosen from:

[0637] said group R Oep optionally comprising 1 to 6 substituent(s) chosen from -OH, -OR7 and OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s) said groups Ri ep , Rs ep and R 6ep optionally comprising 1 to 6 substituent(s), in particular one or two, chosen from -OH, -OR7 and OCOR7.

[0638] According to another particular embodiment, the present invention relates to a compound as defined above, of formula (10) formula (2) in which

[0639] • Roep is chosen from:

[0640] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0641] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0642] • Laugh P is chosen from:

[0643] - a linear alkyl group of 3 to 13 or 15 to 30 carbon atom(s), optionally comprising 1 to 6 epoxide function(s), or

[0644] - a linear alkenyl group of 2 to 17 or 19 to 24 carbon atoms, optionally comprising 1 to 6 epoxide function(s), said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atom(s),

[0645] Roep optionally comprising one to six substituent(s) chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms,

[0646] Laugh P optionally comprising one to six substituent(s), in particular one or two chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, provided that Ro e p or Ri ep has at least one epoxy function.

[0647] According to another particular embodiment, the present invention relates to a compound as defined above, of formulas chosen from formulas (2), (3), (4), (5) and (6), in which:

[0648] Ro is chosen from:

[0649] According to another particular embodiment, the present invention relates to a compound as defined above, of formulas chosen from formulas (7), (8) and (9), in which:

[0650] Roep is chosen from:

[0651] According to another particular embodiment, the present invention relates to a compound as defined above, of formulas chosen from formulas (10), (11), (12), (13) and (14), in which:

[0652] Roep is chosen from:

[0653]

[0654] A fifth subject of the present invention is a process for preparing a compound of formula (1) as defined above according to the invention.

[0655] According to another particular embodiment, the present invention relates to a process for preparing a compound of formula (2) as defined above, comprising a step of esterification, for example using 4-dimethylaminopyridine and 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide or propylphosphonic anhydride, of a compound of formula (15) with an acid of formula (16):

[0656] O x HO R,

[0657] (15) (16) formula (15) in which R o represents:

[0658] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0659] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3, formula (16) in which Ri represents:

[0660] - a linear alkyl group of 1 to 30 carbon atoms, or

[0661] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s),

[0662] Ri optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR? or -OCOR?, in which R? is an alkyl group of 1 to 3 carbon atoms, to obtain the compound of formula (2) in which Ro represents: - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0663] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3.

[0664] Ri represents:

[0665] - a linear alkyl group of 1 to 30 carbon atoms, or

[0666] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s),

[0667] Ri optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 or -OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms.

[0668] According to another particular embodiment, the present invention relates to a process for preparing a compound of formula (3) as defined above, comprising a step of esterification, for example using sulfuric acid, of a compound of formula (17) with an alcohol of formula (18) R5OH

[0669] (17) (18) formula (18) in which Ro represents:

[0670] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0671] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3, formula (18) in which Rs represents:

[0672] - a linear alkyl group of 1 to 30 carbon atoms, or

[0673] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s),

[0674] R5 optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR? or OCOR?, in which R? is an alkyl group of 1 to 3 carbon atoms, to obtain the compound of formula (3) in which Ro represents:

[0675] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0676] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0677] Rs represents:

[0678] - a linear alkyl group of 1 to 30 carbon atoms, or - a linear alkenyl group of 2 to 24 carbon atoms, comprising 1 to 6 alkenyl functions, said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atoms,

[0679] R5 optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms.

[0680] According to another particular embodiment, the present invention relates to a process for preparing a compound of formula (4) as defined above, comprising a step of esterification, for example using 4-dimethylaminopyridine and 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide or propylphosphonic anhydride, of a compound of formula (17) with an acid of formula (19),

[0681] (17) (19) formula (17) in which Ro represents:

[0682] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0683] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3. formula (19) in which R represents

[0684] - a linear alkyl group of 1 to 30 carbon atoms, or

[0685] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), said group Ri optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR? and OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s), to obtain the compound of formula (4) in which Ro represents:

[0686] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0687] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3.

[0688] Ri represents

[0689] - a linear alkyl group of 1 to 30 carbon atoms, or

[0690] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), said group Ri optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 and OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s). According to another particular embodiment, the present invention relates to a process for preparing a compound of formula (5) as defined above, comprising a step of esterification of a compound of formula (17) with an alcohol of formula (18) and an acid of formula (19): formula (17) in which Ro represents:

[0691] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0692] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3, formulas (18) and (19) in which Ri and R5 independently represent:

[0693] - a linear alkyl group of 1 to 30 carbon atoms, or

[0694] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), said groups R 1 and R 5, in addition to the -OH group represented in formula (18), optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR 7 and OCOR 7, in which R 7 is an alkyl group of 1 to 3 carbon atom(s), comprising the following steps: i) a first step of esterification, for example using sulfuric acid, of the compound of formula (17) with a compound (18) to obtain a compound of formula (3), formula (3) in which Ro represents:

[0695] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0696] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3.

[0697] Rs represents:

[0698] - a linear alkyl group of 1 to 30 carbon atoms, or

[0699] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), said Rs group optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR? and OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s), ii) a second esterification step, for example using 4-dimethylaminopyridine and 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide or propylphosphonic anhydride, of the compound of formula (3) with a compound of formula (19) to obtain the compound of formula (5), formula (5) in which Ro represents:

[0700] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0701] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0702] Ri and Rs independently represent:

[0703] - a linear alkyl group of 1 to 30 carbon atoms, or

[0704] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), said groups Ri and Rs optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 and OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s).

[0705] According to another particular embodiment, the present invention relates to a process for preparing a compound of formula (6) as defined above, comprising a step of esterification, for example using 4-dimethylaminopyridine and 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide or propylphosphonic anhydride of a compound of formula (20) with an acid of formula (21) and an acid of formula (22): formula (20) in which R o represents:

[0706] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0707] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3, in which R4 represents:

[0708] - a hydrogen atom

[0709] - a methyl group CH3, formulas (21) and (22) in which Ri and Re represent independently, in particular which may be identical:

[0710] - a linear alkyl group of 1 to 30 carbon atoms, or

[0711] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), comprising a step of esterification of the compound of formula (20) with an acid of formula (21) and an acid of formula (22), in particular the fatty acids of formulas (21) and (22) are identical, to obtain the compound of formula (6), said groups Ri and Re optionally comprising one to six, in particular one or two, substituent(s) chosen from -OH, -OR7 and OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s), in which Ro represents:

[0712] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0713] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3, in which R4 represents:

[0714] - a hydrogen atom,

[0715] - a methyl group CH3,

[0716] Ri and Re represent independently, in particular being able to be identical:

[0717] - a linear alkyl group of 1 to 24 carbon atoms, or

[0718] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), said groups Ri and Re optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 and OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s).

[0719] According to another particular embodiment, the present invention relates to a process for preparing a compound of formula (7) as defined above comprising a step of epoxidation of a compound of formula (15) and optionally a step of formation of diol of the compound of formula (7): formula (15) in which R o represents:

[0720] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3, to obtain the compound of formula (7) in which Roep represents:

[0721] - a linear alkyl group of 15 carbon atoms comprising 1 to 3 epoxide functions, or

[0722] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 2, comprising y epoxide functions, y varying from 1 to 2, x + y being less than or equal to 3

[0723] Roep optionally comprising one to six substituent(s) chosen from -OH, -OR? or -OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, comprising the following steps:

[0724] I) a step of epoxidation of a compound of formula (15), for example using formic acid, hydrogen peroxide and sulfuric acid to obtain the compound of formula (7) in which R Oep represents:

[0725] - a linear alkyl group of 15 carbon atoms comprising 1 to 3 epoxide functions, or

[0726] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 2, comprising y epoxide functions, y varying from 1 to 2, x + y being less than or equal to 3 ii) optionally, a step of formation of diol(s), for example using formic acid, hydrogen peroxide and sulfuric acid to obtain the compound of formula (7) in which Ro ep represents:

[0727] - a linear alkyl group of 15 carbon atoms comprising 1 to 3 epoxide functions, or

[0728] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 2, comprising y epoxide functions, y varying from 1 to 2, x + y being less than or equal to 3

[0729] Roep comprising two to six substituent(s) chosen from -OH, -OR7 or -OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms,

[0730] According to another particular embodiment, the present invention relates to a process for preparing a compound of formula (8) as defined above comprising a step of epoxidation of a compound of formula (17) and optionally a step of formation of diol of the compound of formula (8): formula (17) in which Ro represents:

[0731] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3, to obtain the compound of formula (8), formula (8) in which R Oep represents:

[0732] - a linear alkyl group of 15 carbon atoms comprising 1 to 3 epoxide functions, or

[0733] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 2, comprising y epoxide functions, y varying from 1 to 2, x + y being less than or equal to 3.

[0734] Roep optionally comprising one to six substituent(s) chosen from -OH, -OR7 or -OCORz, in which R7 is an alkyl group of 1 to 3 carbon atoms, comprising the following steps: i) a step of epoxidation of a compound of formula (17), for example using formic acid, hydrogen peroxide and sulfuric acid to obtain the compound of formula (8) in which Ro ep represents:

[0735] - a linear alkyl group of 15 carbon atoms comprising 1 to 3 epoxide functions, or

[0736] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 2, comprising y epoxide functions, y varying from 1 to 2, x + y being less than or equal to 3 ii) optionally, a step of forming a diol, for example using formic acid, hydrogen peroxide and sulfuric acid to obtain the compound of formula (8) in which R Oep represents:

[0737] - a linear alkyl group of 15 carbon atoms comprising 1 to 3 epoxide functions, or

[0738] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 2, comprising y epoxide functions, y varying from 1 to 2, x + y being less than or equal to 3

[0739] Roep comprising two to six substituent(s) chosen from -OH, -OR7 or -OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms,

[0740] According to another particular embodiment, the present invention relates to a process for preparing a compound of formula (9) as defined above, comprising a step of epoxidation of a compound of formula (20) and optionally a step of formation of diol of the compound of formula (9): formula (20) in which Ro represents:

[0741] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3, in which R4 represents:

[0742] - a hydrogen atom

[0743] - a methyl group CH3, to obtain the compound of formula (9) in which Roep represents:

[0744] - a linear alkyl group of 15 carbon atoms comprising 1 to 3 epoxide functions, or

[0745] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 2, comprising y epoxide functions, y varying from 1 to 2, x + y being less than or equal to 3,

[0746] Roep optionally comprising one to six substituent(s) chosen from -OH, -OR7 or -OCOR7, i in which R7 is an alkyl group of 1 to 3 carbon atoms, in which R4 represents:

[0747] ;- a hydrogen atom i- a methyl group CH3comprising the following steps: i) a step of epoxidation of a compound of formula (20), for example using formic acid, hydrogen peroxide and sulfuric acid to obtain the compound of formula (9) in which Roep represents:

[0748] - a linear alkyl group of 15 carbon atoms comprising 1 to 3 epoxide functions, or

[0749] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 2, comprising y epoxide functions, y varying from 1 to 2, x + y being less than or equal to 3 in which R4 represents:

[0750] - a hydrogen atom

[0751] - a methyl group CH3 ii) optionally, a step of formation of diol(s), for example using formic acid, hydrogen peroxide and sulfuric acid to obtain the compound of formula (9) in which Roep represents:

[0752] - a linear alkyl group of 15 carbon atoms comprising 1 to 3 epoxide functions, or

[0753] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 2, comprising y epoxide functions, y varying from 1 to 2, x + y being less than or equal to 3

[0754] Roep comprising two to six substituent(s) chosen from -OH, -OR? or -OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, in which R4 represents:

[0755] - a hydrogen atom

[0756] - a methyl group CH3

[0757] According to another particular embodiment, the present invention relates to a process for preparing a compound of formula (10) as defined above, from a compound of formula (15) with an acid of formula (16) to obtain a compound of formula (2), followed by an epoxidation of the compound of formula (2) and optionally a step of forming a diol of the compound of formula (2):

[0758] (15) (16) formula (15) in which R o represents:

[0759] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0760] ; - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0761] Ro optionally comprising one to six substituent(s) chosen from -OH, -OR? or -OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, formula (16) in which Ri represents:

[0762] - a linear alkyl group of 1 to 30 carbon atoms, or

[0763] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl functions, said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atoms,

[0764] Ri optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7and OCOR7, in which R7is an alkyl group of 1 to 3 carbon atom(s), provided that at least one of the groups R0or Ri comprises at least one alkenyl function, comprising the following steps: i) an esterification step, for example using 4-dimethylaminopyridine and 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide or propylphosphonic anhydride of the compound of formula (15) with an acid of formula (16) to obtain a compound of formula (2), formula (2) in which Ro represents:

[0765] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0766] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0767] Ro optionally comprising one to six substituent(s) chosen from -OH, -OR7 or -OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms,; Ri represents:

[0768] - a linear alkyl group of 1 to 30 carbon atoms; or

[0769] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl functions, said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atoms,

[0770] Ri optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 and OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s), ii) a step of epoxidation, for example using formic acid, hydrogen peroxide and sulfuric acid, of the compound of formula (2) to obtain the compound of formula (10)

[0771] O formula (10) in which Roep represents:

[0772] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0773] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0774] Roep optionally comprising one to six substituent(s) chosen from -OH, -OR7, -OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, Riep represents:

[0775] - a linear alkyl group of 1 to 30 carbon atoms, optionally comprising 1 to 6 epoxide function(s), or

[0776] - a linear alkenyl group of 2 to 24 carbon atoms, optionally comprising 1 to 6 epoxide function(s), said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atom(s), said Ri group ep optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 and OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s), provided that at least one of the Ro groups ep or Ri ep comprises at least one epoxide function. iii) optionally, a diol formation step, for example using formic acid, hydrogen peroxide and sulfuric acid to obtain the compound of formula (10) in which R Oep represents:

[0777] - a linear alkyl group of 15 carbon atoms comprising 1 to 3 epoxide functions, or

[0778] - a linear alkenyl group i of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 2, comprising y epoxide functions, y varying from 1 to 2, x + y being less than or equal to 3

[0779] Roep comprising two to six substituent(s) chosen from -OH, -OR7 or -OCOR?, in which Rz is an alkyl group of 1 to 3 carbon atoms, Rie P represents:

[0780] - a linear alkyl group of 1 to 30 carbon atoms, optionally comprising 1 to 6 epoxide function(s), or

[0781] - a linear alkenyl group of 2 to 24 carbon atoms, optionally comprising 1 to 6 epoxide function(s), said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atom(s), said Ri group epoptionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR? and OCOR?, in which R7 is an alkyl group of 1 to 3 carbon atom(s),

[0782] According to another particular embodiment, the present invention relates to a process for the preparation of a compound of formula (11) as above, from a compound of formula (17) with an alcohol of formula (18) to obtain a compound of formula (3) followed by an epoxidation of the compound of formula (3), and optionally a step of forming a diol of the compound of formula (3):

[0783] (17) (18) formula (17) in which Ro represents:

[0784] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0785] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0786] Ro optionally comprising one to six substituent(s) chosen from -OH, -OR7 or -OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, formula (18) in which R5 represents:

[0787] - a linear alkyl group of 1 to 30 carbon atoms, or

[0788] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), said group Rs, in addition to the -OH group represented in formula (18), optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 and OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s), provided that at least one of the groups Ro or Rs comprises at least one alkenyl function, comprising the following steps: i) a first step of esterification, for example using sulfuric acid, of the compound of formula (17) with a compound (18) to obtain a compound of formula formula (3) in which R o represents:

[0789] - a linear alkyl group of 15 carbon atoms optionally comprising from 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0790] Ro optionally comprising one to six substituent(s) chosen from -OH, -OR7 or -OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms,

[0791] ; Rs represents:

[0792] - a linear alkyl group of 1 to 30 carbon atoms, or - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl functions, said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atoms, said Rs groups optionally comprising one to six substituents, in particular one or two, chosen from -OH, -OR? and OCORz, in which R7 is an alkyl group of 1 to 3 carbon atoms, in which at least one of the groups Ro or R5 comprises at least one alkenyl function, ii) a step of epoxidation, for example using formic acid, hydrogen peroxide and sulfuric acid, of the compound of formula (3) to obtain the compound of formula (11) formula (11) in which Ro ep represents:

[0793] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0794] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0795] Roep optionally comprising one to six substituent(s) chosen from -OH, -OR7 or -OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, Rsep represents:

[0796] - a linear alkyl group of 1 to 30 carbon atoms, optionally comprising

[0797] 1 to 6 epoxy function(s), or

[0798] - a linear alkenyl group of 2 to 24 carbon atoms, optionally comprising from 1 to 6 epoxide function(s), said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atom(s), said Rsep group optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 and OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s), provided that at least one of the Roep or Rsep groups comprises at least one epoxide function. iii) optionally, a diol formation step, for example using formic acid, hydrogen peroxide and sulfuric acid to obtain the compound of formula (11) in which Roep represents:

[0799] - a linear alkyl group of 15 carbon atoms comprising 1 to 3 epoxide functions, or

[0800] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 2, comprising y epoxide functions, y varying from 1 to 2, x + y being less than or equal to 3

[0801] Roep comprising two to six substituent(s) chosen from -OH, -OR7 or -OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, Rsep represents:

[0802] - a linear alkyl group of 1 to 30 carbon atoms, optionally comprising 1 to 6 epoxide function(s), or

[0803] - a linear alkenyl group of 2 to 24 carbon atoms, optionally comprising 1 to 6 epoxide function(s), said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atom(s), said Rse group Poptionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 and OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s),

[0804] According to another particular embodiment, the present invention relates to a process for [preparing a compound of formula (12) as defined above, from a compound of formula (17) with an acid of formula (19) to obtain a compound of formula (4) followed by an epoxidation of the compound of formula (4) and optionally a step of forming a diol of a compound of formula (4):

[0805] OH O

[0806] Oh ° H HAS

[0807] HCT ^

[0808] (17) (19) formula (17) in which R o represents:

[0809] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0810] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0811] Ro optionally comprising one to six substituent(s) chosen from -OH, -OR7 or -OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, formula (19) in which Ri represents:

[0812] - a linear alkyl group of 1 to 30 carbon atoms, or

[0813] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), said group Ri optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 and OCOR7, in which R7 is an alkyl group of 1 to 3. carbon atom(s), provided that at least one of the groups Ro or Ri comprises at least one alkenyl function, comprising the following steps of: i) an esterification step, for example using 4-dimethylaminopyridine and 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide or propylphosphonic anhydride of the compound of formula (17) with a compound of formula (19) to obtain the compound of formula (4), formula (4) in which Ro represents: - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0814] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0815] Ro optionally comprising one to six substituent(s) chosen from -OH, -OR? or -OCOR?, in which R? is an alkyl group of 1 to 3 carbon atoms, Ri represents:

[0816] - a linear alkyl group of 1 to 30 carbon atoms, or

[0817] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), said group Ri optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR? and OCOR?, in which R? is an alkyl group of 1 to 3 carbon atom(s), in which at least one of the groups Ro or Ri comprises at least one alkenyl function, ii) an epoxidation step, for example using formic acid, hydrogen peroxide and sulfuric acid, of the compound of formula (4) to obtain the compound of formula (12), formula (12) in which R Oep represents:

[0818] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0819] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0820] Roep optionally comprising one to six substituent(s) chosen from -OH, -OR? or -OCOR?, in which R? is an alkyl group of 1 to 3 carbon atoms, Riep represents:

[0821] - a linear alkyl group of 1 to 30 carbon atoms, optionally comprising 1 to 6 epoxide function(s), or

[0822] - a linear alkenyl group of 2 to 24 carbon atoms, optionally comprising 1 to 6 epoxide function(s), said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atom(s), said Ri group ep optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR? and OCOR?, in which R? is an alkyl group of 1 to 3 carbon atoms, provided that at least one of the groups Roep or R-iep comprises at least one epoxide function. iii) optionally, a diol formation step, for example using formic acid, hydrogen peroxide and sulfuric acid to obtain the compound of formula (12) in which Ro ep represents:

[0823] - a linear alkyl group of 15 carbon atoms comprising 1 to 3 epoxide functions, or

[0824] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 2, comprising y epoxide functions, y varying from 1 to 2, x + y being less than or equal to 3

[0825] Roep comprising two to six substituent(s) chosen from -OH, -OR7 or - OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, Riep represents:

[0826] - a linear alkyl group of 1 to 30 carbon atoms, optionally comprising 1 to 6 epoxidized function(s), or

[0827] - a linear alkenyl group of 2 to 24 carbon atoms, optionally comprising from 1 to 6 epoxide function(s), said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atom(s), said Rsep group optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 and OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s),

[0828] According to another particular embodiment, the present invention relates to a process for preparing a compound of formula (13) as defined above, from a compound of formula (17) with an alcohol of formula (18) and an acid of formula (19) to obtain a compound of formula (5) followed by an epoxidation of the compound of formula (5): 5

[0829] (17) (18) (19) formula (17) in which R o represents:

[0830] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0831] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0832] Ro optionally comprising one to six substituent(s) chosen from -OH, -OR? or -OCOR?, in which R? is an alkyl group of 1 to 3 carbon atoms, formulas (18) and (19) in which Ri and Rs independently represent:

[0833] - a linear alkyl group of 1 to 30 carbon atom(s)^ or

[0834] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), said groups Ri and Rs, in addition to the -OH group represented in formula (18), optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR? and OCOR?, in which R7is an alkyl group of 1 to 3 carbon atoms, provided that at least one of the groups Ro, Ri or R5 comprises at least one alkenyl function, comprising the following steps of: i) a first step of esterification, for example using 4-dimethylaminopyridine and 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide or propylphosphonic anhydride or sulfuric acid, of the compound of formula (17) with a compound (18) and a compound (19) to obtain the compound of formula (5), formula (3) in which Ro represents:

[0835] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0836] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0837] Ro optionally comprising one to six substituent(s) chosen from -OH, -OR? or -OCOR?, in which R? is an alkyl group of 1 to 3 carbon atoms, said groups Ri and Rs optionally comprising one to six substituent(s) chosen from -OH, -OR? and OCOR?, in which R? is an alkyl group of 1 to 3 carbon atoms, provided that at least one of the groups Ro, Ri or R5 comprises at least one alkenyl function, ii) a second step of epoxidation, for example using formic acid, hydrogen peroxide and sulfuric acid, of the compound of formula (5) to obtain the compound of formula (13) formula (13) in which R Oep represents:

[0838] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0839] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0840] Roep optionally comprising one to six substituent(s) chosen from -OH, -OR? or -OCOR?, in which R? is an alkyl group of 1 to 3 carbon atoms, Riep and Rsep independently represent:

[0841] - a linear alkyl group of 1 to 30 carbon atoms, optionally comprising

[0842] 1 to 6 epoxide function(s), or - a linear alkenyl group of 2 to 24 carbon atoms, optionally comprising 1 to 6 epoxide function(s), said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atom(s), said Ri groups ep and Rs ep optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 and OCOR7, provided that at least one of the R groups Oep , Laugh P of Rs ep has an epoxide function. optionally, a diol formation step, for example using formic acid, hydrogen peroxide and sulfuric acid to obtain the compound of formula (13) in which Roep represents:

[0843] - a linear alkyl group of 15 carbon atoms comprising 1 to 3 epoxide functions, or

[0844] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 2, comprising y epoxide functions, y varying from 1 to 2, x + y being less than or equal to 3

[0845] Roep comprising two to six substituent(s) chosen from -OH, -OR7 or - OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, Rie P and R 5ep independently represent:

[0846] - a linear alkyl group of 1 to 30 carbon atoms, optionally comprising 1 to 6 epoxide function(s), or

[0847] - a linear alkenyl group of 2 to 24 carbon atoms, optionally comprising from 1 to 6 epoxide function(s), said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atom(s), said Ri groups ep and Rs epoptionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 and OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s),

[0848] According to another particular embodiment, the present invention relates to a process for preparing a compound of formula (14) as defined above, from a compound of formula (20) with an acid of formula (21) and an acid of formula (22) to obtain a compound of formula (6), followed by an epoxidation of the compound of formula (6) and optionally a step of epoxidation of the compound of formula (6): formula (20) in which R o represents:

[0849] - a linear alkyl group of 15 carbon atoms optionally comprising from 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3, in which R4 represents:

[0850] - a hydrogen atom,

[0851] - a methyl group CH3,

[0852] Ro optionally comprising one to six substituent(s) chosen from -OH, -OR7 or -OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, formulas (21) and (22) in which Ri and Re represent independently, in particular which may be identical:

[0853] - a linear alkyl group of 1 to 30 carbon atoms, or

[0854] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s),

[0855] Ri and Re optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 and OCOR7, provided that at least one of the groups Ro, Ri or Re comprises at least one alkenyl function, comprising the following steps: i) a step of esterification, for example using 4-dimethylaminopyridine and 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide or propylphosphonic anhydride, of the compound of formula (20) with an acid of formula (21) and an acid of formula (22), in particular the fatty acids of formulae (21) and (22) are identical, to obtain the compound of formula (6), formula (6) in which Ro represents:

[0856] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0857] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0858] Ro optionally comprising one to six substituent(s) chosen from -OH, -OR7 or -OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, in which R4 represents:

[0859] - a hydrogen atom

[0860] - a methyl group CH3

[0861] Ri and Re represent independently, in particular being able to be identical:

[0862] - a linear alkyl group of 1 to 30 carbon atoms, or

[0863] - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s),

[0864] Ri and Re optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 and OCOR7, in which one of the groups Ro, Ri or R5 comprises at least one alkenyl function, ii) an epoxidation step, for example using formic acid, hydrogen peroxide and sulfuric acid, of the compound of formula (6) to obtain the compound of formula (14) formula (14) in which R Oep represents:

[0865] - a linear alkyl group of 15 carbon atoms optionally comprising 1 to 3 epoxide functions, or

[0866] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x + y being less than or equal to 3,

[0867] Roep optionally comprising one to six substituent(s) chosen from -OH, -OR7 or -OCOR7, in which R4 represents:

[0868] - a hydrogen atom,

[0869] - a methyl group CH3,

[0870] Laugh P and Reep independently represent, in particular may be identical:

[0871] - a linear alkyl group of 1 to 30 carbon atoms, optionally comprising

[0872] 1 to 6 epoxy function(s), or

[0873] - a linear alkenyl group of 2 to 24 carbon atoms, optionally comprising from 1 to 6 epoxide function(s), said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atom(s), said Ri groups ep and R 6ep optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 and OCOR7, provided that at least one of the Ro groups ep , Riep or Reep comprises an epoxide function, iii) optionally, a diol formation step, for example using formic acid, hydrogen peroxide and sulfuric acid to obtain the compound of formula (13) in which R Oep represents:

[0874] - a linear alkyl group of 15 carbon atoms comprising 1 to 3 epoxide functions, or

[0875] - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 2, comprising y epoxide functions, y varying from 1 to 2, x + y being less than or equal to 3

[0876] Roep comprising two to six substituent(s) chosen from -OH, -OR7 or - OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, Riep and Reep independently represent, in particular may be identical:

[0877] - a linear alkyl group of 1 to 30 carbon atoms, optionally comprising 1 to 6 epoxide function(s), or

[0878] - a linear alkenyl group of 2 to 24 carbon atoms, optionally comprising from 1 to 6 epoxide function(s), said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atom(s), said Ri groups epand Reep optionally comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 and OCOR7, in which R4 represents:

[0879] - a hydrogen atom,

[0880] - a methyl group CH3,

[0881] The following examples and figures illustrate the invention, without limiting its scope.

[0882] Figure 1 represents a plastic film obtained with cellulose acetate and plasticizer P1 b, with the following formula:

[0883] (P1 b)

[0884] EXAMPLES

[0885] Materials and methods

[0886] NMR spectra were performed on a Brüker Avance I 300 MHz instrument. Chemical shifts are counted in parts per million (ppm), where (s) stands for singlet, (d) doublet, (t) triplet, (m) multiplet, and (dd) doublet and doublet. For 1H NMR chemical shifts are measured relative to the residual peak of CDCh at 7.26 ppm.

[0887] Dynamic mechanical analyses were performed on a Metravib DMA 25 device with Dynatest 6.83 software.

[0888] Calorimetric analyses were performed on a Mettler Toledo differential scanning calorimeter. Calorimetric analyses were carried out under nitrogen atmosphere at a rate of 10°C / min.

[0889] The thermal stability of plasticized cellulose acetate was carried out on a TA instruments® Q50 thermogravimetric analyzer device.

[0890] Example 1: Cardanol ester In a flask containing a mixture of cardanol (1 equivalent) and oleic acid (1 equivalent), 0.5 equivalent of dimethylaminopyridine (DMAP) and two equivalents of 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) are added. The mixture was stirred for 4 hours. The reaction was monitored using thin layer chromatography. At the end of the reaction, the solvent was evaporated under vacuum. The residue was dissolved in ethyl acetate and then washed 3 times with water. The product was purified using a silica chromatography column (cyclochexane / ethyl acetate mixture 95 / 5). The crude product P1a of the above formula obtained is a colorless / yellowish oil. The yield is 90%.

[0891] 1H NMR (CDCh), 5 (ppm): 0.81-0.91 (m, (2CH3), 1.2-1.36 (m, CH2), 1.53-1.62 (m, CH2), 1.64-1.75 (t, CH2), 1.93-2.07 (m, CH2), 2.45-2.53 (t, CH2) 2.53-2.61 (t, CH2), 2.71-2.82 (m, CH2), 4.90-5.05 (m, CH2=), 5.24-5.42(m, CH), 5.72-5.86 (m, CH), 6.80-6.87 (m, CH aromatic), 6.99-7.06 (d, CH aromatic), 7, 19-7.27 (dd, aromatic CH).

[0892] 13 C NMR (CDCh), 5 (ppm): 14.3 (CH3), 22.8 (CH2), 25 (CH2), 25.8 (CH2), 27 (CH2), 27.3 (CH2), 29.1-29.9 (CH2), 31.3 (CH2), 32 (CH2), 34.6 (CH2), 35.9 (CH2), 114.8 (CH2=), 118.8 (CH aromatic), 121.5 (CH aromatic), 126 (CH aromatic), 129.2 (CH aromatic), 126.9-137 (CH side alkyl chain), 144.7 (C of alkyl chain), 150.9 (CO), 172.5 (OC=O ester).

[0893] (P1a) (P1b)

[0894] : In a two-necked flask equipped with a dropping funnel, 1 equivalent of P1 a was dissolved in dichloromethane (DCM) (1 ml for 50 mg of P1). 70% metachloroperbenzoic acid (mCPBA) (2 equivalents) was added dropwise at 0°C over 5 minutes. The solution was stirred at 0°C for 1 hour, then at room temperature for 18 hours. At the end of the reaction, the product was washed with saturated aqueous NaHCO3 solution and saturated NaCl solution. The organic phase was dried with MgSO,». The solvent was then removed by evaporation in vacuo. The product P1 b of the above formula obtained is a colorless oil. The yield is 94%.

[0895] 1H NMR (CDCh), 5 (ppm) 0.86-0.96 (m, (2 CH3), 1.22-1.45 (m, CH2), 1.47-1.56 (m, CH2), .1.57-1.68 (m, CH2), 1.70-1.82 (t, CH2), 1.97-2.10 (m, CH2),2.51-2.57 (t, CH2) 2.57-2.64 (t, CH2), 2.79-2.86 (m, CH2), 2.87-2.94 (m,CH2), 2.95-3.00 (m, CH), 3.03-3.18 (CH), 6.86-6.94 (m, aromatic CH), 7.00-7.07 (d, CH aromatic), 7, 14-7, 25 (dd, aromatic CH). 13 C NMR (CDCh), 5 (ppm) 14.2 (CH3), 22.7 (CH2), 25 (CH2), 26.2 (CH2), 26.7 (CH2), 27.2 (CH2), 27.9 (CH2), 29.1-29.7 (CH2), 31.2 (CH2), 31.9 (CH2), 34.5 (CH2), 35.8 (CH2), 54.3-57.3 (epoxide) 118.8 (aromatic CH), 121.5 (aromatic CH), 125.9 (aromatic CH), 129.4 (aromatic CH), 144.6 (C-alkyl chain), 150.8 (CO), 172.3 (OC=O ester).

[0896] Example 2 cardanol ester

[0897] In a flask, a mixture of cardanol (1 equivalent) and acetic acid (1 equivalent) was added to 1 equivalent of propylphosphonic anhydride at 80°C. The reaction was monitored using thin layer chromatography. At the end of the reaction, the solvent was evaporated under vacuum. The residue was dissolved in ethyl acetate and then washed 3 times with water. The crude product P2a of the above formula obtained is a colorless / yellowish oil. The yield is 64%.

[0898] 1 H NMR (CDC), 5 (ppm): 0.82-0.91 (m, (CH3), 1.2-1.35 (m, CH2), 1.52-1.64 (m, CH2), 1.93-2.05 (m, CH2), 2.30 (s, CH3), 2.53-2.60 (t, CH2), 2.71-2.82 (m, CH2), 4.92-5.06 (m, CH2=), 5.24-5.42 (m, CH), 5.71-5.86 (m, CH), 6.84-6.88 (m, CH aromatic), 6.98-7.03 (d, CH aromatic), 7.20-7.23 (dd, CH aromatic)).

[0899] (P2a) (P2b)

[0900] 1 equivalent of P2a, formic acid (3 equivalents) and sulfuric acid (0.01 equivalent) were mixed and heated to 50°C. Hydrogen peroxide (2 equivalents) was added dropwise to the mixture, which was stirred and heated to 65°C for 3 hours. At the end of the reaction, a liquid / liquid extraction step was carried out using water and ethyl acetate. The organic phase was washed three times with water and then dried with MgSC . The solvent was then removed by evaporation in vacuo. The crude product P2b of the above formula was purified by silica column chromatography using a cyclohexane / ethyl acetate 95:5 mixture. The product P2b obtained is a colorless oil. The yield is 96%.

[0901] 1H NMR (CDCI3), Ô (ppm) 0.85-0.93 (m, (CH3), 1.25-1.40 (m, CH2), 1.45-1.56 (m, CH2), 1.57-1.68 (m, CH2), 1.70-1.85 (m, CH2), 2.28 (s, CH3), 2.54-2.64 (t, CH2), 2.78-2.85 (m, CH2), 2.87-2.92 (m, CH2), 2.93—3.01 (m, CH), 3.04-3.20 (m, CH), 6.87-6.94 (m, CH aromatic), 7.01-7.07 (d,CH aromatic), 7.20-7.23 (dd,CH aromatic)

[0902] Example 3 Esterified Cardanol Diol

[0903] 1 equivalent of P2b, formic acid (3 equivalents) and sulfuric acid (0.01 equivalent) were mixed and heated to 50°C. Hydrogen peroxide (2 equivalents) was added dropwise to the mixture, which was stirred and heated to 65°C for 3 hours. At the end of the reaction, a liquid / liquid extraction step was carried out using water and ethyl acetate. The organic phase was washed three times with water, then with a 10% by mass sodium metabisulfite solution in water, then with a saturated NaCl water solution, then was dried with MgSO and filtered. The solvent was then removed by evaporation under vacuum. The crude product P2c corresponds to the product P2b for which all the epoxide functions have been replaced by diols.

[0904] Example 4: Cardanol acrylate ester

[0905] In a flask containing a mixture of cardanol (1 equivalent) and acrylic acid (1 equivalent), 1 equivalent of propylphosphonic anhydride was added at 80°C. The reaction was monitored using thin layer chromatography. At the end of the reaction, the solvent was evaporated under vacuum. The residue was dissolved in ethyl acetate and then washed 3 times with water. The crude product P3a of the above formula obtained is a colorless / yellowish oil. The yield is 45%.

[0906] 1 H NMR (CDCI3), 5 (ppm): 7.31 - 7.26 (m, 1 H), 7.08 - 7.03 (dd' 1 H), 6.97 - 6.91 (m, 2H), 6.63 - 6.56 (ddd, 1 H), 6.36 - 6.27 (m, 1 H), 6.03 - 5.98 (m, 1 H), 5.88 - 5.75 (m, 1 H), 5.48 - 5.28 (m, 1 H), 5.08 - 4.95 (m, 1 H), 2.87 - 2.74 (dt, 2H), 2.64 - 2.57 (m, 2H), 2.09 - 1.96 (dt, 2H), 1.68 - 1 .50 (d, 2H), 1.44 - 1.21 (m, 2H), 0.94 - 0.85 (dt, 3H).

[0907] In a two-necked flask equipped with a dropping funnel, 1 equivalent of P3a was dissolved in dichloromethane (DCM) (1 mL for 50 mg of P1). 70% mCPBA (2 equivalents) was added dropwise at 0°C over 5 minutes. The solution was stirred at 0°C for 1 hour, then at room temperature for 18 hours. At the end of the reaction, the product was washed with saturated aqueous NaHCO3 solution and saturated NaCl solution. The organic phase was dried with MgSC . The solvent was then removed by evaporation under vacuum. The product P3b of the above formula obtained is a colorless oil. The yield is 95%.

[0908] 1 H NMR (CDCl3), 5 (ppm) 7.31 - 7.26 (m, 1 H), 7.10 - 7.05 (d, 1 H), 6.98 - 6.94 (dt, 2H), 6.63 - 6.56 (dd, 1 H), 6.37 - 6.27 (dd, 1 H), 6.03 - 5.98 (ddd, 1 H), 3.24 - 2.88 (m, 2H), 2.88 - 2.78 (m, 2H), 2.69 - 2.53 (m, 2H), 1.96 - 1.68 (m, 2H), 1.67 - 1.56 (m, 2H), 1.56 - 0.95 (m, 2H), 0.94 - 0.81 (m, 3H).

[0909] 13 C NMR (CDCl3), 5 (ppm) 14.2 (CH3), 22.7 (CH2), 25 (CH2), 26.2 (CH2), 26.7 (CH2), 27.2 (CH2), 27.9 (CH2), 29.1-29.7 (CH2), 31.2 (CH2), 31.9 (CH2), 34.5 (CH2), 35.8 (CH2), 54.3-57.3 (epoxide) 118.8 (aromatic CH), 121.5 (aromatic CH), 125.9 (aromatic CH), 129.4 (aromatic CH), 144.6 (C-alkyl chain), 150.8 (CO), 172.3 (OC=O ester).

[0910] Example 5 cardanol methacrylate ester

[0911] In a sealed flask, cardanol (1 equivalent) was dissolved in dry DCM (3 mL per gram of cardanol). Triethylamine was added (1 mL per gram of cardanol) to the mixture. The solution was purged by bubbling dinitrogen for 30 minutes and then the mixture was cooled in an ice bath. Methacrylic acid was purged for 10 minutes by bubbling dinitrogen for 10 minutes, and was added dropwise over 10 minutes (1.7 equivalents). The reaction was mixed for 18 h in an ice bath. The residue was washed 3 times with 0.01 M aqueous NaOH solution and once with deionized water, and then extracted with ethyl acetate. The product was dried with Na2SO4, then filtered, and the solvent was evaporated in vacuo. The crude product P4a of the above formula obtained is a colorless / yellowish oil. The yield is 95%. 1H NMR (CDC), 5 (ppm): 0.92 (m, (m, CH3), 1.21-1.32 (m, CH2), 1.51-1.59 (m, CH2), 1.64-1.75 (t, CH2), 1.93-2.05 (m, CH2+ s, CH3methacrylate), 2.53-2.61 (t, CH2), 2.71-2.82 (m, CH2), 4.95-5.09 (m, CH2=), 5.24-5.42 (m, CH), 5.57 (s, 1 H, methacrylate), 5.75-5.90 (m, CH), 6.17 (s, 1 H, methacrylate proton), 6.75-6.85 (m, aromatic CH), 6.99-7.06 (d, CH; aromatic), 7.24-7.28 (dd, CH aromatic).

[0912] In a two-necked flask equipped with a dropping funnel, 1 equivalent of P4a was dissolved in DCM (1 mL for 50 mg of P1). 70% mCPBA (2 equivalents) was added dropwise at 0°C over 5 minutes. The solution was stirred at 0°C for 1 hour, then at room temperature for 18 hours. At the end of the reaction, the product was washed with saturated aqueous NaHCO3 solution and saturated NaCl solution. The organic phase was dried with MgSO4. The solvent was then removed by evaporation in vacuo. The product P4b of the above formula obtained is a yellow oil. The yield is 91%.

[0913] 1H NMR (CDCI3), 5 (ppm): 0.94 (m, CH3), 1.22-1.40 (m, CH2), 1.47-1.55 (m, CH2), 1.59-1.65 (m, CH2), 1.71-1.82 (t, CH2), 1.97-2.10 (m, CH2+ s, CH3methacrylate), 2.51-2.58 (t, CH2) 2.58-2.66 (t, CH2), 2.79-2.85 (m, CH2), 2.87-2.94 (m,CH2), 2.95-3.01 (m, CH), 3.04-3.16 (CH), 4.97-5.96 (remaining alkenyl functions s, 1 H, methacrylate), 6.18 (s, 1 H, proton of methacrylate), 6.86-6.94 (m, aromatic CH), 7.01-7.09 (d, aromatic CH), 7.22-7.29 (dd, aromatic CH).

[0914] Example 6 epoxidized cardanol

[0915] ■ 1 equivalent of cardanol, formic acid (3 equivalents), and sulfuric acid (0.01 equivalent) were mixed and heated to 50°C. Hydrogen peroxide (2 equivalents) was added dropwise to the mixture, which was stirred and heated at 65°C for 3 hours. At the end of the reaction, a liquid / liquid extraction step was carried out using water and ethyl acetate. The organic phase was washed three times with water and then dried with MgSCu. The solvent was then removed by evaporation in vacuo. The crude product P5 of the above formula was purified by silica column chromatography using a 95:5 cyclohexane / ethyl acetate mixture. The product P5 obtained is a colorless oil. The yield is 91%.

[0916] 1H NMR (CDCI3), 5 (ppm): 0.89-0.91 (m, (CH3), 1.22-1.45 (m, CH2), 1.48-1.54 (m, CH2), 1.57-1.68 (m, CH2), 1.71-1.82 (t, CH2), 1.98-2.09 (m, CH2),2.51-2.57 (t, CH2) 2.56-2.64 (t, CH2), 2.79-2.84 (m, CH2), 2.87-2.93 (m, CH2), 2.95-3.00 (m, CH), 3.03-3.18 (CH), 4.97-5.96 (remaining alkenyl functions), 6.64-6.71 (m, aromatic CH), 6.73-6.81 (d, aromatic CH), 7.09-7.16 (dd, aromatic CH).

[0917] Example 7 Esterification and epoxidation of cardol

[0918] In a flask containing a mixture of cardol (1 equivalent) and acetic acid (2 equivalents), 2 equivalents of propylphosphonic anhydride diluted to 50% in ethyl acetate at 80°C were added. The mixture was stirred for 4 hours. The reaction was monitored using thin layer chromatography. At the end of the reaction, the solvent was evaporated under vacuum. The residue was dissolved in ethyl acetate and then washed 3 times with water. The crude product P6a of the above formula obtained is a colorless / yellowish oil. The yield is 95%.

[0919] 1H RMN (CDCI3), 6 (ppm) : 6,78 (d, J = 2,1 Hz, CH), 6,72 (d, J = 2,1 Hz, CH), 5.99 - 4.96 (m, fonctions alcényles restantes), 5,82 (ddt, J = 17,2, 10,1 , 6,2 Hz, CH), 5,52 - 5,26 (m, CH), 5,14 - 4,92 (m, CH), 2,88 - 2,73 (m, CH2), 2,63 - 2,55 (m, CH2), 2,52 (t, J = 7,5 Hz, CH2), 2,31 (s, CH3) 2,16 - 1 ,95 (m, CH2), 1 ,73 (p, J = 7,5 Hz, CH2), 1 ,60 (t, J = 7.5 Hz, CH2), 1 ,49 - 1 ,18 (m, CH2), 0,94 - 0,86 (m, CH3).

[0920] (P6a) (P6b)

[0921] 1 equivalent of P6a, formic acid (3 equivalents) and sulfuric acid (0.01 equivalent) were mixed and heated to 50°C. Hydrogen peroxide (2 equivalents) was added dropwise to the mixture, which was stirred and heated at 65°C for 3 hours. After the reaction was complete, a liquid / liquid extraction step was carried out using water and ethyl acetate. The organic phase was washed three times with water and then dried with MgSC. The solvent was then removed by evaporation in vacuo. The crude product P6b of the above formula was purified by silica column chromatography using a 95:5 cyclohexane / ethyl acetate mixture. The resulting product P6b is a colorless oil. The yield is 91%.

[0922] 1H RMN (CDCh), 5 (ppm) : 6,78 (d, J = 2.1 Hz, CH), 6,71 (t, J = 2.1 Hz, CH), 3,22 - 3,03 (m, CH), 3,03 - 2,95 (m, CH), 2,90 (dq, J = 6,2, 3,4 Hz, CH2), 2,65 - 2,55 (m, CH2), 2,52 (dd, J = 8.6, 6.4 Hz, CH2), 2,45 - 2,20 (m, CH2), 2,29 (s, CH3) 1 ,80 - 1 ,68 (m, CH2), 1 ,67-1 ,20 (m, CH2), 0,93 - 0,84 (m, CH3).

[0923] Exemple 8 Diol de cardol esterifié

[0924] 1 equivalent of P6b, formic acid (3 equivalents) and sulfuric acid (0.01 equivalent) were mixed and heated to 50°C. Hydrogen peroxide (2 equivalents) was added dropwise to the mixture, which was stirred and heated to 65°C for 3 hours. At the end of the reaction, a liquid / liquid extraction step was carried out using water and ethyl acetate. The organic phase was washed three times with water, then with a 10% by mass sodium metabisulfite solution in water, then with a saturated NaCl water solution, then was dried with MgSO4 and filtered. The solvent was then removed by evaporation under vacuum. The crude product P6c corresponds to the product P6b for which all the epoxide functions have been replaced by diols.

[0925] Example 9 Esterification and epoxidation of cardol

[0926] In a mixture of cardol (1 equivalent) and oleic acid (2 equivalents), 2 equivalents of propylphosphonic anhydride diluted to 50% in ethyl acetate at 80°C were added. The mixture was stirred for 4 hours. The reaction was monitored with thin layer chromatography. At the end of the reaction, the solvent was evaporated under vacuum. The residue was dissolved in ethyl acetate and then washed 3 times with water. The crude product P7a of formula obtained above is a colorless / yellowish oil. The yield is 97%. 1 H NMR (CDCI3), 6 (ppm): 6.78 (d, J = 2.1 Hz, CH), 6.72 (d, J = 2.1 Hz, CH), 5.82 (ddt, J 17.2, 10.1, 6.2 Hz, CH), 5.52 - 5.26 (m, CH), 5.14 - 4.92 (m, CH), 2.88 - 2.73 (m, CH2), 2.63 - 2.55 (m, CH2), 2.52 (t, J = 7.5 Hz, CH2), 2.16 - 1.95 (m, CH2), 1.73 (p, J = 7.5 Hz, CH2), 1.60 (t, J = 7.5 Hz, CH2), 1 .49 - 1.18 (m, CH2), 1.03 - 0.77 (m, 2 CH3).

[0927] HCOOH, H2O2

[0928] H2SO4

[0929] 311, 65°C

[0930] 3 equivalents of P7a, formic acid (1 equivalent) and sulfuric acid (0.01 equivalent) were mixed and heated to 50°C. Hydrogen peroxide (6 equivalents) was added dropwise to the mixture, which was stirred and heated at 65°C for 3 hours. At the end of the reaction, a liquid / liquid extraction step was carried out using water and ethyl acetate. The organic phase was washed three times with water and then dried with MgSO4. The solvent was then removed by evaporation in vacuo. The crude product P7b of the above formula was purified by silica column chromatography using a 95:5 cyclohexane / ethyl acetate mixture. The product P7b obtained is a colorless oil. The yield is 94%.

[0931] 1H RMN (CDCh), 5 (ppm) : 6,78 (d, J = 2,1 Hz, CH), 6,71 (t, J = 2,1 Hz, CH), 5.99 - 4.96 (m, fonctions alcényles restantes), 3,22-3,03 (m, CH), 3,03-2,95 (m, CH), 2,90 (dq, J = 6,2, 3,4 Hz, CH2), 2,65-2,55 (m, CH2), 2,52 (dd, J = 8,6, 6,4 Hz, CH2), 2,45-2,20 (m, CH2), 1 ,80-1 ,6 H8 (m, CH2), 1 ,67 - 1 ,20 (m, CH2), 1 ,03-0,84 (m, 2 CH3).

[0932] Exemple 10 Esterification de l’acide anacardique

[0933] In a two-necked flask with a dropping funnel and a 3Å molecular sieve, a mixture of anacardic acid (1 equivalent) and dry methanol (15 mL per gram of cardanol) was dissolved in sulfuric acid (20 L per 1 mL of MeOH), then stirred and refluxed under argon for 27 h 30 min. At the end of the reaction, the solvent was evaporated in vacuo. The product was then solubilized in ethyl acetate. The organic phase was washed three times with brine and then dried with MgSO4. The solvent was then removed by evaporation in vacuo, and the residue was dissolved in ethanol (96%) (10 mL of ethanol per gram of residue) and HaO (500 μL per gram of residue). Calcium hydroxide was introduced to precipitate the remaining anacardic acid, and then the mixture was stirred for 20 minutes. After filtration, the filtrate was dried with MgSO4 and the solvent was evaporated in vacuo.The product P8a of the above formula obtained is a brown oil. The yield is 72%.

[0934] ' 1 H NMR (CDC), ô (ppm): 11.13 (s, 1 H), 7.33 - 7.25 (dd, 2H), 6.84 (dd, = 8.3, 1.2 Hz, 1 H), 6.72 (dd, J = 7.5, 1.2 Hz, 1 H), 5.88 - 5.75 (m, 1 H), 5.49 - 5.26 (m, 4H), 5.09 - 4.92 (m, 1H), 3.96 (s, 3H), 2.93 - 2.85 (m, 2H), 2.85 - 2.74 (m, 3H), 2.12 - 1.95 (m, 4H), 1.66 (s, 2H), 1 .50-1 .56 (m, 3H), 1.44 - 1.16 (m, 17H), 0.89 (dt, J = 13.1, 7.2 Hz, 3H).

[0935] (P8a) (P8b)

[0936] 1 equivalent of P8a, formic acid (3 equivalents) and sulfuric acid (0.01 equivalent) were mixed and heated to 50°C. Hydrogen peroxide (2 equivalents) was added dropwise to the mixture, which was stirred and heated at 65°C for 3 hours. After the reaction was complete, a liquid / liquid extraction step was carried out using water and ethyl acetate. The organic phase was washed three times with water and then dried with MgSO4. The solvent was then removed by evaporation in vacuo. The crude product P8b of the above formula was purified by silica column chromatography using a cyclohexane / ethyl acetate 95:5 mixture. The product P8b obtained is a colorless oil. The yield is 91%.

[0937] 1H RMN (CDCI3), 5 (ppm) : 11 ,13 (s, 1 H), 7,33 - 7,25 (dd, 2H), 6,84 (dd, = 8,3, 1 ,2 Hz, 1 H), 6,72 (dd, J = 7,5, 1 ,2 Hz, 1 H), 5,88 - 5,75 (m, 1 H), 5,49 - 5,26 (m, 4H), 5,09 - 4,92 (m, 1H), ; 3,96 (s, 3H), 2,93 - 2,85 (m, 2H), 2,85 - 2,74 (m, 3H), 2,12 - 1 ,95 (m, 4H), 1 ,66 (s, 2H), 1 ,50- i 1 ,56 (m, 3H), 1 ,44 - 1 ,16 (m, 17H), 0,89 (dt, J = 13,1 , 7,2 Hz, 3H)

[0938] Exemple 11 Acide anacardique époxyde

[0939] 1 equivalent of anacardic acid, formic acid (3 equivalents) and sulfuric acid (0.01 equivalent) were mixed and heated to 50°C. Hydrogen peroxide (2 equivalents) was added dropwise to the mixture, which was stirred and heated to 65°C for 3 hours. At the end of the reaction, a liquid / liquid extraction step was carried out using water and ethyl acetate. The organic phase was washed three times with water and then dried with MgSO4. The solvent was then removed by evaporation in vacuo. The crude product P9a of the above formula was purified by silica column chromatography using a cyclohexane / ethyl acetate 95:5 mixture. The product P9a obtained is a colorless oil. The yield is 91%.

[0940] 1H RMN (CDCI3), 5 (ppm) : 11 ,13 (s, 1 H), 7,33 - 7,25 (dd, CH), 6,85 (dd, J = 8,3, 1 ,2 Hz, CH), 6,70 (dd, J = 7,5, 1 ,2 Hz, CH), 5,94-4,98 (fonctions alcényles restantes), 3,14 - 3,03 (CH2), 3,01 - 2,6 (m, CH2), 2,93 - 2,86 (m, CH2), 2,86 - 2,75 (m, CH2), 2,12 - 1 ,95 (m, CH2), 1 ,72- 1 ,66 (s, CH2), 1 ,50-1 ,56 (m, CH2), 1 ,41 - 1 ,15 (m, CH2), 0,91-0,85 (m, J = 13.1 , 7.2 Hz, 1 CH3)

[0941] Exemple 12 : Esterification de l’acide anacardique

[0942] In a two-necked flask with a dropping funnel and a 3Å molecular sieve, a mixture of anacardic acid (1 equivalent) and dry ethanol (15 mL per gram of cardanol) was dissolved in sulfuric acid (20 μL per 1 mL of EtOH), then stirred and heated to reflux under argon for 27 h 30 min. At the end of the reaction, the solvent was evaporated in vacuo. The product was then solubilized in ethyl acetate. The organic phase was washed three times with brine and then dried with MgSC . The solvent was then removed by evaporation in vacuo, and the residue was dissolved in ethanol (96%) (at a rate of 10 mL of ethanol per gram of residue) and H2O (500 μL per gram of residue). Calcium hydroxide was introduced to precipitate the remaining anacardic acid, and then the mixture was stirred for 20 minutes. After filtration, the filtrate was dried with MgSC>4 and the solvent was evaporated in vacuo.The product P9a of the above formula obtained is a brown oil. The yield is 56%.

[0943] 1 H NMR (CDCh), 5 (ppm): 7.29 (dd, J = 8.3, 7.5 Hz, 1 H), 6.84 (dd, J = 8.3, 1.2 Hz, 1 H), 6.72 (dd, J = 7.6, 1.3 Hz, 1 H), 5.89 - 5.74 (m, 1 H), 5.50 - 5.28 (m, 5H), 5.11 - 4.93 (m, 1 H), 4.44 (q, J = 7.2 Hz, 1 H), 2.94 - 2.87 (m, 1 H), 2.86 - 2.74 (m, 3H), 2.11 - 1.93 (m, 5H), 1.60 (q, J = 7.6Hz, 4H), 1 .44 (t, J = 7.2 Hz, 1 H), 1.41 - 1.19 (m, 22H), 0.94 - 0.82 (m, 4H).

[0944] (P10a) (P10b)

[0945] 1 equivalent of P10a, formic acid (3 equivalents) and sulfuric acid (0.01 equivalent) were mixed and heated to 50°C. Hydrogen peroxide (2 equivalents) was added dropwise to the mixture, which was stirred and heated at 65°C for 3 hours. At the end of the reaction, a liquid / liquid extraction step was carried out using water and ethyl acetate. The organic phase was washed three times with water and then dried with MgSO4. The solvent was then removed by evaporation in vacuo. The crude product P10b of the above formula was purified by silica column chromatography using a cyclohexane / ethyl acetate 95:5 mixture. The product P10b obtained is a colorless oil. The yield is 91%. 1H RMN (CDCh), 5 (ppm) : 7,29 (dd, J = 8,3, 7,5 Hz, 1 H), 6,82 (dd, J = 8,3, 1 ,2 Hz, 1 H), 6,73 (dd, J = 7,5, 1,2 Hz, 1H), 5.96-4.97 (fonctions alcényles restantes), 4,45 (q, J = 7,2 Hz, 1H), 3,15-3,04 (H), 3,01 -2,94 (m, H), 2,92-2,85 (m, 2H), 2,85-2,76 (m, 3H), 2,12-1,95 (m, 5H), 1,59 (q, J = 7,6 Hz, 4H), 1,45-1,14 (m, 20H), 0,91 (dt, J = 13,1, 7,2 Hz, 3H)

[0946] Exemple 13 Esterification de l’acide anacardique

[0947] In a two-necked flask with a dropping funnel and a 3Å molecular sieve, a mixture of anacardic acid (1 equivalent) and dry methanol (15 mL per gram of cardanol) was dissolved in sulfuric acid (20 μL per 1 mL of MeOH), stirred, and refluxed under argon for 27.5 h. After the reaction was complete, the solvent was evaporated in vacuo. The product was then solubilized in ethyl acetate. The organic phase was washed three times with brine and then dried with MgSCh. The solvent was then removed by evaporation in vacuo, and the residue was dissolved in ethanol (96%) (10 mL of ethanol per gram of residue) and H2O (500 μL per gram of residue). Calcium hydroxide was introduced to precipitate the remaining anacardic acid, and then the mixture was stirred for 20 minutes. After filtration, the filtrate was dried by MgSC and the solvent was evaporated in vacuo.The product P11a of the above formula obtained is a brown oil. The yield is 72%.

[0948] 1 H NMR (CDCh), 5 (ppm): 11.13 (s, 1H), 7.33-7.25 (dd, 2H), 6.84 (dd, J = 8.3, 1.2 Hz, 1H), 6.72 (dd, J = 7.5, 1.2 Hz, 1 H), 5.88 - 5.75 (m, 1 H), 5.49 - 5.26 (m, 4H), 5.09 - 4.92 (m, 1H), 3.96 (s, 3H), 2.93 - 2.85 (m, 2H), 2.85 - 2.74 (m, 3H), 2.12 - 1.95 (m, 4H), 1.66 (s, 2H), 1 .50-1.56 (m, 3H), 1.44-1.16 (m, 17H), 0.89 (dt, J = 13.1.7.2 Hz, 3H).

[0949] (P11a) (P11b)

[0950] In a mixture of P11a (1 equivalent) and oleic acid (1 equivalent), 1 equivalent of propylphosphonic anhydride diluted to 50% in ethyl acetate at 80°C was added. The mixture was stirred for 4 hours. The reaction was monitored using thin layer chromatography. At the end of the reaction, the solvent was evaporated under vacuum. The residue was dissolved in ethyl acetate and then washed 3 times with water. The crude product P11b of the above formula obtained is a colorless oil. The yield is 85%.

[0951] 1 H NMR (CDCh), 5 (ppm): 11.13 (s, 1H), 7.41 -7.37 (dd, CH), 7.18-7.15 (dd, J = 8.3, 1.2 Hz, CH), 7.01-6.98 (dd, J =7.5, 1.2 Hz, CH), 5.88-5.75 (m, CH), 5.49-5.26 (m, CH), 5.09-4.92 (m, CH), 3.96 (s, CH3), 2.93 - 2.85 (m, CH2), 2.85 - 2.74 (m, CH2), 2.12-1.95 (m, CH2), 1.72-1.66 (s, CH2), 1.50-1.56 (m, CH2), 1.44-1.16 (m, CH2), 0.83-0.92 (m, J = 13.1, 7.2 Hz, 2 CH3).

[0952] (P11b) (P11c)

[0953] 1 equivalent of P11 b, formic acid (3 equivalents) and sulfuric acid (0.01 equivalent) were mixed and heated to 50°C. Hydrogen peroxide (2 equivalents) was added dropwise to the mixture, which was stirred and heated at 65°C for 3 hours. At the end of the reaction, a liquid / liquid extraction step was carried out using water and ethyl acetate. The organic phase was washed three times with water and then dried with MgSO4. The solvent was then removed by evaporation in vacuo. The crude product P11c of the above formula was purified by silica column chromatography using a cyclohexane / ethyl acetate 95:5 mixture. The product P11c obtained is a colorless oil. The yield is 85%.

[0954] 1H RMN (CDC ), 6 (ppm) : 11 ,13 (s, 1 H), 7,40 - 7,37 (dd, CH), 7,18-7,14 (dd, J = 8,3, 1 ,2 Hz, CH), 7,00-6,98 (dd, J = 7,5, 1 ,2 Hz, CH), 5,96-4,97 (fonctions alcényles restantes), 3,96 (s, CH3), 3,14 - 3,03 (CH2), 3,02 - 2,6 (m, CH2), 2,93 - 2,85 (m, CH2), 2,85 - 2,74 (m, CH2), 2,12 - 1 ,95 (m, CH2), 1 ,72-1 ,66 (s, CH2), 1 ,50-1 ,56 (m, CH2), 1 ,44 - 1 ,16 (m, CH2), 0,83-0,92 (m, J = 13,1 , 7,2 Hz, 2 CH3)

[0955] Exemple 14 Esterification de l’acide anacardique

[0956] In a two-necked flask with a dropping funnel and a 3A molecular sieve, a mixture of anacardic acid (1 equivalent) and dry methanol (15 mL per gram of cardanol) was dissolved in sulfuric acid (20 μL per 1 mL of MeOH), stirred, and refluxed under argon for 27.5 hours. At the end of the reaction, the solvent was evaporated under vacuum. The product was then solubilized in ethyl acetate. The organic phase was washed three times with brine and then dried with MgSO4. The solvent was then removed by evaporation under vacuum, and the residue was dissolved in ethanol (96%) (10 mL of ethanol per gram of residue) and H2O (500 μL per gram of residue). Calcium hydroxide was introduced to precipitate the remaining anacardic acid, and then the mixture was stirred for 20 minutes. After filtration, the filtrate was dried with MgSO4 and the solvent was evaporated in vacuo.The product P12a of the above formula obtained is a brown oil. The yield is 72%. 1 H NMR (CDCh), 5 (ppm): 11.13 (s, 1 H), 7.33 - 7.25 (dd, 2H), 6.84 (dd, J = 8.3, 1.2 Hz, 1 H), 6.72 (dd, J = 7.5, 1.2 Hz, 1 H), 5.88 - 5.75 (m, 1 H), 5.49 - 5.26 (m, 4H), 5.09 - 4.92 (m, 1 H), 3.96 (s, 3H), 2.93 - 2.85 (m, 2H), 2.85 - 2.74 (m, 3H), 2.12 - 1.95 (m, 4H), 1.66 (s, 2H), 1.50-1 .56 (m, 3H), 1.44 - 1.16 (m, 17H), 0.89 (dt, J = 13.1, 7.2 Hz, 3H).

[0957] (P12a) (P12b)

[0958] In a mixture of P12a (1 equivalent) and acetic acid (1 equivalent), 1 equivalent of propylphosphonic anhydride diluted to 50% in ethyl acetate at 80°C is added. The mixture was stirred for 4 hours. The reaction was monitored using thin layer chromatography. At the end of the reaction, the solvent was evaporated under vacuum. The residue was dissolved in ethyl acetate and then washed 3 times with water. The crude product P12b of the above formula obtained is a colorless / yellowish oil. The yield is 89%.

[0959] 1 H NMR (CDCh), 5 (ppm): 11.13 (s, 1 H), 7.40 - 7.37 (dd, CH), 7.18-7.15 (dd, J = 8.3, 1.2 Hz, CH), 7.01 -6.98 (dd, J = 7.5, 1.2 Hz, CH), 5.88 - 5.75 (m, CH), 5.49 - 5.26 (m, CH), 5.09 - 4.92 (m, CH), 3.96 (s, CH3), 2.93 - 2.85 (m, CH2), 2.85 - 2.74 (m, CH2), 2.30 (s, CH3), 2.12 - 1.95 (m, CH2), 1 .72-1.66 (s, CH2), 1.50-1.56 (m, CH2), 1.44 - 1.16 (m, CH2), 0.89-0.92 (m, J = 13.1, 7.2 Hz, 1 CH3).

[0960] (P12b) (P12c)

[0961] 1 equivalent of P12b, formic acid (3 equivalents) and sulfuric acid (0.01 equivalent) were mixed and heated to 50°C. Hydrogen peroxide (2 equivalents) was added dropwise to the mixture, which was stirred and heated to 65°C for 3 hours. At the end of the reaction, a liquid / liquid extraction step was carried out using water and ethyl acetate. The organic phase was washed three times with water and then dried with MgSC . The solvent was then removed by evaporation in vacuo. The crude product P12c of the above formula is purified by silica column chromatography using a cyclohexane / ethyl acetate 95:5 mixture. The product P12c obtained is a colorless / yellowish oil. The yield is 87%.

[0962] 1H NMR (CDCh), ô (ppm): 11.13 (s, 1 H), 7.41 - 7.38 (dd, CH), 7.18-7.16 (dd, J = 8.3, 1.2 Hz, CH), 7.01-6.99 (dd, J = 7.5, 1.2 Hz, CH), 5.96-4.97 (function remaining alkenyl), 3.96 (s, CH3), 3.14 - 3.03 (CH2), 3.02 - 2.6 (m, CH2), 2.93 - 2.85 (m, CH2), 2.85 - 2.74 (m, CH2), 2.29 (s, CH3), 2.12 - 1.95 (m, CH2), 1 .72-1.66 (s, CH2), 1.50-1.56 (m, CH2), 1.44 - 1.16 (m, CH2), 0.91- 0.88 (m, J = 13.1, 7.2 Hz, 1 CH3)

[0963] Example 15: Extrusion protocol

[0964] Cellulose acetate and plasticizer are mixed in an extruder. The plasticizer weight is at a concentration rate of 25 to 32%. The extruder (twin screw (22)) is started at 150-190°C, at a rotation speed of 160 RPM.

[0965] Example 16: Preparation of the plasticized cellulose acetate solution and the plastic film

[0966] The cellulose acetate used has a degree of substitution of 2.5.

[0967] A mixture of plasticizer (30% wt) and cellulose acetate was dissolved at 10% in acetone. The solutions were t mixed for 24 hours at 25°C at atmospheric pressure and then poured onto a Teflon or silicone tray. The films were made by slow evaporation of the solvent at 25°C and atmospheric pressure and stored in a desiccator or oven.

[0968] Thermogravimetric analysis

[0969] The experiments consist of measuring the mass loss of the sample under an air flow (e0mL.min -1 ) depending on the temperature from 25 up to 500°C with a heating rate of 10°C. min -1 .

[0970] Dynamic mechanical analysis

[0971] The specimens were tested under uniaxial tension during heating at a rate of 3 °C / min at a frequency of 1 Hz with a fixed stress of 2.1.10' 6m for samples plasticized with diethylphthalate and 3.6.10" 6 m for samples plasticized with the plasticizers of the invention.

[0972] The tested samples have a thickness of 0.1 mm, 10 mm in width and 20 mm in length.

[0973] Example 17 Plastic film with P1a

[0974] The preparation of the plastic film with plasticizer P1 aa was carried out according to example 14. The results are as follows.

[0975] Differential scanning calorimetry showed a glass transition temperature of 192°C.

[0976] Example 18 Plastic film with P1b

[0977] The preparation of the plastic film with plasticizer P1 b was carried out according to example 14. The results are as follows.

[0978] The glass transition temperature obtained by dynamic mechanical analysis is 128°C. Differential scanning calorimetry showed a glass transition temperature of 171 9 C. Thermogravimetric analyses showed that there was no loss of thermal stability for the plastic.

[0979] The temperature for loss of 5% of the film mass is 311 °C. The onset temperature for film degradation is 350 °C. The degradation temperature of the entire plastic film is 371 °C.

[0980] Example 19 Plastic film with P5

[0981] : The preparation of the plastic film with the plasticizer P5 was carried out according to example 14. The results are as follows.

[0982] Differential scanning calorimetry showed a glass transition temperature of 178°C.

[0983] Example 20 Plastic film with cardol

[0984] The preparation of the plastic film with cardol was carried out according to example 14. The results are as follows.

[0985] Dynamic mechanical analysis showed a glass transition temperature of 114°C.

[0986] The 5% mass loss temperature of the film is 311°C. The onset temperature for film degradation is 409°C.

[0987] The degradation temperature of the entire plastic film is 425°C.

[0988] Example 21 Plastic film with P6a

[0989] The preparation of the plastic film with the plasticizer P6a was carried out according to Example 14. The results are as follows.

[0990] Dynamic mechanical analysis showed a glass transition temperature of 183°C.

[0991] Example 22 Plastic film with P6c

[0992] The preparation of the plastic film with the plasticizer Cardol C2 diol was carried out according to Example 14. The results are as follows.

[0993] Dynamic mechanical analysis showed a glass transition temperature of 165°C.

[0994] The 5% degradation temperature of the film is 247°C.

[0995] The degradation temperature of the entire plastic film is 430°C.

[0996] Example 23 Plastic film with P2a

[0997] The preparation of the plastic film with plasticizer P2a was carried out according to Example 14. The results are as follows.

[0998] Dynamic mechanical analysis showed a glass transition temperature of 171°C.

[0999] The 5% mass loss temperature of the film is 244°C. The onset temperature for film degradation is 344°C.

[1000] The degradation temperature of the entire plastic film is 378°C.

[1001] Example 24 Plastic film with P2b The preparation of the plastic film with the plasticizer P2b was carried out according to Example 14. The results are as follows.

[1002] Dynamic mechanical analysis showed a glass transition temperature of 191°C.

[1003] Example 25 Plastic film with P2c

[1004] The preparation of the plastic film with the plasticizer Cardanol C2 diols was carried out according to Example 14. The results are as follows.

[1005] Dynamic mechanical analysis showed a glass transition temperature of 164°C.

Claims

DEMANDS 1. Use of a composition comprising at least one CNSL-derived compound which includes at least one ester function and / or at least one epoxide function, as a plasticizing agent for cellulose acetate, for the preparation of a plastic material comprising or consisting of cellulose acetate.

2. Use according to claim 1 of a composition comprising at least one CNSL-derived compound which includes at least one ester function and / or at least one epoxide function, as a primary plasticizing agent for cellulose acetate, for the preparation of a plastic material comprising or consisting of cellulose acetate.

3. Use of a composition according to claim 1 or 2 comprising at least one compound of formula (1) as a primary plasticizing agent of cellulose acetate for the preparation of a plastic material comprising or consisting of cellulose acetate, formula (1) in which • R is chosen from: - a hydrogen atom or - a CO-R1 group, • Ro is chosen from: - a linear alkyl group of 15 carbon atoms, possibly comprising 1 to 3 epoxide functions or, - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3, • R2 is chosen from: - a hydrogen atom, -a carboxylic acid function COOH, formula • R3 is chosen from: - a hydrogen atom, - an alcohol functional group -OH formula • R4 is chosen from: - a hydrogen atom or - a methyl group CH3; • Ri, R5 and Re, which are identical or different, are chosen from: - a linear alkyl group of 1 to 30 carbon atom(s), possibly containing 1 to 6 epoxide functions, or - a linear alkenyl group of 2 to 24 carbon atom(s), possibly comprising 1 to 6 epoxide function(s), said alkenyl group possibly being substituted by an alkyl group of 1 to 5 carbon atom(s), Ro, Ri, Rs and Rs possibly comprising one to six substituent(s) selected from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, provided that at least one of the OR, R2 or R3 groups is an ester function and / or at least one of Ro, Ri, Rs or Re has at least one epoxide function or at least one of the compounds of the following formulas:

4. Use of a composition according to any one of claims 1 to 3 comprising at least one compound of formula (1) as a primary plasticizing agent of cellulose acetate for the preparation of a plastic material comprising or consisting of cellulose acetate, formula (1) in which • R is chosen from: - a hydrogen atom or - a CO-R1 group, • Ro is chosen from: - a linear alkyl group of 15 carbon atoms, possibly comprising 1 to 3 epoxide functions or, - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3, • R2 is chosen from: - a hydrogen atom, -a carboxylic acid function COOH, - -CO-O-R5 formula • Rs is chosen from: - a hydrogen atom, - an alcohol functional group -OH formula • R4 is chosen from: - a hydrogen atom or - a methyl group CH3; • Ri, Rs and R6, identical or different, are chosen from: - a linear alkyl group of 1 to 30 carbon atom(s), possibly containing 1 to 6 epoxide functions, or - a linear alkenyl group of 2 to 24 carbon atom(s), possibly comprising 1 to 6 epoxide function(s), said alkenyl group possibly being substituted by an alkyl group of 1 to 5 carbon atom(s), Ro possibly comprising one to six substituent(s) chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, Ri, Rs and R6 possibly comprising one or two substituent(s) chosen from -OH, -OR7 or OCOR7, provided that at least one of the OR, R2 or R3 groups is an ester function and / or at least one of Ro, Ri, Rs or Re has at least one epoxide function or at least one of the compounds with the following formulas:

5. Use of a composition according to any one of claims 1 to 4 comprising at least one compound of formula (1) as a primary plasticizing agent of cellulose acetate for the preparation of a plastic material comprising or consisting of cellulose acetate, formula (1) in which • R is chosen from: - a hydrogen atom or - a CO-R1 group, • Ro is chosen from: - a linear alkyl group of 15 carbon atoms, possibly comprising 1 to 3 epoxide functions or, - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3, • R2 is chosen from: - a hydrogen atom, -a carboxylic acid function COOH, formula • R3 is chosen from: - a hydrogen atom, - an alcohol functional group -OH formula • R4 is chosen from: - a hydrogen atom or - a methyl group CH3; • Ri, R5 and R6, identical or different, are chosen from: - a linear alkyl group of 1 to 30 carbon atom(s), possibly containing 1 to 6 epoxide functions, or - a linear alkenyl group of 2 to 24 carbon atom(s), possibly comprising 1 to 6 epoxide function(s), said alkenyl group possibly being substituted by an alkyl group of 1 to 5 carbon atom(s), Ri, R5 and Re possibly comprising one or two substituents chosen from -OH, -OR? or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, provided that at least one of the OR, R2 or R3 groups is an ester function and / or at least one of R o , Ri, Rs or R6 contains at least one epoxide function or at least one of the compounds with the following formulas:

6. Use of a composition according to any one of claims 1 to 5, comprising at least one compound of formula (1b), as a primary plasticizing agent of cellulose acetate for the preparation of a plastic material comprising or consisting of cellulose acetate, formula (1 b) in which • R is chosen from: - a hydrogen atom - a CO-R1 group, • Ro is chosen from: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3. • R2 is chosen from: - a hydrogen atom, - a carboxylic acid function COOH, or - -CO-O-R5 formula • R3 is chosen from: - a hydrogen atom, - an alcohol OH function, or - -OC-O-Re formula • R4 is chosen from: - a hydrogen atom, - a methyl group CH3, • Ri, R5 and Re, which are identical or different, are chosen from: - a linear alkyl group of 1 to 30 carbon atom(s), or - a linear alkenyl group of 2 to 24 carbon atoms, comprising 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), Ro possibly comprising one to six substituent(s) chosen from -OH, -OR? or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, Ri, R5 and Re possibly comprising one to six substituent(s), in particular one or two, selected from -OH, -OR7 or OCOR7, provided that at least one of the OR, R2 or R3 groups is an ester function; or comprising at least one compound of formula (1c), as a primary plasticizing agent of cellulose acetate for the preparation of a plastic material comprising or consisting of cellulose acetate, formula (1c) in which • Roep is chosen from among: - a linear alkyl group of 15 carbon atoms containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 2, comprising y epoxide functions, y ranging from 1 to 2, x + y being less than or equal to 3, Roep possibly comprising one to six substituent(s) chosen from -OH, OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms • R2 is chosen from: - a hydrogen atom, - a carboxylic acid function COOH, • R3 is chosen from: - a hydrogen atom, - an alcohol functional group (OH), • R4 is chosen from: - a hydrogen atom, - a methyl group CH3; or comprising at least one compound of formula (1d), as a primary plasticizing agent of cellulose acetate for the preparation of a plastic material comprising or consisting of cellulose acetate, formula (1d) in which: • R is chosen from: - a hydrogen atom - a CO-R1 group, • Roep is chosen from among: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, possibly comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3, • R2 is chosen from: - a hydrogen atom, - a carboxylic acid function COOH, or formula • R3 is chosen from: - a hydrogen atom, - an alcohol functional group (OH), or formula • R4 is chosen from: - a hydrogen atom, - a methyl group CH3, • Ri, R5 and Re, identical or different, are chosen from: - a linear alkyl group of 1 to 30 carbon atoms, possibly containing 1 to 6 epoxide functions, or - a linear alkenyl group of 2 to 24 carbon atoms, possibly comprising 1 to 6 epoxide function(s), said alkenyl group possibly being substituted by an alkyl group of 1 to 5 carbon atom(s), Roep possibly comprising one to six substituent(s) chosen from -OH, -OR? or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, Ri, R5 and Re possibly comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 or OCOR7, provided that at least one of the OR, R2 or R3 groups is an ester function and at least one of the Ro groups ep , Ri, Rs or R6 includes at least one epoxide function.

7. Use according to any one of claims 3 to 5, wherein the compound has formula (1b) and is selected from the following compounds with formulas (2), (3), (4), (5) and (6), in which Ro is chosen from: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3, R4 is chosen from: - a hydrogen atom, - a methyl group CH3 Ri, R5 and Re are chosen from: - a linear alkyl group of 1 to 30 carbon atom(s), or - a linear alkenyl group of 2 to 24 carbon atoms, said alkenyl group optionally being substituted by an alkyl group of 1 to 5 carbon atom(s), said group R o comprising optionally one to six substituent(s) selected from -OH, -OR7 or OCOR7, wherein R7 is an alkyl group of 1 to 3 carbon atom(s), said groups Ri, R5 and Re comprising optionally one to six substituent(s), in particular one or two, selected from -OH, -OR7 or OCOR7, or wherein the compound has formula (1c) and is selected from the compounds of the following formulas (7), (8), and (9), in which Roep is chosen from: - a linear alkylated group of 15 carbon atoms comprising 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 2, comprising y epoxide functions, y ranging from 1 to 2, x + y being less than or equal to 3; Roep possibly comprising one to six substituent(s) chosen from -OH, OR? or OCOR?, wherein R7 is an alkyl group of 1 to 3 carbon atoms or wherein the compound is of formula (1d) and is chosen from compounds of formulas (13) (14) • in which Roep is chosen from: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3, • R4 is chosen from: - a hydrogen atom, or - a methyl group CH3, • Riep, Rsep and Reep are chosen from: - a linear alkyl group of 1 to 30 carbon atoms, possibly containing 1 to 6 epoxide functions, or - a linear alkenyl group of 2 to 24 carbon atoms, optionally comprising 1 to 6 epoxide function(s), said alkenyl group optionally being substituted by an alkyl group of 1 to 5 carbon atom(s), said Ro group ep comprising possibly one to six substituent(s) selected from -OH, -OR? or OCOR7, in which R? is an alkyl group of 1 to 3 carbon atom(s), said Ri groups ep , Rsep and Rsep possibly comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR? or OCOR7, provided that at least one of the Roep, Riep, Rsep or Roep groups has at least one epoxide function.

8. Use according to any one of claims 3 to 7, wherein the compound has formula (1b) and is selected from compounds of formulas (2), (3), (4), (5) and (6) in which: Ro is chosen from among: - Ri, R5 and Re are chosen independently of each other from: o an alkyl group of 1 to 30 carbon atom(s), o a linear alkenyl group, of 2 to 24 carbon atoms, said alkenyl group being possibly substituted by an alkyl chain of 1 to 5 carbon atom(s) said Ro group possibly comprising one to six substituent(s) chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s), said Ri, R5 and Re groups possibly comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 or OCOR7, provided that at least one of the OR, R2 or R3 groups is an ester function; or in which the compound has formula (1c) and is chosen from compounds of formulas (7), (8) and (9), in which: Roep is chosen from among: said Roep groups possibly comprising 1 to 6 substituent(s) selected from -OH, -OR7 and OCOR7 or wherein the compound has formula (1d) and is selected from compounds of formulas (10), (11), (12), (13) or (14) in which: Roep is chosen from among: Riep, Rsep, and Reep are chosen independently of each other from: an alkyl group of 1 to 30 carbon atoms, or a linear alkenyl group of 2 to 24 carbon atoms, in particular comprising 1 to 6 epoxide functions, said alkenyl group optionally being substituted by an alkyl chain of 1 to 5 carbon atoms, said group R Oepcomprising optionally one to six substituent(s) selected from -OH, -OR7 or OCOR7, wherein R7 is an alkyl group of 1 to 3 carbon atoms, said groups Riep, Rsep and Reep comprising optionally one to six substituent(s), in particular one or two, selected from -OH, -OR7 or OCOR7, provided that at least one of the groups R Oep , Riep, Rsep or R 6ep includes at least one epoxide function.

9. Use according to any one of claims 3 to 8, wherein the compound of formula (1) is selected from the compounds of the following formulas: ʼnll 10. A method for preparing a plastic material comprising or consisting of cellulose acetate, comprising a step of mixing cellulose acetate with a composition comprising at least one primary plasticizing agent of cellulose acetate, in an extruder, said composition comprising as a primary plasticizing agent at least one CNSL-derived compound according to any one of claims 1 or 2 or at least one compound of formula (1) as defined in any one of claims 3 to 9, to obtain said plastic material.

11. A process for preparing a plastic material comprising or consisting of cellulose acetate, comprising a step of mixing cellulose acetate with a composition comprising at least one primary plasticizing agent of cellulose acetate, in a solvent, to form a solution, said composition comprising as a primary plasticizing agent at least one compound derived from CNSL according to any one of claims 1 or 2, at least one compound of formula (1) as defined in any one of claims 3 to 9, to obtain said plastic material in the solvent, optionally further comprising a step of evaporating said solvent from said solution, to obtain said plastic material, and / or in which, the total quantity by weight of cellulose acetate and primary plasticizing agent represents from 1 to 50% of the solution by weight, in particular from 10 to 30, preferably 10%;and / or in which the ratio between the quantity of primary plasticizing agent by weight and cellulose acetate by weight varies from 1 to 50% by weight, in particular from 10 to 30%, preferably about 30%.

12. A method according to any one of claims 10 or 11, wherein, in the composition comprising the primary plasticizing agent, the latter is a compound of formula (2) formula (2) in which Ro represents: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3. Formula (2) in which Ri represents: - a linear alkyl group of 1 to 30 carbon atom(s), or - a linear alkenyl group of 2 to 24 carbon atoms, comprising 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), Ri possibly comprising one to six substituent(s), in particular one or two, selected from -OH, -OR? or OCOR?, wherein R? is an alkyl group of 1 to 3 carbon atoms Ro possibly comprising one to six substituent(s) selected from -OH, -OR? or OCOR? and further comprising a step A of preparing said compound of formula (2) from a compound of formula (15) with an acid of formula (16): (15) (16) formula (15) in which Ro represents: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3, formula (16) in which Ri represents: - a linear alkyl group of 1 to 30 carbon atom(s), or - a linear alkenyl group of 2 to 24 carbon atom(s), comprising 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), Ri possibly comprising one to six substituent(s), in particular one or two, selected from -OH, -OR? or OCOR?, in which R? is an alkyl group of 1 to 3 carbon atoms Ro possibly comprising one to six substituent(s) selected from -OH, -OR? or OCOR?.

13. A method according to any one of claims 10 or 11, wherein, in the composition comprising the primary plasticizing agent, the latter is a compound of formula (3) formula (3) in which Ro represents: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3, formula (3) in which Rs represents: - a linear alkyl group of 1 to 30 carbon atom(s), or - a linear alkenyl group of 2 to 24 carbon atoms, comprising 1 to 6 alkenyl function(s), possibly branched by a linear alkyl group of 1 to 5 carbon atom(s), Rs possibly comprising one to six substituent(s), in particular one or two, selected from -OH, -OR? or OCOR?, wherein R? is an alkyl group of 1 to 3 carbon atoms Ro possibly comprising one to six substituent(s) selected from -OH, -OR? or OCOR?, and further comprising a step B of preparing a compound of formula (3) from a compound of formula (17) and an alcohol of formula (18) (17) (18) formula (17) in which Ro represents: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3, formula (18) in which Rs represents: - a linear alkyl group of 1 to 30 carbon atom(s), or - a linear alkenyl group of 2 to 24 carbon atoms, comprising 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), Rs, in addition to the -OH group represented in formula (18), possibly comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms Ro possibly comprising one to six substituent(s) selected from -OH, -OR7 or OCOR7, or wherein, in the composition comprising the primary plasticizer, the latter is a compound of formula (4) formula (4) in which Ro represents: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3, formula (4) in which Ri represents: - a linear alkyl group of 1 to 30 carbon atom(s), or - a linear alkenyl group of 2 to 24 carbon atoms, comprising 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), Ri possibly comprising one to six substituent(s), in particular one or two, selected from -OH, -OR7 or OCOR7, wherein R7 is an alkyl group of 1 to 3 carbon atoms Ro possibly comprising one to six substituent(s) selected from -OH, -OR7 or OCOR7, and further comprising a step C of preparing a compound of formula (4) from a compound of formula (17) and an acid of formula (19): (17) (19) formula (17) in which Ro represents: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3, formula (19) in which Ri represents: - a linear alkyl group of 1 to 30 carbon atom(s), or - a linear alkenyl group of 2 to 24 carbon atoms, comprising 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), said group Ri optionally comprising one to six substituent(s), in particular one or two, selected from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, said group Ro optionally comprising one to six substituent(s) selected from -OH, -OR7 or OCOR7; or in which, in the composition comprising the primary plasticizer, the latter is a compound of formula (5) formula (5) in which Ro represents: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions; x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3, Ri and Rs represent: - a linear alkyl group of 1 to 30 carbon atom(s), or - a linear alkenyl group of 2 to 24 carbon atoms, comprising 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), Ri and R5 possibly comprising one to six substituent(s), in particular one or two, selected from -OH, -OR7 or OCOR7, wherein R7 is an alkyl group of 1 to 3 carbon atoms Ro possibly comprising one to six substituent(s) selected from -OH, -OR7 or OCOR7, and further comprising a step D of preparing a compound of formula (5) from a compound of formula (17) with an alcohol of formula (18) and an acid of formula (19): (17) (18) (19) formula (17) in which Ro represents: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3. Formulas (18) and (19) in which Ri and R5 independently represent: - a linear alkyl group of 1 to 30 carbon atom(s), or - a linear alkenyl group of 2 to 24 carbon atoms, comprising from 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), said Ri groups optionally comprising one to six substituent(s), in particular one or two, selected from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms R5, in addition to the -OH group represented in formula (18), possibly comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR7 or OCOR7 said group Ro possibly comprising one to six substituent(s) chosen from -OH, -OR7 or OCOR7.

14. A method according to any one of claims 10 or 11, wherein, in the composition comprising the primary plasticizing agent, the latter is a compound of formula (6) formula (6) in which Ro represents: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3 R represents: - a hydrogen atom, - a methyl group CH3, Ri and Re represent independently, and in particular can be identical: - a linear alkyl group of 1 to 30 carbon atom(s), or - a linear alkenyl group of 2 to 24 carbon atoms, comprising 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), Ri and Re optionally comprising one to six substituent(s), in particular one or two, selected from -OH, -OR7 or OCOR7, wherein R7 is an alkyl group of 1 to 3 carbon atoms Ro optionally comprising one to six substituent(s) selected from -OH, -OR7 or OCOR7, and further comprising a step E of preparation of said compound of formula (6) from a compound of formula (20) with an acid of formula (21) and an acid of formula (22) formula (20) in which Ro represents: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3. R represents: - a hydrogen atom, - a methyl group CH3, formulas (21) and (22) in which Ri and R6 represent independently, in particular can be identical: - a linear alkyl group of 1 to 30 carbon atom(s), or - a linear alkenyl group of 2 to 24 carbon atoms, comprising 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), Ri and Re possibly comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR? or OCOR?, in which R? is an alkyl group of 1 to 3 carbon atoms Ro possibly comprising one to six substituent(s) chosen from -OH, -OR? or OCOR?.

15. A method according to any one of claims 10 or 11, wherein, in the composition comprising the primary plasticizing agent, the latter is a compound of formula (7) Roep (7) formula (7) in which Roep represents: - a linear alkyl group of 15 carbon atoms containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 2, comprising y epoxide functions, y ranging from 1 to 2, x + y being less than or equal to 3, Roep optionally comprising one to six substituent(s) selected from -OH, -OR? or OCOR?, wherein R? is an alkyl group of 1 to 3 carbon atoms and further comprising a preparation step F of said compound of formula (7) from a compound of formula (15) formula (15) in which Ro represents: - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3, Ro possibly comprising one to six substituent(s) selected from -OH, -OR? or OCOR?, wherein R? is an alkyl group of 1 to 3 carbon atoms, or wherein, in the composition comprising the primary plasticizer, the latter is a compound of formula (8) OH o Y Roe O p H (8) formula (8) in which Roep represents: - a linear alkyl group of 15 carbon atoms containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 2, comprising y epoxide functions, y ranging from 1 to 2, x + y being less than or equal to 3, Roep possibly comprising one to six substituent(s) selected from -OH, -OR? or OCOR7, wherein R7 is an alkyl group of 1 to 3 carbon atoms and further comprising a preparation step G of a compound of formula (8) from a compound of formula (17) formula (17) in which Ro represents: - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3, Ro possibly comprising one to six substituent(s) selected from -OH, -OR7 or OCOR7, wherein R7 is an alkyl group of 1 to 3 carbon atoms; or wherein, in the composition comprising the primary plasticizer, the latter is a compound of formula (9) formula (9) in which Roep represents: - a linear alkyl group of 15 carbon atoms containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 2, comprising y epoxide functions, y ranging from 1 to 2, x + y being less than or equal to 3, Roep possibly comprising one to six substituent(s) chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms R4 represents: - a hydrogen atom, - a methyl group CH3, and further comprising a preparation step H of said compound of formula (9) from a compound of formula (20) formula (20) in which Ro represents - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3, Ro possibly comprising one to six substituent(s) chosen from -OH, -OR? or OCOR?, in which R? is an alkyl group of 1 to 3 carbon atoms R4 represents: - a hydrogen atom, - a methyl group CH3.

16. A method according to any one of claims 10 or 11, wherein, in the composition comprising the primary plasticizing agent, the latter is a compound of formula (10) formula (10) in which Roep represents: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3, Riep, possibly comprising one to six substituent(s) chosen from -OH, -OR? or OCOR?, in which R? is an alkyl group of 1 to 3 carbon atoms, represents: - a linear alkyl group of 1 to 30 carbon atoms, possibly containing 1 to 6 epoxide functions, or - a linear alkenyl group of 2 to 24 carbon atoms, possibly comprising 1 to 6 epoxide function(s), said alkenyl group possibly being substituted by an alkyl group of 1 to 5 carbon atom(s), Riep possibly comprising one to six substituent(s) chosen from -OH, -OR? or OCOR?, in which R? is an alkyl group of 1 to 3 carbon atoms, provided that at least one of the Roep or Ri groups ep comprises at least one epoxide function, and further comprising a step A of preparing a compound of formula (2) from a compound of formula (15) with an acid of formula (16) formulas (2) and (15) in which Ro represent: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3 Ro possibly comprising one to six substituent(s) chosen from -OH, -OR? or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, formula (2) and (16) in which Ri represent: - a linear alkyl group of 1 to 30 carbon atom(s), or - a linear alkenyl group of 2 to 24 carbon atoms, comprising 1 to 6 alkenyl function(s), said alkenyl group being optionally substituted by a linear alkyl group of 1 to 5 carbon atom(s), Ri possibly comprising one to six substituent(s) selected from -OH, -OR7 or OCOR7, wherein R7 is an alkyl group of 1 to 3 carbon atoms, and further comprising a step I of preparing the compound of formula (10) from a compound of formula (2), provided that at least one of the R groups o and Ri contains an alkenyl function.

17. A method according to any one of claims 10 or 11, wherein, in the composition comprising the primary plasticizing agent, the latter is a compound of formula (11), OH O [j^Uj^o xR5ep Roep (11) formula (11) in which R Oep represents: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3, Roep possibly comprising one to six substituent(s) chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms Rsep represents: - a linear alkyl group of 1 to 30 carbon atom(s), possibly containing 1 to 6 epoxide function(s) or - a linear alkenyl group of 2 to 24 carbon atoms, possibly comprising 1 to 6 epoxide function(s), said alkenyl group possibly being substituted by an alkyl group of 1 to 5 carbon atom(s), Rsep possibly comprising one to six substituent(s), in particular one or two, selected from -OH, -OR7 or OCOR7, wherein R7 is an alkyl group of 1 to 3 carbon atoms, provided that at least one of the Ro groups ep or R 5ep comprises at least one epoxide function and further comprising a preparation step B of a compound of formula (3) from a compound of formula (17) and an alcohol of formula (18) OH O OH O (Y °' R5 (Y ^^Ro OH R50H (3) (17) (18) formulas (3) and (17) in which Ro represent: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3, Ro possibly comprising one to six substituent(s) chosen from -OH, -OR? or OCOR?, in which R? is an alkyl group of 1 to 3 carbon atoms formulas (3) and (18) in which Rs represents: - a linear alkyl group of 1 to 30 carbon atom(s), or - a linear alkenyl group of 2 to 24 carbon atoms, comprising 1 to 6 alkenyl function(s), said alkenyl group optionally being substituted by a linear alkyl group of 1 to 5 carbon atom(s), said group Rs, in addition to the -OH group represented in formula (18), optionally comprising one to six substituent(s), in particular one or two, selected from -OH, -OR? and OCOR7, in which R? is an alkyl group of 1 to 3 carbon atom(s), and further comprising a preparation step J of a compound of formula (11) from a compound of formula (3), provided that at least one of the groups R oand R5 comprises an alkenyl function or wherein, in the composition comprising the primary plasticizer, the latter is a compound of formula (12) formula (12) in which Ro ep represents: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3 Roep possibly comprising one to six substituent(s) chosen from -OH, -OR? or OCOR?, in which R? is an alkyl group of 1 to 3 carbon atoms, Laugh P represents: - a linear alkyl group of 1 to 30 carbon atoms, possibly containing 1 to 6 epoxy function(s), or - a linear alkenyl group of 2 to 24 carbon atoms, possibly comprising 1 to 6 epoxide function(s), said alkenyl group possibly being substituted by an alkyl group of 1 to 5 carbon atom(s), R-iep possibly comprising one to six substituent(s), in particular one or two, selected from -OH, -OR? or OCOR?, in which R? is an alkyl group of 1 to 3 carbon atoms, provided that at least one of the Roep or Ri groups has at least one epoxide function, and further comprising a step C of preparation of a compound of formula (4) from a compound of formula (17) and an acid of formula (19): formulas (4) and (17) in which R o represent: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3, Ro possibly comprising one to six substituent(s) chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms formulas (4) and (19) in which Ri represents: - a linear alkyl group of 1 to 30 carbon atom(s), or - a linear alkenyl group of 2 to 24 carbon atoms, comprising 1 to 6 alkenyl function(s), said alkenyl group optionally being substituted by a linear alkyl group of 1 to 5 carbon atom(s), said group Ri optionally comprising one to six substituent(s), in particular one or two, selected from -OH, -OR7 and OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s), provided that at least one of the R groups oand Ri comprises an alkenyl function, and further comprising a preparation step K of a compound of formula (12) from a compound of formula (4); or wherein, in the composition comprising the primary plasticizer, the latter is a compound of formula (13) formula (13) in which Ro ep represents: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3, Roep possibly comprising one to six substituent(s) chosen from -OH, -OR? or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms Laugh P and Rsep represent independently: - a linear alkyl group of 1 to 30 carbon atoms, possibly containing 1 to 6 epoxide functions, or - a linear alkenyl group of 2 to 24 carbon atoms, possibly comprising 1 to 6 epoxide function(s), said alkenyl group possibly being substituted by an alkyl group of 1 to 5 carbon atom(s), Riep and Rsep possibly comprising one to six substituent(s), in particular one or two, selected from -OH, -OR7 or OCOR7, wherein R7 is an alkyl group of 1 to 3 carbon atoms, provided that at least one of the Roep, Riep or Rsep groups has at least one epoxide function, and further comprising a preparation step D of a compound of formula (5) from a compound of formula (17) with an alcohol of formula (18) and an acid of formula (19), formulas (5) and (17) in which R o represents: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3, Ro possibly comprising one to six substituent(s) chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, formulas (5), (18) and (19) in which Ri and R5 independently represent: - a linear alkyl group of 1 to 30 carbon atom(s), or - a linear alkenyl group of 2 to 24 carbon atoms, comprising 1 to 6 alkenyl function(s), said alkenyl group optionally being substituted by a linear alkyl group of 1 to 5 carbon atom(s), said group Ri, optionally comprising one to six substituent(s), in particular one or two, selected from -OH, -OR7 and OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s), said group Rs, in addition to the -OH group represented in formula (18), optionally comprising one to six substituent(s), in particular one or two, selected from -OH, -OR7 and OCOR7, provided that at least one of the R groups o , Ri or R5 comprises an alkenyl function and further includes a preparation step L of a compound of formula (13) from a compound of formula (5).

18. A method according to any one of claims 10 or 11, wherein, in the composition comprising the primary plasticizing agent, the latter is a compound of formula (14) Rûep (14) formula (14) in which Ro ep represents: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3, Roep possibly comprising one to six substituent(s) chosen from -OH, -OR7 or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, R4 is chosen from: - a hydrogen atom, - a methyl group CH3, Riep and Reep represent independently, in particular they can be identical: - a linear alkyl group of 1 to 30 carbon atom(s), possibly containing 1 to 6 epoxide function(s) or - a linear alkenyl group of 2 to 24 carbon atoms, possibly comprising 1 to 6 epoxide function(s), said alkenyl group possibly being substituted by an alkyl group of 1 to 5 carbon atom(s), Riep and Reep possibly comprising one to six substituent(s), in particular one or two, selected from -OH, -OR7 or OCOR7, wherein R7 is an alkyl group of 1 to 3 carbon atoms, provided that at least one of the Ro groups ep , Riep or Reep comprises at least one epoxide function, and further comprising a step E of preparing the compound of formula (6) from a compound of formula (20) with an acid of formula (21) and an acid of formula (22): formulas (6) and (20) in which R o represent: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3 Ro possibly comprising one to six substituent(s) chosen from -OH, -OR7 or OCORy, in which R? is an alkyl group of 1 to 3 carbon atoms, R4 represents: - a hydrogen atom, - a methyl group CH3, formulas (6), (21) and (22) in which Ri and R6 independently represent: - a linear alkyl group of 1 to 30 carbon atom(s), or - a linear alkenyl group of 2 to 24 carbon atoms, comprising 1 to 6 alkenyl function(s), said alkenyl group optionally being substituted by a linear alkyl group of 1 to 5 carbon atom(s), said group R4 optionally comprising one to six substituent(s), in particular one or two, selected from -OH, -OR₂ and OCOR₇, in which R7 is an alkyl group of 1 to 3 carbon atom(s), provided that at least one of the R groups o , Ri or R6 comprises an alkenyl function, and further comprising a step M of preparation of the compound of formula (14) from a compound of formula (6).

19. Plastic material comprising cellulose acetate which can be obtained by a process according to any one of claims 10 to 18.

20. Compound of formula (I) formula (1) in which • R is chosen from: - a hydrogen atom - a CO-R1 group, • Ro is chosen from: - a linear alkyl group of 15 carbon atoms, possibly containing 1 to 3 epoxide functions or, - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3, • R2 is chosen from: - a hydrogen atom, formula - a carboxylic acid function COOH • R3 are independently chosen from: - a hydrogen atom, - -OC-O-Re formula R °Y6O - an alcohol functional group (OH), • R4 is chosen from: - a hydrogen atom, - a methyl group CH3, • Ri, Rs and Re, which are identical or different, are chosen from: - a linear alkyl group of 2 to 30 carbon atoms, possibly containing 1 to 6 epoxide functions, or - a linear alkenyl group of 2 to 24 carbon atoms, possibly comprising 1 to 6 epoxide function(s), said alkenyl group possibly being substituted by an alkyl group of 1 to 5 carbon atom(s), Ro, Ri, Rs and Re possibly comprising one to six substituent(s), in particular one or two, chosen from -OH, -OR? or OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms, provided that at least one of the OR, R2 or R3 groups is an ester function and / or at least one of R o , Ri, Rs or R6 comprises at least one epoxide function and provided that when the compound of formula (1) is: then the compound contains at least one epoxide function, the following compounds being excluded:

21. Compound according to claim 20, of formula (1) selected from the following formulas, (3), (4), (5) and (6), (5) (6) Ro represents: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3, R4 is chosen from: - a hydrogen atom, - a methyl group CH3 Ri, R5 and Re are chosen from: - a linear alkyl group of 2 to 30 carbon atom(s), or - a linear alkenyl group of 2 to 24 carbon atoms, said alkenyl group optionally being substituted by an alkyl group of 1 to 5 carbon atom(s), in particular in which: - Ro is chosen from among: said group R o including possibly 1 to 6 substituent(s) chosen from -OH, -OR7 and OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atom(s) said groups Ri, R5 and R6 including possibly 1 to 6 substituent(s), in particular one or two, chosen from -OH, -OR7 and OCOR7.

22. Compound according to claim 20, of formula (1) selected from the following formulas (8) and (9), (8) (9) Roep represents: - a linear alkyl group of 15 carbon atoms containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 2, comprising y epoxide functions, y ranging from 1 to 2, x + y being less than or equal to 3, said group R Oepcomprising possibly 1 to 6 substituent(s) chosen from -OH, -OR7 and OCOR7, in which R7 is an alkyl group of 1 to 3 carbon atoms. In particular, in which: Roep is chosen from among:

23. Compound according to claim 20, selected from the following formulas (10), (11), (12), (13) and (14), Roep represents: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3, R4 is chosen from: - a hydrogen atom, - a methyl group CH3 Riep, Rsep and Ree Pare chosen independently from: o an alkyl group of 2 to 30 carbon atoms, possibly comprising 1 to 6 epoxide functions, o a linear alkenyl group of 2 to 24 carbon atoms, in particular comprising 1 to 6 epoxide functions, said alkenyl group possibly being substituted by an alkyl chain of 1 to 5 carbon atoms, provided that at least one of the Roep, Riep, Rsep or Roep groups comprises at least one epoxide function, in particular in which - Roep is chosen from among: said Ro group ep comprising possibly 1 to 6 substituent(s) chosen from -OH, -OR7 and OCOR7, wherein R7 is an alkyl group of 1 to 3 carbon atoms, said Ri groups ep , Rsep and R 6e p possibly including 1 to 6 substituent(s), in particular one or two, chosen from -OH, -OR7 and OCOR7.

24. Compound according to any one of claims 20 or 23, selected from the following formulas (11), (12), (13) and (14), Roep represents: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising / alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3, R4 is chosen from: - a hydrogen atom, - a methyl group CH3 R-iep, sep and e ep are chosen independently from: o an alkyl group of 2 to 30 carbon atoms, possibly comprising 1 to 6 epoxide functions, o a linear alkenyl group of 2 to 24 carbon atoms, in particular comprising 1 to 6 epoxide functions, said alkenyl group possibly being substituted by an alkyl chain of 1 to 5 carbon atoms, provided that at least one of the R groups Oep Ri ep , Rsep or R 6ep includes at least one epoxide function, in particular in which Roep is chosen from among: said Roep group possibly comprising 1 to 6 substituent(s) selected from -OH, -OR7 and OCOR7, wherein R7 is an alkyl group of 1 to 3 carbon atoms, said Riep, Rsep and R groups 6ep possibly including 1 to 6 substituent(s), in particular one or two, chosen from -OH, -OR7 and OCOR7.

25. Compound according to claim 20, of formula (10) formula (2) in which • Roep is chosen from among: - a linear alkyl group of 15 carbon atoms possibly containing 1 to 3 epoxide functions, or - a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x ranging from 1 to 3, comprising y epoxide functions, y ranging from 0 to 2, x + y being less than or equal to 3, • Riep is chosen from among: - a linear alkyl group of 3 to 13 or 15 to 30 carbon atom(s), possibly containing 1 to 6 epoxide function(s), or - a linear alkenyl group of 2 to 17 or 19 to 24 carbon atoms, possibly comprising 1 to 6 epoxide function(s), said alkenyl group possibly being substituted by an alkyl group of 1 to 5 carbon atom(s), Roep and Riep possibly comprising one to six substituent(s) chosen from -OH, -OR7 or OCORy, in which R? is an alkyl group of 1 to 3 carbon atoms, provided that Ro ep or Ri ep includes at least one epoxide function.

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